betadex profile

beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	444041
CHEMBL ID	415690
CHEBI ID	495055
SCHEMBL ID	24215
MeSH ID	M0098264

Synonym
ss-cyclodextrin
beta-schardinger dextrin
CHEMBL415690
ins-459
ins no.459
oristar bcd
betacd
e459
cyclodextrin, beta-
e-459
cavamax w7
ringdex-b
beta cyclodextrin
.beta.-cyclodextrin
cycloheptaglucan
cycloheptaamylose
nsc-269471
cycloheptaglucosan
cyclomaltoheptaose
beta-cycloamylose
ringdex b
ai3-29233
rhodocap n
ccris 651
einecs 231-493-2
dextrin, beta-cyclo
kleptose
b-cyclodextrin
kleptose b
nsc 314334
beta-dextrin
beta-cycloheptaamylose
cycloheptapentylose
ringdex bl
caraway
nsc-314334
heptakis(hydroxymethyl)[?]tetradecol
NCGC00090771-01
beta-cyclodextrin, produced by wacker chemie ag, burghausen, germany
beta-cyclodextrin, >=97%
beta-cyclodextrin, powder, bioreagent, suitable for cell culture, >=97%
1DMB
DB03995
betadex
cyclodextrin b
betadex (nf/inn)
D02401
NCGC00090771-02
C-9120
CHEBI:495055 ,
beta-cd
3CK8
beta-cyclodextrins
NCGC00090771-03
tox21_201006
NCGC00258559-01
tox21_111017
cas-7585-39-9
dtxsid1020358 ,
dtxcid70358
79647-56-6
betadex [usan:inn:ban:nf]
unii-jv039jzz3a
ec 231-493-2
jv039jzz3a ,
AKOS015900444
cyclo-epta-amylose
nsc 269471
beta-cyclodextrin [fcc]
betadex [who-dd]
betadex [inn]
beta cyclodextrin [usp-rs]
betadex [mart.]
.beta.-cyclodextrin [fhfi]
.beta.-cyclodextrin [mi]
alfadex impurity a [ep impurity]
sulfobutylbetadex sodium impurity a [ep impurity]
betadex [ep monograph]
betadex [ii]
cycloheptakis-(1->4)-(.alpha.-d-glucopyranosyl)
SCHEMBL24215
2ZYN
3M3R
2Y4S
tox21_111017_1
NCGC00090771-04
WHGYBXFWUBPSRW-FOUAGVGXSA-N
beta-cyclodextrine
schardinger a-dextrin
bdbm11
beta-cyclodextrin, produced by wacker chemie ag, burghausen, germany, life science, >=98.0% (hplc)
betadex, european pharmacopoeia (ep) reference standard
beta-cyclodextrin, produced by wacker chemie ag, burghausen, germany, >=95.0% (hplc)
mfcd00078139
beta cyclodextrin, united states pharmacopeia (usp) reference standard
beta-cyclodextrin, pharmaceutical secondary standard; certified reference material
37331-89-8
maltodecaose dp10
Z1954805533
CS-0027620
HY-107201
D047392000 ,
Q27077120
beta-cyclo-dextrin
betacyclodextrin
betadex (ep monograph)
beta cyclodextrin (usp-rs)
betadex (mart.)
betadex (ii)
cycloheptakis-(1->4)-(alpha-d-glucopyranosyl)
betadexum
alfadex impurity a (ep impurity)
EN300-381041

Excerpt	Reference	Relevance
"Effects of water-soluble beta-cyclodextrins (beta CDs) on intestinal epithelial integrity were investigated, to establish the safe use of these beta CDs as solubilizers of spironolactone in paediatric enteral solutions."	( Intestinal safety of water-soluble beta-cyclodextrins in paediatric oral solutions of spironolactone: effects on human intestinal epithelial Caco-2 cells. Mannermaa, JP; Schipper, NG; Thompson, DO; Tötterman, AM, 1997)	0.3
"By using nerve growth factor-differentiated PC12 cells as a model for sympathetic neurons, we have recently shown that cholesterol oxides are toxic to cells of neural origin."	( Toxicity of cholesterol oxides on cultured neuroretinal cells. Chang, JY; Liu, LZ, 1998)	0.3
"These results suggest that, in addition to causing pathological changes in cells directly involved in atherosclerosis, cholesterol oxides may be toxic to cells derived from neuroretinas."	( Toxicity of cholesterol oxides on cultured neuroretinal cells. Chang, JY; Liu, LZ, 1998)	0.3
" The miconazole complex was more toxic to erythrocytes than the physical mixture."	( Cyclodextrin inclusion complexes of miconazole and econazole--isolation, toxicity on human cells, and confirmation of a new interpretation of the drug supersaturation phenomenon. Jacobsen, J; Pedersen, M; Sørensen, AM, 1999)	0.3
" The miconazole hydroxypropyl-beta-cyclodextrin product and genuine cyclodextrin inclusion complexes of miconazole, econazole and clotrimazole were toxic on a human TR146 buccal cell culture model."	( Cyclodextrin inclusion complexes of antimycotics intended to act in the oral cavity--drug supersaturation, toxicity on TR146 cells and release from a delivery system. Bjerregaard, S; Jacobsen, J; Pedersen, M, 1999)	0.3
"Cell degeneration in Alzheimer's disease is mediated by a toxic mechanism that involves interaction of the AbetaP peptide with the plasma membrane of the target cell."	( Plasma membrane cholesterol controls the cytotoxicity of Alzheimer's disease AbetaP (1-40) and (1-42) peptides. Arispe, N; Doh, M, 2002)	0.31
" But OL/4 complexed is even more toxic than complexed fomocaine."	( Effects and toxicity of new fomocaine derivatives and of 2-hydroxypropyl-beta-cyclodextrin inclusion compounds in rats. Fleck, C; Oelschläger, H; Wange, J; Wennek-Klose, J, 2004)	0.32
" Therefore, the highly water-soluble RAMEB is thought to be a safe candidate as an excipient for buccal mucosal drug delivery."	( Evaluation of buccal methyl-beta-cyclodextrin toxicity on human oral epithelial cell culture model. Bochot, A; Boulmedarat, L; Fattal, E; Lesieur, S, 2005)	0.33
" Treating these cultures with caspase-3 inhibitor z-VAD-fmk did not protect the cells from MbetaCD toxic effects."	( Characterization of methyl-beta-cyclodextrin toxicity in NGF-differentiated PC12 cell death. Almaguel, FG; Bu, L; De Leon, M; Liu, JW; Padilla, A; Ulloth, JE, 2007)	0.34
" Ionic beta-CDs were less toxic than the methylated derivatives."	( Cytotoxicity of different types of methylated beta-cyclodextrins and ionic derivatives. Bacskay, I; Feher, P; Fenyvesi, E; Fenyvesi, F; Kiss, T; Kocsan, R; Pasztor, N; Szabo, G; Szente, L; Varadi, J; Vecsernyes, M, 2007)	0.34
" From the viewpoint of developing effective and safe protein transduction technology, although Tat was the most versatile carrier among the peptides studied, PTDs should be selected based on their individual characteristics."	( Comparative study on transduction and toxicity of protein transduction domains. Imai, S; Kamada, H; Mukai, Y; Nagano, K; Nakagawa, S; Shibata, H; Sugita, T; Tsunoda, SI; Tsutsumi, Y; Yamanada, N; Yoshida, Y; Yoshikawa, T; Yoshioka, Y, 2008)	0.35
"The exponential increase in the number of new nanomaterials that are being produced increases the likelihood of adverse biological effects in humans and the environment."	( Cationic polystyrene nanosphere toxicity depends on cell-specific endocytic and mitochondrial injury pathways. Kovochich, M; Liong, M; Nel, AE; Xia, T; Zink, JI, 2008)	0.35
" IM is considered to form partial inclusion complexes with HP-beta-CD by enclosure of the p-chlorobenzoic part of the molecule in the cyclodextrin channel, reducing the adverse effects."	( Evaluation of gastric toxicity of indomethacin acid, salt form and complexed forms with hydroxypropyl-beta-cyclodextrin on Wistar rats: histopathologic analysis. Cabrita, AM; Caramona, MM; Castel-Branco, MM; Figueiredo, IV; Ribeiro-Rama, AC; Veiga, F, 2009)	0.35
" Caution should be exercised in using cyclodextrins to remove the cellular lipid raft-associated cholesterol as the cyclodextrins cause adverse effects on cells such as loss of cell viability or induction of cytotoxicity."	( A simple method for effective and safe removal of membrane cholesterol from lipid rafts in vascular endothelial cells: implications in oxidant-mediated lipid signaling. Hinzey, A; Kline, MA; Kotha, SR; Marsh, CB; O'Connor Butler, ES; Parinandi, NL; Sliman, S; Uppu, RM, 2010)	0.36
" Cell toxicity of methylated-beta-CDs was the highest, while ionic derivatives proved to be less toxic than methylated ones."	( Evaluation of the cytotoxicity of beta-cyclodextrin derivatives: evidence for the role of cholesterol extraction. Bácskay, I; Fenyvesi, E; Fenyvesi, F; Iványi, R; Kiss, T; Szente, L; Tósaki, A; Váradi, J; Vecsernyés, M, 2010)	0.36
" These results will provide useful information for HPn-SBEm-β-CD as a promising safe adjuvant for intravenous administration in the future."	( Evaluation of cholesterol depletion as a marker of nephrotoxicity in vitro for novel β-cyclodextrin derivatives. Chen, C; Tao, Q; Wang, H; Xie, X; Yu, S; Zhang, F; Zhou, C; Zhou, Q; Zou, Y, 2011)	0.37
" Based on these results, the cross-linked β-CD did not produce any signs of toxicity or other adverse effects at dose levels up to 2000 mg/kg per d for 14 days."	( Single- and 14-day repeat-dose toxicity of cross-linked β-cyclodextrin in rats. Choi, KH; Kwak, HS; Park, JH, 2011)	0.37
" The incubation of cells with MCD inhibited the generation of the vacuoles and the toxic effects of Gln."	( An active endocytosis pathway is required for the cytotoxic effects of glycosylated antitumor ether lipids. Arthur, G; Bittman, R; Byun, HS; Samadder, P, 2011)	0.37
"PVP-CD was proved safe and demonstrated excellent biocompatibility, healing and degradation properties."	( Safety, healing, and efficacy of vascular prostheses coated with hydroxypropyl-β-cyclodextrin polymer: experimental in vitro and animal studies. Blanchemain, N; Haulon, S; Hildebrand, HF; Jean-Baptiste, E; Martel, B; Neut, C, 2012)	0.38
"2 min) when injected at the same dose (1 μg kg(-1)), prolonging the duration of analgesia after intramuscular administration and representing an alternative on the development of effective and safe drug-delivery system for opioid analgesics."	( Sufentanil-2-hydroxypropyl-β-cyclodextrin inclusion complex for pain treatment: physicochemical, cytotoxicity, and pharmacological evaluation. Braga, AF; Cereda, CM; De Araujo, DR; De Paula, E; Fraceto, LF; Franco, MK; Moraes, CM; Nunes, LA; Tófoli, GR; Volobuef, C; Yokaichiya, F, 2012)	0.38
"Although NSAIDs are very effective drugs, their use is associated with a broad spectrum of adverse reactions in the liver, kidney, cardiovascular (CV) system, skin and gut."	( Piroxicam-β-cyclodextrin: a GI safer piroxicam. Scarpignato, C, 2013)	0.39
" These results indicate that the treatment of sewage sludge with cyclodextrin could allow their safe use as fertiliser in agriculture."	( Decontamination of polycyclic aromatic hydrocarbons and nonylphenol from sewage sludge using hydroxypropyl-β-cyclodextrin and evaluation of the toxicity of leachates. Barata, C; Lacorte, S; Morillo, E; Sánchez-Trujillo, MA; Villaverde, J, 2014)	0.4
" The toxicity and adverse side effects renders the potent drug to limits its usage."	( Investigation on the inclusion and toxicity of acriflavine with cyclodextrins: a spectroscopic approach. Manivannan, C; Meenakshi Sundaram, K; Renganathan, R; Sundararaman, M, 2014)	0.4
"No significant changes in blood pressure, heart rate, or adverse events including rash were attributed to administration of a 50-mg dose of the intravenous LTG formulation."	( Safety of an intravenous formulation of lamotrigine. Birnbaum, AK; Conway, JM; Leppik, IE; Pennell, PB; Rarick, JO; Remmel, RP; White, JR, 2014)	0.4
" In order to investigate the suitability of 6-OxP-CD as a small molecule scavenger an in vivo guinea pig model was established to determine the protective effect of 6-OxP-CD against the highly toxic nerve agent cyclosarin."	( Effectiveness of a substituted β-cyclodextrin to prevent cyclosarin toxicity in vivo. Kubik, S; Seeger, T; Thiermann, H; Wille, T; Worek, F; Zengerle, M, 2014)	0.4
" These findings provide significant information that can be used to design further studies aimed at developing less toxic eye drops."	( A nanoparticle formulation reduces the corneal toxicity of indomethacin eye drops and enhances its corneal permeability. Ito, Y; Nagai, N; Okamoto, N; Shimomura, Y, 2014)	0.4
"Constructing safe and effective gene delivery carriers is becoming highly desirable for gene therapy."	( Recycling gene carrier with high efficiency and low toxicity mediated by L-cystine-bridged bis(β-cyclodextrin)s. Chen, JT; Chen, Y; Liu, Y; Yang, Y; Zhang, YH; Zhang, YM, 2014)	0.4
" The aim of sharing these data, including adverse findings, is to provide meaningful information for vehicle selection, thereby avoiding repetition of animal experimentation."	( Safety data on 19 vehicles for use in 1 month oral rodent pre-clinical studies: administration of hydroxypropyl-ß-cyclodextrin causes renal toxicity. Burdett, L; Cotton, P; Finney, R; Garner, C; Hargreaves, A; Harris, J; Healing, G; Kirk, S; Pivette, P; Schramm, C; Sulemann, T, 2016)	0.43
" Preliminary in vitro cytotoxicity tests showed that the complexes are less toxic to normal liver cells than free chlorzoxazone."	( Inclusion complexes of chlorzoxazone with β- and hydroxypropyl-β-cyclodextrin: Characterization, dissolution, and cytotoxicity. Li, H; Li, S; Tang, P; Wang, L; Yan, J; Yang, H, 2015)	0.42
" Moreover, BCD-dextran resulted less toxic on cell cultures due to higher selectivity in sequestering cholesterol in comparison to MBCD (that sequestrated also significant amounts of cholesteryl esters)."	( β-CD-dextran polymer for efficient sequestration of cholesterol from phospholipid bilayers: Mechanistic and safe-toxicity investigations. di Cagno, M; Hansen, T; Nielsen, TT; Stelzl, D, 2015)	0.42
" Finally, the new formulation of progesterone was shown to be safe and not inferior to other products already on the market, with the exception of progesterone administered vaginally."	( Efficacy and Safety Profile of Diclofenac/Cyclodextrin and Progesterone/Cyclodextrin Formulations: A Review of the Literature Data. Bonagura, AC; Cenami, R; Cimmaruta, D; Fiorentino, S; Fossati, T; Rossi, F; Scavone, C; Torella, M, 2016)	0.43
" Data are limited regarding CV risks associated with short-term nonsteroidal anti-inflammatory drug use, including injectable formulations, although it has been suggested that even a single dose may increase CV adverse event (AE) risk."	( Cardiovascular safety of hydroxypropyl-β-cyclodextrin-diclofenac in the management of acute postsurgical pain: a pooled analysis of 2 randomized, double-blind, placebo- and active comparator-controlled phase III clinical trials. Carr, DB; Daniels, SE; Gan, TJ; Lacouture, PG; Min, LH; Reyes, CR; Singla, N, 2016)	0.43
" Renal safety was assessed by examining treatment-emergent adverse events (AEs) and postoperative blood urea nitrogen (BUN) and serum creatinine shifts."	( A Pooled Analysis Evaluating Renal Safety in Placebo- and Active Comparator-Controlled Phase III Trials of Multiple-Dose Injectable HPβCD-Diclofenac in Subjects with Acute Postoperative Pain. Carr, DB; Daniels, SE; Gan, TJ; Hamilton, DA; Johnson, O; Lacouture, PG; Min, LH; Reyes, CR; Singla, N, 2016)	0.43
" It has been shown that βCD-IONPs does not have any significant toxic effect at the cellular level."	( Detailed toxicity evaluation of β-cyclodextrin coated iron oxide nanoparticles for biomedical applications. Chandra, S; Khanna, A; Shelat, R, 2018)	0.48
" We conclude that acid-labile PRXs are promising candidates for the treatment of macular diseases through the removal of toxic metabolites."	( Acid-Induced Intracellular Dissociation of β-Cyclodextrin-Threaded Polyrotaxanes Directed toward Attenuating Phototoxicity of Bisretinoids through Promoting Excretion. Nishida, K; Ohashi, M; Tamura, A; Yui, N, 2017)	0.46
"In the acute toxicity test, the value of LD50 of BJO-CDP was 11."	( Preparation, Characterization, Toxicity and Pharmacodynamics of the Inclusion Complex of Brucea javanica Oil with β-cyclodextrin Polymers. Chen, L; Hu, R; Pan, B; Song, XH; Wang, XC; Wu, HH; Xu, RR, 2017)	0.46
"Although fibrillar amyloid beta peptide (Aβ) aggregates are one of the major hallmarks of Alzheimer's disease, increasing evidence suggests that soluble Aβ oligomers are the primary toxic species."	( Porphyrin Cyclodextrin Conjugates Modulate Amyloid Beta Peptide Aggregation and Cytotoxicity. Bellia, F; Giuffrida, ML; Oliveri, V; Tomasello, MF; Vecchio, G; Zimbone, S, 2018)	0.48
"Nanomedicines have achieved several breakthroughs in cancer treatment over the past decades; however, their potential immunotoxicities are ignored, which results in serious adverse effects and greatly reduces the potential in clinical translation."	( Supramolecular Polymer-Based Nanomedicine: High Therapeutic Performance and Negligible Long-Term Immunotoxicity. Chen, X; Gao, C; He, Z; Hua, B; Huang, F; Huang, X; Jacobson, O; Liu, Y; Mao, Z; Wang, W; Wang, Z; Yu, C; Yu, G; Zhang, F; Zhao, X; Zhou, J; Zhu, X, 2018)	0.48
" elegans that in turn, affects general toxic outcome, such as, decrease in reproductive ability."	( Clathrin-mediated endocytosis is involved in uptake and toxicity of silica nanoparticles in Caenohabditis elegans. Choi, J; Eom, HJ, 2019)	0.51
"Single and multiple doses of 2-IB up to 6 doses of 6 mg/kg with and without Captisol® were safe and well-tolerated in healthy male subjects."	( First-in-Human Study of the Safety, Tolerability, Pharmacokinetics and - Preliminary Dynamics of Neuroprotectant 2-Iminobiotin in Healthy Subjects. de Leede, LGJ; Hartstra, J; Leufkens, PWTJ; Peeters-Scholte, CMPCD; van Hoogdalem, EJ; van Lier, JJ, 2020)	0.56
" Regarding the toxicity of the two compounds, our results showed that ABF1-βCD has less toxic effect than baclofen; it reduces the activity of ALT and AST enzymes."	( Synthesis and Biological Analysis of Anti-addiction Effect and Hepatotoxicity of Tow Baclofen Analogues Complexed with β-Cyclodextrin. Dib, MEA; El Ouar, I; Keniche, A; Zeghina, I, 2022)	0.72
" RMβCD was found to be more toxic to retinal explants when compared to HPβCD, which the retina can safely tolerate at levels as high as 10 mM."	( Cytotoxicity of β-Cyclodextrins in Retinal Explants for Intravitreal Drug Formulations. Christensen, G; Loftsson, T; Paquet-Durand, F; Prajapati, M, 2021)	0.62
" Cyclodextrins, which are most commonly used to reduce the undesirable features of contained drugs within their hydrophobic interior, also have the potential to alter the toxic behavior of the drug."	( The Interaction of Heptakis (2,6-di-O-Methyl)-β-cyclodextrin with Mianserin Hydrochloride and Its Influence on the Drug Toxicity. Belica-Pacha, S; Bryszewska, M; Budryn, G; Daśko, M; Małecka, M; Miłowska, K; Oracz, J; Pałecz, B, 2021)	0.62
" It reduces the systemic adverse toxicity issues of drugs carrier, making this system ideal for nasopharyngeal cancer treatment."	( Self-assembling porphyrin conjugate-carboplatin(IV) prodrug nanoparticles for enhancing high efficacy nasopharyngeal cancer and low systemic toxicity. Peng, Q; Su, R; Wang, W; Zhang, X, 2022)	0.72
"Although paraquat is a widely used herbicide, it is toxic to humans if ingested or absorbed through an open wound."	( β-Cyclodextrin/Azobenzene Microspheres Loaded with Paraquat Are Safe and Effective. Li, C; Li, X; Wang, Y; Wang, Z, 2023)	0.91

Excerpt	Reference	Relevance
" The pharmacokinetic behavior of both cyclodextrins was similar to that of inulin, showing rapid distribution over extracellular fluids."	( The pharmacokinetics of beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin in the rat. Frijlink, HW; Hefting, NR; Lerk, CF; Meijer, DK; Oosting, R; Visser, J, 1990)	0.28
" The terminal half-life in plasma of cicaprost was approx."	( Pharmacokinetics and pharmacodynamics of cicaprost in healthy volunteers after oral administration of 5 to 20 micrograms. Hildebrand, M; Nieuweboer, B; Staks, T, 1990)	0.28
" It is therefore confirmed that piroxicam beta-cyclodextrin has the same pharmacokinetic behaviour at the steady-state in elderly subjects, as the active principle in a non-complexed form."	( Pharmacokinetic study on piroxicam at the steady-state in elderly subjects and younger adults after administration of piroxicam beta-cyclodextrin. Acerbi, D; Bonati, C; Boscarino, G; Bufalino, L; Cesari, F; D'Ambrosio, E; Mansanti, P; Scali, G, 1988)	0.27
"The effects of beta- and gamma-cyclodextrins (CyDs) on the pharmacokinetic behavior of prednisolone after intravenous or intramuscular administration in rabbits were investigated."	( Effects of beta- and gamma-cyclodextrins on the pharmacokinetic behavior of prednisolone after intravenous and intramuscular administrations to rabbits. Arimori, K; Uekama, K, 1987)	0.27
" In short term pharmacodynamic studies in healthy volunteers, piroxicam-beta-cyclodextrin was equivalent to or tended to show less gastrointestinal mucosal toxicity than standard piroxicam, as assessed by endoscopy and faecal blood loss."	( Piroxicam-beta-cyclodextrin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in rheumatic diseases and pain states. Balfour, JA; Lee, CR, 1994)	0.29
" Pharmacokinetic studies indicated that glycofurol inhibited CBZ metabolism by decreasing formation of the major CBZ metabolite CBZ-10,11-epoxide (CBZ-E)."	( New injectable aqueous carbamazepine solution through complexing with 2-hydroxypropyl-beta-cyclodextrin: tolerability and pharmacokinetics after intravenous injection in comparison to a glycofurol-based formulation. Brewster, ME; Düsing, R; Hönack, D; Löscher, W; Richter, A; Schulz, HU; Schürer, M, 1995)	0.29
" Pharmacokinetic studies comparing piroxicam beta-cyclodextrin with plain piroxicam have been carried out in both patients and healthy subjects."	( Supermolecular inclusion of piroxicam with beta-cyclodextrin: pharmacokinetic properties in man. Acerbi, D; Merz, PG; Rietbrock, N; Rietbrock, S; Woodcock, BG, 1993)	0.29
" The pharmacokinetic profiles of piroxicam in rat lymph were very similar in both groups."	( Pharmacokinetic profile of piroxicam beta-cyclodextrin, in rat plasma and lymph. Bersani-Amado, CA; Kimura, E; Oga, S; Santos, SR; Sudo, LS, 1997)	0.3
" At steady state, mean bioavailabilities were 29% and 17% higher, respectively, in the fasted state; terminal half-life was similar under fasted and fed conditions (mean 39."	( Food interaction and steady-state pharmacokinetics of itraconazole oral solution in healthy volunteers. Barone, JA; Bierman, RH; Colaizzi, JL; Guarnieri, J; Hassell, AE; Jessen, L; Moskovitz, BL, )	0.13
" Using this immunoassay, we have evaluated the main pharmacokinetic parameters of 6-monoamino-beta-CD after iv administration to the rat of a 25 mg/kg dose."	( Pharmacokinetic analysis of 6-monoamino-beta-cyclodextrin after intravenous or oral administration to rats using a specific enzyme immunoassay. Créminon, C; Djedaïni-Pilard, F; Grassi, J; Grognet, JM; Péan, C; Perly, B; Pradelles, P; Vienet, R, 1999)	0.3
" MEBCD pharmacokinetic profile was consistent with a two-compartment model (t1/2 alpha: 30 min; t1/2 beta: 7 h)."	( Methyl-beta-cyclodextrin and doxorubicin pharmacokinetics and tissue concentrations following bolus injection of these drugs alone or together in the rabbit. Bressolle, F; Grosse, PY; Joulia, JM; Pinguet, F; Rouanet, P, 1999)	0.3
" The pharmacokinetic data were best described by a two-compartment model with first-order absorption."	( Comparative population pharmacokinetic-pharmacodynamic analysis for piroxicam-beta-cyclodextrin and piroxicam. Hu, C; Miller, R; Wang, D; Zheng, J, 2000)	0.31
" Plasma concentration versus time curves show that the complex and the mixture of acyclovir/complex have a higher bioavailability and a pharmacokinetic profile than that of the drug itself."	( Preliminary pharmacokinetic study of different preparations of acyclovir with beta-cyclodextrin. Aránguiz, T; Hernández, L; Luengo, J; Sepúlveda, J; Von Plessing, C, 2002)	0.31
" Intravenous pharmacokinetic profiles for both FLT and FLT-2-OH were identical following either FLT-HPBetaCyD or FLT-COSOLV, indicating that the FLT-HPBetaCyD formulation behaved as a true solution."	( Hydroxypropyl-beta-cyclodextrin-flutamide inclusion complex. II. Oral and intravenous pharmacokinetics of flutamide in the rat. Diakur, J; Tam, YK; Wiebe, LI; Zuo, Z, )	0.13
"It has become increasingly popular in drug development to conduct discovery pharmacokinetic (PK) studies in order to evaluate important PK parameters of new chemical entities (NCEs) early in the discovery process."	( Post-column infusion study of the 'dosing vehicle effect' in the liquid chromatography/tandem mass spectrometric analysis of discovery pharmacokinetic samples. Naidong, W; Shou, WZ, 2003)	0.32
" The pharmacokinetic properties of digoxin after oral administration of its hydroxypropyl-beta-cyclodextrin (HPCD) inclusion complex to rabbits and human volunteers were investigated in comparison with those of commercially available tablets."	( Effects of 2-hydroxypropyl-beta-cyclodextrin on pharmacokinetics of digoxin in rabbits and humans. He, ZG; Li, YS; Tang, X; Zhang, RH; Zhang, TH; Zhao, C, 2004)	0.32
" Dialysis had no effect on the half-life and clearance of ITC or OH-ITC."	( Pharmacokinetics of intravenous itraconazole in stable hemodialysis patients. Finkel, KW; Leitz, GJ; Mohr, JF; Ostrosky-Zeichner, L; Rex, JH; Rodriguez, JR, 2004)	0.32
" The plasma half-life of IT-101 ranges from 17 -20 h and is significantly greater than that of CPT alone (1."	( Pharmacokinetics and biodistribution of the camptothecin-polymer conjugate IT-101 in rats and tumor-bearing mice. Cheng, J; Davis, ME; Khin, KT; Schluep, T, 2006)	0.33
"The studies presented here indicate that intravenous administration of IT-101, a cyclodextrin based polymer-CPT conjugate, gives prolonged plasma half-life and enhanced distribution to tumor tissue when compared to CPT alone."	( Pharmacokinetics and biodistribution of the camptothecin-polymer conjugate IT-101 in rats and tumor-bearing mice. Cheng, J; Davis, ME; Khin, KT; Schluep, T, 2006)	0.33
"To establish RP-HPLC method for determination of plasma scutellarin concentration and study of the pharmacokinetic behavior of scutellarin in rat after ig administration of breviscapine and its beta-cyclodextrin complex (breviscapine-beta-CD)."	( [Pharmacokinetics of breviscapine and its beta-cyclodextrin complex in rats]. Cao, F; Guo, JX; Ping, QN; Zhang, HY, 2005)	0.33
" The pharmacokinetic parameters were calculated by 3P97 software."	( [Pharmacokinetics of breviscapine and its beta-cyclodextrin complex in rats]. Cao, F; Guo, JX; Ping, QN; Zhang, HY, 2005)	0.33
" The area under curve (AUC) and the peak serum concentration (Cmax) were approximately 10 times higher than those obtained with the suspension, while the time (Tmax) to reach Cmax was reduced."	( Pharmacokinetic study of a new synthetic MMP inhibitor (Ro 28-2653) after IV and oral administration of cyclodextrin solutions. Bertholet, P; Castagne, D; Chiap, P; Delattre, L; Evrard, B; Foidart, JM; Frankenne, F; Piel, G; Piette, M, 2006)	0.33
"To evaluate the aqueous humor pharmacokinetics of rufloxacin in rabbits after topical administration of different formulations, and to individuate the ones showing the best pharmacokinetic profile."	( Rufloxacin eyedrops: effect of different formulations on ocular pharmacokinetics in rabbits. Burgalassi, S; Cappello, B; Chetoni, P; Iervolino, M; Monti, D; Saettone, MF, )	0.13
" The main pharmacokinetic parameters of RUF in the aqueous humor produced by the different formulations were calculated and statistical differences were assessed."	( Rufloxacin eyedrops: effect of different formulations on ocular pharmacokinetics in rabbits. Burgalassi, S; Cappello, B; Chetoni, P; Iervolino, M; Monti, D; Saettone, MF, )	0.13
" For example, the terminal half-life (t(1/2)) of letrozole following intravenous administration in male rats was 11."	( Pharmacokinetics of letrozole in male and female rats: influence of complexation with hydroxybutenyl-beta cyclodextrin. Buchanan, CM; Buchanan, NL; Edgar, KJ; Hanley, GA; Ramsey, MG; Rice, PJ; Skotty, JS; Wempe, MF, 2007)	0.34
" The validated method was successfully applied in pharmacokinetic investigations of IBP enantiomers as well as free chiral metabolites in reference to the genetic polymorphism of CYP450 2C isoenzymes."	( Enantioselective CE method for pharmacokinetic studies on ibuprofen and its chiral metabolites with reference to genetic polymorphism. Główka, F; Karaźniewicz, M, 2007)	0.34
" Serum concentration profiles and key pharmacokinetic (PK) variables of doxycycline-h-LA were compared to the corresponding profiles and PK values obtained with an aqueous formulation of doxycycline-h administered either intramuscularly, orally or intravenously to Wistar rats."	( Pharmacokinetics of doxycycline and tissue concentrations of an experimental long-acting parenteral formulation of doxycycline in Wistar rats. Gutiérrez, L; Juarez-Rodríguez, I; Sumano, H; Vargas-Estrada, D, 2008)	0.35
"Pharmacokinetic studies in mice traditionally require one animal per time point, resulting in dosing and euthanizing a large number of animals and producing suboptimal quality of pharmacokinetic data due to inter-animal variability and dosing error."	( Improved pharmacokinetic and bioavailability support of drug discovery using serial blood sampling in mice. Hageman, W; Huebert, ND; Peng, SX; Rockafellow, BA; Skedzielewski, TM, 2009)	0.35
" In comparison with resveratrol, TMS had greater plasma exposure, longer elimination half-life and lower clearance."	( A rapid HPLC method for the quantification of 3,5,4'-trimethoxy-trans-stilbene (TMS) in rat plasma and its application in pharmacokinetic study. Ho, PC; Lin, HS, 2009)	0.35
" The clinically relevant observed pharmacokinetic parameters of inhaled aqueous solutions of voriconazole suggest that therapeutic outcomes could be benefitted through the use of inhaled voriconazole."	( Characterization and pharmacokinetic analysis of aerosolized aqueous voriconazole solution. Bosselmann, S; McConville, JT; Nelson, NA; Peters, JI; Son, YJ; Tolman, JA; Wiederhold, NP; Williams, RO, 2009)	0.35
" Both formulations showed similar pharmacokinetic profiles and could represent valuable formulations in case of emergencies, when a rapid action in the central nervous system is desirable."	( Pharmacokinetic study of a carbamazepine nanoemulsion in beagle dogs. de Araújo, BV; Kelmann, RG; Koester, LS; Kratz, JM; Kuminek, G; Ribeiro, R; Simões, CM; Teixeira, HF, 2009)	0.35
" Pharmacokinetic studies conducted in patients receiving CRRT and telavancin are needed to confirm these in vitro findings."	( Telavancin and hydroxy propyl-beta-cyclodextrin clearance during continuous renal replacement therapy: an in vitro study. Barriere, SL; Churchwell, MD; Grio, M; Mueller, B; Patel, JH; Seroogy, JD, 2009)	0.35
" Pharmacokinetic parameters of mangiferin in plasma were obtained as follows: T(max) = 7 h, C(max) = (4."	( Determination of mangiferin in rat eyes and pharmacokinetic study in plasma after oral administration of mangiferin-hydroxypropyl-beta-cyclodextrin inclusion. Cui, H; Hou, Y; Li, B; Liu, Y; Yu, X; Zhang, H, 2010)	0.36
" Pharmacokinetic parameters, including half-life, volume of distribution, clearance and extent of renal elimination of melphalan were essentially unchanged between the two formulations."	( Preclinical comparison of intravenous melphalan pharmacokinetics administered in formulations containing either (SBE)7 m-β-cyclodextrin or a co-solvent system. Charman, SA; Katneni, K; Koltun, M; McIntosh, MP; Morizzi, J; Shackleford, DM, 2010)	0.36
" Pharmacokinetic study revealed that honokiol-in-HP-β-CD-in-liposome significantly retarded the elimination and prolonged the residence time in circulating system."	( Preparation, characterization, pharmacokinetics, and bioactivity of honokiol-in-hydroxypropyl-β-cyclodextrin-in-liposome. Cai, L; Chen, L; Deng, C; Deng, L; Duan, X; Wang, X; Wei, Y; Zhang, X; Zhao, X; Zheng, H, 2011)	0.37
" time data were analyzed by a noncompartmental pharmacokinetic method."	( Pharmacokinetic study of rhizoma Curcumae oil and rhizoma Curcumae oil-β-cyclodextrin inclusion complex in pigs after oral administration. Dongping, Z; Gang, W; Haiyan, Z; Yong-Xue, S; Yongjin, L; Zhichang, L, 2012)	0.38
" To evaluate its suitability as a drug candidate, a pharmacokinetic study was carried out in Sprague-Dawley rats with the emphasis to identify the impact of aqueous solubility, dose escalation, food, and repeated dosing on its oral bioavailability."	( Preclinical pharmacokinetic evaluation of resveratrol trimethyl ether in sprague-dawley rats: the impacts of aqueous solubility, dose escalation, food and repeated dosing on oral bioavailability. Ho, PC; Lin, HS, 2011)	0.37
" Studies based on pharmacokinetics, biodistribution, and antitumor efficacy indicated that DTX/HP-SBE-β-CD had similar pharmacokinetic properties and antitumor efficacy both in vitro and in vivo as Taxotere®."	( Pharmacokinetics, efficacy, and safety evaluation of docetaxel/hydroxypropyl-sulfobutyl-β-cyclodextrin inclusion complex. Chen, C; Huang, XX; Ren, Y; Wang, H; Xu, Q; Yu, SQ; Zhou, CL; Zhu, YY, 2011)	0.37
"05) in pharmacokinetic parameters of ZER in ZER/HPβCD complex compared with ZER in CMC preparation."	( Liquid chromatography-tandem mass spectroscopic method for the determination of zerumbone in human plasma and its application to pharmacokinetics. Abdul, AB; Eid, EE; Fatah, SA; Rasedee, A; Sukari, MA; Suliman, FE, 2011)	0.37
" The present first-in-human study assessed the pharmacokinetic and pharmacodynamic effects of PM103 and its safety in 144 healthy human subjects."	( Pharmacokinetics and platelet aggregation inhibitory effects of a novel intravenous formulation of clopidogrel in humans. Adams, MP; Cooper, WD; Cushing, DJ; Kowey, PR; Machatha, S; Mosher, GL; Souney, PF; Zhang, B, 2012)	0.38
" Indomethacin ocular levels were measured by liquid chromatography mass spectrometry (LC-MS/MS), and the pharmacokinetic parameters--peak drug concentration (C(max)), time to peak value (T(max)), and area under the concentration-time curve between 0 and 240 min (AUC(0-240))--were determined."	( Ocular pharmacokinetics profile of different indomethacin topical formulations. Bucolo, C; Drago, F; Melilli, B; Piazza, C; Zurria, M, 2011)	0.37
"IND-HPMC treatment demonstrates a nonclinical ocular pharmacokinetic profile of indomethacin characterized by higher concentrations of drug in ocular tissues (4."	( Ocular pharmacokinetics profile of different indomethacin topical formulations. Bucolo, C; Drago, F; Melilli, B; Piazza, C; Zurria, M, 2011)	0.37
" To date, no information is available about the pharmacokinetic (PK) properties of visnagin."	( Nonlinear pharmacokinetics of visnagin in rats after intravenous bolus administration. Butterweck, V; Haug, KG; Hochhaus, G; Weber, B, 2012)	0.38
" As demonstrated, pharmacokinetic studies reveal that, as compared with FK506-loaded BSA nanoparticles, the FK506/DM-β-CD inclusion complex-loaded BSA nanoparticles have significant increase at T(max), t(1/2), MRT and decrease at C(max)."	( Preparation, characterization and pharmacokinetic studies of tacrolimus-dimethyl-β-cyclodextrin inclusion complex-loaded albumin nanoparticles. Fu, D; Gao, F; Gao, S; Lan, M; Sun, J; Zhao, H, 2012)	0.38
"How a drug distributes within highly compartmentalized mammalian cells can affect both the activity and pharmacokinetic behavior."	( Cationic amphiphilic drugs cause a marked expansion of apparent lysosomal volume: implications for an intracellular distribution-based drug interaction. Funk, RS; Krise, JP, 2012)	0.38
" In this study, a comparative pharmacokinetic study of 2 docetaxel parenteral solutions, SID530 and Taxotere, was carried out."	( Pharmacokinetic equivalence of Taxotere and SID530, a novel docetaxel formulation containing hydroxypropyl-beta-cyclodextrin in monkeys. Kim, EJ; Kim, TK; Lee, BY; Park, JH; Yoo, HH, 2012)	0.38
" Blood propofol followed three-compartment pharmacokinetic behavior and derived parameters were not statistically different except for elimination half-life from the CDP formulation and onset, and duration of anesthesia from the FP formulation."	( Comparative canine pharmacokinetics-pharmacodynamics of fospropofol disodium injection, propofol emulsion, and cyclodextrin-enabled propofol solution following bolus parenteral administration. McIntosh, MP; Rajewski, RA, 2012)	0.38
"One single-dose, randomized, three-way, crossover relative bioavailability study and one linearity single escalating dose, randomized, three-way cross-over pharmacokinetic study were conducted at two different clinical sites."	( Pharmacokinetics of a new diclofenac sodium formulation developed for subcutaneous and intramuscular administration. Ducharme, MP; Gugliotta, B; Müller, M; Oraha, AZ; Rusca, A; Zeitlinger, M, 2012)	0.38
" with respect to Cmax and AUC."	( Pharmacokinetics of a new diclofenac sodium formulation developed for subcutaneous and intramuscular administration. Ducharme, MP; Gugliotta, B; Müller, M; Oraha, AZ; Rusca, A; Zeitlinger, M, 2012)	0.38
" The validated method was applied in a comparative pharmacokinetic study in which two docetaxel formulations, SID530, a new parenteral formulation of docetaxel with hydroxypropyl-β-cyclodextrin (HP-β-CD), and Taxotere, were administered to rats at a dose of 5 mg/kg."	( Determination of docetaxel in rat plasma and its application in the comparative pharmacokinetics of Taxotere and SID530, a novel docetaxel formulation with hydroxypropyl-β-cyclodextrin. Kim, IS; Kim, TK; Yoo, HH, 2013)	0.39
" The research was aimed to improve solubility and reduce in vivo variability in pharmacokinetic parameters of TEL irrespective to physiological pH conditions."	( Amorphous ternary cyclodextrin nanocomposites of telmisartan for oral drug delivery: improved solubility and reduced pharmacokinetic variability. Sangwai, M; Vavia, P, 2013)	0.39
"These findings demonstrate that the combination of acetic acid and HPβCD significantly improves the solubility, pharmacokinetic profile and antitumor efficacy of ABZ."	( Complexation of albendazole with hydroxypropyl-β-cyclodextrin significantly improves its pharmacokinetic profile, cell cytotoxicity and antitumor efficacy in nude mice. Chu, SW; Ehteda, A; Galettis, P; Morris, DL; Pillai, K, 2012)	0.38
" The pharmacokinetic profiles of DFS were examined in Sprague-Dawley rats after intravenous administration (2 mg/kg)."	( Quantification of trans-2,6-difluoro-4'-N,N-dimethylaminostilbene in rat plasma: application to a pharmacokinetic study. Anderson, BD; Ho, PC; Lin, HS; Liu, C; Ong, PS; Sviripa, VM; Watt, DS; Xiang, TX, 2013)	0.39
" A pharmacokinetic model was applied to model systemic RIF concentrations and to predict the RIF concentrations in the lung epithelial lining fluid (ELF)."	( A preclinical pharmacokinetic modeling approach to the biopharmaceutical characterization of immediate and microsphere-based sustained release pulmonary formulations of rifampicin. Couet, W; Doan, TV; Gobin, P; Grégoire, N; Lamarche, I; Marchand, S; Olivier, JC, 2013)	0.39
"8 mL/min/kg) and moderate terminal elimination half-life (t(1/2λz) = 93."	( Pharmacokinetics of pterostilbene in Sprague-Dawley rats: the impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability. Ho, PC; Lin, HS; Yeo, SC, 2013)	0.39
" Study 2: Cmax for diclofenac was 2904 and 6031 ng/ml after the first IV dose of 18."	( Single-dose and multiple-dose pharmacokinetics and dose proportionality of intravenous and intramuscular HPβCD-diclofenac (Dyloject) compared with other diclofenac formulations. Carr, DB; Hamilton, DA; Lacouture, PG; Mermelstein, F; Ramaiya, A; Wright, C, 2013)	0.39
" Subsequently, a pharmacokinetic study was performed using liquid chromatography-tandem mass spectrometry."	( Preparation and pharmacokinetic study of aprepitant-sulfobutyl ether-β-cyclodextrin complex. Chen, G; Li, M; Ren, L; Wei, P; Zhou, Y, 2014)	0.4
"We investigated the pharmacokinetic behavior of orally disintegrating tablets (ODTs) containing perphenazine/hydroxypropyl-beta-cyclodextrin inclusion complex (PPZ/HP-beta-CD) in rabbits and evaluated their bioequivalence with conventional tablets."	( Pharmacokinetics of orally disintegrating tablets of perphenazine/hydroxypropyl-beta-cyclodextrin inclusion complex in rabbits. Chen, ML; Wang, L; Xiao, YY; Zeng, F; Zong, L, 2013)	0.39
" Biological investigations including pharmacokinetic studies, brain drug targeting efficiency determinations and histopathological examinations were performed on rats."	( Chitosan and cyclodextrin in intranasal microemulsion for improved brain buspirone hydrochloride pharmacokinetics in rats. Bshara, H; El-Shamy, Ael-H; Mansour, S; Osman, R, 2014)	0.4
" The Cmax was comparable after SC administration in the quadriceps or abdomen, and ~ 17% higher in the gluteus."	( Pharmacokinetics of a new subcutaneous diclofenac formulation administered to three body sites: quadriceps, gluteus, and abdomen. Cardì, F; Drago, F; Gugliotta, B; Piazza, C; Salomone, S; Vitale, DC, 2014)	0.4
" The two-compartment pharmacokinetic model described the mechanisms of how the human body handles with ingestion of NC-cyclodextrin complexes in gastrointestinal tract (GI), distribution in plasma, and their metabolism in the liver."	( Pharmacokinetic delivery and metabolizing rate of nicardipine incorporated in hydrophilic and hydrophobic cyclodextrins using two-compartment mathematical model. Förster, C; Shityakov, S, 2013)	0.39
" pharmacokinetic profile of a drug is unchanged in the presence of CD."	( The effect of intravenous sulfobutylether7 -β-cyclodextrin on the pharmacokinetics of a series of adamantane-containing compounds. Leong, NJ; Mcintosh, MP; Prankerd, RJ; Shackleford, DM, 2015)	0.42
"This prospective, open-label pharmacokinetic study enrolled patients >18 years old receiving IV voriconazole for a known or suspected invasive fungal infection while undergoing CRRT."	( Evaluation of sulfobutylether-β-cyclodextrin (SBECD) accumulation and voriconazole pharmacokinetics in critically ill patients undergoing continuous renal replacement therapy. Aquilante, CL; Fish, DN; Kiser, TH; MacLaren, R; Rower, JE; Teitelbaum, I; Wempe, MF, 2015)	0.42
" Similarly, the in vivo pharmacokinetics parameters also increased, Cmax (from 737."	( Preparation, characterization, and pharmacokinetics study of capsaicin via hydroxypropyl-beta-cyclodextrin encapsulation. Firempong, CK; Shi, F; Sun, C; Xu, X; Yu, J; Zhang, W; Zhao, Y, 2016)	0.43
" However, its volatility, instability and poor water-solubility influence its pharmacodynamic effects."	( Preparation, Characterization and Pharmacokinetic Study of Xiangfu Siwu Decoction Essential Oil/β-Cyclodextrin Inclusion Complex. Duan, J; Guo, J; Liu, P; Pan, Y; Qian, D; Xi, J; Zhang, Y; Zhu, Z, 2015)	0.42
" The pharmacokinetics of 2-n-PQ in rats showed that after an intravenous treatment of the formulation at 10mgkg(-1), the plasma drug concentrations rapidly declined bi-exponentially with a half-life of 58."	( In vitro and in vivo antileishmanial properties of a 2-n-propylquinoline hydroxypropyl β-cyclodextrin formulation and pharmacokinetics via intravenous route. Balaraman, K; Bories, C; Cojean, S; Figadère, B; Kesavan, V; Loiseau, PM; Moussa, F; Pomel, S; Vacus, J; Vieira, NC, 2015)	0.42
"To compare the pharmacokinetic parameters of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex and free evodiamine suspension in rats, and investigate the pharmacokinetic characteristics of evodiamine inclusion complex."	( [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Feng, J; Lei, TT; Liu, HM; Zhang, JQ; Zhang, X, 2016)	0.43
" The pharmacokinetic parameters of evodiamine inclusion complex and free evodiamine in rats were as follows: Cmax, 252."	( [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Feng, J; Lei, TT; Liu, HM; Zhang, JQ; Zhang, X, 2016)	0.43
" Pharmacokinetic studies after oral administration of 16-DHP-HP-β-CD at doses of 37."	( Pharmacokinetics of 16-dehydropregnenolone hydroxypropyl-β-cyclodextrin inclusion complex following peroral administration. Jia, L; Mao, M; Sun, L; Sun, Y; Wang, X; Wei, L; Zhou, H, 2017)	0.46
"29) h, peak concentration (Cmax) of (30."	( [Pharmacokinetics and Bioequiavailability of Asparaginase in Asparaginase Nanospheres]. Deng, X; Hu, XY; Li, WY; Wang, SL; Yan, ZJ; Zhang, JQ, 2016)	0.43
"AHHPs can improve the bioavailability of AAS, extending its biological half-life in rats."	( [Pharmacokinetics and Bioequiavailability of Asparaginase in Asparaginase Nanospheres]. Deng, X; Hu, XY; Li, WY; Wang, SL; Yan, ZJ; Zhang, JQ, 2016)	0.43
" Dissolution and pharmacokinetic studies indicated that the simvastatin/DMβCD complex exhibited an increased dissolution rate, rapid absorption, and improved bioavailability in rats compared to free drug."	( Preparation and characterization of simvastatin/DMβCD complex and its pharmacokinetics in rats. Fan, H; Gu, F; Ning, J; Wang, Y; Wu, C, 2018)	0.48
" The SD, ST, and SZ were selected as effective candidates to perform comparisons of liver targeting among the solution (SES), β-cyclodextrin inclusion compound (SCF-E-β-CD), liposome (SEL), and SCL of SCF-E to characterize the pharmacokinetic behaviors and liver targeting in rats."	( Pharmacokinetics and liver uptake of three Schisandra lignans in rats after oral administration of liposome encapsulating β-cyclodextrin inclusion compound of Schisandra extract. Chen, W; Ding, Z; Guo, Y; Hu, J; Jiang, Y; Xiao, J; Zhang, B; Zhang, Y, 2019)	0.51
" Pharmacokinetic (PK) studies were conducted in mice and the SBE-β-CD based formulation was compared with the Cremophor EL formulation."	( Pharmacokinetic modeling of the blood-stable camptothecin analog AR-67 in two different formulations. Adane, E; Leggas, M; Liu, X; Tang, F, 2019)	0.51
" The pharmacokinetic investigation of the releasing results demonstrated the best fitting with Korsmeyer-Peppas with diffusion exponent (n) values related to non-Fickian transport behavior suggesting a combination of erosion and diffusion mechanisms."	( Insight into the role of integrated carbohydrate polymers (starch, chitosan, and β-cyclodextrin) with mesoporous silica as carriers for ibuprofen drug; equilibrium and pharmacokinetic properties. Abukhadra, MR; El-Sherbeeny, AM; Ibrahim, KE; Nadeem, A; Refay, NM, 2020)	0.56

Excerpt	Reference	Relevance
" Because of their anionic nature and large number of acid groups, they tend to interact with cationic substances, and with other hydrophilic polymers containing alcohol groups."	( Use of beta-cyclodextrins to prevent modifications of the properties of carbopol hydrogels due to carbopol-drug interactions. Blanco-Fuente, H; Blanco-Méndez, J; Esteban-Fernández, B; Otero-Espinar, FJ, 2002)	0.31
"The enantiomeric separation of a series of basic pharmaceuticals (beta-blockers, local anesthetics, sympathomimetics) has been investigated in nonaqueous capillary electrophoresis (NACE) systems using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin (HDMS-beta-CD) in combination with potassium camphorsulfonate (camphorSO3-)."	( Enantiomeric separation of basic compounds using heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-cyclodextrin in combination with potassium camphorsulfonate in nonaqueous capillary electrophoresis: optimization by means of an experimental design. Chiap, P; Crommen, J; Dewé, W; Fillet, M; Hubert, P; Servais, AC, 2004)	0.32
" These studies indicated that lower concentrations of MβCD combined with IL-2 can preferentially induce activation and proliferation of NK cells in PBMCs."	( Lower concentrations of methyl-β-cyclodextrin combined with interleukin-2 can preferentially induce activation and proliferation of natural killer cells in human peripheral blood. Chen, Y; Li, BQ; Lü, HZ; Tang, J; Zhu, AY, 2011)	0.37
" This method is based on using gold nanoparticle (AuNP) as signal tag in laser desorption/ionization mass spectrometry (LDI-MS) analysis combined with boronic acid assisted isolation strategy."	( Mass spectrometry signal amplification for ultrasensitive glycoprotein detection using gold nanoparticle as mass tag combined with boronic acid based isolation strategy. Liu, M; Lu, H; Xu, Y; Yang, P; Zhang, L, 2013)	0.39
"A new method of hollow fiber liquid-liquid-liquid microextraction (HF-LLLME) combined with high performance liquid chromatography-ultraviolet detection (HPLC-UV) was developed for simultaneous analysis of various environmental estrogens."	( Hollow fiber liquid-liquid-liquid microextraction combined with high performance liquid chromatography-ultraviolet detection for the determination of various environmental estrogens in environmental and biological samples. Chen, B; He, M; Hu, B; Huang, Y, 2013)	0.39
" The results indicate that the ternary system of ME combination with HP-β-CD may be a promising approach for skin targeting delivery of KET."	( Synergetic skin targeting effect of hydroxypropyl-β-cyclodextrin combined with microemulsion for ketoconazole. Che, J; Guo, P; Lin, Y; Pan, W; Shao, W; Wu, C; Wu, Z; Xu, Y; Zeng, W; Zhang, G, 2015)	0.42
"A high-performance and selective adsorbent was developed for simultaneous extraction of 6 chlorobenzenes residues in soil samples by using magnetic solid phase extraction (MSPE) combined with automated SPE followed by gas chromatography-mass spectrometry (GC-MS)."	( β-cyclodextrin functionalized meso-/macroporous magnetic titanium dioxide adsorbent as extraction material combined with gas chromatography-mass spectrometry for the detection of chlorobenzenes in soil samples. Cao, Y; Chen, S; Gan, N; Pan, M; Wu, D; Zhang, J, 2015)	0.42
" This result indicates that soil washing combined with Fenton-like oxidation may be a practical approach for the remediation of PCB-contaminated soil."	( Soil washing in combination with homogeneous Fenton-like oxidation for the removal of 2,4,4'-trichlorodiphenyl from soil contaminated with capacitor oil. Dong, YH; Lin, ZR; Ma, XH; Zhao, L, 2016)	0.43
" In this study we have examined the effects of four naturally occurring polyphenols in combination with β-cyclodextrin (β-CD) on the aggregation of α-synuclein in the presence of macromolecular crowding agents."	( Polyphenols in combination with β-cyclodextrin can inhibit and disaggregate α-synuclein amyloids under cell mimicking conditions: A promising therapeutic alternative. Batra, R; Chowdhury, PK; Gautam, S; Karmakar, S; Kundu, B; Pradhan, P; Sharma, P; Singh, J, 2017)	0.46
" indicum with the assistance of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) using response surface methodology combined with various optimization algorithms, including desirability function approach, genetic algorithm, particle swarm optimization, and firefly algorithm."	( Optimization of β-Cyclodextrin-Assisted Extraction of Apigenin and Luteolin from Chrysanthemum indicum L. Using Response Surface Methodology Combined with Different Optimization Algorithms and Evaluation of Its Antioxidant Capacity. Nguyen Thu, H; Nguyen-Van, P, 2023)	0.91

Excerpt	Reference	Relevance
"The very low bioavailability of silybinin, the main constituent of silymarin, so far prevented the development of an oral pharmaceutical specialty based on this active ingredient."	( [A new inclusion complex of silibinin and beta-cyclodextrins: in vitro dissolution kinetics and in vivo absorption in comparison with traditional formulations]. Arcari, M; Brambilla, A; Brandt, A; Caponi, R; Corsi, G; Di Rella, M; Solinas, F; Wachter, WP, 1992)	0.28
" Among the three beta-CyDs, HP-beta-CyD was best at improving the rectal bioavailability of EBA in rats after single and multiple administrations of oleaginous suppositories (Witepsol H-5) containing the complexes."	( Enhanced rectal absorption and reduced local irritation of the anti-inflammatory drug ethyl 4-biphenylylacetate in rats by complexation with water-soluble beta-cyclodextrin derivatives and formulation as oleaginous suppository. Arima, H; Irie, T; Kondo, T; Uekama, K, 1992)	0.28
" In the present work, drug-bCD system or interacted products are prepared in order to screen different method of preparation in respect to the bioavailability increase (evaluated in vitro) and to the feasibility of the manufacturing process."	( [Evaluation of beta-cyclodextrins as formulated coadjuvants for improved drug solubility]. Maffione, G; Rosso, F, 1991)	0.28
" The bioavailability of an investigational drug in cynomolgus monkeys could be enhanced sevenfold by inclusion complexation with 2-HP-beta-CD."	( Effect of hydrotropic substances on the complexation of sparingly soluble drugs with cyclodextrin derivatives and the influence of cyclodextrin complexation on the pharmacokinetics of the drugs. Albers, E; Müller, BW, 1991)	0.28
" Relative bioavailability was assessed by the measurement of serum canrenone concentrations."	( Improved bioavailability from a spironolactone beta-cyclodextrin complex. Bramley, PN; Chrystyn, H; Losowsky, MS; Swallow, RD; Tuladhar, BR; York, P; Yusuff, NT, 1991)	0.28
" When used in pharmaceutical formulations, they can improve the aqueous solubility, stability, dissolution rate, bioavailability and/or local tolerance of certain drugs."	( Beta-cyclodextrins as vehicles in eye-drop formulations: an evaluation of their effects on rabbit corneal epithelium. Borgers, M; Jansen, T; Mesens, J; Xhonneux, B, 1990)	0.28
" The result also shows beta-cyclodextrin and HPMC markedly reduced the in vivo bioavailability of acetaminophen from both test formulations."	( Effect of beta-cyclodextrin on the in vitro permeation rate and in vivo rectal absorption of acetaminophen hydrogel preparations. Lin, SY; Yang, JC, 1990)	0.28
"Dipyridamole forms an inclusion complex with beta-cyclodextrin (dip-beta-CD) which shows better solubility and bioavailability than the uncomplexed compound."	( Enhancement of specific biological activity of dipyridamole by complexation with beta-cyclodextrin. Bertè, F; Fregnan, GB, 1990)	0.28
" Differences in bioavailability may have resulted from differences in experimental animal conditions."	( Nasal absorption enhancement of 17 beta-estradiol by dimethyl-beta-cyclodextrin in rabbits and rats. Deurloo, MJ; Hermens, WA; Merkus, FW; Romeyn, SG; Verhoef, JC, 1990)	0.28
" The results suggested that the use of CME-beta CD could improve the oral bioavailability of diltiazem and release the drug preferentially in the intestinal fluid but only slightly in the gastric fluid."	( O-carboxymethyl-O-ethylcyclomaltoheptaose as a delayed-release-type drug carrier: improvement of the oral bioavailability of diltiazem in the dog. Hirayama, F; Horiuchi, Y; Irie, T; Uekama, K, 1989)	0.28
" Dip-beta-CD afforded significantly shorter lag-times, higher Cmax, smaller interindividual variations of plasma concentrations and greater urinary excretion than the other two preparations, as a consequence of a better bioavailability of the former one."	( Pharmacokinetics of dipyridamole-beta-cyclodextrin complex in dogs. Anfossi, P; Fregnan, GB; Malvisi, J; Stracciari, GL, )	0.13
"This investigation was concerned with the change of the bioavailability of a drug owing to the interaction of the drug-beta-cyclodextrin complex with bile salts in rat intestinal lumen."	( Effect of the interaction of drug-beta-cyclodextrin complex with bile salts on the drug absorption from rat small intestinal lumen. Masada, M; Miyajima, K; Nadai, T; Nakanishi, K, 1989)	0.28
" The potential of these alternative formulations for increasing the ocular bioavailability of forskolin is discussed."	( Preparation and evaluation in rabbits of topical solutions containing forskolin. Burgalassi, S; Giannaccini, B; Saettone, MF, 1989)	0.28
" The enhanced rate of bioavailability of prednisolone after intramuscular administration in the form of a suspension may be due to the rapid dissolution of CyD complexes."	( Effects of beta- and gamma-cyclodextrins on the pharmacokinetic behavior of prednisolone after intravenous and intramuscular administrations to rabbits. Arimori, K; Uekama, K, 1987)	0.27
"The present investigation is concerned with an improvement of the bioavailability of cinnarizine by administering its beta-cyclodextrin complex together with another compound which competes with the beta-cyclodextrin molecule in complex formation in aqueous solution (competing agent)."	( Enhancement of bioavailability of cinnarizine from its beta-cyclodextrin complex on oral administration with DL-phenylalanine as a competing agent. Kayano, M; Machida, Y; Nagai, T; Nanba, M; Tatsuishi, K; Tokumura, T; Tsushima, Y, 1986)	0.27
" A crossover bioavailability study was performed using human subjects with lower doses of prednisolone tablets, where the plasma levels of the drug were determined by radioimmunoassay."	( Improvement of oral bioavailability of prednisolone by beta-cyclodextrin complexation in humans. Arimori, K; Fujinaga, T; Matsuo, N; Otagiri, M; Sugii, A; Tasaki, K; Uekama, K; Uemura, Y, 1983)	0.27
" The enhanced bioavailability of flurbiprofen suggests the possible utility of tri-O-methyl-beta-cyclodextrin in pharmaceutical formulation."	( Enhanced oral bioavailability of antiinflammatory drug flurbiprofen in rabbits by tri-O-methyl-beta-cyclodextrin complexation. Imai, T; Otagiri, M; Uekama, K, 1982)	0.26
"Poor oral bioavailability of three experimental compounds, 1-III, observed in animals has been attributed to the low intrinsic solubility."	( Effects of inclusion complexation on the transepithelial transport of a lipophilic substance in vitro. Chen, FJ; Cho, MJ; Huczek, DL, 1995)	0.29
" The pharmacokinetic profiles of BPAA-beta-CyD complexes have shown that DM-beta-CyD is the most effective in enhancing the bioavailability of BPAA."	( Differential effects of modified beta-cyclodextrins on pharmacological activity and bioavailability of 4-biphenylacetic acid in rats after oral administration. Campana, G; Puglisi, G; Spadaro, A; Spampinato, S; Ventura, CA, 1995)	0.29
" The effect of the coadministered SBE4-beta-CD on the miotic response of pilocarpine solutions was also compared to that of 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD) which has recently been suggested to increase ocular bioavailability of pilocarpine in rabbits."	( The effect of a modified beta-cyclodextrin, SBE4-beta-CD, on the aqueous stability and ocular absorption of pilocarpine. Järvinen, K; Järvinen, T; Stella, VJ; Thompson, DO, 1994)	0.29
" As the inclusion complex of piroxicam-beta-cyclodextrin is wettable and more water soluble, the absorption rate of the drug is increased whilst its other pharmacokinetic characteristics remain unchanged."	( Oral bioavailability of CHF1194, an inclusion complex of piroxicam and beta-cyclodextrin, in healthy subjects under single dose and steady-state conditions. Acerbi, D; Allemon, AM; Deroubaix, X; Lebacq, E; Stockis, A; Ventura, P, 1995)	0.29
" The absorption rate of piroxicam from the complex, determined using tmax, absorption rate constant (Ka) and plasma concentrations at 15 min and 30 min post-dose, is considerably faster than that for plain piroxicam."	( Supermolecular inclusion of piroxicam with beta-cyclodextrin: pharmacokinetic properties in man. Acerbi, D; Merz, PG; Rietbrock, N; Rietbrock, S; Woodcock, BG, 1993)	0.29
"Piroxicam-beta-cyclodextrin (PBC), a complex of piroxicam with beta-cyclodextrin, was developed with the aim of improving the hydrosolubility and bioavailability of piroxicam."	( Effects of piroxicam-beta-cyclodextrin on the gastrointestinal tract. Warrington, S, 1993)	0.29
" This results in an increase in the rate of absorption of the active compound and, consequently, in an earlier onset of analgesic action."	( Piroxicam-beta-cyclodextrin in the treatment of acute pain of rheumatic disease. Franchimont, P; Reginster, JY, 1993)	0.29
" N-methylation at the amide bond of thiazolylalanine suppressed the high hepatic clearance of one of the test compounds 18 which was well absorbed from the small intestine and it improved its oral bioavailability."	( Renin inhibitor: relationship between molecular structure and oral absorption. Fujioka, T; Hashimoto, N; Hayashi, K; Hirano, K; Nakamura, M; Odaguchi, K; Toyoda, T, 1994)	0.29
"To modify the release rate of nifedipine, a potent calcium channel antagonist, a double-layer tablet was designed, anticipating a more balanced oral bioavailability and a prolonged efficacy than the simple plain tablet."	( Design and in-vitro evaluation of a modified-release oral dosage form of nifedipine by hybridization of hydroxypropyl-beta-cyclodextrin and hydroxypropylcellulose. Hirayama, F; Horikawa, T; Uekama, K; Wang, Z, 1993)	0.29
"5) was selected as an appropriate modified-release formulation because it elicited almost comparable retarding effects with superior oral bioavailability compared with those of a commercially available slow-release nifedipine product."	( In-vivo and in-vitro evaluations of a modified-release oral dosage form of nifedipine by hybridization of hydroxypropyl-beta-cyclodextrin and hydroxypropylcelluloses in dogs. Hirayama, F; Uekama, K; Wang, Z, 1994)	0.29
"The bioavailability of PMEA from three oral formulations of the prodrug bis(POM)-PMEA has been evaluated in fasted male cynomolgus monkeys."	( Oral bioavailability of the antiretroviral agent 9-(2-phosphonylmethoxyethyl)adenine (PMEA) from three formulations of the prodrug bis(pivaloyloxymethyl)-PMEA in fasted male cynomolgus monkeys. Cundy, KC; Fishback, JA; Lee, ML; Lee, WA; Shaw, JP; Soike, KF; Visor, GC, 1994)	0.29
"Methodology and the results of the in vitro membrane diffusion and in vivo bioavailability studies are presented."	( Formulation of diazepam containing rectal suppositories and experiences of their biopharmaceutical study. Bácskay, I; Bálint, GS; Kata, M; Regdon, G; Sánta, A; Selmeczi, B; Szikszay, M, 1994)	0.29
" To evaluate the ability of hydroxypropyl-beta-cyclodextrins to improve ophthalmic drug bioavailability following topical administration, the miotic effect of topical solutions of pilocarpine was studied in New Zealand White rabbits."	( Beta-cyclodextrins enhance bioavailability of pilocarpine. Crosson, CE; Freedman, KA; Klein, JW, 1993)	0.29
" Without additives the nasal bioavailability of the peptide was in the order of 15 and 10% in rats and rabbits, respectively."	( Nasal administration of an ACTH(4-9) peptide analogue with dimethyl-beta-cyclodextrin as an absorption enhancer: pharmacokinetics and dynamics. Brakkee, JH; De Lannoy, LM; Gispen, WH; Merkus, FW; Romeijn, SG; Schipper, NG; Verhoef, JC; Wiegant, VM, 1993)	0.29
" The absolute bioavailability of the nasally administered insulin/DM beta CD powder was 13 +/- 4%, compared to 1 +/- 1% for both an insulin/DM beta CD liquid and an insulin/lactose powder formulation."	( Nasal insulin delivery with dimethyl-beta-cyclodextrin as an absorption enhancer in rabbits: powder more effective than liquid formulations. Merkus, FW; Romeijn, SG; Schipper, NG; Verhoef, JC, 1993)	0.29
" The rate and extent of nasal bioavailability of buserelin were remarkably increased by coadministration of oleic acid and HP-beta-CyD, compared with the sole use of the enhancer."	( Enhanced nasal delivery of luteinizing hormone releasing hormone agonist buserelin by oleic acid solubilized and stabilized in hydroxypropyl-beta-cyclodextrin. Abe, K; Irie, T; Uekama, K, 1995)	0.29
" Bioavailability of nasal formulations of progesterone/beta-cyclodextrin powders was discussed in term of delivery behavior."	( Delivery of nasal powders of beta-cyclodextrin by insufflation. Bettini, R; Caponetti, G; Catellani, PL; Colombo, P; De Ascentiis, A; Peracchia, MT; Santi, P, 1996)	0.29
" The absolute bioavailability of CBZ from the tablets was approximately 25%."	( Intravenous and oral pharmacokinetic evaluation of a 2-hydroxypropyl-beta-cyclodextrin-based formulation of carbamazepine in the dog: comparison with commercially available tablets and suspensions. Anderson, WR; Bodor, N; Brewster, ME; Cheung, B; Derendorf, H; Estes, KS; Meinsma, D; Moreno, D; Pablo, L; Pop, E; Sawchuk, R; Webb, AI, 1997)	0.3
" Bioavailability of piroxicam in plasma is higher after treatment with the inclusion product than with free piroxicam."	( Pharmacokinetic profile of piroxicam beta-cyclodextrin, in rat plasma and lymph. Bersani-Amado, CA; Kimura, E; Oga, S; Santos, SR; Sudo, LS, 1997)	0.3
"The mean (95% confidence limits) relative bioavailability for SP-COMP (compared with ALD) from steady state serum concentrations of canrenone, 6beta-hydroxyl 7alpha-thiomethyl spironolactone and 7alpha-thiomethyl spironolactone was 310."	( Improved bioavailability and clinical response in patients with chronic liver disease following the administration of a spironolactone: beta-cyclodextrin complex. Abosehmah-Albidy, AZ; Chrystyn, H; Losowsky, MS; Wong, V; York, P, 1997)	0.3
" From the values of K beta-CD:SA- = (105 +/- 15)M-1 and KDIMEB:SA- = (140 +/- 20)M-1 obtained, the bioavailability of the salicylate drug in the complexed form has been discussed."	( Binding of sodium salicylate by beta-cyclodextrin or 2,6-di-O-methyl-beta-cyclodextrin in aqueous solution. Aicart, E; Junquera, E; Peña, L, 1998)	0.3
"To evaluate the effect of food on the bioavailability of itraconazole (ITR) hydroxypropyl-beta-cyclodextrin (HP-beta-CD) solution under multiple-dose to steady-state conditions, and to determine the pharmacokinetics of ITR solution at steady state."	( Food interaction and steady-state pharmacokinetics of itraconazole oral solution in healthy volunteers. Barone, JA; Bierman, RH; Colaizzi, JL; Guarnieri, J; Hassell, AE; Jessen, L; Moskovitz, BL, )	0.13
"The bioavailability of ITR and OH-ITR is enhanced when ITR oral solution is given in the fasted state; this was true for both single and multiple dosing to steady state."	( Food interaction and steady-state pharmacokinetics of itraconazole oral solution in healthy volunteers. Barone, JA; Bierman, RH; Colaizzi, JL; Guarnieri, J; Hassell, AE; Jessen, L; Moskovitz, BL, )	0.13
" Both cyclodextrin formulations enhanced spironolactone bioavailability to a similar extent despite some deacetylation of spironolactone in the presence of SBE7."	( Water-soluble beta-cyclodextrins in paediatric oral solutions of spironolactone: preclinical evaluation of spironolactone bioavailability from solutions of beta-cyclodextrin derivatives in rats. Kaukonen, AM; Lennernäs, H; Mannermaa, JP, 1998)	0.3
" The variability of bioavailability of DM-beta-CyD complex was lower than that of Sandimmune, although the extent of bioavailability of DM-beta-CyD was only a little higher than that of Sandimmune."	( Enhanced absorption of cyclosporin A by complexation with dimethyl-beta-cyclodextrin in bile duct-cannulated and -noncannulated rats. Arima, H; Hirayama, F; Irie, T; Miyake, K; Uekama, K, 1999)	0.3
" In spite of its poor solubility, PZQ is well absorbed across the gastrointestinal tract, but large doses are required to achieve adequate concentrations at the target sites."	( Improvement of the in vitro dissolution of praziquantel by complexation with alpha-, beta- and gamma-cyclodextrins. Becket, G; Schep, LJ; Tan, MY, 1999)	0.3
" The present study showed that complexation of 1,2-dithiole-3-thiones with beta-cyclodextrin derivatives resulted in an increase in solubility, allowing intravenous formulation for bioavailability and metabolism studies and an increase in the dissolution rate of the drugs, which should be of interest for oral absorption of these lipophilic compounds."	( Improvement in solubility and dissolution rate of 1, 2-dithiole-3-thiones upon complexation with beta-cyclodextrin and its hydroxypropyl and sulfobutyl ether-7 derivatives. Bertault, M; Burgot, JL; Chevanne, F; Chollet, M; Dollo, G; Le Corre, P; Le Verge, R, 1999)	0.3
" The bioavailability of 5PDTT following administration of 5PDTT/SBE7-beta-CD complex was estimated to 41% while it was close to zero when 5PDTT was given as a micronized powder."	( Biopharmaceutics and pharmacokinetics of 5-phenyl-1, 2-dithiole-3-thione complexed with sulfobutyl ether-7-beta-cyclodextrin in rabbits. Burgot, JL; Chevanne, F; Dollo, G; Le Corre, P; Le Verge, R; Lefeuvre, C, 1999)	0.3
" The mean oral bioavailability of clomipramine was 24."	( Increased bioavailability of clomipramine after sublingual administration in rats. Lee, HS; Lee, KC; Yoo, SD; Yoon, BM, 1999)	0.3
" The toxicity was probably due to drug supersaturation, thereby increasing the bioavailability of the antimycotics."	( Cyclodextrin inclusion complexes of antimycotics intended to act in the oral cavity--drug supersaturation, toxicity on TR146 cells and release from a delivery system. Bjerregaard, S; Jacobsen, J; Pedersen, M, 1999)	0.3
" The relative bioavailability after oral administration was 8%."	( Bioavailability of intranasal formulations of dihydroergotamine. Hooymans, PM; Lohman, JJ; Merkus, FW; Ter Berg, JW; van der Kuy, PH, 1999)	0.3
" Since the bioavailability of itraconazole is reduced in these patients, a satisfactory dosing regimen remains to be defined."	( Itraconazole trough concentrations in antifungal prophylaxis with six different dosing regimens using hydroxypropyl-beta-cyclodextrin oral solution or coated-pellet capsules. Glasmacher, A; Hahn, C; Marklein, G; Molitor, E; Sauerbruch, T; Schmidt-Wolf, IG, 1999)	0.3
"The purpose of the present study was to evaluate the enhancement of tolbutamide (TBM) oral bioavailability and hypoglycaemic activity through complexation with beta-cyclodextrin (beta-CD) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD)."	( Oral bioavailability and hypoglycaemic activity of tolbutamide/cyclodextrin inclusion complexes. Fernandes, C; Teixeira, F; Veiga, F, 2000)	0.31
"The object of this study was to enhance the solubility, dissolution rate, and oral bioavailability of rutin by complexation with 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CyD)."	( Improvement of solubility and oral bioavailability of rutin by complexation with 2-hydroxypropyl-beta-cyclodextrin. Arima, H; Hirayama, F; Horikawa, T; Miyake, K; Noda, S; Sumiyoshi, H; Uekama, K; Yamamoto, M, 2000)	0.31
"The in vivo ocular bioavailability of hydrocortisone (HC) in the NZW rabbit was determined following topical administration of solutions containing HC (1%) with hydroxypropyl-beta-cyclodextrin (HP-beta-CD) alone, or containing the mucoadhesive, viscosity enhancing polymers sodium hyaluronate (0."	( Considerations in the use of hydroxypropyl-beta-cyclodextrin in the formulation of aqueous ophthalmic solutions of hydrocortisone. Bary, AR; Davies, NM; Tucker, IG, 2000)	0.31
"The objective of this study was to examine and compare how hydrophilic beta-cyclodextrin derivatives (beta-CyDs) improve the bioavailability of insulin following subcutaneous injection of insulin solution in rats."	( Improvement of subcutaneous bioavailability of insulin by sulphobutyl ether beta-cyclodextrin in rats. Arima, H; Hirayama, F; Irie, T; Tajiri, S; Tokihiro, K; Uekama, K, 2000)	0.31
" These results suggest that solid dispersions of ketorolac with HPbeta-CyD aid in faster dissolution and better bioavailability of the drug."	( Solid dispersion of hydroxypropyl beta-cyclodextrin and ketorolac: enhancement of in-vitro dissolution rates, improvement in anti-inflammatory activity and reduction in ulcerogenicity in rats. Meshram, RN; Nagarsenker, MS; Ramprakash, G, 2000)	0.31
" Piroxicam-beta-cyclodextrin (PBCD) was developed for pain indication by virtue of the increased absorption rate of piroxicam."	( Comparative population pharmacokinetic-pharmacodynamic analysis for piroxicam-beta-cyclodextrin and piroxicam. Hu, C; Miller, R; Wang, D; Zheng, J, 2000)	0.31
" In both models, only systemic absorption rate of bupivacaine was decreased upon complexation, not the quantity absorbed."	( [Biopharmaceutics of local anesthetic-cyclodextrin complexes following loco-regional administration]. Chevanne, F; Dollo, G; Fréville, JC; Le Corre, P; Leverge, R, 2000)	0.31
"We recently reported that of all hydrophilic cyclodextrin (CyD) derivatives examined, 2,6-di-O-methyl-beta-cyclodextrin (DM-beta-CyD) most significantly increased the aqueous solubility and the dissolution rate, resulting in the improvement of oral bioavailability of the immunosuppressive drug tacrolimus in rats."	( Contribution of P-glycoprotein to the enhancing effects of dimethyl-beta-cyclodextrin on oral bioavailability of tacrolimus. Arima, H; Hirayama, F; Uekama, K; Yunomae, K, 2001)	0.31
"The bioavailability and anthelmintic activity of albendazole-cyclodextrin complexes (ABZ-CDC) compared to albendazole suspensions in carboxymethylcellulose (ABZ-CMC) was assessed in a mouse model for Trichinella infections."	( Improving bioavailability and anthelmintic activity of albendazole by preparing albendazole-cyclodextrin complexes. Bolás, F; García-Rodriguez, JJ; Torrado, J, 2001)	0.31
"Terfenadine, an antihistaminic drug, has relatively low bioavailability after oral administration due to its limited solubility in water."	( Terfenadine-beta-Cyclodextrin inclusion complex with antihistaminic activity enhancement. Choi, HG; Han, JH; Kim, CK; Kim, YB; Lee, BJ; Lee, MK; Park, KM; Rhee, JD; Yong, CS, 2001)	0.31
"This study was undertaken with an objective to increase the dissolution rate and bioavailability of a poorly water soluble drug gliclazide (Gz) by complexation with beta-cyclodextrin (CD) in the presence of hydroxypropylmethylcellulose (HPMC)."	( Studies on solubility and hypoglycemic activity of gliclazide beta-cyclodextrin-hydroxypropylmethylcellulose complexes. Aggarwal, S; Mishra, B; Singh, PN, 2002)	0.31
"The low bioavailability of polychlorinated biphenyls (PCBs) in soils often results in their slow and partial aerobic biodegradation."	( Effects of randomly methylated-beta-cyclodextrins (RAMEB) on the bioavailability and aerobic biodegradation of polychlorinated biphenyls in three pristine soils spiked with a transformer oil. Ciccotosto, VF; Fava, F, 2002)	0.31
"A study was conducted to investigate whether cyclodextrins and surfactants can be used to predict polycyclic aromatic hydrocarbon (PAH) bioavailability in contaminated sediments."	( The estimation of PAH bioavailability in contaminated sediments using hydroxypropyl-beta-cyclodextrin and Triton X-100 extraction techniques. Cuypers, C; Grotenhuis, T; Pancras, T; Rulkens, W, 2002)	0.31
" Cyclodextrins (cds) have the property to form inclusion complexes with a great number of molecules and to enhance bioavailability and biological properties of these molecules."	( In vitro antiviral efficacy of the ganciclovir complexed with beta-cyclodextrin on human cytomegalovirus clinical strains. Finance, C; Le Faou, A; Nicolazzi, C; Venard, V, 2002)	0.31
"The aim of the present work was to develop a mucoadhesive controlled-release formulation of danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complex and to evaluate the feasibility of improving the bioavailability of danazol via the buccal route."	( Development and in vivo evaluation of buccal tablets prepared using danazol-sulfobutylether 7 beta-cyclodextrin (SBE 7) complexes. Adeyeye, MC; Aungst, BJ; Jain, AC, 2002)	0.31
"Solubilizers are often used to enhance the bioavailability of drugs with poor aqueous solubility."	( Common solubilizers to estimate the Caco-2 transport of poorly water-soluble drugs. Kobayashi, S; Kondo, H; Takahashi, Y; Watanabe, T; Yasuda, T; Yokohama, S, 2002)	0.31
" The oral bioavailability of acyclovir is thereby affected and reaches only 15-30%."	( Preliminary pharmacokinetic study of different preparations of acyclovir with beta-cyclodextrin. Aránguiz, T; Hernández, L; Luengo, J; Sepúlveda, J; Von Plessing, C, 2002)	0.31
"05) increase in the relative bioavailability is obtained with the solution containing the ABZ-HP-beta-CD complex as measured by ABZSO plasma levels."	( Oral bioavailability in sheep of albendazole from a suspension and from a solution containing hydroxypropyl-beta-cyclodextrin. Chiap, P; Crommen, J; Delattre, L; DeTullio, P; Evrard, B; Ghalmi, F; Losson, B; Piel, G; Van Hees, T, 2002)	0.31
"The bioremediation of aged polychlorinated biphenyl (PCB)-contaminated soils is adversely affected by the low bioavailability of the pollutants."	( Methyl-beta-cyclodextrin-enhanced solubilization and aerobic biodegradation of polychlorinated biphenyls in two aged-contaminated soils. Bertin, L; Fava, F; Fedi, S; Zannoni, D, 2003)	0.32
"Biodegradation of polycyclic aromatic hydrocarbons (PAH), such as phenanthrene, in environmental samples is often limited by low bioavailability which results from a combination of low aqueous solubility and/or high sorption."	( Application of a reverse transcription-PCR assay to monitor regulation of the catabolic nahAc gene during phenanthrene degradation. Maier, RM; Marlowe, EM; Pepper, IL; Wang, JM, 2002)	0.31
" FLT-HPBetaCyD improved oral bioavailability relative to FLT-SUSP."	( Hydroxypropyl-beta-cyclodextrin-flutamide inclusion complex. II. Oral and intravenous pharmacokinetics of flutamide in the rat. Diakur, J; Tam, YK; Wiebe, LI; Zuo, Z, )	0.13
" The drug bioavailability was considerably improved especially after the administration of the mixture of hydrophilic and hydrophobic complexes, when compared with the NC/TAbetaCD complex."	( Hydrophilic and hydrophobic cyclodextrins in a new sustained release oral formulation of nicardipine: in vitro evaluation and bioavailability studies in rabbits. Falcão, AC; Fernandes, CM; Ramos, P; Veiga, FJ, 2003)	0.32
" The objective of this study was to investigate the effect of the pulmonary route on the systemic absorption of FK224 in comparison with other administration routes, and to determine the bioavailability (BA) of FK224 following pulmonary administration in rats using various dosage forms."	( Improvement of pulmonary absorption of cyclopeptide FK224 in rats by co-formulating with beta-cyclodextrin. Ibuki, R; Kawashima, Y; Nakate, T; Ohike, A; Tokunaga, Y; Yoshida, H, 2003)	0.32
" It is suggested that ocular bioavailability of pilocarpine nitrate could be improved by the addition of HPbetaCD."	( Influence of hydroxypropyl beta-cyclodextrin on the corneal permeation of pilocarpine. Aktaş, Y; Hincal, AA; Irkeç, M; Orhan, M; Unlü, N, 2003)	0.32
"The objectives of this study were to evaluate the bioavailability of cogranulated and oven-dried ibuprofen (IBU) and beta-cyclodextrin (betaCD), in comparison to a physical mixture, and to examine the effect of endogenous bile on the bioavailability of the drug."	( Enhanced bioavailability of process-induced fast-dissolving ibuprofen cogranulated with beta-cyclodextrin. Adeyeye, MC; Ghorab, MK, 2003)	0.32
" The relative bioavailability of insulin formulations containing TDM was higher (0."	( Pulmonary absorption of insulin mediated by tetradecyl-beta-maltoside and dimethyl-beta-cyclodextrin. Ahsan, F; Hussain, A; Yang, T; Zaghloul, AA, 2003)	0.32
"To explore the use of cyclodextrins (CD) to form inclusion complexes with beta-lapachone (beta-lap) to overcome solubility and bioavailability problems previously noted with this drug."	( Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes. Beman, M; Boothman, DA; Bornmann, WG; Bruening, A; Gao, J; Nasongkla, N; Ray, D; Wiedmann, AF, 2003)	0.32
" Biologic activity and bioavailability of beta-lap inclusion complexes were investigated by in vitro cytotoxicity studies with MCF-7 cells and by in vivo lethality studies with C57Blk/6 mice (18-20 g)."	( Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes. Beman, M; Boothman, DA; Bornmann, WG; Bruening, A; Gao, J; Nasongkla, N; Ray, D; Wiedmann, AF, 2003)	0.32
" The study ascertained the utility of HP-beta-CD in enhancing the oral bioavailability of gliquidone, and points towards a strong influence of the preparation method on the physicochemical properties."	( Enhancement of dissolution and oral bioavailability of gliquidone with hydroxy propyl-beta-cyclodextrin. Chalasani, KB; Chauhan, AS; Diwan, PV; Jain, AK; Sridevi, S, 2003)	0.32
" The results indicated that the bioavailability of nitrendipine could be improved markedly by inclusion complexation, possibly due to an increased dissolution rate."	( Improvement of dissolution and bioavailability of nitrendipine by inclusion in hydroxypropyl-beta-cyclodextrin. Choi, HG; Jun, HW; Kim, DD; Yong, CS; Yoo, BK, 2003)	0.32
"In an effort to improve the bioavailability of the insoluble drug indomethacin, three complexes were prepared with indomethacin and the soluble complexing agents beta-, hydroxyethyl-beta-, and hydroxypropyl-beta-cyclodextrin."	( The physicochemical characteristics and bioavailability of indomethacin from beta-cyclodextrin, hydroxyethyl-beta-cyclodextrin, and hydroxypropyl-beta-cyclodextrin complexes. Casella, R; Jambhekar, S; Maher, T, 2004)	0.32
"To develop high bioavailability preparations without irritation for Panax notoginsenosides."	( [Studies on formulations of Panax notoginsenosides for intranasal administration]. Chen, DF; Fang, XL; Li, JC; Xu, QF, 2003)	0.32
"Saponins of Panax notoginseng (PNS) was absorbed in rabbits more when administered intranasally than through other routines, and the formulations including MCC both gave high bioavailability and low irritation."	( [Studies on formulations of Panax notoginsenosides for intranasal administration]. Chen, DF; Fang, XL; Li, JC; Xu, QF, 2003)	0.32
" We also found that the RMBCD-based formulation of acitretin improved its bioavailability and decreased the variations in various pharmacokinetic parameters."	( Biopharmaceutics of beta-cyclodextrin derivative-based formulations of acitretin in Sprague-Dawley rats. Chan, SY; Ho, PC; Lin, HS; Liu, X, 2004)	0.32
"Considering the narrow therapeutic index of digoxin and the low range between the safe and toxic serum concentrations of this drug, to evaluate the relative bioavailability of tablets and oral solution is necessary."	( Effects of 2-hydroxypropyl-beta-cyclodextrin on pharmacokinetics of digoxin in rabbits and humans. He, ZG; Li, YS; Tang, X; Zhang, RH; Zhang, TH; Zhao, C, 2004)	0.32
"The bioavailability of a carbamazepine:beta-cyclodextrin (CBZ:betaCD) complex from hydroxypropylmethylcellulose (HPMC) matrix tablets was evaluated in beagle dogs."	( Bioavailability of carbamazepine:beta-cyclodextrin complex in beagle dogs from hydroxypropylmethylcellulose matrix tablets. Bassani, VL; Bertuol, JB; Dalla Costa, T; Groch, KR; Koester, LS; Mayorga, P; Moellerke, R; Xavier, CR, 2004)	0.32
"The purpose of this research was to improve the solubility and therefore dissolution and bioavailability of triamterene, a poorly water soluble diuretic, by complexation with beta-cyclodextrin."	( Triamterene-beta-cyclodextrin systems: preparation, characterization and in vivo evaluation. Mukne, AP; Nagarsenker, MS, 2004)	0.32
"Formulations containing 5% dimethyl-beta-cyclodextrin (DMbetaCD) produced the highest increase in the bioavailability of LMWH preparations tested."	( Cyclodextrins in nasal delivery of low-molecular-weight heparins: in vivo and in vitro studies. Abbruscato, TJ; Ahsan, F; Hussain, A; Paulson, J; Yang, T, 2004)	0.32
" This system increases both the drug solubility in aqueous eye drops and the permeability of drug into the rabbit eye, by the formation of a drug-cyclodextrin inclusion complex, and so enhances the ocular bioavailability and anti-cataract effect of DSF."	( Bioavailability and anticataract effects of a topical ocular drug delivery system containing disulfiram and hydroxypropyl-beta-cyclodextrin on selenite-treated rats. Ito, Y; Li, D; Nabekura, T; Wang, S; Wu, C; Zhang, J, 2004)	0.32
" The ocular bioavailability was calculated by a transcorneal experiment of DSF in vivo."	( Bioavailability and anticataract effects of a topical ocular drug delivery system containing disulfiram and hydroxypropyl-beta-cyclodextrin on selenite-treated rats. Ito, Y; Li, D; Nabekura, T; Wang, S; Wu, C; Zhang, J, 2004)	0.32
"The formation of DSF/HPbetaCD inclusion and the addition of hydroxypropylmethylcellulose (HPMC), as a penetration enhancer, played very important roles in increasing the ocular bioavailability of DSF."	( Bioavailability and anticataract effects of a topical ocular drug delivery system containing disulfiram and hydroxypropyl-beta-cyclodextrin on selenite-treated rats. Ito, Y; Li, D; Nabekura, T; Wang, S; Wu, C; Zhang, J, 2004)	0.32
" DSF ocular bioavailability in rabbit aqueous humor exceeded those reported for the DSF ophthalmic preparation."	( Bioavailability and anticataract effects of a topical ocular drug delivery system containing disulfiram and hydroxypropyl-beta-cyclodextrin on selenite-treated rats. Ito, Y; Li, D; Nabekura, T; Wang, S; Wu, C; Zhang, J, 2004)	0.32
"To evaluate the bioavailability of nateglinide-hydroxypropyl-beta-cyclodextrin (HPCD) complex, a rapid and specific liquid chromatographic-tandem mass spectrometric method was developed and validated to determine nateglinide in rabbit serum."	( Study on the bioavailability of nateglinide-hydroxypropyl-beta-cyclodextrin complex capsule in rabbits by liquid chromatographic-tandem mass spectrometry. Chen, X; He, Z; Liu, X; Zhang, R; Zhao, C; Zhong, D, 2004)	0.32
" The oral bioavailability of Flu from Flu or Flu/beta-CD at doses of 1, 3, 10, and 30 mg/kg (as Flu) was examined in rats."	( Evaluation of the bioavailability of flurbiprofen and its beta-cyclodextrin inclusion complex in four different doses upon oral administration to rats. Machida, Y; Muraoka, A; Tokumura, T, 2004)	0.32
" The in vivo delivery of CF by electroporation in mice demonstrated the potential of HPCD for sustaining the transdermal absorption rate of hydrophilic molecules."	( Cyclodextrin enhanced transdermal delivery of piroxicam and carboxyfluorescein by electroporation. Hui, SW; Murthy, SN; Sen, A; Zhao, YL, 2004)	0.32
" To date, these studies have only considered bioavailability in a single soil type."	( Non-exhaustive extraction techniques (NEETs) for the prediction of naphthalene mineralisation in soil. Paton, GI; Patterson, CJ; Semple, KT, 2004)	0.32
"Solubility and bioavailability of poorly water-soluble drugs have been improved by the preparation as cyclodextrin inclusion complexes."	( [Physical and chemical characterization of allantoin-beta-cyclodextrin inclusion complex]. Gafiţanu, C; Macocinschi, D; Popescu, C; Singurel, G, )	0.13
" The effect of beta-CD on the bioavailability of meloxicam was also investigated in human volunteers using a balanced 2-way crossover study."	( Tablet formulation containing meloxicam and beta-cyclodextrin: mechanical characterization and bioavailability evaluation. Abdel-Salam, HM; El-Sayad, MA; Ghorab, MM; Mekhel, MM, 2004)	0.32
" The bioavailability of drug when administered as SD was evaluated in humans."	( Formulation studies and in vivo evaluation of a flurbiprofen-hydroxypropyl beta-cyclodextrin system. Govindarajan, R; Nagarsenker, MS, 2005)	0.33
" Being sparingly soluble and chemically unstable in aqueous intestinal fluids, quercetin is poorly absorbed orally."	( Physicochemical and structural characterization of quercetin-beta-cyclodextrin complexes. Chow, AH; Chow, MS; Haworth, IS; Zheng, Y; Zuo, Z, 2005)	0.33
" However, both binary and ternary approaches were considered suitable techniques to improve the release rate and potentially the in vivo bioavailability of poorly soluble drugs that had previously exhibited slow or incomplete release from SR beads."	( Effect of SBE7-beta-cyclodextrin complexation on carbamazepine release from sustained release beads. Macrae, RJ; Smith, JS; Snowden, MJ, 2005)	0.33
" The absolute bioavailability (F) of THC decreased in the following order: sublingual THC/RM-beta-CD solution (F = 12."	( Effects of RM-beta-CD on sublingual bioavailability of Delta9-tetrahydrocannabinol in rabbits. Jarho, P; Järvinen, K; Järvinen, T; Mannila, J; Tarvainen, M, 2005)	0.33
"It is well known that the limited aqueous solubilities of polycyclic aromatic hydrocarbons (PAH) often reduce their bioavailability to bacterial populations."	( Influence of hydroxypropyl-beta-cyclodextrin (HPCD) on the bioavailability and biodegradation of pyrene. Brusseau, ML; Maier, RM; Wang, JM, 2005)	0.33
"Cyclodextrins, especially random methylated betaCD (RAMEB) and hydroxypropyl betaCD (HPbetaCD), are becoming common enhancing additives in the bioremediation of soils formerly contaminated by hydrocarbons and/or other poorly bioavailable organic pollutants."	( Biodegradation of cyclodextrins in soil. Csabai, K; De Wilde, B; Fenyvesi, E; Gruiz, K; Leitgib, L; Szaniszlo, N; Verstichel, S, 2005)	0.33
"The bioavailability of Delta(9)-tetrahydrocannabinol (THC) was determined after its sublingual administration as solid THC/beta-cyclodextrin (THC/beta-CD) complex, and was compared to oral administration of ethanolic THC, in rabbits."	( Sublingual administration of Delta9-tetrahydrocannabinol/beta-cyclodextrin complex increases the bioavailability of Delta9-tetrahydrocannabinol in rabbits. Jarho, P; Järvinen, K; Järvinen, T; Mannila, J; Tervonen, J, 2006)	0.33
" The use of cyclodextrins to improve the solubility and bioavailability of poorly soluble drugs has however, rekindled an interest in acetazolamide (ACZ), because its poor solubility is one of the major factor responsible for its failure to show topical effectiveness."	( Development of topically effective formulations of acetazolamide using HP-beta-CD-polymer co-complexes. Aggarwal, D; Kapil, M; Kaur, IP; Smitha, R, 2004)	0.32
"The poor bioavailability and therapeutic response exhibited by conventional ophthalmic solutions due to rapid precorneal elimination of the drug may be overcome by the use of a gel system."	( Preparation and evaluation of sustained ophthalmic gel of enoxacin. Li, J; Liu, Z; Nie, S; Pan, W; Yang, X; Zhang, L, 2005)	0.33
" By comparing the AUC0-infinity of BG between oral dosing, the relative bioavailability of Ba/HP-beta-CD co-lyophilized product to free Ba was 165."	( Preparation, characterization and in vivo evaluation of formulation of baicalein with hydroxypropyl-beta-cyclodextrin. Gao, J; Jin, Y; Liu, J; Qiu, L, 2006)	0.33
" In vivo studies revealed that HP-beta-CyD markedly increases the bioavailability of FPFS-410 after oral administration in dogs."	( Improvement of solubility and oral bioavailability of 2-(N-cyanoimino)-5-[(E)-4-styrylbenzylidene]-4-oxothiazolidine (FPFS-410) with antidiabetic and lipid-lowering activities in dogs by 2-hydroxypropyl-beta-cyclodextrin. Arima, H; Hara, T; Hirayama, F; Uekama, K; Yamaguchi, Y, 2006)	0.33
" The aim of this study is to demonstrate that an increase in Ro 28-2653 solubility, via ternary complex formation, can lead to an increase in the oral bioavailability of this drug."	( Pharmacokinetic study of a new synthetic MMP inhibitor (Ro 28-2653) after IV and oral administration of cyclodextrin solutions. Bertholet, P; Castagne, D; Chiap, P; Delattre, L; Evrard, B; Foidart, JM; Frankenne, F; Piel, G; Piette, M, 2006)	0.33
" Overall, a single HPCD-extraction technique proved accurate and reproducible for the estimation of PAH bioavailability from soil."	( Further validation of the HPCD-technique for the evaluation of PAH microbial availability in soil. Clasper, PJ; Doick, KJ; Semple, KT; Urmann, K, 2006)	0.33
" The complexation of permethrin with beta-CD significantly improved the bioavailability of permethrin and, therefore, increased the bioactivity."	( Bioactive permethrin/beta-cyclodextrin inclusion complex. Gao, D; Wang, HB; Yang, GF; Yang, WC; Zhan, CG, 2006)	0.33
"In an effort to improve the bioavailability (BA) of the insoluble compound 20-O-(beta-d-glucopyranosyl)-20(S)-protopanaxadiol (IH901), we prepared beta-cyclodextrin (betaCD) and hydroxypropyl-beta-cyclodextrin (HPbetaCD) inclusion complexes containing IH901."	( Physicochemical characteristics and bioavailability of a novel intestinal metabolite of ginseng saponin (IH901) complexed with beta-cyclodextrin. Chung, YB; Han, JY; Kwon, OS; Lee, PS; Song, S; Song, TW; Sung, JH, 2006)	0.33
" These results suggest that it may be difficult to develop a chemical method that is capable of mimicking biological uptake, and thus estimating the bioavailability of PAHs."	( Comparison of techniques for estimating PAH bioavailability: uptake in Eisenia fetida, passive samplers and leaching using various solvents and additives. Andersson, PL; Bergknut, M; Haglund, P; Lundstedt, S; Sehlin, E; Tysklind, M, 2007)	0.34
"The effect of bile acids on bioavailability of FPFS-410 (2-(N-Cyanoimino)-5-{(E)-4-styrylbenzylidene}-4-oxothiazolidine) after oral administration of the drug and its 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CyD) complex was investigated."	( Enhanced bioavailability of a new thiazolidine derivative FPFS-410, an antidiabetic and lipid-lowering drug, after oral administration of its hydroxypropyl-beta-cyclodextrin complex to bile duct-cannulated rats. Arima, H; Hara, T; Hirayama, F; Uekama, K, 2006)	0.33
" The ABZSO active metabolite was analysed to determine the bioavailability of albendazole."	( 2-Hydroxypropyl-beta-cyclodextrin improves the effectiveness of albendazole against encapsulated larvae of Trichinella spiralis in a murine model. Casulli, A; Gallinella, B; Morales, MA; Pozio, E; Turchetto, L, 2006)	0.33
"These data suggest that HP-betaCD increases the bioavailability and consequently the effectiveness of albendazole against encapsulated Trichinella larvae."	( 2-Hydroxypropyl-beta-cyclodextrin improves the effectiveness of albendazole against encapsulated larvae of Trichinella spiralis in a murine model. Casulli, A; Gallinella, B; Morales, MA; Pozio, E; Turchetto, L, 2006)	0.33
" The moisture absorption rate of the beta-CD inclusion compound was determined in different humidity and Q10 was used to predict its."	( [Evaluation of cyclodextrin inclusion of the volatile components in compound traditional Chinese medicine]. Chen, ZL; Yi, YK, 2006)	0.33
" These include improved water solubility of lipophilic drug molecules, increased chemical stability, as well as enhanced bioavailability and absorption rate."	( Cyclodextrin-induced apoptosis in human keratinocytes is caspase-8 dependent and accompanied by mitochondrial cytochrome c release. Elsner, P; Hipler, UC; Radestock, A; Schönfelder, U, 2006)	0.33
"Oral and intravenous administration of tamoxifen base and tamoxifen citrate formulated with hydroxybutenyl-beta-cyclodextrin (HBenBCD) to Sprague-Dawley rats significantly increased the oral bioavailability of tamoxifen relative to that of parent drug (no HBenBCD)."	( Pharmacokinetics of tamoxifen after intravenous and oral dosing of tamoxifen-hydroxybutenyl-beta-cyclodextrin formulations. Buchanan, CM; Buchanan, NL; Edgar, KJ; Little, JL; Malcolm, MO; Ruble, KM; Wacher, VJ; Wempe, MF, 2007)	0.34
" This improved physicochemical behavior of ternary complex with the novel inclusion of a polyhydroxy base translated into an enhanced oral bioavailability of DRF-4367 compared with either uncomplexed drug or nanosuspension."	( Bioavailability enhancement of poorly water soluble and weakly acidic new chemical entity with 2-hydroxy propyl-beta-cyclodextrin: selection of meglumine, a polyhydroxy base, as a novel ternary component. Basavaraj, S; Kumar Singh, S; Ramesh, M; Shantha Kumar, TR; Sihorkar, V; Srinivas, NR; Sundaramurthi, P; Venkatesh, P, 2006)	0.33
" Pharmacokinetic testing in rats confirmed the improved drug bioavailability and demonstrated an in vitro-in vivo correlation."	( In vitro formulation optimization of intranasal galantamine leading to enhanced bioavailability and reduced emetic response in vivo. Brandt, GC; Costantino, HR; Foerder, CA; Leonard, AK; Quay, SC; Sileno, AP, 2007)	0.34
"Cyclodextrins are known to be good solubility enhancers for several drugs, improving bioavailability when incorporated in pharmaceutical formulations."	( Interaction of omeprazole with a methylated derivative of beta-cyclodextrin: phase solubility, NMR spectroscopy and molecular simulation. Carvalho, RA; Figueiras, A; Pais, AA; Sarraguça, JM; Veiga, FJ, 2007)	0.34
" These results demonstrate that the Carbopol 980NF/HPMC E4M can be a viable alternative to conventional puerarin eye drops to enhance ocular bioavailability and patient compliance."	( Preparation and evaluation of a Carbopol/HPMC-based in situ gelling ophthalmic system for puerarin. Chen, W; Hou, S; Huang, C; Li, W; Qi, H; Su, C; Wu, C, 2007)	0.34
" Hence, SFS is a potential means to simplify the present non-exhaustive hydroxypropyl-beta-cyclodextrin (HPCD)-based extraction technique for the evaluation of PAH bioavailability in soil."	( Rapid quantification of polycyclic aromatic hydrocarbons in hydroxypropyl-beta-cyclodextrin (HPCD) soil extracts by synchronous fluorescence spectroscopy (SFS). Broderick, J; Hua, G; Killham, K; Semple, KT; Singleton, I, 2007)	0.34
" To improve the oral bioavailability of clotrimazole, the inclusion compound of clotrimazole with beta-cyclodextrin was prepared by spray-drying method and characterized by phase solubility, differential scanning calorimetry and dissolution."	( Enhanced bioavailability of poorly water-soluble clotrimazole by inclusion with beta-cyclodextrin. Choi, HG; Kim, JA; Piao, MG; Prabagar, B; Rhee, JD; Woo, JS; Yong, CS; Yoo, BK, 2007)	0.34
" These results suggest that the oral bioavailability of VP was significantly improved by both multicomponent complexation and controlled release delivery strategies."	( Cyclodextrin multicomponent complexation and controlled release delivery strategies to optimize the oral bioavailability of vinpocetine. Falcão, AC; Ferreira, DC; Patrício, JA; Ribeiro, LS; Veiga, FJ, 2007)	0.34
"The low bioavailability and short half-life of metformin hydrochloride (MH) make the development of sustained-release forms desirable."	( Sustained-release matrix tablets of metformin hydrochloride in combination with triacetyl-beta-cyclodextrin. Cirri, M; Corti, G; Maestrelli, F; Mennini, N; Mura, P, 2008)	0.35
"The main objective of this study was to improve the inclusion formation between itraconazole and beta-cyclodextrin and thus enhance dissolution amount and bioavailability characteristics of itraconazole."	( Enhancement of dissolution amount and in vivo bioavailability of itraconazole by complexation with beta-cyclodextrin using supercritical carbon dioxide. Al-Marzouqi, AH; Hamza, AA; Hassan, HA; Jobe, B; Ramadan, GA, 2007)	0.34
"4 h in female) and increased absolute oral bioavailability (46 +/- 2 vs 38 +/- 3 in male, 101 +/- 3 vs 95 +/- 2 in female)."	( Pharmacokinetics of letrozole in male and female rats: influence of complexation with hydroxybutenyl-beta cyclodextrin. Buchanan, CM; Buchanan, NL; Edgar, KJ; Hanley, GA; Ramsey, MG; Rice, PJ; Skotty, JS; Wempe, MF, 2007)	0.34
" Hydroxybutenyl-beta-cyclodextrin (HBenBCD) is a novel solubility enhancer previously demonstrated to increase the oral bioavailability of tamoxifen, letrozole, and itraconazole."	( Pharmacokinetics of raloxifene in male Wistar-Hannover rats: influence of complexation with hydroxybutenyl-beta-cyclodextrin. Buchanan, CM; Buchanan, NL; Edgar, KJ; Ramsey, MG; Ruble, KM; Wacher, VJ; Wempe, MF, 2008)	0.35
" This unexpected behaviour was attributed, in part, to the fact that the heating of equimolar mixture of MA and beta-CD (first step of preparation of MA/beta-CD composition) induced the depolymerization of MA from high-molecular weight Sb complexes into 1:1 Sb-meglumine complex, resulting in an enhanced oral bioavailability of Sb."	( Enhanced oral delivery of antimony from meglumine antimoniate/beta-cyclodextrin nanoassemblies. Bahia, AP; da Silva, JB; de Melo, AL; Demicheli, C; Frézard, F; Le Moyec, L; Martins, PS; Pimenta, AM; Salerno, M, 2008)	0.35
"The purpose of this investigation was to study the influences of absorption enhancers in increasing oral bioavailability of Ganciclovir (GAN) by assessing the transepithelial permeation across cell monolayers in vitro and bioavailability in rats in vivo."	( Modulation of ganciclovir intestinal absorption in presence of absorption enhancers. Bagchi, T; Jogani, V; Mishra, AK; Mishra, P; Misra, A; Shah, P, 2007)	0.34
"Paclitaxel is a potent anticancer agent with limited bioavailability due to side-effects associated with solubilizer used in its commercial formulation and the tendency of the drug to precipitate in aqueous media."	( Safety and efficacy of amphiphilic beta-cyclodextrin nanoparticles for paclitaxel delivery. Bilensoy, E; Doğan, AL; Gürkaynak, O; Hincal, AA, 2008)	0.35
" When administered as oral solutions, the itraconazole:HBenBCD formulation provided higher oral bioavailability than the Sporanox oral solution."	( Pharmacokinetics of itraconazole after intravenous and oral dosing of itraconazole-cyclodextrin formulations. Buchanan, CM; Buchanan, NL; Edgar, KJ; Klein, S; Little, JL; Ramsey, MG; Ruble, KM; Wacher, VJ; Wempe, MF, 2007)	0.34
" Furthermore, in-vivo study revealed that the bioavailability of VIN after oral administration to rabbits (n=6) was significantly improved by VIN/HP-beta-CD+CA inclusion complex."	( In vitro and in vivo studies on the complexes of vinpocetine with hydroxypropyl-beta-cyclodextrin. Fan, X; Nie, S; Pan, W; Peng, Y; Wang, C; Yang, X, 2007)	0.34
"In order to improve the solubility and bioavailability of a soy isoflavone extract (IFE), inclusion complexes (IFE-beta-CD) of the isoflavone extract with beta-cyclodextrin (beta-CD) were prepared and studied for their solubility and bioavailability."	( Enhanced bioavailability of soy isoflavones by complexation with beta-cyclodextrin in rats. Cho, NS; Chung, CB; Hwang, YI; Kim, DC; Kim, KH; Kim, TH; Kim, YH; Lee, SH; Yu, HJ, 2007)	0.34
" Saquinavir oral bioavailability in rats obtained from saquinavir mesylate capsules (2."	( Pharmacokinetics of saquinavir after intravenous and oral dosing of saquinavir: hydroxybutenyl-beta-cyclodextrin formulations. Buchanan, CM; Buchanan, NL; Edgar, KJ; Little, JL; Ramsey, MG; Ruble, KM; Wacher, VJ; Wempe, MF, 2008)	0.35
" The oral bioavailability and hepatic toxicity of clotrimazole were compared with its beta-cyclodextrin inclusion form which was prepared by the spray-drying method."	( The effect of beta-cyclodextrin complexation on the bioavailability and hepatotoxicity of clotrimazole. Choi, HG; Kim, JA; Li, DX; Lyoo, WS; Park, BC; Prabagar, B; Rhee, JD; Woo, JS; Yi, SJ; Yong, CS; Yoo, BK, 2007)	0.34
" The study was conducted to investigate the relative bioavailability and pharmacokinetic parameters of EE and drsp after oral administration of EE-betadex clathrate/drsp."	( Novel ethinyl estradiol-beta-cyclodextrin clathrate formulation does not influence the relative bioavailability of ethinyl estradiol or coadministered drospirenone. Benda, N; Blode, H; Schürmann, R, 2008)	0.35
"The relative bioavailability of EE and drsp after EE-betadex clathrate/drsp tablet administration was comparable with that achieved with the EE/drsp tablet (107% and 101%, respectively)."	( Novel ethinyl estradiol-beta-cyclodextrin clathrate formulation does not influence the relative bioavailability of ethinyl estradiol or coadministered drospirenone. Benda, N; Blode, H; Schürmann, R, 2008)	0.35
"The betadex clathrate formulation of EE, when combined with DRSP, does not affect the pharmacokinetics and relative bioavailability of either EE or drsp."	( Novel ethinyl estradiol-beta-cyclodextrin clathrate formulation does not influence the relative bioavailability of ethinyl estradiol or coadministered drospirenone. Benda, N; Blode, H; Schürmann, R, 2008)	0.35
" After nasal administration in rats the bioavailability of rHV2 with or without various enhancers was compared."	( [Promoting mechanism of enhancers and transport pathway of large hydrophilic molecular across nasal epithelium studied by ESR and CLSM technologies]. Chen, MX; Jiang, H; Sun, MJ; Wang, Q; Wang, XL; Yang, J; Zhang, Q; Zhang, YJ, 2007)	0.34
" Since thalidomide exhibits low oral bioavailability due to limitations in solubility, inclusion complexation using sulfobutyl ether-7 beta-cyclodextrin was used to improve the delivery of thalidomide."	( Molecular encapsulation of thalidomide with sulfobutyl ether-7 beta-cyclodextrin for immediate release property: enhanced in vivo antitumor and antiangiogenesis efficacy in mice. Juvekar, A; Kale, R; Saraf, M; Tayade, P, 2008)	0.35
" The bioavailability of cryptotanshinone in rats was (6."	( Pharmacokinetic characterization of hydroxylpropyl-beta-cyclodextrin-included complex of cryptotanshinone, an investigational cardiovascular drug purified from Danshen (Salvia miltiorrhiza). Bi, HC; Chen, X; Gu, LQ; Huang, M; Huang, ZY; Liu, PQ; Pan, Y; Zhao, LZ; Zhong, GP; Zhou, SF; Zuo, Z, 2008)	0.35
" Significantly improved permeation of acyclovir in the presence of selected combinations of absorption enhancers may be used as a viable approach in overcoming the problem of limited oral bioavailability of acyclovir."	( In vitro assessment of acyclovir permeation across cell monolayers in the presence of absorption enhancers. Bagchi, T; Jogani, V; Mishra, AK; Mishra, P; Misra, A; Shah, P, 2008)	0.35
" In vivo studies showed the absolute bioavailability of 25."	( Effect of dimethyl-beta-cyclodextrin concentrations on the pulmonary delivery of recombinant human growth hormone dry powder in rats. Esmaily, H; Gilani, K; Jalalipour, M; Najafabadi, AR; Tajerzadeh, H, 2008)	0.35
" Improvement of the aqueous solubility is expected to improve the bioavailability of the drug in oral administration."	( UV-vis and FTIR-ATR characterization of 9-fluorenon-2-carboxyester/(2-hydroxypropyl)-beta-cyclodextrin inclusion complex. Calabrò, ML; Cannavà, C; Crupi, V; Ficarra, P; Ficarra, R; Guardo, M; Maccari, R; Majolino, D; Ottanà, R; Stancanelli, R; Venuti, V, 2008)	0.35
" Cyclodextrin complexes increased MPZ bioavailability at the skin surface and PMbetaCD was also able to extract cutaneous fatty acids."	( Percutaneous absorption of metopimazine and effect of cyclodextrins. Eric, M; Frédéric, B; Malika, LS; Marie, H; Mohamed, S; Philippe, A, 2008)	0.35
"The bioavailability of a novel water-soluble inclusion complex of CoQ10, prepared in our laboratory was determined and compared with the bioavailability of commercially available oil-based form of CoQ10."	( Bioavailability of water-soluble CoQ10 in beagle dogs. Butinar, J; Fir, MM; Krizman, M; Lukanc, B; Milivojevic, L; Prosek, M; Smidovnik, A, 2008)	0.35
" The relative bioavailability was evaluated by comparing area under the plasma concentration-time curve (AUC) of the pure CLM with that of its cyclodextrin-citric acid ternary complexes those were filled into hard gelatin capsules."	( Bioavailability of clarithromycin cyclodextrin ternary complexes upon oral administration to healthy beagle dogs. Chen, X; Li, S; Zhang, X; Zhong, D; Zou, M, 2008)	0.35
" RM-beta-CD significantly increased the maximal plasma concentration of orally administered resveratrol, but, it did not increase the oral bioavailability in comparison with the CMC suspension."	( The impact of aqueous solubility and dose on the pharmacokinetic profiles of resveratrol. Das, S; Ho, PC; Lin, HS; Ng, KY, 2008)	0.35
" Further, dose manipulation (up to 50 mg kg(-1)) did not have a significant impact on the oral bioavailability of resveratrol."	( The impact of aqueous solubility and dose on the pharmacokinetic profiles of resveratrol. Das, S; Ho, PC; Lin, HS; Ng, KY, 2008)	0.35
" Due to its insolubility in water, the enrichment of most food products is not easily achievable and its in vivo bioavailability is known to be poor."	( Relative bioavailability of two forms of a novel water-soluble coenzyme Q10. Fir, M; Pravst, I; Prosek, M; Smidovnik, A; Walczak, J; Zmitek, J; Zmitek, K, 2008)	0.35
"The study revealed that the absorption and bioavailability of CoQ10 in the novel formulations are significantly increased, probably due to the enhanced water solubility."	( Relative bioavailability of two forms of a novel water-soluble coenzyme Q10. Fir, M; Pravst, I; Prosek, M; Smidovnik, A; Walczak, J; Zmitek, J; Zmitek, K, 2008)	0.35
" Doxycycline-h-LA showed outstanding bioavailability (951% or 477% if a correction formula is considered), as compared to the one obtained with an aqueous formulation (106-82%, respectively)."	( Pharmacokinetics of doxycycline and tissue concentrations of an experimental long-acting parenteral formulation of doxycycline in Wistar rats. Gutiérrez, L; Juarez-Rodríguez, I; Sumano, H; Vargas-Estrada, D, 2008)	0.35
"The aim of this study was to develop an aqueous ketoconazole (KET) eye drop in order to increase the corneal permeability and improve ocular bioavailability following topical application."	( Ocular pharmacokinetics of topically-applied ketoconazole solution containing hydroxypropyl beta-cyclodextrin to rabbits. Gao, C; Wang, L; Xia, H; Zhang, J; Zhang, L, 2008)	0.35
" The KET-CD produced an over eightfold bioavailability (AUC(0-120), area under the concentration-time curve between 0 and 120 min) increase in aqueous humor over the KET-SP."	( Ocular pharmacokinetics of topically-applied ketoconazole solution containing hydroxypropyl beta-cyclodextrin to rabbits. Gao, C; Wang, L; Xia, H; Zhang, J; Zhang, L, 2008)	0.35
" The absolute bioavailability of progesterone from nasal gels in rabbits was studied by estimating the serum progesterone level by competitive solid-phase enzyme immunoassay in comparison to intravenous injection."	( Carbopol-based gels for nasal delivery of progesterone. Ilavarasan, R; Narayanan, N; Rathnam, G, 2008)	0.35
" However, its oral therapy is encountered with bioavailability problems due to its poor solubility leading to irreproducible clinical response, in addition to adverse effects like dizziness and gastric disturbances."	( Design and evaluation of chitosan films for transdermal delivery of glimepiride. Ammar, HO; El-Nahhas, SA; Elmotasem, H; Salama, HA, 2008)	0.35
" In conclusion, our results show that the new complex prepared by inclusion of dioclein in beta-CD improves the hypotensive effect of the flavonoid by increasing its bioavailability and enables dioclein to be effective after oral administration."	( Complexation with beta-cyclodextrin confers oral activity on the flavonoid dioclein. Cortes, SF; De Sousa, FB; Lemos, VS; Lula, IS; Rezende, BA; Schmitt, M; Sinisterra, RD, 2009)	0.35
"Chemical methods to assess bioavailability in soil and sediment often use synthetic polymers that mimic uptake of organic compounds in organisms or microbial degradation."	( Nonexhaustive beta-cyclodextrin extraction as a chemical tool to estimate bioavailability of hydrophobic pesticides for earthworms. Hartnik, T; Hermens, JL; Jensen, J, 2008)	0.35
"Complexation with HBenBCD may be an effective way to increase the bioavailability of glyburide."	( Improving glyburide solubility and dissolution by complexation with hydroxybutenyl-beta-cyclodextrin. Buchanan, CM; Buchanan, NL; Edgar, KJ; Klein, S; Lambert, JL; Ramsey, MG; Wempe, MF; Zoeller, T, 2009)	0.35
"P-glycoprotein (P-gp) located in the apicalmembranes of intestinal absorptive cells is an energy-dependent efflux pump which can reduce the bioavailability of a wide range of substrate drugs."	( [Advances in the study of excipient inhibitors of intestinal P-glycoprotein]. Huang, JG; Li, G; Si, LQ; Yan, F, 2008)	0.35
"Recombinant human growth hormone (rhGH) therapy for short stature must be administered as a daily injection because of its poor bioavailability and short half-life."	( Development of a sustained-release recombinant human growth hormone formulation. Choi, MK; Kang, SH; Kim, BM; Kim, TH; Kim, YJ; Kwak, HH; Lee, GI; Shim, CK; Shim, WS; Son, MK; Yang, HC, 2009)	0.35
"1-fold bioavailability (AUC(0-120), area under the concentration time curve between 0 and 120 min) increase in aqueous humor compared to the Bai-SP."	( Ocular pharmacokinetics and availability of topically applied baicalein in rabbits. Wang, L; Xia, H; Zhang, J; Zhang, L, 2009)	0.35
" Over the last decade regulators have directed concerted effort towards rationalization of risk-based contaminated land policies recognizing bioavailability and bioaccessibility as concepts to be incorporated into risk assessments."	( Beyond contaminated land assessment: on costs and benefits of bioaccessibility prediction. Latawiec, AE; Reid, BJ, 2009)	0.35
"The purpose of this study was to find out whether nasal application of buspirone could increase its bioavailability and directly transport the drug from nose to brain."	( Brain targeting studies on buspirone hydrochloride after intranasal administration of mucoadhesive formulation in rats. Gaikwad, R; Khan, S; Patil, K; Yeole, P, 2009)	0.35
"The nasal Bus-chitosan formulation improved the absolute bioavailability to 61% and the plasma concentration peaked at 30 min whereas the peak for nasal Bus-plain formulation was 60 min."	( Brain targeting studies on buspirone hydrochloride after intranasal administration of mucoadhesive formulation in rats. Gaikwad, R; Khan, S; Patil, K; Yeole, P, 2009)	0.35
"In order to enhance the ocular bioavailability of acetazolamide (ACZ), a multicomponent complex with hydroxypropyl-ss-cyclodextrin (HP-ss-CD) and triethanolamine (TEA) was prepared to be applied topically."	( An efficient ternary complex of acetazolamide with HP-ss-CD and TEA for topical ocular administration. Allemandi, DA; Granero, GE; Longhi, MR; Palma, SD; Quinteros, D; Tartara, LI, 2009)	0.35
"Improvement of the oral bioavailability of flurbiprofen (Flu) after oral administration of flurbiprofen/beta-cyclodextrin inclusion complex (Flu/beta-CD) by the action of cinnarizine (CN) was investigated."	( Improvement of oral bioavailability of flurbiprofen from flurbiprofen/beta-cyclodextrin inclusion complex by action of cinnarizine. Machida, Y; Muraoka, A; Tokumura, T, 2009)	0.35
"The study was designed to investigate the effect of cyclodextrins (CDs) on the solubility, dissolution rate, and bioavailability of cilostazol by forming inclusion complexes."	( Enhancement of oral bioavailability of cilostazol by forming its inclusion complexes. Patel, SG; Rajput, SJ, 2009)	0.35
" The developed floating tablets of Silymarin may be used in clinic for prolonged drug release for at least 24 h, thereby improving the bioavailability and patient compliance."	( Preparation and evaluation of gastroretentive floating tablets of Silymarin. Garg, R; Gupta, GD, 2009)	0.35
" The absorption rate constants (Ka) or apparent permeability coefficients (Papp) of SMESC showed duodenum > jejunum > colon = ileum."	( [In situ absorption of self-microemulsifying soft capsule of volatile oil from rhizome of ligusticum chuanxiong in rats' intestine]. Cai, Q; Huang, YP; Li, Y, 2009)	0.35
" Such host-guest complexes were investigated in view of their potential use as new therapeutic formulations, designed to increase the bioavailability and/or to decrease the systemic toxicity of proparacaine in anesthesia procedures."	( Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied (1)H-NMR approaches. Arantes, LM; de Paula, E; Fernandes, SA; Marsaioli, AJ; Scarelli, C, 2009)	0.35
"87-fold increase in bioavailability of NOS upon complexation in the beta-CD inclusion complex state as compared to free NOS."	( Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics. Aneja, R; Bharatam, PV; Chandra, R; Dhiman, N; Katyal, A; Madan, J; Parmar, VK; Sardana, S, 2010)	0.36
"Our studies propose for the first time a stable NOS-beta-CD inclusion complex as an effective approach to enhance the solubility and bioavailability of NOS for anticancer therapy."	( Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics. Aneja, R; Bharatam, PV; Chandra, R; Dhiman, N; Katyal, A; Madan, J; Parmar, VK; Sardana, S, 2010)	0.36
"Inclusion complexes of cyclodextrins with nonpolar drugs are a topic of current interest in pharmaceutical science, because they increase the aqueous solubility, chemical stability and bioavailability of poorly water-soluble drugs."	( Influence of the "host-guest" interactions on the mobility of genistein/beta-cyclodextrin inclusion complex. Crupi, V; Majolino, D; Paciaroni, A; Stancanelli, R; Venuti, V, 2009)	0.35
"81-fold enhancement in apparent bioavailability compared to artemether."	( Artemether/hydroxypropyl-beta-cyclodextrin host-guest system: characterization, phase-solubility and inclusion mode. Chen, Y; Lin, J; Liu, Y; Yang, B, 2009)	0.35
" High PCBs removal percentage was due to the increased PCBs bioavailability as well as biostimulation of microbial communities after plantation and RAMEB addition."	( Enhanced phytoremediation potential of polychlorinated biphenyl contaminated soil from e-waste recycling area in the presence of randomly methylated-beta-cyclodextrins. Cheema, SA; Chen, X; Chen, Y; Khan, MI; Liang, F; Lin, Q; Shen, C; Tang, X; Zhang, C; Zhu, Y, 2009)	0.35
"The effect of two water-soluble polymers: pectin and polyvinylpyrrolidone in combination with beta-cyclodextrin, on the dissolution, bioavailability and cysticidal efficacy of albendazole was evaluated using a commercial suspension as reference product."	( Two novel ternary albendazole-cyclodextrin-polymer systems: dissolution, bioavailability and efficacy against Taenia crassiceps cysts. Bernad-Bernad, MJ; Castro-Torres, N; Estrada, EP; González, CR; González-Hernández, I; Hernández, GP; Jung-Cook, H; Montiel, MD; Palomares-Alonso, F, 2010)	0.36
"The aim of this study was to prepare the inclusion complex of genipin (GP) and beta-cyclodextrin (beta-CD) with improved stability, solubility, and bioavailability and to study the pharmacokinetics of beta-CD inclusion complex in mice."	( Preparation, characterization, and pharmacokinetics of the inclusion complex of genipin-beta-cyclodextrin. Ji, G; Lu, Y; Tao, J; Wang, S; Zhang, T, 2009)	0.35
"The relative bioavailability of the inclusion complex of GP-beta-CD to free GP was 305."	( Preparation, characterization, and pharmacokinetics of the inclusion complex of genipin-beta-cyclodextrin. Ji, G; Lu, Y; Tao, J; Wang, S; Zhang, T, 2009)	0.35
"Carvedilol a poorly water soluble drug undergoes extensive first pass metabolism, which reduces its bioavailability to 25-30%."	( Studies on formulation development of mouth dissolving tablets of Carvedilol. Dhar, S; Mandpe, L; Pokharkar, V, )	0.13
" The oral bioavailability of the BS/beta-CD complex (approximately 37%) was approximately 2-fold of the free BS ( approximately 20%)."	( Pre-clinical pharmacokinetics evaluation of an anticonvulsant candidate benzaldehyde semicarbazone free and included in beta-cyclodextrin. Azeredo, FJ; Beraldo, Hde O; Dalla Costa, T; Kaiser, M; Uchôa, Fde T, 2010)	0.36
" On the other hand, bioavailability of oral mucosal, rectal and oral administration was about 100, 63."	( A novel administration route of edaravone--II: mucosal absorption of edaravone from edaravone/hydroxypropyl-beta-cyclodextrin complex solution including L-cysteine and sodium hydrogen sulfite. Ishii, F; Mizuno, K; Sato, T, 2010)	0.36
"The objective of this study was to enhance the solubility, dissolution rate, and oral bioavailability of a very poorly water-soluble anti-fungal agent, ketoconazole (KET), by inclusion complexation with a highly-soluble cyclodextrin derivative, hydroxypropyl-beta cyclodextrin (HP-beta-CD)."	( In vitro and in vivo evaluation of oral tablet formulations prepared with ketoconazole and hydroxypropyl-beta-cyclodextrin. Guneri, T; Ozcan, I; Taneri, F, 2010)	0.36
" In the range 2-4mM of host, solubility of DHK was increased only two-fold, but being beta-CyD also a penetration enhancer, in vivo studies will be performed to clarify a possible role of the complex on the bioavailability of DHK."	( Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex. Bergonzi, MC; Bilia, AR; Di Bari, L; Pescitelli, G; Vincieri, FF, 2010)	0.36
"The main purpose of this study was to evaluate the effect of a mixed drug solution containing a surfactant and beta-cyclodextrin (beta-CD) on the solubility and bioavailability of a poorly water soluble drug, flurbiprofen."	( Enhanced oral bioavailability of flurbiprofen by combined use of micelle solution and inclusion compound. Balakrishnan, P; Choi, HG; Han, MJ; Joe, JH; Kim, JO; Li, DX; Oh, DH; Park, SM; Seo, Y; Yan, YD; Yong, CS, 2010)	0.36
" Thus, dissolution profiles suggested that combination of kappa-carrageenan and sodium starch glycolate resulted into fast-disintegrating, immediate-release pellets, overcoming the bioavailability problem of the poorly soluble drug, aceclofenac, and enteric coating of these pellets avoids the exposure of aceclofenac to ulcer-prone areas of the gastrointestinal tract."	( Development and characterization of enteric-coated immediate-release pellets of aceclofenac by extrusion/spheronization technique using kappa-carrageenan as a pelletizing agent. Awari, JG; Kilor, VA; Sapkal, NP; Shewale, BD, 2010)	0.36
" In this study, a novel paclitaxel (Pac) formulation was investigated for its toxicity and bioavailability during HIPEC compared with Taxol."	( In vivo toxicity and bioavailability of Taxol and a paclitaxel/beta-cyclodextrin formulation in a rat model during HIPEC. Adriaens, E; Almeida, A; Bouquet, W; Ceelen, W; De Vos, F; Pattyn, P; Peeters, M; Quinten, T; Remon, JP; Vervaet, C, 2010)	0.36
" Bioavailability of both Pac formulations after HIPEC was determined under normothermic (37 degrees C) and hyperthermic (41 degrees C) conditions for 90 min."	( In vivo toxicity and bioavailability of Taxol and a paclitaxel/beta-cyclodextrin formulation in a rat model during HIPEC. Adriaens, E; Almeida, A; Bouquet, W; Ceelen, W; De Vos, F; Pattyn, P; Peeters, M; Quinten, T; Remon, JP; Vervaet, C, 2010)	0.36
" Bioavailability data of Pac/RAME-beta-CD showed a 40-fold increase of the area under the curve (AUC) of plasma concentrations compared with Taxol."	( In vivo toxicity and bioavailability of Taxol and a paclitaxel/beta-cyclodextrin formulation in a rat model during HIPEC. Adriaens, E; Almeida, A; Bouquet, W; Ceelen, W; De Vos, F; Pattyn, P; Peeters, M; Quinten, T; Remon, JP; Vervaet, C, 2010)	0.36
" The relative oral bioavailability of paclitaxel-loaded nanosponges was 256."	( Enhanced oral paclitaxel bioavailability after administration of paclitaxel-loaded nanosponges. Ansari, KA; Cavalli, R; Torne, SJ; Trotta, F; Vavia, PR, 2010)	0.36
"985) and extraction results for pyrene suggested that mild HPCD extraction was a better method to predict bioavailability of pyrene in soil compared with organic solvent extraction."	( Assessment of pyrene bioavailability in soil by mild hydroxypropyl-β-cyclodextrin extraction. Cheema, SA; Chen, X; Chen, Y; Khan, MI; Malik, Z; Shen, C; Tang, X; Zhang, C, 2011)	0.37
" However, its prominent application in cancer treatment is limited due to sub-optimal pharmacokinetics and poor bioavailability at the tumor site."	( beta-Cyclodextrin-curcumin self-assembly enhances curcumin delivery in prostate cancer cells. Chauhan, SC; Jaggi, M; Yallapu, MM, 2010)	0.36
" It was concluded that high PCB degradation was due to the increased PCB bioavailability as well as biostimulation of microbial communities after plantation and beta-cyclodextrin addition."	( Beta-cyclodextrin enhanced phytoremediation of aged PCBs-contaminated soil from e-waste recycling area. Cheema, SA; Chen, Y; Liu, W; Shen, C; Tang, X, 2010)	0.36
"The ACZ:HP-beta-CD:TEA complex is an important new approach to improve the ocular bioavailability of this drug."	( Promising complexes of acetazolamide for topical ocular administration. Granero, GE; Longhi, MR, 2010)	0.36
"The objective of the present study was to evaluate the potential influence of carboxymethyl-beta-cyclodextrin (CM-beta-CyD) on the aqueous solubility, chemical stability and oral bioavailability of famotidine (FMT) as well as on its bitter taste."	( Evaluation of carboxymethyl-beta-cyclodextrin with acid function: improvement of chemical stability, oral bioavailability and bitter taste of famotidine. Abou-Taleb, AE; Anraku, M; Hirayama, F; Iohara, D; Khaled, KA; Mady, FM; Otagiri, M; Taguchi, K; Uekama, K; Yamasaki, K, 2010)	0.36
"The aim of the study was to investigate the tissue tolerance and bioavailability of four formulations containing 5% ricobendazole solubilised at low pH, following subcutaneous injection in sheep."	( Tissue compatibility and pharmacokinetics of three potential subcutaneous injectables for low-pH drug solutions. McSporran, K; Medlicott, NJ; Razzak, M; Tucker, IG; Wu, Z, 2010)	0.36
" This may be due to an icreased systemic bioavailability of meloxicam after oral administration of its complex with beta-cyclodextrin."	( Influence on analgesic activity and serum levels after meloxicam complexation with beta-cyclodextrin in mice and rats. Dolezal, T; Janovský, M; Krsiak, M; Procháizková, M; Slíva, J, 2010)	0.36
" When biopharmaceutics of the optimized cyclodextrin-based formulation of SQV was studied in Wistar rats after intravenous and oral administrations, we found that inclusion of SQV into M-β-CyD could dramatically improve its oral bioavailability and decrease the variation of its oral pharmacokinetics."	( Enhanced oral absorption of saquinavir with Methyl-Beta-Cyclodextrin-Preparation and in vitro and in vivo evaluation. Bhat, K; Dengle, S; Karthik, A; Musmade, P; Pathak, SM; Udupa, N, 2010)	0.36
"To increase the aqueous solubility and poor bioavailability of capsaicin (CAS 404-86-4), in this paper, the effects of hydroxypropyl-beta-cyclodextrin (HP-beta-CD) on the aqueous solubility and the pharmacokinetic characteristics of capsaicin were investigated."	( Enhanced aqueous solubility and bioavailability of capsaicin by the preparation of an inclusion complex. Chen, X; Gong, T; Ren, K; Sun, X; Zhang, X; Zhang, Z, 2010)	0.36
" One technique for increasing the solubility and bioavailability of a cytotoxic agent is the formation of inclusion complexes with cyclodextrins."	( Molecular recognition and enhancement of aqueous solubility and bioactivity of CD437 by β-cyclodextrin. Battle, CH; Griffin, ME; Jayawickramarajah, J; Mishur, RJ; Shan, B, 2011)	0.37
" It is an ionizable drug, whose solubility depends on the gastrointestinal pH, and the bioavailability is therefore very variable."	( Physico-chemical characterization and in vitro/in vivo evaluation of loratadine:dimethyl-β-cyclodextrin inclusion complexes. Aigner, Z; Balogh, Á; Blazsó, G; Mándity, I; Martinek, T; Sipos, P; Szabados-Nacsa, A; Szabó-Révész, P, 2011)	0.37
" Tablets of the resulting complex were prepared using direct compression method and the bioavailability was evaluated in beagle dogs using a UPLC/MS/MS method."	( In vitro and in vivo evaluation of novel immediate release carbamazepine tablets: complexation with hydroxypropyl-β-cyclodextrin in the presence of HPMC. Cai, C; Kou, W; Liu, J; Wang, H; Xu, S; Yang, D; Zhang, T, 2011)	0.37
" The oral bioavailability of ML-βCD-PEG was investigated by administration to rat and compared with ML and ML-βCD."	( Preparation of meloxicam-β-cyclodextrin-polyethylene glycol 6000 ternary system: characterization, in vitro and in vivo bioavailability. Moulay-Hassane, G; Radia, O; Rogalska, E, )	0.13
" These nano-assemblies can function as gastro-OFF/intestinal-ON delivery systems to selectively transport payload to enteric sites, thereby dramatically increasing the oral bioavailability of the loaded therapeutic, which can also serve as multifunctional nano-platforms for multiple delivery of various therapeutics."	( Highly efficient nanomedicines assembled via polymer-drug multiple interactions: Tissue-selective delivery carriers. Che, L; He, H; Jia, Y; Li, X; Zhang, J; Zhu, Y, 2011)	0.37
"The purpose of this study was to evaluate the potential of a newly modified cyclodextrin derivative, water-soluble β-cyclodextrin-epichlorohydrin polymer (β-CDP), as an effective drug carrier to enhance the dissolution rate and oral bioavailability of glipizide as a poorly water-soluble model drug."	( In vitro and in vivo studies on the complexes of glipizide with water-soluble β-cyclodextrin-epichlorohydrin polymers. Liu, Y; Nie, S; Pan, W; Zhang, S, 2011)	0.37
" The above results indicated that C(max), T(max), AUC(0-t), AUC(0-∞), and MRT in RCO-βCD group were significantly different from RCO-PD group, and the relative bioavailability of RCO-βCD group is significantly higher while compared to RCO-PD group (F=156%, with its 90% confidence interval of 145-169%)."	( Pharmacokinetic study of rhizoma Curcumae oil and rhizoma Curcumae oil-β-cyclodextrin inclusion complex in pigs after oral administration. Dongping, Z; Gang, W; Haiyan, Z; Yong-Xue, S; Yongjin, L; Zhichang, L, 2012)	0.38
"Etoricoxib is an anti-inflammatory drug largely used in a variety of acute and chronic inflammatory diseases, but is associated with low aqueous solubility and poor dissolution leading to a delayed rate of absorption and onset of action."	( Development and pharmacological evaluation of cyclodextrin complexes of etoricoxib. Arora, S; Kumar, P; Pahuja, S; Singh, I; Tung, V, )	0.13
" However, naringenin suffers from low oral bioavailability critically limiting its clinical potential."	( Enhancement of naringenin bioavailability by complexation with hydroxypropyl-β-cyclodextrin. [corrected]. Benny-Ratsaby, O; Cohen, M; Goldwasser, J; Lee-Parsons, CW; Nahmias, Y; Shulman, M; Soto-Gutierrez, A; Wang, H; Yagi, H; Yarmush, ML, 2011)	0.37
"The practical applicability of solid dispersions (SD) for improvement of oral bioavailability of poorly water-soluble drugs has still remained limited because of lack of feasibility for scale-up of manufacturing processes."	( An optimized commercially feasible milling technique for molecular encapsulation of meloxicam in β-cyclodextrin. Bandarkar, FS; Vavia, PR, 2011)	0.37
"Cyclodextrins (CDs) are able to enhance the solubility, stability and bioavailability of several bioactive hydrophobic compounds by complex formation."	( Phase solubility studies and stability of cholesterol/β-cyclodextrin inclusion complexes. Buera, MP; dos Santos, C; Mazzobre, MF, 2011)	0.37
"Effervescent tablets produced using an inclusion complex of BNZ with CD suggest a possible improvement in the bioavailability of BNZ, and this could represent a relevant advance in Chagas therapy."	( Development of effervescent tablets containing benzonidazole complexed with cyclodextrin. Bahia, MT; Costa, GH; Cunha-Filho, MS; de Sá Barreto, LC; Maximiano, FP, 2011)	0.37
" Its poor aqueous solubility is one of the reasons for its limited bioavailability after oral administration."	( Pharmaceutical composition of hydrochlorothiazide:β-cyclo-dextrin: preparation by three different methods, physico-chemical characterization and in vivo diuretic activity evaluation. Pires, MA; Sinisterra, RD; Souza Dos Santos, RA, 2011)	0.37
"Dihydroartemisinin (DHA) is a poorly water-soluble drug that displays low bioavailability after oral administration."	( Improving the solubility and bioavailability of dihydroartemisinin by solid dispersions and inclusion complexes. Ansari, MT; Batty, KT; Iqbal, I; Sunderland, VB, 2011)	0.37
"Intestinal absorption and bioavailability of taxol are limited by its low solubility and P-glycoprotein (Pgp) activity."	( Randomly methylated β-cyclodextrin derivatives enhance taxol permeability through human intestinal epithelial Caco-2 cell monolayer. Bácskay, I; Deli, MA; Fehér, P; Fenyvesi, E; Fenyvesi, F; Kiss, T; Szente, L; Tósaki, A; Ujhelyi, Z; Váradi, J; Vecsernyés, M; Veszelka, S, 2011)	0.37
" However, it ionizes at physiological pH resultant low bioavailability and therapeutic efficacy."	( Inclusion complex of colchicine in hydroxypropyl-β-cyclodextrin tenders better solubility and improved pharmacokinetics. Chauhan, R; Kaushik, D; Madan, J; Pandey, RS; Sardana, S; Sharma, R, )	0.13
"We have attempted to augment the bioavailability of CLC by fabricating the inclusion complex with hydroxypropyl-β-cyclodextrin (HP-β-CD)."	( Inclusion complex of colchicine in hydroxypropyl-β-cyclodextrin tenders better solubility and improved pharmacokinetics. Chauhan, R; Kaushik, D; Madan, J; Pandey, RS; Sardana, S; Sharma, R, )	0.13
" Oral bioavailability of CLC-HP-β-CD inclusion complex was analyzed using high performance liquid chromatography method."	( Inclusion complex of colchicine in hydroxypropyl-β-cyclodextrin tenders better solubility and improved pharmacokinetics. Chauhan, R; Kaushik, D; Madan, J; Pandey, RS; Sardana, S; Sharma, R, )	0.13
"82-fold increase in absolute bioavailability of CLC upon complexation."	( Inclusion complex of colchicine in hydroxypropyl-β-cyclodextrin tenders better solubility and improved pharmacokinetics. Chauhan, R; Kaushik, D; Madan, J; Pandey, RS; Sardana, S; Sharma, R, )	0.13
" Relative bioavailability of ATO when loaded in nanoparticles ranged from 52% (for ATO-HPCD NP) to 71% (for ATO-DMCD NP), whereas for the suspension control formulation the bioavailability was only about 30%."	( Cyclodextrin/poly(anhydride) nanoparticles as drug carriers for the oral delivery of atovaquone. Agüeros, M; Calvo, J; Irache, JM; Lavandera, JL, 2011)	0.37
" Correlation results for phenanthrene suggested that mild HPCD extraction was a better method to predict bioavailability of phenanthrene in soil compared with organic solvents extraction."	( Assessment of phenanthrene bioavailability in aged and unaged soils by mild extraction. Cheema, SA; Chen, X; Chen, Y; Khan, MI; Park, J; Shen, C; Shi, J; Tang, X; Zhang, C, 2012)	0.38
" To achieve optimal bioavailability and control their fast rate of absorption, peptides can be protected by coprocessing with polymers such as polyethylene glycol (PEG)."	( Evaluation of HPβCD-PEG microparticles for salmon calcitonin administration via pulmonary delivery. Amaro, MI; Corrigan, OI; Ehrhardt, C; Gobbo, OL; Healy, AM; Tajber, L; Tewes, F, 2011)	0.37
" However, suboptimal pharmacokinetics and poor bioavailability limit its effective use in cancer therapeutics."	( Design of curcumin loaded cellulose nanoparticles for prostate cancer. Chauhan, SC; Dobberpuhl, MR; Jaggi, M; Maher, DM; Yallapu, MM, 2012)	0.38
"Fosinopril is one of the most hydrophobic substances among the angiotensin-converting enzyme inhibitors, exhibiting low water solubility and poor bioavailability following oral administration."	( Fosinopril-cyclodextrin inclusion complexes: phase solubility and physicochemical analysis. Bojiţă, M; Drăgan, L; Sbârcea, L; Szabadai, Z; Trandafirescu, C; Udrescu, L, 2011)	0.37
" The absorption rate and permeability value of the inclusion complex were significantly higher than the free drug, suggesting that its enhancing effect was involved in its solubilizing effect and Pgp inhibitory effect."	( Enhancing effect of hydroxypropyl-β-cyclodextrin on the intestinal absorption process of genipin. Cui, YL; Meng, FC; Song, YF; Zhang, Y, 2011)	0.37
"The developed HP-β-CD-based mucoadhesive system is a viable alternative to conventional eye drops of DXN due to its ability to enhance bioavailability through its longer precorneal residence time and ability to sustain the release of the drug."	( Effect of hydroxypropyl-β-cyclodextrin on the ocular bioavailability of dexamethasone from a pH-induced mucoadhesive hydrogel. Kant, S; Kesavan, K; Pandit, JK; Singh, PN, 2011)	0.37
" Meloxicam is practically insoluble in water (8µg/ml), which directly influences the C(max), T(max), as well as the bioavailability of the drug."	( Development of meloxicam formulations utilizing ternary complexation for solubility enhancement. Awasthi, SS; Kumar, SS; Kumar, TG; Manisha, P; Preeti, Y, 2011)	0.37
" The relative bioavailability of the selected gum tablet was found to be 166."	( Immediate release three-layered chewing gum tablets of fenoprofen calcium: preparation, optimization and bioavailability studies in healthy human volunteers. Abdelbary, AA; Amin, MM; El Assassy, AE, 2012)	0.38
" The formulation, that provided delivery of active material near to the target value in six healthy volunteers and in vivo tests, clearly revealed that the bioavailability of active material was found to be enhanced by preparing ternary mixtures."	( Enhancement of dissolution rate and bioavailability of sulfamethoxazole by complexation with β-cyclodextrin. Erkin, J; Ozdemir, N, 2012)	0.38
" In an attempt to improve the bioavailability and the stability of four of these derivatives, we propose here two different approaches: complexation with β-cyclodextrin derivatives and incorporation of these substances inside antioxidant micelles."	( Overcoming instability and low solubility of new cytostatic compounds: a comparison of two approaches. Bauer-Brandl, A; di Cagno, M; Hlaváč, J; Skalko-Basnet, N; Stein, PC; Styskala, J, 2012)	0.38
"The aim of this work was to investigate the inclusion complexes between mosapride citrate and SBE7β-CD in comparison with the natural β-CD to enhance its bioavailability by improving the solubility and dissolution rate."	( Preparation and characterization of mosapride citrate inclusion complexes with natural and synthetic cyclodextrins. Ali, AA; Sayed, OM, )	0.13
" Midazolam displayed rapid sublingual absorption (mean t(max) ≤30min from the liquid formulations and 60 min from the solid formulation) with high absolute bioavailability (>68%) from all evaluated formulations."	( The effect of hydroxypropyl-beta-cyclodextrin and sucrose on the sublingual absorption of midazolam in rabbits. Jarho, P; Järvinen, K; Kaartama, R; Kokki, H; Lehtonen, M; Ranta, VP; Savolainen, J; Toljamo, K; Turunen, E, 2012)	0.38
" Its activity was tested against multiple cancer cell lines, and in vivo bioavailability was checked."	( Inclusion complex of novel curcumin analogue CDF and β-cyclodextrin (1:2) and its enhanced in vivo anticancer activity against pancreatic cancer. Ahmad, A; Banerjee, S; Dandawate, PR; Deshpande, J; Dumhe-Klaire, AC; Jamadar, A; Padhye, S; Sarkar, FH; Swamy, KV; Vyas, A, 2012)	0.38
" Synthesis of such CDF-β-cyclodextrin self-assembly is an effective strategy to enhance its bioavailability and tissue distribution, warranting further evaluation for CDF delivery in clinical settings for treatment of human malignancies."	( Inclusion complex of novel curcumin analogue CDF and β-cyclodextrin (1:2) and its enhanced in vivo anticancer activity against pancreatic cancer. Ahmad, A; Banerjee, S; Dandawate, PR; Deshpande, J; Dumhe-Klaire, AC; Jamadar, A; Padhye, S; Sarkar, FH; Swamy, KV; Vyas, A, 2012)	0.38
"Artesunate (AST), the most widely used artemisnin derivative, has poor aqueous solubility and suffers from low oral bioavailability (~40%)."	( Artesunate-loaded chitosan/lecithin nanoparticles: preparation, characterization, and in vivo studies. Chadha, R; Gupta, S; Pathak, N, 2012)	0.38
"The aim of this study was to improve the solubility, stability and bioavailability of amorphous atorvastatin calcium (AT) by complexing it with hydroxypropyl-beta-cyclodextrin."	( Preparation, physicochemical characteristics and bioavailability studies of an atorvastatin hydroxypropyl-beta-cyclodextrin complex. Lv, HX; Waddad, AY; Zhang, ZH; Zhou, JP, 2012)	0.38
"The present study aimed to improve solubility, dissolution and ultimate bioavailability of poorly soluble artemether, an antimalarial drug, by encapsulating it in β-cyclodextrin (β-CD) and its methyl and hydroxylpropyl derivatives."	( Characterization, thermodynamic parameters and in vivo antimalarial activity of inclusion complexes of artemether. Chadha, R; Gupta, S; Jain, DS; Shukla, G; Singh, S, 2010)	0.36
" The results confirmed the benefit of using CDs as a useful tool to enhance the dissolution and hence bioavailability of poorly water-soluble drugs by forming solubilizing systems when exposed to gastrointestinal fluid."	( Comparative evaluation of ketoconazole-β-cyclodextrin systems prepared by coprecipitation and kneading. Amer, RI; Kassem, AA; Marzouk, MA; Samy, AM, 2010)	0.36
"Cyclodextrins (CDs) are widely used both in pharmaceutical applications to improve drug bioavailability and in cell biology as cholesterol-depleting and -delivering agents."	( Uptake of a fluorescent methyl-β-cyclodextrin via clathrin-dependent endocytosis. Fenyvesi, É; Herrmann, A; Höfer, CT; Jicsinszky, L; Müller, P; Plazzo, AP; Schiller, J; Szente, L, 2012)	0.38
"Considering the poor water solubility and the low oral bioavailability in humans, the complex formation of fenofibrate (FNB) with hydroxypropyl-beta-cyclodextrin (HP-beta-CD) in aqueous solution was studied."	( Investigation of a fenofibrate-hydroxypropyl-beta-cyclodextrin system prepared by a co-grinding method. Gu, FG; Han, HB; Meng, GD; Wang, Y; Wu, CZ, 2012)	0.38
"Over the last decades the poor solubility of new drugs has become an important issue, with one of the main challenges being to develop oral dosage forms with acceptable bioavailability for such compounds."	( Application of a ternary HP-β-CD-complex approach to improve the dissolution performance of a poorly soluble weak acid under biorelevant conditions. Dressman, JB; Klein, S; Zoeller, T, 2012)	0.38
"n-butanol and hydroxypropyl-beta-cyclodextrin (HPCD) were used to extract polyclic aromatic hydrocarbons from 9 aged agricultural fields and to assess the PAHs bioavailability to earthworm (Eisenia fetida)."	( [Mild solvent extraction technique for the evaluation of PAHs bioavailability]. Jiang, X; Lü, ZY; Wang, F; Yang, XL; Zhang, YP, 2011)	0.37
"To assess the relative bioavailability of diclofenac sodium hydroxypropyl β-cyclodextrin (HPβCD) administered via the subcutaneous (s."	( Pharmacokinetics of a new diclofenac sodium formulation developed for subcutaneous and intramuscular administration. Ducharme, MP; Gugliotta, B; Müller, M; Oraha, AZ; Rusca, A; Zeitlinger, M, 2012)	0.38
"One single-dose, randomized, three-way, crossover relative bioavailability study and one linearity single escalating dose, randomized, three-way cross-over pharmacokinetic study were conducted at two different clinical sites."	( Pharmacokinetics of a new diclofenac sodium formulation developed for subcutaneous and intramuscular administration. Ducharme, MP; Gugliotta, B; Müller, M; Oraha, AZ; Rusca, A; Zeitlinger, M, 2012)	0.38
"The aim of this research is to develop novel chitosan nanoparticles including cyclodextrins complexes for docetaxel (DTX), evaluate the performance of nanoparticles which could enhance the oral permeability and bioavailability of DTX in vitro and in vivo."	( Sulfobutylether-β-cyclodextrin/chitosan nanoparticles enhance the oral permeability and bioavailability of docetaxel. Fang, L; Shen, Q; Wu, J, 2013)	0.39
"The 2:1 (molar ratio) complexes between beta-CD and coptisine hydrochloride is formed, which improves the bioavailability of coptisine hydrochloride."	( [Preparation and stuctural behavior of the inclusion complex of beta-cyclodextrin and coptisine hydrochloride]. Chen, HY; Chen, SQ; Jin, Z, 2012)	0.38
" The developed tablet formulation could be a promising drug delivery system with improvements in PPZ bioavailability and patient compliance."	( Development of orally disintegrating tablets of Perphenazine/hydroxypropyl-β-cyclodextrin inclusion complex. Wang, L; Zeng, F; Zong, L, )	0.13
"To study the effect of β-cyclodextrin (βCD) inclusion complex on the bioavailability of clotrimazole from poloxamer-based suppository, formulations composed of P 188, propylene glycol and different molar ratio of clotrimazole-βCD inclusion complex were prepared."	( Inclusion complex effect on the bioavailability of clotrimazole from poloxamer-based solid suppository. Balakrishnan, P; Cho, HJ; Choi, HG; Kim, DD; Song, CK; Yang, SG; Yong, CS, 2012)	0.38
" In ophthalmic formulations, cyclodextrins (CDs) are frequently used in recent years in order to increase water solubility, stability and bioavailability of an active substance and decrease an irritation to the eye."	( Effect of hydroxypropyl-beta-cyclodextrin on the solubility, stability and in-vitro release of ciprofloxacin for ocular drug delivery. Basaran, B; Bozkir, A; Denli, ZF, )	0.13
" The effectiveness of many in situ bioremediation systems may be constrained by low contaminant bioavailability due to limited aqueous solubility or a large magnitude of sorption."	( Methyl-beta-cyclodextrin enhanced biodegradation of polycyclic aromatic hydrocarbons and associated microbial activity in contaminated soil. Christie, P; Jia, Z; Li, Z; Luo, Y; Sun, M; Teng, Y, 2012)	0.38
" Results of in vivo pharmacokinetic studies revealed that, nanocomposites effectively bypass variation in pharmacokinetic parameters at fed and fasted states with 346%, 315%, 301% and 321% increase in relative bioavailability compared to marketed formulation and pure TEL in fed and fasted conditions respectively."	( Amorphous ternary cyclodextrin nanocomposites of telmisartan for oral drug delivery: improved solubility and reduced pharmacokinetic variability. Sangwai, M; Vavia, P, 2013)	0.39
" In the present study, we focused on maltosyl-β-cyclodextrin (malt-β-CD) as a new water-soluble carrier and it was investigated whether drug/malt-β-CD microspheres could improve the bioavailability compared with our previously reported drug/mannitol (MAN) microspheres."	( Improved bioavailability of a water-insoluble drug by inhalation of drug-containing maltosyl-β-cyclodextrin microspheres using a four-fluid nozzle spray drier. Kano, Y; Okada, H; Ozeki, T; Tagami, T; Takahashi, N, 2012)	0.38
" Research was conducted to find procedures that might result in an increase in the bioavailability of diuron in contaminated soils, through solubility enhancement."	( Enhanced mineralization of diuron using a cyclodextrin-based bioremediation technology. Laiz, L; Morillo, E; Posada-Baquero, R; Rubio-Bellido, M; Saiz-Jimenez, C; Sanchez-Trujillo, MA; Villaverde, J, 2012)	0.38
" Compared with the commercial tablet, the relative oral bioavailability of IND-nanomedicines was significantly enhanced."	( Assembled nanomedicines as efficient and safe therapeutics for articular inflammation. Che, L; He, H; Jia, Y; Li, S; Li, X; Liu, Y; Zhang, J; Zhou, J; Zhou, X; Zhu, Y, 2012)	0.38
"Bioremediation of surface waters contaminated with polycyclic aromatic hydrocarbons (PAHs) is a serious problem, often limited by the low bioavailability of contaminants as a result of their low aqueous solubility."	( Investigation into the causes for the changed biodegradation process of dissolved pyrene after addition of hydroxypropyl-β-cyclodextrin (HPCD). Li, CM; Zhang, Y; Zhang, ZX; Zhu, YX, 2012)	0.38
"In this study, amorphous solid dispersions containing dutasteride and various excipients, manufactured by spray-drying processes, were characterized to determine the effects on their ability to form supersaturated solutions and to identify the effects of supersaturation on increasing the bioavailability of dutasteride."	( Improved supersaturation and oral absorption of dutasteride by amorphous solid dispersions. Beak, IH; Kim, MS, 2012)	0.38
" When DFS was given as a suspension (6 mg/kg), the absolute oral bioavailability (F) was almost negligible."	( Quantification of trans-2,6-difluoro-4'-N,N-dimethylaminostilbene in rat plasma: application to a pharmacokinetic study. Anderson, BD; Ho, PC; Lin, HS; Liu, C; Ong, PS; Sviripa, VM; Watt, DS; Xiang, TX, 2013)	0.39
" The latest nanoparticle technology can help to improve the bioavailability of curcumin, which is affected by the final particle size and stability."	( Highly stabilized curcumin nanoparticles tested in an in vitro blood-brain barrier model and in Alzheimer's disease Tg2576 mice. Baum, L; Cheng, KK; Chow, AH; Chow, SF; Ho, SW; Yeung, CF, 2013)	0.39
" The purpose of the present study was to develop ophthalmic in situ gelling systems of ciprofloxacin hydrochloride with reduced pre-corneal elimination in order to improve the bioavailability and therapeutic response."	( Thermosensitive and pH induced in situ ophthalmic gelling system for ciprofloxacin hydrochloride: hydroxypropyl-beta-cyclodextrin complex. Başaran, B; Bozkir, A, )	0.13
" Bioavailability in vivo was determined by administering the compression-coated tablets to rabbits in contrast with Glucotrol XL(®)."	( Compression-coated tablets of glipizide using hydroxypropylcellulose for zero-order release: in vitro and in vivo evaluation. Chen, H; Chen, Q; Huang, H; Qi, X; Rui, Y; Wu, Z; Xing, J; Zhang, H, 2013)	0.39
" Given its poor water solubility and low oral bioavailability (1-4%), there are limitations to the utilization of KP."	( Novel formulation strategies for enhancing oral delivery of methoxyflavones in Kaempferia parviflora by SMEDDS or complexation with 2-hydroxypropyl-β-cyclodextrin. Jay, M; Leed, MG; Mekjaruskul, C; Sadgrove, MP; Sripanidkulchai, B; Yang, YT, 2013)	0.39
" This study aimed to investigate the impacts of aqueous solubility, fasting, dose escalation, and dosing route on its bioavailability in Sprague-Dawley rats."	( Pharmacokinetics of pterostilbene in Sprague-Dawley rats: the impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability. Ho, PC; Lin, HS; Yeo, SC, 2013)	0.39
" When given in oral suspension (15 mg/kg), PTS had relatively low bioavailability (F = 15."	( Pharmacokinetics of pterostilbene in Sprague-Dawley rats: the impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability. Ho, PC; Lin, HS; Yeo, SC, 2013)	0.39
"Aqueous solubility was identified as a barrier to its oral bioavailability while solubilizing PTS with HP-β-CD substantially increased its bioavailability; dose manipulation was a practical strategy to enhance its bioavailability and systemic exposure; and its delivery through oral mucosa was feasible."	( Pharmacokinetics of pterostilbene in Sprague-Dawley rats: the impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability. Ho, PC; Lin, HS; Yeo, SC, 2013)	0.39
"Upregulation of caveolin-1 protein expression and reduced NO bioavailability contributes to aortic endothelial dysfunction in AngII-infused ApoE(-/-) mice."	( Impaired acetylcholine-induced endothelium-dependent aortic relaxation by caveolin-1 in angiotensin II-infused apolipoprotein-E (ApoE-/-) knockout mice. Golledge, J; Khosla, S; Krishna, SM; Liu, D; Seto, SW; Yu, H, 2013)	0.39
" However, its low water-solubility and bioavailability could limit its use in both food and pharmaceutical fields."	( Reversed phase High Performance Liquid Chromatography used for the physicochemical and thermodynamic characterization of piceatannol/β-cyclodextrin complex. Amira-Guebailia, H; Houache, O; Messiad, H, 2013)	0.39
" It was concluded that the inclusion complex could improve the aqueous solubility and bioavailability of ACADFE."	( Encapsulation of a flavonoid-rich Allium cepa L. var. agrogatum don extract in β-cyclodextrin for transdermal drug delivery. Ding, Z; Guo, Q; Wu, M; Yang, X; Zhang, B, 2013)	0.39
" The aim of this study is to investigate and compare the oral bioavailability and the pharmacokinetics of free BCP and BCP/β-CD inclusion complex after a single oral dose of 50mg/kg on rats."	( Physicochemical characterization and pharmacokinetics evaluation of β-caryophyllene/β-cyclodextrin inclusion complex. Cao, D; Fan, G; Liu, H; Qi, T; Qi, Y; Tang, Y; Yang, G, 2013)	0.39
"The aim of this study was to improve the solubility and oral bioavailability of clozapine (CLZ), a poorly water-soluble drug subjected to substantial first-pass metabolism, employing cyclodextrin complexation technique."	( Formulation and in vivo evaluation of orally disintegrating tablets of clozapine/hydroxypropyl-β-cyclodextrin inclusion complexes. Shi, K; Wang, L; Zeng, F; Zhang, W; Zong, L, 2013)	0.39
" The bioavailability of flurbiprofen from optimized nanoparticles was assessed in male Wistar rats at a dose of 15 mg/kg."	( Enhanced bioavailability of orally administered flurbiprofen by combined use of hydroxypropyl-cyclodextrin and poly(alkyl-cyanoacrylate) nanoparticles. Li, W; Luo, Q; Zhang, X; Zhao, X, 2014)	0.4
"Artemisinin, a poorly water-soluble antimalarial drug, presents a low and erratic bioavailability upon oral administration."	( Agglomerated oral dosage forms of artemisinin/β-cyclodextrin spray-dried primary microparticles showing increased dissolution rate and bioavailability. Balducci, AG; Bettini, R; Colombo, G; Colombo, P; Khan, NA; Magosso, E; Rossi, A; Sonvico, F; Yuen, KH, 2013)	0.39
" In rats, the oral bioavailability of dutasteride increased with the supersaturation induced by the HP-β-CD nanostructures."	( Influence of hydrophilic additives on the supersaturation and bioavailability of dutasteride-loaded hydroxypropyl-β-cyclodextrin nanostructures. Kim, MS, 2013)	0.39
"Study 1: Bioavailability in terms of AUC after IV administration was equivalent for HPβCD-diclofenac compared with Voltarol and after IM administration of HPβCD-diclofenac and Voltarol."	( Single-dose and multiple-dose pharmacokinetics and dose proportionality of intravenous and intramuscular HPβCD-diclofenac (Dyloject) compared with other diclofenac formulations. Carr, DB; Hamilton, DA; Lacouture, PG; Mermelstein, F; Ramaiya, A; Wright, C, 2013)	0.39
" The fisetin-Cys dimer complex showed also higher cytotoxicity to HeLa cells than free fisetin, indicating that the Cys dimer to improve bioavailability of fisetin."	( Complexation of fisetin with novel cyclosophoroase dimer to improve solubility and bioavailability. Cho, E; Choi, JM; Choi, Y; Jeong, D; Jeong, K; Jung, S, 2013)	0.39
" The use of β-CD allows an increase in the aqueous solubility of the drug, its bioavailability and then its bioactivity."	( β-Cyclodextrin inclusion complex to improve physicochemical properties of pipemidic acid: characterization and bioactivity evaluation. Caso, JV; Iacovino, R; Isernia, C; Isidori, M; Lavorgna, M; Malgieri, G; Rapuano, F; Russo, A; Russo, C; Russo, L, 2013)	0.39
" One of the most attractive strategies is the use of nanovehicles, because loading drugs into nanosized structures enhances their stability and solubility, thus improving their bioavailability and their antitumoral effectiveness."	( The inclusion complex of 4-hydroxynonenal with a polymeric derivative of β-cyclodextrin enhances the antitumoral efficacy of the aldehyde in several tumor cell lines and in a three-dimensional human melanoma model. Barrera, G; Biasi, F; Bisazza, A; Cavalli, R; Ciamporcero, E; Daga, M; Dianzani, C; Ferruti, P; Grazia Bernengo, M; Husse, M; Minelli, R; Novelli, M; Osella-Abate, S; Pettazzoni, P; Pizzimenti, S; Ranucci, E; Toaldo, C, 2013)	0.39
" Our results showed that complexation of rhubarb extract with HP-β-CD increased the aqueous solubility and bioavailability of rhubarb and thus enhanced its effect on hepatoma cells."	( Enhancement of rhubarb extract solubility and bioactivity by 2-hydroxypropyl-β-cyclodextrin. Hsu, CM; Tsai, FJ; Tsai, Y; Yu, SC, 2013)	0.39
" The coupling of ketoprofen with β-CD resulted in increased solubility (100% in 60 min) of the newly-formed product, which further resulted in a higher bioavailability compared with ketoprofen (<40% in 120 min)."	( Comparative assessment of effectiveness of ketoprofen and ketoprofen/beta-cyclodextrin complex in two experimental models of inflammation in rats. Grecu, M; Ilie, C; Mareş, M; Miron, L; Năstasă, V, 2014)	0.4
" The aim of this study is to improve the oral bioavailability of DX-9065 by cyclodextrins (CyDs) capable of interfering with such interaction."	( Cyclodextrins improve oral absorption of a novel factor Xa inhibitor by interfering with interaction between the drug and bile acids in rats. Fujii, Y; Irie, T; Ishiguro, T; Sakuma, S; Takahashi, M; Uekama, K, 2013)	0.39
" The bioavailability of the drug complex was comparable to that of Emend."	( Preparation and pharmacokinetic study of aprepitant-sulfobutyl ether-β-cyclodextrin complex. Chen, G; Li, M; Ren, L; Wei, P; Zhou, Y, 2014)	0.4
" β-Cyclodextrin-epichlorohydrin polymer is a high molecular weight compound, which acts as an effective drug carrier for enhancing the solubility and oral bioavailability of drugs along with the increase in therapeutic efficiency."	( Synthesis, characterization and application of epichlorohydrin-β-cyclodextrin polymer. Gidwani, B; Vyas, A, 2014)	0.4
" The aim of this study was to evaluate the solid-state stability of a fast-dissolving perphenazine/β-cyclodextrin (β-CD) complex, which has been found to be well absorbed after sublingual administration to rabbits."	( Effect of storage on the dissolution rate of a fast-dissolving perphenazine/β-cyclodextrin complex. Ahtiainen, H; Jarho, P; Järvinen, K; Kauppinen, A; Korhonen, O; Lehto, VP; Turunen, E, 2014)	0.4
"The therapeutic potential of acyclovir is limited by the low oral bioavailability owing to its limited aqueous solubility and low permeability."	( Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-β-cyclodextrin. Ahmed, M; Al-Dhubiab, BE; Attimarad, M; Harsha, S; Nair, AB; Wadhwa, J, 2014)	0.4
" The relative pharmacological availability and bioavailability of P-bis-CD nanocomplexes were 10."	( Penetratin derivative-based nanocomplexes for enhanced intestinal insulin delivery. Fan, T; Guan, S; Huang, Y; Jin, Y; Shan, W; Yang, Y; Zhang, P; Zhou, Z; Zhu, X, 2014)	0.4
"The aim of this study was to develop buspirone hydrochloride microemulsion formulations for intranasal administration to improve the drug bioavailability and provide high drug brain levels."	( Chitosan and cyclodextrin in intranasal microemulsion for improved brain buspirone hydrochloride pharmacokinetics in rats. Bshara, H; El-Shamy, Ael-H; Mansour, S; Osman, R, 2014)	0.4
"Telmisartan (TEL) requires superior bioavailability in cancer cell compartments."	( Telmisartan complex augments solubility, dissolution and drug delivery in prostate cancer cells. Bhatia, RK; Chandra, R; Coutinho, EC; Jain, UK; Katare, OP; Kaur, M; Madan, J; Pissurlenkar, RR, 2014)	0.4
"β-Cyclodextrin (β-CD), which is widely used to increase the stability, solubility, and bioavailability of guests, can form host-guest inclusion complexes with a wide variety of organic molecules."	( Preparation, characterization, and thermal stability of β-cyclodextrin/soybean lecithin inclusion complex. Luo, Z; Wang, X; Xiao, Z, 2014)	0.4
" Present work also suggests that properly optimized encapsulation in appropriate receptor pocket can enhance the bioavailability of drugs."	( Effect of encapsulation in the anion receptor pocket of sub-domain IIA of human serum albumin on the modulation of pKa of warfarin and structurally similar acidic guests: a possible implication on biological activity. Datta, S; Halder, M, 2014)	0.4
"The objective of the study was to evaluate the effect of hydroxypropyl-sulfobutyl-β-cyclodextrin (HP-SBE-βCD) on the bioavailability and intestinal absorption of edaravone, and identify its mechanism of action."	( Hydroxypropyl-sulfobutyl-β-cyclodextrin improves the oral bioavailability of edaravone by modulating drug efflux pump of enterocytes. Guo, M; Lu, Y; Lu, YP; Ren, Y; Rong, WT; Tao, Q; Yu, SQ, 2014)	0.4
"The potential bioavailability of phenanthrene aged in soil was determined by using a self-dying reporter bacterium, and the results were compared to two physicochemical measures, Tenax TA(®) bead-assisted desorption, and hydroxypropyl-β-cyclodextrin (HPCD) extraction."	( Potential use of a self-dying reporter bacterium to determine the bioavailability of aged phenanthrene in soil: comparison with physicochemical measures. Nam, K; Shin, D, 2014)	0.4
"To assess the relative bioavailability of a new subcutaneous (SC) diclofenac hydroxypropyl b-cyclodextrin (HPbCD) formulation administered to three body sites: quadriceps, gluteus, and abdomen."	( Pharmacokinetics of a new subcutaneous diclofenac formulation administered to three body sites: quadriceps, gluteus, and abdomen. Cardì, F; Drago, F; Gugliotta, B; Piazza, C; Salomone, S; Vitale, DC, 2014)	0.4
"This was a pilot, single-dose, randomized, three-way crossover relative bioavailability study."	( Pharmacokinetics of a new subcutaneous diclofenac formulation administered to three body sites: quadriceps, gluteus, and abdomen. Cardì, F; Drago, F; Gugliotta, B; Piazza, C; Salomone, S; Vitale, DC, 2014)	0.4
"The relative bioavailability of SC diclofenac HPbCD was comparable when administered to the quadriceps, gluteus, and abdomen."	( Pharmacokinetics of a new subcutaneous diclofenac formulation administered to three body sites: quadriceps, gluteus, and abdomen. Cardì, F; Drago, F; Gugliotta, B; Piazza, C; Salomone, S; Vitale, DC, 2014)	0.4
" Compared with the drug powder, the solubility, dissolution and bioavailability of tacrolimus with the fast-dissolving solid dispersion containing tacrolimus/HP-β-CD/DOSS in the weight ratio of 5:40:4 were boosted by approximately 700-, 30- and 2-fold, respectively."	( Development of novel fast-dissolving tacrolimus solid dispersion-loaded prolonged release tablet. Cho, JH; Choi, HG; Kim, DW; Kim, JO; Kim, YI; Woo, JS; Yong, CS; Yousaf, AM, 2014)	0.4
" We have already elucidated that the absolute oral bioavailability of diosgenin is very low; however, a high skin distribution of diosgenin was also observed."	( Effect of β-cyclodextrin derivatives on the diosgenin absorption in Caco-2 cell monolayer and rats. Hashimoto, F; Okawara, M; Sugibayashi, K; Todo, H; Tokudome, Y, 2014)	0.4
" The model showed that drug bioavailability was significantly improved after oral administration of cyclodextrin complexes."	( Pharmacokinetic delivery and metabolizing rate of nicardipine incorporated in hydrophilic and hydrophobic cyclodextrins using two-compartment mathematical model. Förster, C; Shityakov, S, 2013)	0.39
"Cyclodextrins are widely used excipients for increasing the bioavailability of poorly water-soluble drugs."	( Fluorescently labeled methyl-beta-cyclodextrin enters intestinal epithelial Caco-2 cells by fluid-phase endocytosis. Bácskay, I; Bacsó, Z; Fehér, P; Fenyvesi, É; Fenyvesi, F; Gutay-Tóth, Z; Malanga, M; Réti-Nagy, K; Szabó, G; Szente, L; Ujhelyi, Z; Váradi, J; Vecsernyés, M, 2014)	0.4
"The purpose of this study was to develop a new delivery system based on drug cyclodextrin (CD) complexation and loading into nanostructured lipid carriers (NLC) to improve the oral bioavailability of vinpocetine (VP)."	( A novel oral delivery system consisting in "drug-in cyclodextrin-in nanostructured lipid carriers" for poorly water-soluble drug: vinpocetine. Chen, F; Lin, C; Liu, D; Pan, W; Xiong, W; Yang, X; Ye, T; Zhang, L; Zhang, W, 2014)	0.4
"2-Hydroxypropyl-β-cyclodextrin (HPβCD) is a Food and Drug Administration-approved excipient used to improve the stability and bioavailability of drugs."	( 2-Hydroxypropyl-β-cyclodextrin promotes transcription factor EB-mediated activation of autophagy: implications for therapy. Lotfi, P; Sardiello, M; Segatori, L; Song, W; Wang, F, 2014)	0.4
" It is known that decreasing direct cell stimulation and reducing the amount applied via increasing bioavailability are useful for improving these issues."	( A nanoparticle formulation reduces the corneal toxicity of indomethacin eye drops and enhances its corneal permeability. Ito, Y; Nagai, N; Okamoto, N; Shimomura, Y, 2014)	0.4
" However, poor trans-mucosal permeability of large macromolecular antigens limits bioavailability to local inductive immune cells."	( Polymeric penetration enhancers promote humoral immune responses to mucosal vaccines. Klein, K; Mann, JF; Rogers, P; Shattock, RJ, 2014)	0.4
" In particular, it was observed that the binary complex significantly increased the solubility of furosemide form I in the gastric simulated fluid, which resulted in a rise in the bioavailability of this formulation after oral administration."	( Improving furosemide polymorphs properties through supramolecular complexes of β-cyclodextrin. Chattah, AK; Garnero, C; Longhi, M, 2014)	0.4
"Organic matter (OM) plays a vital role in controlling polycyclic aromatic hydrocarbon (PAH) bioavailability in soils and sediments."	( Hydroxypropyl-β-cyclodextrin extractability and bioavailability of phenanthrene in humin and humic acid fractions from different soils and sediments. Gao, H; Jia, L; Ma, J; Xu, L, 2014)	0.4
" The goal of loading quercetin into nanoparticles was to improve its permeation across the blood-brain barrier into the brain, and its bioavailability to reach target cells."	( Loading into nanoparticles improves quercetin's efficacy in preventing neuroinflammation induced by oxysterols. Badilli, U; Biasi, F; Calfapietra, S; Cavalli, R; Gamba, P; Gargiulo, S; Guina, T; Leonarduzzi, G; Maina, M; Poli, G; Testa, G, 2014)	0.4
"In this study, the effect of monopotassium phosphate (MKP) on the reduction in mobility and bioavailability of 2,4,6-trinitrotoluene (TNT) was tested."	( Mobility and bioavailability reduction of soil TNT via sorption enhancement using monopotassium phosphate. Jung, JW; Nam, K, 2014)	0.4
"Myricetin shows low oral bioavailability (<10%) in rats due to poor aqueous solubility, though it has various pharmacological activities."	( Development of a myricetin/hydroxypropyl-β-cyclodextrin inclusion complex: preparation, characterization, and evaluation. Hong, C; Ji, G; Li, G; Shen, H; Xie, Y; Yao, Y, 2014)	0.4
"To improve the stability and oral bioavailability of Z-ligustilide (LIG), the inclusion complex of LIG with hydroxypropyl- β-cyclodextrin (HP-β-CD) was prepared by the kneading method and characterized by UV-Vis spectroscopy, differential thermal analysis (DTA) and Fourier transform infrared (FTIR) spectroscopy."	( Complexation of Z-ligustilide with hydroxypropyl-β-cyclodextrin to improve stability and oral bioavailability. Liu, S; Lu, Y; Yu, S; Zhao, Y; Zhu, L, 2014)	0.4
" Although the bioavailability of diosgenin is low due to its poor solubility and intestinal permeability, it was subsequently improved using a β-cyclodextrin (β-CD) inclusion complex."	( Effect of liquid crystals with cyclodextrin on the bioavailability of a poorly water-soluble compound, diosgenin, after its oral administration to rats. Hashimoto, F; Okawara, M; Sugibayashi, K; Todo, H; Tokudome, Y, 2014)	0.4
" In situ intestinal re-circulating perfusion experiments showed that the absorption rate of fluorescein isothiocyanate (FITC)-labeled OVA in the distal intestine was higher than that for a marker of non-specific absorption, FITC-dextran (FD-40), and that colchicine, a general endocytosis inhibitor, suppressed OVA absorption."	( Characterization of ovalbumin absorption pathways in the rat intestine, including the effects of aspirin. Matsuo, H; Nouma, H; Yokooji, T, 2014)	0.4
"The prepared tablets with low DT and fast dissolution will prove to be a promising drug delivery system with improved bioavailability and better patient compliance."	( Development and evaluation of orally disintegrating tablets of cilostazol-β-cyclodextrin inclusion complexes. Desai, C; Prabhakar, B, 2015)	0.42
" However, the drug has the disadvantage of poor bioavailability due to its very low solubility in water; as a consequence, a very active area of research focuses on the development of new pharmaceutical formulations to increase its solubility, dissolution rate, and bioavailability."	( Characterization of albendazole-randomly methylated-β-cyclodextrin inclusion complex and in vivo evaluation of its antihelmitic activity in a murine model of Trichinellosis. García, A; Hinrichsen, LI; Lamas, MC; Leonardi, D; Vasconi, MD, 2014)	0.4
"The therapeutic efficacy of repaglinide (RPG) is limited by the low and variable oral bioavailability owing to its limited aqueous solubility."	( Preparation, characterization and in vivo evaluation of formulation of repaglinide with hydroxypropyl-β-cyclodextrin. Cao, W; He, Z; Liu, M; Sun, Y, 2014)	0.4
" These observations clearly suggested that βCD only served as the carrier to enhance the bioavailability of Phe rather than the co-substrate in the Phe biodegradation process."	( In silico understanding of the cyclodextrin-phenanthrene hybrid assemblies in both aqueous medium and bacterial membranes. Cao, Y; Gao, H; Jia, L; Ren, B, 2015)	0.42
"Cyclodextrins (CDs) are a well-known class of supermolecules that have been widely used to protect drugs against conjugation and metabolic inactivation as well as to enhance the aqueous solubility and hence to ameliorate the oral bioavailability of sparingly soluble drug molecules."	( Investigation of the interactions of silibinin with 2-hydroxypropyl-β-cyclodextrin through biophysical techniques and computational methods. Archontaki, H; Becker-Baldus, J; Chatziathanasiadou, M; Chatzigeorgiou, P; Chatzikonstantinou, AV; Glaubitz, C; Kefala, E; Kellici, TF; Leonis, G; Mavromoustakos, T; Ntountaniotis, D; Papadopoulos, MG; Tzakos, AG; Tzimas, S; Valsami, G; Viras, K, 2015)	0.42
"Cyclodextrins are commonly used as a safe excipient to enhance the solubility and bioavailability of hydrophobic pharmaceutical agents."	( Hydroxypropyl-β-cyclodextrin spikes local inflammation that induces Th2 cell and T follicular helper cell responses to the coadministered antigen. Aoshi, T; Coban, C; Homma, T; Igarashi, Y; Inoue, T; Ise, W; Ishii, KJ; Katakai, Y; Kitano, M; Kobayashi, M; Kobiyama, K; Kuroda, E; Kurosaki, T; Nakatsu, N; Ohata, K; Onishi, M; Ozasa, K; Sato, A; Standley, DM; Taniguchi, K; Vandenbon, A; Wijaya, E; Yamada, H; Yasutomi, Y, 2015)	0.42
" CCD may improve the bioavailability of phenanthrene and Pb in co-contaminated soil; CCD enhanced phytoremediation technology may be a good alternative for the removal of hydrophobic organic contaminants and heavy metals from contaminated soils."	( Cysteine-β-cyclodextrin enhanced phytoremediation of soil co-contaminated with phenanthrene and lead. Deng, N; Hu, S; Wang, G; Wang, Y; Wu, F, 2015)	0.42
"5 mg/kg dose) showed that the relative bioavailability of drug from P407/C934P gel was 11."	( Carbopol-incorporated thermoreversible gel for intranasal drug delivery. Balakrishnan, P; Cho, HJ; Hahn, TW; Ko, HJ; Park, EK; Song, CK; Song, KW, 2015)	0.42
" As pH is an essential and sensitive factor in various biological processes, a simple yet reliable pH-sensitive model such as is demonstrated here can have promising applications in the host-assisted delivery of prodrug to the target sites, such as cancer or tumour microenvironments, with an enhanced stability, bioavailability and activity, and also in the design of new fluorescent probes, sensors and smart materials for applications in nano-science."	( pH-Assisted control over the binding and relocation of an acridine guest between a macrocyclic nanocarrier and natural DNA. Pal, H; Sayed, M, 2015)	0.42
" These data indicate that ABZ:C-β-CD increases bioavailability and effectiveness of ABZ against encapsulated Trichinella larvae, thus allowing the use of small doses."	( Efficacy of albendazole:β-cyclodextrin citrate in the parenteral stage of Trichinella spiralis infection. Codina, AV; Di Masso, RJ; García, A; Hinrichsen, LI; Lamas, MC; Leonardi, D; Vasconi, MD, 2015)	0.42
"The objective of this study is to improve the solubility and oral bioavailability of CAP by reducing irritation via hydroxypropyl-β-cyclodextrin (HP-β-CD) inclusion complex formulation, in vitro and in vivo analysis."	( Preparation, characterization, and pharmacokinetics study of capsaicin via hydroxypropyl-beta-cyclodextrin encapsulation. Firempong, CK; Shi, F; Sun, C; Xu, X; Yu, J; Zhang, W; Zhao, Y, 2016)	0.43
"8 ng × h × mL(-1)) or relative bioavailability (139."	( Preparation, characterization, and pharmacokinetics study of capsaicin via hydroxypropyl-beta-cyclodextrin encapsulation. Firempong, CK; Shi, F; Sun, C; Xu, X; Yu, J; Zhang, W; Zhao, Y, 2016)	0.43
" PAH bioavailability before and after biodegradation and the joint remediation was also assessed using hydroxypropyl-β-cyclodextrin (HPCD) extraction."	( Remediation of PAH-contaminated soil at a gas manufacturing plant by a combined two-phase partition system washing and microbial degradation process. Gong, X; Gong, Z; Guo, M; Jia, C; Li, H; Li, X; Xu, X, 2015)	0.42
"The objective of the present study was to demonstrate that a novel hydroxypropyl-β-cyclodextrin functionalized calcium carbonate (HP-β-CD/CC) based amorphous solid dispersion (ASD) can be used to increase the solubility and oral bioavailability of water-insoluble drugs."	( Hydroxypropyl-β-cyclodextrin functionalized calcium carbonate microparticles as a potential carrier for enhancing oral delivery of water-insoluble drugs. Han, J; Jiang, L; Lin, Q; Zhang, L; Zhang, Y; Zhu, W, 2015)	0.42
"In order to improve oral bioavailability of tacrolimus (FK506), a novel poly(methyl vinyl ether-co-maleic anhydride)-graft-hydroxypropyl-β-cyclodextrin amphiphilic copolymer (CD-PVM/MA) is developed, combining the bioadhesiveness of PVM/MA, P-glycoprotein (P-gp), and cytochrome P450-inhibitory effect of CD into one."	( Multifunctional Poly(methyl vinyl ether-co-maleic anhydride)-graft-hydroxypropyl-β-cyclodextrin Amphiphilic Copolymer as an Oral High-Performance Delivery Carrier of Tacrolimus. Fu, Q; Guan, J; Hao, X; He, Z; Lian, H; Liu, X; Pan, X; Qi, W; Sun, J; Sun, Y; Wang, S; Wang, Y; Zhai, Y; Zhang, D, 2015)	0.42
" The aim of this study was thus to compare the pharmacokinetic characteristics and the oral bioavailability of XFSWD essential oil (XEO) and its β-CD inclusion complex after oral administration to rats."	( Preparation, Characterization and Pharmacokinetic Study of Xiangfu Siwu Decoction Essential Oil/β-Cyclodextrin Inclusion Complex. Duan, J; Guo, J; Liu, P; Pan, Y; Qian, D; Xi, J; Zhang, Y; Zhu, Z, 2015)	0.42
" Bioavailability studies showed that nanosuspensions with Odn-CICs can significantly promote the oral absorption of Odn with a relative bioavailability of 213."	( Nanosuspensions Containing Oridonin/HP-β-Cyclodextrin Inclusion Complexes for Oral Bioavailability Enhancement via Improved Dissolution and Permeability. Lan, Y; Shi, Z; Wu, B; Zhang, T; Zhang, X, 2016)	0.43
"Silibinin, the main active component of Silybum marianum is a hepatoprotective and antioxidant agent with antitumor effect, exhibiting very low aqueous solubility and oral bioavailability limiting its use in therapeutics."	( Serum and tissue pharmacokinetics of silibinin after per os and i.v. administration to mice as a HP-β-CD lyophilized product. Archontaki, H; Balafas, E; Christodoulou, E; Dokoumetzidis, A; Kechagia, IA; Kostomitsopoulos, N; Tzimas, S; Valsami, G, 2015)	0.42
" The aim of this study was to improve the low solubility, slow dissolution rate and low oral bioavailability of compound K by forming an inclusion complex with γ-cyclodextrin (γ-CyD), and to compare the results with those of β-CyD complex."	( The formation of an inclusion complex between a metabolite of ginsenoside, compound K and γ-cyclodextrin and its dissolution characteristics. Anraku, M; Hirayama, F; Igami, K; Inoue, S; Iohara, D; Miyazaki, T; Ozawa, M; Shinoda, M; Uekama, K, 2016)	0.43
" Furthermore, PSC showed higher bioavailability in rats after intravenous administration than PTX solution; however, no significant differences in kidney toxicity were observed."	( Modification of paclitaxel-loaded solid lipid nanoparticles with 2-hydroxypropyl-β-cyclodextrin enhances absorption and reduces nephrotoxicity associated with intravenous injection. Baek, JS; Cho, CW; Kim, JH; Park, JS, 2015)	0.42
" Moreover, the use of these effervescent tablets in an orodispersible dosage form can improve oral drug bioavailability and act as an attractive pediatric dosage form."	( Novel levocetirizine HCl tablets with enhanced palatability: synergistic effect of combining taste modifiers and effervescence technique. Labib, GS, 2015)	0.42
" In vivo studies indicated that the formulated tablets had 2 times higher bioavailability than marketed tablets."	( Formulation of cyclodextrin inclusion complex-based orally disintegrating tablet of eslicarbazepine acetate for improved oral bioavailability. Desai, S; Poddar, A; Sawant, K, 2016)	0.43
" The relatively improved oral bioavailability and better antitumour efficacy indicated that the dual-drug CD/CS NPs developed in our study possessed significant advantages and might be a promising strategy for the development of drug, delivery systems for cancer chemotherapy."	( Co-Delivery of Docetaxel and Berbamine by Chitosan/Sulfobutylether-β-Cyclodextrin Nanoparticles for Enhancing Bioavailability and Anticancer Activities. Bu, X; Dou, L; Fang, L; Shen, Q; Wu, J, 2015)	0.42
" Despite the potential use of Qu in clinical trials, low water solubility, stability problems and the scarcity of cellular bioavailability limit its applications."	( Characterization and Antioxidant Activity of Quercetin/Methyl-β-Cyclodextrin Complexes. Demirel, M; Güleç, K, 2016)	0.43
"The stability and bioavailability of catechins, a kind of tea polyphenols with health benefit, could be improved by complexing with cyclodextrins."	( Improved stability of (+)-catechin and (-)-epicatechin by complexing with hydroxypropyl-β-cyclodextrin: Effect of pH, temperature and configuration. Han, J; Liu, M; Niu, M; Sun, D; Wang, B; Wang, C; Wang, Z; Xie, J; Zheng, Y, 2016)	0.43
" βLAP (and its combinations with CDs) absorption rate coefficients and effective permeability values have been determined in vitro in MDCK or MDCK-Mdr1 monolayers and in situ in rat by a closed loop perfusion technique."	( Intestinal Permeability of β-Lapachone and Its Cyclodextrin Complexes and Physical Mixtures. Bermejo, M; Casabó, VG; Echezarreta-López, M; González-Álvarez, I; González-Álvarez, M; Gutiérrez-Nieto, J; Landin, M; Mangas-Sanjuan, V, 2016)	0.43
" Accordingly, it can be speculated that cyclodextrin inclusion complex can improve bioavailability of poorly water-soluble drugs."	( [Effect of β-cyclodextrin inclusion complex on transport of major components of Xiangfu Siwu decoction essential oil in Caco-2 cell monolayer model]. Duan, JA; Liu, P; Qian, DW; Xi, JZ; Zhang, L; Zhu, Y; Zhu, ZH, 2015)	0.42
" Pharmacokinetic studies of danazol in rats showed a significant longer Tmax and decreased Cmax resulting in decreased bioavailability when the CD concentration was increased."	( Effect of cyclodextrin concentration on the oral bioavailability of danazol and cinnarizine in rats. Hartvig, RA; Holm, R; Jørgensen, EB; Larsen, DB; Olesen, NE; Westh, P, 2016)	0.43
" The bioavailability improvement for dry suspensions with RLX-HICs can be attributed to improved dissolution and physiochemical properties of RLX, by which the overall absorption was enhanced."	( Enhanced bioavailability of raloxifene hydrochloride via dry suspensions prepared from drug/HP-β-cyclodextrin inclusion complexes. Li, X; Liu, S; Lu, R; Wang, Q, 2015)	0.42
"To date, improving oral bioavailability of water-soluble drugs with poor membrane permeability is still challenging."	( Polymersomes via Self-Assembly of Amphiphilic β-Cyclodextrin-Centered Triarm Star Polymers for Enhanced Oral Bioavailability of Water-Soluble Chemotherapeutics. Hu, M; Qiu, L; Shen, Y; Zhang, L, 2016)	0.43
" However, its oral bioavailability is greatly limited by the dissolution rate of the drug."	( Characterization and In Vitro Evaluation of the Complexes of Posaconazole with β- and 2,6-di-O-methyl-β-cyclodextrin. Li, H; Liao, X; Ma, X; Tang, P; Wang, L; Xiong, X; Xu, K, 2017)	0.46
" Moreover, results of studies investigating the characteristics of progesterone and cyclodextrins showed that the new formulation (progesterone/HPβCD 25 mg solution) has the same bioavailability as other products containing progesterone."	( Efficacy and Safety Profile of Diclofenac/Cyclodextrin and Progesterone/Cyclodextrin Formulations: A Review of the Literature Data. Bonagura, AC; Cenami, R; Cimmaruta, D; Fiorentino, S; Fossati, T; Rossi, F; Scavone, C; Torella, M, 2016)	0.43
" Finally, the use of cyclodextrins led to significant increases in solubility and bioavailability of drugs, such as diclofenac and progesterone, and improvement in the efficacy and safety of these drugs."	( Efficacy and Safety Profile of Diclofenac/Cyclodextrin and Progesterone/Cyclodextrin Formulations: A Review of the Literature Data. Bonagura, AC; Cenami, R; Cimmaruta, D; Fiorentino, S; Fossati, T; Rossi, F; Scavone, C; Torella, M, 2016)	0.43
"To develop a new vaginal delivery system for a sustained release of dehydroepiandrosterone (DHEA) in the treatment of postmenopausal symptoms, aimed to overcome the problems of poor bioavailability of the drug related to its very low water solubility."	( Development of cyclodextrin hydrogels for vaginal delivery of dehydroepiandrosterone. Casella, G; Cirri, M; Maestrelli, F; Mennini, N; Mura, P, 2016)	0.43
" In the case of acyclovir, Cap-Na either alone or in combination with SLS or chitosan has the potential to improve its absorption and bioavailability and has yet to be explored."	( Effect of permeability enhancers on paracellular permeability of acyclovir. Ates, M; Kaynak, MS; Sahin, S, 2016)	0.43
" The relative bioavailability of evodiamine inclusion complex was 256."	( [A preliminary study of pharmacokinetics of evodiamine hydroxypropyl-β-cyclodextrin inclusion complex]. Feng, J; Lei, TT; Liu, HM; Zhang, JQ; Zhang, X, 2016)	0.43
" However, its hydrophobic nature affects its bioavailability and bioactivity, and limits nutraceutical applications."	( Synergistic radical scavenging potency of curcumin-in-β-cyclodextrin-in-nanomagnetoliposomes. Aadinath, W; Anandharamakrishnan, C; Bhushani, A, 2016)	0.43
" Here, a physical method (mechanical mixing) and a chemical method (randomly methylated-β-cyclodextrins, RAMEB) were adopted to improve the bioavailability and biodegradation of polychlorinated biphenyls (PCBs) of an aged soil."	( Effects of RAMEB and/or mechanical mixing on the bioavailability and biodegradation of PCBs in soil/slurry. Hashmi, MZ; Hu, J; Qin, Z; Shen, C; Shi, J; Su, X; Wang, H; Wang, Y; Yu, C, 2016)	0.43
" Therefore, we suggest that the present cysteinyl β-CD is a potential host molecule for inclusion complexation and for bioavailability augmentation."	( Characterization and Enhanced Antioxidant Activity of the Cysteinyl β-Cyclodextrin-Baicalein Inclusion Complex. Cho, E; Jung, S; Kim, H; Lee, JY; Park, S; Yiluo, H, 2016)	0.43
" The positive impact of surfactants on pyrene remediation could possibly be because of their capacities to increase its bioavailability in soil."	( Surfactant enhanced pyrene degradation in the rhizosphere of tall fescue (Festuca arundinacea). Cheema, SA; Chen, Y; Farooq, M; Khan, MI; Shen, C; Tang, X, 2016)	0.43
" The in vitro release study indicated that Nag-CD/CS-NPs achieved moderate sustained-release effect, and the in vivo study revealed that the prepared nanoparticles was nonirritating to rabbit's eye and had better ability to prolong the residence time than the naringenin suspension, which can significantly increase naringenin bioavailability in the aqueous humor."	( Preparation and evaluation of naringenin-loaded sulfobutylether-β-cyclodextrin/chitosan nanoparticles for ocular drug delivery. Bai, Y; Hu, W; Liu, X; Zhang, L; Zhang, P, 2016)	0.43
" The relative bioavailability was researched by comparing the area under the plasma concentration-time curve of 16-DHP-HP-β-CD and free 16-DHP after oral administration in rats at the dose of 75 mg/kg."	( Pharmacokinetics of 16-dehydropregnenolone hydroxypropyl-β-cyclodextrin inclusion complex following peroral administration. Jia, L; Mao, M; Sun, L; Sun, Y; Wang, X; Wei, L; Zhou, H, 2017)	0.46
" However, curcumin is neither well absorbed nor well retained in the blood, resulting in low efficacy."	( Synthesis and Characterization of Curcumin-Functionalized HP-β-CD-Modified GoldMag Nanoparticles as Drug Delivery Agents. Cui, Y; Hou, P; Jin, Y; Lian, T; Luo, Z; Peng, M; Van de Ven, WJ; Vermorken, AJ; Wan, Y, 2016)	0.43
"AHHPs can improve the bioavailability of AAS, extending its biological half-life in rats."	( [Pharmacokinetics and Bioequiavailability of Asparaginase in Asparaginase Nanospheres]. Deng, X; Hu, XY; Li, WY; Wang, SL; Yan, ZJ; Zhang, JQ, 2016)	0.43
" Yet, its ocular bioavailability is hindered by its poor aqueous solubility."	( Potential Use of Cyclodextrin Complexes for Enhanced Stability, Anti-inflammatory Efficacy, and Ocular Bioavailability of Loteprednol Etabonate. El-Dahan, MS; Khatera, NAA; Mohamed, EAM; Soliman, OAE, 2017)	0.46
" The formula had a relative bioavailability of 125."	( Effect of different polymers on avanafil-β-cyclodextrin inclusion complex: in vitro and in vivo evaluation. Ghorab, MM; Ibrahim, HK; Soliman, KA, 2016)	0.43
" However, its medicinal applications were severely impeded by the poor water solubility and resultant low bioavailability and potency."	( Solid inclusion complexes of oleanolic acid with amino-appended β-cyclodextrins (ACDs): Preparation, characterization, water solubility and anticancer activity. Gao, K; Liao, X; Liu, Y; Niu, R; Ren, Y; Yang, B; Yang, Z; Zhang, J, 2016)	0.43
" Ternary nanosponge complexes were found to have 2-fold increase in oral bioavailability of efavirenz as compared to plain drug."	( Enhancement of Bioavailability of Non-nucleoside Reverse Transciptase Inhibitor Using Nanosponges. Rao, MRP; Shirsath, C, 2017)	0.46
" The objectives of this study were to improve the solubility and bioavailability in fasted state and to reduce the food effect of AMD by producing its inclusion complex with sulfobutylether-β-cyclodextrin (SBE-β-CD)."	( Preparation and Characterization of the Sulfobutylether-β-Cyclodextrin Inclusion Complex of Amiodarone Hydrochloride with Enhanced Oral Bioavailability in Fasted State. Chen, G; Ren, L; Wang, D, 2017)	0.46
"Paclitaxel (PTX), a hydrophobic anticancer drug, is facing several clinical limitations such as low bioavailability and drug resistance."	( Thermoresponsive Delivery of Paclitaxel by β-Cyclodextrin-Based Poly(N-isopropylacrylamide) Star Polymer via Inclusion Complexation. Li, J; Song, X; Wen, Y; Zhang, ZX; Zhao, F; Zhu, JL, 2016)	0.43
" The aim of this work was to evaluate the capability of nanoencapsulated quercetin in zein nanoparticles (NPQ), that significantly improves the oral absorption and bioavailability of the flavonoid, as potential oral treatment for AD."	( Effect of the oral administration of nanoencapsulated quercetin on a mouse model of Alzheimer's disease. Irache, JM; Moreno, LCGEI; Puerta, E; Ramirez, MJ; Santos-Magalhães, NS; Suárez-Santiago, JE, 2017)	0.46
" In order to obtain an improvement of the bioavailability and solubility of 5-fluorouracil, a pyrimidine analogue used as chemotherapeutic agent in the treatment of the colon, liver, and stomac cancers, the drug was complexed with alpha- and beta-cyclodextrin."	( Alpha- and Beta-Cyclodextrin Inclusion Complexes with 5-Fluorouracil: Characterization and Cytotoxic Activity Evaluation. Di Donato, C; Fattorusso, R; Iacovino, R; Isernia, C; Isidori, M; Lavorgna, M; Malgieri, G; Piscitelli, C; Russo, C; Russo, L, 2016)	0.43
" Compared with a VRC solution, the nanofibers significantly prolonged the half life, and increased the bioavailability of VRC in rabbit tears."	( Voriconazole Composited Polyvinyl Alcohol/Hydroxypropyl-β-Cyclodextrin Nanofibers for Ophthalmic Delivery. Cai, Z; Lv, Y; Sun, X; Yu, L; Yu, Z, 2016)	0.43
" In order to solve these problems, an inclusion complex using hydroxypropyl-β-cyclodextrin (HP-β-CD) to improve the oral bioavailability of Da was prepared successfully by freeze-drying."	( Preparation, characterization and in vivo evaluation of a formulation of dantrolene sodium with hydroxypropyl-β-cyclodextrin. Chen, M; Jiang, J; Jin, X; Liu, S; Wang, M; Wu, Q; Zhao, C, 2017)	0.46
"Several targeted drug delivery systems have recently been developed to increase the bioavailability of a drug at its site of action, allowing simultaneous reduction of the total necessary drug dose as well as side effects."	( PEGylated Cationic Vectors Containing a Protease-Sensitive Peptide as a miRNA Delivery System for Treating Breast Cancer. Fan, M; Gong, T; Sun, X; Zeng, Y; Zhang, Z; Zhou, Z, 2017)	0.46
" The aim of the present study is to improve the oral bioavailability of FST by encapsulating into PLGA NPs (poly-lactide-co-glycolic acid nanoparticles) as a complex of HPβCD (hydroxyl propyl beta cyclodextrin) and to assess its anti-cancer activity against breast cancer cells."	( Enhanced oral bioavailability and anticancer efficacy of fisetin by encapsulating as inclusion complex with HPβCD in polymeric nanoparticles. Bhandi, MM; Borkar, RM; Gudem, S; Kadari, A; Kolapalli, VR; Kulhari, H; Sistla, R, 2017)	0.46
" In vivo distribution and antitumor studies revealed that the bioavailability of RG-β-CD was increased when β-CD mated with RG."	( Evaluation of molecular chaperone drug function: Regorafenib and β-cyclodextrins. Hu, X; Li, Y; Sun, M; Tang, G, 2017)	0.46
" This oil is important therapeutically, but the low solubility and bioavailability compromises your use."	( Physico-chemical characterization and antibacterial activity of inclusion complexes of Hyptis martiusii Benth essential oil in β-cyclodextrin. Andrade, TA; Araújo, AAS; Araújo, FO; Bezerra, DP; Campina, FF; Costa, MS; Coutinho, HDM; Dória, GAA; Freitas, TS; Menezes, IRA; Menezes, PP; Nunes, PS; Quintans-Júnior, LJ; Rabelo, AS; Santos, ATL; Santos, MRV; Serafini, MR; Silva, ARP, 2017)	0.46
"Cyclodextrins (CDs) are cyclic oligosaccharides can enhance the bioavailability of drugs."	( Anti-inflammatory activity of the essential oil obtained from Ocimum basilicum complexed with β-cyclodextrin (β-CD) in mice. Araújo, AAS; Cesário, FRAS; Coutinho, HDM; da Silva, BAF; de Albuquerque, TR; de Menezes, IRA; E Castro, FF; Fernandes, MNM; Goncalves Wanderley, A; Martins, AOBPB; Matos, IG; Menezes, PDP; Nunes, PS; Quintans Júnior, LJ; Ribeiro-Filho, J; Rodrigues, LB, 2017)	0.46
" This study investigated the complexation effect of mono-6-deoxy-6-aminoethylamino-β-cyclodextrin on the aqueous solubility and bioavailability of ciprofloxacin."	( Solubility and bioavailability enhancement of ciprofloxacin by induced oval-shaped mono-6-deoxy-6-aminoethylamino-β-cyclodextrin. Cho, E; Choi, JM; Choi, Y; Dindulkar, SD; Jeong, D; Jung, S; Lee, B; Park, K; Park, S; Yu, JH, 2017)	0.46
"The bioavailability of the anthelminthic flubendazole was remarkably enhanced in comparison with the pure crystalline drug by developing completely amorphous electrospun nanofibres with a matrix consisting of hydroxypropyl-β-cyclodextrin and polyvinylpyrrolidone."	( Oral bioavailability enhancement of flubendazole by developing nanofibrous solid dosage forms. Balogh, A; Boeykens, P; Borbás, E; Démuth, B; Galata, DL; Mackie, C; Marosi, G; Nagy, ZK; Pataki, H; Psathas, P; Van Assche, I; Van Hove, B; Verreck, G; Vialpando, M; Vigh, T, 2017)	0.46
" However, the low solubility and bioavailability of AG lead to high doses and long-term therapy."	( Inhalable Andrographolide-β-cyclodextrin Inclusion Complexes for Treatment of Staphylococcus aureus Pneumonia by Regulating Immune Responses. Han, G; Hu, Y; Jiang, Q; Jin, Y; Li, M; Zhang, E; Zhang, T; Zhu, L, 2017)	0.46
" The bioavailability of these compounds depends among others on their interactions with other components of the diet, mainly proteins."	( Influence of the Form of Administration of Chlorogenic Acids on Oxidative Stress Induced by High fat Diet in Rats. Budryn, G; Grzelczyk, J; Juśkiewicz, J; Zaczyńska, D; Zduńczyk, Z; Żyżelewicz, D, 2017)	0.46
" Moreover, in vivo study showed that HK-CS-NPs exhibited good ocular tolerability and could improve ophthalmic bioavailability of honokiol."	( Development of a Chitosan-based Nanoparticle Formulation for Ophthalmic Delivery of Honokiol. Chen, H; Deng, F; Hu, W; Tang, Y; Zhang, L, 2018)	0.48
" Pharmacokinetic parameters displayed a higher absorption rate and higher area under the curve of the FIN/DM-β-CyD inclusion complex when compared with the drug alone, which indicates an improvement in the absorption and bioavailability of FIN in the DM-β-CyD inclusion system."	( Experimental, molecular docking investigations and bioavailability study on the inclusion complexes of finasteride and cyclodextrins. Farghaly Aly, U; Mady, FM, 2017)	0.46
"Cyclodextrins (CDs) can improve the apparent solubility and bioavailability of a variety of organic compounds through the formation of inclusion complexes; accordingly, they are suitable for application in innovative remediation technologies of contaminated soils."	( Influence of selected cyclodextrins in sorption-desorption of chlorpyrifos, chlorothalonil, diazinon, and their main degradation products on different soils. Báez, ME; Espinoza, J; Fuentes, E; Silva, R, 2017)	0.46
"Glibenclamide is an antidiabetic drug showing low bioavailability as consequence of its low solubility."	( Supramolecular structure of glibenclamide and β-cyclodextrins complexes. Font, M; Irache, JM; Lucio, D; Martínez-Ohárriz, MC, 2017)	0.46
"To synthesize β cyclodextrin nanosponges using a novel and efficient microwave mediated method for enhancing bioavailability of Rilpivirine HCl (RLP)."	( Enhancement of oral bioavailability of anti-HIV drug rilpivirine HCl through nanosponge formulation Momin, M; Sangshetti, JN; Zaheer, Z; Zainuddin, R, 2017)	0.46
" It is poorly absorbed when administered orally, hence exhibits poor oral bioavailability, which limits its use in clinical practice."	( Preferential Formulation of Second Generation Antipsychotic Asenapine as Inclusion Complex with Sulphobutylether-βCD (Captisol): In vitro and In vivo Evaluation. Avachat, AM; Avachat, CM; Coutinho, EC; Khan, EM; Kulkarni, JA; Martis, EAF; Padhye, S; Pradhan, R; Suryawanshi, TS, 2018)	0.48
"This study thus demonstrated that Captisol® inclusion complex is an effective strategy for solubility and bioavailability enhancement of asenapine."	( Preferential Formulation of Second Generation Antipsychotic Asenapine as Inclusion Complex with Sulphobutylether-βCD (Captisol): In vitro and In vivo Evaluation. Avachat, AM; Avachat, CM; Coutinho, EC; Khan, EM; Kulkarni, JA; Martis, EAF; Padhye, S; Pradhan, R; Suryawanshi, TS, 2018)	0.48
"The ocular bioavailability of lipophilic drugs, such as dexamethasone, depends on both drug water solubility and mucoadhesion/permeation."	( A water-soluble, mucoadhesive quaternary ammonium chitosan-methyl-β-cyclodextrin conjugate forming inclusion complexes with dexamethasone. Balzano, F; Burgalassi, S; Chetoni, P; Fabiano, A; Monti, D; Piras, AM; Tampucci, S; Terreni, E; Uccello-Barretta, G; Zambito, Y, 2018)	0.48
" A new potential approach for solubility, bioavailability and permeability enhancement of acyclovir and other BCS class IV drugs was successfully established."	( FORMULATION AND IN VITRO EVALUATION OF ACYCLOVIR LOADED POLYMERIC MICROPARTICLES: A SOLUBILITY ENHANCEMENT STUDY. Ahmad, M; Mahmood, A; Minhas, MU; Sarfraz, RM; Yaqoob, A, 2016)	0.43
" However, this widely used AT1 antagonist presents low bioavailability and needs once or twice a day dosage."	( A long-lasting oral preformulation of the angiotensin II AT1 receptor antagonist losartan. Braga, ANG; De Paula, WX; Denadai, ÂML; Frezard, F; Pinheiro, SVB; Santos, RAS; Shastri, VP; Sinisterra, RD, 2018)	0.48
"Simvastatin is poorly bioavailable because it is practically insoluble in water and shows dissolution rate-limited absorption."	( Preparation and characterization of simvastatin/DMβCD complex and its pharmacokinetics in rats. Fan, H; Gu, F; Ning, J; Wang, Y; Wu, C, 2018)	0.48
" Cyclodextrins (CDs) have been proposed as an alternative in remediation technologies based on the separation of contaminants from soils because they could allow a higher bioavailability for their degradation with a low environmental impact."	( Degradation kinetics of chlorpyrifos and diazinon in volcanic and non-volcanic soils: influence of cyclodextrins. Báez, ME; Espinoza, J; Fuentes, E, 2018)	0.48
"The development of biomaterials for a range of tissue engineering applications increasingly requires control over the bioavailability of biomolecular cues such as growth factors in order to promote desired cell responses."	( Incorporating β-cyclodextrin into collagen scaffolds to sequester growth factors and modulate mesenchymal stem cell activity. Grier, WK; Harley, BAC; Ramsey, MD; Tiffany, AS, 2018)	0.48
"NOR:HPβCD:GA was the best approach for improving the bioavailability of NOR."	( Binary and ternary complexes of norfloxacin to improve the solubility of the active pharmaceutical ingredient. Aloisio, C; Garnero, C; Gracia-Vásquez, S; Longhi, M; Ponce-Ponte, M; Romero-Guerra, DM, 2018)	0.48
" These results suggested that the newly synthesized derivative of CD can be used as a complexing agent to enhance the bioavailability of flavonoids such as baicalein, especially in restoring collagen synthesis."	( Inclusion complexes of cysteinyl β-cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure. Ahn, E; Ahn, S; Cho, E; Jung, S; Kim, H; Kim, SY; Lee, J; Park, S; Shin, Y; Sung, J, 2019)	0.51
" Such an improved cytotoxic effect can be attributed to the enhanced the aqueous solubility and bioavailability of carvacrol by effective complexation in β-cyclodextrin."	( Carvacrol/β-cyclodextrin inclusion complex inhibits cell proliferation and migration of prostate cancer cells. Araújo, AAS; Bertassoni, LE; Bezerra, DP; Carvalho, YMBG; Duarte, MC; França, CM; Lima, BS; Menezes, PP; Quintans-Júnior, LJ; Shanmugam, S; Souza, EPBSS; Thrivikraman, G; Trindade, GGG, 2019)	0.51
"Microencapsulation protects core materials from deteriorating due to environmental conditions, such as moisture or oxidation, and improves the bioavailability of active compounds, allowing one to make solid formulations from oils and increase their solubility."	( Impact of Gelatin Supplemented with Gum Arabic, Tween 20, and β-Cyclodextrin on the Microencapsulation of Turkish Oregano Extract. Baranauskaite, J; Bernatoniene, J; Kopustinskiene, DM, 2019)	0.51
" However, its low solubility in water and its bioavailability could hamper its practical applications."	( Encapsulation of inuloxin A, a plant germacrane sesquiterpene with potential herbicidal activity, in β-cyclodextrins. Boari, A; Cimmino, A; Evidente, A; Masi, M; Moeini, A; Tarallo, O; Vurro, M; Zonno, MC, 2019)	0.51
" It also improves oral bioavailability and increases the safety of a drug by targeting at a specific site with less side effects."	( Nanostructured cochleates: a multi-layered platform for cellular transportation of therapeutics. Gaud, RS; Khair, R; Shende, P, 2019)	0.51
" The main problem associated with the major bioactive lignans oral administration is low oral bioavailability due to the lignans' poor aqueous solubility and taste."	( Pharmacokinetics and liver uptake of three Schisandra lignans in rats after oral administration of liposome encapsulating β-cyclodextrin inclusion compound of Schisandra extract. Chen, W; Ding, Z; Guo, Y; Hu, J; Jiang, Y; Xiao, J; Zhang, B; Zhang, Y, 2019)	0.51
" However, GLA presents poor solubility in water and low bioavailability through oral administration which has hindered its application in the clinic."	( Preparation, optimization of the inclusion complex of glaucocalyxin A with sulfobutylether-β-cyclodextrin and antitumor study. Chen, G; Ren, L; Wang, J, 2019)	0.51
" Spray-drying increases the bioavailability of the natural active compounds and improves the solubility of low-soluble compounds."	( Microencapsulation of Bernatoniene, J; Ivanauskas, L; Jakstas, V; Kopustinskiene, DM; Marksa, M; Pudziuvelyte, L, 2019)	0.51
"An aqueous dispersion of alpha-lipoic acid (ALA) using octenylsuccinic anhydride-modified high-amylose starch (OS) was prepared, and thermal stability and cellular bioavailability of ALA were compared with those prepared using native high-amylose starch (HA) and beta-cyclodextrin (β-CD)."	( Enhanced bioavailability of alpha-lipoic acid by complex formation with octenylsuccinylated high-amylose starch. Kim, YJ; Lee, SJ; Li, YX; Lim, ST; Reddy, CK, 2019)	0.51
" According to the results of this study, the system can serve as a promising non-spherical delivery vehicle for enhancing bioavailability and targeting of hydrophobic anticancer agents in the future."	( Flower-like curcumin-loaded folic acid-conjugated ZnO-MPA- βcyclodextrin nanostructures enhanced anticancer activity and cellular uptake of curcumin in breast cancer cells. Fakhroueian, Z; Ghaffari, SB; Khorramizadeh, MR; Sarrafzadeh, MH, 2019)	0.51
" Nevertheless, the highly lipophilic nature and poor bioavailability prevent its application in daily clinical practice thus leading to a limited therapeutic value of hypericin."	( Hypericin inclusion complexes encapsulated in liposomes for antimicrobial photodynamic therapy. Bakowsky, U; Brüßler, J; Duse, L; Jedelska, J; Pinnapireddy, SR; Plenagl, N; Seitz, BS, 2019)	0.51
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51
" In conclusion, the Norfloxacin oral bioavailability can be improved with this binary systems, that could be applied in the production of an alternative pharmaceutical formulation of the drug."	( β-cyclodextrin complexation as an approach to enhance the biopharmaceutical properties of Norfloxacin B Hydrate. Bongioanni, A; Bueno, MS; Chierentin, L; Garnero, C; Longhi, MR; Nunes Salgado, HR, 2019)	0.51
"In spite of their extensive medicinal properties, cur and curcuminoids have poor solubility and bioavailability due to their hydrophobicity."	( Curcumin-C3 Complexed with α-, β-cyclodextrin Exhibits Antibacterial and Antioxidant Properties Suitable for Cancer Treatments. Huang, FY; Kumar, R; Reddy, DNK; Wang, SP, 2019)	0.51
"Lipid-based delivery systems (LBDSs) are widely applied in pharmaceuticals and health care because of the increased bioavailability of lipophilic components when they are coadministered with high-fat meals."	( pH-Responsive Emulsions with β-Cyclodextrin/Vitamin E Assembled Shells for Controlled Delivery of Polyunsaturated Fatty Acids. Lu, X; Luo, Z; Qi, L; Xi, Y; Zou, Y, 2019)	0.51
" The formation of these complexes in general, increases the solubility, stability, dissolution rate, and bioavailability of drugs with poor water solubility."	( Paclitaxel/β-Cyclodextrin interactions, a perspective from pulsed NMR spectroscopy experiments. Buera, MP; Ferreyra, MG; Luna, JA; Mengatto, LN; Santagapita, PR; Velázquez, NS, 2019)	0.51
"The aqueous solubility of drug molecules is closely related to its bioactivity like bioavailability and subsequent therapeutic index, especially in the case of hydrophobic drugs like camptothecin (CPT), a potential broad-spectrum anti-cancer agent."	( Lytic peptide-grafted beta-cyclodextrin polymer based nano-scaled drug delivery system with enhanced camptothecin anti-cancer efficacy. Li, T; Liu, Y; Muhammad, N; Wang, J; Zhan, H; Zhao, H, 2020)	0.56
" In order to improve dissolution, bioavailability and sustained release of Thiamine, we prepared Thiamine hydrochloride (TH) and beta-cyclodextrin (β-CD) host-guest solid inclusion complexes by microwave irradiation and studied the chemical characteristics and drug delivery potential of the complex."	( Controlled release of vitamin B Jindal, D; Jindal, R; Kaur, K, 2020)	0.56
" However, its physicochemical characteristics and poor oral bioavailability have been limiting factors for its pharmaceutical development."	( Complexation with β-cyclodextrin enhances apoptosis-mediated cytotoxic effect of harman in chemoresistant BRAF-mutated melanoma cells. Almeida, JRGDS; Beaugeard, L; de Alencar Filho, EB; de Oliveira Júnior, RG; de Oliveira, AP; Ferraz, CAA; Groult, H; Nunes, XP; Picot, L, 2020)	0.56
" However, due to its poor solubility and instability in physiological conditions, the bioavailability of CUR is limited."	( Doxorubicin and CD‑CUR inclusion complex co‑loaded in thermosensitive hydrogel PLGA‑PEG‑PLGA localized administration for osteosarcoma. Liu, J; Lu, Y; Yang, Z, 2020)	0.56
"Chemotherapeutic drugs for colorectal cancer(CRC) which is currently the third most lethal cancer globally, are administered intravenously (iv) due to their low oral bioavailability resulting from their physicochemical properties."	( Cyclodextrin nanoparticle bound oral camptothecin for colorectal cancer: Formulation development and optimization. Aktaş, Y; Benito, JM; Bilensoy, E; Ünal, S, 2020)	0.56
" However, it has low solubility in water which compromises the absorption in the gastrointestinal tract, decreases the bioavailability and compromises the reproducibility of the effects in vivo."	( Ethyl ferulate/β-cyclodextrin inclusion complex inhibits edema formation. Braz, EM; Coêlho, AG; Cunha, FVM; da Silva Azevedo, PS; de Assis Oliveira, F; de Rezende, DC; de Sousa, DP; do Nascimento Caldas Trindade, G; Nunes, LCC; Pereira de Sousa Neto, B, 2020)	0.56
"Although some drug-based supramolecular systems have been constructed to overcome multidrug resistance and enhance the bioavailability of chemical drugs, strengthening the specific stimuli-responsive and active targeting ability of these systems is still a major challenge."	( β-Cyclodextrin-modified hyaluronic acid-based supramolecular self-assemblies for pH- and esterase- dual-responsive drug delivery. Bai, Y; Bu, HT; Chen, D; Li, H; Liu, CF; Liu, CP; Tian, W; Wang, C; Zhuo, LH, 2020)	0.56
" However, its poor solubility and low bioavailability severely limits its application."	( Evaluation of anticancer activity of honokiol by complexation with hydroxypropyl-β-cyclodextrin. Wu, W; Xue, W, 2020)	0.56
" Due to the low aqueous solubility and low bioavailability of curcumin, cyclodextrins (CDs) were applied and complexed with curcumin to obtain CMx."	( The potential use of curcumin-β-cyclodextrin inclusion complex/chitosan-loaded cellulose sponges for the treatment of chronic wound. Kiti, K; Suwantong, O, 2020)	0.56
" Que's oral bioavailability is limited by its low water solubility and extended peripheral metabolism; thus, nasal administration may be a promising alternative to achieve effective Que concentrations in the brain."	( Preparation and Biophysical Characterization of Quercetin Inclusion Complexes with β-Cyclodextrin Derivatives to be Formulated as Possible Nose-to-Brain Quercetin Delivery Systems. Andreadelis, I; Athanasiadou, I; Banella, S; Chatziathanasiadou, MV; Chountoulesi, M; Colombo, G; Dallas, P; Demetzos, C; Diamantis, DA; Javornik, U; Manta, K; Mavromoustakos, T; Moschovou, K; Naziris, N; Papakyriakopoulou, P; Plavec, J; Rekkas, DM; Spaneas, D; Tzakos, AG; Vakali, V; Valsami, G, 2020)	0.56
"In the present work binding affinities and interactions between various anti-cancerous drugs and β- cyclodextrin using molecular docking simulations was examined for the bioavailability enhancement of cytotoxic drugs through improved solubility for the treatment of breast cancer."	( In Silico Docking of Anti Cancerous Drugs with β-Cyclodextrin polymer as a Prominent Approach to Improve the Bioavailability. Jain, AK; Mishra, K; Thareja, S, 2021)	0.62
" The inclusion compound showed a higher inhibiting growth of Candida albicans than the free complex [Ag(phen)2]salH indicating that the formation of the inclusion complex with β-CD increases the bioavailability of the antimicrobial active species [Ag(phen)2]+ of the new silver(I) compound."	( Partial inclusion of bis(1,10-phenanthroline)silver(I) salicylate in β-cyclodextrin: Spectroscopic characterization, in vitro and in silico antimicrobial evaluation. Almeida, VL; BriÑez-Ortega, E; Burgos, AE; Lopes, JCD, 2020)	0.56
" To address the limitation of its poor oral bioavailability and low local concentration in the lung, a naringenin-HPβCD inhalation solution was prepared for pulmonary delivery."	( Aerosolization Performance, Antitussive Effect and Local Toxicity of Naringenin-Hydroxypropyl-β-Cyclodextrin Inhalation Solution for Pulmonary Delivery. Fan, W; Guan, M; Shi, R; Su, W; Zeng, X; Zheng, Y, 2021)	0.62
" The oral bioavailability of progesterone in rats was increased 5-fold when administered with the optimized formulation compared to administration with progesterone API capsules."	( Optimization of sulfobutyl-ether-β-cyclodextrin levels in oral formulations to enhance progesterone bioavailability. Cuny, ZG; Doerksen, RJ; Murthy, SN; Pandey, P; Police, A; Repka, MA; Shankar, VK, 2021)	0.62
" The supramolecular adduct of RSP with RM-β-CD represents a valuable candidate for further research in developing new formulations with enhanced bioavailability and stability, and the results of this study allow a pertinent selection of three excipients that can be incorporated in solid dosage forms."	( Risperidone/Randomly Methylated β-Cyclodextrin Inclusion Complex-Compatibility Study with Pharmaceutical Excipients. Barvinschi, P; Cîrcioban, D; Ledeți, A; Ledeți, I; Miclău, M; Sbârcea, L; Suciu, O; Tănase, IM; Văruţ, RM; Vlase, G, 2021)	0.62
"Self-aggregation of Curcumin (Cur) in aqueous biological environment decreases its bioavailability and in vivo therapeutic efficacy, which hampers its clinical use as candidate for reducing risk of neurodegenerative diseases."	( Synthesis of New Water Soluble β-Cyclodextrin@Curcumin Conjugates and In Vitro Safety Evaluation in Primary Cultures of Rat Cortical Neurons. Acherar, S; Arab-Tehrany, E; Ben Mihoub, A; Frochot, C; Malaplate, C; Yen, FT, 2021)	0.62
"Low aqueous solubility and bioavailability is the limiting factor to achieve desired therapeutic efficacy for variety of new and existing drug moieties."	( Binary inclusion complexes of diflunisal with β-cyclodextrin and hydroxypropyl-β-cyclodextrin: Preparation and characterization. Ahmad, J; Asghar, S; Asif, M; Aslam, N; Bashir, M; Iqbal, MS; Irfan, M; Khan, IU; Khan, NR; Saleem, M; Shah, PA; Syed, HK, 2020)	0.56
"Improving solubility and administration route of isoflavone formononetin (FMN) are critical factors to improve its bioavailability in the oral cavity."	( Formononetin/methyl-β-cyclodextrin inclusion complex incorporated into electrospun polyvinyl-alcohol nanofibers: Enhanced water solubility and oral fast-dissolving property. Deng, Z; Fang, S; Liang, X; Lu, Y; Shi, Y; Wang, X; Wang, Y, 2021)	0.62
" However, RSV has met limited success due to its poor oral bioavailability and inefficient systemic delivery."	( Cyclodextrin based bone regenerative inclusion complex for resveratrol in postmenopausal osteoporosis. Baby, C; Chourasia, MK; Ghate, V; Lewis, S; Narayana Kalkura, S; Nayak, Y; Saklani, R; Shah, A; Shah, AA; Singh, PK, 2021)	0.62
" Cyclodextrin (CD) inclusion complexation is a method of choice for reducing side effects and improving bioavailability of drugs."	( Advancing insights on β-cyclodextrin inclusion complexes with SSRIs through lens of X-ray diffraction and DFT calculation. Aree, T, 2021)	0.62
"The results revealed that the ternary complex could be a promising drug delivery system to improve the oral bioavailability of the bacogenins."	( Ternary System of Bacogenins with Fulvic Acid and Hydrogenated Soy Lecithin: Preparation, Characterization and, Chandrasekhar, K; Gnananath, K; Jain, P; Kumar, KP; Mirza, MA; Nataraj, KS; Rao, BG, 2022)	0.72
" This study was intended to explore the potential use of the Dex@β-CD complex in drug delivery to enhance dexamethasone dissolution, thus improving its bioavailability and reducing its side effects."	( A Dispersion Corrected DFT Investigation of the Inclusion Complexation of Dexamethasone with β-Cyclodextrin and Molecular Docking Study of Its Potential Activity against COVID-19. Ali, FAM; Allal, H; Assaba, IM; Belhocine, Y; Ghoniem, MG; Rahali, S, 2021)	0.62
" However, the use of Alen has been limited due to its low bioavailability and gastrointestinal side effects."	( Alendronate-Decorated Nanoparticles as Bone-Targeted Alendronate Carriers for Potential Osteoporosis Treatment. Chen, S; Jing, C; Li, B; Liang, H; Liu, C; Na, H; Tan, H; Zhang, C; Zhao, L, 2021)	0.62
" The purpose of this study was to prepare LT-hydroxypropyl-beta-cyclodextrin inclusion complex (LT-HP-β-CD) to increase water solubility, oral bioavailability and antitumor effect of LT."	( Liquiritin-Hydroxypropyl-Beta-Cyclodextrin Inclusion Complex: Preparation, Characterization, Bioavailability and Antitumor Activity Evaluation. Adu-Frimpong, M; Bao, R; Cao, X; Chen, L; Ji, H; Shi, F; Toreniyazov, E; Wang, Q; Wei, C; Weng, W; Xu, X; Yu, J; Yu, Q; Zhang, K, 2022)	0.72
"1% w/v hydroxypropyl-β-cyclodextrin-based eye drop formulation and its bioavailability is limited by several drawbacks such as the nasolacrimal duct draining, the reflex blinking and the low volume of the conjunctival sac."	( Chitosan/sulfobutylether-β-cyclodextrin based nanoparticles coated with thiolated hyaluronic acid for indomethacin ophthalmic delivery. Arduino, I; Cutrignelli, A; Denora, N; Franco, M; Laquintana, V; Lopalco, A; Lopedota, A; Racaniello, GF; Ricci, F; Sigurdsson, HH, 2022)	0.72
"The purpose of this study was to evaluate the potential of a newly modified cyclodextrin derivative, water-soluble β-cyclodextrin-epichlorohydrin (β-CD), as an effective drug carrier to enhance the poor solubility and bioavailability of galangin (GAL), a poorly water-soluble model drug."	( Galangin/β-Cyclodextrin Inclusion Complex as a Drug-Delivery System for Improved Solubility and Biocompatibility in Breast Cancer Treatment. Abbas, ZS; Al-Subaiyel, A; Jabir, MS; Khan, RA; Mohammed, HA; Mohammed, SAA; Sulaiman, GM, 2022)	0.72
" However, the exceptionally low water solubility of these psoralens can cause incomplete and variable bioavailability limiting their applications and patient adherence to treatment."	( Improvement in Solubility-Permeability Interplay of Psoralens from da Conceição, EC; de Morais, MC; Lião, LM; Lima, EM; Machado, RD; Oliveira, GAR; Rezende, KR; Silva, JCG; Silva, LAD, 2022)	0.72
" Preparation of cyclodextrin inclusion complex to improve the solubility, stability, and bioavailability is a well-established technique."	( Cyclodextrin-Based Supramolecular Ternary Complexes: Emerging Role of Ternary Agents on Drug Solubility, Stability, and Bioavailability. Chaudhari, P; Lewis, SA; Suvarna, P, 2022)	0.72
" Supramolecular complexation of photosensitizers into cyclodextrins (CD) is promising to improve their poor solubility, compromising their bioavailability and upcoming applications in PDT."	( Improved Hypericin solubility via β-cyclodextrin complexation: Photochemical and theoretical study for PDT applications. Gusmão, LA; Machado, AEH; Perussi, JR, 2022)	0.72
"In order to overcome the insolution and low bioavailability of the vitexin in vivo, β-cyclodextrin-vitexin (β-CD-vitexin) microspheres were prepared, and their effects on the proliferation of SW480 cells were observed."	( Preparation of β-CD-Vitexin Microspheres and their Effects on SW480 Cell Proliferation. Deng, Y; Ding, C; Kang, M; Li, S; Ma, J; Tian, Z; Wang, D; Zhang, K; Zhang, Y, 2023)	0.91
" However, the bioavailability of IBG is not optimal due to its finite aqueous solubility, thus hampering its potential therapeutic exploitation."	( Enhancement of the oral bioavailability of isopropoxy benzene guanidine though complexation with hydroxypropyl-β-cyclodextrin. Lu, Y; Peng, X; Qin, Z; Xie, S; Yang, L; Zeng, D; Zeng, Z; Zhang, W; Zhao, F, 2022)	0.72
" However, due to its low solubility its bioavailability is limited."	( Comparative Interaction Studies of Quercetin with 2-Hydroxyl-propyl-β-cyclodextrin and 2,6-Methylated-β-cyclodextrin. Cournia, Z; Diamantis, DA; Georgiou, N; Javornik, U; Mauromoustakos, T; Papadourakis, M; Papakyriakopoulou, P; Plavec, J; Tzakos, AG; Tzeli, D; Vakali, V; Valsami, G; Zoupanou, N, 2022)	0.72
" This study aimed to investigate the effects of particle size reduction and dispersants on the dissolution and bioavailability of ginsenosides in ginseng."	( Effects of particle size reduction combined with β-cyclodextrin on the Li, K; Liu, C; Liu, J; Liu, TC; Yang, T; Zhao, Z; Zhou, P, 2022)	0.72
" Albendazole (ABZ) is the first-line treatment for CE; however therapeutic failure of ABZ against CE occurs because of size and location of formed cysts as well its low aqueous solubility and consequently its erratic bioavailability in plasma."	( In vitro efficacy of albendazole-loaded β-cyclodextrin against protoscoleces of Echinococcus granulosus sensu stricto. Ahmadpour, E; Akbarzadeh, A; Asadi, M; Asadi, N; Bakhtiar, NM; Casulli, A; de Lourdes Pereira, M; Ebrahimi, M; Mahami-Oskouei, M; Norouzi, R; Rodrigues Oliveira, SM; Spotin, A, 2022)	0.72
"Hydroxypropyl-β-cyclodextrin (HPβCD) is a derivative of cyclodextrin extensively used in the pharmaceutical industry, since it improves the solubility of drugs, and widens their oral bioavailability and safety profile."	( Theoretical study of structures and charge distributions of 2-, 3- and 6-hydroxypropyl-β-cyclodextrin with different degrees of substitution. Alvira, E, 2023)	0.91
"42 fold enhancement in the relative bioavailability of PXM-NS10 as compared to commercial tablets."	( Formulation and evaluation of Piroxicam nanosponge for improved internal solubility and analgesic activity. Abdoun, SA; Alail, JA; Aljumah, RS; Alkhalifah, SA; Aloqla, RM; Alzughaibi, DA; Gaber, DA; Radwan, MA, 2023)	0.91
" Cyclodextrins (CDs) and their derivatives can be used as drug carriers that can boost stability, solubility, and bioavailability of physiologically active substances."	( β-Cyclodextrin and folic acid host-guest interaction binding parameters determined by Taylor dispersion analysis and affinity capillary electrophoresis. Chen, DDY; Dai, Y; Li, H; Sun, C; Wang, S; Yang, Y, 2023)	0.91
" This study discusses the application of β-cyclodextrin (βCD) for the delivery of highly bioavailable and hydrophilic iron, ferric sodium EDTA, which exhibits great functionality in the presence of polyphenols and phytates with potential application in food fortification."	( Preparation and characterization of an iron-β-cyclodextrin inclusion complex: factors influencing the host-guest interaction. Diosady, LL; Saffarionpour, S, 2023)	0.91
" This antipsychotic drug has an inadequate therapeutic impact because of its minimal and idiosyncratic oral bioavailability to treat schizophrenia."	( Enhanced Solubility and Stability of Aripiprazole in Binary and Ternary Inclusion Complexes Using Hydroxy Propyl Beta Cyclodextrin (HPβCD) and L-Arginine. Afridi, M; Ahsan, H; Awais, S; El-Serehy, HA; Farooq, N; Ishtiaq, F; Muhammad, SA; Nadeem, T; Sultana, K; Ullah, A, 2023)	0.91
"Meloxicam (MLX) is one of the most effective NSAIDs, but its poor water solubility and low bioavailability limit its clinical application."	( Preparation and In Vitro and In Vivo Evaluation of Rectal In Situ Gel of Meloxicam Hydroxypropyl-β-cyclodextrin Inclusion Complex. Lei, X; Li, D; Liu, Q; Peng, Y; Wang, C; Wang, T; Wu, Y; Yang, T; Zhang, G, 2023)	0.91
"Cyclodextrins (CD) and derivatives are functional excipients that can improve the bioavailability of numerous drugs."	( Cyclodextrins and derivatives in drug delivery: New developments, relevant clinical trials, and advanced products. Bernkop-Schnürch, A; Haddadzadegan, S; Kali, G, 2024)	1.44

Excerpt	Relevance	Reference
" These results suggest that HP-beta-CyD is particularly useful in solving problems encountered on storage of amorphous nifedipine in solid dosage forms."	( Inhibitory effect of 2-hydroxypropyl-beta-cyclodextrin on crystal-growth of nifedipine during storage: superior dissolution and oral bioavailability compared with polyvinylpyrrolidone K-30. Hirayama, F; Horiuchi, Y; Ikegami, K; Uekama, K; Wang, Z, 1992)	0.28
" The method was employed successfully with samples from rats and mice treated with Aroclor, beta-naphthoflavone, or phenobarbital; from monkeys dosed with Aroclor; and from untreated dogs."	( Coupled beta-cyclodextrin and reverse-phase high-performance liquid chromatography for assessing biphenyl hydroxylase activity in hepatic 9000g supernatant. van Lier, RB; Weaver, DE, 1986)	0.27
" From a practical point of view, 2 seems to be particularly useful for improving the pharmaceutical properties of flurbiprofen in various dosage forms."	( Improvement of dissolution and suppository release characteristics of flurbiprofen by inclusion complexation with heptakis(2,6-di-O-methyl)-beta-cyclodextrin. Hirayama, F; Imai, T; Irie, T; Maeda, T; Otagiri, M; Uekama, K, 1985)	0.27
" The statistical evaluation of the results do not indicate differences in onset, duration and maximum of action between the two dosage forms."	( Preparation and central action of propofol/hydroxypropyl-beta-cyclodextrin complexes in rabbits. Reiter, S; Spiegl, P; Stumpf, C; Viernstein, H, 1993)	0.29
"In the past 20 years, cyclodextrin (CD) research has achieved considerable results, as indicated by the large number of publications and patents, the six international symposia on CDs, the new dosage forms of medicines prepared with CDs, etc."	( Conditions of cyclodextrin complexation. Giordano, F; Hadi, IA; Kata, M; Selmeczi, B, 1993)	0.29
" On the other hand, nasal administration of the lyophilized insulin/DM beta CD powder dosage form in rabbits resulted in increased serum insulin concentrations, and a maximum decrease in blood glucose of about 50%."	( Nasal insulin delivery with dimethyl-beta-cyclodextrin as an absorption enhancer in rabbits: powder more effective than liquid formulations. Merkus, FW; Romeijn, SG; Schipper, NG; Verhoef, JC, 1993)	0.29
"The thiazolobenzimidazole 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a] benzimidazole, TBI, is an experimental drug for the treatment of AIDS which exhibits a low water solubility (11 micrograms/mL) and is therefore difficult to administer in an injectable solution dosage form at a target solution concentration of 10 mg/mL."	( Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxypropyl-beta-cyclodextrin. Anderson, BD; Hoesterey, BL; Lim, K; Tinwalla, AY; Xiang, TX, 1993)	0.29
" Based on this approach, liquid dosage forms were configured for both parenteral and oral use."	( Intravenous and oral pharmacokinetic evaluation of a 2-hydroxypropyl-beta-cyclodextrin-based formulation of carbamazepine in the dog: comparison with commercially available tablets and suspensions. Anderson, WR; Bodor, N; Brewster, ME; Cheung, B; Derendorf, H; Estes, KS; Meinsma, D; Moreno, D; Pablo, L; Pop, E; Sawchuk, R; Webb, AI, 1997)	0.3
" This method is convenient and reproducible for analyses of these two components in different dosage forms."	( Simultaneous determination of amoxycillin and clavulanic acid in pharmaceutical products by HPLC with beta-cyclodextrin stationary phase. Tsou, TL; Wang, TM; Wu, JR; Young, CD, 1997)	0.3
" Gastroscopy was performed at base-line and after the dosing period of 14 days."	( [Comparative endoscopic study of gastroduodenal tolerance of piroxicam-beta-cyclodextrin vs piroxicam]. Müller, P; Simon, B, )	0.13
"Better absorption of spironolactone from the spironolactone: beta-cyclodextrin complex formulation should lead to a reduction in dosage and perhaps a more consistent effect in patients with chronic liver disease."	( Improved bioavailability and clinical response in patients with chronic liver disease following the administration of a spironolactone: beta-cyclodextrin complex. Abosehmah-Albidy, AZ; Chrystyn, H; Losowsky, MS; Wong, V; York, P, 1997)	0.3
") treatment was directly followed by repeated administrations of an oral solution of itraconazole at a dosage of either 200 mg once daily or 200 mg twice daily (b."	( Concentrations in plasma and safety of 7 days of intravenous itraconazole followed by 2 weeks of oral itraconazole solution in patients in intensive care units. Colardyn, F; De Beule, K; Decruyenaere, J; Groen, K; Jaqmin, P; Van Peer, A; Vandewoude, K; Vogelaers, D; Woestenborghs, R, 1997)	0.3
"The bioavailability of ITR and OH-ITR is enhanced when ITR oral solution is given in the fasted state; this was true for both single and multiple dosing to steady state."	( Food interaction and steady-state pharmacokinetics of itraconazole oral solution in healthy volunteers. Barone, JA; Bierman, RH; Colaizzi, JL; Guarnieri, J; Hassell, AE; Jessen, L; Moskovitz, BL, )	0.13
" The oral absorption of spironolactone was studied in rats to evaluate the need to adjust spironolactone dosage in prospective clinical studies."	( Water-soluble beta-cyclodextrins in paediatric oral solutions of spironolactone: preclinical evaluation of spironolactone bioavailability from solutions of beta-cyclodextrin derivatives in rats. Kaukonen, AM; Lennernäs, H; Mannermaa, JP, 1998)	0.3
" The current studies may be applied to deliver MT transdermally using aqueous-based vehicles and to fabricate MT dosage forms."	( Percutaneous absorption and model membrane variations of melatonin in aqueous-based propylene glycol and 2-hydroxypropyl-beta-cyclodextrin vehicles. Ayres, JW; Cui, JH; Lee, BJ; Parrott, KA; Sack, RL, 1998)	0.3
" An intramuscular dosage form of ziprasidone was developed using beta-cyclodextrin sulfobutyl ether (SBECD) to solubilize the drug by complexation."	( Inclusion complexation of ziprasidone mesylate with beta-cyclodextrin sulfobutyl ether. Blake, JF; Chrunyk, B; Duffy, EM; Kim, Y; Massefski, W; Oksanen, DA, 1998)	0.3
" Thus, the age-related dissolution problems of GB can be overcome by utilizing the GB/CD complex in the tablet dosage form."	( Effect of aging on the dissolution stability of glibenclamide/beta-cyclodextrin complex. Babu, RJ; Pandit, JK, 1999)	0.3
" Since the bioavailability of itraconazole is reduced in these patients, a satisfactory dosing regimen remains to be defined."	( Itraconazole trough concentrations in antifungal prophylaxis with six different dosing regimens using hydroxypropyl-beta-cyclodextrin oral solution or coated-pellet capsules. Glasmacher, A; Hahn, C; Marklein, G; Molitor, E; Sauerbruch, T; Schmidt-Wolf, IG, 1999)	0.3
" It is nearly insoluble in water and it influences not only the selection of the dosage form, but also its biological availability."	( [Effect of temperature on drug solubility in complex formation of flubendazole and 2-hydroxypropyl-beta-cyclodextrin]. Rabisková, M; Sucman, E; Vetchý, D, 2000)	0.31
"In the research of new dosage forms improving the therapeutic index of local anesthetics, we studied cyclodextrins, cyclic oligosaccharides forming soluble inclusion complexes with various lipophilic drugs."	( [Biopharmaceutics of local anesthetic-cyclodextrin complexes following loco-regional administration]. Chevanne, F; Dollo, G; Fréville, JC; Le Corre, P; Leverge, R, 2000)	0.31
"Carbomers are carboxyvinylic derivatives that are widely used in the manufacture of hydrogel dosage forms."	( Use of beta-cyclodextrins to prevent modifications of the properties of carbopol hydrogels due to carbopol-drug interactions. Blanco-Fuente, H; Blanco-Méndez, J; Esteban-Fernández, B; Otero-Espinar, FJ, 2002)	0.31
"The aim of this study was to compare nimesulide-beta-cyclodextrin and naproxen in terms of short-term (2 weeks) pain control with scheduled dosing and medium-term (5."	( A randomized, double-blind, multicenter trial of nimesulide-beta-cyclodextrin versus naproxen in patients with osteoarthritis. Bisogno, S; Di Martino, S; Fioravanti, A; Marcolongo, R; Oldani, V; Scotti, A; Storri, L, 2002)	0.31
" The primary outcome measures for scheduled dosing were pain on movement (measured by visual analog scale), morning stiffness score, Lequesne index, and adverse events."	( A randomized, double-blind, multicenter trial of nimesulide-beta-cyclodextrin versus naproxen in patients with osteoarthritis. Bisogno, S; Di Martino, S; Fioravanti, A; Marcolongo, R; Oldani, V; Scotti, A; Storri, L, 2002)	0.31
" On-demand dosing may be an effective and well-tolerated low-dose regimen of nonsteroidal anti-inflammatory drugs for the maintenance of pain control in OA in the medium term."	( A randomized, double-blind, multicenter trial of nimesulide-beta-cyclodextrin versus naproxen in patients with osteoarthritis. Bisogno, S; Di Martino, S; Fioravanti, A; Marcolongo, R; Oldani, V; Scotti, A; Storri, L, 2002)	0.31
"Nifedipine is a highly photosensitive drug that requires restricted protection from light during manufacturing, storage and handling of its dosage forms."	( Effect of inclusion complexation with cyclodextrins on photostability of nifedipine in solid state. Abanumay, KA; Al-Angary, AA; Bayomi, MA, 2002)	0.31
" In addition, in vivo repeated dosing of RM beta-CD did not show any toxicity up to 20% w/v."	( The effects of water-soluble cyclodextrins on the histological integrity of the rat nasal mucosa. Asai, K; Hosoda, S; Katsuta, H; Morishita, M; Nagai, T; Noro, M; Shinomiya, K; Takayama, K, 2002)	0.31
" In these studies, dosing vehicles are typically employed in high concentrations to dissolve the test compounds in dose formulations."	( Post-column infusion study of the 'dosing vehicle effect' in the liquid chromatography/tandem mass spectrometric analysis of discovery pharmacokinetic samples. Naidong, W; Shou, WZ, 2003)	0.32
" The objective of this study was to investigate the effect of the pulmonary route on the systemic absorption of FK224 in comparison with other administration routes, and to determine the bioavailability (BA) of FK224 following pulmonary administration in rats using various dosage forms."	( Improvement of pulmonary absorption of cyclopeptide FK224 in rats by co-formulating with beta-cyclodextrin. Ibuki, R; Kawashima, Y; Nakate, T; Ohike, A; Tokunaga, Y; Yoshida, H, 2003)	0.32
" It has been applied to the determination of (S)-(+)terbutaline and (R)-(-)-terbutaline in urine from healthy volunteer dosed with racemic terbutaline sulfate."	( Determination of terbutaline enantiomers in human urine by capillary electrophoresis using hydroxypropyl-beta-cyclodextrin as a chiral selector. Jeun, EY; Kang, JS; Kim, HJ; Kim, KH; Mar, W; Seo, SH; Youm, JR, 2003)	0.32
"These results suggest that the newly developed dosage form of piroxicam is effective and well tolerated in the treatment of patients with chronic BP."	( Efficacy and tolerability of piroxicam-beta-cyclodextrin in the outpatient management of chronic back pain. Buran, I; Gazdik, F; Gogolak, I; Mihal, A; Pijak, MR; Turcani, P; Turcaniova, Z, 2002)	0.31
" These studies suggested that an HPbetaCD-based, emulsified wax cream formulation was a useful and effective dosage form for treating vaginal candidiasis."	( A mucoadhesive, cyclodextrin-based vaginal cream formulation of itraconazole. Brewster, ME; De Proost, E; Delaet, U; Francois, M; Peeters, J; Putteman, P; Snoeckx, E; Wouters, F, 2003)	0.32
"Three kinds of topical dosage forms of minoxidil (MXD), namely vesicles, double emulsions, and an inclusion complex with hydoxypropyl-beta-cyclodextrin (HP-beta-CD), were prepared."	( Minoxidil-containing dosage forms: skin retention and after-rinsing hair-growth promotion. Kim, JC; Lee, MH; Rang, MJ, )	0.13
" The preparation of this inclusion compound has advantages in limited amount, long time effect, easily preserved and convenient administration as a new dosage form."	( [Application of beta-cyclodextrin inclusion technique in new dosage form of angelica sinensis essential oil]. Chen, YZ; Zhao, Y; Zhou, CX; Zou, JK, 2002)	0.31
" Dosage forms were prepared by encapsulating the complexes without the addition of excipients."	( The physicochemical characteristics and bioavailability of indomethacin from beta-cyclodextrin, hydroxyethyl-beta-cyclodextrin, and hydroxypropyl-beta-cyclodextrin complexes. Casella, R; Jambhekar, S; Maher, T, 2004)	0.32
" After single intravenous dosing (2."	( Biopharmaceutics of beta-cyclodextrin derivative-based formulations of acitretin in Sprague-Dawley rats. Chan, SY; Ho, PC; Lin, HS; Liu, X, 2004)	0.32
" Two hours after dosing they received another 240 ml of the beverage."	( Influence of grapefruit juice on the systemic availability of itraconazole oral solution in healthy adult volunteers. Fincher, TK; Franks, AM; Gubbins, PO; Gurley, BJ; McConnell, SA; Penzak, SR; Saccente, M; Williams, DK, 2004)	0.32
" The observed complexation may substantially modify properties of bupivacaine hydrochloride dosage forms with sufficient concentration of cyclodextrin but bupivacaine cations are readily released from the weak cyclodextrin complexes by dilution."	( Bupivacaine hydrochloride complexation with some alpha- and beta-cyclodextrins studied by potentiometry with membrane electrodes. Bieliková, Z; Demko, M; Kaclík, P; Kopecký, F; Vojteková, M, 2004)	0.32
" Although a high inter-subject variability was observed, the results pointed to the feasibility of using betaCD in order to modulate CBZ release and absorption, as well as to reduce the drug dosage maintaining the same plasma levels."	( Bioavailability of carbamazepine:beta-cyclodextrin complex in beagle dogs from hydroxypropylmethylcellulose matrix tablets. Bassani, VL; Bertuol, JB; Dalla Costa, T; Groch, KR; Koester, LS; Mayorga, P; Moellerke, R; Xavier, CR, 2004)	0.32
" 2-PP was extracted from silicone tubing during routine manufacture of a blank dosage form formulated with only HPbetaCD, resulting in detectable levels of 2-PP in the final product."	( 2-Hydroxypropyl-beta-cyclodextrin extracts 2-phenylphenol from silicone tubing. Beijnen, JH; den Brok, MW; Hillebrand, MJ; Nuijen, B; van der Schoot, SC, 2004)	0.32
" The dose-response using HbetaC-encapsulated-17beta-oestradiol revealed that at 17beta-oestradiol concentrations of 10(-4) and 10(-5) mol/l, blastocyst development was significantly reduced."	( Oestradiol, cyclodextrin-encapsulated 17beta-oestradiol and the oestradiol solubilizer 2-hydroxypropyl-beta-cyclodextrin all impair preimplantation mouse embryo development. Gardner, DK; Karagenc, L; Lane, M, 2004)	0.32
" We relate this effect to the high cholesterol content of DRMs because manipulating the cholesterol content of rod outer segment membranes by methyl-beta-cyclodextrin yielded a similar shift of the Ca2+-dependent dose-response curve of rhodopsin kinase inhibition."	( Recoverin and rhodopsin kinase activity in detergent-resistant membrane rafts from rod outer segments. Churumova, VA; Höppner-Heitmann, D; Koch, KW; Philippov, PP; Polkovnikova, OO; Senin, II; Tikhomirova, NK, 2004)	0.32
" Permethrin with beta-cyclodextrin(CD) made into Inclusion Compound (IC) can increase its stability and reduce dosage to remain on the tea."	( [Study on measuring host-guest ratio of inclusion compound of beta-CD-permethrin by IR]. Dong, M; Leng, LB; Shao, QF; Xie, XH; Zeng, LP, 2004)	0.32
" Survival times in the majority of rats dosed with aldicarb and receiving intravenous cyclodextrin were longer compared with the control rats only dosed with aldicarb per os."	( Evaluation of hydroxypropyl-beta-cyclodextrin in the treatment of aldicarb poisoning in rats. Botha, CJ; Verster, RS, 2004)	0.32
" This review concludes that HP-beta-CD is well tolerated in the animal species tested (rats, mice and dogs), particularly when dosed orally, and shows only limited toxicity."	( 2-Hydroxypropyl-beta-cyclodextrin (HP-beta-CD): a toxicology review. Gould, S; Scott, RC, 2005)	0.33
" Suddenly withdrawing progesterone after repeated dosing (PW) exacerbates ischemia and causes increased anxiety, seizure susceptibility, and excitotoxicity."	( Tapered progesterone withdrawal enhances behavioral and molecular recovery after traumatic brain injury. Cutler, SM; Hoffman, SW; Pettus, EH; Stein, DG, 2005)	0.33
"Hydroxyproyl-beta-cyclodextran (HPBCD), methyl cellulose (MC), Tween 80 and PEG400 are commonly used in dosing formulations in pharmacokinetic (PK) studies during the early drug discovery stage."	( A study of common discovery dosing formulation components and their potential for causing time-dependent matrix effects in high-performance liquid chromatography tandem mass spectrometry assays. Broske, L; Korfmacher, WA; Mei, H; Pena, A; Wang, G; Wang, S; Xu, X; Zhou, Q, 2005)	0.33
", lidocaine and ketoprofen) from mucoadhesive buccal film dosage forms."	( Effect of low-molecular-weight beta-cyclodextrin polymer on release of drugs from mucoadhesive buccal film dosage forms. Arakawa, Y; Hashida, M; Kawakami, S; Yamashita, F, 2005)	0.33
" Selected binary systems were used for preparation of direct compression tablets with reduced drug dosage (50 mg)."	( Development of fast-dissolving tablets of flurbiprofen-cyclodextrin complexes. Cirri, M; Corti, G; Maestrelli, F; Mura, P; Rangoni, C, 2005)	0.33
"HCl per dosage unit for use in phase I clinical trials."	( Pharmaceutical development of a parenteral lyophilised formulation of the investigational anticancer agent ES-285.HCl. Beijnen, JH; Den Brok, MW; Manada, C; Meijer, DM; Millán, E; Nuijen, B, )	0.13
" Solid dosage forms (hydroxypropylmethyl cellulose /HPMC/ capsules and tablets) were prepared from the selected products on the basis of their dissolution profile and the in vitro membrane diffusion results."	( [Preparation and investigation of gemfibrozil + dimethyl-beta-cyclodextrin products and solid dosage forms]. Aigner, Z; Eros, I; Hassan, BH; Hódi, K; Kása, P, 2005)	0.33
" The compound is pharmaceutically formulated as a lyophilised product containing 25 or 50 mg ES-285 x HCl and 500 or 1000 mg 2-hydroxypropyl-beta-cyclodextrin per dosage unit and requires reconstitution with sterile water for injection before intravenous administration."	( Compatibility and stability of the novel anticancer agent ES-285 x HCl formulated with 2-hydroxypropyl-beta-cyclodextrin in infusion devices. Beijnen, JH; Calvo, P; Den Brok, MW; García, JL; Manada, C; Miranda, E; Nuijen, B, 2006)	0.33
" The objective of this study was to investigate the storage stability of the lipid devices, as long-term storage stability ensuring acceptable shelf-life can be considered the most important parameter for commercially viable sustained-release dosage forms."	( Continuous release of Rh-interferon (alpha-2a from triglyceride implants: storage stability of the dosage forms. Mohl, S; Winter, G, 2006)	0.33
"The purpose of this study was to develop and evaluate a solid nonaqueous oral dosage form for a new hepatitis C drug, PG301029, which is insoluble and unstable in water."	( Improving cyclodextrin complexation of a new antihepatitis drug with glacial acetic acid. He, Y; Jain, A; Johnson, JL; Yalkowsky, SH, 2006)	0.33
" Taken together, our data provide the basis for potential therapeutic application of MCD in combination with other conventional cytotoxic drugs to facilitate reduction of drug dosage that offers a better chemotherapeutic approach with low toxicity."	( Methyl-beta-cyclodextrin enhances the susceptibility of human breast cancer cells to carboplatin and 5-fluorouracil: involvement of Akt, NF-kappaB and Bcl-2. Ajay, AK; Bhat, MK; Chhipa, RR; Singh, S; Upadhyay, AK; Vijayakumar, MV, 2006)	0.33
" With the increase of dosage of complex, its absorption did not show saturated phenomenon in gastro-intestinal tract in rats and the constant Ka did not show significant difference, suggesting that the transport of mechanism in vivo is similar to passive transport."	( [Studies on absorptive mechanism of lipophilic components of danshen from its hydroxypropyl-beta-cyclodextrin inclusion complex]. Jiang, X; Wang, L; Yang, J; Zhou, J, 2006)	0.33
"There is a need for nasal drug delivery of metoclopramide HCI (MTC) in specific patient populations where the use of commercially available intravenous and oral dosage forms may be inconvenient and/or unfeasible."	( Nasal absorption of metoclopramide from different Carbopol 981 based formulations: In vitro, ex vivo and in vivo evaluation. Altunay, H; Ozkan, CK; Ozkan, Y; Savaser, A; Tas, C; Tasdemir, U, 2006)	0.33
" In CD-treated thylakoid membranes incubated with DCBQ the electron transport through PSII, estimated as oxygen evolution (OE), is largely enhanced according to a S-shaped (sigmoidal) dose-response curve displaying a sharp inflection point, or transition."	( Investigation of the electron transfer site of p-benzoquinone in isolated photosystem II particles and thylakoid membranes using alpha- and beta-cyclodextrins. Dudekula, S; Fragata, M, 2006)	0.33
" The potential salt form would ideally decrease the rate of (SBE)7M-beta-CD release from osmotic pump formulations and result in an increase in the rate and extent of drug release in osmotic pump tablet and pellet dosage forms."	( Evaluation of various properties of alternative salt forms of sulfobutylether-beta-cyclodextrin, (SBE)7M-beta-CD. Haslam, JL; Sotthivirat, S; Stella, VJ, 2007)	0.34
" Liquid formulations (PG:PEG400:H2O) provided higher oral bioavailability than solid formulations dissolved and dosed as aqueous oral solutions."	( Pharmacokinetics of tamoxifen after intravenous and oral dosing of tamoxifen-hydroxybutenyl-beta-cyclodextrin formulations. Buchanan, CM; Buchanan, NL; Edgar, KJ; Little, JL; Malcolm, MO; Ruble, KM; Wacher, VJ; Wempe, MF, 2007)	0.34
" In vivo studies in rats compared pharmacokinetic (PK) profiles of different formulations dosed intranasally."	( In vitro formulation optimization of intranasal galantamine leading to enhanced bioavailability and reduced emetic response in vivo. Brandt, GC; Costantino, HR; Foerder, CA; Leonard, AK; Quay, SC; Sileno, AP, 2007)	0.34
" The sensors were used successfully for the determination of I and II in laboratory prepared mixtures with their degradation products, in pharmaceutical dosage forms and in plasma."	( Stability-indicating electrochemical methods for the determination of meclophenoxate hydrochloride and pyritinol dihydrochloride using ion-selective membrane electrodes. El-Bardicy, MG; El-Sayed, MA; El-Tarras, MF; Lotfy, HM, 2007)	0.34
" Dosage forms and the solid-state properties of drugs and excipients in a formulation may be influenced by the processing conditions used."	( Characterization of prednisolone in controlled porosity osmotic pump pellets using solid-state NMR spectroscopy. Haslam, JL; Lubach, JW; Munson, EJ; Sotthivirat, S; Stella, VJ, 2007)	0.34
" We found that 13-cis-RA was eliminated from the body through a dose-independent process after intravenous injection of either sodium salt or the HP-beta-CD formulation within the tested dosage range (2."	( Biopharmaceutics of 13-cis-retinoic acid (isotretinoin) formulated with modified beta-cyclodextrins. Chan, SY; Ho, PC; Lee, P; Leong, WW; Lin, HS; Yang, JA, 2007)	0.34
" In vitro and in vivo performances of these formulations were investigated over a VP immediate release dosage form."	( Cyclodextrin multicomponent complexation and controlled release delivery strategies to optimize the oral bioavailability of vinpocetine. Falcão, AC; Ferreira, DC; Patrício, JA; Ribeiro, LS; Veiga, FJ, 2007)	0.34
" No food effects were observed with the itraconazole:HBenBCD solid dosage forms."	( Pharmacokinetics of itraconazole after intravenous and oral dosing of itraconazole-cyclodextrin formulations. Buchanan, CM; Buchanan, NL; Edgar, KJ; Klein, S; Little, JL; Ramsey, MG; Ruble, KM; Wacher, VJ; Wempe, MF, 2007)	0.34
"HCl), an oral anti-hyperglycaemic agent highly soluble in water, with triacetyl-beta-cyclodextrin (TAbetaCyD), a hydrophobic CyD derivative practically insoluble in water, were prepared to evaluate their suitability for the development of a sustained-release dosage form of the drug."	( Physical-chemical characterization of binary systems of metformin hydrochloride with triacetyl-beta-cyclodextrin. Capasso, G; Cirri, M; Corti, G; Maestrelli, F; Mura, P, 2007)	0.34
" With the increase of dosage of complex, TS IIA's absorption did not show saturated phenomenon, suggesting its transport mechanism in vivo might primary be passive transport."	( In situ intestinal absorption behaviors of tanshinone IIA from its inclusion complex with hydroxypropyl-beta-cyclodextrin. Hua, JX; Ling, W; Rui, LC, 2007)	0.34
"For CD-based formulations, it is important to directly monitor the complexation status of the drug present in final dosage form pharmaceuticals."	( Detecting and identifying the complexation of nimodipine with hydroxypropyl-beta-cyclodextrin present in tablets by Raman spectroscopy. Ke, W; Liu, F; Yang, X; Yu, L; Zi, P, 2008)	0.35
" The potential histological changes were also evaluated after direct dosing of suspensions of naproxen alone and powdered mixtures of inclusion complex-loaded tablet into rat intestinal segments."	( Colonic release and reduced intestinal tissue damage of coated tablets containing naproxen inclusion complex. Lee, BJ; Lee, MK; Piao, ZZ, 2008)	0.35
"3%) when dosed with saquinavir base-HBenBCD capsules."	( Pharmacokinetics of saquinavir after intravenous and oral dosing of saquinavir: hydroxybutenyl-beta-cyclodextrin formulations. Buchanan, CM; Buchanan, NL; Edgar, KJ; Little, JL; Ramsey, MG; Ruble, KM; Wacher, VJ; Wempe, MF, 2008)	0.35
" The cytotoxicity profiles of these materials were evaluated by protein, MTT, and LDH assays, which demonstrate that all the click clusters remain nontoxic within the expected dosage range while the positive controls, Jet PEI and Superfect, were highly cytotoxic."	( Polycationic beta-cyclodextrin "click clusters": monodisperse and versatile scaffolds for nucleic acid delivery. Fichter, KM; Reineke, TM; Srinivasachari, S, 2008)	0.35
" The method was applied to nine commercial CP preparations in six dosage forms and CP enantiomers were well separated without any disturbance of other ingredients or impurities present."	( Enantioselective determination of chlorpheniramine in various formulations by HPLC using carboxymethyl-beta-cyclodextrin as a chiral additive. Chen, QC; Hwang, GS; Jeong, SJ; Kang, JS; Kim, KH, 2008)	0.35
"1%, indicating that no interference is observed from concomitants usually present in dosage forms."	( A spectrofluorimetric sequential injection method for the determination of penicillamine using fluorescamine in the presence of beta-cyclodextrins. Al-Kindy, SM; Al-Lawati, ZH; Suliman, FE, 2008)	0.35
" In particular, the microwave technology has been considered in order to prepare an enhanced release dosage form for the poorly soluble drug Ibuprofen (IBU), employing PVP/VA 60/40 (PVP/VA 64) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) as hydrophilic carriers."	( Microwave generated solid dispersions containing Ibuprofen. Baxa, P; Bellich, B; Moneghini, M; Princivalle, F, 2008)	0.35
"The mean increase of CoQ10 plasma concentrations after dosing with Q10Vital forms was determined to be over the reference formulation and the area under the curve values, extrapolated to infinity (AUC(inf)), were also higher with the tested forms; statistically significant 120 and 79% increases over the reference were calculated for the Q10Vital liquid and powder, respectively."	( Relative bioavailability of two forms of a novel water-soluble coenzyme Q10. Fir, M; Pravst, I; Prosek, M; Smidovnik, A; Walczak, J; Zmitek, J; Zmitek, K, 2008)	0.35
" Three new dosage forms containing beta-cyclodextrin and surfactants (SDS, ASC8) were compared in the FST with the commercial extract."	( Pharmacological in vivo test to evaluate the bioavailability of some St John's Wort innovative oral preparations. Bergonzi, MC; Bilia, AR; Galeotti, N; Ghelardini, C; Isacchi, B; Vincieri, FF, 2009)	0.35
"Pharmacokinetic studies in mice traditionally require one animal per time point, resulting in dosing and euthanizing a large number of animals and producing suboptimal quality of pharmacokinetic data due to inter-animal variability and dosing error."	( Improved pharmacokinetic and bioavailability support of drug discovery using serial blood sampling in mice. Hageman, W; Huebert, ND; Peng, SX; Rockafellow, BA; Skedzielewski, TM, 2009)	0.35
" Permeation studies were carried out with Franz diffusion cells containing sublingual mucosa membranes with PBS receptor phase and dosed with solutions of quinine hydrochloride or quinine/2-hydroxypropyl-beta-cyclodextrin complexes."	( Permeation of quinine across sublingual mucosa, in vitro. Heard, CM; Ong, CM, 2009)	0.35
"To prepare a novel floating micropellets containing hydroxy propyl-beta-oyclodextrin(puerarin-HP-beta-CD) for gastroretentive dosage form and evaluate its pharmaceutical characteristics in vitro."	( [Preparation and in vitro evaluation of gastroretentive dosage form containing puerarin-HP-beta-CD inclusion complex]. Cui, JH; Miao, WJ; Qian, Y; Xia, Q, 2008)	0.35
"The solubility and release rate of puerarin are increased by the formation of inclusion complex with HP-beta-CD and its gastroretentive dosage forms displayed satisfied floating and sustained release characteristics."	( [Preparation and in vitro evaluation of gastroretentive dosage form containing puerarin-HP-beta-CD inclusion complex]. Cui, JH; Miao, WJ; Qian, Y; Xia, Q, 2008)	0.35
" The pharmacological effect of PLGA/HPbetaCD/insulin LPP was confirmed by dose-response studies performed on both normoglycaemic and streptozotocin-induced diabetic rats."	( Insulin-loaded PLGA/cyclodextrin large porous particles with improved aerosolization properties: in vivo deposition and hypoglycaemic activity after delivery to rat lungs. d'Emmanuele di Villa Bianca, R; Giovino, C; La Rotonda, MI; Miro, A; Quaglia, F; Sorrentino, R; Ungaro, F, 2009)	0.35
" There were no significant differences in efficacy between Growtropin II (daily dose of 5 microg/animal for 14 days) and DA-3003 (weekly dose of 35 microg/animal for 14 days with a dosing interval of a week) in hypophysectomized rats, as assessed by changes in body weight and the width of the tibial growth plate."	( Development of a sustained-release recombinant human growth hormone formulation. Choi, MK; Kang, SH; Kim, BM; Kim, TH; Kim, YJ; Kwak, HH; Lee, GI; Shim, CK; Shim, WS; Son, MK; Yang, HC, 2009)	0.35
"To compare the dose-response relationships of two formulations [Tween- or hydroxypropyl-b-cyclodextrin (HP-b-CD)-based] of intradermal capsaicin in healthy volunteers and to assess the effect of potential covariates of response."	( A comparison of two formulations of intradermal capsaicin as models of neuropathic pain in healthy volunteers. Akesson, J; Gustafsson, H; Lau, CL; Miller, L; Rolan, P; Williams, D; Yap, S, 2009)	0.35
" Given the greater ease of formulation and the superior dose-response relationship, the HP-beta-CD formulation is preferable for use in the model in future studies."	( A comparison of two formulations of intradermal capsaicin as models of neuropathic pain in healthy volunteers. Akesson, J; Gustafsson, H; Lau, CL; Miller, L; Rolan, P; Williams, D; Yap, S, 2009)	0.35
" The dose-response curve of glucose-stimulated insulin secretion was shifted to the right in LDLR(-/-) islets."	( Primary hypercholesterolaemia impairs glucose homeostasis and insulin secretion in low-density lipoprotein receptor knockout mice independently of high-fat diet and obesity. Bonfleur, ML; Boschero, AC; Carneiro, EM; Collares-Buzato, CB; de França Carvalho, CP; de Gabriel Dorighello, G; de Oliveira, HC; Ribeiro, RA; Vanzela, EC, 2010)	0.36
" The solubility/dose ratios values of PZQ-cyclodextrin complexes calculated considering the low (150 mg) and the high dose (600 mg) of PZQ, used in practice, indicate that PZQ complexation with CDs may result in drug dosage forms that would behave as a BCS-Class I depending on the administered dose."	( Effect of cyclodextrin complexation on the aqueous solubility and solubility/dose ratio of praziquantel. Archontaki, H; Macheras, P; Maragos, S; Valsami, G, 2009)	0.35
" ATN Ca unit dosage form was developed and evaluated for physico-chemical properties, stability, and dissolution rate."	( Solubility and stability enhancement of atorvastatin by cyclodextrin complexation. Palem, CR; Patel, S; Pokharkar, VB, )	0.13
"8) after BS/beta-CD dosing and the longer mean residence time in this organ, regardless of the administration route, reveals that the complex may be a potential drug carrier for the central nervous system delivery of BS."	( Pre-clinical pharmacokinetics evaluation of an anticonvulsant candidate benzaldehyde semicarbazone free and included in beta-cyclodextrin. Azeredo, FJ; Beraldo, Hde O; Dalla Costa, T; Kaiser, M; Uchôa, Fde T, 2010)	0.36
" Consistent with the enhanced solubility, the plasma exposure (both AUC and Cmax) of flurbiprofen when dosed as the mixed system was significantly higher (as much as 2 to 3-fold) than that without surfactant or beta-CD, with surfactant alone, or with beta-CD alone."	( Enhanced oral bioavailability of flurbiprofen by combined use of micelle solution and inclusion compound. Balakrishnan, P; Choi, HG; Han, MJ; Joe, JH; Kim, JO; Li, DX; Oh, DH; Park, SM; Seo, Y; Yan, YD; Yong, CS, 2010)	0.36
" The study also evaluates the intrinsic effect of the dosage form on the improvement of paclitaxel oral bioavailability."	( Enhanced oral paclitaxel bioavailability after administration of paclitaxel-loaded nanosponges. Ansari, KA; Cavalli, R; Torne, SJ; Trotta, F; Vavia, PR, 2010)	0.36
"5 h and 1 h after administration of BCD-meloxicam orally than those of unmodified meloxicam (both dosed at 10 mg/kg)."	( Influence on analgesic activity and serum levels after meloxicam complexation with beta-cyclodextrin in mice and rats. Dolezal, T; Janovský, M; Krsiak, M; Procháizková, M; Slíva, J, 2010)	0.36
" These results suggested the feasibility that thermosensitive gels could be used as an effective dosage form to enhance the nasal absorption of FXD HCl."	( Poloxamer/cyclodextrin/chitosan-based thermoreversible gel for intranasal delivery of fexofenadine hydrochloride. Balakrishnan, P; Cho, HJ; Chung, SJ; Hong, SS; Jang, TY; Kim, DD; Kim, KS; Park, EK; Shim, CK; Song, KW, 2011)	0.37
"Dissolution testing is an important test for judging the effectiveness of a pharmaceutical dosage form."	( Solid dispersion of prednisolone: solid state characterization and improvement of dissolution profile. Khanam, J; Palanisamy, M, 2011)	0.37
"The objective of the present research was to evaluate the physicochemical characteristics of berberine chloride and to assess the complexation of drug with 2-hydroxypropyl-β-cyclodextrin (HPβCD), a first step towards solution dosage form development."	( Physicochemical characterization of berberine chloride: a perspective in the development of a solution dosage form for oral delivery. Avery, MA; Battu, SK; Chittiboyina, AG; Maddineni, S; Majumdar, S; Repka, MA, 2010)	0.36
"The main objective of this study was to investigate thermosensitive Pluronic F-127 (PF-127) hydrogel for the modified release of a potent alcohol and opioid antagonist, naltrexone (NTX) hydrochloride, in a subcutaneous injectable dosage form."	( Thermosensitive Pluronic hydrogel: prolonged injectable formulation for drug abuse. Derakhshandeh, K; Fashi, M; Seifoleslami, S, 2010)	0.36
" In these teratology studies, pregnant females were dosed during the period of organogenesis, followed by an assessment of fetal external, visceral, and skeletal development."	( Assessment of hydroxypropyl methylcellulose, propylene glycol, polysorbate 80, and hydroxypropyl-β-cyclodextrin for use in developmental and reproductive toxicology studies. Enright, BP; Kopytek, SJ; McIntyre, BS; Thackaberry, EA; Treinen, KA, 2010)	0.36
"Mixtures containing ibuprofen (IB) complexed with β-cyclodextrin (βCD) obtained by two complexation methods [suspension/solution (with water removed by air stream, spray- and freeze-drying) and kneading technique] were processed into pharmaceutical dosage forms (minitablets and capsules)."	( Comparison of ibuprofen release from minitablets and capsules containing ibuprofen: β-cyclodextrin complex. Cabral-Marques, HM; Costa, PC; Pinto, JF; Salústio, PJ, 2011)	0.37
" The combined use of RAMEB, CS, and NaDHC could be exploited to develop effective oral dosage forms of oxaprozin, with increased drug solubility and permeability, and then improved bioavailability."	( Improvement of oxaprozin solubility and permeability by the combined use of cyclodextrin, chitosan, and bile components. Cirri, M; Maestrelli, F; Mennini, N; Mura, P; Zerrouk, N, 2011)	0.37
" To evaluate its suitability as a drug candidate, a pharmacokinetic study was carried out in Sprague-Dawley rats with the emphasis to identify the impact of aqueous solubility, dose escalation, food, and repeated dosing on its oral bioavailability."	( Preclinical pharmacokinetic evaluation of resveratrol trimethyl ether in sprague-dawley rats: the impacts of aqueous solubility, dose escalation, food and repeated dosing on oral bioavailability. Ho, PC; Lin, HS, 2011)	0.37
" In this short communication, we report our investigations towards developing two alternative novel, simple, flexible and effective drug delivery systems that provide optimal dosage of drugs precisely where and when needed and therefore achieve and sustain a complex delivery profile."	( Development of novel drug delivery prototypes devices for targeted delivery drug therapy at the molecular level in aqueous media. George, R; Oberhozer, TG; Perchyonok, VT, 2011)	0.37
" Replacement of fructose by mannitol in the current clinical BPA formulation is, therefore, feasible with advantages of increased dosing and removal of issues related to fructose intolerance and calorific load."	( Physicochemical investigation of the influence of saccharide-based parenteral formulation excipients on L-p-boronphenylalanine solubilisation for boron neutron capture therapy. Dooley, N; Elliott, M; Ford, SJ; Halbert, GW; Schmidt, E, 2012)	0.38
" PM103 is an intravenous formulation of clopidogrel being developed as an alternative to oral clopidogrel to provide for dosing flexibility in the emergent clinical setting."	( Pharmacokinetics and platelet aggregation inhibitory effects of a novel intravenous formulation of clopidogrel in humans. Adams, MP; Cooper, WD; Cushing, DJ; Kowey, PR; Machatha, S; Mosher, GL; Souney, PF; Zhang, B, 2012)	0.38
" Passive dosing was applied to control chemical activities of HOCs in aqueous solutions by equilibrium partitioning from a poly(dimethylsiloxane) polymer preloaded with the chemicals."	( Measuring binding and speciation of hydrophobic organic chemicals at controlled freely dissolved concentrations and without phase separation. de Jonge, LW; Gouliarmou, V; Mayer, P; Smith, KE, 2012)	0.38
" The pharmacokinetics of midazolam in different dosage forms was investigated in rabbits (dose 1mg/rabbit) after intravenous administration of midazolam solution and after sublingual administration of midazolam solution, midazolam/HP-β-CD/sucrose solution or midazolam/HP-β-CD/sucrose powder."	( The effect of hydroxypropyl-beta-cyclodextrin and sucrose on the sublingual absorption of midazolam in rabbits. Jarho, P; Järvinen, K; Kaartama, R; Kokki, H; Lehtonen, M; Ranta, VP; Savolainen, J; Toljamo, K; Turunen, E, 2012)	0.38
"Over the last decades the poor solubility of new drugs has become an important issue, with one of the main challenges being to develop oral dosage forms with acceptable bioavailability for such compounds."	( Application of a ternary HP-β-CD-complex approach to improve the dissolution performance of a poorly soluble weak acid under biorelevant conditions. Dressman, JB; Klein, S; Zoeller, T, 2012)	0.38
" With the bioconversion rate as the index, the effects of pH value, temperature, reaction time, dosage of enzyme and concentration of naringin-HP-beta-CD on conversion rate of naringenin were detected for the purpose of optimizing the preparation condition."	( [Preparation of naringenin by enzymolysis of naringin-HP-beta-CD]. Cui, L; Jia, X; Jiang, Y; Qian, Q; Sun, E; Zhang, Z, 2012)	0.38
" The main objective is to improve solubility of simvastatin beta-CD complex (1:2) by co-precipitation method and then to deliver the same in sustained release dosage form."	( Preparation and statistical optimization of alginate based stomach specific floating microcapsules of simvastatin. Barik, BB; Premchandani, TA, )	0.13
"Despite of advancements in dosage form design and use of multifunctional excipients, improvement in dissolution characteristics of molecules like Telmisartan (TEL) having exceedingly pH dependent and poor solubility profile is still challenging."	( Amorphous ternary cyclodextrin nanocomposites of telmisartan for oral drug delivery: improved solubility and reduced pharmacokinetic variability. Sangwai, M; Vavia, P, 2013)	0.39
" Even the low dose of nanomedicines offered the comparable results to those of control groups at the high dosage in most cases."	( Assembled nanomedicines as efficient and safe therapeutics for articular inflammation. Che, L; He, H; Jia, Y; Li, S; Li, X; Liu, Y; Zhang, J; Zhou, J; Zhou, X; Zhu, Y, 2012)	0.38
" Experimental studies were performed in detail to check the effect of the synthesis process of the microspheres, the stabilizer dosage, monomer concentration, and initiator dosage on the particle size and distribution, the microstructures were characterized with SEM, TEM, infrared (IR) and the particle size distribution investigation."	( Preparation and characterization of polystyrene microspheres in the presence of beta-cyclodextrin. Deng, Y; Fu, J; Lu, Z; Wang, W; Xu, L; Zhang, L, 2012)	0.38
"Acyclovir possesses low solubility in water and in lipid bilayers, so that its dosage forms do not allow suitable drug levels at target sites following oral, local, or parenteral administration."	( Design, synthesis, and in vitro evaluation of new amphiphilic cyclodextrin-based nanoparticles for the incorporation and controlled release of acyclovir. Chevalier, Y; Duffour, M; Parrot-Lopez, H; Perret, F, 2013)	0.39
" This was done to evaluate potential degradation and thereby biological conversion of the cyclodextrins if dosed orally, as the intestinal tract contains α-amylase for digestive purposes."	( In vitro investigations of α-amylase mediated hydrolysis of cyclodextrins in the presence of ibuprofen, flurbiprofen, or benzo[a]pyrene. Holm, R; Jørgensen, EB; Larsen, KL; Lumholdt, LR, 2012)	0.38
" Here, an economic complexation technology combined with direct tablet compression method has been developed to meet the requirements of a patient friendly dosage known as taste-masked dispersible tablets loaded PTB (TPDPTs): (1) TPDPTs should have optimal disintegration and good physical resistance (hardness); (2) a low-cost, simple but practical preparation method suitable for industrial production is preferred from a cost perspective."	( Design and evaluation of an economic taste-masked dispersible tablet of pyridostigmine bromide, a highly soluble drug with an extremely bitter taste. Tan, Q; Teng, Y; Zhang, J; Zhang, L, 2012)	0.38
" The mechanism for zero-order release of these compression-coated tablets was solvent penetration into the dosage form and drug dissolution from the erosion of the gelled HPC matrix."	( Compression-coated tablets of glipizide using hydroxypropylcellulose for zero-order release: in vitro and in vivo evaluation. Chen, H; Chen, Q; Huang, H; Qi, X; Rui, Y; Wu, Z; Xing, J; Zhang, H, 2013)	0.39
" This study aimed to investigate the impacts of aqueous solubility, fasting, dose escalation, and dosing route on its bioavailability in Sprague-Dawley rats."	( Pharmacokinetics of pterostilbene in Sprague-Dawley rats: the impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability. Ho, PC; Lin, HS; Yeo, SC, 2013)	0.39
" However, when dosed in a solution formulated with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) (15 mg/kg), PTS possessed good bioavailability (F = 59."	( Pharmacokinetics of pterostilbene in Sprague-Dawley rats: the impacts of aqueous solubility, fasting, dose escalation, and dosing route on bioavailability. Ho, PC; Lin, HS; Yeo, SC, 2013)	0.39
" The amorphous complexes obtained in this study may be useful in the preparation of pharmaceutical dosage forms of SMT."	( Binding of sulfamethazine to β-cyclodextrin and methyl-β-cyclodextrin. Aiassa, V; Delrivo, A; Longhi, MR; Zoppi, A, 2013)	0.39
" Marketed formulations for parenteral administration usually contain 75 mg/3 mL of diclofenac sodium, which provide limited dosing flexibility, and are usually given intramuscularly."	( Efficacy and safety of low dose subcutaneous diclofenac in the management of acute pain: a randomized double-blind trial. Dietrich, T; Gugliotta, B; Leeson, R; Petersen, B, 2014)	0.4
" The aim of this work was to study an agglomerated powder dosage form for oral administration of artemisinin based on the artemisinin/β-cyclodextrin primary microparticles."	( Agglomerated oral dosage forms of artemisinin/β-cyclodextrin spray-dried primary microparticles showing increased dissolution rate and bioavailability. Balducci, AG; Bettini, R; Colombo, G; Colombo, P; Khan, NA; Magosso, E; Rossi, A; Sonvico, F; Yuen, KH, 2013)	0.39
" In conclusion, preparation of dutasteride-loaded HP-β-CD nanostructures using the supercritical antisolvent process affords a viable alternative solid dosage form for dutasteride."	( Influence of hydrophilic additives on the supersaturation and bioavailability of dutasteride-loaded hydroxypropyl-β-cyclodextrin nanostructures. Kim, MS, 2013)	0.39
" Therefore, it is important to develop an alternative dosage form which is easier to administer and avoids first-pass metabolism."	( Enhanced transdermal drug delivery of zaltoprofen using a novel formulation. Baek, JS; Cho, CW; Jung, SH; Kang, JS; Lim, JH; Shin, SC, 2013)	0.39
" The effect of different experimental parameters, such as initial pH, adsorbent dosage and initial metal ion concentration, were investigated."	( A novel biodegradable β-cyclodextrin-based hydrogel for the removal of heavy metal ions. Huang, Z; Liu, S; Liu, T; Wu, Q; Zhang, B, 2013)	0.39
" Available experimental evidences and published patents are indicative of broadening the circle of the applications in point of both technological advantages and dosage forms."	( [Pharmaceutical applications of sulfobuthylether-beta-cyclodextrin]. Sebestyén, Z; Szabó, B; Szepesi, K, 2013)	0.39
"The challenge of designing a delayed-release oral dosage form is significantly increased when the drug substance is poorly water soluble."	( Design of tablets for the delayed and complete release of poorly water-soluble weak base drugs using SBE7M-β-CD as a solubilizing agent. Rao, VM; Stella, VJ; Zannou, EA, 2011)	0.37
" More importantly, the drug efficiency was greatly improved with CA dosage as less as one-third of the pure drug due to the synergistic effect of the drug and carrier."	( Novel GO-COO-β-CD/CA inclusion: its blood compatibility, antibacterial property and drug delivery. Fan, Y; Gu, H; Shen, J; Wang, W; Xiao, Y; Zhou, N, 2014)	0.4
" The studies indicated that the inclusion complex with the cyclodextrin derivative improved remarkably the physicochemical properties of albendazole, being a suitable excipient to design oral dosage forms."	( Modified β-cyclodextrin inclusion complex to improve the physicochemical properties of albendazole. complete in vitro evaluation and characterization. García, A; Lamas, MC; Leonardi, D; Salazar, MO, 2014)	0.4
" Healthy animals of both species were allocated into four experimental groups of 44 animals each: FLBZ-CD oral and FLBZ-CDsc, treated with the FLBZ-CD formulation by the oral or subcutaneous routes, respectively; FLBZ-TWEENsc, dosed subcutaneously with the FLBZ-TWEEN formulation; and FLBZ-CMC oral, treated orally with the FLBZ suspension."	( Exploring the potential of flubendazole in filariasis control: evaluation of the systemic exposure for different pharmaceutical preparations. Alvarez, L; Ceballos, L; Geary, T; Lanusse, C; Mackenzie, C, 2014)	0.4
"Doxycycline hyclate (DOX) is a highly photosensitive drug, a feature that limits the stability of the corresponding dosage forms."	( Increasing doxycycline hyclate photostability by complexation with β-cyclodextrin. Kogawa, AC; Longhi, MR; Nunes Salgado, HR; Quevedo, MA; Zoppi, A, 2014)	0.4
" Furthermore, formulating UAMC01398 into the film dosage form did not influence its antiviral activity."	( Development and characterization of a solid dispersion film for the vaginal application of the anti-HIV microbicide UAMC01398. Appeltans, B; Ariën, KK; Augustijns, P; Augustyns, K; Brouwers, J; Crucitti, T; Grammen, C; Michiels, J; Van den Mooter, G, 2014)	0.4
" The Cmax values of SG after dosing with the S nanosuspension were 12."	( Nanosuspension development of scutellarein as an active and rapid orally absorbed precursor of its BCS class IV glycoside scutellarin. Ai, N; Cao, F; Chang, Q; Lee, SMY; Li, S; Miao, X; Yang, X; Zheng, Y, 2014)	0.4
" But the dosing schedules are essential to achieve a balance between vascular collapse and intratumoral uptake of chemotherapeutic agents."	( Antimetastasis and antitumor efficacy promoted by sequential release of vascular disrupting and chemotherapeutic agents from electrospun fibers. Chen, M; Li, X; Luo, X; Wei, J; Zhang, H; Zhang, Y, 2014)	0.4
"Cyclodextrins (CDs) in combination with therapeutic proteins and other bioactive compounds have been proposed as candidates that show enhanced chemical and enzymatic stability, better absorption, slower plasma clearance and improved dose-response curves or immunogenicity."	( A novel synthetic luteinizing hormone-releasing hormone (LHRH) analogue coupled with modified β-cyclodextrin: insight into its intramolecular interactions. Grdadolnik, SG; Kellici, T; Kordopati, GG; Mavromoustakos, T; Merzel, F; Tselios, TV; Tsivgoulis, GM, 2015)	0.42
" These findings suggested that developed thermoreversible gels could be used as promising dosage forms to improve intranasal drug absorption."	( Carbopol-incorporated thermoreversible gel for intranasal drug delivery. Balakrishnan, P; Cho, HJ; Hahn, TW; Ko, HJ; Park, EK; Song, CK; Song, KW, 2015)	0.42
" Dissolution studies on β -cyclodextrin-Irbesartan complex revealed that β -CDs formed were useful in preparing immediate release oral dosage forms."	( Production of β -cyclodextrin from pH and thermo stable Cyclodextrin Glycosyl Transferase, obtained from Arthrobacter mysorens and its evaluation as a drug carrier for Irbesartan. Bhaskar, VK; Narayanan, K; Rajesh, Y; Rao, JV; Reddy, MS; Shenoy, GG; Subrahmanyam, VM, 2015)	0.42
" Diluent in direct compression formulation has a dual role: it increases bulk of the dosage form and it promotes binding of the constituent particles of the formulation."	( [Application of β-cyclodextrin in the formulation of ODT tablets containing ibuprofen]. Kasperek, R; Poleszak, E; Zimmer, Ł, )	0.13
" Thus, the strategy of host-guest inclusion was very effective and could be successfully used in the development of suitable pharmaceutical dosage form with enhanced therapeutic activity."	( Inclusion complexes of bendamustine with β-CD, HP-β-CD and Epi-β-CD: in-vitro and in-vivo evaluation. Gidwani, B; Vyas, A, 2015)	0.42
" Vehicles were dosed orally once daily to HanWistar rats for a minimum of 28 days and a wide range of toxicological parameters were assessed."	( Safety data on 19 vehicles for use in 1 month oral rodent pre-clinical studies: administration of hydroxypropyl-ß-cyclodextrin causes renal toxicity. Burdett, L; Cotton, P; Finney, R; Garner, C; Hargreaves, A; Harris, J; Healing, G; Kirk, S; Pivette, P; Schramm, C; Sulemann, T, 2016)	0.43
" Fluorescence images of skin samples after 24h of permeation were in line with ZnPc dosage in the skin and demonstrated the ability of NPs covalently tagged with rhodamine to penetrate the skin and to locate in the intercellular spaces."	( Skin transport of PEGylated poly(ε-caprolactone) nanoparticles assisted by (2-hydroxypropyl)-β-cyclodextrin. Conte, C; Costabile, G; d'Angelo, I; Grassia, G; Ialenti, A; Miro, A; Musto, P; Pannico, M; Quaglia, F; Tirino, P; Ungaro, F, 2015)	0.42
" However, establishment of the optimum dosage of HPBCD remains to be determined."	( Efficacy of 2-Hydroxypropyl-β-cyclodextrin in Niemann-Pick Disease Type C Model Mice and Its Pharmacokinetic Analysis in a Patient with the Disease. Arima, H; Higaki, K; Higashi, T; Irie, T; Ishitsuka, Y; Kondo, Y; Matsuo, M; Mochinaga, S; Motoyama, K; Nakagata, N; Ohno, K; Shiraishi, K; Takeo, T; Tanaka, Y; Uchio, Y; Wada, K; Yamada, Y, 2015)	0.42
"The use of solid oral dosage forms is typically favored with regard to stability and ease of administration."	( In-vitro and in-vivo evaluation of taste-masked cetirizine hydrochloride formulated in oral lyophilisates. Axe, P; Breitkreutz, J; Grother, L; Preis, M, 2015)	0.42
" Combined dosing caused no greater deficit, suggesting a common mode of action."	( Hearing Loss and Otopathology Following Systemic and Intracerebroventricular Delivery of 2-Hydroxypropyl-Beta-Cyclodextrin. Cronin, S; Duncan, RK; Hoenerhoff, M; Lin, A; Thompson, K, 2015)	0.42
" Further dosing as well as dose escalations are needed to more completely ascertain the safety and efficacy of intrathecal HP-β-CD."	( Intrathecal 2-hydroxypropyl-beta-cyclodextrin in a single patient with Niemann-Pick C1. Chen, AH; Dickson, PI; Farhat, NY; Jiang, X; Maarup, TJ; Ory, DS; Porter, FD; Sidhu, R, )	0.13
" Moreover, the use of these effervescent tablets in an orodispersible dosage form can improve oral drug bioavailability and act as an attractive pediatric dosage form."	( Novel levocetirizine HCl tablets with enhanced palatability: synergistic effect of combining taste modifiers and effervescence technique. Labib, GS, 2015)	0.42
"The dosing of drugs in an aqueous cyclodextrin formulation requires sufficient amount of cyclodextrins to fully solubilize the drug, as described by Stella's cyclodextrin utility number (UCD)."	( Displacement of Drugs From Cyclodextrin Complexes by Bile Salts: A Suggestion of an Intestinal Drug-Solubilizing Capacity From an In Vitro Model. Holm, R; Olesen, NE; Westh, P, 2016)	0.43
" Daily dosing over 28 days in rats resulted in mild to moderate, unilateral or bilateral erosion/ulceration of the olfactory epithelium, frequently with minimal to mild, acute to sub-acute inflammation of the lamina propria at the dorsal turbinates of the nasal cavity in 2/10 males and 3/10 females in the high-dose group (0."	( A novel nasal powder formulation of glucagon: toxicology studies in animal models. Carballo, D; McInally, K; Normand, P; Piché, C; Reno, FE; Silo, S; Stotland, P; Triest, M, 2015)	0.42
" To evaluate the suitability of the novel excipient focused to develop oral dosage forms, albendazole, a BSC class II compound, was chosen as a model drug."	( Promising applications in drug delivery systems of a novel β-cyclodextrin derivative obtained by green synthesis. García, A; Lamas, MC; Leonardi, D, 2016)	0.43
" However, there exists an intricate interplay between opposing effects that determine the optimal dosing criterion."	( Effect of cyclodextrin concentration on the oral bioavailability of danazol and cinnarizine in rats. Hartvig, RA; Holm, R; Jørgensen, EB; Larsen, DB; Olesen, NE; Westh, P, 2016)	0.43
"8:1, MA:β-CD = 6:1, reaction temperature of 80 °C, reaction time of 6 h, and dropping time of 40 min when MA was dosed as a substrate, and SSS and KPS were dosed as dropping reactants simultaneously."	( Research on the synthesis and scale inhibition performance of a new terpolymer scale inhibitor. Bao, Y; Li, M; Zhang, Y, 2016)	0.43
"Inconsistent dosage of insulin (INS) for type 2 diabetes patients lead to severe adverse effects like limb amputation, blindness and fatal hypo or hyper glycaemia."	( Enzyme coated beta-cyclodextrin for effective adsorption and glucose-responsive closed-loop insulin delivery. Anirudhan, TS; Nair, AS; Nair, SS, 2016)	0.43
"The findings suggested that FB is the best alternative for large-scale production of solid dosage forms containing CARV."	( Development of carvedilol-cyclodextrin inclusion complexes using fluid-bed granulation: a novel solid-state complexation alternative with technological advantages. Alonso, EC; Cunha-Filho, MS; Durig, T; Galter, D; Lima, EM; Marreto, RN; Martins, FT; Riccomini, K; Silva, LA; Taveira, SF, 2016)	0.43
" Previous studies have evaluated its efficacy using both oral and transdermal dosage forms."	( Water-soluble Complex of Curcumin with Cyclodextrins: Enhanced Physical Properties For Ocular Drug Delivery. Abd-Elgawad, AH; El-Dahan, MS; Jablonski, MM; Maria, DN; Mishra, SR; Soliman, OA; Wang, L, 2017)	0.46
" The usefulness of the method was demonstrated in the control of stereoisomeric impurities in raw material as well as in the determination of the chiral stability of the drug in the solid state and in dosage forms used in safety assessment."	( Chiral separation of a basic drug with two chiral centers by electrokinetic chromatography for its pharmaceutical development. Crego, AL; Marina, ML; Martínez-Girón, AB, 2016)	0.43
" The results acquired for determination of phenobarbitone in its dosage forms utilizing the proposed sensors are in good agreement with those obtained by the British Pharmacopoeial method."	( Ionophore-based potentiometric PVC membrane sensors for determination of phenobarbitone in pharmaceutical formulations. Abounassif, M; Al-Majed, A; Alrabiah, H; Mostafa, GA, 2016)	0.43
" Therefore, these findings could provide a suitable pharmaceutical dosage to enhanced therapeutic activity."	( Evaluation of molecular chaperone drug function: Regorafenib and β-cyclodextrins. Hu, X; Li, Y; Sun, M; Tang, G, 2017)	0.46
" However, a fatty meal enhances its absorption hence the therapy indicates that the dosage form be consumed with a meal."	( Enhancement of oral bioavailability of anti-HIV drug rilpivirine HCl through nanosponge formulation Momin, M; Sangshetti, JN; Zaheer, Z; Zainuddin, R, 2017)	0.46
"The approach offers a comfortable dosing zone for AIDs patients, negating the requirement of consuming the formulation in a fed state due to enhancement in drugs' oral bioavailability."	( Enhancement of oral bioavailability of anti-HIV drug rilpivirine HCl through nanosponge formulation Momin, M; Sangshetti, JN; Zaheer, Z; Zainuddin, R, 2017)	0.46
" The results showed that the oxidation level of oxidized β-cyclodextrin was successfully controlled by adjusting the dosage of hydrogen peroxide."	( Synthesis of oxidized β-cyclodextrin with high aqueous solubility and broad-spectrum antimicrobial activity. Li, D; Li, X; Mu, C; Ren, H; Tan, H; Ye, Y; Zhu, S, 2017)	0.46
" The in silico model established in this study was validated by in vivo studies of 4 formulations containing different dosage of cyclodextrin, proving that it was accurate and reliable."	( The Solubility-Permeability Trade-Off of Progesterone With Cyclodextrins Under Physiological Conditions: Experimental Observations and Computer Simulations. Sun, J; Sun, L; Zhang, B, 2018)	0.48
" These results suggest that electospun films from EtOH system may be a good candidate for fast-dissolving drug delivery systems to increase palatability of dosage forms."	( Cyclodextrin-based oral dissolving films formulation of taste-masked meloxicam. Akkaramongkolporn, P; Kaomongkolgit, R; Opanasopit, P; Samprasit, W, 2018)	0.48
"Cooperation between researchers in the areas of medical, pharmaceutical and materials science has facilitated the development of pharmaceutical dosage forms that elicit therapeutic effects and protective action with a single product."	( Electrospun poly(ε-caprolactone) matrices containing silver sulfadiazine complexed with β-cyclodextrin as a new pharmaceutical dosage form to wound healing: preliminary physicochemical and biological evaluation. Carvalho, SG; Cotrim, MAP; de Paula Careta, F; Dutra, JAP; Oréfice, RL; Resende, JA; Souza, SOL; Villanova, JCO, 2018)	0.48
"Current scenario in asthmatic prevalence worldwide calls for a facile, cost-effective, and energy efficient methodology to formulate the potent bronchodilator, theophylline (THP), into an effective dosage forms."	( Spectroscopic and computational insights into theophylline/β-cyclodextrin complexation: inclusion accomplished by diverse methods. Das, S; Maharana, J; Mohanty, S; Subuddhi, U, )	0.13
"The aims of this study were to evaluate electrospinning as a continuous alternative to freeze drying in the production of a reconstitution injection dosage form, and to prove that aqueous electrospinning can be realized with a high production rate at room temperature."	( Continuous alternative to freeze drying: Manufacturing of cyclodextrin-based reconstitution powder from aqueous solution using scaled-up electrospinning. Andersen, SK; Csontos, I; Démuth, B; Farkas, A; Hirsch, E; Marosi, G; Nagy, B; Nagy, ZK; Szabó, E; Vass, P; Verreck, G; Vigh, T, 2019)	0.51
" Consequently, successful preparation of the ICs of BLFX with CDs provided possibility for devising new dosage form of BLFX, which held great promise for further applications in clinical fields."	( Preparation, Characterization, and Properties of Inclusion Complexes of Balofloxacin with Cyclodextrins. Li, H; Liu, Y; Pu, H; Qian, H; Ren, X; Tang, P; Tang, Y; Zhang, M; Zhao, L, 2019)	0.51
" A discussion of these obstacles as well as pharmacokinetics, monitoring, and dosing is provided."	( Brexanolone for Postpartum Depression: Clinical Evidence and Practical Considerations. Leader, LD; O'Connell, M; VandenBerg, A, 2019)	0.51
" Preliminary PD characterization of repeated iv dosing of 2-IB in an acute peripheral hypoxic ischemia model in healthy subjects did not reveal any notable effects of 2-IB, noting that this model was not selected to guide efficacy in the currently pursued indication of cerebral hypoxia-ischemia."	( First-in-Human Study of the Safety, Tolerability, Pharmacokinetics and - Preliminary Dynamics of Neuroprotectant 2-Iminobiotin in Healthy Subjects. de Leede, LGJ; Hartstra, J; Leufkens, PWTJ; Peeters-Scholte, CMPCD; van Hoogdalem, EJ; van Lier, JJ, 2020)	0.56
" It has several advantages for pediatric patients, as the dosage form disintegrates quickly in the mouth and does not require water for administration, thereby improving patient compliance with the treatment."	( Development of Pediatric Orodispersible Tablets Based on Efavirenz as a New Therapeutic Alternative. Ângelos, MA; da Silva, RMF; de Freitas Neto, JL; de Melo, CG; do Nascimento Gomes Barbosa, I; Dos Santos Mendes, LM; Ferreira, MRA; Neto, PJR; Rolim, LA; Soares, LAL, 2020)	0.56
"Despite being the most effective hypolipidemic agent, poor physicochemical properties of Rosuvastatin calcium (RCa) remain challenging obstacles in the development of pharmaceutical dosage forms."	( Preparation and Al-Heibshy, FNS; Başaran, E; Demirel, M; Öztürk, N, 2020)	0.56
"Aim of the study was to reduce the dose and dosing frequency of duloxetine HCl (DXT) by complexation with sulfobutylether-β-cyclodextrin (SBEβCD), an anionic cyclodextrin through permeation enhancement for more effective management of depression."	( Transdermal delivery of duloxetine-sulfobutylether-β-cyclodextrin complex for effective management of depression. Dahiya, L; Kumar, R; Sarwal, A; Sinha, VR, 2021)	0.62
" Experience with the medication and further research is needed to clarify whether the current recommended dosing regimen is required for efficacy."	( Evaluating brexanolone for the treatment of postpartum depression. Payne, JL, 2021)	0.62
" It also provides an overview of different studies, and outcomes thereof, regarding formulation development for IgGs and Ig-based molecules in liquid and solid (lyophilized) dosage forms with HP-β-CD."	( HP-β-CD for the formulation of IgG and Ig-based biotherapeutics. Garidel, P; Michaela, B; Wu, HH, 2021)	0.62
" The supramolecular adduct of RSP with RM-β-CD represents a valuable candidate for further research in developing new formulations with enhanced bioavailability and stability, and the results of this study allow a pertinent selection of three excipients that can be incorporated in solid dosage forms."	( Risperidone/Randomly Methylated β-Cyclodextrin Inclusion Complex-Compatibility Study with Pharmaceutical Excipients. Barvinschi, P; Cîrcioban, D; Ledeți, A; Ledeți, I; Miclău, M; Sbârcea, L; Suciu, O; Tănase, IM; Văruţ, RM; Vlase, G, 2021)	0.62
" An inappropriate dosage of this therapeutic drug causes side effects; therefore, it is necessary to develop a rapid and sensitive method to monitor the content of NTBC in patients' blood."	( β-Cyclodextrin Derivative Grafted on Silica Gel Represents a New Polymeric Sorbent for Extracting Nitisinone from Model Physiological Fluids. Barchańska, H; Danek, M; Korytkowska-Wałach, A, 2021)	0.62
" Two typical sulfonamides antibiotics (sulfamethoxazole, sulfadiazine) adsorption capacity were evaluated in terms of the dosage of composite materials, the ratio of each component, and the pH of the solution."	( Preparation of β-cyclodextrin/dopamine hydrochloride-graphene oxide and its adsorption properties for sulfonamide antibiotics. Deng, C; Ding, H; Liu, X; Xu, X; Yu, H; Yu, Z; Zhao, B; Zheng, K, 2022)	0.72
"Due to the growing demand for patient-friendly subcutaneous dosage forms, the ability to increasing protein solubility and stability in formulations to deliver on the required high protein concentrations is crucial."	( Hydroxylpropyl-β-cyclodextrin as Potential Excipient to Prevent Stress-Induced Aggregation in Liquid Protein Formulations. Brandenbusch, C; Häusler, O; Krieg, F; Peng, T; Stolzke, T; Zhang, H, 2022)	0.72
" The same level of autophagy induction was achieved at one-twentieth the dosage for the MITO-Porter (Me-PRX) compared to the naked Me-PRX."	( Differences in the Intracellular Localization of Methylated β-Cyclodextrins-Threaded Polyrotaxanes Lead to Different Cellular States. Daikuhara, S; Harashima, H; Nishida, K; Tamura, A; Yamada, Y; Yui, N, 2023)	0.91
"The development and analysis of pharmaceutical formulations often involves the determination of multiple active ingredients in a dosage form."	( Development and Method Validation of Design of Experiments-Optimized Tablet Formulation for Simultaneous Detection of Exemestane and Everolimus. Kumar, A; Kurmi, BD; Singh, D, )	0.13
" These results confirm the application of methyl-β-cyclodextrin as an effective excipient for incorporation in novel dosage forms to increase the solubility of poorly soluble drugs."	( Formulation and characterization of amiodarone-methyl-beta-cyclodextrin inclusion complexes: A molecular modelling perspective. Rhoden, CRB; Rolim, CMB; Rubenick, JB; Rubim, AM; Vendrame, LO; Zanella, I, 2024)	1.44

Product Category	Products
Baby & Kids Products	1
Vitamins & Supplements	1
Food & Beverages	1

Product	Brand	Category	Compounds Matched from Ingredients	Date Retrieved
Earth Mama Organic Milkmaid Tea -- 16 Tea Bags	Earth Mama	Baby & Kids Products	orange, caraway	2024-11-29 10:47:42
Jigsaw Health CoQ10 with SRT -- 60 Capsules	Jigsaw Health	Vitamins & Supplements	ß-cyclodextrin, Cellulose, Coenzyme Q10	2024-11-29 10:47:42
Wasa Crispbread Gluten Free Original -- 5.4 oz	Wasa	Food & Beverages	caraway, sugar	2024-11-29 10:47:42

Class	Description
cyclodextrin	A macrocycle composed of five or more D-glucopyranose units bonded via (1->4)-linkages.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
phosphopantetheinyl transferase	Bacillus subtilis	Potency	56.2341	0.1413	37.9142	100.0000	AID1490
AR protein	Homo sapiens (human)	Potency	24.4108	0.0002	21.2231	8,912.5098	AID1259243
aldehyde dehydrogenase 1 family, member A1	Homo sapiens (human)	Potency	39.8107	0.0112	12.4002	100.0000	AID1030
thyroid stimulating hormone receptor	Homo sapiens (human)	Potency	0.0158	0.0013	18.0743	39.8107	AID926; AID938
estrogen receptor 2 (ER beta)	Homo sapiens (human)	Potency	61.3171	0.0006	57.9133	22,387.1992	AID1259378
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	33.0544	0.0002	14.3764	60.0339	AID720691; AID720692
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	50.1489	0.0030	41.6115	22,387.1992	AID1159552; AID1159555
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	43.7907	0.0008	17.5051	59.3239	AID1159527; AID1159531
estrogen-related nuclear receptor alpha	Homo sapiens (human)	Potency	54.6489	0.0015	30.6073	15,848.9004	AID1224849
farnesoid X nuclear receptor	Homo sapiens (human)	Potency	27.5420	0.3758	27.4851	61.6524	AID588526; AID743217
activating transcription factor 6	Homo sapiens (human)	Potency	24.6253	0.1434	27.6121	59.8106	AID1159516
potassium voltage-gated channel subfamily H member 2 isoform d	Homo sapiens (human)	Potency	35.4813	0.0178	9.6374	44.6684	AID588834
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, D-MALTODEXTRIN BINDING PROTEIN	Escherichia coli	Kd	1.8000	1.8000	1.8000	1.8000	AID977611
Chain A, Limit Dextrinase	Hordeum vulgare	Kd	0.7000	0.7000	0.7000	0.7000	AID977611
Chain A, Solute-binding protein	Thermoactinomyces vulgaris	Kd	1.2000	0.7300	0.9650	1.2000	AID977611
Chain A, Solute-binding protein	Thermoactinomyces vulgaris	Kd	1.2000	0.7300	0.9650	1.2000	AID977611
Chain B, SusD	Bacteroides thetaiotaomicron VPI-5482	Kd	146.0000	89.0000	117.5000	146.0000	AID977611
Chain A, SusD	Bacteroides thetaiotaomicron VPI-5482	Kd	146.0000	89.0000	117.5000	146.0000	AID977611
Chain A, SusD	Bacteroides thetaiotaomicron VPI-5482	Kd	146.0000	89.0000	117.5000	146.0000	AID977611
Chain A, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
Chain B, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
Chain C, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
Chain D, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
Chain E, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
Chain F, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
Chain G, Alpha-hemolysin	Staphylococcus aureus	Kd	0.4800	0.4800	0.4800	0.4800	AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1347407	qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection	2020	ACS chemical biology, 07-17, Volume: 15, Issue:7	High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347100	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425	Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)	2019	The Journal of biological chemistry, 11-15, Volume: 294, Issue:46	Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347424	RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)	2019	The Journal of biological chemistry, 11-15, Volume: 294, Issue:46	Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347107	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID1347102	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347104	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347082	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347089	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347083	qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen	2020	Antiviral research, 01, Volume: 173	A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347103	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347090	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095	qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells	2018	Oncotarget, Jan-12, Volume: 9, Issue:4	Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID224247	In vitro reversal activity versus ~90% block by rocuronium in isolated mouse hemidiaphragm, expressed as % of maximum reversal at 360 uM conc.	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.
AID430067	Cytotoxicity against human HeLa cells up to 1000 uM after 48 hrs by MTT assay	2009	Bioorganic & medicinal chemistry, Aug-15, Volume: 17, Issue:16	A highly sensitive probe detecting low pH area of HeLa cells based on rhodamine B modified beta-cyclodextrins.
AID57704	Tested for in vitro activity against DU 145 cells at PTX dilution factor 1:500, expressed as percentage of cellular survival as a function of drug dilution	2002	Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12	Preparation, characterization, molecular modeling and in vitro activity of paclitaxel-cyclodextrin complexes.
AID57702	Tested for in vitro activity against DU 145 cells at PTX dilution factor 1:1000, expressed as percentage of cellular survival as a function of drug dilution	2002	Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12	Preparation, characterization, molecular modeling and in vitro activity of paclitaxel-cyclodextrin complexes.
AID222567	In vivo reversal activity versus ~90% block by rocuronium in guinea pig, expressed as % of maximum reversal at 316 umol/kg conc.	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.
AID294861	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 10 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID1412407	Antibacterial activity against Staphylococcus aureus FDA 209P assessed as decrease in cell viability after 30 mins by colony counting method	2018	MedChemComm, Mar-01, Volume: 9, Issue:3	Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized
AID382998	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 200 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID1321690	Aqueous diffusion coefficient of compound in 98:2 ratio of D2O/H2O solvent system at 25 degC by 1H NMR DOSY spectroscopy
AID14917	The Area under the concentration time curve of compound was measured on rats	1997	Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17	6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
AID1321689	Diffusion coefficient of the compound D2O at 11 mM and 25 degC by 1H NMR spectroscopy
AID294865	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 200 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID57701	Tested for in vitro activity against DU 145 cells at PTX dilution factor 1:100, expressed as percentage of cellular survival as a function of drug dilution	2002	Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12	Preparation, characterization, molecular modeling and in vitro activity of paclitaxel-cyclodextrin complexes.
AID294864	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 100 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID322958	Inhibition of synthetic amyloid beta-42 fibrillation by light scattering analysis relative to control	2007	The Journal of biological chemistry, Apr-06, Volume: 282, Issue:14	Small molecule inhibitors of aggregation indicate that amyloid beta oligomerization and fibrillization pathways are independent and distinct.
AID1337347	Aqueous solubility of the compound at room temperature measured per 100 ml of solution	2016	European journal of medicinal chemistry, Nov-29, Volume: 124	Synthesis and biological evaluation of novel pentacyclic triterpene α-cyclodextrin conjugates as HCV entry inhibitors.
AID14649	The maximum plasma concentration was measured on rats	1997	Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17	6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
AID18530	Pseudo-first-order rate constant was determined by hydrolysis p-NPP in the presence of Zn 2+ at 37 C	1999	Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18	Combinatorial search of substituted beta-cyclodextrins for phosphatase-like activity.
AID293631	Artificial HSP60-like chaperone activity assessed as prevention of citrate synthase thermal aggregation	2007	Bioorganic & medicinal chemistry, Mar-01, Volume: 15, Issue:5	HSP90-like artificial chaperone activity based on indole beta-cyclodextrin.
AID382992	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 2 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID382995	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 20 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID294859	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 2 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID18656	Oral bioavailability in rat	1997	Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17	6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
AID19858	The mean residence time was measured on rats	1997	Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17	6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
AID20774	Time required to reach maximum plasma concentration was measured on rats	1997	Journal of medicinal chemistry, Aug-15, Volume: 40, Issue:17	6A-O-[(4-biphenylyl)acetyl]-alpha-, -beta-, and -gamma-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-alpha-, -beta-, and -gamma-cyclodextrins: potential prodrugs for colon-specific delivery.
AID294860	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 5 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID57703	Tested for in vitro activity against DU 145 cells at PTX dilution factor 1:50, expressed as percentage of cellular survival as a function of drug dilution	2002	Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12	Preparation, characterization, molecular modeling and in vitro activity of paclitaxel-cyclodextrin complexes.
AID222261	In vivo reversal activity versus ~90% block by rocuronium in guinea pig	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.
AID320264	Induction of Escherichia coli pUC19 DNA cleavage assessed as non-cleaved DNA level at 0.714 mM after 12 hrs	2008	Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3	DNA cleavage by novel copper (II) complex and the role of beta-cyclodextrin in promoting cleavage.
AID382993	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 5 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID294862	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 20 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID224112	In vitro reversal activity versus ~90% block by rocuronium in isolated mouse hemidiaphragm, expressed as effective conc.	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: synthesis and structure-activity relationships.
AID382994	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 10 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID294863	Effect on copper-induced human LDL peroxidation assessed as inhibition of malonaldehyde production at 50 uM after 4 hrs	2007	European journal of medicinal chemistry, Jul, Volume: 42, Issue:7	Synthesis and antioxidant activity of new homocarnosine beta-cyclodextrin conjugates.
AID1351281	Solubility of the compound in water assessed per 100 ml	2018	European journal of medicinal chemistry, Jan-20, Volume: 144	Polymeric bile acid sequestrants: Review of design, in vitro binding activities, and hypocholesterolemic effects.
AID382997	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 100 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID382996	Antioxidant activity against copper-induced lipid peroxidation in human LDL assessed as inhibition of malondialdehyde formation at 50 uM relative to control	2008	European journal of medicinal chemistry, Feb, Volume: 43, Issue:2	New glycosidic derivatives of histidine-containing dipeptides with antioxidant properties and resistant to carnosinase activity.
AID322957	Inhibition of synthetic amyloid beta-42 fibrillation by ThT fluorescence analysis relative to control	2007	The Journal of biological chemistry, Apr-06, Volume: 282, Issue:14	Small molecule inhibitors of aggregation indicate that amyloid beta oligomerization and fibrillization pathways are independent and distinct.
AID1412405	Induction of membrane disruption in methicillin-sensitive Staphylococcus aureus FDA 209P assessed as increase in K+ efflux after 30 mins	2018	MedChemComm, Mar-01, Volume: 9, Issue:3	Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized
AID504749	qHTS profiling for inhibitors of Plasmodium falciparum proliferation	2011	Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043	Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2010	Journal of molecular biology, Nov-12, Volume: 403, Issue:5	Crystal structure of an essential enzyme in seed starch degradation: barley limit dextrinase in complex with cyclodextrins.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2008	Structure (London, England : 1993), Jul, Volume: 16, Issue:7	Starch catabolism by a prominent human gut symbiont is directed by the recognition of amylose helices.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2010	Proceedings of the National Academy of Sciences of the United States of America, May-04, Volume: 107, Issue:18	Molecular bases of cyclodextrin adapter interactions with engineered protein nanopores.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	1993	Biochemistry, Oct-12, Volume: 32, Issue:40	Refined 1.8-A structure reveals the mode of binding of beta-cyclodextrin to the maltodextrin binding protein.
AID1811	Experimentally measured binding affinity data derived from PDB	1993	Biochemistry, Oct-12, Volume: 32, Issue:40	Refined 1.8-A structure reveals the mode of binding of beta-cyclodextrin to the maltodextrin binding protein.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2009	The FEBS journal, Jun, Volume: 276, Issue:11	Crystal structures of open and closed forms of cyclo/maltodextrin-binding protein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	154 (1.79)	18.7374
1990's	693 (8.07)	18.2507
2000's	2879 (33.53)	29.6817
2010's	3937 (45.85)	24.3611
2020's	923 (10.75)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	97 (1.10%)	5.53%
Reviews	86 (0.98%)	6.00%
Case Studies	13 (0.15%)	4.05%
Observational	1 (0.01%)	0.25%
Other	8,588 (97.76%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (12)

Trial Overview

Trial	Phase	Enrollment	Study Type	Start Date	Status
A Study in Healthy Female Participants to Investigate the Effect of JNJ-64530440 on the Single-dose of Ethinylestradiol and Drospirenone (Oral Contraceptive), and Midazolam, and the Effect of a High-fat Meal on the Single-dose of JNJ-64530440 [NCT03890341]	Phase 1	0 participants (Actual)	Interventional	2021-06-01	Withdrawn(stopped due to Stopped due to a strategic decision.)
Phase 3, Double-blind, Randomized, Placebo-controlled, Parallel-group, Multicenter Study to Evaluate the Safety, Tolerability and Efficacy of 2000mg/kg of Trappsol®Cyclo™ (Hydroxypropyl-B-cyclodextrin) and Standard of Care Compared to Placebo and Standard [NCT04860960]	Phase 3	93 participants (Anticipated)	Interventional	2021-07-20	Recruiting
Phase 1/2a Study of 2-Hydroxypropyl-Beta-Cyclodextrin Therapy for Infantile Liver Disease Associated With Niemann-Pick Disease, Type C [NCT03471143]	Phase 1/Phase 2	12 participants (Anticipated)	Interventional	2019-02-22	Recruiting
A Phase I/II Study to Evaluate the Safety and PK of iv Trappsol Cyclo (HP-β-CD) in Patients With Niemann-Pick Disease Type C NPC-1 and the Pharmacodynamic Effects of Treatment Upon Markers of Cholesterol Metabolism and Clinical Outcomes [NCT02912793]	Phase 1/Phase 2	12 participants (Actual)	Interventional	2017-03-20	Completed
A Single-Center, Randomized, Open-Label, 2-Period Complete Crossover Study to Compare the Bioavailability of a Capsule Formulation of LGD-6972 to an Oral Solution Formulation in Healthy Adult Subjects [NCT02672839]	Phase 1	12 participants (Actual)	Interventional	2016-02-29	Completed
A Phase I Study to Evaluate the Single and Multiple-dose Pharmacokinetics of Intravenous Trappsol Cyclo (HP-Beta-CD) in Patients With Niemann-Pick Disease Type C (NPC-1) and the Effects of Dosing Upon Biomarkers of NPC Disease [NCT02939547]	Phase 1	13 participants (Actual)	Interventional	2017-10-11	Completed
Hydroxypropyl Beta Cyclodextrin for Niemann-Pick Type C1 Disease [NCT01747135]	Phase 1	14 participants (Actual)	Interventional	2013-01-31	Completed
COVID-19: Nasal and Salivary Detection of the SARS-CoV-2 Virus After Antiviral Mouthrinses: Double-blind, Randomized, Placebo-controlled Clinical Study [NCT04352959]		176 participants (Actual)	Interventional	2020-04-27	Completed
A Randomized, Placebo-controlled, Double-blind, Parallel-group, 6-Month Study to Evaluate the Safety, Tolerability, and Potential Efficacy of Monthly Trappsol® Cyclo™ Infusions in Patients With Early Alzheimer's Disease [NCT05607615]	Phase 2	90 participants (Anticipated)	Interventional	2022-09-23	Recruiting
A Phase 1, Open-label Study in Healthy Female Subjects to Investigate the Effect of JNJ-56136379 at Steady-state on the Single-dose Pharmacokinetics of Ethinylestradiol and Drospirenone (Oral Contraceptive) and on the Single-dose Pharmacokinetics of Midaz [NCT03111511]	Phase 1	18 participants (Actual)	Interventional	2017-03-27	Completed
A Phase 2 Multicenter, Double-masked, Randomized, Vehicle-controlled, Parallel Study to Evaluate the Safety, Efficacy and Pharmacokinetics of CBT-008 in Patients With Meibomian Gland Dysfunction [NCT05261386]	Phase 2	92 participants (Actual)	Interventional	2022-03-24	Completed
Preemptive Use of Piroxicam-beta-Cyclodextrin on Tooth Sensitivity Caused by In-office Bleaching: Randomized, Triple-blind, Controlled Clinical Trial [NCT03153657]	Phase 3	50 participants (Anticipated)	Interventional	2016-12-13	Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
monoisopropanolamine monoisopropanolamine: possible industrial pollutant; structure. 1-aminopropan-2-ol : Any amino alcohol that is propan-2-ol substituted by an amino group at position 1.	2.05	1	0	amino alcohol; secondary alcohol	Escherichia coli metabolite
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	2.05	1	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
keto-pantoyllactone [no description available]	1.98	1	0	tetrahydrofurandione
protocatechuic acid protocatechuic acid: RN given refers to parent cpd; structure. 3,4-dihydroxybenzoic acid : A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4.	2.21	1	0	catechols; dihydroxybenzoic acid	antineoplastic agent; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor; human xenobiotic metabolite; plant metabolite
phosphoserine Phosphoserine: The phosphoric acid ester of serine.	2.04	1	0	non-proteinogenic alpha-amino acid; O-phosphoamino acid; serine derivative	human metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	3.58	8	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
4-hydroxybenzoic acid 4-hydroxybenzoic acid : A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring.	2.54	2	0	monohydroxybenzoic acid	algal metabolite; plant metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.98	4	0	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	4.06	14	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	2.03	1	0	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	3.15	5	0	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
adenine [no description available]	3.85	11	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2.44	2	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
curdlan D-hexose : A hexose that has D-configuration at position 5.	2.21	1	0	hexose
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.15	5	0	azane; gas molecular entity; mononuclear parent hydride	EC 3.5.1.4 (amidase) inhibitor; metabolite; mouse metabolite; neurotoxin; NMR chemical shift reference compound; nucleophilic reagent; refrigerant
anthranilic acid anthranilic acid: RN given refers to parent cpd; structure in Negwer, 5th ed, #565. anthranilic acid : An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.	2.06	1	0	aminobenzoic acid	human metabolite; mouse metabolite
quinacrine Quinacrine: An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.. quinacrine : A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.	2.5	2	0	acridines; aromatic ether; organochlorine compound; tertiary amino compound	antimalarial; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
benzaldehyde [no description available]	2.69	3	0	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
benzene [no description available]	3.84	11	0	aromatic annulene; benzenes; volatile organic compound	carcinogenic agent; environmental contaminant; non-polar solvent
benzoic acid Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.	3.64	9	0	benzoic acids	algal metabolite; antimicrobial food preservative; drug allergen; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; human xenobiotic metabolite; plant metabolite
benzyl alcohol Benzyl Alcohol: A colorless liquid with a sharp burning taste and slight odor. It is used as a local anesthetic and to reduce pain associated with LIDOCAINE injection. Also, it is used in the manufacture of other benzyl compounds, as a pharmaceutic aid, and in perfumery and flavoring.. hydroxytoluene : Any member of the class of toluenes carrying one or more hydroxy substituents.. benzyl alcohol : An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.. aromatic alcohol : Any alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.. aromatic primary alcohol : Any primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.	4.34	4	1	benzyl alcohols	antioxidant; fragrance; metabolite; solvent
betaine glycine betaine : The amino acid betaine derived from glycine.	2.57	2	0	amino-acid betaine; glycine derivative	fundamental metabolite
bis(4-nitrophenyl)phosphate bis(4-nitrophenyl)phosphate: RN given refers to parent cpd	2.5	2	0	aryl phosphate
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.74	3	0	halide anion; monoatomic bromine
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	3.85	11	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
butyric acid Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.	2.44	2	0	fatty acid 4:0; straight-chain saturated fatty acid	human urinary metabolite; Mycoplasma genitalium metabolite
cadaverine [no description available]	4.43	6	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	4.53	23	0	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	3.16	5	0	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	2.77	3	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
carnitine [no description available]	2.43	2	0	amino-acid betaine	human metabolite; mouse metabolite
catechol [no description available]	3.55	8	0	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	6.7	66	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chlordecone [no description available]	2.25	1	0	cyclic ketone; organochlorine compound	insecticide; persistent organic pollutant
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	2.44	2	0	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
choline [no description available]	3.3	6	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	4.3	17	0	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	3.94	12	0	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2.72	3	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
coumarin 2H-chromen-2-one: coumarin derivative	3.3	6	0	coumarins	fluorescent dye; human metabolite; plant metabolite
cuminaldehyde cuminaldehyde : A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.	2.72	2	0	benzaldehydes	insecticide; plant metabolite; volatile oil component
4-hydroxymandelic acid 4-hydroxymandelic acid: RN given refers to cpd without isomeric designation. 4-hydroxymandelic acid : A 2-hydroxy carboxylic acid that is mandelic acid bearing a phenolic hydroxy substituent at position 4.	1.98	1	0	2-hydroxy carboxylic acid; phenols	metabolite
salicylic acid Scalp: The outer covering of the calvaria. It is composed of several layers: SKIN; subcutaneous connective tissue; the occipitofrontal muscle which includes the tendinous galea aponeurotica; loose connective tissue; and the pericranium (the PERIOSTEUM of the SKULL).	5.04	9	1	monohydroxybenzoic acid	algal metabolite; antifungal agent; antiinfective agent; EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor; keratolytic drug; plant hormone; plant metabolite
octane Octanes: Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. octane : A straight chain alkane composed of 8 carbon atoms.	2.05	1	0	alkane	xenobiotic
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	3.54	7	0	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
4-nitrophenylphosphate nitrophenylphosphate: RN given refers to mono(4-nitrophenyl) ester of phosphoric acid. 4-nitrophenyl phosphate : An aryl phosphate resulting from the mono-esterification of phosphoric acid with 4-nitrophenol.	2.77	3	0	aryl phosphate	mouse metabolite
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	2.44	2	0	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
4-aminophenol 4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.	2.52	2	0	aminophenol	allergen; metabolite
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	2.11	1	0	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
guaiacol Guaiacol: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747). methylcatechol : Any member of the class of catechols carrying one or more methyl substituents.. guaiacol : A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.	2.21	1	0	guaiacols	disinfectant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; expectorant; plant metabolite
trimetaphosphoric acid trimetaphosphoric acid: RN given refers to parent cpd; structure. cyclotriphosphoric acid : The cyclic anhydride of triphosphoric acid.	2.5	2	0	cyclic phosphorus acid anhydride; inorganic heterocyclic compound; phosphorus oxoacid
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2.05	1	0	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
4-nitrobenzaldehyde 4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.	2.02	1	0	benzaldehydes; C-nitro compound
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	2.11	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
cytosine [no description available]	2.74	3	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
alanylalanine alanylalanine: RN given refers to (DL)-isomer	2.15	1	0	dipeptide
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	5.15	43	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.15	1	0	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	4.74	29	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
ethanolamine [no description available]	2.77	3	0	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	3.33	6	0	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
formamide formimidic acid : A carboximidic acid that is formic acid in which the carbonyl oxygen is replaced by an imino group.. primary carboxamide : A carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2.	2.41	2	0	carboximidic acid; formamides; monocarboxylic acid amide; one-carbon compound	solvent
glycine [no description available]	4.04	14	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	5.92	30	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
dalteparin Dalteparin: A low-molecular-weight fragment of heparin, prepared by nitrous acid depolymerization of porcine mucosal heparin. The mean molecular weight is 4000-6000 daltons. It is used therapeutically as an antithrombotic agent. (From Merck Index, 11th ed)	2.42	2	0
histamine [no description available]	3.3	6	0	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	5.85	29	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
hydroquinone [no description available]	2.05	1	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	3.46	7	0	imidazole
indole [no description available]	2.52	2	0	indole; polycyclic heteroarene	Escherichia coli metabolite
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.	2.05	1	0	indole-3-acetic acids; monocarboxylic acid	auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite
iodine Iodine: A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.. diiodine : Molecule comprising two covalently bonded iodine atoms with overall zero charge..	2.42	2	0	diatomic iodine	nutrient
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	2.11	1	0	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	3.14	5	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
kynurenine Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.	2.25	1	0	aromatic ketone; non-proteinogenic alpha-amino acid; substituted aniline	human metabolite
2,3,4,5-tetrahydroxypentanal [no description available]	2.6	1	0	hydroxyaldehyde; pentose; polyol
thioctic acid Thioctic Acid: An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.	3.57	8	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	5.47	61	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
phytic acid Phytic Acid: Complexing agent for removal of traces of heavy metal ions. It acts also as a hypocalcemic agent.. myo-inositol hexakisphosphate : A myo-inositol hexakisphosphate in which each hydroxy group of myo-inositol is monophosphorylated.	1.98	1	0	inositol phosphate
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.7	3	0	cyclitol; hexol
melatonin [no description available]	4.13	15	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naphthalene [no description available]	3.41	7	0	naphthalenes; ortho-fused bicyclic arene	apoptosis inhibitor; carcinogenic agent; environmental contaminant; mouse metabolite; plant metabolite; volatile oil component
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	4.14	15	0	metal allergen; nickel group element atom	epitope; micronutrient
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.96	4	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	2.98	4	0	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.38	7	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	2.42	2	0	nitrogen oxoacid
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.94	4	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
nitrous oxide Nitrous Oxide: Nitrogen oxide (N2O). A colorless, odorless gas that is used as an anesthetic and analgesic. High concentrations cause a narcotic effect and may replace oxygen, causing death by asphyxia. It is also used as a food aerosol in the preparation of whipping cream.. dinitrogen oxide : A nitrogen oxide consisting of linear unsymmetrical molecules with formula N2O. While it is the most used gaseous anaesthetic in the world, its major commercial use, due to its solubility under pressure in vegetable fats combined with its non-toxicity in low concentrations, is as an aerosol spray propellant and aerating agent for canisters of 'whipped' cream.	2.11	1	0	gas molecular entity; nitrogen oxide	analgesic; bacterial metabolite; food packaging gas; food propellant; general anaesthetic; greenhouse gas; inhalation anaesthetic; NMDA receptor antagonist; raising agent; refrigerant; vasodilator agent
1-octanol 1-Octanol: A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). octan-1-ol : An octanol carrying the hydroxy group at position 1.	2.78	3	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
hydroxide ion [no description available]	3.14	5	0	oxygen hydride	mouse metabolite
4-aminobenzoic acid 4-Aminobenzoic Acid: An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.. 4-ammoniobenzoate : A zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-aminobenzoic acid.. 4-aminobenzoic acid : An aminobenzoic acid in which the amino group is para to the carboxy group.	3.13	5	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
4-hydroxyphenylpyruvic acid 4-hydroxyphenylpyruvic acid: RN given refers to parent cpd. 4-hydroxyphenylpyruvic acid : A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.	2.03	1	0	2-oxo monocarboxylic acid; phenols	human metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	4.36	19	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
triphosphoric acid triphosphoric acid: used as water softener, peptizing agent, emulsifier & dispersing agent; ingredient of cleansers; meat preservative; RN given refers to parent cpd; structure	3.02	4	0	acyclic phosphorus acid anhydride; phosphorus oxoacid
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	3.82	11	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
parathion [no description available]	2.76	3	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; avicide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; mouse metabolite
pentachlorophenol PENTA: structure given in first source	2.94	4	0	aromatic fungicide; chlorophenol; organochlorine pesticide; pentachlorobenzenes	human xenobiotic metabolite
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	4.36	19	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phenol [no description available]	3.14	5	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
2-hydroxyphenethylamine 2-amino-1-phenylethanol: structure in first source	2.11	1	0	phenylethanolamines	human metabolite
phenethylamine phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.	2.54	2	0	alkaloid; aralkylamine; phenylethylamine	Escherichia coli metabolite; human metabolite; mouse metabolite
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2.73	3	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	4.45	6	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse metabolite
phosphorylethanolamine phosphorylethanolamine: RN given refers to parent cpd; structure. O-phosphoethanolamine : The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain.	2.78	3	0	phosphoethanolamine; primary amino compound	algal metabolite; human metabolite; mouse metabolite
phthalic acid phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.	4.09	4	0	benzenedicarboxylic acid	human xenobiotic metabolite
diphosphoric acid diphosphoric acid : An acyclic phosphorus acid anhydride obtained by condensation of two molecules of phosphoric acid.	2.06	1	0	acyclic phosphorus acid anhydride; phosphorus oxoacid	Escherichia coli metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	5.81	21	1	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.39	2	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.41	2	0	saturated fatty acid; short-chain fatty acid	antifungal drug
putrescine [no description available]	1.97	1	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	3.55	8	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxine 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol: structure in first source. vitamin B6 : Any member of the group of pyridines that exhibit biological activity against vitamin B6 deficiency. Vitamin B6 deficiency is associated with microcytic anemia, electroencephalographic abnormalities, dermatitis with cheilosis (scaling on the lips and cracks at the corners of the mouth) and glossitis (swollen tongue), depression and confusion, and weakened immune function. Vitamin B6 consists of the vitamers pyridoxine, pyridoxal, and pyridoxamine and their respective 5'-phosphate esters (and includes their corresponding ionized and salt forms).	2.25	1	0	hydroxymethylpyridine; methylpyridines; monohydroxypyridine; vitamin B6	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
pyrogallol benzenetriol : A triol in which three hydroxy groups are substituted onto a benzene ring.	2.1	1	0	benzenetriol; phenolic donor	plant metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.48	2	0	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
sulfites Sulfites: Inorganic salts of sulfurous acid.. sulfites : Any sulfurous acid derivative that is a salt or an ester of sulfurous acid.. organosulfonate oxoanion : An organic anion obtained by deprotonation of the sufonate group(s) of any organosulfonic acid.. sulfite : A sulfur oxoanion that is the conjugate base of hydrogen sulfite (H2SO3).	3.14	5	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	3.17	5	0	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
sulfuric acid sulfuric acid : A sulfur oxoacid that consists of two oxo and two hydroxy groups joined covalently to a central sulfur atom.	2.77	3	0	sulfur oxoacid	catalyst
sulfur dioxide Sulfur Dioxide: A highly toxic, colorless, nonflammable gas. It is used as a pharmaceutical aid and antioxidant. It is also an environmental air pollutant.	2.41	1	0	sulfur oxide	Escherichia coli metabolite; food bleaching agent; refrigerant
taurine [no description available]	2.73	3	0	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
thiophane [no description available]	2.03	1	0	saturated organic heteromonocyclic parent; tetrahydrothiophenes
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	2.98	4	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
thymine [no description available]	2.42	2	0	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	3.88	12	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	3.45	7	0	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	4.56	24	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	3.61	8	0	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
xanthine 7H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-7 is protonated.. 9H-xanthine : An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated.	2.95	4	0	xanthine	Saccharomyces cerevisiae metabolite
8-hydroxy-2-(di-n-propylamino)tetralin 8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively	2.43	2	0	phenols; tertiary amino compound; tetralins	serotonergic antagonist
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	3.75	10	0	p-menthane monoterpenoid; secondary alcohol	volatile oil component
perillic acid perillic acid: d-limonene metabolite; structure given in first source	2.11	1	0	alpha,beta-unsaturated monocarboxylic acid; cyclohexenecarboxylic acid	antineoplastic agent; human metabolite; mouse metabolite
mandelic acid SAMMA: mandelic acid condensation polymer	3.65	9	0	2-hydroxy monocarboxylic acid; benzenes	antibacterial agent; human xenobiotic metabolite
atrolactic acid atrolactic acid: see also 3-isomer; RN given refers to parent cpd without isomeric designation; structure	1.98	1	0	2-hydroxy monocarboxylic acid
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.51	2	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	4.23	17	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methylimidazole 1-methyl-1H-imidazole : A 1H-imidazole having a methyl substituent at the N-1 position.	2.76	3	0	imidazoles
edelfosine edelfosine: RN given refers to parent cpd. edelfosine : A racemate comprising equimolar amounts of (R)- and (S)-edelfosine.. 1-octadecyl-2-methylglycero-3-phosphocholine : A glycerophosphocholine that is glycero-3-phosphocholine substituted at positions 1 and 2 by octadecyl and methyl groups respectively.	2.44	2	0	glycerophosphocholine
1-oleoyl-2-acetoyl-sn-glycerol [no description available]	2.05	1	0
n-(3-(aminomethyl)benzyl)acetamidine N-(3-(aminomethyl)benzyl)acetamidine: structure in first source. N-[3-(aminomethyl)benzyl]acetamidine : An aralkylamine that is Nbenzylacetamidine substituted at position 3 on the benzene ring by an aminomethyl group. An inhibitor of nitric oxide synthase.	2.17	1	0	aralkylamine; carboxamidine; primary amino compound	angiogenesis inhibitor; EC 1.14.13.39 (nitric oxide synthase) inhibitor; geroprotector
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	3.44	7	0	bipyridine	chelator; ferroptosis inhibitor
2,4,5-trichlorophenoxyacetic acid 2,4,5-Trichlorophenoxyacetic Acid: An herbicide with strong irritant properties. Use of this compound on rice fields, orchards, sugarcane, rangeland, and other noncrop sites was terminated by the EPA in 1985. (From Merck Index, 11th ed). (2,4,5-trichlorophenoxy)acetic acid : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2, 4 and 5 are substituted by chlorines.	2.08	1	0	chlorophenoxyacetic acid; trichlorobenzene	defoliant; phenoxy herbicide; synthetic auxin
2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.	3.54	8	0	chlorophenoxyacetic acid; dichlorobenzene	agrochemical; defoliant; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; environmental contaminant; phenoxy herbicide; synthetic auxin
2,4-dinitrophenol 2,4-Dinitrophenol: A toxic dye, chemically related to trinitrophenol (picric acid), used in biochemical studies of oxidative processes where it uncouples oxidative phosphorylation. It is also used as a metabolic stimulant. (Stedman, 26th ed). dinitrophenol : Members of the class of nitrophenol carrying two nitro substituents.. 2,4-dinitrophenol : A dinitrophenol having the nitro groups at the 2- and 4-positions.	2.49	2	0	dinitrophenol	allergen; antiseptic drug; bacterial xenobiotic metabolite; geroprotector; oxidative phosphorylation inhibitor
2-aminofluorene [no description available]	2.43	2	0
mercaptoethanol Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.	1.99	1	0	alkanethiol; primary alcohol	geroprotector
monomethylpropion monomethylpropion: metabolite of dimethylpropion; structure given in first source. 2-methylamino-1-phenylpropan-1-one : An aromatic ketone that is propiophenone in which the hydrogen alpha- to the keto group has been replaced by a methylamino group.. methcathinone : A racemate comprising equal amounts of (R)- and (S)-methcathinone.	2.17	1	0	aromatic ketone; secondary amino compound
3,4-methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine: An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally.	2.02	1	0	benzodioxoles
n-methyl-3,4-methylenedioxyamphetamine N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.. 3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.	2.41	2	0	amphetamines; benzodioxoles	neurotoxin
4-amino-1,8-naphthalimide 4-amino-1,8-naphthalimide: inhibits ADP-ribosylation; sometimes abreviated as 4-AN;	2.05	1	0	benzoisoquinoline; dicarboximide
5,5-dimethyl-1-pyrroline-1-oxide 5,5-dimethyl-1-pyrroline-1-oxide: do not confuse with DMPO (4',5'-dihydroxy-7-methoxy-4-phenyl-5,2'-oxidocoumarin). 5,5-dimethyl-1-pyrroline N-oxide : A member of the class of 1-pyrroline nitrones (1-pyrroline N-oxides) resulting from the formal N-oxidation of 5,5-dimethyl-1-pyrroline. Used as a spin trap for the study of radicals formed by enzymatic acetaldehyde oxidation.	2.06	1	0	1-pyrroline nitrones	neuroprotective agent; spin trapping reagent
phenytoin [no description available]	3.71	10	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5-dimethylamiloride 5-dimethylamiloride: has anti-HIV-1 activity	2.45	2	0
ethylisopropylamiloride ethylisopropylamiloride: structure in first source. ethylisopropylamiloride : A member of the class of pyrazines that is amiloride in which the amino substitutent of the pyrazine ring that is adjacent to the chloro substituent has been substituted by an ethyl group and by an isopropyl group.	2.05	1	0	aromatic amine; guanidines; monocarboxylic acid amide; organochlorine compound; pyrazines; tertiary amino compound	anti-arrhythmia drug; neuroprotective agent; sodium channel blocker
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	2.17	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.	2.74	3	0	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist
oxyquinoline Oxyquinoline: An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.. quinolin-8-ol : A monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes.	2.48	2	0	monohydroxyquinoline	antibacterial agent; antifungal agrochemical; antiseptic drug; iron chelator
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.06	1	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	2.44	2	0	monoazo compound
acemetacin acemetacin : A carboxylic ester that is the carboxymethyl ester of indometacin. A non-steroidal anti-inflammatory drug, it is used in the treatment of rheumatoid arthritis, osteoarthritis, and low back pain, as well as for postoperative pain and inflammation. Its activity is due to both acemetacin and its major metabolite, indometacin.	2.01	1	0	carboxylic ester; indol-3-yl carboxylic acid; monocarboxylic acid; monochlorobenzenes; N-acylindole	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
acetaminophen Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	6.3	19	2	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
salophen salophen: structure given in first source	2.06	1	0	carbonyl compound
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	4.75	9	0	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
acetohexamide Acetohexamide: A sulfonylurea hypoglycemic agent that is metabolized in the liver to 1-hydrohexamide.. acetohexamide : An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a p-acetylphenylsulfonyl group, while a hydrogen attached to the other nitrogen is replaced by a cyclohexyl group.	3.63	2	0	acetophenones; N-sulfonylurea	hypoglycemic agent; insulin secretagogue
n-acetylphenylalanine N-acetylphenylalanine: RN given refers to (DL)-isomer. N-acetylphenylalanine : The N-acetyl derivative of phenylalanine.	2.42	2	0	N-acetyl-amino acid; phenylalanine derivative	antidepressant; metabolite
albendazole [no description available]	5.99	24	1	aryl sulfide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	anthelminthic drug; microtubule-destabilising agent; tubulin modulator
albuterol Albuterol: A short-acting beta-2 adrenergic agonist that is primarily used as a bronchodilator agent to treat ASTHMA. Albuterol is prepared as a racemic mixture of R(-) and S(+) stereoisomers. The stereospecific preparation of R(-) isomer of albuterol is referred to as levalbuterol.. albuterol : A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).	4.06	14	0	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic
alendronate alendronic acid : A 1,1-bis(phosphonic acid) that is methanebis(phosphonic acid) in which the two methylene hydrogens are replaced by hydroxy and 3-aminopropyl groups.	2.99	4	0	1,1-bis(phosphonic acid); primary amino compound	bone density conservation agent; EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor
alprazolam Alprazolam: A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of PANIC DISORDERS, with or without AGORAPHOBIA, and in generalized ANXIETY DISORDERS. (From AMA Drug Evaluations Annual, 1994, p238). alprazolam : A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.	2.01	1	0	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic
alprenolol Alprenolol: One of the ADRENERGIC BETA-ANTAGONISTS used as an antihypertensive, anti-anginal, and anti-arrhythmic agent.. alprenolol : A secondary alcohol that is propan-2-ol substituted by a 2-allylphenoxy group at position 1 and an isopropylamino group at position 3. It is a beta-adrenergic antagonist used as a antihypertensive, anti-arrhythmia and a sympatholytic agent.	2.49	2	0	secondary alcohol; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
altretamine Altretamine: A hexamethyl-2,4,6-triamine derivative of 1,3,5-triazine.	2.15	1	0	triamino-1,3,5-triazine
am 251 AM 251: an analog of SR141716A; structure given in first source. AM-251 : A carbohydrazide obtained by formal condensation of the carboxy group of 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. An antagonist at the CB1 cannabinoid receptor.	3.37	2	0	amidopiperidine; carbohydrazide; dichlorobenzene; organoiodine compound; pyrazoles	antidepressant; antineoplastic agent; apoptosis inducer; CB1 receptor antagonist
amantadine amant: an antiviral compound consisting of an adamantane derivative chemically linked to a water-solube polyanioic matrix; structure in first source	4.27	17	0	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
ambroxol Ambroxol: A metabolite of BROMHEXINE that stimulates mucociliary action and clears the air passages in the respiratory tract. It is usually administered as the hydrochloride.	3.46	1	1	aromatic amine
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	2.72	3	0	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
theophylline [no description available]	3.28	6	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
amiodarone Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.	6.21	9	1	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug
dan 2163 [no description available]	2.49	2	0	aromatic amide; aromatic amine; benzamides; pyrrolidines; sulfone	environmental contaminant; second generation antipsychotic; xenobiotic
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	2.77	3	0	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
amlodipine Amlodipine: A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION.. amlodipine : A fully substituted dialkyl 1,4-dihydropyridine-3,5-dicarboxylate derivative, which is used for the treatment of hypertension, chronic stable angina and confirmed or suspected vasospastic angina.	3.8	10	0	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
amobarbital Amobarbital: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565). amobarbital : A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by a 3-methylbutyl and an ethyl group at position 5. Amobarbital has been shown to exhibit sedative and hypnotic properties.	2	1	0	barbiturates
amoxapine Amoxapine: The N-demethylated derivative of the antipsychotic agent LOXAPINE that works by blocking the reuptake of norepinephrine, serotonin, or both; it also blocks dopamine receptors. Amoxapine is used for the treatment of depression.. amoxapine : A dibenzooxazepine compound having a chloro substituent at the 2-position and a piperazin-1-yl group at the 11-position.	2.06	1	0	dibenzooxazepine	adrenergic uptake inhibitor; antidepressant; dopaminergic antagonist; geroprotector; serotonin uptake inhibitor
amsacrine Amsacrine: An aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.. amsacrine : A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.	2.11	1	0	acridines; aromatic ether; sulfonamide	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
9-anthroic acid 9-anthroic acid: RN given refers to unlabeled parent cpd; chloride channel blocker; do not confuse with c-ANCA (anti-neutrophil cytoplasmic antibodies) which is frequently abbreviated as ANCA. 9-anthroic acid : An anthroic acid carrying the carboxy substituent at position 9.	2.07	1	0	anthroic acid
anthralin Anthralin: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.. anthralin : An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.	1.99	1	0	anthracenes	antipsoriatic
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	3.01	4	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
acetovanillone apocynin : An aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3.	2.97	4	0	acetophenones; aromatic ketone; methyl ketone	antirheumatic drug; EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite
aristolochic acid i aristolochic acid I: phospholipase A inhibitor. aristolochic acid A : An aristolochic acid that is phenanthrene-1-carboxylic acid that is substituted by a methylenedioxy group at the 3,4 positions, by a methoxy group at position 8, and by a nitro group at position 10. It is the most abundant of the aristolochic acids and is found in almost all Aristolochia (birthworts or pipevines) species. It has been tried in a number of treatments for inflammatory disorders, mainly in Chinese and folk medicine. However, there is concern over their use as aristolochic acid is both carcinogenic and nephrotoxic.	2.43	2	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	6.41	12	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
atenolol Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.	4.03	13	0	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic
atrazine [no description available]	2.61	2	0	chloro-1,3,5-triazine; diamino-1,3,5-triazine	environmental contaminant; herbicide; xenobiotic
aurintricarboxylic acid Aurintricarboxylic Acid: A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.. aurintricarboxylic acid : A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'.	2.4	2	0	monohydroxybenzoic acid; quinomethanes; tricarboxylic acid	fluorochrome; histological dye; insulin-like growth factor receptor 1 antagonist
azelaic acid nonanedioic acid : An alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.	2.02	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	antibacterial agent; antineoplastic agent; dermatologic drug; plant metabolite
azobenzene azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.	5.24	45	0	azobenzenes
baclofen [no description available]	3.43	7	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
bay-k-8644 3-Pyridinecarboxylic acid, 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-(trifluoromethyl)phenyl)-, Methyl ester: A dihydropyridine derivative, which, in contrast to NIFEDIPINE, functions as a calcium channel agonist. The compound facilitates Ca2+ influx through partially activated voltage-dependent Ca2+ channels, thereby causing vasoconstrictor and positive inotropic effects. It is used primarily as a research tool.. Bay-K-8644 : A racemate comprising equimolar amounts of (R)- and (S)-Bay-K-8644. methyl 2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate : A pentasubstituted dihydropyridine carrying methoxycarbonyl, 2-(trifluoromethyl)phenyl and nitro substituents at positions 3, 4 and 5 respectively as well as two methyl substituents at positions 2 and 6.	2.04	1	0	(trifluoromethyl)benzenes; C-nitro compound; dihydropyridine; methyl ester
bendroflumethiazide Bendroflumethiazide: A thiazide diuretic with actions and uses similar to those of HYDROCHLOROTHIAZIDE. It has been used in the treatment of familial hyperkalemia, hypertension, edema, and urinary tract disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p810). bendroflumethiazide : A sulfonamide consisting of 7-sulfamoyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by a trifluoromethyl group and that at position 3 is substituted by a benzyl group.	2.37	2	0	benzothiadiazine; sulfonamide	antihypertensive agent; diuretic
benphothiamine benfotiamine : A thioester that is a synthetic analogue of thiamine obtained by acylative cleavage of the thiazole ring and O-phospohorylation.	1.98	1	0	aminopyrimidine; formamides; organic phosphate; thioester	antioxidant; immunological adjuvant; nutraceutical; protective agent; provitamin B1
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.44	2	0	benzamides
benzo(a)pyrene Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.	4.66	10	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
benzocaine Benzocaine: A surface anesthetic that acts by preventing transmission of impulses along NERVE FIBERS and at NERVE ENDINGS.. dextran sulfate sodium : An organic sodium salt of dextran sulfate. It induces colitis in mice.. benzocaine : A benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina.	2.95	4	0	benzoate ester; substituted aniline	allergen; antipruritic drug; sensitiser; topical anaesthetic
benzothiazide benzothiazide: structure. benzthiazide : 7-Sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by chlorine and that at position 3 is substituted by a benzylsulfanylmethyl group. A diuretic, it is used to treat hypertension and edema.	2.15	1	0	benzothiadiazine; sulfonamide	antihypertensive agent; diuretic
benzyl benzoate benzyl benzoate: structure; acarosan, a moist powder composed of wetted cellulose and benzyl benzoate, is used on carpets as an acaricide. benzyl benzoate : A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia.	2.31	1	0	benzoate ester; benzyl ester	acaricide; plant metabolite; scabicide
benzyl isothiocyanate benzyl isothiocyanate: inhibits carcinogen-induced neoplasia; structure in Negwer, 5th ed, #715; also promotes urinary bladder carcinoma	3.08	4	0	benzenes; isothiocyanate	antibacterial drug
berberine [no description available]	4.36	18	0	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
5-methoxypsoralen 5-Methoxypsoralen: A linear furanocoumarin that has phototoxic and anti-inflammatory properties, with effects similar to METHOXSALEN. It is used in PUVA THERAPY for the treatment of PSORIASIS.. 5-methoxypsoralen : A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.	2.42	2	0	5-methoxyfurocoumarin; organic heterotricyclic compound; psoralens	hepatoprotective agent; plant metabolite
beta-naphthoflavone beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.	2.13	1	0	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist
bicalutamide bicalutamide: approved for treatment of advanced prostate cancer. N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide : A member of the class of (trifluoromethyl)benzenes that is 4-amino-2-(trifluoromethyl)benzonitrile in which one of the amino hydrogens is substituted by a 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanoyl group.. bicalutamide : A racemate comprising of equal amounts of (R)-bicalutamide and (S)-bicalutamide. It is an oral non-steroidal antiandrogen used in the treatment of prostate cancer and hirsutism.	2.04	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol
bay h 4502 bifonazole : A racemate comprising equimolar amounts of R- and S-bifonazole. It is a broad spectrum antifungal drug used for the treatment of fungal skin and nail infections.. 1-[biphenyl-4-yl(phenyl)methyl]imidazole : A member of the class of imidazoles carrying an alpha-(biphenyl-4-yl)benzyl substituent at position 1.	2	1	0	biphenyls; imidazoles
bisacodyl Bisacodyl: A diphenylmethane stimulant laxative used for the treatment of CONSTIPATION and for bowel evacuation. (From Martindale, The Extra Pharmacopoeia, 30th ed, p871)	2.52	2	0	diarylmethane
bisbenzimidazole Bisbenzimidazole: A benzimidazole antifilarial agent; it is fluorescent when it binds to certain nucleotides in DNA, thus providing a tool for the study of DNA replication; it also interferes with mitosis.	2.03	1	0	bibenzimidazole; N-methylpiperazine	anthelminthic drug; fluorochrome
bisoprolol Bisoprolol: A cardioselective beta-1 adrenergic blocker. It is effective in the management of HYPERTENSION and ANGINA PECTORIS.	2.11	1	0	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent
bromazepam Bromazepam: One of the BENZODIAZEPINES that is used in the treatment of ANXIETY DISORDERS.	2.01	1	0	organic molecular entity
bromhexine Bromhexine: A mucolytic agent used in the treatment of respiratory disorders associated with viscid or excessive mucus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p744). bromhexine : A substituted aniline that is 2,4-dibromoaniline which is substituted at position 6 by a [cyclohexyl(methyl)amino]methyl group. It is used (as the monohydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive cough (i.e. a cough characterised by the production of sputum).	2.07	1	0	organobromine compound; substituted aniline; tertiary amino compound	mucolytic
bufexamac Bufexamac: A benzeneacetamide with anti-inflammatory, analgesic, and antipyretic action. It is administered topically, orally, or rectally.. bufexamac : A hydroxamic acid derived from phenylacetamide in which the benzene moiety is substituted at C-4 by a butoxy group. It has anti-inflammatory, analgesic, and antipyretic properties.	2.06	1	0	aromatic ether; hydroxamic acid	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug
bupivacaine Bupivacaine: A widely used local anesthetic agent.. 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide : A piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline.. bupivacaine : A racemate composed of equimolar amounts of dextrobupivacaine and levobupivacaine. Used (in the form of its hydrochloride hydrate) as a local anaesthetic.	4.17	16	0	aromatic amide; piperidinecarboxamide; tertiary amino compound
bupranolol Bupranolol: An adrenergic-beta-2 antagonist that has been used for cardiac arrhythmia, angina pectoris, hypertension, glaucoma, and as an antithrombotic.	2.73	3	0	aromatic ether
buspirone Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.	2.47	2	0	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist
butamben butamben: structure. butamben : An amino acid ester resulting from the formal condensation of the carboxy group of 4-aminobenzoic acid with the hydroxy group of butan-1-ol. Its local anaesthetic properties have been used for surface anaesthesia of the skin and mucous membranes, and for relief of pain and itching associated with some anorectal disorders.	2.05	1	0	amino acid ester; benzoate ester; primary amino compound; substituted aniline	local anaesthetic
caffeine [no description available]	3.94	12	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	3.83	11	0	aromatic ether; nitrile; polyether; tertiary amino compound
beta-glycerophosphoric acid beta-glycerophosphoric acid: plays role in mineralization of bone in vitro. glycerol 2-phosphate : A glycerol monophosphate having the phosphate group at the 2-position.	2.13	1	0	glycerol monophosphate	Escherichia coli metabolite; plant metabolite
camphor, (+-)-isomer [no description available]	3.12	5	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
candesartan cilexetil candesartan cilexetil: a prodrug which is metabolized to an active form candesartan to exert its biological effects	2.06	1	0	biphenyls
carbamazepine Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.	4.38	20	0	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic
carbofuran Carbofuran: A cholinesterase inhibitor that is used as a systemic insecticide, an acaricide, and nematocide. (From Merck Index, 11th ed)	2.01	1	0	1-benzofurans; carbamate ester	acaricide; agrochemical; avicide; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nematicide
carmofur [no description available]	2.66	3	0	organohalogen compound; pyrimidines
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	2	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
carprofen carprofen: RN given refers to cpd without isomeric designation. carprofen : Propanoic acid in which one of the methylene hydrogens is substituted by a 6-chloro-9H-carbazol-2-yl group. A non-steroidal anti-inflammatory drug, it is no longer used in human medicine but is still used for treatment of arthritis in elderly dogs.	2.77	3	0	carbazoles; organochlorine compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug; photosensitizing agent
carvedilol [no description available]	3.92	12	0	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent
celecoxib [no description available]	4.07	14	0	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug
celiprolol Celiprolol: A cardioselective beta-1 adrenergic antagonist that has intrinsic sympathomimetic activity. It is used in the management of ANGINA PECTORIS and HYPERTENSION.	2	1	0	aromatic ketone
cefixime Cefixime: A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.. cefixime : A third-generation cephalosporin antibiotic bearing vinyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used in the treatment of gonorrhoea, tonsilitis, pharyngitis, bronchitis, and urinary tract infections.	2.46	2	0
cetirizine Cetirizine: A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects.. cetirizine : A member of the class of piperazines that is piperazine in which the hydrogens attached to nitrogen are replaced by a (4-chlorophenyl)(phenyl)methyl and a 2-(carboxymethoxy)ethyl group respectively.	4.96	8	1	ether; monocarboxylic acid; monochlorobenzenes; piperazines	anti-allergic agent; environmental contaminant; H1-receptor antagonist; xenobiotic
cetyltrimethylammonium ion Cetrimonium: Cetyltrimethylammonium compound whose salts and derivatives are used primarily as topical antiseptics.. cetyltrimethylammonium ion : A quaternary ammonium ion in which the substituents on nitrogen are one hexadecyl and three methyl groups.	4.3	18	0	quaternary ammonium ion
cetyl alcohol cetyl alcohol: has been used for eczema, skin irritations; RN given refers to parent cpd; structure. hexadecanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of sixteen carbon atoms.. hexadecan-1-ol : A long-chain primary fatty alcohol that is hexadecane substituted by a hydroxy group at position 1.	2.44	2	0	hexadecanol; long-chain primary fatty alcohol	algal metabolite; flavouring agent; human metabolite; plant metabolite
cetylpyridinium Cetylpyridinium: Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.	2.1	1	0	pyridinium ion
chelerythrine chelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.	2.11	1	0	benzophenanthridine alkaloid; organic cation	antibacterial agent; antineoplastic agent; EC 2.7.11.13 (protein kinase C) inhibitor
chlorambucil Chlorambucil: A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed). chlorambucil : A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.	3.1	5	0	aromatic amine; monocarboxylic acid; nitrogen mustard; organochlorine compound; tertiary amino compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	3.65	9	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
chlorothiazide Chlorothiazide: A thiazide diuretic with actions and uses similar to those of HYDROCHLOROTHIAZIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p812). thiazide : Heterocyclic compound with sulfur and nitrogen in the ring.. chlorothiazide : 4H-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position is substituted by chlorine and that at position 7 is substituted by a sulfonamide group. A diuretic, it is used for treatment of oedema and hypertension.	1.96	1	0	benzothiadiazine	antihypertensive agent; diuretic
chlorpheniramine Chlorpheniramine: A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than PROMETHAZINE.. chlorphenamine : A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.	5.36	13	1	monochlorobenzenes; pyridines; tertiary amino compound	anti-allergic agent; antidepressant; antipruritic drug; H1-receptor antagonist; histamine antagonist; serotonin uptake inhibitor
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	4.79	30	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
chlorpropamide Chlorpropamide: A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277). chlorpropamide : An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is substituted by 4-chlorobenzenesulfonyl group and a hydrogen attached to the other nitrogen is substituted by propyl group. Chlorpropamide is a hypoglycaemic agent used in the treatment of type 2 (non-insulin-dependent) diabetes mellitus not responding to dietary modification.	2.05	1	0	monochlorobenzenes; N-sulfonylurea	hypoglycemic agent; insulin secretagogue
chlorpropham Chlorpropham: A carbamate that is used as an herbicide and as a plant growth regulator.. chlorpropham : A carbamate ester that is the isopropyl ester of 3-chlorophenylcarbamic acid.	2.82	3	0	benzenes; carbamate ester; monochlorobenzenes	herbicide; plant growth retardant
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.79	3	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
chlorthalidone Chlorthalidone: A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.	3.13	5	0	isoindoles; monochlorobenzenes; sulfonamide
chlorzoxazone Chlorzoxazone: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202). chlorzoxazone : A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm.	2.11	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
chrysanthemic acid chrysanthemic acid: occurs as esters in pyrethrum flowers; RN given refers to cpd without isomeric designation; structure. chrysanthemic acid : A monocarboxylic acid that is cyclopropanecarboxylic acid substituted by two methyl groups at position 2 and a 2-methylprop-1-en-1-yl group at position 3.	2	1	0	cyclopropanes; monocarboxylic acid	plant metabolite
ciclopirox [no description available]	2.77	3	0	cyclic hydroxamic acid; hydroxypyridone antifungal drug; pyridone	antibacterial agent; antiseborrheic
cilostazol [no description available]	2.97	4	0	lactam; tetrazoles	anticoagulant; bronchodilator agent; EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor; fibrin modulating drug; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	1.99	1	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
eucalyptol [no description available]	2.52	2	0
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	5.65	17	1	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
cisapride Cisapride: A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). cisapride : The amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere.	2.03	1	0	benzamides
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	3.77	10	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
clenbuterol Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	3.75	10	0	amino alcohol; dichlorobenzene; ethanolamines; primary arylamine; secondary amino compound; substituted aniline	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent
clobazam Clobazam: A benzodiazepine derivative that is a long-acting GABA-A RECEPTOR agonist. It is used as an antiepileptic in the treatment of SEIZURES, including seizures associated with LENNOX-GASTAUT SYNDROME. It is also used as an anxiolytic, for the short-term treatment of acute ANXIETY.. clobazam : 7-Chloro-1H-1,5-benzodiazepine-2,4(3H,5H)-dione in which the hydrogen attached to the nitrogen at position 1 is substituted by a methyl group, whilst that attached to the other nitrogen is substituted by a phenyl group. It is used for the short-term management of acute anxiety and as an adjunct in the treatment of epilepsy in association with other antiepileptics.	1.97	1	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; GABA modulator
clofazimine Clofazimine: A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619). clofazimine : 3-Isopropylimino-3,5-dihydro-phenazine in which the hydrogen at position 5 is substituted substituted by a 4-chlorophenyl group, and that at position 2 is substituted by a (4-chlorophenyl)amino group. A dark red crystalline solid, clofazimine is an antimycobacterial and is one of the main drugs used for the treatment of multi-bacillary leprosy. However, it can cause red/brown discolouration of the skin, so other treatments are often preferred in light-skinned patients.	2.17	1	0	monochlorobenzenes; phenazines	dye; leprostatic drug; non-steroidal anti-inflammatory drug
clofibrate angiokapsul: contains clofibrate & insoitolnicotinate	2.03	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
clofibric acid Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.	2.03	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes	anticholesteremic drug; antilipemic drug; antineoplastic agent; herbicide; marine xenobiotic metabolite; PPARalpha agonist
clomipramine Clomipramine: A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.. clomipramine : A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.	2.45	2	0	dibenzoazepine	anticoronaviral agent; antidepressant; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; serotonergic antagonist; serotonergic drug; serotonin uptake inhibitor
clonazepam Clonazepam: An anticonvulsant used for several types of seizures, including myotonic or atonic seizures, photosensitive epilepsy, and absence seizures, although tolerance may develop. It is seldom effective in generalized tonic-clonic or partial seizures. The mechanism of action appears to involve the enhancement of GAMMA-AMINOBUTYRIC ACID receptor responses.. clonazepam : 1,3-Dihydro-2H-1,4-benzodiazepin-2-one in which the hydrogens at positions 5 and 7 are substituted by 2-chlorophenyl and nitro groups, respectively. It is used in the treatment of all types of epilepsy and seizures, as well as myoclonus and associated abnormal movements, and panic disorders. However, its use can be limited by the development of tolerance and by sedation.	2.47	2	0	1,4-benzodiazepinone; monochlorobenzenes	anticonvulsant; anxiolytic drug; GABA modulator
clonidine Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.	2.73	3	0	clonidine; imidazoline
clorprenaline clorprenaline : A racemate comprise of equimolar amounts of (R)- and (S)-clorprenaline. It is a beta2-adrenergic receptor agonist and a bronchodilator.. 1-(2-chlorophenyl)-2-isopropylaminoethanol : A member of the class of monochlorobenzenes that is chlorobenzene which is substituted by a 1-hydroxy-2-[(propan-2-yl)amino]ethyl group at position 2.	2.21	1	0	ethanolamines; monochlorobenzenes; secondary amino compound
clotrimazole [no description available]	3.55	8	0	conazole antifungal drug; imidazole antifungal drug; imidazoles; monochlorobenzenes	antiinfective agent; environmental contaminant; xenobiotic
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.21	1	0	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
cyclopenthiazide Cyclopenthiazide: Thiazide diuretic also used as an antihypertensive agent.	1.97	1	0	benzothiadiazine
cypermethrin cypermethrin : A carboxylic ester resulting from the formal condensation between 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid and the alcoholic hydroxy group of hydroxy(3-phenoxyphenyl)acetonitrile.. zeta-cypermethrin : A diastereoisomeric mixture comprising the isomeric pair (1R)-cis-(alphaS)- and (1S)-trans-(alphaR)-cypermethrin together with the isomeric pair (1S)-cis-(alphaS)- and (1S)-trans-(alphaS)-cypermethrin where the ratio between the isomeric pairs lies in the range 45:55 to 55:45.	3.33	6	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound	agrochemical; molluscicide; pyrethroid ester acaricide; pyrethroid ester insecticide
dimethyl 2,3,5,6-tetrachloroterephthalate dimethyl 2,3,5,6-tetrachloroterephthalate: structure	2.6	1	0	diester; methyl ester
danthron danthron: structure. chrysazin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 8.	2.52	2	0	dihydroxyanthraquinone	apoptosis inducer; plant metabolite
dantrolene Dantrolene: Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.. dantrolene : The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.	2.15	1	0	hydrazone; imidazolidine-2,4-dione	muscle relaxant; neuroprotective agent; ryanodine receptor antagonist
dapi DAPI: RN given refers to parent cpd.	2.42	2	0	indoles	fluorochrome
dapsone [no description available]	2.81	3	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
decanoic acid decanoate : A fatty acid anion 10:0 that is the conjugate base of decanoic acid.. decanoic acid : A C10, straight-chain saturated fatty acid.	3	4	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; anti-inflammatory agent; antibacterial agent; human metabolite; plant metabolite; volatile oil component
deferiprone Deferiprone: A pyridone derivative and iron chelator that is used in the treatment of IRON OVERLOAD in patients with THALASSEMIA.. deferiprone : A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.	2.07	1	0	4-pyridones	iron chelator; protective agent
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	2.11	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
dequalinium Dequalinium: A topical bacteriostat that is available as various salts. It is used in wound dressings and mouth infections and may also have antifungal action, but may cause skin ulceration.. dequalinium : A quinolinium ion comprising decane in which one methyl hydrogen at each end of the molecule has been replaced by a 4-amino-2-methylquinolin-1-yl group.	2.02	1	0	quinolinium ion	antifungal agent; antineoplastic agent; antiseptic drug; mitochondrial NADH:ubiquinone reductase inhibitor
desipramine Desipramine: A tricyclic dibenzazepine compound that potentiates neurotransmission. Desipramine selectively blocks reuptake of norepinephrine from the neural synapse, and also appears to impair serotonin transport. This compound also possesses minor anticholinergic activity, through its affinity to muscarinic receptors.. desipramine : A dibenzoazepine consisting of 10,11-dihydro-5H-dibenzo[b,f]azepine substituted on nitrogen with a 3-(methylamino)propyl group.	3.15	5	0	dibenzoazepine; secondary amino compound	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; cholinergic antagonist; drug allergen; EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; serotonin uptake inhibitor
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	3.29	6	0	primary amine
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	3.43	7	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
diazinon Diazinon: A cholinesterase inhibitor that is used as an organothiophosphorus insecticide.. diazinon : A member of the class of pyrimidines that is pyrimidine carrying an isopropyl group at position 2, a methyl group at position 6 and a (diethoxyphosphorothioyl)oxy group at position 4.	2.57	2	0	organic thiophosphate; pyrimidines	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; nematicide; xenobiotic
diazoxide Diazoxide: A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group.. diazoxide : A benzothiadiazine that is the S,S-dioxide of 2H-1,2,4-benzothiadiazine which is substituted at position 3 by a methyl group and at position 7 by chlorine. A peripheral vasodilator, it increases the concentration of glucose in the plasma and inhibits the secretion of insulin by the beta- cells of the pancreas. It is used orally in the management of intractable hypoglycaemia and intravenously in the management of hypertensive emergencies.	2.03	1	0	benzothiadiazine; organochlorine compound; sulfone	antihypertensive agent; beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; diuretic; K-ATP channel agonist; sodium channel blocker; sympathomimetic agent; vasodilator agent
dibutyl phthalate Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.	2.48	2	0	diester; phthalate ester	EC 3.2.1.20 (alpha-glucosidase) inhibitor; environmental contaminant; metabolite; plasticiser; teratogenic agent
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	11.5	39	9	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
dichlorodiphenyl dichloroethylene Dichlorodiphenyl Dichloroethylene: An organochlorine pesticide, it is the ethylene metabolite of DDT.	2.13	1	0	chlorophenylethylene; monochlorobenzenes	human xenobiotic metabolite; persistent organic pollutant
ddt 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethane: structure in first source	2.55	2	0	benzenoid aromatic compound; chlorophenylethane; monochlorobenzenes; organochlorine insecticide	bridged diphenyl acaricide; carcinogenic agent; endocrine disruptor; persistent organic pollutant
dichlorophen Dichlorophen: Nontoxic laxative vermicide effective for taenia infestation. It tends to produce colic and nausea. It is also used as a veterinary fungicide, anthelmintic, and antiprotozoan. (From Merck, 11th ed.)	2.17	1	0	bridged diphenyl fungicide; diarylmethane
diethyl pyrocarbonate Diethyl Pyrocarbonate: Preservative for wines, soft drinks, and fruit juices and a gentle esterifying agent.. diethyl pyrocarbonate : The diethyl ester of dicarbonic acid.	2.08	1	0	acyclic carboxylic anhydride
diethylcarbamazine Diethylcarbamazine: An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.	2.06	1	0	N-carbamoylpiperazine; N-methylpiperazine
pentetic acid Pentetic Acid: An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.	2.05	1	0	pentacarboxylic acid	copper chelator
diflunisal Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.. diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position.	3.27	6	0	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug
dimethoate Dimethoate: An organothiophosphorus cholinesterase inhibitor that is used as a systemic and contact insecticide.. dimethoate : A monocarboxylic acid amide that is N-methylacetamide in which one of the hydrogens of the methyl group attached to the carbonyl moiety is replaced by a (dimethoxyphosphorothioyl)sulfanediyl group.	2	1	0	monocarboxylic acid amide; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
diphenyleneiodonium diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor. dibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.	2.04	1	0	organic cation
benzophenone benzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.	3.44	7	0	benzophenones	photosensitizing agent; plant metabolite
dipyridamole Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.	2.43	2	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
disopyramide Disopyramide: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.. disopyramide : A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.	1.99	1	0	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug
disulfiram [no description available]	3.46	7	0	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor
diuron Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.	3.14	5	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
thiorphan Thiorphan: A potent inhibitor of membrane metalloendopeptidase (ENKEPHALINASE). Thiorphan potentiates morphine-induced ANALGESIA and attenuates naloxone-precipitated withdrawal symptoms.	2.1	1	0	N-acyl-amino acid
domperidone Domperidone: A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.. domperidone : 1-[3-(Piperidin-1-yl)propyl]-1,3-dihydro-2H-benzimidazol-2-one in which the 4-position of the piperidine ring is substituted by a 5-chloro-1,3-dihydro-2H-benzimidazol-2-on-1-yl group. A dopamine antagonist, it is used as an antiemetic for the short-term treatment of nausea and vomiting, and to control gastrointestinal effects of dopaminergic drugs given in the management of parkinsonism. The free base is used in oral suspensions, while the maleate salt is used in tablet preparations.	1.97	1	0	benzimidazoles; heteroarylpiperidine	antiemetic; dopaminergic antagonist
donepezil Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.	2.03	1	0	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
doxazosin Doxazosin: A prazosin-related compound that is a selective alpha-1-adrenergic blocker.. doxazosin : A member of the class of quinazolines that is quinazoline substituted by an amino group at position 4, methoxy groups at positions 6 and 7 and a piperazin-1-yl group at position 2 which in turn is substituted by a 2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl group at position 4. An antihypertensive agent, it is used in the treatment of high blood pressure.	2.51	2	0	aromatic amine; benzodioxine; monocarboxylic acid amide; N-acylpiperazine; N-arylpiperazine; quinazolines	alpha-adrenergic antagonist; antihyperplasia drug; antihypertensive agent; antineoplastic agent; vasodilator agent
doxepin Doxepin: A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.. doxepin : A dibenzooxepine that is 6,11-dihydrodibenzo[b,e]oxepine substituted by a 3-(dimethylamino)propylidene group at position 11. It is used as an antidepressant drug.	2.96	4	0	dibenzooxepine; tertiary amino compound	antidepressant
doxylamine Doxylamine: Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.	2.02	1	0	pyridines; tertiary amine	anti-allergic agent; antiemetic; antitussive; cholinergic antagonist; H1-receptor antagonist; histamine antagonist; sedative
e 4031 E 4031: class III anti-arrhythmia agent; structure given in UD	2.03	1	0	sulfonamide
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	2.08	1	0	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
eburnamonine [no description available]	1.97	1	0	alkaloid
econazole Econazole: An imidazole derivative that is commonly used as a topical antifungal agent.. econazole : A racemate composed of equimolar amounts of (R)- and (S)-econazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections.. 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 4-chlorobenzyl group.	3.54	8	0	dichlorobenzene; ether; imidazoles; monochlorobenzenes
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.08	1	0	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
emodin Emodin: Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies.. emodin : A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs.	2.05	1	0	trihydroxyanthraquinone	antineoplastic agent; laxative; plant metabolite; tyrosine kinase inhibitor
enoxacin Enoxacin: A broad-spectrum 6-fluoronaphthyridinone antibacterial agent that is structurally related to NALIDIXIC ACID.. enoxacin : A 1,8-naphthyridine derivative that is 1,4-dihydro-1,8-naphthyridine with an ethyl group at the 1 position, a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a piperazin-1-yl group at the 7 position. An antibacterial, it is used in the treatment of urinary-tract infections and gonorrhoea.	2.02	1	0	1,8-naphthyridine derivative; amino acid; fluoroquinolone antibiotic; monocarboxylic acid; N-arylpiperazine; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor
erythrosine Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.	4.26	17	0
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.03	1	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
profenamine profenamine: was heading 1972-94 (see under PHENOTHIAZINES 1972-90); use PHENOTHIAZINES to search ETHOPROPAZINE 1972-94. profenamine : A member of the class of phenothiazines that is phenothiazine in which the hydrogen attached to the nitrogen is substituted by a 2-(diethylamino)propyl group. An antimuscarinic, it is used as the hydrochloride for the symptomatic treatment of Parkinson's disease.	2.03	1	0	phenothiazines; tertiary amino compound	adrenergic antagonist; antidyskinesia agent; antiparkinson drug; histamine antagonist; muscarinic antagonist
ethoxyquin Ethoxyquin: Antioxidant; also a post-harvest dip to prevent scald on apples and pears.. ethoxyquin : A quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6.	3.14	1	0	aromatic ether; quinolines	antifungal agrochemical; food antioxidant; genotoxin; geroprotector; herbicide; Hsp90 inhibitor; neuroprotective agent; UDP-glucuronosyltransferase activator
ethoxzolamide Ethoxzolamide: A carbonic anhydrase inhibitor used as diuretic and in glaucoma. It may cause hypokalemia.. ethoxzolamide : A sulfonamide that is 1,3-benzothiazole-2-sulfonamide which is substituted by an ethoxy group at position 6. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic.	1.98	1	0	aromatic ether; benzothiazoles; sulfonamide	antiglaucoma drug; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
eicosapentaenoic acid ethyl ester [no description available]	2.17	1	0
ethylenediamine ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.	3.77	10	0	alkane-alpha,omega-diamine	GABA agonist
etidronate Etidronic Acid: A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover.. etidronic acid : A 1,1-bis(phosphonic acid) that is (ethane-1,1-diyl)bis(phosphonic acid) having a hydroxy substituent at the 1-position. It inhibits the formation, growth, and dissolution of hydroxyapatite crystals by chemisorption to calcium phosphate surfaces.	2.05	1	0	1,1-bis(phosphonic acid)	antineoplastic agent; bone density conservation agent; chelator
etodolac Etodolac: A non-steroidal anti-inflammatory agent and cyclooxygenase-2 (COX-2) inhibitor with potent analgesic and anti-arthritic properties. It has been shown to be effective in the treatment of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; ANKYLOSING SPONDYLITIS; and in the alleviation of postoperative pain (PAIN, POSTOPERATIVE).. etodolac : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active.	4.38	6	0	monocarboxylic acid; organic heterotricyclic compound	antipyretic; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
famotidine Famotidine: A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion.	3.49	7	0	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
carbonyl cyanide p-trifluoromethoxyphenylhydrazone Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone: A proton ionophore that is commonly used as an uncoupling agent in biochemical studies.. carbonyl cyanide p-trifluoromethoxyphenylhydrazone : A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.	2.07	1	0	aromatic ether; hydrazone; nitrile; organofluorine compound	ATP synthase inhibitor; geroprotector; ionophore
felbamate Felbamate: A PEGylated phenylcarbamate derivative that acts as an antagonist of NMDA RECEPTORS. It is used as an anticonvulsant, primarily for the treatment of SEIZURES in severe refractory EPILEPSY.. felbamate : The bis(carbamate ester) of 2-phenylpropane-1,3-diol. An anticonvulsant, it is used in the treatment of epilepsy.	1.98	1	0	carbamate ester	anticonvulsant; neuroprotective agent
4-biphenylylacetic acid biphenyl-4-ylacetic acid : A monocarboxylic acid in which one of the alpha-hydrogens is substituted by a biphenyl-4-yl group. An active metabolite of fenbufen, it is used as a topical medicine to treat muscle inflammation and arthritis.	1.99	1	0	biphenyls; monocarboxylic acid	non-steroidal anti-inflammatory drug
felodipine Felodipine: A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.. felodipine : The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris.	2.07	1	0	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent
fenbendazole Fenbendazole: Antinematodal benzimidazole used in veterinary medicine.. fenbendazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections.	2.05	1	0	aryl sulfide; benzimidazoles; carbamate ester	antinematodal drug
fenbufen fenbufen: structure; RN given refers to parent cpd	2.49	2	0	4-oxo monocarboxylic acid; biphenyls	non-steroidal anti-inflammatory drug
fenofibrate Pharmavit: a polyvitamin product, comprising vitamins A, D2, B1, B2, B6, C, E, nicotinamide, & calcium pantothene; may be a promising agent for application to human populations exposed to carcinogenic and genetic hazards of ionizing radiation; RN from CHEMLINE	2.78	3	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
fenoldopam Fenoldopam: A dopamine D1 receptor agonist that is used as an antihypertensive agent. It lowers blood pressure through arteriolar vasodilation.	2.04	1	0	benzazepine	alpha-adrenergic agonist; antihypertensive agent; dopamine agonist; dopaminergic antagonist; vasodilator agent
fenoprofen Fenoprofen: A propionic acid derivative that is used as a non-steroidal anti-inflammatory agent.. fenoprofen : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.	4.52	5	1	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; non-narcotic analgesic; non-steroidal anti-inflammatory drug
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	3.28	6	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
fenthion Fenthion: Potent cholinesterase inhibitor used as an insecticide and acaricide.. fenthion : An organic thiophosphate that is O,O-dimethyl hydrogen phosphorothioate in which the hydrogen atom of the hydroxy group is replaced by a 3-methyl-4-(methylsulfanyl)phenyl group. It exhibits acaricidal and insecticidal activities.	2.63	2	0	organic thiophosphate	acaricide; agrochemical; avicide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; insecticide
fexofenadine fexofenadine: a second generation antihistamine; metabolite of the antihistaminic drug terfenadine; structure in first source; RN refers to HCl. fexofenadine : A piperidine-based anti-histamine compound.	2.75	3	0	piperidines; tertiary amine	anti-allergic agent; H1-receptor antagonist
fluconazole Fluconazole: Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.. fluconazole : A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.	3.48	6	0	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic
flucytosine Flucytosine: A fluorinated cytosine analog that is used as an antifungal agent.. flucytosine : An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections.	2.1	1	0	aminopyrimidine; nucleoside analogue; organofluorine compound; pyrimidine antifungal drug; pyrimidone	prodrug
flufenamic acid Flufenamic Acid: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16). flufenamic acid : An aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders.	3.13	5	0	aromatic amino acid; organofluorine compound	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
flunitrazepam Flunitrazepam: A benzodiazepine with pharmacologic actions similar to those of DIAZEPAM that can cause ANTEROGRADE AMNESIA. Some reports indicate that it is used as a date rape drug and suggest that it may precipitate violent behavior. The United States Government has banned the importation of this drug.. flunitrazepam : A 1,4-benzodiazepinone that is nitrazepam substituted by a methyl group at position 1 and by a fluoro group at position 2'. It is a potent hypnotic, sedative, and amnestic drug used to treat chronic insomnia.	2.07	1	0	1,4-benzodiazepinone; C-nitro compound; monofluorobenzenes	anxiolytic drug; GABAA receptor agonist; sedative
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	4.61	25	0	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	3.94	12	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
flurbiprofen Flurbiprofen: An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.. flurbiprofen : A monocarboxylic acid that is a 2-fluoro-[1,1'-biphenyl-4-yl] moiety linked to C-2 of propionic acid. A non-steroidal anti-inflammatory, analgesic and antipyretic, it is used as a pre-operative anti-miotic as well as orally for arthritis or dental pain.	4.59	25	0	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
flutamide Flutamide: An antiandrogen with about the same potency as cyproterone in rodent and canine species.	2.97	4	0	(trifluoromethyl)benzenes; monocarboxylic acid amide	androgen antagonist; antineoplastic agent
furazolidone Furazolidone: A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone acts by gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514). furazolidone : A member of the class of oxazolidines that is 1,3-oxazolidin-2-one in which the hydrogen attached to the nitrogen is replaced by an N-{[(5-nitro-2-furyl)methylene]amino} group. It has antibacterial and antiprotozoal properties, and is used in the treatment of giardiasis and cholera.	2.66	2	0	nitrofuran antibiotic; oxazolidines	antibacterial drug; antiinfective agent; antitrichomonal drug; EC 1.4.3.4 (monoamine oxidase) inhibitor
furosemide Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.	3.72	10	0	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic
gabapentin Gabapentin: A cyclohexane-gamma-aminobutyric acid derivative that is used for the treatment of PARTIAL SEIZURES; NEURALGIA; and RESTLESS LEGS SYNDROME.. gabapentin : A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.	2.41	2	0	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic
gemfibrozil [no description available]	3.46	7	0	aromatic ether	antilipemic drug
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	3.14	5	0
2,5-dihydroxybenzoic acid 2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.	2	1	0	dihydroxybenzoic acid	EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; fungal metabolite; human metabolite; MALDI matrix material; mouse metabolite
gliclazide Gliclazide: An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.	3.54	8	0	N-sulfonylurea	hypoglycemic agent; insulin secretagogue; radical scavenger
glimepiride glimepiride: structure given in first source	2.72	3	0	sulfonamide
glipizide Glipizide: An oral hypoglycemic agent which is rapidly absorbed and completely metabolized.. glipizide : An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.	2.96	4	0	aromatic amide; monocarboxylic acid amide; N-sulfonylurea; pyrazines	EC 2.7.1.33 (pantothenate kinase) inhibitor; hypoglycemic agent; insulin secretagogue
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	3.14	5	0	dialdehyde	cross-linking reagent; disinfectant; fixative
glutethimide Glutethimide: A hypnotic and sedative. Its use has been largely superseded by other drugs.	2.42	2	0	piperidines
glyburide Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.	3.57	8	0	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent
go 6976 [no description available]	2.03	1	0	indolocarbazole; organic heterohexacyclic compound	EC 2.7.11.13 (protein kinase C) inhibitor
gossypol Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.	2.02	1	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	3.24	5	0	methoxybenzenes
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	3.73	10	0	carboxamidine; guanidines; one-carbon compound
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	4.75	11	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
hexobarbital Hexobarbital: A barbiturate that is effective as a hypnotic and sedative.. hexobarbital : A member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups.	2.44	2	0	barbiturates
beta-thujaplicin beta-thujaplicin: structure. beta-thujaplicin : A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities.	2.15	1	0	cyclic ketone; enol; monoterpenoid	antibacterial agent; antifungal agent; antineoplastic agent; antiplasmodial drug; plant metabolite
ethidium Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.	3.01	3	0	phenanthridines	fluorochrome; intercalator
hydralazine Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.. hydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.	2.13	1	0	azaarene; hydrazines; ortho-fused heteroarene; phthalazines	antihypertensive agent; vasodilator agent
hydrochlorothiazide Hydrochlorothiazide: A thiazide diuretic often considered the prototypical member of this class. It reduces the reabsorption of electrolytes from the renal tubules. This results in increased excretion of water and electrolytes, including sodium, potassium, chloride, and magnesium. It is used in the treatment of several disorders including edema, hypertension, diabetes insipidus, and hypoparathyroidism.. hydrochlorothiazide : A benzothiadiazine that is 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted by a chloro group at position 6 and a sulfonamide at 7. It is diuretic used for the treatment of hypertension and congestive heart failure.	3.41	7	0	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic
hydroflumethiazide Hydroflumethiazide: A thiazide diuretic with actions and uses similar to those of HYDROCHLOROTHIAZIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p822). hydroflumethiazide : A benzothiadiazine consisting of a 3,4-dihydro-HH-1,2,4-benzothiadiazine bicyclic system dioxygenated on sulfur and carrying trifluoromethyl and aminosulfonyl groups at positions 6 and 7 respectively. A diuretic with actions and uses similar to those of hydrochlorothiazide.	2.37	2	0	benzothiadiazine; thiazide	antihypertensive agent; diuretic
hydroxychloroquine Hydroxychloroquine: A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Hydroxychloroquine appears to concentrate in food vacuoles of affected protozoa. It inhibits plasmodial heme polymerase. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p970). hydroxychloroquine : An aminoquinoline that is chloroquine in which one of the N-ethyl groups is hydroxylated at position 2. An antimalarial with properties similar to chloroquine that acts against erythrocytic forms of malarial parasites, it is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions.	3.69	2	0	aminoquinoline; organochlorine compound; primary alcohol; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; dermatologic drug
hypericin [no description available]	2.87	3	0
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	5.44	58	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
lidocaine Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.	3.77	10	0	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic
idebenone [no description available]	2.13	1	0	1,4-benzoquinones; primary alcohol	antioxidant; ferroptosis inhibitor
imipramine Imipramine: The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.. imipramine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)propyl group at the nitrogen atom.	3.03	4	0	dibenzoazepine	adrenergic uptake inhibitor; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
indomethacin Indomethacin: A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.. indometacin : A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.	8.27	48	2	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic
indoprofen Indoprofen: A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p21). indoprofen : A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein.	2.05	1	0	gamma-lactam; isoindoles; monocarboxylic acid	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
iohexol Iohexol: An effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality.. iohexol : A benzenedicarboxamide compound having N-(2,3-dihydroxypropyl)carbamoyl groups at the 1- and 3-positions, iodo substituents at the 2-, 4- and 6-positions and an N-(2,3-dihydroxypropyl)acetamido group at the 5-position.	2.13	1	0	benzenedicarboxamide; organoiodine compound	environmental contaminant; radioopaque medium; xenobiotic
avapro Irbesartan: A spiro compound, biphenyl and tetrazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION, and in the treatment of kidney disease.. irbesartan : A biphenylyltetrazole that is an angiotensin II receptor antagonist used mainly for the treatment of hypertension.	3.22	5	0	azaspiro compound; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
1-methyl-3-isobutylxanthine 1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.	2.95	4	0	3-isobutyl-1-methylxanthine
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	2.04	1	0	organofluorine compound	inhalation anaesthetic
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.5	2	0	carbohydrazide	antitubercular agent; drug allergen
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	3.43	7	0	secondary alcohol; secondary fatty alcohol	protic solvent
isoproterenol Isoproterenol: Isopropyl analog of EPINEPHRINE; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant.. isoprenaline : A secondary amino compound that is noradrenaline in which one of the hydrogens attached to the nitrogen is replaced by an isopropyl group. A sympathomimetic acting almost exclusively on beta-adrenergic receptors, it is used (mainly as the hydrochloride salt) as a bronghodilator and heart stimulant for the management of a variety of cardiac disorders.	4.12	15	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
isradipine Isradipine: A potent antagonist of CALCIUM CHANNELS that is highly selective for VASCULAR SMOOTH MUSCLE. It is effective in the treatment of chronic stable angina pectoris, hypertension, and congestive cardiac failure.	2.73	3	0	benzoxadiazole; dihydropyridine; isopropyl ester; methyl ester
juglone juglone: structure. juglone : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogen at position 5 has been replaced by a hydroxy group. A plant-derived 1,4-naphthoquinone with confirmed antibacterial and antitumor activities.	2.03	1	0	hydroxy-1,4-naphthoquinone	geroprotector; herbicide; reactive oxygen species generator
ketamine Ketamine: A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.. ketamine : A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.	4.78	11	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.	4.01	13	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	5.9	31	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
ketorolac Ketorolac: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed). ketorolac : A racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.. 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid : A member of the class of pyrrolizines that is 2,3-dihydro-1H-pyrrolizine which is substituted at positions 1 and 5 by carboxy and benzoyl groups, respectively.	4.11	3	1	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
khellin Khellin: A vasodilator that also has bronchodilatory action. It has been employed in the treatment of angina pectoris, in the treatment of asthma, and in conjunction with ultraviolet light A, has been tried in the treatment of vitiligo. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1024). khellin : A furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator.	2.07	1	0	furanochromone; organic heterotricyclic compound; oxacycle	anti-asthmatic agent; bronchodilator agent; cardiovascular drug; vasodilator agent
kojic acid [no description available]	2.08	1	0	4-pyranones; enol; primary alcohol	Aspergillus metabolite; EC 1.10.3.1 (catechol oxidase) inhibitor; EC 1.10.3.2 (laccase) inhibitor; EC 1.13.11.24 (quercetin 2,3-dioxygenase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; EC 1.4.3.3 (D-amino-acid oxidase) inhibitor; NF-kappaB inhibitor; skin lightening agent
kynurenic acid Kynurenic Acid: A broad-spectrum excitatory amino acid antagonist used as a research tool.. kynurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by a hydroxy group at C-4.	2.73	3	0	monohydroxyquinoline; quinolinemonocarboxylic acid	G-protein-coupled receptor agonist; human metabolite; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist; Saccharomyces cerevisiae metabolite
3-phenyllactic acid 3-phenyllactic acid: alpha-hydroxy analog of phenylalanine; RN given refers to cpd without isomeric designation. 3-phenyllactic acid : A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a phenyl group.	2.4	2	0	2-hydroxy monocarboxylic acid	human metabolite
labetalol Labetalol: A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.. labetalol : A diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers ((R,S)-labetolol, (S,R)-labetolol, (S,S)-labetalol and (R,R)-labetalol). It is an adrenergic antagonist used to treat high blood pressure.. 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide : A member of the class of benzamides that is benzamide substituted by a hydroxy group at position 2 and by a 1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl group at position 5.	2.55	2	0	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound
lamotrigine [no description available]	2.71	3	0	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic
lansoprazole Lansoprazole: A 2,2,2-trifluoroethoxypyridyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS. Lansoprazole is a racemic mixture of (R)- and (S)-isomers.	2.77	3	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
beta-lapachone beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase. beta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.	3.15	5	0	benzochromenone; orthoquinones	anti-inflammatory agent; antineoplastic agent; plant metabolite
lauric acid dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.	2.08	1	0	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antibacterial agent; plant metabolite
lavendustin a lavendustin A: from Streptomyces griseolavendus; structure given in first source	3.35	2	0	aromatic amine
letrozole [no description available]	2.03	1	0	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
lithium hydroxide lithium hydroxide: used for tryptophan determinations in proteins & foods; RN given refers to cpd with MF of Li-OH	2.05	1	0	alkali metal hydroxide
lofepramine Lofepramine: A psychotropic IMIPRAMINE derivative that acts as a tricyclic antidepressant and possesses few anticholinergic properties. It is metabolized to DESIPRAMINE.	2.01	1	0	aromatic ketone; dibenzoazepine; monochlorobenzenes; tertiary amino compound	antidepressant
lomefloxacin lomefloxacin: structure given in first source. lomefloxacin : A fluoroquinolone antibiotic, used (generally as the hydrochloride salt) to treat bacterial infections including bronchitis and urinary tract infections. It is also used to prevent urinary tract infections prior to surgery.	2.44	2	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antimicrobial agent; antitubercular agent; photosensitizing agent
lomustine [no description available]	2.13	1	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
loratadine Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.. loratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.	2.99	4	0	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent.	2.95	4	0	benzodiazepine
losartan Losartan: An antagonist of ANGIOTENSIN TYPE 1 RECEPTOR with antihypertensive activity due to the reduced pressor effect of ANGIOTENSIN II.. losartan : A biphenylyltetrazole where a 1,1'-biphenyl group is attached at the 5-position and has an additional trisubstituted imidazol-1-ylmethyl group at the 4'-position	3.21	5	0	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist
loxapine Loxapine: An antipsychotic agent used in SCHIZOPHRENIA.	2	1	0	dibenzooxazepine	antipsychotic agent; dopaminergic antagonist
2-(4-morpholinyl)-8-phenyl-4h-1-benzopyran-4-one 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one: specific inhibitor of phosphatidylinositol 3-kinase; structure in first source	3.44	7	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	2.83	3	0	diester; ethyl ester; organic thiophosphate
edaravone [no description available]	2.48	2	0	pyrazolone	antioxidant; radical scavenger
mebendazole Mebendazole: A benzimidazole that acts by interfering with CARBOHYDRATE METABOLISM and inhibiting polymerization of MICROTUBULES.. mebendazole : A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.	3.54	8	0	aromatic ketone; benzimidazoles; carbamate ester	antinematodal drug; microtubule-destabilising agent; tubulin modulator
meclofenamic acid Meclofenamic Acid: A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis.. meclofenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoea (painful periods), osteoarthritis and rheumatoid arthritis.	1.99	1	0	aminobenzoic acid; organochlorine compound; secondary amino compound	analgesic; anticonvulsant; antineoplastic agent; antipyretic; antirheumatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
meclofenoxate Meclofenoxate: An ester of DIMETHYLAMINOETHANOL and para-chlorophenoxyacetic acid.	2.03	1	0	monocarboxylic acid
mefenamic acid Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.. mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.	2.75	3	0	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
memantine [no description available]	2.45	2	0	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
vitamin k 3 Vitamin K 3: A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.	2.01	1	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
meperidine Meperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.. pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.	1.96	1	0	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic
mephenytoin Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.	1.98	1	0	imidazolidine-2,4-dione	anticonvulsant
mepivacaine Mepivacaine: A local anesthetic that is chemically related to BUPIVACAINE but pharmacologically related to LIDOCAINE. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168). mepivacaine : A piperidinecarboxamide in which N-methylpipecolic acid and 2,6-dimethylaniline have combined to form the amide bond. It is used as a local amide-type anaesthetic.	2.4	2	0	piperidinecarboxamide	drug allergen; local anaesthetic
mesalamine Mesalamine: An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed). mesalamine : A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.	2.11	1	0	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug
metaproterenol Metaproterenol: A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM.. orciprenaline : A racemate composed of equimolar amounts of (R)- and (S)-orciprenaline. Used (as its sulfate salt) to relax the airway muscles and improve breathing for patients suffering from asthma or bronchitis.. 5-[1-hydroxy-2-(isopropanylamino)ethyl]benzene-1,3-diol : A member of the class of resorcinols bearing an additional 1-hydroxy-2-(isopropanylamino)ethyl substituent at position 5 of resorcinol itself.	2.92	4	0	aralkylamino compound; phenylethanolamines; resorcinols; secondary alcohol; secondary amino compound
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	3.17	5	0	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
methacrylic acid methacrylic acid: RN given refers to parent cpd. methacrylic acid : An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.	3.65	8	0	alpha,beta-unsaturated monocarboxylic acid
methadone Methadone: A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). methadone : A racemate comprising equimolar amounts of dextromethadone and levomethadone. It is a opioid analgesic which is used as a painkiller and as a substitute for heroin in the treatment of heroin addiction.. 6-(dimethylamino)-4,4-diphenylheptan-3-one : A ketone that is heptan-3-one substituted by a dimethylamino group at position 6 and two phenyl groups at position 4.	3.34	6	0	benzenes; diarylmethane; ketone; tertiary amino compound
methenamine Methenamine: An anti-infective agent most commonly used in the treatment of urinary tract infections. Its anti-infective action derives from the slow release of formaldehyde by hydrolysis at acidic pH. (From Martindale, The Extra Pharmacopoeia, 30th ed, p173). hexamethylenetetramine : A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.	2.76	3	0	polyazaalkane; polycyclic cage; tetramine	antibacterial drug
methocarbamol Methocarbamol: A centrally acting muscle relaxant whose mode of action has not been established. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1206). methocarbamol : A racemate comprising equimolar amounts of (R)- and (S)-methocarbamol. A centrally acting skeletal muscle relaxant, it is used as an adjunct in the short-term symptomatic treatment of painful muscle spasm. The (R)-enantiomer is more active than the (S)-enantiomer.. 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate : A carbamate ester that is glycerol in which one of the primary alcohol groups has been converted to its 2-methoxyphenyl ether while the other has been converted to the corresponding carbamate ester.	2.21	1	0	aromatic ether; carbamate ester; secondary alcohol
methoxsalen Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.	2.71	3	0	aromatic ether; psoralens	antineoplastic agent; cross-linking reagent; dermatologic drug; photosensitizing agent; plant metabolite
nocodazole [no description available]	2.72	3	0	aromatic ketone; benzimidazoles; carbamate ester; thiophenes	antimitotic; antineoplastic agent; microtubule-destabilising agent; tubulin modulator
methyl parathion Methyl Parathion: The methyl homolog of parathion. An effective, but highly toxic, organothiophosphate insecticide and cholinesterase inhibitor.. parathion-methyl : A C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4.	3.34	6	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; genotoxin
methyl salicylate methyl salicylate: used in over-the-counter liniments, ointments, lotions for relief of musculoskeletal aches and pains; has hemolytic effect on human & sheep erythrocytes; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5990. methyl salicylate : A benzoate ester that is the methyl ester of salicylic acid.	2.47	2	0	benzoate ester; methyl ester; salicylates	flavouring agent; insect attractant; metabolite
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	2.44	2	0	beta-amino acid ester; methyl ester; piperidines
metoclopramide Metoclopramide: A dopamine D2 antagonist that is used as an antiemetic.. metoclopramide : A member of the class of benzamides resulting from the formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with the primary amino group of N,N-diethylethane-1,2-diamine.	2.4	2	0	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic
metolachlor metolachlor: structure given in first source. metolachlor : A racemate that consists of equimolar amounts of (R)- and (S)-metolachlor.. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a (2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl) group at the nitrogen atom.	2.07	1	0	aromatic amide; benzenes; ether; organochlorine compound
metoprolol Metoprolol: A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.. metoprolol : A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.	3.68	9	0	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic
metronidazole Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.	3.55	8	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
mexiletine Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.	2.47	2	0	aromatic ether; primary amino compound	anti-arrhythmia drug
mianserin Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.	3.1	4	0	dibenzoazepine	adrenergic uptake inhibitor; alpha-adrenergic antagonist; antidepressant; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; H1-receptor antagonist; histamine agonist; sedative; serotonergic antagonist
miconazole Miconazole: An imidazole antifungal agent that is used topically and by intravenous infusion.. 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles that is 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanol in which the hydroxyl hydrogen is replaced by a 2,4-dichlorobenzyl group.. miconazole : A racemate composed of equimolar amounts of (R)- and (S)-miconazole. Used (as its nitrate salt) to treat skin infections such as athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.	3.83	11	0	dichlorobenzene; ether; imidazoles
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively.	3.47	7	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
midodrine Midodrine: An ethanolamine derivative that is an adrenergic alpha-1 agonist. It is used as a vasoconstrictor agent in the treatment of HYPOTENSION.. midodrine : An aromatic ether that is 1,4-dimethoxybenzene which is substituted at position 2 by a 2-(glycylamino)-1-hydroxyethyl group. A direct-acting sympathomimetic with selective alpha-adrenergic agonist activity, it is used (generally as its hydrochloride salt) as a peripheral vasoconstrictor in the treatment of certain hypotensive states. The main active moiety is its major metabolite, deglymidodrine.	2.08	1	0	amino acid amide; aromatic ether; secondary alcohol	alpha-adrenergic agonist; prodrug; sympathomimetic agent; vasoconstrictor agent
minoxidil Minoxidil: A potent direct-acting peripheral vasodilator (VASODILATOR AGENTS) that reduces peripheral resistance and produces a fall in BLOOD PRESSURE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371). minoxidil : A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.	2.48	2	0	dialkylarylamine; tertiary amino compound
mirtazapine Mirtazapine: A piperazinoazepine tetracyclic compound that enhances the release of NOREPINEPHRINE and SEROTONIN through blockage of presynaptic ALPHA-2 ADRENERGIC RECEPTORS. It also blocks both 5-HT2 and 5-HT3 serotonin receptors and is a potent HISTAMINE H1 RECEPTOR antagonist. It is used for the treatment of depression, and may also be useful for the treatment of anxiety disorders.	2.1	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist
mitotane Mitotane: A derivative of the insecticide DICHLORODIPHENYLDICHLOROETHANE that specifically inhibits cells of the adrenal cortex and their production of hormones. It is used to treat adrenocortical tumors and causes CNS damage, but no bone marrow depression.	2.55	2	0	diarylmethane
modafinil Modafinil: A benzhydryl acetamide compound, central nervous system stimulant, and CYP3A4 inducing agent that is used in the treatment of NARCOLEPSY and SLEEP WAKE DISORDERS.. modafinil : A racemate comprising equimolar amounts of armodafinil and (S)-modafinil. A central nervous system stimulant, it is used for the treatment of sleeping disorders such as narcolepsy, obstructive sleep apnoea, and shift-work sleep disorder. The optical enantiomers of modafinil have similar pharmacological actions in animals.. 2-[(diphenylmethyl)sulfinyl]acetamide : A sulfoxide that is dimethylsulfoxide in which two hydrogens attached to one of the methyl groups are replaced by phenyl groups, while one hydrogen attached to the other methyl group is replaced by a carbamoyl (aminocarbonyl) group.	2.46	2	0	monocarboxylic acid amide; sulfoxide
molsidomine Molsidomine: A morpholinyl sydnone imine ethyl ester, having a nitrogen in place of the keto oxygen. It acts as NITRIC OXIDE DONORS and is a vasodilator that has been used in ANGINA PECTORIS.. molsidomine : A member of the class of oxadiazoles that is 1,2,3-oxadiazole substituted by morpholin-4-yl and (ethoxycarbonyl)azanidyl groups at positions 3 and 5, respectively. It is used as a vasodilator drug for the treatment of myocardial ischemic syndrome and congestive heart failure.	2.69	3	0	ethyl ester; morpholines; oxadiazole; zwitterion	antioxidant; apoptosis inhibitor; cardioprotective agent; nitric oxide donor; vasodilator agent
monodansylcadaverine monodansylcadaverine: inhibits cross linkage of fibrin. monodansylcadaverine : A sulfonamide obtained by formal condensation of the sulfo group of 5-(dimethylamino)naphthalene-1-sulfonic acid with one of the amino groups of cadaverine.	4.26	5	0	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent
ethylmaleimide Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.	2.7	3	0	maleimides	anticoronaviral agent; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.1.1 (hexokinase) inhibitor
n-methylephedrine N-methylephedrine: RN given refers to parent cpd	2.46	2	0	amphetamines
apnea Apnea: A transient absence of spontaneous respiration.	2.06	1	0	purine nucleoside
nefopam Nefopam: Non-narcotic analgesic chemically similar to ORPHENADRINE. Its mechanism of action is unclear. It is used for the relief of acute and chronic pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p26). nefopam : A racemate comprising equal amounts of (R)- and (S)-nefopam. The hydrochloride is a centrally acting non-opiate analgesic commonly used for the treatment of moderate to severe pain.. 5-methyl-1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocine : A member of the class of benzoxazocines that is 3,4,5,6-tetrahydro-1H-2,5-benzoxazocine substituted by phenyl and methyl groups at positions 1 and 5 respectively.	2.11	1	0	benzoxazocine; tertiary amino compound
neostigmine Neostigmine: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.. neostigmine : A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.	2.06	1	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
nicardipine Nicardipine: A potent calcium channel blockader with marked vasodilator action. It has antihypertensive properties and is effective in the treatment of angina and coronary spasms without showing cardiodepressant effects. It has also been used in the treatment of asthma and enhances the action of specific antineoplastic agents.. nicardipine : A racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension.. 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.	3.27	6	0	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound
niclosamide Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.	2.31	1	0	benzamides; C-nitro compound; monochlorobenzenes; salicylanilides; secondary carboxamide	anthelminthic drug; anticoronaviral agent; antiparasitic agent; apoptosis inducer; molluscicide; piscicide; STAT3 inhibitor
nifedipine Nifedipine: A potent vasodilator agent with calcium antagonistic action. It is a useful anti-anginal agent that also lowers blood pressure.	3.95	13	0	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent
niflumic acid Niflumic Acid: An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis.	2.06	1	0	aromatic carboxylic acid; pyridines
nimesulide nimesulide: structure. nimesulide : An aromatic ether having phenyl and 2-methylsulfonamido-5-nitrophenyl as the two aryl groups.	6.03	10	3	aromatic ether; C-nitro compound; sulfonamide	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
nimodipine Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.. nimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.	3.3	6	0	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent
nipecotic acid nipecotic acid: RN given refers to cpd without isomeric designation. nipecotic acid : A piperidinemonocarboxylic acid that is piperidine in which one of the hydrogens at position 3 is substituted by a carboxylic acid group.	2.02	1	0	beta-amino acid; piperidinemonocarboxylic acid
nisoldipine Nisoldipine: A dihydropyridine calcium channel antagonist that acts as a potent arterial vasodilator and antihypertensive agent. It is also effective in patients with cardiac failure and angina.. nisoldipine : A racemate consisting of equimolar amounts of (R)- and (S)-nisoldipine. A calcium channel blocker, it is used in the treatment of hypertension and angina pectoris.. methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a methoxycarbonyl group at position 3, an o-nitrophenyl group at position 4, and an isobutoxycarbonyl group at position 5. The racemate, a calcium channel blocker, is used in the treatment of hypertension and angina pectoris.	2.05	1	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; methyl ester
nitrendipine Nitrendipine: A calcium channel blocker with marked vasodilator action. It is an effective antihypertensive agent and differs from other calcium channel blockers in that it does not reduce glomerular filtration rate and is mildly natriuretic, rather than sodium retentive.. nitrendipine : A dihydropyridine that is 1,4-dihydropyridine substituted by methyl groups at positions 2 and 6, a 3-nitrophenyl group at position 4, a ethoxycarbonyl group at position 3 and a methoxycarbonyl group at position 5. It is a calcium-channel blocker used in the treatment of hypertension.	2.42	2	0	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; ethyl ester; methyl ester	antihypertensive agent; calcium channel blocker; geroprotector; vasodilator agent
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	2.68	3	0	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
masoprocol nordihydroguaretic acid: antioxidant compound found in the creosote bush (Larrea tridentata)	2.03	1	0	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite
norfenefrine norfenefrine: RN given refers to cpd without isomeric designation; structure	2.44	2	0	phenols
norfloxacin Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.	4.29	17	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic
norfluoxetine norfluoxetine: metabolite of fluoxetine; RN given refers to parent cpd without isomeric designation	2	1	0	(trifluoromethyl)benzenes
nortriptyline Nortriptyline: A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions.. nortriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline.	2.98	3	0	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite
5-nitro-2-(3-phenylpropylamino)benzoic acid 5-nitro-2-(3-phenylpropylamino)benzoic acid: structure given in first source; chloride channel antagonist	2.46	2	0	nitrobenzoic acid
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.44	2	0	phenylethanolamines; tyramines	neurotransmitter
ofloxacin Ofloxacin: A synthetic fluoroquinolone antibacterial agent that inhibits the supercoiling activity of bacterial DNA GYRASE, halting DNA REPLICATION.. 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid : An oxazinoquinoline that is 2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one substituted by methyl, carboxy, fluoro, and 4-methylpiperazin-1-yl groups at positions 3, 6, 9, and 10, respectively.. ofloxacin : A racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.	3.77	10	0	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline
omeprazole Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.	3.65	9	0	aromatic ether; benzimidazoles; pyridines; sulfoxide
ondansetron Ondansetron: A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties.	2.96	4	0	carbazoles
oxaprozin Oxaprozin: An oxazole-propionic acid derivative, cyclooxygenase inhibitor, and non-steroidal anti-inflammatory drug that is used in the treatment of pain and inflammation associated with of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; and ARTHRITIS, JUVENILE.. oxaprozin : A monocarboxylic acid that is a propionic acid derivative having a 4,5-diphenyl-1,3-oxazol-2-yl substituent at position 3. It is non-steroidal anti-inflammatory drug commonly used to relieve the pain and inflammatory responses associated with osteoarthritis and rheumatoid arthritis.	3.21	5	0	1,3-oxazoles; monocarboxylic acid	analgesic; non-steroidal anti-inflammatory drug
oxazepam Oxazepam: A benzodiazepine used in the treatment of anxiety, alcohol withdrawal, and insomnia.. oxazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a hydroxy group at position 3 and phenyl group at position 5.	2.74	3	0	1,4-benzodiazepinone; organochlorine compound	anxiolytic drug; environmental contaminant; xenobiotic
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	2.21	1	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
oxotremorine Oxotremorine: A non-hydrolyzed muscarinic agonist used as a research tool.	2.04	1	0	N-alkylpyrrolidine
oxybenzone oxybenzone : A hydroxybenzophenone that is benzophenone which is substituted at the 2- and 4-positions of one of the benzene rings by hydroxy and methoxy groups respectively.	2.74	3	0	hydroxybenzophenone; monomethoxybenzene	dermatologic drug; environmental contaminant; protective agent; ultraviolet filter; xenobiotic
oxybutynin oxybutynin: RN given refers to parent cpd. oxybutynin : A racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder.	3.05	4	0	acetylenic compound; carboxylic ester; racemate; tertiary alcohol; tertiary amino compound	antispasmodic drug; calcium channel blocker; local anaesthetic; muscarinic antagonist; muscle relaxant; parasympatholytic
oxyphencyclimine oxyphencyclimine: minor descriptor (65-85); on-line & Index Medicus search PYRIMIDINES (65-85); RN given refers to parent cpd without isomeric designation	1.99	1	0	monocarboxylic acid
aminosalicylic acid Aminosalicylic Acid: An antitubercular agent often administered in association with ISONIAZID. The sodium salt of the drug is better tolerated than the free acid.. 4-aminosalicylic acid : An aminobenzoic acid that is salicylic acid substituted by an amino group at position 4.	2.08	1	0	aminobenzoic acid; phenols	antitubercular agent
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	2.45	2	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	2.47	2	0	phenylalanine derivative
pantoprazole Pantoprazole: 2-pyridinylmethylsulfinylbenzimidazole proton pump inhibitor that is used in the treatment of GASTROESOPHAGEAL REFLUX and PEPTIC ULCER.. pantoprazole : A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a difluoromethoxy group at position 5 and a [(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl group at position 2.	2.76	3	0	aromatic ether; benzimidazoles; organofluorine compound; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; environmental contaminant; xenobiotic
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	2.39	2	0	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
4-chlorophenol 4-chlorophenol: used as a root canal irrigant. 4-chlorophenol : A monochlorophenol substituted at the pare position by a chlorine atom.	2.11	1	0	monochlorophenol
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	2.39	2	0	aromatic amine
patulin Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.	2.41	1	0	furopyran; gamma-lactone; lactol	antimicrobial agent; Aspergillus metabolite; carcinogenic agent; mutagen; mycotoxin; Penicillium metabolite
pd 98059 2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one: inhibits MAP kinase kinase (MEK) activity, p42 MAPK and p44 MAPK; structure in first source. 2-(2-amino-3-methoxyphenyl)chromen-4-one : A member of the class of monomethoxyflavones that is 3'-methoxyflavone bearing an additional amino substituent at position 2'.	2.72	3	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
pentamidine Pentamidine: Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.. pentamidine : A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease.	2.07	1	0	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.73	3	0	barbiturates	GABAA receptor agonist
perphenazine Perphenazine: An antipsychotic phenothiazine derivative with actions and uses similar to those of CHLORPROMAZINE.. perphenazine : A phenothiazine derivative in which the phenothiazine tricycle carries a chloro substituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at N-10.	2.98	4	0	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; organochlorine compound; phenothiazines	antiemetic; dopaminergic antagonist; phenothiazine antipsychotic drug
phenacetin Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione	2.71	3	0	acetamides; aromatic ether	cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug
phenindione Phenindione: An indandione that has been used as an anticoagulant. Phenindione has actions similar to WARFARIN, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)	1.98	1	0	aromatic ketone; beta-diketone	anticoagulant
pheniramine Pheniramine: One of the HISTAMINE H1 ANTAGONISTS with little sedative action. It is used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus.	3.04	4	0	pyridines; tertiary amino compound
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.67	3	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	3.72	10	0	phenols
phenolsulfonphthalein Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.	2.7	3	0	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator
phenoxybenzamine Phenoxybenzamine: An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.	2.42	2	0	aromatic amine
oxophenylarsine oxophenylarsine: inhibits protein-tyrosine-phosphatase. phenylarsine oxide : An arsine oxide derived from phenylarsine.	2.96	4	0	arsine oxides	antineoplastic agent; apoptosis inducer; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
phenylbutazone Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.	2.01	1	0	pyrazolidines	antirheumatic drug; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
phenylmethylsulfonyl fluoride Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.	2.13	1	0	acyl fluoride	serine proteinase inhibitor
phloretin [no description available]	2.94	4	0	dihydrochalcones	antineoplastic agent; plant metabolite
o-phthalaldehyde o-Phthalaldehyde: A reagent that forms fluorescent conjugation products with primary amines. It is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.. phthalaldehyde : A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.	2.76	3	0	benzaldehydes; dialdehyde	epitope
pinacidil Pinacidil: A guanidine that opens POTASSIUM CHANNELS producing direct peripheral vasodilatation of the ARTERIOLES. It reduces BLOOD PRESSURE and peripheral resistance and produces fluid retention. (Martindale The Extra Pharmacopoeia, 31st ed)	2.05	1	0	pyridines
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	2.01	1	0	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
pipemidic acid Pipemidic Acid: Antimicrobial against Gram negative and some Gram positive bacteria. It is protein bound and concentrated in bile and urine and used for gastrointestinal, biliary, and urinary infections.. pipemidic acid : A pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid substituted at position 2 by a piperazin-1-yl group and at position 8 by an ethyl group. A synthetic broad-spectrum antibacterial, it is used for treatment of gastrointestinal, biliary, and urinary infections.	2.53	2	0	amino acid; monocarboxylic acid; N-arylpiperazine; pyridopyrimidine; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor
pirenzepine Pirenzepine: An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.	2.46	2	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
piretanide piretanide: potent inhibitor of chloride transport; structure	1.97	1	0	aromatic ether
piribedil Piribedil: A dopamine D2 agonist. It is used in the treatment of parkinson disease, particularly for alleviation of tremor. It has also been used for circulatory disorders and in other applications as a D2 agonist.	2.03	1	0	N-arylpiperazine
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	3.51	8	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.98	4	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
ag 1879 3-(4-chlorophenyl)-1-(1,1-dimethylethyl)-1H-pyrazolo(3,4-d)pyrimidin-4-amine: Fyn kinase inhibitor	3.29	6	0	aromatic amine; monochlorobenzenes; pyrazolopyrimidine	beta-adrenergic antagonist; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector
ono 1078 pranlukast: SRS-A antagonist; leukotriene D4 receptor antagonist	2.03	1	0	chromones
pyranoprofen pyranoprofen: RN given refers to unlabled parent cpd; structure given in first source	2.52	2	0	pyridochromene
praziquantel azinox: Russian drug	3.83	11	0	isoquinolines
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.75	3	0	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
prilocaine Prilocaine: A local anesthetic that is similar pharmacologically to LIDOCAINE. Currently, it is used most often for infiltration anesthesia in dentistry.. prilocaine : An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.	3.11	5	0	amino acid amide; monocarboxylic acid amide	anticonvulsant; local anaesthetic
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	2.75	3	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	2.76	3	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	3.03	4	0	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
procaine Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.	2.7	3	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
promazine Promazine: A phenothiazine with actions similar to CHLORPROMAZINE but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic.. promazine : A phenothiazine deriative in which the phenothiazine tricycle has a 3-(dimethylaminopropyl) group at the N-10 position.	2.07	1	0	phenothiazines; tertiary amine	antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; muscarinic antagonist; phenothiazine antipsychotic drug; serotonergic antagonist
promethazine Promethazine: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals.. promethazine : A tertiary amine that is a substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropan-2-amine moiety.	3.44	7	0	phenothiazines; tertiary amine	anti-allergic agent; anticoronaviral agent; antiemetic; antipruritic drug; H1-receptor antagonist; local anaesthetic; sedative
propafenone Propafenone: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.. propafenone : An aromatic ketone that is 3-(propylamino)propane-1,2-diol in which the hydrogen of the primary hydroxy group is replaced by a 2-(3-phenylpropanoyl)phenyl group. It is a class 1C antiarrhythmic drug with local anesthetic effects, and is used as the hydrochloride salt in the management of supraventricular and ventricular arrhythmias.	2.08	1	0	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug
propanil Propanil: A chlorinated anilide that is used as an herbicide.. propanil : An anilide resulting from the formal condensation of the carboxy group of propanoic acid with the amino group of 3,4-dichloroaniline. It is a herbicide used for the treatment of numerous grasses and broad-leaved weeds in rice, potatoes, and wheat.	2.6	1	0	anilide; dichlorobenzene	herbicide
proxymetacaine proxymetacaine: RN given refers to parent cpd; structure	2.45	2	0	benzoate ester
propidium Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.	3.3	6	0	phenanthridines; quaternary ammonium ion	fluorochrome; intercalator
propofol Propofol: An intravenous anesthetic agent which has the advantage of a very rapid onset after infusion or bolus injection plus a very short recovery period of a couple of minutes. (From Smith and Reynard, Textbook of Pharmacology, 1992, 1st ed, p206). Propofol has been used as ANTICONVULSANTS and ANTIEMETICS.. propofol : A phenol resulting from the formal substitution of the hydrogen at the 2 position of 1,3-diisopropylbenzene by a hydroxy group.	5.37	13	1	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	4.9	34	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
pyrimethamine Maloprim: contains above 2 cpds	2.03	1	0	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
rabeprazole Rabeprazole: A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.	1.99	1	0	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor
resorcinol resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.	2.6	1	0	benzenediol; phenolic donor; resorcinols	erythropoietin inhibitor; sensitiser
riluzole Riluzole: A glutamate antagonist (RECEPTORS, GLUTAMATE) used as an anticonvulsant (ANTICONVULSANTS) and to prolong the survival of patients with AMYOTROPHIC LATERAL SCLEROSIS.	3.73	3	0	benzothiazoles
rimantadine Rimantadine: An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.	3.2	5	0	alkylamine
risperidone Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.	3.61	8	0	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist
rofecoxib [no description available]	2.71	3	0	butenolide; sulfone	analgesic; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
ropinirole [no description available]	2.15	1	0	indolones; tertiary amine	antidyskinesia agent; antiparkinson drug; central nervous system drug; dopamine agonist
roxatidine acetate roxatidine acetate: structure given in first source	2.44	2	0	piperidines
saccharin Saccharin: Flavoring agent and non-nutritive sweetener.. saccharin : A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position. It is used as an artificial sweetening agent.	2.51	2	0	1,2-benzisothiazole; N-sulfonylcarboxamide	environmental contaminant; sweetening agent; xenobiotic
sarpogrelate sarpogrelate: structure given in first source	2.05	1	0	hemisuccinate; stilbenoid
sb 202190 4-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinase	2.11	1	0	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
sebacic acid sebacic acid : An alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.	2.48	2	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	human metabolite; plant metabolite
sevoflurane Sevoflurane: A non-explosive inhalation anesthetic used in the induction and maintenance of general anesthesia. It does not cause respiratory irritation and may also prevent PLATELET AGGREGATION.. sevoflurane : An ether compound having fluoromethyl and 1,1,1,3,3,3-hexafluoroisopropyl as the two alkyl groups.	2.11	1	0	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor
sibutramine sibutramine: serotonin and norepinephrine transporter inhibitor; Meridia is tradename for sibutramine hydrochloride	3.01	4	0	organochlorine compound; tertiary amino compound	anti-obesity agent; serotonin uptake inhibitor
sulfadiazine Sulfadiazine: One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.. sulfadiazine : A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.. diazine : The parent structure of the diazines.	3.01	4	0	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sodium fluoride [no description available]	1.99	1	0	fluoride salt	mutagen
risedronic acid Risedronic Acid: A pyridine and diphosphonic acid derivative that acts as a CALCIUM CHANNEL BLOCKER and inhibits BONE RESORPTION.	2.05	1	0	pyridines
sotalol Sotalol: An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias.. sotalol : A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.	3.01	4	0	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	3.11	5	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	3	4	0	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
sulconazole sulconazole: RN given refers to cpd with unspecified isomeric designation; structure given in first source. sulconazole : A racemate comprising equimolar amounts of (R)- and (S)-sulconazole. An antifungal agent with activity against Candida species, it is used (generally as the nitrate salt) for the topical treatment of fungal skin infections.. 1-{2-[(4-chlorobenzyl)sulfanyl]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole : A member of the class of imidazoles that is 1-ethyl-1H-imidazole in which one of the hydrogens of the methyl group is replaced by a (4-chlorobenzyl)sulfanediyl group while a second is replaced by a 2,4-dichlorophenyl group.	2.47	2	0	dichlorobenzene; imidazoles; monochlorobenzenes; organic sulfide
sulfadimethoxine Sulfadimethoxine: A sulfanilamide that is used as an anti-infective agent.. sulfadimethoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	2.1	1	0	aromatic ether; pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; drug allergen; environmental contaminant; xenobiotic
sulfaguanidine Sulfaguanidine: A sulfanilamide antimicrobial agent that is used to treat enteric infections.. sulfaguanidine : A sulfonamide incorporating a guanidine moiety used to block the synthesis of folic acid; mostly used in veterinary medicine	2.03	1	0	sulfonamide antibiotic	antiinfective agent
sulfamerazine [no description available]	2.8	3	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen
sulfamethazine Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.	2.85	3	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antibacterial drug; antiinfective agent; antimicrobial agent; carcinogenic agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; ligand; xenobiotic
sulfamethizole Sulfamethizole: A sulfathiazole antibacterial agent.. sulfamethizole : A sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2.	2.39	2	0	sulfonamide antibiotic; sulfonamide; thiadiazoles	antiinfective agent; antimicrobial agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor
sulfamethoxazole Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.	3.42	7	0	isoxazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic
sulfamonomethoxine Sulfamonomethoxine: Long acting sulfonamide antibacterial agent.	2.02	1	0	benzenes; sulfonamide
sulfanilamide [no description available]	2.41	1	0	substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial agent; drug allergen; EC 4.2.1.1 (carbonic anhydrase) inhibitor
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	3.04	4	0
sulfathiazole Sulfathiazole: A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine.. sulfathiazole : A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position.	2.01	1	0	1,3-thiazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic
sulfisomidine Sulfisomidine: A sulfanilamide antibacterial agent.. sulfisomidine : A sulfonamide consisting of pyrimidine having methyl substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.	2.1	1	0	pyrimidines; sulfonamide antibiotic; sulfonamide	antiinfective agent
sulfisoxazole Sulfisoxazole: A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms.. sulfisoxazole : A sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of gram-negative and gram-positive organisms.	2.45	2	0	isoxazoles; sulfonamide antibiotic; sulfonamide	antibacterial drug; drug allergen
sulfobromophthalein Sulfobromophthalein: A phenolphthalein that is used as a diagnostic aid in hepatic function determination.	2.07	1	0	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.21	1	0	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
sulpiride Sulpiride: A dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed). sulpiride : A member of the class of benzamides obtained from formal condensation between the carboxy group of 2-methoxy-5-sulfamoylbenzoic acid and the primary amino group of (1-ethylpyrrolidin-2-yl)methylamine.	2.75	3	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
sumatriptan Sumatriptan: A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of MIGRAINE DISORDERS.. sumatriptan : A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults.	2.17	1	0	sulfonamide; tryptamines	serotonergic agonist; vasoconstrictor agent
suprofen Suprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.. suprofen : An aromatic ketone that is thiophene substituted at C-2 by a 4-(1-carboxyethyl)benzoyl group.	2.72	3	0	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug
gatifloxacin Gatifloxacin: A fluoroquinolone antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used as an ophthalmic solution for the treatment of BACTERIAL CONJUNCTIVITIS.. gatifloxacin : A monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes.	2.03	1	0	N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antiinfective agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
tazarotene tazarotene: a topical acetylenic retinoid; a topical kerytolytic. tazarotene : The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.	2.21	1	0	acetylenic compound; ethyl ester; pyridines; retinoid; thiochromane	keratolytic drug; prodrug; teratogenic agent
tegafur [no description available]	1.97	1	0	organohalogen compound; pyrimidines
temozolomide [no description available]	2.66	2	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
terbutaline Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.	4.12	15	0	phenylethanolamines; resorcinols	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; hypoglycemic agent; sympathomimetic agent; tocolytic agent
terfenadine Terfenadine: A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.	3.53	8	0	diarylmethane
tetracaine Tetracaine: A potent local anesthetic of the ester type used for surface and spinal anesthesia.. tetracaine : A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.	2.1	1	0	benzoate ester; tertiary amino compound	local anaesthetic
tetrahydrozoline tetrahydrozoline: used as nasal decongestant; Visine is a form of eye drops; RN given refers to parent cpd; structure	1.99	1	0	carboxamidine; imidazolines	nasal decongestant; sympathomimetic agent
thalidomide Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.	3.74	10	0	phthalimides; piperidones
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	2.48	2	0	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
thiabendazole Tresaderm: dermatologic soln containing dexamethasone, thiabendazole & neomycin sulfate	2.72	3	0	1,3-thiazoles; benzimidazole fungicide; benzimidazoles	antifungal agrochemical; antinematodal drug
thioridazine Thioridazine: A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.. thioridazine : A phenothiazine derivative having a methylsulfanyl subsitituent at the 2-position and a (1-methylpiperidin-2-yl)ethyl] group at the N-10 position.	2.44	2	0	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist
thiram Thiram: A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.. thiram : An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.	2.6	1	0	organic disulfide	antibacterial drug; antifungal agrochemical; antiseptic drug
tiaprofenic acid tiaprofenic acid: RN given refers to parent cpd; structure. tiaprofenic acid : An aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group.	2.42	2	0	aromatic ketone; monocarboxylic acid; thiophenes	drug allergen; non-steroidal anti-inflammatory drug
ticlopidine Ticlopidine: An effective inhibitor of platelet aggregation commonly used in the placement of STENTS in CORONARY ARTERIES.. ticlopidine : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group.	5.63	3	2	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor
tioconazole tioconazole : A racemate comprising equimolar amounts of (R)- and (S)-tioconazole.. 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2.	1.98	1	0	dichlorobenzene; ether; imidazoles; thiophenes
tolbutamide Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.	3.61	9	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
tolmetin Tolmetin: A non-steroidal anti-inflammatory agent (ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL) similar in mode of action to INDOMETHACIN.. tolmetin : A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.	2	1	0	aromatic ketone; monocarboxylic acid; pyrroles	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
tolnaftate [no description available]	2.39	2	0	monothiocarbamic ester	antifungal drug
trazodone Trazodone: A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309). trazodone : An N-arylpiperazine in which one nitrogen is substituted by a 3-chlorophenyl group, while the other is substituted by a 3-(3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl group.	2.06	1	0	monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazolopyridine	adrenergic antagonist; antidepressant; anxiolytic drug; H1-receptor antagonist; sedative; serotonin uptake inhibitor
triacetin Triacetin: A triglyceride that is used as an antifungal agent.. triacetin : A triglyceride obtained by acetylation of the three hydroxy groups of glycerol. It has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.	2.02	1	0	triglyceride	adjuvant; antifungal drug; food additive carrier; food emulsifier; food humectant; fuel additive; plant metabolite; solvent
triamterene Triamterene: A pteridinetriamine compound that inhibits SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS.. triamterene : Pteridine substituted at positions 2, 4 and 7 with amino groups and at position 6 with a phenyl group. A sodium channel blocker, it is used as a diuretic in the treatment of hypertension and oedema.	2.02	1	0	pteridines	diuretic; sodium channel blocker
triclosan [no description available]	5.41	13	1	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic
triflupromazine Triflupromazine: A phenothiazine used as an antipsychotic agent and as an antiemetic.. triflupromazine : A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.	2.05	1	0	organofluorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; first generation antipsychotic
trimebutine Trimebutine: Proposed spasmolytic with possible local anesthetic action used in gastrointestinal disorders.	1.97	1	0	trihydroxybenzoic acid
trimeprazine Trimeprazine: A phenothiazine derivative that is used as an antipruritic.	2.4	2	0	phenothiazines
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	3.42	7	0	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
tropicamide Tropicamide: One of the MUSCARINIC ANTAGONISTS with pharmacologic action similar to ATROPINE and used mainly as an ophthalmic parasympatholytic or mydriatic.	2.4	2	0	acetamides
tulobuterol [no description available]	2.46	2	0	organochlorine compound
tyramine [no description available]	2.05	1	0	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
undecylenic acid undecylenic acid: a fatty acid with a terminal double bond. 10-undecenoic acid : An undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems.. undecenoic acid : A C11, straight-chain fatty acid carrying a C=C double bond at any position.	2.31	1	0	undecenoic acid	antifungal drug; plant metabolite
urethane [no description available]	2.02	1	0	carbamate ester	fungal metabolite; mutagen
usnic acid [no description available]	2.25	1	0	benzofurans
vesamicol vesamicol: RN given refers to parent cpd; structure	2.01	1	0	piperidines
w 7 W 7: RN given refers to parent cpd; structure; calmodulin antagonist	2.01	1	0
2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2h-tetrazolium hydroxide 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2H-tetrazolium hydroxide: structure given in first source	2.04	1	0
3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole: antineoplastic; activates platelet guanylate cyclase; a radiosensitizing agent and guanylate cyclase activator; structure in first source. lificiguat : A member of the class of indazoles that is 1H-indazole which is substituted by a benzyl group at position 1 and a 5-(hydroxymethyl)-2-furyl group at position 3. It is an activator of soluble guanylate cyclase and inhibits platelet aggregation.	2.02	1	0	aromatic primary alcohol; furans; indazoles	antineoplastic agent; apoptosis inducer; platelet aggregation inhibitor; soluble guanylate cyclase activator; vasodilator agent
zaleplon zaleplon: an azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; a hypnotic with less marked effect on psychomotor functions compared to lorazepam. zaleplon : A pyrazolo[1,5-a]pyrimidine having a nitrile group at position 3 and a 3-(N-ethylacetamido)phenyl substituent at the 7-position.	2.07	1	0	nitrile; pyrazolopyrimidine	anticonvulsant; anxiolytic drug; central nervous system depressant; sedative
zolpidem Zolpidem: An imidazopyridine derivative and short-acting GABA-A receptor agonist that is used for the treatment of INSOMNIA.. zolpidem : An imidazo[1,2-a]pyridine compound having a 4-tolyl group at the 2-position, an N,N-dimethylcarbamoylmethyl group at the 3-position and a methyl substituent at the 6-position.	2.41	2	0	imidazopyridine	central nervous system depressant; GABA agonist; sedative
zopiclone zopiclone: S(+)-enantiomer of racemic zopiclone; azabicyclo(4.3.0)nonane; a nonbenzodiazepine; one of the so-called of Z drugs (zopiclone, eszopiclone, zolpidem, and zaleplon) for which there is some correlation with tumors; was term of zopiclone 2004-2007. zopiclone : A pyrrolo[3,4-b]pyrazine compound having a 4-methylpiperazine-1-carboxyl group at the 5-position, a 5-chloropyridin-2-yl group at the 6-position and an oxo-substituent at the 7-position.	3.2	5	0	monochloropyridine; pyrrolopyrazine	central nervous system depressant; sedative
hydrocortisone acetate hydrocortisone acetate: RN given refers to cpd without isomeric designation	2.41	2	0	cortisol ester; tertiary alpha-hydroxy ketone
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	3.8	2	1	mitomycin	alkylating agent; antineoplastic agent
corticosterone [no description available]	2.74	3	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
prednisolone Prednisolone: A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.. prednisolone : A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.	4.36	20	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; drug metabolite; environmental contaminant; immunosuppressive agent; xenobiotic
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	3.18	5	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.93	4	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
alloxan Alloxan: Acidic compound formed by oxidation of URIC ACID. It is isolated as an efflorescent crystalline hydrate.. alloxan : A member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.	2.13	1	0	pyrimidone	hyperglycemic agent; metabolite
thymidine [no description available]	2.9	4	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
floxuridine Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.	2.46	2	0	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent
piperonyl butoxide [no description available]	2.1	1	0	benzodioxoles	pesticide synergist
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	3.76	9	0	benzimidazole; polycyclic heteroarene
2-aminophenol [no description available]	2.13	1	0	aminophenol	bacterial metabolite
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.13	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.54	2	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
dextroamphetamine Dextroamphetamine: The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.. (S)-amphetamine : A 1-phenylpropan-2-amine that has S configuration.	2.46	2	0	1-phenylpropan-2-amine	adrenergic agent; adrenergic uptake inhibitor; dopamine uptake inhibitor; dopaminergic agent; neurotoxin; sympathomimetic agent
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	3.42	7	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
norethindrone acetate norethisterone acetate : A 3-oxo Delta(4)-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.	2.21	1	0	3-oxo-Delta(4) steroid; acetate ester; terminal acetylenic compound	progestin; synthetic oral contraceptive
spironolactone Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.	5.19	6	2	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic
aldosterone [no description available]	2.06	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
penicillamine Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.	3.48	7	0	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen
tetrahydrocortisol [no description available]	2.38	2	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3alpha-hydroxy steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	1.99	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	4.8	7	1	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
methylprednisolone acetate Methylprednisolone Acetate: Methylprednisolone derivative that is used as an anti-inflammatory agent for the treatment of ALLERGY and ALLERGIC RHINITIS; ASTHMA; and BURSITIS; and for the treatment of ADRENAL INSUFFICIENCY.. methylprednisolone acetate : An acetate ester resulting from the formal condensation of the 21-hydroxy function of 6alpha-methylprednisolone compound with acetic acid.	2.17	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; acetate ester; glucocorticoid; steroid ester; tertiary alpha-hydroxy ketone	anti-inflammatory drug
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.93	4	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
penicillin g Penicillin G: A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.. benzylpenicillin : A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group.	2.7	3	0	penicillin allergen; penicillin	antibacterial drug; drug allergen; epitope
idoxuridine [no description available]	2.04	1	0	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
pilocarpine Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.	3.69	10	0	pilocarpine	antiglaucoma drug
pentylenetetrazole Pentylenetetrazole: A pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive GAMMA-AMINOBUTYRIC ACID antagonist. Pentylenetetrazole has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility.. pentetrazol : An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other respiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.	2.52	2	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	1.96	1	0	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.52	2	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	4.02	13	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	4.74	9	0	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
benz(a)anthracene benz(a)anthracene: 4 fused rings of which one is angular in contrast to the linear NAPHTHACENES. tetraphene : An angular ortho-fused polycyclic arene consisting of four fused benzene rings.	2	1	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	3.66	9	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	3.84	11	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	3.5	7	0	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	4.08	14	0	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
allyl isothiocyanate allyl isothiocyanate: used in the manufacture of flavors, war gases; medical use as a counterirritant; structure. allyl isothiocyanate : An isothiocyanate with the formula CH2=CHCH2N=C=S. A colorless oil with boiling point 152degreeC, it is responsible for the pungent taste of mustard, horseradish, and wasabi.	2.1	1	0	alkenyl isothiocyanate; isothiocyanate	antimicrobial agent; antineoplastic agent; apoptosis inducer; lachrymator; metabolite
cetrimonium bromide cetyltrimethylammonium bromide : The organic bromide salt that is the bromide salt of cetyltrimethylammonium; one of the components of the topical antiseptic cetrimide.	2.03	1	0	organic bromide salt; quaternary ammonium salt	detergent; surfactant
dimazine dimazine: RN given refers to parent cpd. 1,1-dimethylhydrazine : A member of the class of hydrazines that is hydrazine substituted by two methyl groups at position 1.	2.13	1	0	hydrazines	carcinogenic agent; fuel; teratogenic agent
chlorobutanol [no description available]	2.41	2	0	tertiary alcohol
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	7.32	32	1	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	4.41	4	1	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
testosterone propionate Testosterone Propionate: An ester of TESTOSTERONE with a propionate substitution at the 17-beta position.. androgen : A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.	2.15	1	0	steroid ester
9,10-dimethyl-1,2-benzanthracene 9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.	2.05	1	0	ortho-fused polycyclic arene; tetraphenes	carcinogenic agent
apomorphine Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.	2.01	1	0	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
methyltestosterone Methyltestosterone: A synthetic hormone used for androgen replacement therapy and as an hormonal antineoplastic agent (ANTINEOPLASTIC AGENTS, HORMONAL).. methyltestosterone : A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.	2.39	2	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; enone	anabolic agent; androgen; antineoplastic agent
puromycin aminonucleoside 3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine: structure in first source. 3'-amino-3'-deoxy-N(6),N(6)-dimethyladenosine : Puromycin derivative that lacks the methoxyphenylalanyl group on the amine of the sugar ring.	2.15	1	0	3'-deoxyribonucleoside; adenosines
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	3.28	6	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
2,3,4,6-tetrachlorophenol 2,3,4,6-tetrachlorophenol: RN given refers to parent cpd; see also record for tetrachlorophenol with locants for chloro groups not specified. 2,3,4,6-tetrachlorophenol : A tetrachlorophenol in which the chlorines are located at positions 2, 3, 4, and 6.	3.91	12	0	tetrachlorophenol	xenobiotic metabolite
uridine [no description available]	2.05	1	0	uridines	drug metabolite; fundamental metabolite; human metabolite
kanamycin a Kanamycin: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.. kanamycin : Kanamycin is a naturally occurring antibiotic complex from Streptomyces kanamyceticus that consists of several components: kanamycin A, the major component (also usually designated as kanamycin), and kanamycins B, C, D and X the minor components.	2.52	2	0	kanamycins	bacterial metabolite
bromodeoxyuridine Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.	2.98	4	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	3.13	5	0	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
carbostyril Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.	4.77	9	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
piperoxan Piperoxan: A benzodioxane alpha-adrenergic blocking agent with considerable stimulatory action. It has been used to diagnose PHEOCHROMOCYTOMA and as an antihypertensive agent.	2.41	2	0
phenylephrine Phenylephrine: An alpha-1 adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent.. phenylephrine : A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.	3.31	6	0	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	3.21	5	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	4.15	15	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
tributyrin tributyrin: structure. tributyrin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.	2.07	1	0	butyrate ester; triglyceride	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor; prodrug; protective agent
p-aminoazobenzene p-Aminoazobenzene: Used in the form of its salts as a dye and as an intermediate in manufacture of Acid Yellow, diazo dyes, and indulines.. 4-(phenylazo)aniline : Azobenzene substituted at one of the 4-positions by an amino group. It has a role as a dye and an allergen.	2.79	3	0
p-dimethylaminoazobenzene p-Dimethylaminoazobenzene: A reagent used mainly to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens (NTP 85-002, p. 89) published in 1985, this compound may reasonably be anticipated to be a carcinogen. (Merck, 11th ed)	2.75	3	0	azobenzenes
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2.	3.72	9	0	benzenes; primary alcohol	Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	5.41	58	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cysteamine Cysteamine: A mercaptoethylamine compound that is endogenously derived from the COENZYME A degradative pathway. The fact that cysteamine is readily transported into LYSOSOMES where it reacts with CYSTINE to form cysteine-cysteamine disulfide and CYSTEINE has led to its use in CYSTINE DEPLETING AGENTS for the treatment of CYSTINOSIS.. cysteamine : An amine that consists of an ethane skeleton substituted with a thiol group at C-1 and an amino group at C-2.	2.82	3	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	2.75	3	0	aryl beta-D-glucoside; dihydrochalcones; monosaccharide derivative	antioxidant; plant metabolite
methoxamine Methoxamine: An alpha-1 adrenergic agonist that causes prolonged peripheral VASOCONSTRICTION.. methoxamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine .	2.4	2	0	amphetamines	alpha-adrenergic agonist; antihypotensive agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	3.57	7	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
methicillin Methicillin: One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.. methicillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.	2.08	1	0	penicillin allergen; penicillin	antibacterial drug
cloxacillin Cloxacillin: A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.. cloxacillin : A semisynthetic penicillin antibiotic carrying a 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido group at position 6.	2.43	2	0	penicillin allergen; penicillin; semisynthetic derivative	antibacterial agent; antibacterial drug
methylene blue Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.	4.59	23	0	organic chloride salt	acid-base indicator; antidepressant; antimalarial; antimicrobial agent; antioxidant; cardioprotective agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 4.6.1.2 (guanylate cyclase) inhibitor; fluorochrome; histological dye; neuroprotective agent; physical tracer
4-toluenesulfonic acid 4-toluenesulfonic acid: RN given refers to parent cpd; other RNs in 9th CI Form Index. toluene-4-sulfonic acid : An arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.	2.04	1	0	arenesulfonic acid; toluenes
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	3.44	7	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
aniline [no description available]	2.94	4	0	anilines; primary arylamine
calcium acetate calcium acetate: a principal compound used as phosphate binders in patients with chronic renal failure; used like sevelamer. calcium acetate : The calcium salt of acetic acid. It is used, commonly as a hydrate, to treat hyperphosphataemia (excess phosphate in the blood) in patients with kidney disease: the calcium ion combines with dietary phosphate to form (insoluble) calcium phosphate, which is excreted in the faeces.	2.1	1	0	calcium salt	chelator
dimethylnitrosamine Dimethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties. It causes serious liver damage and is a hepatocarcinogen in rodents.	1.97	1	0	nitrosamine	geroprotector; mutagen
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	2.93	4	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
carbaryl Carbaryl: A carbamate insecticide and parasiticide. It is a potent anticholinesterase agent belonging to the carbamate group of reversible cholinesterase inhibitors. It has a particularly low toxicity from dermal absorption and is used for control of head lice in some countries.. carbaryl : A carbamate ester obtained by the formal condensation of 1-naphthol with methylcarbamic acid.	2.02	1	0	carbamate ester; naphthalenes	acaricide; agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant growth retardant
uridine triphosphate Uridine Triphosphate: Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety.	2.03	1	0	pyrimidine ribonucleoside 5'-triphosphate; uridine 5'-phosphate	Escherichia coli metabolite; mouse metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	4.72	28	0	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	2.95	4	0	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
1,2-dipalmitoylphosphatidylcholine 1,2-Dipalmitoylphosphatidylcholine: Synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of PULMONARY SURFACTANTS.	3.44	7	0
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	6.36	49	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
colchicine (S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.	3.32	6	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
n-hexanal [no description available]	2.48	2	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
oxacillin Oxacillin: An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.. oxacillin : A penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6beta.	2.01	1	0	penicillin	antibacterial agent; antibacterial drug
cycloheximide Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.	2.69	3	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2.15	1	0	psoralens	plant metabolite
thiamine hydrochloride thiamine hydrochloride : A hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid.	2.25	1	0	hydrochloride; vitamin B1	insect repellent
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	3.63	9	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	1.97	1	0	barbiturates	allergen; xenobiotic
chloroform Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.	2.44	2	0	chloromethanes; one-carbon compound	carcinogenic agent; central nervous system drug; inhalation anaesthetic; non-polar solvent; refrigerant
dimethyl sulfone [no description available]	2.07	1	0	sulfone
bromoacetate [no description available]	2.05	1	0	carboxylic acid; organohalogen compound
dimethylformamide Dimethylformamide: A formamide in which the amino hydrogens are replaced by methyl groups.. N,N-dimethylformamide : A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.	3.69	9	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
cycloserine Cycloserine: Antibiotic substance produced by Streptomyces garyphalus.. D-cycloserine : A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine--D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).	2.02	1	0	4-amino-1,2-oxazolidin-3-one; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic; zwitterion	antiinfective agent; antimetabolite; antitubercular agent; metabolite; NMDA receptor agonist
17-alpha-hydroxyprogesterone 17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.	2.9	4	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; tertiary alpha-hydroxy ketone	human metabolite; metabolite; mouse metabolite; progestin
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	3.29	6	0	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	4.39	20	0	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
2-thiomalic acid [no description available]	2.61	2	0	C4-dicarboxylic acid
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	3.94	12	0	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	2.97	4	0	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	3.33	6	0	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
methaqualone Methaqualone: A quinazoline derivative with hypnotic and sedative properties. It has been withdrawn from the market in many countries because of problems with abuse. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). methaqualone : A member of the class of quinazolines that is quinazolin-4-one substituted at positions 2 and 3 by methyl and o-tolyl groups respectively. A depressant that increases the activity of the GABA receptors in the brain and nervous system, it is used as a sedative and hypnotic medication. It became popular as a recreational drug and club drug in the late 1960s and 1970s.	2	1	0	quinazolines	GABA agonist; sedative
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	5.11	42	0	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	3.14	5	0	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	4.65	25	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	2.47	2	0	alkene; gas molecular entity	plant hormone; refrigerant
methyl chloride Methyl Chloride: A hydrocarbon used as an industrial solvent. It has been used as an aerosal propellent, as a refrigerant and as a local anesthetic. (From Martindale, The Extra Pharmacopoeia, 31st ed, p1403). chlorocarbon : Compounds consisting wholly of chlorine and carbon.. chloromethane : A one-carbon compound that is methane in which one of the hydrogens is replaced by a chloro group.	2.05	1	0	chloromethanes; methyl halides	marine metabolite; mutagen; refrigerant
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.02	1	0	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	2.78	3	0	boranes; mononuclear parent hydride
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2.05	1	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	4.98	37	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	3.28	6	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	3.18	5	0	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
iodoform [no description available]	2.11	1	0	iodomethanes
nitromethane nitromethane: structure. nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models.	2.08	1	0	primary nitroalkane; volatile organic compound	EC 4.3.1.3 (histidine ammonia-lyase) inhibitor; explosive; NMR chemical shift reference compound; polar aprotic solvent
propylene oxide propylene oxide: structure. 1,2-epoxypropane : An epoxide that is oxirane substituted by a methyl group at position 2.	2.05	1	0	epoxide
tetramethylammonium tetramethylammonium: RN given refers to parent cpd. tetramethylammonium : The simplest quaternary ammonium cation, comprising a central nitrogen linked to four methyl groups.	2.96	4	0	quaternary ammonium ion
tert-butyl alcohol tert-Butyl Alcohol: An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.. tert-butanol : A tertiary alcohol alcohol that is isobutane substituted by a hydroxy group at position 2.	2.72	3	0	tertiary alcohol	human xenobiotic metabolite
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	2	1	0	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
triamcinolone acetonide Triamcinolone Acetonide: An esterified form of TRIAMCINOLONE. It is an anti-inflammatory glucocorticoid used topically in the treatment of various skin disorders. Intralesional, intramuscular, and intra-articular injections are also administered under certain conditions.. triamcinolone acetonide : A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.	2.96	4	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; cyclic ketal; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
gibberellic acid gibberellic acid: RN given refers to (1alpha,2beta,4aalpha,4bbeta,10beta)-isomer; structure. gibberellin A3 : A C19-gibberellin that is a pentacyclic diterpenoid responsible for promoting growth and elongation of cells in plants. Initially identified in Gibberella fujikuroi,it differs from gibberellin A1 in the presence of a double bond between C-3 and C-4.	2.1	1	0	C19-gibberellin; gibberellin monocarboxylic acid; lactone; organic heteropentacyclic compound	mouse metabolite; plant metabolite
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	1.99	1	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
acedapsone Acedapsone: Acetylated sulfone that is slowly metabolized to give long-term, low blood levels of DAPSONE. It has antimicrobial and antimalarial action, but is mainly used as a depot leprostatic agent.. acedapsone : A sulfone that is dapsone in which both of the amino groups been acetylation. An antimicrobial drug, it also has antimalarial activity.	2	1	0	acetamides; anilide; secondary carboxamide; sulfone	antimalarial; antimicrobial drug
divinyl sulfone divinyl sulfone: cross-linking reagent for agarose gels. divinyl sulfone : A sulfone compound having two S-vinyl substituents.	2.51	2	0	sulfone	cross-linking reagent
tabun tabun: proposed as military nerve gas and exptl cholinesterase inhibitor; extremely poisonous; structure	2.91	4	0
tromethamine Tromethamine: An organic amine proton acceptor. It is used in the synthesis of surface-active agents and pharmaceuticals; as an emulsifying agent for cosmetic creams and lotions, mineral oil and paraffin wax emulsions, as a biological buffer, and used as an alkalizer. (From Merck, 11th ed; Martindale, The Extra Pharmacopoeia, 30th ed, p1424)	3.74	10	0	primary amino compound; triol	buffer
ethyl citrate ethyl citrate: structure	2.02	1	0	carbonyl compound
quinic acid (-)-quinic acid : The (-)-enantiomer of quinic acid.	2.21	1	0
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	2.69	2	0	mercaptopropanoic acid	algal metabolite
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	4.01	12	0	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
isoprene isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.	2.87	3	0	alkadiene; hemiterpene; volatile organic compound	plant metabolite
isobutyronitrile isobutyronitrile : An aliphatic nitrile that is acetonitrile in which two of the hydrogens have been replaced by methyl groups.	2.07	1	0	aliphatic nitrile; volatile organic compound	polar aprotic solvent
2-butanol 2-butanol: RN given is for parent cpd without isomeric designation. butan-2-ol : A secondary alcohol that is butane substituted by a hydroxy group at position 2.	2.25	1	0	secondary alcohol
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	2.04	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
acrylamide [no description available]	3.88	11	0	acrylamides; N-acylammonia; primary carboxamide	alkylating agent; carcinogenic agent; Maillard reaction product; mutagen; neurotoxin
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	4.67	26	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
methacrylamide [no description available]	2.13	1	0	acrylamides; primary carboxamide
camphene camphene : A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.	2.55	2	0	carbobicyclic compound; monoterpene	fragrance; plant metabolite
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	4.43	19	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
alpha-pinene [no description available]	2.42	2	0	pinene	plant metabolite
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	2.03	1	0	enoate ester; methyl ester	allergen; polymerisation monomer
dehydrocholic acid Dehydrocholic Acid: A semisynthetic bile acid made from cholic acid. It is used as a cholagogue, hydrocholeretic, diuretic, and as a diagnostic aid.. 3,7,12-trioxo-5beta-cholanic acid : An oxo-5beta-cholanic acid in which three oxo substituents are located at positions 3, 7 and 12 on the cholanic acid skeleton.	2.06	1	0	12-oxo steroid; 3-oxo-5beta-steroid; 7-oxo steroid; oxo-5beta-cholanic acid	gastrointestinal drug
taurocholic acid Taurocholic Acid: The product of conjugation of cholic acid with taurine. Its sodium salt is the chief ingredient of the bile of carnivorous animals. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and cholerectic.. taurocholate : An organosulfonate oxoanion that is the conjugate base of taurocholic acid.. taurocholic acid : A bile acid taurine conjugate of cholic acid that usually occurs as the sodium salt of bile in mammals.	3.82	11	0	amino sulfonic acid; bile acid taurine conjugate	human metabolite
1,8-naphthalenedicarboxylic acid anhydride 1,8-naphthalenedicarboxylic acid anhydride: used as seed protector from herbicides	1.98	1	0	cyclic dicarboxylic anhydride
rhodamine b rhodamine B: RN & N1 from 9th CI Form Index; RN given refers to parent cpd; structure in Merck Index, 9th ed, #7973; TETRAETHYLRHODAMINE was see RHODAMINES 1975-93; use RHODAMINES to search TETRAETHYLRHODAMINE 1975-93. rhodamine B : An organic chloride salt having N-[9-(2-carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium as the counterion. An amphoteric dye commonly used as a fluorochrome.	4.61	24	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
visnagin visnagin: from Musineon divaricatum. visnagin : A furanochromone that is furo[3,2-g]chromen-5-one which is substituted at positions 4 and 7 by methoxy and methyl groups, respectively. Found in the toothpick-plant, Ammi visnaga.	2.07	1	0	aromatic ether; furanochromone; polyketide	anti-inflammatory agent; antihypertensive agent; EC 1.1.1.37 (malate dehydrogenase) inhibitor; phytotoxin; plant metabolite; vasodilator agent
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	3.01	4	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
dichlorodicyanobenzoquinone dichlorodicyanobenzoquinone: request from searcher	2.08	1	0
9,10-anthraquinone 9,10-anthraquinone : An anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.	2.02	1	0	anthraquinone
phthalic anhydride phthalic anhydride : The cyclic dicarboxylic anhydride that is the anhydride of phthalic acid.	1.98	1	0	2-benzofurans; cyclic dicarboxylic anhydride	allergen
brompheniramine Brompheniramine: Histamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria.. brompheniramine : Pheniramine in which the hydrogen at position 4 of the phenyl substituent is substituted by bromine. A histamine H1 receptor antagonist, brompheniramine is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis.	3.34	6	0	organobromine compound; pyridines	anti-allergic agent; H1-receptor antagonist
phensuximide phensuximide: major descriptor (73-84); on-line search SUCCINIMIDES (73-84); Index Medicus search PHENSUXIMIDE (73-84); RN given refers to cpd without isomeric designation	2	1	0	pyrrolidines
propoxycaine Propoxycaine: A local anesthetic of the ester type that has a rapid onset of action and a longer duration of action than procaine hydrochloride. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1017)	2.45	2	0	benzoate ester
1-nitronaphthalene 1-nitronaphthalene: RN given refers to cpd with locant for nitro moiety in 1 position. 1-nitronaphthalene : A mononitronaphthalene substituted by a nitro group at position 1.. mononitronaphthalene : A nitronaphthalene carrying a single nitro group at unspecified position.. nitronaphthalene : A nitroarene that is naphthalene substituted by at least one nitro group.	2.02	1	0	mononitronaphthalene	environmental contaminant; mouse metabolite
fluorene [no description available]	2.47	2	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
carbazole carbazole: structure in first source	2.42	2	0	carbazole
1-naphthaleneacetic acid 1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.	2.74	3	0	naphthylacetic acid	synthetic auxin
penicillin v Penicillin V: A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.. phenoxymethylpenicillin : A penicillin compound having a 6beta-(phenoxyacetyl)amino side-chain.	2.17	1	0	penicillin allergen; penicillin
isosorbide dinitrate Isosorbide Dinitrate: A vasodilator used in the treatment of ANGINA PECTORIS. Its actions are similar to NITROGLYCERIN but with a slower onset of action.	2.4	2	0	glucitol derivative; nitrate ester	nitric oxide donor; vasodilator agent
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	4.13	3	1
2,4,6-trichlorophenol [no description available]	2.42	2	0	trichlorophenol	carcinogenic agent
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	6.85	60	1	pyrrolidin-2-ones
2-furoic acid 2-furoic acid: RN given refers to parent cpd. furoic acid : A monocarboxylic acid that consists of a furan ring having a single carboxylic acid group on any ring position and derivatives thereof.. 2-furoic acid : A furoic acid having the carboxylic acid group located at position 2.	2.31	1	0	furoic acid	bacterial xenobiotic metabolite; human xenobiotic metabolite; inhibitor; plant metabolite; Saccharomyces cerevisiae metabolite
1-chloro-2-nitrobenzene [no description available]	2.07	1	0	C-nitro compound; monochlorobenzenes
2-nitrophenol nitrophenol : Any member of the class of phenols or substituted phenols carrying at least 1 nitro group.	2.31	1	0	2-nitrophenols
picric acid picric acid: used as antiseptic, astringent & stimulant for epitheliazation; structure. picric acid : A C-nitro compound comprising phenol having three nitro substtituents at the 2-, 4- and 6-positions.	2.05	1	0	C-nitro compound	antiseptic drug; explosive; fixative
pyromellitic acid pyromellitic acid: RN given refers to parent cpd; structure. pyromellitic acid : A tetracarboxylic acid that is benzene substituted by four carboxy groups at positions 1, 2, 4 and 5 respectively.	2.01	1	0	benzoic acids; tetracarboxylic acid
thymol Thymol: A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.. thymol : A phenol that is a natural monoterpene derivative of cymene.	3.85	10	0	monoterpenoid; phenols	volatile oil component
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.07	1	0	hydroxybenzaldehyde	nematicide; plant metabolite
alpha-bromonaphthalene [no description available]	2.73	3	0
1-naphthol 1-naphthol: RN given refers to parent cpd. 1-naphthol : A naphthol carrying a hydroxy group at position 1.. hydroxynaphthalene : Any member of the class of naphthalenes that is naphthalene carrying one or more hydroxy groups.	3.33	6	0	naphthol	genotoxin; human xenobiotic metabolite
1-naphthylphenylamine N-phenyl-1-naphthylamine: RN given refers to 1-naphthylamine cpd; structure	2.49	2	0	naphthalenes
bicyclohexanone bicyclohexanone: structure	2.13	1	0
2-phenylphenol 2-phenylphenol: RN given refers to parent cpd; structure. biphenyl-2-ol : A member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits.	2.71	3	0	hydroxybiphenyls	antifungal agrochemical; environmental food contaminant
xanthone xanthone : The parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9.	2.01	1	0	xanthones	insecticide
beta-glucono-1,5-lactone beta-glucono-1,5-lactone: structure. D-glucono-1,5-lactone : An aldono-1,5-lactone obtained from D-gluconic acid.	1.99	1	0	aldono-1,5-lactone; gluconolactone	animal metabolite; mouse metabolite
pseudoephedrine Pseudoephedrine: A phenethylamine that is an isomer of EPHEDRINE which has less central nervous system effects and usage is mainly for respiratory tract decongestion.. pseudoephedrine : A member of the class of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group.	2.77	3	0	phenylethanolamines; secondary alcohol; secondary amino compound	anti-asthmatic drug; bronchodilator agent; central nervous system drug; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
michler's ketone [no description available]	2.41	1	0	benzophenones
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.03	1	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
uvitex swn Uvitex SWN: optical brightner from Ciba; structure	2.1	1	0	7-aminocoumarins	fluorochrome
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	3.43	7	0	naphthylamine	carcinogenic agent
tolonium chloride Tolonium Chloride: A phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery.. tolonium chloride : An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both in metachromatic and orthochromatic techniques.	2.41	1	0
pyronine Pyronine: Xanthene dye used as a bacterial and biological stain. Synonyms: Pyronin; Pyronine G; Pyronine Y. Use also for Pyronine B. which is diethyl-rather than dimethylamino-.. pyronin Y : An organic chloride salt having 6-(dimethylamino)-N,N-dimethyl-3H-xanthen-3-iminium as the cation. Used with methyl green to selectively demonstrate RNA (red) in contrast to DNA (green) with the Unna-Pappenheim method.	2.74	3	0	iminium salt; organic chloride salt	histological dye
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.05	1	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
4-phenylphenol 4-phenylphenol: RN given refers to cpd without isomeric designation. biphenyl-4-ol : A member of the class of hydroxybiphenyls that is biphenyl carrying a hydroxy group at position 4.	2.03	1	0	hydroxybiphenyls
3-hydroxy-2-naphthoic acid 3-hydroxy-2-naphthoic acid: RN given refers to parent cpd	2.43	2	0	naphthoic acid
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.77	3	0	xanthene
phenothiazine 10H-phenothiazine : The 10H-tautomer of phenothiazine.	2.6	1	0	phenothiazine	ferroptosis inhibitor; plant metabolite; radical scavenger
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	2.43	2	0	biphenyls; substituted aniline	carcinogenic agent
2-naphthoic acid 2-naphthoic acid: RN given refers to parent cpd. 2-naphthoic acid : A naphthoic acid that is naphthalene carrying a carboxy group at position 2.	2.45	2	0	naphthoic acid	mouse metabolite; xenobiotic metabolite
1-phenylpropanol 1-phenylpropanol: structure in first source	2.44	2	0	organic molecular entity
mecoprop mecoprop: RN given refers to cpd without isomeric designation; structure. 2-(4-chloro-2-methylphenoxy)propanoic acid : A monocarboxylic acid that is lactic acid in which the hydroxyl hydrogen is replaced by a 4-chloro-2-methylphenyl group.. mecoprop : A racemate comprising equimolar amounts of (R)- and (S)-mecoprop.	2	1	0	aromatic ether; monocarboxylic acid; monochlorobenzenes
benzanilide [no description available]	2.05	1	0
synephrine [no description available]	2.48	2	0	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	4	13	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
benzylparaben [no description available]	2.5	2	0	benzoate ester; benzyl ester
butylparaben [no description available]	2.04	1	0	organic molecular entity
benzoyl peroxide Benzoyl Peroxide: A peroxide derivative that has been used topically for BURNS and as a dermatologic agent in the treatment of ACNE and POISON IVY DERMATITIS. It is used also as a bleach in the food industry.	2.02	1	0	carbonyl compound
2-methyl-4-chlorophenoxyacetic acid 2-Methyl-4-chlorophenoxyacetic Acid: A powerful herbicide used as a selective weed killer.. (4-chloro-2-methylphenoxy)acetic acid : A chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2.	2.43	2	0	chlorophenoxyacetic acid; monochlorobenzenes	environmental contaminant; phenoxy herbicide; synthetic auxin
2-chloroaniline [no description available]	2.1	1	0
1,2-diaminobenzene 1,2-diaminobenzene: RN given refers to parent cpd. 1,2-phenylenediamine : A phenylenediamine in which the two amino groups are ortho to each other.	2.08	1	0	phenylenediamine	hydrogen donor
2-chlorophenol chlorophenol : A halophenol that is any phenol containing one or more covalently bonded chlorine atoms.	2.76	2	0	2-halophenol; monochlorophenol
styrene oxide styrene oxide: structure. styrene oxide : An epoxide that is oxirane in which one of the hydrogens has been replaced by a phenyl group.	2.05	1	0	epoxide	human xenobiotic metabolite
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	3.13	5	0	butan-4-olide	metabolite; neurotoxin
n-methylpyrrole [no description available]	2.03	1	0	pyrroles
soman Soman: An organophosphorus compound that inhibits cholinesterase. It causes seizures and has been used as a chemical warfare agent.	3.08	5	0	phosphonic ester
lactobionic acid [no description available]	2.99	4	0	disaccharide	antioxidant
2,4-dinitroaniline 2,4-dinitroaniline : A nitroaniline consisting of an aniline core having two nitro substituents located at the 2- and 4-positions.	2.5	2	0	nitroaniline
ethyl lactate ethyl lactate: RN given refers to cpd with unspecified isomeric designation. ethyl 2-hydroxypropanoate : The ethyl ester obtained of 2-hydroxypropanoic acid.	2	1	0	ethyl ester; lactate ester; secondary alcohol	metabolite
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	3.19	5	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.02	1	0	aldehyde; furans	Maillard reaction product; metabolite
4-tert-butyltoluene [no description available]	1.98	1	0
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	2	1	0	phenols	allergen
4-tert-butylbenzoic acid 4-tert-butylbenzoic acid: RN given refers to parent cpd	2.51	2	0	alkylbenzene
pyrrolidonecarboxylic acid Pyrrolidonecarboxylic Acid: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism.. 5-oxo-L-proline : An optically active form of 5-oxoproline having L-configuration.	2.53	2	0	5-oxoproline; L-proline derivative; non-proteinogenic L-alpha-amino acid	algal metabolite
alpha-methylstyrol [no description available]	2.02	1	0	olefinic compound
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	2.1	1	0	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2.46	2	0	nitroarene; nitrobenzenes
3-nitroaniline 3-nitroaniline: used as a sole source of nitrogen , carbon and energy	2.07	1	0
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	4.01	13	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
sym-trinitrobenzene Trinitrobenzenes: Benzene derivatives which are substituted with three nitro groups in any position.. 1,3,5-trinitrobenzene : A trinitrobenzene in which each of the nitro groups is meta- to the other two.	2.02	1	0	trinitrobenzene	explosive
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2.44	2	0	botanical anti-fungal agent; carvones	allergen
methylparaben methylparaben: used as a preservative in cosmetics but potentiates UV-induced damage of skin; RN given refers to parent cpd. methylparaben : A 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol. It is the most frequently used antimicrobial preservative in cosmetics. It occurs naturally in several fruits, particularly in blueberries.	1.98	1	0	paraben	antifungal agent; antimicrobial food preservative; neuroprotective agent; plant metabolite
alpha phellandrene alpha phellandrene: can be irritating to, & absorbed by the skin; ingestion can cause vomiting, diarrhea; RN given refers to cpd without isomeric designation; structure. alpha-phellandrene : One of a pair of phellandrene cyclic monoterpene double-bond isomers in which both double bonds are endocyclic (cf. alpha-phellandrene, where one of them is exocyclic).	2.13	1	0	cyclohexadiene; phellandrene	antimicrobial agent; plant metabolite; volatile oil component
gamma-terpinene gamma-terpinene: RN given refers to gamma-terpinene; structure. gamma-terpinene : One of three isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton.	2.41	1	0	cyclohexadiene; monoterpene	antioxidant; human xenobiotic metabolite; plant metabolite; volatile oil component
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.58	2	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
4-toluic acid 4-toluic acid: RN given refers to parent cpd; structure. p-toluic acid : A methylbenzoic acid in which the methyl substituent is located at position 4.	1.98	1	0	methylbenzoic acid
4-nitroaniline [no description available]	2.07	1	0	nitroaniline	bacterial xenobiotic metabolite
terephthaloyl chloride terephthaloyl chloride: cross-links albumin	2	1	0
terephthalic acid terephthalic acid: RN given refers to 1,4-benzenedicarboxylic acid. terephthalic acid : A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.	2.01	1	0	benzenedicarboxylic acid
ethylbenzene [no description available]	2.93	4	0	alkylbenzene
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.41	2	0	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
4-vinylpyridine 4-vinylpyridine: reagent for blocking cysteine function in proteins; RN given refers to parent cpd	2.49	2	0
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.4	2	0	aralkylamine; primary amine	allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite
methylaniline methylaniline: RN given refers to parent cpd. methylaniline : A substituted aniline carrying one or more methyl groups at unspecified positions.	2.1	1	0	methylaniline; phenylalkylamine; secondary amine
anisole anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.	2.05	1	0	monomethoxybenzene	plant metabolite
methylphenylsulfide thioanisole : An aryl sulfide that is thiophenol in which the hydrogen of the thiol group has been replaced by a methyl group.	2.47	2	0	aryl sulfide; benzenes
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	5.23	3	1	quinuclidines; saturated organic heterobicyclic parent
triclocarban triclocarban: bacteriostat; antiseptic in soaps & other cleansing solns; germicide; structure. triclocarban : A member of the class of phenylureas that is urea substituted by a 4-chlorophenyl group and a 3,4-dichlorophenyl group at positions 1 and 3 respectively.	2.02	1	0	dichlorobenzene; monochlorobenzenes; phenylureas	antimicrobial agent; antiseptic drug; disinfectant; environmental contaminant; xenobiotic
pyridostigmine bromide Pyridostigmine Bromide: A cholinesterase inhibitor with a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.	3.46	1	1	pyridinium salt
fenuron fenuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which one of the nitrogens is substituted by a phenyl group while the other is substituted by two methyl groups. It is a herbicide used for the control of weeds in beetroot as well as various vegetable and ornamental crops.	2.02	1	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea	agrochemical; environmental contaminant; herbicide; photosystem-II inhibitor; xenobiotic
triethanolamine triethanolamine: RN given refers to parent cpd. triethanolamine : A tertiary amino compound that is ammonia in which each of the hydrogens is substituted by a 2-hydroxyethyl group.	4.93	11	0	amino alcohol; tertiary amino compound; triol	buffer; surfactant
boric acid [no description available]	2.95	4	0	boric acids	astringent
phenylisothiocyanate phenylisothiocyanate: structure. phenyl isothiocyanate : An isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation.	2.02	1	0	isothiocyanate	allergen; reagent
1-phenyl-2-propanone 1-phenyl-2-propanone: analog of propiophenone where carbonyl group is on the 2 carbon atom instead of the 1 carbon atom of the side chain. phenylacetone : A propanone that is propan-2-one substituted by a phenyl group at position 1.	2.05	1	0	methyl ketone; propanones
methylhexaneamine [no description available]	2.11	1	0	alkylamine
ethyl butyrate ethyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of ethanol with the carboxy group of butyric acid.	2.11	1	0	butyrate ester	plant metabolite
ethyl carbonate [no description available]	2.08	1	0	carbonate ester
caprolactam Caprolactam: Cyclic amide of caproic acid used in manufacture of synthetic fibers of the polyamide type. Can cause local irritation.. epsilon-caprolactam : A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.	2.11	1	0	caprolactams	human blood serum metabolite
citronellal citronellal: aldehyde of citronellol; found in citronella oil. citronellal : A monoterpenoid, the main component of citronella oil which gives it its distinctive lemon aroma.	2.57	2	0	aldehyde; monoterpenoid	antifungal agent; metabolite
ethyl laurate ethyl laurate : A fatty acid ethyl ester of lauric acid.	1.98	1	0	fatty acid ethyl ester	metabolite
1,2-epoxybutane 1,2-epoxybutane: RN given refers to cpd with unspecified isomeric designation	2.05	1	0	epoxide
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	6.09	36	0	epoxide; organochlorine compound
glycidyl methacrylate glycidyl methacrylate: RN given refers to monomer. glycidyl methacrylate : An enoate ester obtained by formal condensation of the carboxy group of methacrylic acid with the hydroxy group of glycidol.	3.7	9	0	enoate ester; epoxide
acrolein [no description available]	3.76	8	0	enal	herbicide; human xenobiotic metabolite; toxin
allylamine Allylamine: Possesses an unusual and selective cytotoxicity for VASCULAR SMOOTH MUSCLE cells in dogs and rats. Useful for experiments dealing with arterial injury, myocardial fibrosis or cardiac decompensation.	2.44	2	0	alkylamine
acrylonitrile [no description available]	2.44	2	0	aliphatic nitrile; volatile organic compound	antifungal agent; carcinogenic agent; fungal metabolite; mutagen; polar aprotic solvent
glyoxal [no description available]	2.25	1	0	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
sarin Sarin: An organophosphorus ester compound that produces potent and irreversible inhibition of cholinesterase. It is toxic to the nervous system and is a chemical warfare agent.. isopropyl methylphosphonofluoridate : A phosphinic ester that is the isopropyl ester of methylphosphonofluoridic acid.. sarin : A racemate composed of equal amounts of (R)- and (S)-sarin. A potent and irreversible inhibitor of acetylcholinesterase that is toxic to the nervous system and is employed as a chemical warfare agent.	2.91	4	0	fluorine molecular entity; phosphinic ester
tert-butylacrylamide tert-butylacrylamide: structure in first source	2.13	1	0
dimethyldioctadecylammonium dimethyldioctadecylammonium: a cationic lipid analog; RN given refers to parent cpd	2.06	1	0
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.97	4	0	alkane
3-hydroxybutanal [no description available]	2.43	2	0
gamma-valerolactone gamma-valerolactone: metabolite of n-hexane; RN given refers to cpd with methyl moiety in position 5. gamma-valerolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a methyl group at position 5. It has been found in the urine samples of humans exposed to n-hexane.	2.21	1	0	butan-4-olide	flavouring agent; human xenobiotic metabolite
succinic anhydride [no description available]	2.6	1	0	cyclic dicarboxylic anhydride; tetrahydrofurandione
maleic anhydride Maleic Anhydrides: Used in copolymerization reactions, in the Diels-Alder(diene)synthesis, in the preparation of resins, pharmaceuticals and agricultural chemicals. It is a powerful irritant and causes burns.. maleic anhydride : A cyclic dicarboxylic anhydride that is the cyclic anhydride of maleic acid.	3.68	9	0	cyclic dicarboxylic anhydride; furans	allergen
glutaric anhydride glutaric anhydride: RN given in first source. glutaric anhydride : A cyclic dicarboxylic anhydride that is oxane which carries oxo groups at positions 2 and 6. It is used as an intermediate in the production of pharmaceuticals, corrosion inhibitors, and polymers (E.g. epoxy polyesters).	2	1	0	cyclic dicarboxylic anhydride; oxanes
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	2.91	3	0	triamino-1,3,5-triazine	xenobiotic metabolite
chlorobenzene [no description available]	2.11	1	0	monochlorobenzenes	solvent
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.98	4	0	cyclohexanols; secondary alcohol	solvent
triethylene glycol dimethacrylate [no description available]	2.02	1	0
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	2.02	1	0	aliphatic nitrile; dinitrile
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	4.43	20	0	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	3.41	7	0	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
furan furan : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing four carbons and one oxygen, with formula C4H4O. It is a toxic, flammable, low-boiling (31degreeC) colourless liquid.	2.02	1	0	furans; mancude organic heteromonocyclic parent; monocyclic heteroarene	carcinogenic agent; hepatotoxic agent; Maillard reaction product
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	4.27	17	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n,n'-methylenebisacrylamide [no description available]	2.81	3	0
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.07	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
1,4-butanediol butane-1,4-diol : A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16degreeC) with a high boiling point (230degreeC), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).	1.98	1	0	butanediol; glycol	neurotoxin; prodrug; protic solvent
1-hexanol 1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.	2.01	1	0	hexanol; primary alcohol	alarm pheromone; antibacterial agent; fragrance; plant metabolite
diethylenetriamine diethylenetriamine: RN given refers to parent cpd	2.6	1	0	polyazaalkane; triamine
diethanolamine diethanolamine: RN given refers to parent cpd. diethanolamine : A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.	2.48	2	0	ethanolamines	human xenobiotic metabolite
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.41	1	0	alkane	plant metabolite; volatile oil component
octylamine octylamine: RN given refers to 1-octylamine. octan-1-amine : An 8-carbon primary aliphatic amine.	2.07	1	0	primary aliphatic amine	metabolite
n-octanethiol octane-1-thiol : An alkanethiol that is octane substituted by a thiol group at position 1.	2.01	1	0	alkanethiol
carbitol carbitol: used as lubricating oil & in braking fluid, structure. diethylene glycol monoethyl ether : A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.	2.52	2	0	diether; glycol ether; hydroxypolyether; primary alcohol	protic solvent
dodecyltrimethylammonium dodecyltrimethylammonium: used to determine thermal stability of DNA; RN given refers to parent cpd. dodecyltrimethylammonium ion : A quarternary ammonium cation having one dodecyl and three methyl substituents around the central nitrogen.	2.74	3	0	quaternary ammonium ion
triethylene glycol triethylene glycol : A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.	2.31	1	0	diol; poly(ethylene glycol); primary alcohol	plasticiser
dodecylmercaptan dodecylmercaptan: used in polymerization of neoprenes; structure	2.01	1	0
tetraethylenepentamine [no description available]	2.05	1	0	polyazaalkane	copper chelator
neostigmine bromide neostigmine bromide : The bromide salt of neostigmine.	2.01	1	0	bromide salt
phenformin Phenformin: A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). phenformin : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a 2-phenylethyl group. It was used as an anti-diabetic drug but was later withdrawn from the market due to potential risk of lactic acidosis.	2.17	1	0	biguanides	antineoplastic agent; geroprotector; hypoglycemic agent
obidoxime chloride Obidoxime Chloride: Cholinesterase reactivator occurring in two interchangeable isomeric forms, syn and anti.	2.07	1	0
isobutylene 2-methylprop-1-ene : An alkene that is prop-1-ene substituted by a methyl group at position 2.	2.02	1	0	alkene; gas molecular entity
mephobarbital Mephobarbital: A barbiturate that is metabolized to PHENOBARBITAL. It has been used for similar purposes, especially in EPILEPSY, but there is no evidence mephobarbital offers any advantage over PHENOBARBITAL.. mephobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at N-1 by a methyl group and at C-5 by ethyl and phenyl groups.	2.38	2	0	barbiturates	anticonvulsant
ambenonium chloride Ambenonium Chloride: A quaternary ammonium compound that is an inhibitor of cholinesterase activity with actions similar to those of NEOSTIGMINE, but of longer duration. Ambenonium is given by mouth in the treatment of myasthenia gravis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1112). ambenonium chloride : A symmetrical oxalamide-based bis-quaternary ammonium salt having ethyl and 2-chlorobenzyl groups attached to the nitrogens.	2.08	1	0	organic chloride salt; quaternary ammonium salt	EC 3.1.1.8 (cholinesterase) inhibitor; neurotransmitter agent
anthrarufin 1,5-dihydroxyanthraquinone: used in ferric ion sensing as an inclusion complex with beta-cyclodextrin; structure in first source. anthrarufin : A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5.	2.11	1	0	dihydroxyanthraquinone
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2.48	2	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
ortho-hydroxybenzophenone ortho-hydroxybenzophenone: structure in first source. hydroxybenzophenone : Any benzophenone into which is substituted one or more hydroxy groups.	2.11	1	0
2-ethylhexyl salicylate 2-ethylhexyl salicylate: structure given in first source	2.1	1	0	benzoate ester; phenols
ethyl salicylate ethyl salicylate: causes erythema after topical application as an aerosol; found in blood	2.04	1	0	hydroxybenzoic acid
hexachlorobenzene Hexachlorobenzene: An agricultural fungicide and seed treatment agent.. hexachlorobenzene : A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stockholm Convention on Persistent Organic Pollutants.	3.14	5	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
trinitrotoluene Trinitrotoluene: A 2,4,6-trinitrotoluene, which is an explosive chemical that can cause skin irritation and other toxic consequences.. 2,4,6-trinitrotoluene : A trinitrotoluene having the nitro groups at positions 2, 4 and 6.	2.46	2	0	trinitrotoluene	explosive
benzoin [no description available]	3.42	7	0	benzoins; secondary alpha-hydroxy ketone	EC 3.1.1.1 (carboxylesterase) inhibitor
isoquinoline [no description available]	2.07	1	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
2,2'-biquinoline 2,2'-biquinoline: structure in first source	2.01	1	0
arsthinol arsthinol: nanosuspensions of arsthinol could be used for treatment of acute promyelocytic leukaemia	2.08	1	0	acetamides; anilide
anthracene acene : A polycyclic aromatic hydrocarbon consisting of fused benzene rings in a rectilinear arrangement.. acenes : Polycyclic aromatic hydrocarbons consisting of fused benzene rings in a rectilinear arrangement and their substitution derivatives.	3.36	6	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
2-naphthalenesulfonic acid naphthalene-2-sulfonic acid : A naphthalenesulfonic acid in which the sulfo group is linked to position 2 of the naphthalene ring.	2.05	1	0	naphthalenesulfonic acid	environmental contaminant; xenobiotic
2-naphthoxyacetic acid 2-naphthoxyacetic acid: used as plant hormone to promote the growth of roots on clippings, to prevent fruit from falling prematurely; structure	2.75	3	0	naphthyloxyacetic acid
dichlorprop dichlorprop: RN given refers to parent cpd without isomeric designation; structure. 2-(2,4-dichlorophenoxy)propanoic acid : An aromatic ether that is 2-hydroxypropanoic acid in which the hydroxy group at position 2 has been converted to its 2,4-dichlorophenyl ether.. dichlorprop : A racemate comprising equimolar amounts of (R)- and (S)-dichlorprop. It is widely used as a herbicide for killing annual and broad leaf weeds. Only the R-enantiomer has herbicidal activity; the S-enantiomer is inactive.	2	1	0	aromatic ether; dichlorobenzene; monocarboxylic acid
ethyl-p-hydroxybenzoate ethyl-p-hydroxybenzoate: structure	2.1	1	0	ethyl ester; paraben	antifungal agent; antimicrobial food preservative; phytoestrogen; plant metabolite
2,4-dichlorophenol 2,4-dichlorophenol: RN given refers to unlabeled parent+ cpd; structure. 2,4-dichlorophenol : A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.	2.8	3	0	dichlorophenol
2,4-dinitrotoluene 2,4-dinitrotoluene : A dinitrotoluene in which the methyl group is ortho to one of the nitro groups and para to the other. It is the most common isomer of dinitrotoluene.	2.46	2	0	dinitrotoluene
vanillic acid Vanillic Acid: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).. vanillic acid : A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3.	2.1	1	0	methoxybenzoic acid; monohydroxybenzoic acid	plant metabolite
triethylamine [no description available]	2.75	3	0	tertiary amine
cyclonite cyclonite: explosive & convulsant; structure. 1,3,5-trinitro-1,3,5-triazinane : An N-nitro compound that is 1,3,5-triazinane in which all three of the hydrogens attached to the nitrogens have been replaced by nitro groups. It is widely used in both industrial and military explosives.	2.02	1	0	1,3,5-triazinanes; N-nitro compound	explosive
meglumine Meglumine: 1-Deoxy-1-(methylamino)-D-glucitol. A derivative of sorbitol in which the hydroxyl group in position 1 is replaced by a methylamino group. Often used in conjunction with iodinated organic compounds as contrast medium.. N-methylglucamine : A hexosamine that is D-glucitol in which the hydroxy group at position 1 is substituted by the nitrogen of a methylamino group. A crystalline base, it is used in preparing salts of certain acids for use as diagnostic radiopaque media, while its antimonate is used as an antiprotozoal in the treatment of leishmaniasis.	3.56	8	0	hexosamine; secondary amino compound
alpha-naphthylphthalamic acid alpha-naphthylphthalamic acid: RN given refers to parent cpd; structure. naptalam : A dicarboxylic acid monoamide which results from addition of one equivalent of 1-naphthylamine to phthalic anhydride.	2.07	1	0	carboxylic acid; dicarboxylic acid monoamide; N-(1-naphthyl)carboxamide	herbicide
indolebutyric acid indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.	2.02	1	0	indol-3-yl carboxylic acid	auxin; plant hormone; plant metabolite
methyl anthranilate methyl anthranilate : A benzoate ester that is the methyl ester of anthranilic acid.	2.05	1	0	benzoate ester	flavouring agent; metabolite
1-naphthylamine 1-Naphthylamine: A suspected industrial carcinogen (and listed as such by OSHA). Its N-hydroxy metabolite is strongly carcinogenic and mutagenic.. naphthylamine : A primary arylamine that is naphthalene substituted by an amino group at unspecified position.. 1-naphthylamine : A naphthylamine that is naphthalene substituted by an amino group at position 1.	3.32	6	0	naphthylamine	human xenobiotic metabolite
benzil benzil: structure. benzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.	2.02	1	0	alpha-diketone; aromatic ketone
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	2.02	1	0	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	4.13	15	0	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
nitrilotriacetic acid Nitrilotriacetic Acid: A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)	3	4	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
benzyl acetate benzyl acetate : The acetate ester of benzyl alcohol.	2.03	1	0	acetate ester; benzyl ester	metabolite
monuron monuron: minor descriptor (72-83); on-line & Index Medicus search UREA/AA (72-74) & HERBICIDES (72-74) & HERBICIDES UREA (75-83); RN given refers to unlabeled cpd; structure. monuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which one of the nitrogens is substituted by a p-chlorophenyl group while the other is substituted by two methyl groups.	2.5	2	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea; monochlorobenzenes	environmental contaminant; herbicide; xenobiotic
4-tert-octylphenol 4-tert-octylphenol: structure given in first source	2.41	1	0	alkylbenzene
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	2.11	1	0	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	2.72	2	0	monoterpenoid	plant metabolite
n-butyl acrylate butyl acrylate : An acrylate ester obtained by the formal condensation of the hydroxy group of butan-1-ol with the carboxy group of acrylic acid.	2.08	1	0	acrylate ester
ethyl acetate ethyl acetate : The acetate ester formed between acetic acid and ethanol.	2.07	1	0	acetate ester; ethyl ester; volatile organic compound	EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor; metabolite; polar aprotic solvent; Saccharomyces cerevisiae metabolite
mesityl oxide mesityl oxide: solvent for extraction of nitrocellulose, many resins, & tellurium; structure	2.08	1	0	olefinic compound
2,6-diaminopyridine 2,6-diaminopyridine: structure in first source	2.05	1	0
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2.06	1	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
pregnenolone [no description available]	2.96	4	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.61	2	0	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
3-o-methylglucose 3-O-Methylglucose: A non-metabolizable glucose analogue that is not phosphorylated by hexokinase. 3-O-Methylglucose is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems. (J Neurochem 1993;60(4):1498-504). 3-O-methyl-D-glucose : A D-aldohexose that is D-glucose in which the hydrogen of the hydroxy group at position 3 has been substituted by a methyl group. It is a non-metabolisable glucose analogue that is not phosphorylated by hexokinase and is used as a marker to assess glucose transport by evaluating its uptake within various cells and organ systems.	2.4	2	0	D-aldohexose derivative
diphenhydramine hydrochloride Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.	2.44	2	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
ditiocarb Ditiocarb: A chelating agent that has been used to mobilize toxic metals from the tissues of humans and experimental animals. It is the main metabolite of DISULFIRAM.. diethyldithiocarbamic acid : A member of the class of dithiocarbamic acids that is diethylcarbamic acid in which both of the oxygens are replaced by sulfur.	2.43	2	0	dithiocarbamic acids	chelator; copper chelator
2-vanillin ortho-vanillin : A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.	2.43	2	0	benzaldehydes; guaiacols	antimutagen; plant metabolite
aziridine [no description available]	2.5	2	0	azacycloalkane; aziridines; saturated organic heteromonocyclic parent	alkylating agent
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	4.81	30	0	catechin	antioxidant; plant metabolite
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	2.15	1	0	ortho- and peri-fused polycyclic arene
indeno(1,2,3-cd)pyrene indeno(1,2,3-cd)pyrene: structure in first source	2.08	1	0	pyrenes
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	3.73	9	0	ortho- and peri-fused polycyclic arene; perylenes
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.1	1	0	ortho- and peri-fused polycyclic arene
triphenylene triphenylene: structure. triphenylene : An ortho-fused polycyclic arene consisting of four fused benzene rings.	2.25	1	0	ortho-fused polycyclic arene
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	5.14	10	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	3.21	5	0	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	3.26	6	0	indazole
benzoxazoles 1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.	2.69	3	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
1,3-benzodioxole 1,3-benzodioxole : A benzodioxole consisting of a benzene ring substituted by a the methylenedioxy group.	2.08	1	0	benzodioxole
azulene [no description available]	2.02	1	0	azulenes; mancude carbobicyclic parent; ortho-fused bicyclic arene	plant metabolite; volatile oil component
adamantane Adamantane: A tricyclo bridged hydrocarbon.	7.35	128	0	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	4.27	17	0	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	3.57	8	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	3.62	9	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	7.69	46	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	2.52	2	0	diazine; pyrazines	Daphnia magna metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	2.01	1	0	organic cation
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	4.41	21	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
2-ethylhexanoic acid tin(ii) salt 2-ethylhexanoic acid tin(II) salt: used as a catalyst for ring-opening polymerization to make D,L-lactide and epsilon-caprolactone copolymers	2.05	1	0
hydrazine diamine : Any polyamine that contains two amino groups.	2.5	2	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
paraoxon [no description available]	3.19	5	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
hemicholinium 3 Hemicholinium 3: A potent inhibitor of the high affinity uptake system for CHOLINE. It has less effect on the low affinity uptake system. Since choline is one of the components of ACETYLCHOLINE, treatment with hemicholinium can deplete acetylcholine from cholinergic terminals. Hemicholinium 3 is commonly used as a research tool in animal and in vitro experiments.	2.1	1	0
dexamethasone 21-phosphate dexamethasone 21-phosphate: has anti-inflammatory activity. dexamethasone phosphate : A steroid phosphate that is the 21-O-phospho derivative of dexamethasone.	4.33	1	1	11beta-hydroxy steroid; 17-hydroxy steroid; 3-oxo-Delta(4) steroid; fluorinated steroid; steroid phosphate; tertiary alpha-hydroxy ketone	glucocorticoid receptor agonist
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	2.07	1	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
3,5-dichlorosalicylic acid 3,5-dichlorosalicylic acid: structure in first source	2.02	1	0	chlorobenzoic acid
5-chlorosalicylic acid 5-chlorosalicylic acid: major metabolite of meseclazone; RN given refers to parent cpd. 5-chlorosalicylic acid : A monohydroxybenzoic acid that is 2-hydroxybenzoic acid (salicylic acid) in which the hydrogen at position 5 is replaced by chlorine.	2.02	1	0	chlorobenzoic acid; monochlorobenzenes; monohydroxybenzoic acid
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	3.2	5	0	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	2.03	1	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
aminoimidazole carboxamide Aminoimidazole Carboxamide: An imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.. 5-aminoimidazole-4-carboxamide : An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.	2.03	1	0	aminoimidazole; monocarboxylic acid amide	mouse metabolite
methysergide Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.	2.15	1	0	ergoline alkaloid
betamethasone Betamethasone: A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)	2.66	3	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent
hexafluorobenzene [no description available]	2.48	2	0	fluorobenzenes; fluorocarbon	NMR chemical shift reference compound
silicon carbide silicon carbide: fibers used for reinforcement of porcelain crowns; a feldspathic body (gingival) porcelain; used to coat titanium hip prostheses	2.11	1	0	organosilicon compound
cyproterone acetate [no description available]	2.11	1	0	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; chlorinated steroid; steroid ester	androgen antagonist; geroprotector; progestin
lithocholic acid Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.. lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.. lithocholate : A bile acid anion that is the conjugate base of lithocholic acid.	3.13	5	0	bile acid; C24-steroid; monohydroxy-5beta-cholanic acid	geroprotector; human metabolite; mouse metabolite
nandrolone Nandrolone: C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of ESTRADIOL to resemble TESTOSTERONE but less one carbon at the 19 position.. nandrolone : A 3-oxo Delta(4)-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.	2.04	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid	human metabolite
ethylamphetamine ethylamphetamine: RN given refers to parent cpd with unspecified isomeric designation; see also record for d-N-ethylamphetamine	2.07	1	0	amphetamines
cyanogen cyanogen: structure. oxalonitrile : A dinitrile that is ethane substituted by two cyano groups.	2.21	1	0	dinitrile; pseudohalogen
hydantoins Hydantoins: Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS.. imidazolidine-2,4-dione : An imidazolidinone with oxo groups at position 2 and 4.	2.68	3	0	imidazolidine-2,4-dione
fluorobenzenes Fluorobenzenes: Derivatives of BENZENE that contain FLUORINE.. monofluorobenzene : The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.. fluorobenzenes : Any fluoroarene that is a benzene or a substituted benzene carrying at least one fluoro group.	4.97	8	1	monofluorobenzenes	NMR chemical shift reference compound
chlorfenvinphos Chlorfenvinphos: An organophosphorus cholinesterase inhibitor that is used as an insecticide and an acaricide.	2.04	1	0	dichlorobenzene; organic phosphate; organochlorine acaricide; organochlorine insecticide; organophosphate insecticide	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
limestone Calcium Carbonate: Carbonic acid calcium salt (CaCO3). An odorless, tasteless powder or crystal that occurs in nature. It is used therapeutically as a phosphate buffer in hemodialysis patients and as a calcium supplement.. calcium carbonate : A calcium salt with formula CCaO3.	2.97	4	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
chenodeoxycholic acid Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.. chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.. chenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.	3.26	6	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
glycocholic acid Glycocholic Acid: The glycine conjugate of CHOLIC ACID. It acts as a detergent to solubilize fats for absorption and is itself absorbed.. glycocholic acid : A bile acid glycine conjugate having cholic acid as the bile acid component.. glycocholate : A cholanic acid conjugate anion that is the conjugate base of glycocholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.45	2	0	bile acid glycine conjugate	human metabolite
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA.	2.03	1	0
rhein [no description available]	3.05	4	0	dihydroxyanthraquinone
berbamine [no description available]	2.11	1	0	phenylpropanoid
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	2.75	3	0	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
imperatorin imperatorin: tumor necrosis factor antagonist; furanocoumarin from West African medicinal plant Clausena anisata; structure in Negwer, 5th ed, #3005. imperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.06	1	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
osthol osthol: from Cnidium monnieri and Angelica pubescens (both Apiaceae); structure given in first source	2.03	1	0	botanical anti-fungal agent; coumarins	metabolite
9-phenanthrol 9-phenanthrol: an inhibitor of AMP-dependent protein kinase catalytic subunit; structure in first source. 9-phenanthrol : A phenanthrol that is phenanthrene in which a hydrogen attached to a carbon in the central ring has been replaced by a hydroxy group.	2.05	1	0	phenanthrol	TRPM4 channel inhibitor
ninhydrin Ninhydrin: 2,2-Dihydroxy-1H-indene-1,3-(2H)-dione. Reagent toxic to skin and mucus membranes. It is used in chemical assay for peptide bonds, i.e., protein determinations and has radiosensitizing properties.. ninhydrin : A member of the class of indanones that is indane-1,3-dione bearing two additional hydroxy substituents at position 2.	2.05	1	0	aromatic ketone; beta-diketone; indanones; ketone hydrate	colour indicator; human metabolite
9-fluorenone fluoren-9-one : The simplest member of the class fluoren-9-ones that is 9H-fluorene bearing an oxo substituent at position 9.	2.03	1	0	fluoren-9-ones	fungal xenobiotic metabolite
salicylurate salicylurate: RN given refers to parent cpd. salicyluric acid : An N-acylglycine in which the acyl group is specified as 2-hydroxybenzoyl.. salicylurate : A monocarboxylic acid anion that is the conjugate base of salicyluric acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	3.79	2	1	N-acylglycine; secondary carboxamide	human xenobiotic metabolite; uremic toxin
kainic acid Kainic Acid: (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose.	2.05	1	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
thymoquinone thymoquinone: constituent of cedarwood; can cause dermatitis; structure. thymoquinone : A member of the class of 1,4-benzoquinones that is 1,4-bezoquinone in which the hydrogens at positions 2 and 5 are replaced by methyl and isopropyl groups, respectively. It is a natural compound isolated from Nigella sativa which has demonstrated promising chemotherapeutic activity.	2.08	1	0	1,4-benzoquinones	adjuvant; anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; cardioprotective agent; plant metabolite
hydratropic acid hydratropic acid: RN given refers to cpd without isomeric designation; structure. hydratropic acid : A 2-arylpropionic acid carrying a phenyl group at position 2. It is a metabolite of alpha-methylstyrene (AMS), a volatile hydrocarbon.	2.5	2	0	2-arylpropionic acid	human xenobiotic metabolite
phenylpropanolamine Phenylpropanolamine: A sympathomimetic that acts mainly by causing release of NOREPINEPHRINE but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.. phenylpropanolamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group. A decongestant and appetite suppressant, it is commonly used in prescription and over-the-counter cough and cold preparations.. (-)-norephedrine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid.	2.74	3	0	amphetamines; phenethylamine alkaloid	plant metabolite
melarsoprol Melarsoprol: Arsenical used in trypanosomiases. It may cause fatal encephalopathy and other undesirable side effects.	2.46	2	0	triazines
dithiol dithiol: structure	2.01	1	0
sodium carbonate sodium carbonate: used topically for dermatitides, mouthwash, vaginal douche; veterinary use as emergency emetic; RN given refers to carbonic acid, di-Na salt; structure	2.52	2	0	carbonate salt; organic sodium salt
2-norbornene norbornene : A bridged compound that is cyclohexane with a methylene bridge between carbons 1 and 4 and a double bond at position 2.	2	1	0
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	4.52	20	0	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
dipicolinic acid dipicolinic acid : A pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6.	2.46	2	0	pyridinedicarboxylic acid	bacterial metabolite
phenylcarbamic acid [no description available]	2.72	3	0	amino acid
4-hydroxyphenylethanol 4-hydroxyphenylethanol: in chest gland secretion of galagos. 2-(4-hydroxyphenyl)ethanol : A phenol substituted at position 4 by a 2-hydroxyethyl group.	3.08	4	0	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent
caprolactone hexano-6-lactone : A epsilon-lactone that is oxepane substituted by an oxo group at position 2.	3.18	5	0	epsilon-lactone
oxetane oxetane: structure. oxetane : A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.	2.03	1	0	oxetanes; saturated organic heteromonocyclic parent
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	4.94	8	1
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	3.92	12	0	thiazolidine
arachidic acid icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
hexacosanoic acid hexacosanoic acid: a C(26) saturated acid. hexacosanoic acid : A 26-carbon, straight-chain, saturated fatty acid.	2.05	1	0	fatty acid 26:0; straight-chain saturated fatty acid; very long-chain fatty acid
thioacetic acid ethanethioic S-acid : A thioacetic acid that is acetic acid in which the oxygen atom of the hydroxy group has been replaced by a sulfur atom.	2.31	1	0	thioacetic acid
oleanolic acid [no description available]	4.22	16	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
dihydroergotamine Dihydroergotamine: A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.. dihydroergotamine : Ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension.	3.38	1	1	ergot alkaloid; semisynthetic derivative	dopamine agonist; non-narcotic analgesic; serotonergic agonist; sympatholytic agent; vasoconstrictor agent
dithiazanine Dithiazanine: 3-Ethyl-2-(5-(3-ethyl-2-benzothiazolinylidene)-1,3- pentadienyl)benzothiazolium. A benzothiazole that was formerly used as an antinematodal agent and is currently used as a fluorescent dye.. dithiazanine : A cationic C3-cyanine dye with 3-ethylbenzothiazol-2-yl groups at both ends.	2.03	1	0	benzothiazoles; benzothiazolium ion	anthelminthic drug; fluorochrome
myrtenol myrtenol: fragrance ingredient; structure in first source	2.25	1	0
hematoxylin Hematoxylin: A dye obtained from the heartwood of logwood (Haematoxylon campechianum Linn., Leguminosae) used as a stain in microscopy and in the manufacture of ink.	2.05	1	0	organic heterotetracyclic compound; oxacycle; polyphenol; tertiary alcohol	histological dye; plant metabolite
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.59	2	0	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	4.06	5	0	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	1.97	1	0	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	3.6	8	0
angelicin angelicin: used as tranquillizer; sedative; or anticonvulsant; structure	2.46	2	0	furanocoumarin
1,2-naphthoquinone naphthalene-1,2-dione: structure given in first source. 1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.	2.03	1	0	1,2-naphthoquinones	aryl hydrocarbon receptor agonist; carcinogenic agent
flavone flavone: RN given refers to unlabeled cpd; structure given in first source. flavone : The simplest member of the class of flavones that consists of 4H-chromen-4-one bearing a phenyl substituent at position 2.	2.17	1	0	flavones	metabolite; nematicide
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.39	2	0	organic molecular entity
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	3.29	6	0	C-nitro compound; imidazoles	antitubercular agent
cellobiose beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.	2.42	2	0	cellobiose	epitope
tetralol tetralol: structure	2.02	1	0
tropolone Tropolone: A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).. tropolone : A cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii.	2.15	1	0	alpha-hydroxy ketone; cyclic ketone; enol	bacterial metabolite; fungicide; toxin
4-toluenesulfinic acid 4-toluenesulfinic acid: RN given refers to parent cpd	1.99	1	0
perillyl alcohol perillyl alcohol: inhibits geranylgeranyl transferase; structure in first source. perillyl alcohol : A limonene monoterpenoid consists of a cyclohexene ring substituted by a hydroxymethyl and a prop-1-en-2-yl group at positions 1 and 4 respectively. It is a constituent of a variety of essential oils including lavender.	2.11	1	0	limonene monoterpenoid	plant metabolite; volatile oil component
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	3.29	6	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
tricaprylin tricaprylin: 13C-labeled trioctanoin used in breath tests to detect fat malabsorption. trioctanoin : A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.	2.07	1	0	octanoate ester; triglyceride	anticonvulsant; plant metabolite
dicyclohexylcarbodiimide 1,3-dicyclohexylcarbodiimide : A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.	2.02	1	0	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent
maleimide [no description available]	2.15	1	0	dicarboximide; maleimides	EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
muscone muscone: structure in first source	2.02	1	0
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	5.26	6	2	dialdehyde	biomarker
myristic acid Myristic Acid: A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). tetradecanoic acid : A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.. tetradecanoate : A long-chain fatty acid anion that is the conjugate base of myristic acid; major species at pH 7.3.	2.73	3	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite
n-hexadecane n-hexadecane: structure. hexadecane : A straight-chain alkane with 16 carbon atoms. It is a component of essential oil isolated from long pepper.	2.75	3	0	long-chain alkane	non-polar solvent; plant metabolite; volatile oil component
magnesium carbonate magnesium carbonate: RN given refers to parent cpd (1:1). magnesium carbonate : A magnesium salt with formula CMgO3. Its hydrated forms, particularly the di-, tri-, and tetrahydrates occur as minerals.	2.04	1	0	carbonate salt; magnesium salt; one-carbon compound; organic magnesium salt	antacid; fertilizer
methyl lactate methyl lactate: RN given refers to cpd without isomeric designation. methyl 2-hydroxypropionate : A lactate ester resulting from the formal condensation of the carboxy group of 2-hydroxypropanoic acid with methanol.	2.04	1	0	lactate ester; methyl ester	metabolite
trinitrobenzenesulfonic acid Trinitrobenzenesulfonic Acid: A reagent that is used to neutralize peptide terminal amino groups.. 2,4,6-trinitrobenzenesulfonic acid : The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.	2.74	3	0	arenesulfonic acid; C-nitro compound	epitope; explosive; reagent
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	2.03	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
violacein [no description available]	2.01	1	0
lucanthone hydrochloride Schistosomicides: Agents that act systemically to kill adult schistosomes.	2.45	2	0
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	3.19	5	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
resazurin resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure	2.54	2	0	phenoxazine
paeonol paeonol: structure	3.43	7	0	methoxybenzenes; phenols	metabolite
hematoporphyrin Hematoporphyrins: Iron-free derivatives of heme with 4 methyl groups, 2 hydroxyethyl groups and 2 propionic acid groups attached to the pyrrole rings. Some of these PHOTOSENSITIZING AGENTS are used in the PHOTOTHERAPY of malignant NEOPLASMS.. hematoporphyrin : A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups.	2.25	1	0
neutral red Neutral Red: A vital dye used as an indicator and biological stain. Various adverse effects have been observed in biological systems.. neutral red : A hydrochloride obtained by combining the free base of neutral red with one equivalent of hydrochloric acid. Neutral red acts as a pH indicator, changing from red to yellow between pH 6.8 and 8.0.	2.06	1	0	hydrochloride	acid-base indicator; dye; two-colour indicator
4,4'-bipyridyl 4,4'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-4 and C-4'.	2.45	2	0	bipyridine
3-nitrophenol [no description available]	2.57	2	0	3-nitrophenols
tristearin tristearoylglycerol : A triglyceride that is glycerol in which all three hydroxy groups have been formally esterified with stearic acid.	3.14	5	0	triacylglycerol 54:0	Caenorhabditis elegans metabolite; plant metabolite
tripalmitin tripalmitin: structure. tripalmitin : A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by palmitic (hexadecanoic) acid.	2.15	1	0	triglyceride
2,6-nonadienal [no description available]	2.11	1	0
malachite green malachite green: RN given refers to parent cpd; structure. malachite green : An organic chloride salt that is the monochloride salt of malachite green cation. Used as a green-coloured dye, as a counter-stain in histology, and for its anti-fungal properties in aquaculture.	2.66	2	0	organic chloride salt	antibacterial agent; antifungal drug; carcinogenic agent; environmental contaminant; fluorochrome; histological dye; teratogenic agent
congo red Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS.. Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0.	3.19	5	0	bis(azo) compound
docusate Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.	2.95	4	0	diester; organosulfonic acid
3-hydroxyflavone 3-hydroxyflavone: structure given in first source. flavonol : A monohydroxyflavone that is the 3-hydroxy derivative of flavone.	3.48	7	0	flavonols; monohydroxyflavone
2-naphthylacetic acid 2-naphthylacetic acid: RN given refers to parent cpd. 2-naphthylacetic acid : A naphthylacetic acid carrying a carboxy group at position 2.	2.07	1	0	naphthylacetic acid
potassium carbonate potassium carbonate : A potassium salt that is the dipotassium salt of carbonic acid.	2.47	2	0	carbonate salt; potassium salt	catalyst; fertilizer; flame retardant
allethrins Allethrins: Synthetic analogs of the naturally occurring insecticides cinerin, jasmolin, and pyrethrin. (From Merck Index, 11th ed)	2.78	3	0	cyclopropanecarboxylate ester	pyrethroid ester insecticide
toluene 2,4-diisocyanate Toluene 2,4-Diisocyanate: Skin irritant and allergen used in the manufacture of polyurethane foams and other elastomers.. toluene 2,4-diisocyanate : A toluene meta-diisocyanate in which the isocyanato groups are at positions 2 and 4 relative to the methyl group on the benzene ring.	2.01	1	0	toluene meta-diisocyanate	allergen; hapten
diphenylamine Diphenylamine: In humans it may be irritating to mucous membranes. Methemoglobinemia has been produced experimentally. In veterinary use, it is one of active ingredients in topical agents for prevention and treatment of screwworm infestation. An indicator in tests for nitrate poisoning.. diphenylamine : An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.	2.75	3	0	aromatic amine; bridged diphenyl fungicide; secondary amino compound	antifungal agrochemical; antioxidant; carotogenesis inhibitor; EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor; ferroptosis inhibitor; radical scavenger
4-methylcyclohexanol 4-methylcyclohexanol: RN given refers to cpd without isomeric designation	2.31	1	0
3-methoxybenzaldehyde 3-methoxybenzaldehyde : A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.	2.04	1	0	benzaldehydes; monomethoxybenzene	Brassica napus metabolite
allyl sulfide allyl sulfide: essence of garlic; inhibits CYP2E1	2.8	3	0	organic sulfide
glycopyrrolate Glycopyrrolate: A muscarinic antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics.. glycopyrronium bromide : A quaternary ammonium salt composed of 3-{[cyclopentyl(hydroxy)phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium and bromide ions in a 1:1 ratio.	2.1	1	0	organic bromide salt; quaternary ammonium salt
2-bromopropionic acid, (dl)-isomer 2-bromopropionic acid: RN given refers to cpd without isomeric designation	2.21	1	0
(s)-binol (1,1'-binaphthalene)-2,2'-diol: structure in first source	2	1	0	naphthols
triphenylphosphine triphenylphosphine: RN given refers to parent cpd. triphenylphosphine : A member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.	2.01	1	0	benzenes; tertiary phosphine	NMR chemical shift reference compound; reducing agent
3,5-dinitrosalicylic acid 3,5-dinitrosalicylic acid: RN given refers to parent cpd. 3,5-dinitrosalicylic acid : A monohydroxybenzoic acid consisting of 2-hydroxybenzoic acid having nitro substituents at the 3- and 5-positions. It is used in colorimetric testing for the presence of free carbonyl groups (C=O) in reducing sugars.	2.02	1	0	C-nitro compound; monohydroxybenzoic acid	hapten
2,4-dinitrobenzoic acid [no description available]	2.1	1	0
phenacylamine phenacylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #6990	2.1	1	0	aromatic ketone
methyl carbonate methyl carbonate: RN given refers to unlabeled parent cpd; structure. dimethyl carbonate : A carbonate ester that is carbonic acid in which both hydrogens are replaced by methyl groups. A flammable, colourless liquid (m.p. 2-4degreeC, b.p. 90degreeC) with a characterstic ester-like odour, it is used as a 'green' methylating agent and as a solvent.	2.52	2	0	carbonate ester	reagent; solvent
2-pyrrolidone 2-pyrrolidone: RN given refers to parent cpd. pyrrolidin-2-one : The simplest member of the class of pyrrolidin-2-ones, consisting of pyrrolidine in which the hydrogens at position 2 are replaced by an oxo group. The lactam arising by the formal intramolecular condensation of the amino and carboxy groups of gamma-aminobutyric acid (GABA).	2.04	1	0	pyrrolidin-2-ones	metabolite; polar solvent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	3.39	6	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
4-cyanobenzoic acid [no description available]	2.03	1	0
4,4'-diaminodibenzyl 4,4'-diaminodibenzyl: RN given refers to parent cpd	2.01	1	0
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	3.01	4	0
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	3.16	5	0	cyclic ketone; erythromycin
2'-deoxy-5'-adenosine monophosphate 2'-deoxy-5'-adenosine monophosphate: RN given refers to parent cpd. 2'-deoxyadenosine 5'-monophosphate : A purine 2'-deoxyribonucleoside 5'-monophosphate having adenine as the nucleobase.	2.15	1	0	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-monophosphate	fundamental metabolite
homoserine homoserine : An alpha-amino acid that is glycine substituted at the alpha-position by a 2-hydroxyethyl group.. L-homoserine : The L-enantiomer of homoserine.	2.13	1	0	amino acid zwitterion; homoserine	algal metabolite; Escherichia coli metabolite; human metabolite; Saccharomyces cerevisiae metabolite
2-piperidone 2-piperidone: structure given in first source. piperidin-2-one : A delta-lactam that is piperidine which is substituted by an oxo group at position 2.	2.17	1	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
2,6-dichlorobenzoquinone 2,6-dichlorobenzoquinone : A member of the class of 1,4-benzoquinones that is p-benzoquinone in which the hydrogens at positions 2 and 6 have been replaced by chlorines. A highly toxic and carcinogenic disinfection by-product found in drinking water.	2.03	1	0	1,4-benzoquinones; organochlorine compound	carcinogenic agent; poison
phenylphosphate phenylphosphate: structure given in first source. phenyl phosphate : An aryl phosphate resulting from the mono-esterification of phosphoric acid with phenol.	2.02	1	0	aryl phosphate	mouse metabolite
decan-4-olide gamma-decalactone : A gamma-lactone that is oxolan-2-one substituted by a hexyl group at position 5.	1.99	1	0	gamma-lactone; tetrahydrofuranone	anticonvulsant; flavouring agent; food additive
2-amino-4,6-dimethyl pyrimidine 2-amino-4,6-dimethyl pyrimidine: structure in first source	2.01	1	0	aminopyrimidine
o,p'-ddt o,p'-DDT: RN given refers to cpd without isomeric designation.	2.07	1	0	diarylmethane
levonorgestrel Levonorgestrel: A synthetic progestational hormone with actions similar to those of PROGESTERONE and about twice as potent as its racemic or (+-)-isomer (NORGESTREL). It is used for contraception, control of menstrual disorders, and treatment of endometriosis.	2.43	2	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin; synthetic oral contraceptive
2-nonanone 2-nonanone: RN given refers to cpd with locant for oxo moiety in position 2. nonanone : Any ketone that is nonane substituted by an oxo group at unspecified position.. nonan-2-one : A methyl ketone that is nonane in which the methylene hydrogens at position 2 are replaced by an oxo group.	2.13	1	0	methyl ketone	plant metabolite
1,6-hexamethylene diisocyanate hexamethylene diisocyanate : A diisocyanate compound with the two isocyanates linked by a hexane-1,6-diyl group.	3.01	4	0	diisocyanate	allergen; hapten
adamantanecarboxylic acid [no description available]	3.29	6	0
4-nitrophenyl acetate [no description available]	2.42	2	0	C-nitro compound; phenyl acetates
boldenone boldenone: RN given refers to (17beta)-isomer. boldenone : An 3-oxo-Delta(1),Delta(4)-steroid substituted by an oxo group at position 3 and a beta-hydroxy group at position 17. It is an anabolic androgenic steroid that has been developed for veterinary use.	1.97	1	0	17beta-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; anabolic androgenic steroid
turinabol turinabol: RN given refers to (17beta)-isomer; do not confuse with related record for turinabol-oral	2.41	1	0	steroid ester
hydroxyethyl methacrylate hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.	2.48	2	0	enoate ester	allergen; polymerisation monomer
2-chloroethylamine [no description available]	2.07	1	0
n-methylpyrrolidone 1-methylpyrrolidin-2-one: structure in first source. N-methylpyrrolidin-2-one : A member of the class of pyrrolidine-2-ones that is pyrrolidin-2-one in which the hydrogen attached to the nitrogen is replaced by a methyl group.	2.45	2	0	lactam; N-alkylpyrrolidine; pyrrolidin-2-ones	polar aprotic solvent
1,4-androstadiene-3,17-dione 1,4-androstadiene-3,17-dione: structure. androsta-1,4-diene-3,17-dione : A steroid that consists of androstane having double bonds at positions 1 and 4 and two keto groups at positions 3 and 17.	2.03	1	0	17-oxo steroid; 3-oxo-Delta(1) steroid; 3-oxo-Delta(4) steroid
benzoylarginine nitroanilide Benzoylarginine Nitroanilide: A chromogenic substrate that permits direct measurement of peptide hydrolase activity, e.g., papain and trypsin, by colorimetry. The substrate liberates p-nitroaniline as a chromogenic product.	2.08	1	0
amaranth dye Amaranth Dye: A sulfonic acid-based naphthylazo dye used as a coloring agent for foodstuffs and medicines and as a dye and chemical indicator. It was banned by the FDA in 1976 for use in foods, drugs, and cosmetics. (From Merck Index, 11th ed)	2.6	1	0
4-phenylpyridine [no description available]	2.02	1	0	phenylpyridine
2-phenoxypropanoic acid 2-phenoxypropanoic acid: structure in first source	2.42	2	0	aromatic ether; carboxylic acid
1,2,3,4-tetrahydrocarbazole 1,2,3,4-tetrahydrocarbazole: structure in first source	2	1	0
methylparaoxon [no description available]	2.21	1	0	C-nitro compound
deoxycytidine [no description available]	2.21	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxyuridine [no description available]	2.04	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
azure a Azure A: RN given refers to chloride. azure A : An organic chloride salt having 3-amino-7-(dimethylamino)phenothiazin-5-ium as the counterion. It is used in making azure eosin stains for blood smear staining.	2.01	1	0
canrenone Canrenone: A synthetic pregnadiene compound with anti-aldosterone activity.	3.38	1	1	steroid lactone
rhodamine 6g rhodamine 6G: RN given refers to HCl	2.79	3	0
bucrylate Bucrylate: Cyanoacrylate tissue adhesive also used to occlude blood vessels supplying neoplastic or other diseased tissue.	1.99	1	0
ethambutol Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.	2.25	1	0	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
phenylglyoxal [no description available]	2.02	1	0	phenylacetaldehydes
pyrithioxin Pyrithioxin: A neurotropic agent which reduces permeability of blood-brain barrier to phosphate. It has no vitamin B6 activity.	2.03	1	0	methylpyridines
tetradecyltrimethylammonium tetradecyltrimethylammonium: cationic surfactant; used to determine thermal stability of DNA; Catrimox-14 is the tradename of the oxalate; Catrimox-14 lyses cells and simultaneously precipitates RNA and was demonstrated useful in isolating RNA from whole blood	2.11	1	0
undecane undecane : A straight-chain alkane with 11 carbon atoms.	1.98	1	0	alkane
1,3-propane sultone 1,3-propane sultone: sultone is usually defined as a derivative of 1,8-naphtholsulfonic acid; structure	2.02	1	0	sultone
tetramethylpyrazine tetramethylpyrazine: found in Ligusticum chuanxiong. tetramethylpyrazine : A member of the class of pyrazines that is pyrazine in which all four hydrogens have been replaced by methyl groups. An alkaloid extracted from Chuanxiong (Ligusticum wallichii).	2.07	1	0	alkaloid; pyrazines	antineoplastic agent; apoptosis inhibitor; bacterial metabolite; neuroprotective agent; platelet aggregation inhibitor; vasodilator agent
4-hydroxybenzophenone 4-hydroxybenzophenone: RN given refers to parent cpd	2.08	1	0	benzophenones
pyrovalerone pyrovalerone: RN given refers to parent cpd; synonyms F 1983 & Centroton refer to HCl; structure	2.21	1	0	aromatic ketone
decabromobiphenyl ether decabromobiphenyl ether: a flame retardant. decabromodiphenyl ether : A polybromodiphenyl ether that is diphenyl ether in which all of the hydrogens have been replaced by bromines.	2.48	2	0	polybromodiphenyl ether	neurotoxin
4-aminothiophenol [no description available]	2.21	1	0
carmine Carmine: Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker.	2.11	1	0
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	4.08	13	0
cadmium sulfide [no description available]	2.99	4	0	cadmium molecular entity
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	3.31	6	0	alkali metal hydroxide
manganese dioxide [no description available]	2.17	1	0	manganese molecular entity; metal oxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	5.3	15	0	zinc molecular entity
molybdenum disulfide [no description available]	2.61	2	0	sulfide salt
cupric sulfide copper(II) sulfide : A copper sulfide in which the metal is in the +2 oxidation state.	2.03	1	0
arsenic trioxide Arsenic Trioxide: An inorganic compound with the chemical formula As2O3 that is used for the treatment of ACUTE PROMYELOCYTIC LEUKEMIA in patients who have relapsed from, or are resistant to, conventional drug therapy.	2.08	1	0
ammonium hydroxide Ammonium Hydroxide: The hydroxy salt of ammonium ion. It is formed when AMMONIA reacts with water molecules in solution.. ammonium hydroxide : A solution of ammonia in water.	2.02	1	0	inorganic hydroxy compound	food acidity regulator
ferrous oxide [no description available]	2.17	1	0	iron oxide
vancomycin Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.	3.76	10	0	glycopeptide	antibacterial drug; antimicrobial agent; bacterial metabolite
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	3.2	5	0	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	4.54	23	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
tocopherols [no description available]	3.04	4	0
selenomethionine [no description available]	2	1	0	selenoamino acid; selenomethionines	plant metabolite
9,10-diphenylanthracene [no description available]	2.13	1	0	anthracenes	fluorochrome; photosensitizing agent
dodecylsulfonic acid dodecylsulfonic acid: RN given refers to parent cpd	2.05	1	0	organosulfonic acid
bisphenol a-glycidyl methacrylate Bisphenol A-Glycidyl Methacrylate: The reaction product of bisphenol A and glycidyl methacrylate that undergoes polymerization when exposed to ultraviolet light or mixed with a catalyst. It is used as a bond implant material and as the resin component of dental sealants and composite restorative materials.	2.02	1	0	diarylmethane
1-aminopyrene [no description available]	2.08	1	0
butanesultone [no description available]	2.41	2	0
spectinomycin Spectinomycin: An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of GONORRHEA.. spectinomycin dihydrochloride : A hydrochloride obtained by combining spectinomycin with two molar equivalents of hydrochloric acid. An antibiotic that is active against gram-negative bacteria and used (as its pentahydrate) to treat gonorrhea.. spectinomycin : A pyranobenzodioxin and antibiotic that is active against gram-negative bacteria and used (as its dihydrochloride pentahydrate) to treat gonorrhea. It is produced by the bacterium Streptomyces spectabilis.	2.1	1	0	cyclic acetal; cyclic hemiketal; cyclic ketone; pyranobenzodioxin; secondary alcohol; secondary amino compound	antibacterial drug; antimicrobial agent; bacterial metabolite
laudanosine laudanosine: opium alkaloid	2.11	1	0	isoquinolines
1,2,3,4-butanetetracarboxylic acid 1,2,3,4-butanetetracarboxylic acid: structure in first source	2.31	1	0
decane decane : A straight-chain alkane with 10 carbon atoms.	2.01	1	0	alkane
1,2-dimethylimidazole [no description available]	2.05	1	0	imidazoles
tetrafluoroterephthalonitrile tetrafluoroterephthalonitrile: can cause contact dermatitis; structure given in first source	2.63	2	0
stearylamine stearylamine: RN given refers to parent cpd. octadecan-1-amine : An 18-carbon primary aliphatic amine.	2.05	1	0	primary aliphatic amine	film-forming compound
ethyldimethylaminopropyl carbodiimide Ethyldimethylaminopropyl Carbodiimide: Carbodiimide cross-linking reagent.	2.21	1	0
tetrachloroisophthalonitrile tetrachloroisophthalonitrile: structure. chlorothalonil : A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.	2.53	2	0	aromatic fungicide; dinitrile; tetrachlorobenzene	antifungal agrochemical
paraquat Paraquat: A poisonous dipyridilium compound used as contact herbicide. Contact with concentrated solutions causes irritation of the skin, cracking and shedding of the nails, and delayed healing of cuts and wounds.. paraquat : An organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions.	3.03	4	0	organic cation	geroprotector; herbicide
pristane pristane: structure. pristane : A norterpene that is an acyclic saturated hydrocarbon derived from phytane by loss of its C-16 terminal methyl group.	1.97	1	0	long-chain alkane; norterpene	biomarker; immunological adjuvant
s,n,n'-tripropylthiocarbamate Reward: An object or a situation that can serve to reinforce a response, to satisfy a motive, or to afford pleasure.. vernolate : A monounsaturated fatty acid anion that is the conjugate base of vernolic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	2.97	1	0	tertiary amine
orange g orange G : An organic sodium salt that is the disodium salt of 7-hydroxy-8-[(E)-phenyldiazenyl]naphthalene-1,3-disulfonic acid. It is often combined with other yellow dyes in alcoholic solution to stain erythrocytes in trichrome methods, and is used for demonstrating cells in the pancreas and pituitary.	2.44	2	0
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	3.13	5	0	quaternary ammonium ion
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2.66	2	0	hydroquinones	food antioxidant
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	4.45	8	0	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
amiloride Amiloride: A pyrazine compound inhibiting SODIUM reabsorption through SODIUM CHANNELS in renal EPITHELIAL CELLS. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with DIURETICS to spare POTASSIUM loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705). amiloride : A member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid.	3.65	9	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
pyronine b pyronine B: Merck as dimer with 2(FeCl3); RN given refers to chloride. pyronin B : An organic chloride salt having 6-(diethylamino)-N,N-diethyl-3H-xanthen-3-iminium as the cation. Depending on the mode of manufacture, pyronin B also exists in the form of an FeCl3 complex.	2.02	1	0	iminium salt; organic chloride salt	histological dye
n-isopropylacrylamide N-isopropylacrylamide: can polymerize with glycidyl acrylate to form reactive water-soluble polymer that can react with the amino groups of enzymes-proteins or other ligands	3.9	11	0
fluorescein Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.	3.76	10	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
methylprednisolone hemisuccinate Methylprednisolone Hemisuccinate: A water-soluble ester of METHYLPREDNISOLONE used for cardiac, allergic, and hypoxic emergencies.	2.51	2	0	corticosteroid hormone; hemisuccinate
thioflavin t thioflavin T: RN given refers to chloride; structure. thioflavine T : An organic chloride salt having 2-[4-(dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium as the counterion. It is widely used to visualise and quantify the presence of amyloids, both in vitro and in vivo.	2.83	3	0	organic chloride salt	fluorochrome; geroprotector; histological dye
dexbrompheniramine dexbrompheniramine : The (pharmacologically active) (S)-(+)-enantiomer of brompheniramine. A histamine H1 receptor antagonist, it is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis.	2.04	1	0	brompheniramine	anti-allergic agent; H1-receptor antagonist
1,4-bis(2,3-epoxypropoxy)butane [no description available]	2.1	1	0
alpha-terpineol terpineol : A family of monoterpenols that have a p-menthane skeleton containing one double bond and bearing a single hydroxy substituent.	2.58	2	0	terpineol	plant metabolite
fucose Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.	2.97	4	0	fucopyranose; L-fucose	Escherichia coli metabolite; mouse metabolite
benzophenoneidum Benzophenoneidum: An aniline dye used as a disinfectant and an antiseptic agent. It is weakly fluorescing and binds specifically to certain proteins.. auramine O : A hydrochloride obtained by combining 4,4'-carbonimidoylbis(N,N-dimethylaniline) with one molar equivalent of hydrogen chloride. A fluorescent stain for demonstrating acid fast organisms in a method similar to the Ziehl Neelsen. It also can be used to make a fluorescent Schiff reagent.	2.31	1	0	hydrochloride	fluorochrome; histological dye
acridine red acridine red 3B : A hydrochloride obtained by combining the free base of acridine red 3B with one molar equivalent of hydrogen chloride. Used for staining RNA in conjunction with malachite green.	2.45	2	0
butyrylcholine butyrylcholine: RN given refers to parent cpd	2.05	1	0	acylcholine
tetrapentylammonium tetrapentylammonium: RN given refers to parent cpd	2.02	1	0	quaternary ammonium ion
gamma-glycidoxypropyltrimethoxysilane 3-glycidyloxypropyltrimethoxysilane: used to immobilize carbonic anhydrase into mesoporous supports; structure in first source	2.1	1	0
3-(trimethoxysilyl)propyl methacrylate 3-(trimethoxysilyl)propyl methacrylate: structure in first source	2.46	2	0
pontamine sky blue [no description available]	2.03	1	0
promecarb promecarb: structure	2.6	1	0	alkylbenzene
cyanophos [no description available]	2.11	1	0	organic thiophosphate; organothiophosphate insecticide	agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
octogen octogen: an explosive compound, contaminant in waste water; structure given in third source. octogen : A tetrazocane that is 1,3,5,7-tetrazocane in which the hydrogen atom attached to each of the nitrogens is replaced by a nitro group.	2.02	1	0	N-nitro compound; tetrazocane	explosive
hydroxyphenytoin hydroxyphenytoin: main metabolite of diphenylhydantoin; reduces Na(+) inhibition at high Na:K ratios; RN given refers to cpd without isomeric designation; structure. 4-hydroxyphenytoin : A imidazolidine-2,4-dione that consists of hydantoin bearing phenyl and 4-hydroxyphenyl substituents at position 5.	2	1	0	imidazolidine-2,4-dione; phenols	metabolite
2-(dimethylamino)ethyl methacrylate 2-(dimethylamino)ethyl methacrylate: reducing agent; structure given in first source	2.08	1	0
squaric acid [no description available]	2	1	0	alicyclic ketone; carbon oxoacid	metabolite
glycidyl trimethylammonium chloride glycidyl trimethylammonium: causes dermatitis on contact; structure given in first source; RN given refers to chloride	2.98	4	0
stavudine Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase	2.02	1	0	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
metobromuron metobromuron: structure	2.05	1	0	ureas
dicloxacillin Dicloxacillin: One of the PENICILLINS which is resistant to PENICILLINASE.. dicloxacillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]formyl group.	2.43	2	0	dichlorobenzene; penicillin	antibacterial drug
10-camphorsulfonic acid 10-camphorsulfonic acid: solucampher refers to piperazine salt; RN given refers to parent cpd; structure in Negwer. camphorsulfonic acid : A sulfonic acid containing the camphorsulfonate anion.	2.02	1	0	organosulfonic acid
didodecyldimethylammonium didodecyldimethylammonium: RN given refers to parent cpd	2.06	1	0
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.06	1	0	primary alcohol
fluorescein-5-isothiocyanate Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.	4.85	32	0	fluorescein isothiocyanate
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	5.14	10	1	thujene	plant metabolite
mannose mannopyranose : The pyranose form of mannose.	4.22	16	0	D-aldohexose; D-mannose; mannopyranose	metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	2.71	3	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
azo rubin s azo rubin S: RN given refers to parent cpd; structure	2.41	1	0
cyclazocine Cyclazocine: An analgesic with mixed narcotic agonist-antagonist properties.	2	1	0
cyclic cmp Cyclic CMP: A cyclic nucleotide formed from CYTIDINE TRIPHOSPHATE by the action of cytidylate cyclase. It is a potential cyclic nucleotide intracellular mediator of signal transductions.. 3',5'-cyclic CMP : A 3',5'-cyclic pyrimidine nucleotide having cytosine as the nucleobase.	2.04	1	0	3',5'-cyclic pyrimidine nucleotide	human metabolite
diloxanide furoate diloxanide furoate: structure. diloxanide furoate : A carboxylic ester resulting from the formal condensation of the carboxy group of furan-2-carboxylic acid with the hydroxy group of 2,2-dichloro-N-(4-hydroxyphenyl)-N-methylacetamide. It is a drug used for the treatment of asymptomatic amebiasis.	2.73	3	0	carboxylic ester; furans; organochlorine compound; tertiary carboxamide	antiamoebic agent; prodrug
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	3.01	4	0	carbon oxoanion
Brilliant Blue brilliant blue: coal tar derivative food dye; used as the di-NH4 or di-Na salts; RN given refers to parent cpd	2.11	1	0	organic molecular entity
bitoscanate bitoscanate: anthelmintic; minor descriptor (75-83); on-line & Index Medicus search THIOCYANATES (75-83); structure	2.08	1	0	benzenes
calcium propionate [no description available]	1.98	1	0	dicarboxylic acid
cladribine [no description available]	2.44	2	0	organochlorine compound; purine 2'-deoxyribonucleoside	antineoplastic agent; immunosuppressive agent
(3-mercaptopropyl)trimethoxysilane [no description available]	2.53	2	0
buthionine sulfoximine Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.	2.13	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
methylene bis(4-cyclohexylisocyanate) methylene bis(4-cyclohexylisocyanate): used in manufacture of polyurethane foam; RN given refers to cpd without isomeric designation. dicyclohexylmethane-4,4'-diisocyanate : A diisocyanate consisting of dicyclohexylmethane with two isocyanate groups at the 4- and 4'-positions.	2.1	1	0	diisocyanate	allergen
light green sf Light green SF: structure. acid green 5 : An organic sodium salt having 3-[(ethyl{4-[(4-{ethyl[(3-sulfonatophenyl)methyl]amino}phenyl)(4-sulfonatophenyl)methylidene]cyclohexa-2,5-dien-1-ylidene}azaniumyl)methyl]benzene-1-sulfonate as the counterion. It is the standard dye in North American for staining collagen and is also used extensively in plant histology.	2.31	1	0	organic sodium salt	histological dye
norleucine Norleucine: An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.. L-norleucine : A non-proteinogenic L-alpha-amino acid comprising hexanoic acid carrying an amino group at C-2. It does not occur naturally.	2.02	1	0	2-aminohexanoic acid; L-alpha-amino acid zwitterion; non-proteinogenic L-alpha-amino acid
1-hydroxypyrene 1-hydroxypyrene: pyrene metabolite; RN given refers to parent cpd	2.05	1	0	pyrenes
5-nitroindazole [no description available]	2.05	1	0
octylmethoxycinnamate octylmethoxycinnamate: a sunscreen used for prevention of DNA photodamage	2.75	3	0	cinnamate ester
aseanostatin p5 aseanostatin P5: from actinomycetes; inhibits myeloperoxidase release from human polymorphonuclear leukocytes; structure given in first source; RN given refers to cpd without isomeric designation. 12-methyltetradecanoic acid : A branched-chain saturated fatty acid comprising tetradecanoic acid carrying a 12-methyl substituent.	2.03	1	0	branched-chain saturated fatty acid; long-chain fatty acid
1-adamantanecarboxamide [no description available]	2	1	0
dimethindene Dimethindene: A histamine H1 antagonist. It is used in hypersensitivity reactions, in rhinitis, for pruritus, and in some common cold remedies.	2.93	4	0	indene
14-methylhexadecanoic acid 14-methylhexadecanoic acid: RN given refers to cpd without isomeric designation. 14-methylhexadecanoic acid : A methyl-branched fatty acid that is hexadecanoic acid (palmitic acid) substituted by a methyl group at position 14.	2.03	1	0	branched-chain saturated fatty acid; long-chain fatty acid; methyl-branched fatty acid	mammalian metabolite; plant metabolite
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	3.45	7	0	cycloalkene; p-menthadiene	human metabolite
olsalazine olsalazine: cpd with 2 salicylate molecules linked together by an azo bond. olsalazine : An azobenzene that consists of two molecules of 4-aminosalicylic acid joined by an azo linkage. A prodrug for mesalazine, an anti-inflammatory drug, it is used (as the disodium salt) in the treatment of inflammatory bowel disease.	2.21	1	0	azobenzenes; dicarboxylic acid	non-steroidal anti-inflammatory drug; prodrug
4-(4-dimethylaminophenylazo)benzoic acid 4-(4-dimethylaminophenylazo)benzoic acid: structure given in first source	2.06	1	0
n-methylaspartate N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.	3.17	5	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
enbucrilate Enbucrilate: A tissue adhesive that is applied as a monomer to moist tissue and polymerizes to form a bond. It is slowly biodegradable and used in all kinds of surgery, including dental.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; nitrile
helenalin helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.	2.46	2	0	cyclic ketone; gamma-lactone; organic heterotricyclic compound; secondary alcohol; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; plant metabolite
2,4,4'-trichlorobiphenyl [no description available]	2.13	1	0
1-phenyl-3,3-dimethyltriazene [no description available]	2.41	1	0
hepes [no description available]	2.01	1	0	HEPES; organosulfonic acid
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.08	1	0	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	3.8	10	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
mercury Mercury: A silver metallic element that exists as a liquid at room temperature. It has the atomic symbol Hg (from hydrargyrum, liquid silver), atomic number 80, and atomic weight 200.59. Mercury is used in many industrial applications and its salts have been employed therapeutically as purgatives, antisyphilitics, disinfectants, and astringents. It can be absorbed through the skin and mucous membranes which leads to MERCURY POISONING. Because of its toxicity, the clinical use of mercury and mercurials is diminishing.. mercury(0) : Elemental mercury of oxidation state zero.	3.49	7	0	elemental mercury; zinc group element atom	neurotoxin
molybdenum Molybdenum: A metallic element with the atomic symbol Mo, atomic number 42, and atomic weight 95.95. It is an essential trace element, being a component of the enzymes xanthine oxidase, aldehyde oxidase, and nitrate reductase.	2.61	2	0	chromium group element atom	micronutrient
neodymium Neodymium: An element of the rare earth family of metals. It has the atomic symbol Nd, atomic number 60, and atomic weight 144.24, and is used in industrial applications.	1.94	1	0	f-block element atom; lanthanoid atom
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	4.05	13	0	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	4.35	18	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	2.47	2	0	manganese group element atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	2.75	3	0	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	4.14	15	0	iron group element atom; platinum group metal atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	5.25	44	0	copper group element atom; elemental silver	Escherichia coli metabolite
technetium Technetium: The first artificially produced element and a radioactive fission product of URANIUM. Technetium has the atomic symbol Tc, and atomic number 43. All technetium isotopes are radioactive. Technetium 99m (m=metastable) which is the decay product of Molybdenum 99, has a half-life of about 6 hours and is used diagnostically as a radioactive imaging agent. Technetium 99 which is a decay product of technetium 99m, has a half-life of 210,000 years.	2.5	2	0	manganese group element atom
terbium Terbium: An element of the rare earth family of metals. It has the atomic symbol Tb, atomic number 65, and atomic weight 158.92.	2.77	3	0	f-block element atom; lanthanoid atom
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	4.88	31	0	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.21	1	0	chromium group element atom	micronutrient
argon Argon: A noble gas with the atomic symbol Ar, atomic number 18, and atomic weight 39.948. It is used in fluorescent tubes and wherever an inert atmosphere is desired and nitrogen cannot be used.	2.42	2	0	monoatomic argon; noble gas atom; p-block element atom	food packaging gas; neuroprotective agent
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	4.16	15	0	cadmium molecular entity; zinc group element atom
cerium Cerium: An element of the rare earth family of metals. It has the atomic symbol Ce, atomic number 58, and atomic weight 140.12. Cerium is a malleable metal used in industrial applications.	3.36	6	0	f-block element atom; lanthanoid atom
chromium Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.	3.81	10	0	chromium group element atom; metal allergen	micronutrient
erbium Erbium: Erbium. An element of the rare earth family of metals. It has the atomic symbol Er, atomic number 68, and atomic weight 167.26.	3.21	1	0	f-block element atom; lanthanoid atom
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	2.78	3	0	f-block element atom; lanthanoid atom
gadolinium Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.	4.32	18	0	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	6.12	110	0	copper group element atom; elemental gold
uranium Uranium: A radioactive element of the actinide series of metals. It has an atomic symbol U, atomic number 92, and atomic weight 238.03. U-235 is used as the fissionable fuel in nuclear weapons and as fuel in nuclear power reactors.	3.18	4	0	actinoid atom; f-block element atom; monoatomic uranium
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.41	1	0	elemental vanadium; vanadium group element atom	micronutrient
xenon Xenon: A noble gas with the atomic symbol Xe, atomic number 54, and atomic weight 131.30. It is found in the earth's atmosphere and has been used as an anesthetic.	1.98	1	0	monoatomic xenon; noble gas atom; p-block element atom
ytterbium Ytterbium: An element of the rare earth family of metals. It has the atomic symbol Yb, atomic number 70, and atomic weight 173. Ytterbium has been used in lasers and as a portable x-ray source.	3.9	3	0	f-block element atom; lanthanoid atom
yttrium Yttrium: An element of the rare earth family of metals. It has the atomic symbol Y, atomic number 39, and atomic weight 88.91. In conjunction with other rare earths, yttrium is used as a phosphor in television receivers and is a component of the yttrium-aluminum garnet (YAG) lasers.	2.08	1	0	d-block element atom; rare earth metal atom; scandium group element atom
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	3.18	5	0	titanium group element atom
aluminum chloride Aluminum Chloride: A compound with the chemical formula AlCl3; the anhydrous salt is used as a catalyst in organic chemical synthesis, and hydrated salts are used topically as antiperspirants, and for the management of HYPERHYDROSIS.	2.08	1	0	aluminium coordination entity	Lewis acid
zalcitabine Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.	1.98	1	0	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
magnesium sulfate Magnesium Sulfate: A small colorless crystal used as an anticonvulsant, a cathartic, and an electrolyte replenisher in the treatment of pre-eclampsia and eclampsia. It causes direct inhibition of action potentials in myometrial muscle cells. Excitation and contraction are uncoupled, which decreases the frequency and force of contractions. (From AMA Drug Evaluations Annual, 1992, p1083). magnesium sulfate : A magnesium salt having sulfate as the counterion.	1.98	1	0	magnesium salt; metal sulfate; organic magnesium salt	anaesthetic; analgesic; anti-arrhythmia drug; anticonvulsant; calcium channel blocker; cardiovascular drug; fertilizer; tocolytic agent
mercuric chloride Mercuric Chloride: Mercury chloride (HgCl2). A highly toxic compound that volatizes slightly at ordinary temperature and appreciably at 100 degrees C. It is corrosive to mucous membranes and used as a topical antiseptic and disinfectant.. mercury dichloride : A mercury coordination entity made up of linear triatomic molecules in which a mercury atom is bonded to two chlorines. Water-soluble, it is highly toxic. Once used in a wide variety of applications, including preserving wood and anatomical specimens, embalming and disinfecting, as an intensifier in photography, as a mordant for rabbit and beaver furs, and freeing gold from lead, its use has markedly declined as less toxic alternatives have been developed.	2.05	1	0	mercury coordination entity	sensitiser
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	2.08	1	0	N-acetyl-D-glucosamine	epitope
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	3.03	4	0	D-galactosamine; primary amino compound	toxin
phosphoric acid, trisodium salt [no description available]	2.73	3	0	sodium phosphate
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	2.05	1	0	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	6.64	46	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
ferric chloride ferric chloride: RN given refers to cpd with MF of Fe-Cl3; used to induce experimental arterial thrombosis to evaluate antithrombotic agents	3	4	0	iron coordination entity	astringent; Lewis acid
ferrous sulfate ferrous sulfate: Ferro-Gradumet is ferrous sulfate in controlled release form; RN given refers to Fe(+2)[1:1] salt. iron(2+) sulfate (anhydrous) : A compound of iron and sulfate in which the ratio of iron(2+) to sulfate ions is 1:1. Various hydrates occur naturally - most commonly the heptahydrate, which loses water to form the tetrahydrate at 57degreeC and the monohydrate at 65degreeC.	2.47	2	0	iron molecular entity; metal sulfate	reducing agent
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	2.05	1	0	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
bromine Bromine: A halogen with the atomic symbol Br, atomic number 35, and atomic weight 79.904. It is a volatile reddish-brown liquid that gives off suffocating vapors, is corrosive to the skin, and may cause severe gastroenteritis if ingested.	2.97	4	0	diatomic bromine
potassium persulfate [no description available]	2.74	3	0
potassium nitrate potassium nitrate: RN given refers to cpd with MF of K-HNO3; when combined with charcoal and sulfur it can form EXPLOSIVE AGENTS. potassium nitrate : The inorganic nitrate salt of potassium.	1.98	1	0	inorganic nitrate salt; potassium salt	fertilizer
sodium sulfate [no description available]	2.01	1	0	inorganic sodium salt
sodium sulfite [no description available]	2.44	2	0	inorganic sodium salt; sulfite salt	food preservative; reducing agent
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	3.17	5	0	calcium phosphate
ferrous chloride ferrous chloride: induces convulsions; RN given refers to parent cpd	2.07	1	0	iron coordination entity
chromates Chromates: Salts of chromic acid containing the CrO(2-)4 radical.. chromate(2-) : A chromium oxoanion resulting from the removal of two protons from chromic acid.	2.15	1	0	chromium oxoanion; divalent inorganic anion	oxidising agent
copper sulfate Copper Sulfate: A sulfate salt of copper. It is a potent emetic and is used as an antidote for poisoning by phosphorus. It also can be used to prevent the growth of algae.. copper(II) sulfate : A metal sulfate compound having copper(2+) as the metal ion.	2.05	1	0	metal sulfate	emetic; fertilizer; sensitiser
silver nitrate Silver Nitrate: A silver salt with powerful germicidal activity. It has been used topically to prevent OPHTHALMIA NEONATORUM.	2.7	3	0	inorganic nitrate salt; silver salt	astringent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	4.03	4	0	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	3.17	5	0	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.74	3	0	diatomic chlorine; gas molecular entity	bleaching agent
nitrous acid Nitrous Acid: Nitrous acid (HNO2). A weak acid that exists only in solution. It can form water-soluble nitrites and stable esters. (From Merck Index, 11th ed)	2.06	1	0	nitrogen oxoacid
deuterium oxide Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.	3.75	10	0	deuterated compound; water	NMR solvent
glycerol 1-stearate glycerol 1-stearate: isolated from the young fronds of the bracken fern Pteridium aquilinum; structure in first source. rac-1-monostearoylglycerol : A rac-1-monoacylglycerol composed of equal amounts of 3-stearoyl-sn-glycerol and 1-stearoyl-sn-glycerol.. 1-monostearoylglycerol : A 1-monoglyceride that has stearoyl as the acyl group.	1.99	1	0	1-acylglycerol 18:0; rac-1-monoacylglycerol	algal metabolite; Caenorhabditis elegans metabolite
poloxalene Poloxalene: A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.. pluronic : A triblock copolymer composed of a central hydrophobic chain of poly(propylene oxide) flanked by two hydrophilic chains of poly(ethylene oxide).	2.41	2	0	epoxide
hexadimethrine bromide Hexadimethrine Bromide: A synthetic polymer which agglutinates red blood cells. It is used as a heparin antagonist.	2.06	1	0
vasotocin Vasotocin: A nonapeptide that contains the ring of OXYTOCIN and the side chain of ARG-VASOPRESSIN with the latter determining the specific recognition of hormone receptors. Vasotocin is the non-mammalian vasopressin-like hormone or antidiuretic hormone regulating water and salt metabolism.. vasotocin : A heterodetic cyclic peptide that is homologous to oxytocin and vasopressin. It is a pituitary hormone that acts as an endocrine regulator for water balance, osmotic homoeostasis and is involved in social and sexual behavior in non-mammalian vertebrates.	2.42	2	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	2.48	2	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
sodium selenite disodium selenite : An inorganic sodium salt composed of sodium and selenite ions in a 2:1 ratio.	2.44	2	0	inorganic sodium salt; selenite salt	nutraceutical
4-chloro-7-nitrobenzofurazan 4-Chloro-7-nitrobenzofurazan: A benzofuran derivative used as a protein reagent since the terminal N-NBD-protein conjugate possesses interesting fluorescence and spectral properties. It has also been used as a covalent inhibitor of both beef heart mitochondrial ATPase and bacterial ATPase.. 4-chloro-7-nitrobenzofurazan : A benzoxadiazole that is 2,1,3-benzoxadiazole which is substituted at position 4 by chlorine and at position 7 by a nitro group.	2.94	4	0	benzoxadiazole; C-nitro compound; organochlorine compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; EC 3.6.1.3 (adenosinetriphosphatase) inhibitor; fluorescent probe; fluorochrome
camphoroquinone camphoroquinone: a natural monoterpene, non-aromatic quinone; structure given in first source. bornane-2,3-dione : A bornane monoterpenoid that is bicyclo[2.2.1]heptane substituted by methyl groups at positions 1, 7 and 7 and oxo groups at positions 2 and 3.	2.72	3	0	bornane monoterpenoid; carbobicyclic compound
trolamine salicylate Arthritis: Acute or chronic inflammation of JOINTS.	3.87	3	0
tetrazepam tetrazepam: structure	2.05	1	0	benzodiazepine
carbendazim carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.	3.07	4	0	benzimidazole fungicide; benzimidazoles; benzimidazolylcarbamate fungicide; carbamate ester	antifungal agrochemical; antinematodal drug; metabolite; microtubule-destabilising agent
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	3.17	5	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
n-ethyl-n-hydroxyethylnitrosamine N-ethyl-N-(2-hydroxyethyl)nitrosamine : A nitrosamine that is N-nitrosodiethylamine in which one of the ethyl froups has been replaced by a 2-hydroxyethyl group. It is used to induce renal and liver tumours in rodents.	1.96	1	0	nitrosamine; primary alcohol	carcinogenic agent
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	4.5	21	0	titanium oxides	food colouring
4-chlorophenoxyacetic acid 4-chlorophenoxyacetic acid: RN given refers to parent cpd; structure. (4-chlorophenoxy)acetic acid : A chlorophenoxyacetic acid that is phenoxyacetic acid carrying a chloro substituent at position 4.	2.02	1	0	chlorophenoxyacetic acid; monochlorobenzenes	phenoxy herbicide
diacerein diacerein: chelates with bivalent metals; a quinone which possesses redox properties; metabolized to active rhein; proposed mechanisms include inhibiting IL1 and metalloproteinases; called a slow acting symptomatic drug in osteoarthritis; no effect of cyclooxygenase;	2.1	1	0	anthraquinone
metopimazine metopimazine: RN given refers to parent cpd; structure	2.04	1	0	phenothiazines
4-biphenylylacetic acid ethyl ester [no description available]	2.67	3	0	biphenyls
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.59	2	0
dibenzo-18-crown-6 dibenzo-18-crown-6: structure. dibenzo-18-crown-6 : A crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18.	2.06	1	0	benzenes; crown ether	phase-transfer catalyst
etorphine Etorphine: A narcotic analgesic morphinan used as a sedative in veterinary practice.	2.73	3	0
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl.	2.92	4	0	selegiline; terminal acetylenic compound	geroprotector
levamisole Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.	2.06	1	0	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator
clemastine Clemastine: A histamine H1 antagonist used as the hydrogen fumarate in hay fever, rhinitis, allergic skin conditions, and pruritus. It causes drowsiness.. clemastine : 2-[(2R)-1-Methylpyrrolidin-2-yl]ethanol in which the hydrogen of the hydroxy group is substituted by a 1-(4-chlorophenyl)-1-phenylethyl group (R configuration). An antihistamine with antimuscarinic and moderate sedative properties, it is used as its fumarate salt for the symptomatic relief of allergic conditions such as rhinitis, urticaria, conjunctivitis and in pruritic (severe itching) skin conditions.	2.46	2	0	monochlorobenzenes; N-alkylpyrrolidine	anti-allergic agent; antipruritic drug; H1-receptor antagonist; muscarinic antagonist
thiamphenicol [no description available]	2.52	2	0	monocarboxylic acid amide; sulfone	antimicrobial agent; immunosuppressive agent
cephalexin Cephalexin: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.. cephalexin : A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.	1.96	1	0	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	4.11	15	0	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
gold tetrachloride, acid gold tetrachloride, acid: used in root canal therapy; RN given refers to (SP-4-1)	2.07	1	0
fluorides [no description available]	3.18	5	0	halide anion; monoatomic fluorine
danazol Danazol: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders.	3.3	6	0	17beta-hydroxy steroid; terminal acetylenic compound	anti-estrogen; estrogen antagonist; geroprotector
18-crown-6 18-crown-6 : A crown ether that is cyclooctadecane in which the carbon atoms at positions 1, 4, 7, 10, 13 and 16 have been replaced by oxygen atoms.	3.29	6	0	crown ether; saturated organic heteromonocyclic parent	phase-transfer catalyst
stilbene oxide stilbene oxide: inducer of epoxide hydratase; RN given refers to cpd without isomeric designation	2.04	1	0	epoxide
tert-butyldimethylsilyl chloride tert-butyldimethylsilyl chloride: structure in first source. tert-butyldimethylsilyl chloride : A silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry applications.	2.31	1	0	silyl chloride	chromatographic reagent
chromium chromium hexavalent ion: a human respiratory carcinogen	3.42	6	0	chromium cation; monoatomic hexacation
1-deoxynojirimycin 1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.	5.46	10	0	2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid	anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite
iodine [no description available]	2.75	3	0	halide anion; monoatomic iodine	human metabolite
neohesperidin dihydrochalcone neohesperidin dihydrochalcone : A member of the dihydrochalcones that is 3,2',4',6'-tetrahydroxy-4-methoxydihydrochalcone attached to a neohesperidosyl residue at position 4' via glycosidic linkage. It is found in sweet orange.	2.02	1	0	dihydrochalcones; disaccharide derivative; neohesperidoside	environmental contaminant; plant metabolite; sweetening agent; xenobiotic
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	2.31	1	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
padimate-o padimate-O: active ingredient in sunscreen products	2	1	0	benzoate ester
phosphotyrosine Phosphotyrosine: An amino acid that occurs in endogenous proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis.. O(4)-phospho-L-tyrosine : A non-proteinogenic L-alpha-amino acid that is L-tyrosine phosphorylated at the phenolic hydroxy group.	3.52	8	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid; O(4)-phosphotyrosine	Escherichia coli metabolite; immunogen
fenamiphos [no description available]	2.05	1	0	organophosphate insecticide; organophosphate nematicide; phosphoramidate ester	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
fenitrothion Fenitrothion: An organothiophosphate cholinesterase inhibitor that is used as an insecticide.. fenitrothion : An organic thiophosphate that is O,O-dimethyl O-phenyl phosphorothioate substituted by a methyl group at position 3 and a nitro group at position 4.	2.55	2	0	C-nitro compound; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; insecticide
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	5.08	40	0	benzenes; phenyl acetates
cetylpyridinium chloride anhydrous tserigel: according to first source contains polyvinylbutyral & cetylpyridinium chloride; UD only lists cetylpyridinium chloride as constituent. cetylpyridinium chloride : A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.	2.04	1	0	chloride salt; organic chloride salt	antiseptic drug; surfactant
methylformamide N-methylformamide : A member of the class of formamides having a N-methyl substituent.	2.43	2	0	formamides
butyl acetate butyl acetate: structure. butyl acetate : The acetate ester of butanol.	2.11	1	0	acetate ester	metabolite
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	3.15	5	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
nonanal nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.	2.39	2	0	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human metabolite; plant metabolite
triamcinolone Triamcinolone: A glucocorticoid given, as the free alcohol or in esterified form, orally, intramuscularly, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. (From Martindale, The Extra Pharmacopoeia, 30th ed, p739). triamcinolone : A C21-steroid hormone that is 1,4-pregnadiene-3,20-dione carrying four hydroxy substituents at positions 11beta, 16alpha, 17alpha and 21 as well as a fluoro substituent at position 9. Used in the form of its 16,17-acetonide to treat various skin infections.	2.95	4	0	11beta-hydroxy steroid; 16alpha-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-allergic agent; anti-inflammatory drug
sucrose octaacetate sucrose octaacetate: bitter tasting cpd preferred by rats to quinine; RN given refers to ((beta-D)-fructofuranosyl)-isomer	2.03	1	0	glycoside
tetrachloroethylene Tetrachloroethylene: A chlorinated hydrocarbon used as an industrial solvent and cooling liquid in electrical transformers. It is a potential carcinogen.	2.04	1	0	chlorocarbon; chloroethenes	nephrotoxic agent
dimethylacetamide hallucinogen : Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.. N,N-dimethylacetamide : A member of the class of acetamides that is acetamide in which the hydrogens attached to the N atom have been replaced by two methyl groups respectively. Metabolite observed in cancer metabolism.	2.95	4	0	acetamides; monocarboxylic acid amide	human metabolite
ursodeoxycholic acid Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.. ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.. ursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	3.53	8	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
pregnanolone Pregnanolone: A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties.. 3alpha-hydroxy-5beta-pregnan-20-one : The 3alpha-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.	15.12	57	7	3-hydroxy-5beta-pregnan-20-one; 3alpha-hydroxy steroid	human metabolite; intravenous anaesthetic; sedative
pyrene pyrene: structure in Merck Index, 9th ed, #7746. pyrene : An ortho- and peri-fused polycyclic arene consisting of four fused benzene rings, resulting in a flat aromatic system.	4.21	16	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
benzonidazole benzonidazole: used in treatment of Chagas' disease. benznidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitroimidazol-1-yl)acetic acid with the aromatic amino group of benzylamine. Used for treatment of Chagas disease.	2.77	3	0	C-nitro compound; imidazoles; monocarboxylic acid amide	antiprotozoal drug
pirimicarb pirimicarb: structure. pirimicarb : An aminopyrimidine that is N,N,4,5-tetramethylpyrimidin-2-amine substituted by a (dimethylcarbamoyl)oxy group at position 4.	2.17	1	0	aminopyrimidine; carbamate ester; tertiary amino compound	agrochemical; carbamate insecticide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
butachlor butachlor : An aromatic amide that is 2-choro-N-(2,6-diethylphenyl)acetamide in which the amide nitrogen has been replaced by a butoxymethyl group.	2.05	1	0	aromatic amide; organochlorine compound; tertiary carboxamide	environmental contaminant; herbicide; xenobiotic
8-bromo cyclic adenosine monophosphate 8-Bromo Cyclic Adenosine Monophosphate: A long-acting derivative of cyclic AMP. It is an activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.. 8-Br-cAMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic AMP bearing an additional bromo substituent at position 8 on the adenine ring. An activator of cyclic AMP-dependent protein kinase, but resistant to degradation by cyclic AMP phosphodiesterase.	2.02	1	0	3',5'-cyclic purine nucleotide; adenyl ribonucleotide; organobromine compound	antidepressant; protein kinase agonist
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states.	4.12	15	0
alkenes [no description available]	3.54	8	0
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	4.65	26	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
glucaric acid Glucaric Acid: A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups.. D-glucaric acid : The D-enantiomer of glucaric acid.. glucaric acid : A hexaric acid derived by oxidation of sugar such as glucose with nitric acid.	2.03	1	0	glucaric acid	antineoplastic agent
adenylyl imidodiphosphate Adenylyl Imidodiphosphate: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.	2.05	1	0	adenosine 5'-phosphate
torpedo Torpedo: A genus of the Torpedinidae family consisting of several species. Members of this family have powerful electric organs and are commonly called electric rays.	2.25	1	0
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.94	12	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
amoxicillin Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.	3.13	5	0	penicillin allergen; penicillin	antibacterial drug
timolol (S)-timolol (anhydrous) : The (S)-(-) (more active) enantiomer of timolol. A beta-adrenergic antagonist, both the hemihydrate and the maleate salt are used in the mangement of glaucoma, hypertension, angina pectoris and myocardial infarction, and for the prevention of migraine.	2.94	4	0	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist
2-bromoethanesulfonic acid 2-bromoethanesulfonic acid: RN given refers to parent cpd; a methanogenic inhibitor	2.11	1	0
tramadol Tramadol: A narcotic analgesic proposed for severe pain. It may be habituating.. tramadol : A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Gruenenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.. (R,R)-tramadol : A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.	2.81	3	0	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor
norflurazone norflurazone: structure. norflurazon : A pyridazinone that is pyridazin-3(2H)-one which is substituted at positions 2, 4, and 5 by m-(trifluoromethyl)phenyl, chloro, and methylamino groups, respectively. A pre-emergence herbicide used to control grasses and broad-leafed weeds in a variety of crops. Not approved for use within the European Union.	2.94	4	0	(trifluoromethyl)benzenes; organochlorine compound; pyridazinone; secondary amino compound	agrochemical; carotenoid biosynthesis inhibitor; herbicide
ensulizole ensulizole: sunscreening agent; structure in first source	2.08	1	0	benzimidazoles
nigericin Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.	2.4	2	0	polycyclic ether	antibacterial agent; antimicrobial agent; bacterial metabolite; potassium ionophore
oxcarbazepine Oxcarbazepine: A carbamazepine derivative that acts as a voltage-gated sodium channel blocker. It is used for the treatment of PARTIAL SEIZURES with or without secondary generalization. It is also an inducer of CYTOCHROME P-450 CYP3A4.. oxcarbazepine : A dibenzoazepine derivative, having a carbamoyl group at the ring nitrogen, substituted with an oxo group at C-4 of the azepeine ring which is also hydrogenated at C-4 and C-5. It is a anticholinergic anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy.	2.04	1	0	cyclic ketone; dibenzoazepine	anticonvulsant; drug allergen
1-(9-fluorenyl)methyl chloroformate 1-(9-fluorenyl)methyl chloroformate: used for tagging silica-based derivatization reagents in HPLC	2.46	2	0
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.77	3	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
acetylgalactosamine Acetylgalactosamine: The N-acetyl derivative of galactosamine.	2.6	1	0	N-acetyl-D-hexosamine; N-acetylgalactosamine	Escherichia coli metabolite; human metabolite; mouse metabolite
flubendazole flubendazole: the p-fluoro analog of mebendazole. flubendazole : A member of the class of mebendazole in which the benzoyl group is replaced by a p-fluorobenzoyl group. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections.	3.16	5	0	aromatic ketone; benzimidazoles; carbamate ester; organofluorine compound	antinematodal drug; teratogenic agent
pirprofen pirprofen: anti-inflammatory agent used in therapy of rheumatoid arthritis; prostaglandin synthetase inhibitor; more potent than indomethacin; structure	1.96	1	0	pyrroline
sisomicin Sisomicin: Antibiotic produced by Micromonospora inyoensis. It is closely related to gentamicin C1A, one of the components of the gentamicin complex (GENTAMICINS).	2.48	2	0	amino cyclitol glycoside; aminoglycoside antibiotic; beta-L-arabinoside; monosaccharide derivative
3,4,3',4'-tetrachlorobiphenyl 3,4,3',4'-tetrachlorobiphenyl: RN given refers to parent cpd. 3,3',4,4'-tetrachlorobiphenyl : A tetrachlorobiphenyl that is biphenyl in which the hydrogens at position 3 and 4 on each phenyl group are replaced by chlorines.	2.1	1	0	dichlorobenzene; tetrachlorobiphenyl
tobramycin Tobramycin: An aminoglycoside, broad-spectrum antibiotic produced by Streptomyces tenebrarius. It is effective against gram-negative bacteria, especially the PSEUDOMONAS species. It is a 10% component of the antibiotic complex, NEBRAMYCIN, produced by the same species.. tobramycin : A amino cyclitol glycoside that is kanamycin B lacking the 3-hydroxy substituent from the 2,6-diaminoglucose ring.	3.19	5	0	amino cyclitol glycoside	antibacterial agent; antimicrobial agent; toxin
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	5.37	53	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	3.49	7	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	3.1	5	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
isoproturon isoproturon : A member of the class of phenylureas that is 1,1-dimethylurea substituted by a p-cumenyl group at position 3. A selective, systemic herbicide used to control annual grasses and broadleaf weeds in cereals, its use within the EU has been banned after September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its endocrine-disrupting properties.	3.13	5	0	3-(3,4-substituted-phenyl)-1,1-dimethylurea	agrochemical; environmental contaminant; herbicide; xenobiotic
oxazepam hemisuccinate oxazepam hemisuccinate: RN given refers to cpd without isomeric designation; structure in Negwer, 5th ed, #3843	2.31	1	0
1,10-decanediol [no description available]	2.15	1	0
enilconazole enilconazole: RN given refers to parent cpd. enilconazole : A racemate comprising equimolar amounts of (R)- and (S)-enilconazole. A fungicide used to control a wide range of fungi including Tilletia and Helminthosporium spp. on fruit, vegetables and ornamentals. In veterinary medicine, it is used topically for the treatment of fungal skin infections in cattle, dogs, and horses; it is also used by inhalation for the treatment of aspergillosis in ostriches.. 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole : A member of the class of imidazoles in which the hydrogen at position 1 is replaced by a 2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl group.	3.28	6	0	dichlorobenzene; ether; imidazoles
halofantrine halofantrine: used in treatment of mild to moderate acute malaria	2.03	1	0	phenanthrenes
iprodione iprodione : An imidazolidine-2,4-dione in which the nitrogen at position 1 is substituted by an N-(isopropyl)carboxamide group while that at position 3 is substituted by a 3,5-dichlorophenyl group. A contact fungicide, it blocks the growth of the fungal mycelium and inhibits the germination of fungal spores. It is used on fruit and vegetable crops affected by various fungal diseases. It is also used as a nematicide.	2.03	1	0	benzenes; dichlorophenyl dicarboximide fungicide; imidazole fungicide; imidazolidine-2,4-dione; ureas	antifungal agrochemical; nematicide
ribavirin Rebetron: Rebetron is tradename	2.03	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
cicloprofen [no description available]	2.05	1	0
amikacin Amikacin: A broad-spectrum antibiotic derived from KANAMYCIN. It is reno- and oto-toxic like the other aminoglycoside antibiotics.. amikacin : An amino cyclitol glycoside that is kanamycin A acylated at the N-1 position by a 4-amino-2-hydroxybutyryl group.	2.13	1	0	alpha-D-glucoside; amino cyclitol glycoside; aminoglycoside; carboxamide	antibacterial drug; antimicrobial agent; nephrotoxin
fluorescamine Fluorescamine: A nonfluorescent reagent for the detection of primary amines, peptides and proteins. The reaction products are highly fluorescent.	2.72	3	0
cephradine Cephradine: A semi-synthetic cephalosporin antibiotic.. cephradine : A first-generation cephalosporin antibiotic with a methyl substituent at position 3, and a (2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetamido substituent at position 7, of the cephem skeleton.	2.1	1	0	beta-lactam antibiotic allergen; cephalosporin	antibacterial drug
methyldopa Methyldopa: An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.. alpha-methyl-L-dopa : A derivative of L-tyrosine having a methyl group at the alpha-position and an additional hydroxy group at the 3-position on the phenyl ring.	2.44	2	0	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	alpha-adrenergic agonist; antihypertensive agent; hapten; peripheral nervous system drug; sympatholytic agent
tocainide Tocainide: An antiarrhythmic agent which exerts a potential- and frequency-dependent block of SODIUM CHANNELS.. tocainide : A monocarboxylic acid amide in which 2,6-dimethylphenylaniline and isobutyric acid have combined to form the amide bond; used as a local anaesthetic.	2.02	1	0	monocarboxylic acid amide	anti-arrhythmia drug; local anaesthetic; sodium channel blocker
tricyclazole tricyclazole: RN given refers to parent cpd. tricyclazole : A triazolobenzothiazole that is [1,2,4]triazolo[3,4-b][1,3]benzothiazole which is substituted at position 5 by a methyl group. A fungicide used for the control of rice blast, it is not approved for use within the European Union.	2.03	1	0	triazolobenzothiazole	antifungal agrochemical; melanin synthesis inhibitor
sq-11725 Nadolol: A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor.. nadolol : Nadolol is a diastereoisomeric mixture consisting of equimolar amounts of the four possible 2,3-cis-isomers of 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol.	2.41	2	0
diltiazem Diltiazem: A benzothiazepine derivative with vasodilating action due to its antagonism of the actions of CALCIUM ion on membrane functions.. diltiazem : A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.	2.89	4	0	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent
triadimefon 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one : A member of the class of triazoles that is 1-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one in which the hydroxyl hydrogen is replaced by a 4-chlorophenyl group.	2.72	3	0	aromatic ether; hemiaminal ether; ketone; monochlorobenzenes; triazoles
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.25	1	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
lonidamine lonidamine: structure. lonidamine : A member of the class of indazoles that is 1H-indazole that is substituted at positions 1 and 3 by 2,4-dichlorobenzyl and carboxy groups, respectively.	1.99	1	0	dichlorobenzene; indazoles; monocarboxylic acid	antineoplastic agent; antispermatogenic agent; EC 2.7.1.1 (hexokinase) inhibitor; geroprotector
vx VX nerve agent : A organic thiophosphate that is the ethyl ester of S-{2-[di(propan-2-yl)amino]ethyl} O hydrogen methylphosphonothioate. A toxic nerve agent used in chemical warfare.	2.4	2	0	organic thiophosphate; tertiary amino compound	EC 3.1.1.7 (acetylcholinesterase) inhibitor; neurotoxin
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	3.21	4	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
dexibuprofen dexibuprofen: structure in first source	2.15	1	0	ibuprofen	non-narcotic analgesic; non-steroidal anti-inflammatory drug
dichlorfop-methyl dichlorfop-methyl: structure; herbicide for control of wild oat & foxtails in cereal crops. diclofop-methyl : A racemate composed of equimolar amounts of (R)- and (S)-diclofop-methyl. A proherbicide for diclofop, it is used for the control of wild oats and annual weeds in wheat, barley, rye and broad-leaved crops.. methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate : A methyl ester resulting from the formal condensation of the carboxylic acid group of 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid with methanol.	2.43	2	0	aromatic ether; dichlorobenzene; diether; methyl ester
thidiazuron [no description available]	2.13	1	0	ureas
permethrin hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141	3.92	12	0	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide
decamethrin decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure	2.44	2	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organobromine compound	agrochemical; antifeedant; calcium channel agonist; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; pyrethroid ester insecticide
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid [no description available]	2.73	3	0	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
oxfendazole [no description available]	2.05	1	0	benzimidazoles; carbamate ester; sulfoxide	antinematodal drug
meptazinol Meptazinol: A narcotic antagonist with analgesic properties. It is used for the control of moderate to severe pain.	2.1	1	0	azepanes
3,3',5,5'-tetramethylbenzidine T1023: radioprotective NO-Synthase Inhibitor	2.93	4	0
6-benzoyl benzoxazolinone 6-benzoyl benzoxazolinone: structure given in first source	1.96	1	0
sufentanil Sufentanil: An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent.. sufentanil : An anilide resulting from the formal condensation of the aryl amino group of 4-(methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]piperidin-4-amine with propanoic acid.	2.91	4	0	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
indacrinone indacrinone: polyvalent saluretic; RN given refers to parent cpd without isomeric designation; structure	2.11	1	0
enkephalin, methionine Enkephalin, Methionine: One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.	2.05	1	0
laurocapram laurocapram: enhances percutaneous absorption of different chemicals; structure given in first source	2.42	2	0
paroxetine Paroxetine: A serotonin uptake inhibitor that is effective in the treatment of depression.. paroxetine : A benzodioxole that consists of piperidine bearing 1,3-benzodioxol-5-yloxy)methyl and 4-fluorophenyl substituents at positions 3 and 4 respectively; the (3S,4R)-diastereomer. Highly potent and selective 5-HT uptake inhibitor that binds with high affinity to the serotonin transporter (Ki = 0.05 nM). Ki values are 1.1, 350 and 1100 nM for inhibition of [3H]-5-HT, [3H]-l-NA and [3H]-DA uptake respectively. Displays minimal affinity for alpha1-, alpha2- or beta-adrenoceptors, 5-HT2A, 5-HT1A, D2 or H1 receptors at concentrations below 1000 nM, however displays weak affinity for muscarinic ACh receptors (Ki = 42 nM). Antidepressant and anxiolytic in vivo.	2.43	2	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
captopril Captopril: A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.. captopril : A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.	2.69	3	0	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
cefoperazone Cefoperazone: Semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It may be used to treat Pseudomonas infections.. cefoperazone : A semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance.	2.43	2	0	cephalosporin	antibacterial drug
salsoline salsoline: monomethylated metabolite of salsolinol; endogenous neurotoxin found in CSF of patients with Parkinson's disease	1.99	1	0	isoquinolines
colforsin Colforsin: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant COLEUS FORSKOHLII. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.	3.27	6	0	acetate ester; cyclic ketone; labdane diterpenoid; organic heterotricyclic compound; tertiary alpha-hydroxy ketone; triol	adenylate cyclase agonist; anti-HIV agent; antihypertensive agent; plant metabolite; platelet aggregation inhibitor; protein kinase A agonist
fenoxaprop ethyl Puma: A genus in the family FELIDAE comprising one species, Puma concolor. It is a large, long-tailed, feline of uniform color. The names puma, cougar, and mountain lion are used interchangeably for this species. There are more than 20 subspecies.	2.02	1	0	aromatic ether
buserelin Buserelin: A potent synthetic analog of GONADOTROPIN-RELEASING HORMONE with D-serine substitution at residue 6, glycine10 deletion, and other modifications.	2.9	4	0	oligopeptide
tiotidine tiotidine: UD gives slightly different structure for this cpd; RN given refers to parent cpd; structure in first source	1.99	1	0	thiazoles
avobenzone [no description available]	2.95	4	0	dihydrochalcones
pefloxacin Pefloxacin: A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.. pefloxacin : A quinolone that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6 and 7 by ethyl, carboxy, fluorine, and 4-methylpiperazin-1-yl groups, respectively.	2.03	1	0	fluoroquinolone antibiotic; monocarboxylic acid; N-alkylpiperazine; N-arylpiperazine; quinolone antibiotic; quinolone	antibacterial drug; antiinfective agent; DNA synthesis inhibitor
alfentanil Alfentanil: A short-acting opioid anesthetic and analgesic derivative of FENTANYL. It produces an early peak analgesic effect and fast recovery of consciousness. Alfentanil is effective as an anesthetic during surgery, for supplementation of analgesia during surgical procedures, and as an analgesic for critically ill patients.. alfentanil : A member of the class of piperidines that is piperidine having a 2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl group at the 1-position as well as N-phenylpropanamido- and methoxymethyl groups at the 4-position.	1.98	1	0	monocarboxylic acid amide; piperidines	central nervous system depressant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; peripheral nervous system drug
benalaxyl benalaxyl: RN given refers to (DL)-isomer; structure given in first source. benalaxyl : A racemate comprising equal amounts of (R)- and (S)-benalaxyl.. methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate : An alanine derivative that is the N-phenylacetyl derivative of methyl N-(2,6-dimethylphenyl)alaninate	2.01	1	0	alanine derivative; aromatic amide; carboxamide; methyl ester
fomesafen fomesafen: a protoporphyrinogen oxidase-inhibiting herbicide. fomesafen : An N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya.	2.72	3	0	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide
fenoxycarb fenoxycarb: used against mosquitoes (Diptera:Culicidae); structure given in first source. fenoxycarb : A carbamate ester that is the O-ethyl carbamate of 2-(4-phenoxyphenoxy)ethylamine.	2.1	1	0	aromatic ether; carbamate ester	environmental contaminant; insecticide; juvenile hormone mimic; xenobiotic
miglustat miglustat: a glucosylceramide synthase inhibitor. miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.	5.17	7	0	piperidines; tertiary amino compound	anti-HIV agent; EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
lovastatin Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).	5.8	28	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug
bermoprofen bermoprofen: structure given in first source	1.96	1	0	dibenzooxazepine
simvastatin Simvastatin: A derivative of LOVASTATIN and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL RECEPTORS, it increases breakdown of LDL CHOLESTEROL.. simvastatin : A member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug.	4.61	24	0	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug
pravastatin Pravastatin: An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES).. pravastatin : A carboxylic ester resulting from the formal condensation of (S)-2-methylbutyric acid with the hydroxy group adjacent to the ring junction of (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid. Derived from microbial transformation of mevastatin, pravastatin is a reversible inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA). The sodium salt is used for lowering cholesterol and preventing cardiovascular disease. It is one of the lower potency statins, but has the advantage of fewer side effects compared with lovastatin and simvastatin.	2.03	1	0	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic
imazaquin imazaquin: RN given refer to parent cpd. imazaquin : A racemate comprising equimolar amounts of (R)- and (S)-imazaquin. It is a pre- and post-emergence herbicide used for the control of grasses and broad-leaved weeds.. 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid : A quinolinemonocarboxylic acid that is quinoline-3-carboxylic acid which is substituted by a 4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl group at position 2.	2.03	1	0	imidazolone; monocarboxylic acid; quinolinemonocarboxylic acid
imazethapyr imazethapyr: do not confuse with imazapyr, which is the 5-desethyl analog of imazethapyr	2.66	2	0	aromatic carboxylic acid; pyridines
atomoxetine hydrochloride Atomoxetine Hydrochloride: A propylamine derivative and selective ADRENERGIC UPTAKE INHIBITOR that is used in the treatment of ATTENTION DEFICIT HYPERACTIVITY DISORDER.. atomoxetine hydrochloride : The hydrochloride salt of atomoxetine.	2.41	1	0	hydrochloride	adrenergic uptake inhibitor; antidepressant
quinapril Quinapril: A tetrahydroisoquinoline derivative and ANGIOTENSIN CONVERTING ENZYME inhibitor that is used in the treatment of HYPERTENSION and HEART FAILURE.. quinapril : A member of the class of isoquinolines that is (3S)-2-L-alanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in which the alpha-amino group of the alanyl residue has been substituted by a 1-ethoxycarbonyl-4-phenylbutan-2-yl group (the all-S isomer). A prodrug for quinaprilat (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) used (generally as the hydrochloride salt) for the treatment of hypertension and congestive heart failure.	2.01	1	0	dicarboxylic acid monoester; ethyl ester; isoquinolines; tertiary carboxamide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug
raloxifene hydrochloride Raloxifene Hydrochloride: A second generation selective estrogen receptor modulator (SERM) used to prevent osteoporosis in postmenopausal women. It has estrogen agonist effects on bone and cholesterol metabolism but behaves as a complete estrogen antagonist on mammary gland and uterine tissue.. raloxifene hydrochloride : A hydrochloride salt resulting from the reaction of equimolar amounts of raloxifene and hydrogen chloride.	3.19	5	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
itraconazole Itraconazole: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.. itraconazole : An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.	8.6	25	7	aromatic ether; conazole antifungal drug; cyclic ketal; dichlorobenzene; dioxolane; N-arylpiperazine; triazole antifungal drug; triazoles	EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; Hedgehog signaling pathway inhibitor; P450 inhibitor
disoxaril disoxaril: antipicornavirus agent	2.03	1	0	aromatic ether
ractopamine ractopamine: veterinary growth stimulant. ractopamine : A diastereoisomeric mixture of approximately equal amounts of all four possible diastereoisomers of 4-(1-hydroxy-2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)phenol. A beta-adrenergic agonist, it is used (generally as the hydrochloride salt) as a feed additive for use in pigs and other livestock to promote protein deposition, resulting in leaner meat. The R,R diastereoisomer, butopamine, is responsible for most of the leanness-enhancing effects. While use of ractopamine has been banned in over 120 countries including throughout the EU, in the US it used in an estimated 80% of all beef, pork and turkey production.. 4-(1-hydroxy-2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)phenol : A secondary amino compound that is 4-(2-amino-1-hydroxyethyl)phenol in which one of the hydrogens attached to the nitrogen is replaced by a 4-(p-hydroxyphenyl)butan-2-yl group.	2.72	2	0	benzyl alcohols; polyphenol; secondary alcohol; secondary amino compound
fosphenytoin fosphenytoin: structure given in first & second source	1.99	1	0	imidazolidine-2,4-dione
fluorodopa f 18 fluorodopa F 18: RN given refers to (L)-isomer	2.15	1	0	(18)F radiopharmaceutical; 6-fluoro-L-dopa
clentiazem clentiazem: structure given in first source	1.98	1	0
fura-2 Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.	2.74	3	0
finasteride Finasteride: An orally active 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE inhibitor. It is used as a surgical alternative for treatment of benign PROSTATIC HYPERPLASIA.. finasteride : An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.	2.49	2	0	3-oxo steroid; aza-steroid; delta-lactam	androgen antagonist; antihyperplasia drug; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
imiquimod Imiquimod: A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.. imiquimod : An imidazoquinoline fused [4,5-c] carrying isobutyl and amino substituents at N-1 and C-4 respectively. A prescription medication, it acts as an immune response modifier and is used to treat genital warts, superficial basal cell carcinoma, and actinic keratosis.	2.83	3	0	imidazoquinoline	antineoplastic agent; interferon inducer
mk 458 MK 458: a sustained release formulation of a naphthoxazine compoud with selective D-2 dopamine receptor agonism. naxagolide hydrochloride : The hydrochloride salt of naxagolide.	3.26	6	0	hydrochloride	anticonvulsant; antiparkinson drug; dopamine agonist
n 0437, (-)-isomer rotigotine: Antiparkinson Agent and dopamine receptor agonist; structure given in first source; RN given refers to cpd without isomeric designation	2.04	1	0	tetralins
esmolol methyl 3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate : A methyl ester that is methyl 3-(4-hydroxyphenyl)propanoate in which the hydrogen attached to the phenolic hydroxy group is substituted by a 2-hydroxy-3-(isopropylamino)propyl group.. esmolol : A racemate comprising equimolar amounts of (R)- and (S)-esmolol. A cardioselective and short-acting beta1 receptor blocker with rapid onset but lacking intrinsic sympathomimetic and membrane-stabilising properties, it is used as the hydrochloride salt in the management of supraventricular arrhythmias, and for the control of hypertension and tachycardia during surgery. While the S enantiomer possesses all of the heart rate control, both enantiomers contribute to lowering blood pressure.	2.55	2	0	aromatic ether; ethanolamines; methyl ester; secondary alcohol; secondary amino compound
bidisomide bidisomide: RN given refers to parent cpd	2	1	0	acetamides
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	1.98	1	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
aromasil [no description available]	2.08	1	0	17-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor; environmental contaminant; xenobiotic
sparfloxacin [no description available]	2.71	3	0	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone
clopidogrel Clopidogrel: A ticlopidine analog and platelet purinergic P2Y receptor antagonist that inhibits adenosine diphosphate-mediated PLATELET AGGREGATION. It is used to prevent THROMBOEMBOLISM in patients with ARTERIAL OCCLUSIVE DISEASES; MYOCARDIAL INFARCTION; STROKE; or ATRIAL FIBRILLATION.. clopidogrel : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group, the methylene hydrogen of which is replaced by a methoxycarbonyl group (the S enantiomer). A P2Y12 receptor antagonist, it is used to inhibit blood clots and prevent heart attacks.	5.63	3	2	methyl ester; monochlorobenzenes; thienopyridine	anticoagulant; P2Y12 receptor antagonist; platelet aggregation inhibitor
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	2.49	2	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
tiagabine Tiagabine: A nipecotic acid derivative that acts as a GABA uptake inhibitor and anticonvulsant agent. It is used in the treatment of EPILEPSY, for refractory PARTIAL SEIZURES.. tiagabine : A piperidinemonocarboxylic acid that is (R)-nipecotic acid in which the hydrogen attached to the nitrogen has been replaced by a 1,1-bis(3-methyl-2-thienyl)but-1-en-4-yl group. A GABA reuptake inhibitor, it is used (generally as the hydrochloride salt) for the treatment of epilepsy.	2.25	1	0	beta-amino acid; piperidinemonocarboxylic acid; tertiary amino compound; thiophenes	anticonvulsant; GABA reuptake inhibitor
liarozole liarozole: inhibits all-trans-retinoic acid 4-hydroxylase; effective against hormone-dependent and hormone-independent tumors; R 75251 is chlorohydrate of R 61405; a potent inhibitor of retinoic acid metabolism; USAN name - liarozole fumarate	1.98	1	0	benzimidazoles
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.72	2	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
temoporfin temoporfin: used as PHOTOCHEMOTHERAPY	2.54	2	0
aripiprazole Aripiprazole: A piperazine and quinolone derivative that is used primarily as an antipsychotic agent. It is a partial agonist of SEROTONIN RECEPTOR, 5-HT1A and DOPAMINE D2 RECEPTORS, where it also functions as a post-synaptic antagonist, and an antagonist of SEROTONIN RECEPTOR, 5-HT2A. It is used for the treatment of SCHIZOPHRENIA and BIPOLAR DISORDER, and as an adjunct therapy for the treatment of depression.. aripiprazole : An N-arylpiperazine that is piperazine substituted by a 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl group at position 1 and by a 2,3-dichlorophenyl group at position 4. It is an antipsychotic drug used for the treatment of Schizophrenia, and other mood disorders.	4.47	6	0	aromatic ether; delta-lactam; dichlorobenzene; N-alkylpiperazine; N-arylpiperazine; quinolone	drug metabolite; H1-receptor antagonist; second generation antipsychotic; serotonergic agonist
atorvastatin [no description available]	3.2	5	0	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
lamivudine [no description available]	2.96	4	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
duloxetine hydrochloride Duloxetine Hydrochloride: A thiophene derivative and selective NEUROTRANSMITTER UPTAKE INHIBITOR for SEROTONIN and NORADRENALINE (SNRI). It is an ANTIDEPRESSIVE AGENT and ANXIOLYTIC, and is also used for the treatment of pain in patients with DIABETES MELLITUS and FIBROMYALGIA.. (S)-duloxetine hydrochloride : A duloxetine hydrochloride in which the duloxetine moiety has S configuration.	2.91	3	0	duloxetine hydrochloride	antidepressant
irinotecan [no description available]	3.01	4	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
valsartan Valsartan: A tetrazole derivative and ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKER that is used to treat HYPERTENSION.. valsartan : A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.	2.86	3	0	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
ziprasidone ziprasidone: a benzisothiazoylpiperazine derivative; has combined dopamine and serotonin receptor antagonist activity; structurally related to tiospirone. ziprasidone : A piperazine compound having 1,2-benzothiazol-3-yl- and 2-(6-chloro-1,3-dihydro-2-oxindol-5-yl)ethyl substituents attached to the nitrogen atoms.	3.83	3	0	1,2-benzisothiazole; indolones; organochlorine compound; piperazines	antipsychotic agent; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; psychotropic drug; serotonergic antagonist
zolmitriptan zolmitriptan: an antimigraine compound; a serotonin (5HT)-1D receptor agonist. zolmitriptan : A member of the class of tryptamines that is N,N-dimethyltryptamine in which the hydrogen at position 5 of the indole ring has been replaced by a [(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl group. A serotonin 5-HT1 B and D receptor agonist, it is used for the treatment of migraine.	2.05	1	0	oxazolidinone; tryptamines	anti-inflammatory drug; serotonergic agonist; vasoconstrictor agent
simendan Simendan: A hydrazone and pyridazine derivative; the levo-form is a phosphodiesterase III inhibitor, calcium-sensitizing agent, and inotropic agent that is used in the treatment of HEART FAILURE.	2.02	1	0
adefovir dipivoxil bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine: structure given in first source. adefovir pivoxil : An organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection.	1.98	1	0	6-aminopurines; carbonate ester; ether; organic phosphonate	antiviral drug; DNA synthesis inhibitor; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent; prodrug
capecitabine Capecitabine: A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.. capecitabine : A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted into its N-(penyloxy)carbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers.	2.6	1	0	carbamate ester; cytidines; organofluorine compound	antimetabolite; antineoplastic agent; prodrug
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	3.49	7	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
nitroaniline nitroaniline: RN given refers to cpd with unspecified locant for nitro moiety. nitroaniline : A substituted aniline that carries one or more nitro groups.	2.69	3	0
octyl gallate [no description available]	2.41	1	0	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
1-n-butylimidazole [no description available]	2.02	1	0
3-n-butylphthalide 3-n-butylphthalide: isolated from phenolic part of Ligusticum wallichii Franch; structure given in first source	2.31	1	0	benzofurans
gadolinium chloride gadolinium chloride: a macrophage inhibitor; reduces pulmonary injury and inflammatory mediator production induced by inhaled ozone	2.03	1	0	gadolinium coordination entity	TRP channel blocker
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	3.14	5	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
ruthenium chloride (rucl3) ruthenium chloride: RN given refers to unlabeled cpd	2.46	2	0
dimethylhydrazines Dimethylhydrazines: Hydrazines substituted with two methyl groups in any position.	2.13	1	0
carfentanil carfentanil : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of methyl 4-anilino-1-(2-phenylethyl)piperidine-4-carboxylate with propanoic acid.	2.17	1	0	methyl ester; piperidines; tertiary amino compound; tertiary carboxamide	mu-opioid receptor agonist; opioid analgesic; tranquilizing drug
cathinone cathinone: alkaloid from khat shrub, Catha edulis; RN given refers to parent cpd without isomeric designation. cathinone : The S stereoisomer of 2-aminopropiophenone.	3.39	6	0	2-aminopropiophenone; monoamine alkaloid	central nervous system stimulant; psychotropic drug
acridine orange Acridine Orange: A cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms.. acridine orange : Fluorescent dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions respectively.. acridine orange free base : A member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.	2.44	2	0	aminoacridines; aromatic amine; tertiary amino compound	fluorochrome; histological dye
ammonium peroxydisulfate ammonium persulfate : An inorganic ammonium salt in which two of the terminal hydroxy groups of peroxydisulfuric acid are deprotonated and associated with ammonium ions as counter-cations.	2.05	1	0
starlicide hydrochloride starlicide: avian toxicant registered to control starlings at cattle and poultry feed lots; RN given refers to parent cpd	2	1	0
potassium phosphate potassium phosphate: used in dental materials and to treat hypophosphatemia; RN given refers to cpd with unspecified MF. tripotassium phosphate : An inorganic potassium salt that is the tripotassium salt of phosphoric acid.	2.1	1	0	inorganic phosphate salt; inorganic potassium salt
caloreen caloreen: glucose polymer with average length of five glucose units for dietary energy supplement. dextrin : Glucans produced by the hydrolysis of starch or glycogen. They are mixtures of polymers of D-glucose units linked by alpha(1->4) or alpha(1->6) glycosidic bonds.	7.53	130	1
daunorubicin hydrochloride [no description available]	2.03	1	0	anthracycline
colestipol Colestipol: Highly crosslinked and insoluble basic anion exchange resin used as anticholesteremic. It may also may reduce triglyceride levels.. colestipol : A high molecular weight copolymer of diethylenetriamine and epichlorohydrin (hydrochloride), with approximately 1 out of 5 amine nitrogens protonated. Due to the highly cross-linked and insoluble nature of the material, no structural formula has been assigned and no specific molecular weight information is available. A basic anion exchange resin, it is used as its hydrochloride for binding bile acids in the intestine, inhibiting their reabsorption.	2.08	1	0
octyl glucoside octyl-beta-D-glucoside: RN given refers to (beta)-isomer. octyl beta-D-glucopyranoside : An beta-D-glucoside in which the anomeric hydrogen of beta-D-glucopyranose is substituted by an octyl group.	3.11	5	0	beta-D-glucoside	plant metabolite
venlafaxine hydrochloride Venlafaxine Hydrochloride: A cyclohexanol and phenylethylamine derivative that functions as a SEROTONIN AND NORADRENALINE REUPTAKE INHIBITOR (SNRI) and is used as an ANTIDEPRESSIVE AGENT.	3.09	4	0	hydrochloride
trazodone hydrochloride Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.	3.45	7	0	hydrochloride	adrenergic antagonist; antidepressant; H1-receptor antagonist; sedative; serotonin uptake inhibitor
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	2.81	3	0	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
2-adamantanol [no description available]	1.99	1	0
1-adamantanol [no description available]	2	1	0
1,3-adamantanedicarboxylic acid [no description available]	2	1	0
adamantanine adamantanine: inhibitor of amino acid transport; RN given refers to parent cpd	2.52	2	0
cyclohexyl methylphosphonofluoridate cyclohexyl methylphosphonofluoridate: acetylcholinesterase inhibitor	3.47	7	0
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	4.35	19	0	D-glucopyranose	epitope; mouse metabolite
anisodamine anisodamine: alkaloid isolated from Chinese solanacea plant	2.02	1	0
mevastatin mevastatin: antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis; structure. mevastatin : A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.	3.52	8	0	2-pyranones; carboxylic ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	antifungal agent; apoptosis inducer; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; fungal metabolite; Penicillium metabolite
terlakiren terlakiren: RN given for (R-(R,S))-isomer	1.99	1	0	peptide
2',7'-dichlorofluorescein 2',7'-dichlorofluorescein: RN given refers to parent cpd	2.13	1	0	2-benzofurans	fluorochrome
ursolic acid [no description available]	3.67	9	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
meglumine antimoniate Meglumine Antimoniate: ANTIMONY salt of meglumine that is used in the treatment of LEISHMANIASIS.	2.95	4	0
norharman norharman: RN given refers to parent cpd. beta-carboline : The parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring.	2.04	1	0	beta-carbolines; mancude organic heterotricyclic parent	fungal metabolite; marine metabolite
cyclam cyclam: RN given refers to parent cpd; structure given in first source	2.44	2	0	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	3.55	8	0	organic bromide salt	colorimetric reagent; dye
betulinic acid [no description available]	2.55	2	0	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
baicalin [no description available]	2.99	4	0	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
oseltamivir Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.. oseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.	2.41	1	0	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic
allicin [no description available]	2.02	1	0	botanical anti-fungal agent; sulfoxide	antibacterial agent
5-methylcytosine 5-Methylcytosine: A methylated nucleotide base found in eukaryotic DNA. In ANIMALS, the DNA METHYLATION of CYTOSINE to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In PLANTS, the methylated sequence is CpNpGp, where N can be any base.. 5-methylcytosine : A pyrimidine that is a derivative of cytosine, having a methyl group at the 5-position.	2.21	1	0	methylcytosine; pyrimidines	human metabolite
thionine thionine: do not confuse with the thionins which is a class of polypeptides; RN above is for the chloride;. thionine : An organic chloride salt composed of 3,7-diaminophenothiazin-5-ium and chloride ions in a 1:1 ratio. A strongly metachromatic dye, useful for the staining of acid mucopolysaccharides. It is also a common nuclear stain and can be used for the demonstration of Nissl substance in nerve cells of the CNS.	2.03	1	0
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	3.87	11	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
cholesteryl sulfate cholesteryl sulfate: component of human seminal plasma & spermatozoa; RN given refers to (3beta)-isomer. cholesterol sulfate : A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3.	3.1	5	0	steroid sulfate	human metabolite
5-dimethylaminonaphthalene-1-sulfonamide [no description available]	2.17	1	0
fluorexon fluorexon: structure	3.16	5	0	xanthene dye	fluorochrome
cholesteryl succinate cholesteryl succinate: RN given refers to (3beta)-isomer. cholesteryl hemisuccinate : A dicarboxylic acid monoester resulting from the formal condensation of the hydroxy group of cholesterol with one of the carboxy groups of succinic acid. A detergent that is often used to replace cholesterol in protein crystallography, biochemical studies of proteins, and pharmacology.	2.25	1	0	cholestane ester; dicarboxylic acid monoester; hemisuccinate	detergent
25-hydroxycholesterol [no description available]	3.89	12	0	25-hydroxy steroid; oxysterol	human metabolite
phenylalanylphenylalanine phenylalanylphenylalanine: RN given refers to (L,L)-isomer	2	1	0
chlorin chlorin: RN given refers to parent cpd; structure. chlorin : A tetrapyrrole fundamental parent that is obtained by formal hydrogenation across the 2,3-double bond of porphyrin.	2.44	2	0
salvin salvin: a biocyclic diterpenoid; from sage and rosemary (Lamiaceae)	2.52	2	0	abietane diterpenoid; carbotricyclic compound; catechols; monocarboxylic acid	angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; food preservative; HIV protease inhibitor; plant metabolite
1,2-distearoyllecithin [no description available]	2.03	1	0
testosterone undecanoate [no description available]	2.17	1	0	steroid ester
5-bromo-4-chloro-3-indolyl beta-galactoside 5-bromo-4-chloro-3-indolyl beta-galactoside: enzyme substrate for beta-galactosidase. 5-bromo-4-chloro-3-indolyl beta-D-galactoside : An indolyl carbohydrate that is the beta-D-galactoside of 3-hydroxy-1H-indole in which the indole moiety is substituted at positions 4 and 5 by chlorine and bromine, respectively. It is used to test for the presence of an enzyme, beta-galactosidase, which cleaved the glycosidic bond to give 5-bromo-4-chloro-3-hydroxy-1H-indole, which immediately dimerises to give an intensely blue product.	2.07	1	0	beta-D-galactoside; D-aldohexose derivative; indolyl carbohydrate; organobromine compound; organochlorine compound	chromogenic compound
nile red nile red : An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.	3.58	8	0	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye
metaperiodate Periodic Acid: A strong oxidizing agent.	2.03	1	0	iodine oxoacid
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.47	2	0
octadecyl rhodamine b chloride octadecyl Rhodamine B chloride: RN & structure given in first source; RN not in Chemline 3/85	2.47	2	0
neocuproine neocuproine: Spectrophotometric determination of copper and ultramicro blood sugar determinations; structure; RN given refers to parent cpd. neocuproine : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.	2.03	1	0	phenanthrolines	chelator; copper chelator
tris(2,2'-bipyridine)ruthenium(II) tris(2,2'-bipyridyl)ruthenium(II): a fluorescent dye; structure in first source	2.15	1	0	ruthenium coordination entity	fluorochrome
surfactin peptide surfactin peptide: antineoplastic product isolated from Bacillus sp.	2.08	1	0
glutathione disulfide Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.	2.15	1	0	glutathione derivative; organic disulfide	Escherichia coli metabolite; mouse metabolite
2-acrylamido-2-methylpropanesulfonate 2-acrylamido-2-methylpropanesulfonate: for detection of alkaline phosphatase; RN given refers to parent cpd; do not confuse with AMPS cpd	2.31	1	0	organosulfonic acid
bathophenanthroline disulfonic acid [no description available]	2.02	1	0
secoisolariciresinol secoisolariciresinol: RN given refers to ((R-(R,R))-isomer); RN for cpd without isomeric designation not available 8/89; precursor of lignans found in human urine; structure given in first source. secoisolariciresinol : A lignan that is butane-1,4-diol in which the 2 and 3 positions are substituted by 4-hydroxy-3-methoxybenzyl groups. (-)-secoisolariciresinol : An enantiomer of secoisolariciresinol having (-)-(2R,3R)-configuration.	2.11	1	0	secoisolariciresinol	antidepressant; phytoestrogen; plant metabolite
cephalosporin c cephalosporin C: RN given refers to parent cpd; structure in Merck, 9th ed, #1937. cephalosporin C : A cephalosporin antibiotic carrying a 3-acetoxymethyl substituent and a 6-oxo-N(6)-L-lysino group at position 7.	3.56	2	0	cephalosporin	fungal metabolite
tetrahydro-11-deoxycortisol tetrahydro-11-deoxycortisol: (3alpha,5beta)-isomer has angiostatic activity	2.38	2	0	21-hydroxy steroid
trioctyl phosphine oxide [no description available]	2.07	1	0
phenosafranine phenosafranine: structure. phenosafranine : An organic chloride salt having 3,7-diamino-5-phenylphenazin-5-ium as the counterion. It is commonly used for staining Gram negative bacteria red in smears to contrast with the blue Gram positive organisms.	2.78	3	0	organic chloride salt	fluorochrome; histological dye; photosensitizing agent
rutecarpine rutacarpine: from Evodia rutaecarpa; an ingredient in zhuyu hewei zhitong capsules	2.1	1	0	beta-carbolines
sertaconazole sertaconazole : A racemate comprising equimolar amounts of (R)- and (S)-sertaconazole. A broad spectrum antifungal with added antipruritic and anti-inflammatory activity used (as its nitrate salt) for treatment of various skin infections.. 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole : A member of the class of imidazoles that carries a 2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl group at position 1.	2.03	1	0	1-benzothiophenes; dichlorobenzene; ether; imidazoles
mizolastine [no description available]	2.03	1	0	benzimidazoles
moguisteine [no description available]	1.98	1	0
pazufloxacin [no description available]	2.03	1	0	quinolines
balofloxacin balofloxacin: showed potent bactericidal activity & inhibited the supercoiling activity of DNA gyrase of S. aureus, E. coli, & P aeruginosa; structure given in first source	2.21	1	0
repaglinide [no description available]	2.49	2	0	piperidines
furnidipine furnidipine: an L-type calcium channel blocker	2.02	1	0
telmisartan Telmisartan: A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.. telmisartan : A member of the class of benzimidazoles used widely in the treatment of hypertension.	2.79	3	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
methacycline [no description available]	2.01	1	0	1,2-diglyceride
adipic dihydrazide [no description available]	2.1	1	0
2-methoxyestradiol 2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.	2.04	1	0	17beta-hydroxy steroid; 3-hydroxy steroid	angiogenesis modulating agent; antimitotic; antineoplastic agent; human metabolite; metabolite; mouse metabolite
perylenediimide perylenediimide: structure in first source. perylenediimide : The 3,4,9,10-tetracarboxylic diimide derivative of perylene.	2.41	1	0	dicarboximide; organic heteropolycyclic compound	fluorochrome
naphthalimides Naphthalimides: Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.	3.04	4	0
4-phenylbenzoic acid 4-phenylbenzoic acid: RN given refers to 4-carboxylic cpd	2.07	1	0
benzeneboronic acid [no description available]	3.32	6	0	boronic acids
2-(n-cyclohexylamino)ethanesulfonic acid 2-(N-cyclohexylamino)ethanesulfonic acid: RN given refers to parent cpd. N-cyclohexyl-2-aminoethanesulfonic acid : An alkanesulfonic acid that is cyclohexanamine in which one of the amino hydrogens is substituted by a 2-sulfoethyl group. It is used as a buffer (pH range of 8.6-10.0) for studying pH-dependent processes in enzymology.	2.44	2	0	alkanesulfonic acid; secondary aliphatic amine	Good's buffer substance
1,7-dioxaspiro(5.5)undecane 1,7-dioxaspiro(5.5)undecane: structure given in first source	1.99	1	0	ketal
1,7-phenanthroline [no description available]	3.64	9	0	phenanthroline
pyrazolo(3,4-d)pyrimidine [no description available]	2.05	1	0
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	8.7	42	2	1,2,3-triazole
lenthionine lenthionine: isolated from the Shiitake mushroom Lenthinus edodes	2.02	1	0	pentathiepane
perfluorobutane sulfonate perfluorobutanesulfonic acid: a surfactant; structure in first source. perfluorobutanesulfonic acid : A perfluoroalkanesulfonic acid that is butane-1-sulfonic acid in which all of the hydrogens of the butyl group have been replaced by fluorines.	2.6	1	0	perfluoroalkanesulfonic acid	surfactant
2,4,6-trihydroxyacetophenone monoacetylphloroglucinol: structure in first source. 2',4',6'-trihydroxyacetophenone : A benzenetriol that is acetophenone in which the hydrogens at positions 2, 4, and 6 on the phenyl group are replaced by hydroxy groups. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of acidic glycans and glycopeptides.	2.05	1	0	aromatic ketone; benzenetriol; methyl ketone	MALDI matrix material; plant metabolite
isoimperatorin isoimperatorin: tumor necrosis factor antagonist isolated from Glehniae root. isoimperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 5. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.	2.06	1	0	psoralens	EC 3.1.1.7 (acetylcholinesterase) inhibitor; metabolite
n,n-carbonyldiimidazole [no description available]	2.77	3	0
2-butynoic acid [no description available]	2.11	1	0
medetomidine Medetomidine: An agonist of RECEPTORS, ADRENERGIC ALPHA-2 that is used in veterinary medicine for its analgesic and sedative properties. It is the racemate of DEXMEDETOMIDINE.	2.17	1	0	imidazoles
sertraline Sertraline: A selective serotonin uptake inhibitor that is used in the treatment of depression.. sertraline : A member of the class of tetralins that is tetralin which is substituted at positions 1 and 4 by a methylamino and a 3,4-dichlorophenyl group, respectively (the S,S diastereoisomer). A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as the hydrochloride salt as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.	4.1	14	0	dichlorobenzene; secondary amino compound; tetralins	antidepressant; serotonin uptake inhibitor
ibuproxam ibuproxam: RN given refers to cpd without isomeric designation; structure in Negwer, 5th ed, #6312. ibuproxam : A hydroxamic acid obtained by formal condensation of the carboxy group of ibuprofen with the amino group of hydroxylamine. Used for treatment of pain and inflammation associated with musculoskeletal and joint disorders.	2.4	2	0	hydroxamic acid	iron chelator; non-narcotic analgesic; non-steroidal anti-inflammatory drug
pirlindole pirlindole: RN given refers to parent cpd; synonym pyrazidol refers to mono-HCl; structure in Negwer, 5th ed, #2812	1.99	1	0	carbazoles
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	4.81	7	1	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
brinzolamide brinzolamide: an antiglaucoma agent	2.08	1	0	sulfonamide; thienothiazine	antiglaucoma drug; EC 4.2.1.1 (carbonic anhydrase) inhibitor
flunoxaprofen flunoxaprofen: structure given in first source. flunoxaprofen : A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group (the S-enantiomer). Although it was shown to be effective in treatment of rheumatoid arthritis and osteoarthritis, the clinical use of flunoxaprofen was discontinued due to possible hepatotoxic side-effects.	2.05	1	0	1,3-benzoxazoles; monocarboxylic acid; organofluorine compound	antirheumatic drug; hepatotoxic agent; non-steroidal anti-inflammatory drug; protein kinase C agonist
drospirenone drospirenone: a progestational compound with antimineralocorticoid and antiandrogenic activity; structure given in first source	3.43	1	1	3-oxo-Delta(4) steroid; steroid lactone	aldosterone antagonist; contraceptive drug; progestin
artemether Artemether: An artemisinin derivative that is used in the treatment of MALARIA.. artemether : An artemisinin derivative that is artemisinin in which the lactone has been converted to the corresponding lactol methyl ether. It is used in combination with lumefantrine as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	2.49	2	0	artemisinin derivative; cyclic acetal; organic peroxide; semisynthetic derivative; sesquiterpenoid	antimalarial
quinocide quinocide: Russian drug; RN given refers to parent cpd; structure	2.75	3	0
trimethyl phosphine [no description available]	1.98	1	0	tertiary phosphine
3,4-diaminobenzoic acid 3,4-diaminobenzoic acid: RN given refers to parent cpd	2.08	1	0
resorufin [no description available]	2.48	2	0	phenoxazine
phenylpropiolic acid phenylpropiolic acid: structure. phenylpropiolic acid : An acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group.	2	1	0	acetylenic compound; alpha,beta-unsaturated monocarboxylic acid; benzenes
ethyl 4-chloro-3-oxobutanoate [no description available]	2.52	2	0
4-bromobenzenesulfonamide 4-bromobenzenesulfonamide: a metabolite of ebrotidine	2.02	1	0
indole-3-carboxylic acid indole-3-carboxylic acid : An indole-3-carboxylic acid carrying a carboxy group at position 3.	2.13	1	0	indol-3-yl carboxylic acid	bacterial metabolite; human metabolite
2,3-diaminonaphthalene [no description available]	2.05	1	0
2,2'-Dihydroxybenzophenone [no description available]	2.03	1	0	benzophenones
fluorone black fluorone Black: structure	2.05	1	0
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	2.44	2	0
emopamil emopamil: prevents renal injury after warm & cold ischemia; RN given refers to cpd without isomeric designation; structure given in first source	1.99	1	0	benzenes; organic amino compound
danofloxacin [no description available]	2.11	1	0	quinolines
dapoxetine [no description available]	2.41	1	0	naphthalenes
masoprocol Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.. masoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.	2.03	1	0	nordihydroguaiaretic acid	antineoplastic agent; hypoglycemic agent; lipoxygenase inhibitor; metabolite
tocophersolan tocophersolan: RN given refers to parent cpd	3	4	0	tocol
trichlorosucrose trichlorosucrose: sweetness intensity roughly 600 times that of sucrose and is nonnutritive and noncaloric; largely unabsorbed in the gastrointestinal tract. sucralose : A disaccharide derivative consisting of 4-chloro-4-deoxy-alpha-D-galactopyranose and 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranose units linked by a glycosidic bond.	3.5	1	1	disaccharide derivative; organochlorine compound	environmental contaminant; sweetening agent; xenobiotic
voriconazole Voriconazole: A triazole antifungal agent that specifically inhibits STEROL 14-ALPHA-DEMETHYLASE and CYTOCHROME P-450 CYP3A.. voriconazole : A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.	9.1	24	2	conazole antifungal drug; difluorobenzene; pyrimidines; tertiary alcohol; triazole antifungal drug	P450 inhibitor
fomocain fomocain: a basic ether with local anesthetic action & relative low toxicity & systemic effects; minor descriptor (77-86); on-line & INDEX MEDICUS search PHENYL ETHERS (77-86); RN given refers to parent cpd	2.02	1	0	amine
aceclofenac [no description available]	2.05	1	0	amino acid; carboxylic ester; dichlorobenzene; monocarboxylic acid; secondary amino compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
prednisolone phosphate prednisolone phosphate: RN given refers to (11 beta)-isomer. prednisolone phosphate : A synthetic glucocorticoid resulting from the formal condensation of the 21-hydroxy group of prednisolone with one of the hydroxy groups of phosphoric acid. It is a prodrug for prednisolone that is activated in vivo by phosphatases.	2.07	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; glucocorticoid; steroid phosphate; tertiary alpha-hydroxy ketone	anti-inflammatory agent; antineoplastic agent; glucocorticoid receptor agonist; prodrug
hesperetin [no description available]	3.36	2	0	3'-hydroxyflavanones; 4'-methoxyflavanones; monomethoxyflavanone; trihydroxyflavanone	antineoplastic agent; antioxidant; plant metabolite
methotrimeprazine Methotrimeprazine: A phenothiazine with pharmacological activity similar to that of both CHLORPROMAZINE and PROMETHAZINE. It has the histamine-antagonist properties of the antihistamines together with CENTRAL NERVOUS SYSTEM effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604). methotrimeprazine : A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.	1.98	1	0	phenothiazines; tertiary amine	anticoronaviral agent; cholinergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; non-narcotic analgesic; phenothiazine antipsychotic drug; serotonergic antagonist
magnolol [no description available]	2.59	2	0	biphenyls
honokiol [no description available]	3.04	4	0	biphenyls
coptisine coptisine: RN given refers to parent cpd	2.07	1	0	alkaloid	metabolite
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.41	1	0	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
alkannin alkannin: a naphthazarin used to promote wound healing, from the plant Alkanna tinctoria; RN given refers to (S)-isomer; structure	2.02	1	0	hydroxy-1,4-naphthoquinone
diphenic anhydride diphenic anhydride: structure given in first source	1.98	1	0
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	2.6	1	0	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
nicosulfuron nicosulfuron: inhibits ACETOLACTATE SYNTHASE; Accent is DuPont brand name. nicosulfuron : A N-sulfonylurea that is 2-(carbamoylsulfamoyl)-N,N-dimethylpyridine-3-carboxamide substituted by a 4,6-dimethoxypyrimidin-2-yl group at the amino nitrogen.	2.05	1	0	N-sulfonylurea; pyridines; pyrimidines	environmental contaminant; herbicide; xenobiotic
echinocystic acid [no description available]	2.13	1	0	triterpenoid
magnoflorine magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.	1.97	1	0	aporphine alkaloid; quaternary ammonium ion	plant metabolite
prochloraz Mirage: a feldspathic porcelain that can be etched & bonded to the tooth. prochloraz : A member of the class of ureas that is 1H-imidazole-1-carboxamide substituted by a propyl and a 2-(2,4,6-trichlorophenoxy)ethyl group at the amino nitrogen atom. A fungicide active against a wide range of diseases affecting field crops, fruit, turf and vegetables.	2.01	1	0	amide fungicide; aromatic ether; conazole fungicide; imidazole fungicide; imidazoles; trichlorobenzene; ureas	antifungal agrochemical; EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor; environmental contaminant; xenobiotic
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	3.76	10	0	carbamate ester; oxazolidinone	metabolite
ceric oxide ceric oxide: RN given refers to cpd with MF CeO2. ceric oxide : A metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis.	2.82	3	0	cerium molecular entity; metal oxide
2-n-propylquinoline 2-propylquinoline: structure in first source	2.11	1	0
bis(diphenylphosphine)ethane [no description available]	2.21	1	0	diphosphanes; tertiary phosphine	allergen
perfluorooctane sulfonic acid perfluorooctane-1-sulfonic acid : A perfluoroalkanesulfonic acid that is octane-1-sulfonic acid in which all seventeen of the hydrogens that are attached to carbons hvae been replaced by fluorines.	2.41	1	0	perfluoroalkanesulfonic acid	antilipemic drug; persistent organic pollutant
atovaquone Atovaquone: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.. atovaquone : A naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position.	2.06	1	0	hydroxy-1,2-naphthoquinone
pyromellitic diimide pyromellitic diimide: RN given refers to parent cpd	2.03	1	0
methylene green methylene green: stain; 4-nitro(methylene blue); RN given refers to chloride. methylene green : An organic chloride salt having 3,7-bis(dimethylamino)-4-nitrophenothiazin-5-ium as the counterion. It stains nuclei green and is sometimes used as a counterstain to red or purple primary stains.	2.1	1	0	organic chloride salt	fluorochrome; histological dye
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.46	2	0	monocarboxylic acid
1-pyrenebutyrate 1-pyrenebutyrate: fluorescent probe; RN given refers to 1-pyrenebutyrate	2.02	1	0
bendamustine hydrochloride [no description available]	2.11	1	0
sulfluramid sulfluramid: delayed-action insecticide against the cockroach Dyctyoptera; Blattelidae germanica. sulfluramid : A sulfonamide obtained by the formal condensation of perfluorooctane-1-sulfonic acid with ethylamine.	2.02	1	0	sulfonamide	acaricide; environmental contaminant; insecticide; xenobiotic
1-benzylimidazole 1-benzylimidazole: inhibits human thromboxane synthetase	2.08	1	0
rivastigmine [no description available]	2.74	3	0	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent
alanylglycine alanylglycine: RN given refers to (L)-isomer	2.03	1	0
n-hydroxysuccinimide N-hydroxysuccinimide: structure	2.9	3	0
tridodecylmethylammonium tridodecylmethylammonium: quaternary amine which forms molecular bond with heparin & can attach firmly to a polyvinyl chloride surface for a nonthrombogenic bypass cannula; RN given refers to chloride	2.13	1	0
2-(4-toluidino)-6-naphthalenesulfonic acid 2-(4-toluidino)-6-naphthalenesulfonic acid: RN given refers to parent cpd; structure	3.27	6	0
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure	3.44	6	0	catechols; primary alcohol	antineoplastic agent; antioxidant; metabolite
1,5-cod 1,5-cyclooctadiene: used in production of Nylon	2.05	1	0
c.i. basic blue 41 [no description available]	2.03	1	0
tert-butyloxycarbonyltryptophan tert-butyloxycarbonyltryptophan: RN given refers to (L)-isomer	1.99	1	0	indolyl carboxylic acid
albendazole sulfoxide albendazole sulfoxide: RN given refers to parent cpd; structure given in first source	3.14	5	0	sulfoxide
ketorolac tromethamine Ketorolac Tromethamine: A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is a non-steroidal anti-inflammatory agent used for analgesia for postoperative pain and inhibits cyclooxygenase activity.. ketorolac tromethamine : An organoammonium salt resulting from the mixture of equimolar amounts of ketorolac and tromethamine (tris). It has potent non-sedating analgesic and moderate anti-inflammatory effects. It is used in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis.	2.11	1	0	organoammonium salt	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor
14-hydroxyclarithromycin 14-hydroxyclarithromycin: major metabolite of A 56268; RN given refers to cpd without isomeric designation	2.04	1	0	aminoglycoside
clarithromycin Clarithromycin: A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit PROTEIN SYNTHESIS in BACTERIA by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.. clarithromycin : The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.	2.77	3	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
3,4-dihydroxymandelic acid 3,4-dihydroxymandelic acid: metabolite of L-dopa; RN given refers to parent cpd without isomeric designation. 3,4-dihydroxymandelic acid : A catechol that is the 3,4-dihydroxy derivative of mandelic acid; a metabolite of L-dopa.	1.98	1	0	2-hydroxy monocarboxylic acid; catechols	antioxidant; drug metabolite; human metabolite; mouse metabolite
tebuconazole Lynx: A genus in the family FELIDAE comprising felines with long legs, ear tufts, and a short tail.. 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol : A tertiary alcohol that is pentan-3-ol substituted by a 4-chlorophenyl, methyl, methyl, and a 1H-1,2,4-triazol-1-ylmethyl at positions 1, 4, 4 and 3 respectively.. tebuconazole : A racemate composed of equimolar amounts of (R)- and (S)-tebuconazole. A fungicide effective against various smut and bunt diseases in cereals and other field crops.	2.03	1	0	monochlorobenzenes; tertiary alcohol; triazoles
raptors imazamox: an experimental imidazolinone herbicide; structure in first source. 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid : A pyridinemonocarboxylic acid that is nicotinic acid which is substituted substituted at position 5 by a methoxymethyl group and at position 2 by a 4,5-dihydro-1H-imidazol-2-yl group, that in turn is substituted by isopropyl, methyl, and oxo groups at positions 4, 4, and 5, respectively.. imazamox : A racemate composed of equimolar amounts of (S)- and (R)-imazamox. An inhibitor of acetohydroxyacid synthase, it is used (particularly as the corresponding ammonium salt, known as imazamox-ammonium) as a herbicide for the control of grass, broad-leaf weeds, and pond weed.	2.66	2	0	ether; imidazolines; imidazolone; pyridinemonocarboxylic acid
cyprodinil cyprodinil: structure in first source. cyprodinil : A member of the class of aminopyrimidine that is N-phenylpyrimidin-2-amine carrying additional cyclopropyl and methyl substituents at positions 4 and 6 respectively. A broad spectrum fungicide used to control a range of pathogens including Tapesia yallundae, Botrytis spp., Alternaria spp. and Rhynchospium secalis. Whilst it is a recognised irritant no serious human health concerns have been identified. It is moderately toxic to birds as well as most aquatic organisms and earthworms, but it is not considered toxic to honeybees.	2.11	1	0	aminopyrimidine; anilinopyrimidine fungicide; cyclopropanes; secondary amino compound	antifungal agrochemical; aryl hydrocarbon receptor agonist; environmental contaminant; xenobiotic
3-hydroxymandelic acid 3-hydroxymandelic acid : A 2-hydroxy monocarboxylic acid that is mandelic acid substituted by a hydroxy group at position 3'.	1.98	1	0	2-hydroxy monocarboxylic acid; phenols	human metabolite
dibenzo-30-crown-10 dibenzo-30-crown-10: structure	2.06	1	0
coenzyme a [no description available]	2.02	1	0	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
5,7-dimethoxyflavone chrysin 5,7-dimethyl ether : A dimethoxyflavone that is the 5,7-dimethyl ether derivative of chrysin.	2.1	1	0	dimethoxyflavone	plant metabolite
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	3.09	5	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
fibrinogen Fibrinogen: Plasma glycoprotein clotted by thrombin, composed of a dimer of three non-identical pairs of polypeptide chains (alpha, beta, gamma) held together by disulfide bonds. Fibrinogen clotting is a sol-gel change involving complex molecular arrangements: whereas fibrinogen is cleaved by thrombin to form polypeptides A and B, the proteolytic action of other enzymes yields different fibrinogen degradation products.. D-iditol : The D-enantiomer of iditol.	2.44	2	0	iditol	fungal metabolite
oxazine 1 oxazine 1: RN & N1 from 9th CI Form Index & given refers to parent cpd	2.07	1	0	organic cation; phenoxazine	fluorochrome
dichlorprop methyl ester [no description available]	2.02	1	0
cholestanol, (3alpha, 5beta)-isomer epicoprostanol: antioxidant; a major constituent of ambergris	2.05	1	0	cholestanoid
equol Equol: A non-steroidal ESTROGEN generated when soybean products are metabolized by certain bacteria in the intestines.	2.08	1	0	hydroxyisoflavans
7-ketocholesterol 7-ketocholesterol: inhibits uptake of cholesterol in rabbit aorta. 7-ketocholesterol : A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7.	2.95	4	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; 7-oxo steroid; cholestanoid	neuroprotective agent
cholest-4-en-3-one cholest-4-en-3-one : A cholestanoid that is cholest-4-ene substituted by an oxo group at position 3.	2	1	0	3-oxo-Delta(4) steroid; cholestanoid	human metabolite; plant metabolite
cadmium telluride cadmium telluride: used in radiation monitoring device	3.02	4	0
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.52	2	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
4-methylumbelliferyl glucuronide 4-methylumbelliferone beta-D-glucuronide : A beta-D-glucosiduronic acid having a 4-methylumbelliferyl substituent at the anomeric position. A hyaluronan synthesis inhibitor, it is anti-tumourigenic for various malignant tumours.	2.06	1	0	beta-D-glucosiduronic acid; coumarins; monosaccharide derivative	antineoplastic agent; chromogenic compound; hyaluronan synthesis inhibitor
alpha,beta-methyleneadenosine 5'-triphosphate alpha,beta-methyleneadenosine 5'-triphosphate: do not confuse with beta,gamma-methylene ATP; RN given refers to parent cpd	2.03	1	0	nucleoside triphosphate analogue
4-hydroxypropranolol 4-hydroxypropranolol: metabolite of propanolol; RN given refers to parent cpd without isomeric designation	2.05	1	0	naphthols
methylglucoside [no description available]	2.41	2	0
salsolinol salsolinol: RN given refers to cpd without isomeric designation; EP to SALSOLINE ALKALOIDS (78-82); on-line search SALSOLINE ALKALOIDS (78-82); Index Medicus search ISOQUINOLINES (78-82). (S)-salsolinol : A 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol that has S-configuration.	3.09	5	0	1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol	human urinary metabolite
5-(3-hydroxyphenyl)-5-phenylhydantoin 5-(3-hydroxyphenyl)-5-phenylhydantoin: metabolite of phenytoin; RN given refers to cpd without isomeric designation	1.98	1	0
gliquidone gliquidone: structure; RN given refers to parent cpd	2.42	2	0	isoquinolines
coronatine coronatine: consists of a coronafacic acid joined by an amide bond to coronamic acid by coronafacate ligase; phytotoxin produced by Pseudomonas syringae; RN given refers to (3aS-(3aalpha,4(1R,2R),6beta,7alpha))-isomer;	2.63	2	0	N-acyl-amino acid
triflumizol triflumizol: structure given in first source. triflumizole : A carboxamidine resulting from the formal condensation of the amino group of 4-chloro-2-(trifluoromethyl)aniline with the oxygen of the acetyl group of N-(propoxyacetyl)imidazole. A sterol demethylation inhibitor, it is used as a fungicide for the control of powdery mildew, scab and other diseases on a variety of crops.	2.01	1	0
chlorfluazuron chlorfluazuron: chitin synthesis inhibitor	2.13	1	0	benzoylurea insecticide; dichlorobenzene; organochlorine insecticide; organofluorine insecticide
mefenacet mefenacet: structure in first source	2.05	1	0	benzothiazoles; tertiary carboxamide	antimitotic; herbicide
hexafluoron hexafluoron: insect growth regulator against mosquito larva; the active agent in Sonet, a Russian product, is hexaflumuron. hexaflumuron : An N-acylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 2,6-difluorobenzoyl group, while a hycrogen attached to the other nitorgen is replaced by a 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl group.	2.13	1	0	aromatic ether; benzoylurea insecticide; dichlorobenzene; N-acylurea; organochlorine insecticide; organofluorine insecticide
delta-tocopherol [no description available]	2.13	1	0	tocopherol; vitamin E	food antioxidant; plant metabolite
taraxerol taraxerol: structure. taraxerol : A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.	2.13	1	0	pentacyclic triterpenoid; secondary alcohol	metabolite
7-amino-4-methylcoumarin 7-amino-4-methylcoumarin: RN given refers to parent cpd	2.11	1	0	7-aminocoumarins	fluorochrome
3-aminobenzeneboronic acid [no description available]	2.07	1	0
tarenflurbil tarenflurbil: R-enantiomer of flurbiprofen but not a COX inhibitor; modulates NF-kB, gamma-secretase, amyloid beta-protein;	2.11	1	0	flurbiprofen
brexanolone brexanolone: a mixture of allopregnanolone and sulfobutylether‐beta‐cyclodextrin for treatment of postpartum depression. brexanolone : A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women.	15.02	54	7	3-hydroxy-5alpha-pregnan-20-one	antidepressant; GABA modulator; human metabolite; intravenous anaesthetic; sedative
melezitose melezitose: structure. melezitose : A trisaccharide produced by insects such as aphids.	2.04	1	0	trisaccharide	animal metabolite
16-dehydropregnenolone 16,17-didehydropregnenolone : A 3beta-hydroxy-Delta(5)-steroid that is pregnenolone with a double bond between positions 16 and 17.	2.15	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; enone
4-nitrophenyl beta-d-glucoside 4-nitrophenyl beta-D-glucoside: RN given refers to (beta)-anomer; see also (alpha)-anomer: 3767-28-0; cpd with unspecified anomer: 5779-46-4. 4-nitrophenyl beta-D-glucoside : A beta-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.	2.11	1	0	beta-D-glucoside; C-nitro compound	chromogenic compound
firefly luciferin Firefly Luciferin: A benzothaizole which is oxidized by LUCIFERASES, FIREFLY to cause emission of light (LUMINESCENCE).. Photinus luciferin : A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.	2.13	1	0	1,3-thiazolemonocarboxylic acid; benzothiazoles; imidothioate	luciferin
alanyltyrosine alanyltyrosine: tyrosine source; RN given refers to (L)-isomer. Ala-Tyr : A dipeptide composed of L-alanine and L-tyrosine joined by a peptide linkage.	2.43	2	0	dipeptide	metabolite
4-nitrophenyl alpha-glucoside 4-nitrophenyl alpha-glucoside: RN given refers to (alpha)-anomer; see also (beta)-anomers: 29857-05-4, 2492-87-7; cpd with unspecified anomer: 5779-46-4. 4-nitrophenyl alpha-D-glucoside : An alpha-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.	2.11	1	0	alpha-D-glucoside; C-nitro compound; monosaccharide derivative	chromogenic compound
aspartyl-phenylalanine aspartyl-phenylalanine: metabolite of aspartame; may inhibit angiotensin converting enzyme; RN given refers to all (L)-isomer	2	1	0	dipeptide	human blood serum metabolite; human xenobiotic metabolite
glycylsarcosine glycylsarcosine : A dipeptide obtained by formal condensation of the carboxy group of glycine with the amino group of sarcosine.	2.31	1	0	dipeptide zwitterion; dipeptide
n-(2-chloro-4-pyridyl)-n'-phenylurea forchlorfenuron : A member of the class of phenylureas that is urea substituted by a phenyl group and a 2-chloropyridin-4-yl group at positions 1 and 3 respectively. It is a plant growth regulator widely used in agriculture for improving fruit quality and fruit size.	2.54	2	0	monochloropyridine; phenylureas	plant growth regulator
pyrimidine dimers Pyrimidine Dimers: Dimers found in DNA chains damaged by ULTRAVIOLET RAYS. They consist of two adjacent PYRIMIDINE NUCLEOTIDES, usually THYMINE nucleotides, in which the pyrimidine residues are covalently joined by a cyclobutane ring. These dimers block DNA REPLICATION.	2.42	2	0
mansonone e mansonone E: a potent anti-bacterial sesquiterpenoid isolated from the dried root bark of Ulmus pumila; structure in first source	2.17	1	0
coumarin 7 coumarin 7: structure in first source	2.31	1	0
oxadiargyl oxadiargyl: an herbicide; structure in first source	2.08	1	0
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	5.7	18	1	D-glucuronic acid	algal metabolite
palmitone palmitone: from leaves of Annona diversifolia; structure in first source. hentriacontan-16-one : A dialkyl ketone that is hentriacontane in which the hydrogens at position 16 are replaced by an oxo group.	2.21	1	0	dialkyl ketone	anticonvulsant; metabolite
diffractaic acid difractaic acid: from Lichen, Usnea steineri; active against Gram-positive, multidrug-resistant bacteria; structure in first source	2.13	1	0	carbonyl compound
1-(4-bromophenyl)ethanol 1-(4-bromophenyl)ethanol: structure in first source	2.03	1	0
hydrobenzoin hydrobenzoin: structure in first source	2.47	2	0	ethanediol
2-phenylsuccinate [no description available]	2.49	2	0
1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid: used as a substitute for amino acids in synthetic peptides	2.07	1	0
2,3-naphthalenedicarboxaldehyde 2,3-naphthalenedicarboxaldehyde: used in colorimetric determination of cholesterol; RN from CA Form Index Vol 90; N1 same as NM	3.13	5	0
nitrophenylgalactosides Nitrophenylgalactosides: Includes ortho-, meta-, and para-nitrophenylgalactosides.. 2-nitrophenyl beta-D-galactoside : A beta-D-galactoside having a 2-nitrophenyl substituent at the anomeric position.	1.99	1	0	beta-D-galactoside; C-nitro compound	chromogenic compound
alanylphenylalanine alanylphenylalanine: RN given refers to (L-Ala-L-PheAla)-isomer	2	1	0	dipeptide	metabolite
10-hydroxycamptothecin [no description available]	2.77	3	0	pyranoindolizinoquinoline
1-(1-naphthyl)ethylamine [no description available]	2.13	1	0
1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid: structure given in first source; RN given refers to cpd without isomeric designation. 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid : A member of the class of beta-carbolines that is 1,2,3,4-tetrahydro-beta-carboline substituted at position 3 by a carboxy group.	2.04	1	0	alpha-amino acid; aromatic amino acid; beta-carboline alkaloid	human urinary metabolite; human xenobiotic metabolite; plant metabolite; rat metabolite
4-acryloylmorpholine 4-acryloylmorpholine: structure in first source	2.05	1	0
diosgenin [no description available]	2.5	2	0	3beta-sterol; hexacyclic triterpenoid; sapogenin; spiroketal	antineoplastic agent; antiviral agent; apoptosis inducer; metabolite
2,2,5,7,8-pentamethyl-1-hydroxychroman 2,2,5,7,8-pentamethyl-1-hydroxychroman: a Vitamin E derivative. chromanol : Any member of the class of chromanes that is chromane substituted by one or more hydroxy groups.	2.31	1	0
combretastatin combretastatin: cytotoxic principle from South African tree COMBRETUM caffrum; structure given in first source; acts at COLCHICINE site of TUBULIN	2.13	1	0
coumarin 6 coumarin 6: structure in first source	2.47	2	0	7-aminocoumarins	fluorochrome
hecogenin acetate hecogenin acetate: structure in first source	2.61	2	0	triterpenoid
2-amino-4-phenylbutyric acid 2-amino-4-phenylbutanoic acid: structure in first source	1.98	1	0
1,2-distearoylphosphatidylethanolamine 1,2-distearoylphosphatidylethanolamine: RN given refers to cpd without isomeric designation. 1,2-distearoylphosphatidylethanolamine : A phosphatidylethanolamine in which the phosphatidyl acyl group at C-1 and C-2 is stearoyl.	2.06	1	0	phosphatidylethanolamine zwitterion; phosphatidylethanolamine	human metabolite
2,3-bis(4-hydroxyphenyl)-propionitrile 2,3-bis(4-hydroxyphenyl)-propionitrile: a selective estrogen receptor beta agonist or modulator. also called DPN compound. 2,3-bis(4-hydroxyphenyl)propionitrile : A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta).	2.07	1	0	nitrile; phenols	estrogen receptor agonist
alanylhistidine alanylhistidine: RN refers to all (L)-isomer	2.02	1	0
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	3.99	12	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	2.05	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
chlorates Chlorates: Inorganic salts of chloric acid that contain the ClO3- ion.	2.43	2	0	chlorine oxoanion; monovalent inorganic anion
enkephalin, d-penicillamine (2,5)- Enkephalin, D-Penicillamine (2,5)-: A disulfide opioid pentapeptide that selectively binds to the DELTA OPIOID RECEPTOR. It possesses antinociceptive activity.. DPDPE : A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond.	2.03	1	0	heterodetic cyclic peptide	delta-opioid receptor agonist
u 73122 1-(6-((3-methoxyestra-1,3,5(10)-trien-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione: structure given in first source. U-73122 : An aza-steroid that is 3-O-methyl-17beta-estradiol in which the 17beta-hydroxy group is replaced by a 6-(maleimid-1-yl)hexylamino group. An inibitor of phospholipase C.	2.06	1	0	aromatic ether; aza-steroid; maleimides	EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor
arginyl-glycyl-aspartic acid arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system	3.18	5	0	oligopeptide
vitamin b 6 Vitamin B 6: VITAMIN B 6 refers to several PICOLINES (especially PYRIDOXINE; PYRIDOXAL; & PYRIDOXAMINE) that are efficiently converted by the body to PYRIDOXAL PHOSPHATE which is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, and aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into PYRIDOXAMINE phosphate. Although pyridoxine and Vitamin B 6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading (EE Snell; Ann NY Acad Sci, vol 585 pg 1, 1990). Most of vitamin B6 is eventually degraded to PYRIDOXIC ACID and excreted in the urine.	2.83	3	0
imipenem, anhydrous Imipenem: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.. imipenem : A broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup.	2.25	1	0	beta-lactam antibiotic allergen; carbapenems; zwitterion	antibacterial drug
cremophor el cremophor EL: solvent for Althesin & Propanidid implicated as possible cause of similar adverse effects polyethoxylated castor oil; RN given refers to cpd with unknown MF; see also records for cremophor & cremophor A	4.69	8	0
alphaxalone alphaxalone: RN given refers to (3alpha,5alpha)-isomer; structure	6.18	9	1	corticosteroid hormone
sr141716 [no description available]	2.06	1	0	amidopiperidine; carbohydrazide; dichlorobenzene; monochlorobenzenes; pyrazoles	anti-obesity agent; appetite depressant; CB1 receptor antagonist
s-nitrosoglutathione [no description available]	2.11	1	0	glutathione derivative; nitrosothio compound	bronchodilator agent; nitric oxide donor; platelet aggregation inhibitor; signalling molecule
eudragit rs Eudragit RS: copolymer of acrylic & methacrylic acid esters & quaternary ammonium groups; used for microcapsules	2.72	3	0
1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1h-imidazole 1-(2-(3-(4-methoxyphenyl)propoxy)-4-methoxyphenylethyl)-1H-imidazole: inhibits platelet aggregation & Ca2+ entry into platelets. SKF-96365 free base : An ether that is 2-(1H-imidazol-1-yl)-1-(4-methoxyphenyl)ethanol in which the hydrogen of the hydroxy group has been substituted by a 3-(4-methoxyphenyl)propyl group.	2.02	1	0	ether; imidazoles; monomethoxybenzene	TRP channel blocker
laurdan laurdan: RN from CA Index Guide	3.14	5	0
paxilline paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.	2.47	2	0	diterpene alkaloid; enone; organic heterohexacyclic compound; terpenoid indole alkaloid; tertiary alcohol	anticonvulsant; Aspergillus metabolite; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor; genotoxin; geroprotector; mycotoxin; Penicillium metabolite; potassium channel blocker
artesunic acid [no description available]	2.52	2	0
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	3.35	6	0
deoxypyridinoline deoxypyridinoline: structure given in first source	2.07	1	0
fura-2-am fura-2-am: pentaester precursor of fura-2	2.13	1	0
thiamethoxam Thiamethoxam: A nitro-oxazine and thiazole derivative that is used as a broad spectrum neonicotinoid insecticide.. thiamethoxam : An oxadiazane that is tetrahydro-N-nitro-4H-1,3,5-oxadiazin-4-imine bearing (2-chloro-1,3-thiazol-5-yl)methyl and methyl substituents at positions 3 and 5 respectively.	2.63	2	0	1,3-thiazoles; 2-nitroguanidine derivative; organochlorine compound; oxadiazane	antifeedant; carcinogenic agent; environmental contaminant; neonicotinoid insectide; xenobiotic
3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate 3-((3-cholamidopropyl)dimethylammonium)-1-propanesulfonate: a surfactant; structure given in first source	2.73	3	0	1,1-diunsubstituted alkanesulfonate
eudragit-e Eudragit-E: a cationic polymer, used as a embolic material for arteriovenous malformations and as a taste masker	2.07	1	0
indoxacarb indoxacarb: oxadiazine insecticide; structure in first source. insecticide : Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	2.31	1	0	methyl ester; organochlorine insecticide	voltage-gated sodium channel blocker
22-hydroxycholesterol [no description available]	2.02	1	0	cholanoid
prodan prodan: do not confuse with prodan in Chemline, RN 16893-85-9 which is disodium hexafluorosilicate	2.08	1	0	2-acyl-6-dimethylaminonaphthalene
racecadotril racecadotril: parenterally active enkephalinase inhibitor	2.1	1	0	N-acyl-amino acid
dimyristoylphosphatidylglycerol [no description available]	2.78	3	0
arginyl-glycyl-aspartyl-serine arginyl-glycyl-aspartyl-serine: corresponds to cell attachment site of fibronectin; located near carboxyl-terminal region of alpha-chain of fibrinogen; inhibits platelet aggregation & fibrinogen binding to activated platelets	2.08	1	0
1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol HU 211: structure given in first source; HU 211 is active & HU 210 is inactive as canibinoids; functional N-methyl-D-aspartate receptor blocker; RN given is for (6aS-trans)-isomer	2.97	1	0
s-benzyl-n-acetyl-l-cysteine S-benzyl-N-acetyl-L-cysteine: RN given refers to (L)-isomer. N-acetyl-S-benzyl-L-cysteine : The S-benzyl derivative of N-acetyl-L-cysteine.	2.21	1	0	organic sulfide; S-substituted N-acetyl-L-cysteine	human urinary metabolite; rat metabolite
1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane: structure in first source	2.11	1	0
procyanidin Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.	2.52	2	0	proanthocyanidin
dityrosine dityrosine: o,o'-biphenol analog of tyrosine; isolated from insoluble protein of human cataractous lenses; structure. dityrosine : A biphenyl compound comprising two tyrosine residues linked at carbon-3 of their benzene rings.	2.17	1	0	biphenyls; non-proteinogenic alpha-amino acid; tyrosine derivative	biomarker
epicatechin gallate epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea. (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida.	2.49	2	0	catechin; gallate ester; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
asulacrine asulacrine: derivative of amsacrine; structure given in first source	2.11	1	0	acridines
daidzin daidzin: a potent, selective, and reversible inhibitor of human mitochondrial aldehyde dehydrogenase. daidzein 7-O-beta-D-glucoside : A glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).	3.33	6	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; monosaccharide derivative	plant metabolite
parinaric acid parinaric acid: long-chain polyenoic fatty acid; RN given refers to cpd without isomeric designation. parinaric acid : An octadecatetraenoic acid containing a conjugated system of double bonds at positions 9, 11, 13 and 15.	2.03	1	0	octadecatetraenoic acid
asiaticoside [no description available]	2.25	1	0
carboxyamido-triazole carboxyamido-triazole: structure given in first source; coccidiostat; U.S. patent No. 4,590,201	2.05	1	0
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	2.01	1	0	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
aristolochic acid ii aristolochic acid II: structure given in first source. aristolochic acid B : An aristolochic acid that is phenanthrene-1-carboxylic acid substituted by a methylenedioxy group at the 3,4 positions and by a nitro group at position 10.	2.43	2	0	aristolochic acids; aromatic ether; C-nitro compound; cyclic acetal; monocarboxylic acid; organic heterotetracyclic compound	carcinogenic agent; metabolite; mutagen; nephrotoxin; toxin
hydroxyitraconazole hydroxyitraconazole: a hydroxylated metabolite of itraconazole; likely contributes importantly to the in vivo activity attributed to itraconazole	6.48	6	3
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	3.12	5	0
coumarin 343 coumarin 343: structure in first source	2.1	1	0	7-aminocoumarins	fluorochrome
tadalafil [no description available]	3.01	4	0	benzodioxoles; pyrazinopyridoindole	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
glycofurol [no description available]	2.39	2	0
anserine Anserine: A dipeptide containing BETA-ALANINE.. anserine : A dipeptide comprising of beta-alanine and 3-methyl-L-histidine units.	2.04	1	0	beta-alanine derivative; dipeptide; zwitterion	animal metabolite; mouse metabolite
1-phenyl-2-decanoylamino-3-morpholino-1-propanol RV 538: noninactivating inhibitor of ceramide-UDPG glucosyltransferase; RN given for unspecified HCl; structure given in first source	2.73	3	0
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	2.01	1	0	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
florfenicol florfenicol: structure given in first source. florfenicol : A carboxamide that is the N-dichloroacetyl derivative of (1R,2S)-2-amino-3-fluoro-1-[4-(methanesulfonyl)phenyl]propan-1-ol. A synthetic veterinary antibiotic that is used for treatment of bovine respiratory disease and foot rot; also used in aquaculture.	2.13	1	0	organochlorine compound; organofluorine compound; secondary alcohol; secondary carboxamide; sulfone	antimicrobial agent
thromboxanes thromboxane : A class of oxygenated oxane derivatives, originally derived from prostaglandin precursors in platelets, that stimulate aggregation of platelets and constriction of blood vessels.	1.97	1	0
dodecyl-beta-d-maltoside dodecyl beta-D-maltoside : A glycoside resulting from attachment of a dodecyl group to the reducing-end anomeric centre of a beta-maltose molecule.	2.75	3	0	disaccharide derivative; glycoside	detergent
tanshinone tanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agent	3.53	8	0	abietane diterpenoid	anticoronaviral agent
protoberberine protoberberine: a benzyltetrahydroisoquinoline derivative that appears as an isoquinoline annelated (adjoined) with a naphthylene; the nitrogen is typically quarternary; nitidine is annelated differently; RN given refers to parent cpd	2.41	1	0
fk 224 FK 224: tachykinin receptor antagonist; structure given in first source	2.01	1	0
taraxasterol taraxasterol: from Cirsium segetum. taraxasterol : A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3.	2.13	1	0	pentacyclic triterpenoid; secondary alcohol	anti-inflammatory agent; metabolite
nitisinone [no description available]	2.31	1	0	(trifluoromethyl)benzenes; C-nitro compound; cyclohexanones; mesotrione	EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor
tafenoquine tafenoquine : A racemate comprising equimolar amounts of (R)- and (S)-tafenoquine.. N(4)-{2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl}pentane-1,4-diamine : An aminoquinoline that is 8-aminoquinoline which is substituted by methoxy groups at positions 2 and 6, a methyl group at position 4, and a m-(trifluoromethyl)phenoxy group at position 5, and in which the amino substituent at position 8 is itself substituted by a 5-aminopentan-2-yl group.	2.47	2	0	(trifluoromethyl)benzenes; aminoquinoline; aromatic ether; primary amino compound; secondary amino compound
silicon phthalocyanine pc4 [no description available]	2.76	3	0
astilbin astilbin: dihydroflavonol from Kohki tea processed from Engelhardtia chrysolepis (huang-qui); astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and is Sweetening Agents; isoastilbin is the (2R-cis)-isomer; structure in first source;. astilbin : A flavanone glycoside that is (+)-taxifolin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.	2.11	1	0	3'-hydroxyflavanones; 4'-hydroxyflavanones; alpha-L-rhamnoside; flavanone glycoside; monosaccharide derivative; tetrahydroxyflavanone	anti-inflammatory agent; plant metabolite; radical scavenger
Prothioconazole-desthio prothioconazole-desthio: desulfurization metabolite of prothioconazole	2.31	1	0	organochlorine compound
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	3.78	10	0	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
parecoxib parecoxib: structure in first source. parecoxib : An N-acylsulfonamide resulting from the formal condensation of valdecoxib with propionic acid. It is a prodrug for valdecoxib.	2.15	1	0	isoxazoles; N-sulfonylcarboxamide	cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
octenyl succinate octenyl succinate: octenyl succinate-modified food starch used as emulsion stabilizer for various food items; RN given refers to parent cpd	3.09	4	0
carboxypolymethylene carbomer: high molecular polyanionic substance	2.46	2	0
n-acetyltyramine N-acetyltyramine: structure given in first source. N-acetyltyramine : A member of the class of tyramines that is tyramine in which one of the hydrogens of the amino group is replaced by an acetyl group.	2.05	1	0	acetamides; tyramines	animal metabolite; Aspergillus metabolite; bacterial metabolite; marine metabolite; quorum sensing inhibitor
titanium tetrafluoride [no description available]	2.08	1	0
1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid 1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid: structure given in first source. DOTA : An azamacrocyle in which four nitrogen atoms at positions 1, 4, 7 and 10 of a twelve-membered ring are each substituted with a carboxymethyl group.	2.1	1	0	azamacrocycle	chelator; copper chelator
2-aminoacridone [no description available]	2.03	1	0	acridines
tenax tenax: porous polymer based on 2,6-diphenyl-p-phenylene oxide; used for trapping volatile organic compounds	3.01	4	0
soyasaponin bb soyasaponin Bb: has activity against polycystic kidney disease; isolated from soybean; structure in first source. soyasaponin I : A triterpenoid saponin that is composed of soyasapogenol B having an alpha-L-rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid moiety attached at the 3-position via a glycosidic linkage.	2.15	1	0	carbohydrate acid derivative; pentacyclic triterpenoid; trisaccharide derivative; triterpenoid saponin	sialyltransferase inhibitor
phytosphingosine phytosphingosine: differ with an additional hydroxyl at C-4 & no double bond between C-4 & C-5	2.05	1	0	amino alcohol; sphingoid; triol	mouse metabolite; Saccharomyces cerevisiae metabolite
7-fluoro-4-nitrobenzo-2-oxa-1,3-diazole [no description available]	2.44	2	0
dx 9065a (2S)-2-(4-(((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy)phenyl)-3-(7-amidino-2-naphtyl)propanoic acid: structure given in first source	2.08	1	0
chapso chapso: RN given refers to (3alpha,5beta,7alpha,12alpha)-isomer	1.98	1	0
gadolinium 1,4,7,10-tetraazacyclododecane-n,n',n'',n'''-tetraacetate gadolinium 1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetate: RN refers to Na salt	2.57	2	0
sulforhodamine 101 [no description available]	2.11	1	0	organic heteroheptacyclic compound	fluorochrome
san 58035 [no description available]	2.42	2	0
kallidin, des-arg(10)- kallidin, des-Arg(10)-: includes both L and D isomers of Phe(8)	2.01	1	0
1-(2',6'-difluorophenyl)-1h,3h-thiazolo(3,4-a)benzimidazole 1-(2',6'-difluorophenyl)-1H,3H-thiazolo(3,4-a)benzimidazole: anti-HIV agent; a non-nucleoside reverse transcriptase inhibitor; structure given in first source	1.98	1	0
celastrol [no description available]	2.31	1	0	monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory drug; antineoplastic agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Hsp90 inhibitor; metabolite
phenoxy radical phenoxy radical : An organic radical generated from phenol.	2.1	1	0	organic radical
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	2.42	2	0	carbene; methanediyl
1-adamantaneacetic acid [no description available]	2.44	2	0
peroxynitrous acid Peroxynitrous Acid: A potent oxidant synthesized by the cell during its normal metabolism. Peroxynitrite is formed from the reaction of two free radicals, NITRIC OXIDE and the superoxide anion (SUPEROXIDES).	2.51	2	0	nitrogen oxoacid
fullerene c60 Fullerenes: A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.. fullerene : A compound composed solely of an even number of carbon atoms, which form a cage-like fused-ring polycyclic system with twelve five-membered rings and the rest six-membered rings. The term has been broadened to include any closed cage structure consisting entirely of three-coordinate carbon atoms.	3.99	13	0	fullerene	geroprotector
imatinib mesylate imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.	3.32	6	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
mk 0663 [no description available]	2.44	2	0	bipyridines; organochlorine compound; sulfone	cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
gefitinib [no description available]	3.2	5	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
7 alpha-hydroxy-4-cholesten-3-one 7 alpha-hydroxy-4-cholesten-3-one: structure. 7alpha-hydroxycholest-4-en-3-one : A cholestanoid consisting of a cholesterol core having an oxo group at the 3-position, a C=C bond at the 4,5-position and an alpha-hydroxy group at the 7-position.	1.98	1	0	3-oxo-Delta(4) steroid; 7alpha-hydroxy steroid; cholestanoid	human metabolite; mouse metabolite
norketamine norketamine: metabolite of ketamine; RN given refers to cpd without isomeric designation	2.74	3	0	organochlorine compound
deltorphin ii, ala(2)- deltorphin II, Ala(2)-: isolated from skin extracts of frogs belonging to the genus Phyllomedusa; has affinity to opioid receptors	2.03	1	0
angiotensin ii, des-phe(8)- Ile(5)-angiotensin II (1-7) : An angiotensin compound consisting of the linear heptapeptide sequence L-Asp-L-Arg-L-Val-L-Tyr-L-Ile-L-His-L-Pro.	2.46	2	0	amino acid zwitterion; angiotensin	vasodilator agent
glycyl-arginyl-glycyl-aspartyl-serine glycyl-arginyl-glycyl-aspartyl-serine: synthetic peptide from fibronectins; inhibits experimental metastasis of murine melanoma cells	2.31	1	0
cyclic adp-ribose Cyclic ADP-Ribose: A pyridine nucleotide that mobilizes CALCIUM. It is synthesized from nicotinamide adenine dinucleotide (NAD) by ADP RIBOSE CYCLASE.	2.04	1	0	cyclic purine nucleotide; nucleotide-sugar	metabolite; ryanodine receptor agonist
naadp nicotinic acid-adenine dinucleotide phosphate : A nicotinic acid dinucleotide that is NADP(+) in which the carboxamide group on the pyridine ring is replaced by a carboxy group.	2.04	1	0	nicotinic acid dinucleotide	calcium channel agonist; metabolite; signalling molecule
27-hydroxycholesterol (25R)-cholest-5-ene-3beta,26-diol : A 26-hydroxycholesterol in which the 25-position has R-configuration.	2.42	2	0	26-hydroxycholesterol	apoptosis inducer; human metabolite; mouse metabolite; neuroprotective agent
desloratadine desloratadine: major metabolite of loratadine. desloratadine : Loratadine in which the ethoxycarbonyl group attached to the piperidine ring is replaced by hydrogen. The major metabolite of loratidine, desloratadine is an antihistamine which is used for the symptomatic relief of allergic conditions including rhinitis and chronic urticaria. It does not readily enter the central nervous system, so does not cause drowsiness.	2.1	1	0	benzocycloheptapyridine	anti-allergic agent; cholinergic antagonist; drug metabolite; H1-receptor antagonist
1-(2-(decylthio)ethyl)azacyclopentane-2-one 1-(2-(decylthio)ethyl)azacyclopentane-2-one: used as a penetration enhancer for topical applications	1.98	1	0
teloxantrone teloxantrone: structure given in first source	1.98	1	0
solutol hs 15 Solutol HS 15: multidrug resistance modification agent in tumor cells; polyoxyethylene esters of 12-hydroxystearic acid; previous RN 105109-85-1	3.87	3	0	aliphatic alcohol
lacto-n-difucohexose ii [no description available]	2.05	1	0
glycerophosphoinositol 4,5-bisphosphate glycerophosphoinositol 4,5-bisphosphate: do not confuse with phosphatidylinositols which have fatty acids esterified at the C-1 and C-2 hydroxyl groups of glycerol	3.29	6	0
dibutyryl cyclic-3',5'-cytidine monophosphate [no description available]	2.04	1	0
3-(4-carboxybenzoyl)-2-quinolinecarboxaldehyde 3-(4-carboxybenzoyl)-2-quinolinecarboxaldehyde: reagent for ultrasensitive determination of primary amines by capillary electrophoresis using laser fluorescence detection; structure given in first source	2.04	1	0	benzoic acids; quinolines	fluorochrome
n-(3,5-dinitrobenzoyl)phenylglycine N-(3,5-dinitrobenzoyl)phenylglycine: RN given for (R)-isomer	1.98	1	0
1,5-anhydrofructose 1,5-anhydrofructose: structure given in first source	2.01	1	0	3-pyrones; anhydrohexose; cyclic ether; cyclic ketone; organic heterocyclic compound; triol
methotrexate [no description available]	4.09	14	0	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent
reboxetine Reboxetine: A morpholine derivative that is a selective and potent noradrenaline reuptake inhibitor; it is used in the treatment of DEPRESSIVE DISORDER.	2.01	1	0	aromatic ether
n-hydroxysuccinimide s-acetylthioacetate N-hydroxysuccinimide S-acetylthioacetate: introduces sulfhydryl groups into proteins; structure given in first source	2.02	1	0
pseudomonas aeruginosa autoinducer Pseudomonas aeruginosa autoinducer: autoinducer required for expression of Pseudomonas aeruginosa virulence genes; structure given in first source. N-(3-oxododecanoyl)homoserine lactone : A N-acyl homoserine lactone that is the monocarboxylic acid amide arising from formal condensation of homoserine lactone with 3-oxododecanoic acid.	2.13	1	0	N-acyl homoserine lactone
delphinidin delphinidin: RN given refers to parent cpd;. delphinidin : An anthocyanidin cation consisting of benzopyrylium with hydroxy substituents at the 3-, 5- and 7-positions and a 3,4,5-trihydroxyphenyl group at the 2-position. It is a plant pigment responsible for the colours of the plants of the genera Viola and Delphinium.	2.31	1	0	5-hydroxyanthocyanidin	antineoplastic agent; biological pigment; plant metabolite
2-iminobiotin 2-iminobiotin: RN given refers to parent cpd(3aS-(3aalpha,4beta,6aalpha))-isomer	3.64	1	1
tamsulosin [no description available]	2.43	2	0	5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide	alpha-adrenergic antagonist; antineoplastic agent
sulperazone sulperazone: combination of above two cpds	2.03	1	0
sulbactam [no description available]	2.03	1	0	penicillanic acids
kca 098 KCA 098: an inhibitor of bone resorption; has no estrogenic activity; structure given in first source	2	1	0
7-(4'-(2-nitroimidazole-1-yl)butyl)theophylline 7-(4'-(2-nitroimidazole-1-yl)butyl)theophylline: a hypoxic-cell radiosensitizer	1.98	1	0
ilomastat CS 610: matrix metalloproteinase inhibitor; structure in first source. ilomastat : An N-acyl-amino acid obtained by formal condensation of the carboxy group of (2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of N-methyl-L-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor	2.02	1	0	hydroxamic acid; L-tryptophan derivative; N-acyl-amino acid	anti-inflammatory agent; antibacterial agent; antineoplastic agent; EC 3.4.24.24 (gelatinase A) inhibitor; neuroprotective agent
osw 1 OSW 1: RN given for the (3beta,16beta)-isomer	2.15	1	0
omega-n-methylarginine omega-N-Methylarginine: A competitive inhibitor of nitric oxide synthetase.. N(omega)-methyl-L-arginine : A L-arginine derivative with a N(omega)-methyl substituent.	2.03	1	0	amino acid zwitterion; arginine derivative; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid
zinquin zinquin: zinquin is an ethyl ester in second source; specific chelator for zinc(II)	2.02	1	0
abiraterone [no description available]	2.08	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; pyridines	antineoplastic agent; EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor
5-carboxyfluorescein diacetate [no description available]	2.17	1	0
n-(3,4-dimethyl-5-isoxazolyl)-4-amino-1,2-naphthoquinone N-(3,4-dimethyl-5-isoxazolyl)-4-amino-1,2-naphthoquinone: structure given in first source	2	1	0
carbapenems [no description available]	2.21	1	0
aspartame [no description available]	2.05	1	0	carboxylic acid; dipeptide zwitterion; dipeptide; methyl ester	apoptosis inhibitor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; environmental contaminant; micronutrient; nutraceutical; sweetening agent; xenobiotic
pomalidomide 3-aminophthalimidoglutarimide: structure in first source	2.13	1	0	aromatic amine; dicarboximide; isoindoles; piperidones	angiogenesis inhibitor; antineoplastic agent; immunomodulator
xylose xylopyranose: structure in first source	2.11	1	0	D-xylose
cd 437 CD 437: selective for retinoic acid receptors gamma. CD437 : A naphthoic acid that is 6-phenylnaphthylene-2-carboxyic acid in which the phenyl substituent has been substituted at positions 3 and 4 by adamant-1-yl and hydroxy groups, respectively. It acts as a selective agonist of retinoic acid receptor (RAR)gamma and induces cell cycle arrest and apoptosis in various cancer cells.	2.06	1	0	adamantanes; monocarboxylic acid; naphthoic acid; phenols	apoptosis inducer; retinoic acid receptor gamma agonist
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	2.05	1	0	beta-lactam antibiotic allergen; beta-lactam
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	3.11	5	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
6-chloro-2-pyridylmethyl nitrate 6-chloro-2-pyridylmethyl nitrate: structure given in first source	1.97	1	0
6-methoxyflavone 6-methoxyflavone: suppresses NFAT-mediated T cell activation; structure in first source	2.17	1	0	ether; flavonoids
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	4.44	20	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
levofloxacin Levofloxacin: The L-isomer of Ofloxacin.. levofloxacin : An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.	2.85	3	0	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor
ezetimibe Ezetimibe: An azetidine derivative and ANTICHOLESTEREMIC AGENT that inhibits intestinal STEROL absorption. It is used to reduce total CHOLESTEROL; LDL CHOLESTEROL, and APOLIPOPROTEINS B in the treatment of HYPERLIPIDEMIAS.. ezetimibe : A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).	2.52	2	0	azetidines; beta-lactam; organofluorine compound	anticholesteremic drug; antilipemic drug; antimetabolite
anthracene-1-carboxylic acid anthracene-1-carboxylic acid: structure in first source	2.31	1	0	anthroic acid
androst-5-en-3-ol androst-5-en-3-ol: RN given refers to (3beta)-isomer	1.99	1	0
cyclohexyl methylphosphonic acid [no description available]	2.5	2	0
nepafenac nepafenac: amide analog of amfenac; structure in first source. nepafenac : A monocarboxylic acid amide that is amfenac in which the carboxylic acid group has been converted into the corresponding carboxamide. It is a prodrug for amfenac, used in eye drops to treat pain and inflammation following cataract surgery.	2.17	1	0	monocarboxylic acid amide	cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug
6-carboxyfluorescein diacetate [no description available]	2.17	1	0
evodiamine [no description available]	2.13	1	0	beta-carbolines
phosphorodithioic acid dithiophosphoric acid : A phosphorothioic acid that is the phosphoric acid having two of its oxygen atoms replaced by sulfur atoms.	2	1	0	phosphorothioic acid
glycylphenylalanine 2-naphthylamide glycylphenylalanine 2-naphthylamide: cathepsin C substrate; RN given refers to (L)-isomer. glycyl-L-phenylalanine 2-naphthylamide : An N-(2-naphthyl)carboxamide obtained by formal condensation of the carboxy group of glycyl-L-phenylalanine with the amino group of 2-naphthylamine.	2	1	0	dipeptide; N-(2-naphthyl)carboxamide	chromogenic compound
moxifloxacin Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.	5.37	4	1	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
dehydrocrotonin dehydrocrotonin: a 19-nor-clerodane diterpene; isolated from the bark of Croton cajucara; structure given in first source	2.45	2	0
naproxen Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.. naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.	6.4	39	1	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
cinacalcet cinacalcet : A secondary amino compound that is (1R)-1-(naphthalen-1-yl)ethanamine in which one of the hydrogens attached to the nitrogen is substituted by a 3-[3-(trifluoromethyl)phenyl]propyl group.	2.17	1	0	(trifluoromethyl)benzenes; naphthalenes; secondary amino compound	calcimimetic; P450 inhibitor
barbigerone barbigerone: an antioxidant; structure in first source	2.1	1	0
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	3.96	12	0	oxygen hydride; oxygen radical; reactive oxygen species
lactitol lactitol : A glycosyl alditol consisting of beta-D-galactopyranose and D-glucitol joined by a 1->4 glycosidic bond. It is used as a laxative, as an excipient, and as replacement bulk sweetener in some low-calorie foods.	2.6	1	0	glycosyl alditol	cathartic; excipient; laxative
naphthalenediimide naphthalenediimide: structure in first source	4.09	4	0
atazanavir sulfate Atazanavir Sulfate: An azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.	2.17	1	0	organic sulfate salt
gallium oxide gallium oxide: RN given refers to unlabeled cpd	2.13	1	0
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	3.89	11	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
cryptotanshinone cryptotanshinone: from Salvia miltiorrhiza	2.72	3	0	abietane diterpenoid	anticoronaviral agent
fenton's reagent Fenton's reagent: used for oxidizing sugars & alcohols	2.55	2	0
carbodiimides Carbodiimides: Compounds with the general formula RN=C=NR, where R is a hydrocarbyl group.. methanediimine : A carbodiimide in which both nitrogens are unsubstituted.	2.78	3	0	carbodiimide
dimethylsulfonioacetate dimethylthetin: synthetic analog of glycine betaine; structure in first source	2.41	1	0	sulfonium betaine
zinc hematoporphyrin [no description available]	2.05	1	0
prostaglandins b Prostaglandins B: Physiologically active prostaglandins found in many tissues and organs. They are potent pressor substances and have many other physiological activities.	1.97	1	0
ampelopsin ampelopsin: hepatoprotective agent; isolated from Hovenia dulcis; RN given for (2R-trans)-isomer; structure in first source. (+)-dihydromyricetin : An optically active form of dihydromyricetin having (2R,3R)-configuration.	2.02	1	0	dihydromyricetin; secondary alpha-hydroxy ketone	antineoplastic agent; antioxidant; metabolite
an-69 AN-69: copolymer of acrylonitrile & sodium methallylsulfonate used in hemodialysis	2.05	1	0
4-hydroxyglutethimide 4-hydroxyglutethimide: structure	2.01	1	0
monodesmethylcitalopram monodesmethylcitalopram: metabolite of citalopram	2.01	1	0	benzenes; organic amino compound
7-thiomethylspirolactone 7-thiomethylspirolactone: spironolactone metabolite; RN refers to (7alpha,17alpha)-isomer; structure given in first source	3.38	1	1
5,6-dehydronorketamine 5,6-dehydronorketamine: metabolite of ketamine; RN given refers to cpd without isomeric designation	2.15	1	0	organochlorine compound
didesmethylcitalopram didesmethylcitalopram: metabolite of citalopram; RN given refers to parent cpd	2.01	1	0	benzenes; organic amino compound
beta-cyclodextrin-benzaldehyde beta-cyclodextrin-benzaldehyde: cyclodextrin compd. with benzaldehyde	3.47	8	0
asenapine asenapine : A racemate consisting of equal amounts of (R,R)- and (S,S)-asenapine. Used as its maleate salt for the acute treatment of schizophrenia and acute treatment of manic or mixed episodes associated with bipolar I disorder with or without psychotic features.. (S,S)-asenapine : A 5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole in which both of the stereocentres have S configuration.	2.55	2	0	5-chloro-2-methyl-2,3,3a,12b-tetrahydrodibenzo[2,3:6,7]oxepino[4,5-c]pyrrole
aminopotentidine aminopotentidine: structure given in first source; RN given refers to the oxalate. aminopotentidine : A benzamide obtained by formal condensation of the carboxy group of 4-aminobenzoic acid with the primary amino group of 1-(2-aminoethyl)-2-cyano-3-{3-[3-(piperidin-1-ylmethyl)phenoxy]propyl}guanidine.	1.99	1	0	aromatic ether; benzamides; guanidines; nitrile; piperidines; substituted aniline	H2-receptor antagonist
tartrazine Tartrazine: An anionic, hydrophilic azo dye with an orange-yellow color used in fabrics, foods and cosmetics, and as a biological stain.. tartrazine : An organic sodium salt which is the trisodium salt of tartrazine acid. A synthetic lemon yellow azo dye used as a food colouring.	2.83	3	0
ferric acetate [no description available]	2.05	1	0
technetium tc 99m pentetate Technetium Tc 99m Pentetate: A technetium imaging agent used in renal scintigraphy, computed tomography, lung ventilation imaging, gastrointestinal scintigraphy, and many other procedures which employ radionuclide imaging agents.	2.06	1	0
1,2-didecanoylphosphatidylcholine 1,2-didecanoylphosphatidylcholine: RN given refers to parent compound	1.99	1	0	1,2-diacyl-sn-glycero-3-phosphocholine
diethylenetriaminetetraacetic acid diethylenetriaminetetraacetic acid: structure given in first source	2.05	1	0
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	2.03	1	0	iodine oxoanion; monovalent inorganic anion
palladium(ii) acetate [no description available]	2.13	1	0
lauroylcarnitine lauroylcarnitine: RN refers to hydroxide inner salt, (R)-isomer. O-lauroyl-L-carnitine : An O-acyl-L-carnitine in which the acyl group is specified as lauroyl (dodecanoyl).	2.06	1	0	dodecanoate ester; O-dodecanoylcarnitine; saturated fatty acyl-L-carnitine
1,2-diphytanoylphosphatidylcholine [no description available]	2.05	1	0
isopulegol isopulegol: isolated from Mentha cardiaca structure in first source	2.08	1	0	p-menthane monoterpenoid	metabolite
terics terics: medicated blocks used for control of cattle bloat; RN given is for teric N; nonylphenol ethoxylate is resistant to environmental breakdown so EPA discourages use	2.46	2	0
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	5.49	14	1	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
angiotensin ii Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).	3.55	8	0	amino acid zwitterion; angiotensin II	human metabolite
campesterol campesterol: RN refers to (3beta,24R)-isomer; structure	2.25	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C28-steroid; phytosterols	mouse metabolite
4-nitrobenzene diazonium tetrafluoroborate 4-nitrobenzene diazonium tetrafluoroborate: used for the analysis of bilirubin; RN given refers to cpd with unspecified nitro locants	2.02	1	0
4-hydroxypraziquantel 4-hydroxypraziquantel: metabolite of praziquantel; structure given in first source	1.99	1	0
1-methyl-3-ethylimidazolium 1-methyl-3-ethylimidazolium: structure given in first source. 1-ethyl-3-methylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is ethyl.	2.05	1	0	1-alkyl-3-methylimidazolium
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	3.39	7	0
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.72	2	0
ropivacaine Ropivacaine: An anilide used as a long-acting local anesthetic. It has a differential blocking effect on sensory and motor neurons.. ropivacaine : The piperidinecarboxamide obtained by the formal condensation of N-propylpipecolic acid and 2,6-dimethylaniline.. (S)-ropivacaine : A piperidinecarboxamide-based amide-type local anaesthetic (amide caine) in which (S)-N-propylpipecolic acid and 2,6-dimethylaniline are combined to form the amide bond.	3.42	7	0	piperidinecarboxamide; ropivacaine	local anaesthetic
sb 203580 [no description available]	2.07	1	0	imidazoles; monofluorobenzenes; pyridines; sulfoxide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector; Hsp90 inhibitor; neuroprotective agent
erlotinib hydrochloride [no description available]	2.58	2	0	hydrochloride; terminal acetylenic compound	antineoplastic agent; protein kinase inhibitor
dihydrodaidzein dihydrodaidzein: structure in first source. dihydrodaidzein : A hydroxyisoflavanone that is isoflavanone carrying two hydroxy substituents located at positions 4' and 7.	2.08	1	0	hydroxyisoflavanone	metabolite
2'-hydroxyflavanone [no description available]	2.53	2	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.54	8	0	divalent inorganic anion; phosphite ion
dioclein dioclein: isolated from the plant Dioclea grandiflora	2.05	1	0
eslicarbazepine acetate eslicarbazepine acetate : The acetate ester, with S configuration, of licarbazepine. An anticonvulsant, it is approved for use in Europe and the United States as an adjunctive therapy for epilepsy.	2.13	1	0	acetate ester; carboxamide; dibenzoazepine; ureas	anticonvulsant; drug allergen
esketamine esketamine : The S- (more active) enantiomer of ketamine.	3.83	3	0	ketamine	analgesic; intravenous anaesthetic; NMDA receptor antagonist
pilocarpic acid pilocarpic acid: hydrolysis product of pilocarpine in aqueous medium; RN given refers to (S-(R,S))-isomer	1.98	1	0
2-nitrophenyl-egta 2-nitrophenyl-EGTA: a photolabile chelator that selectively binds Ca(2+) with high affinity & releases it rapidly upon photolysis; structure given in first source; azid-1 is a caged calcium in which a fluorescent calcium indicator, fura-2, has been modified with an azide substituent on the benzofuran 3-position	2.02	1	0
scutellarin scutellarin: see scutellarein for aglycone. scutellarin : The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.	2.73	3	0	glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative; trihydroxyflavone	antineoplastic agent; proteasome inhibitor
aflatoxin b1 Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.	3.12	5	0	aflatoxin; aromatic ether; aromatic ketone	carcinogenic agent; human metabolite
glycitin glycitin: structure in first source. glycitin : A glycosyloxyisoflavone that is isoflavone substituted by a methoxy group at position 6, a hydroxy group at position 4' and a beta-D-glucopyranosyloxy group at position 7.	2.03	1	0	7-hydroxyisoflavones 7-O-beta-D-glucoside; hydroxyisoflavone; methoxyisoflavone; monosaccharide derivative	plant metabolite
2-deoxygluconic acid 2-deoxy-D-gluconic acid : A derivative of D-gluconic acid lacking the 2-hydroxy group.	1.98	1	0	hexonic acid
7-aminocoumarin 7-amino coumarin: structure in first source	2.03	1	0
1,2,3,4-tetrahydroisoquinoline carboxylic acid 1,2,3,4-tetrahydroisoquinoline carboxylic acid: RN given refers to cpd with locants as specified	2.02	1	0
3,7-diazabicyclo(3.3.1)nonane 3,7-diazabicyclo(3.3.1)nonane: 7-aza analog of azabicyclane; structure	2.41	1	0
maltotriose Porcelite: a light-cured composite resin. alpha-maltotriose : A maltotriose trisaccharide in which the glucose residue at the reducing end is in the pyranose ring form and has alpha configuration at the anomeric carbon atom..	2.68	3	0	maltotriose trisaccharide	human metabolite
etravirine [no description available]	2.15	1	0	aminopyrimidine; aromatic ether; dinitrile; organobromine compound	antiviral agent; HIV-1 reverse transcriptase inhibitor
cucurbit(6)uril cucurbit(6)uril: a macrocyclic cavitand comprising six GLYCOLURIL units; can be used for creating ROTAXANES. cucurbituril : A macrocycle consisting of repeating 2,5-dioxodihydroimidazo[4,5-d]imidazole-1,3,4,6-tetrayl (glycoluril) units linked by methylene groups. The number of glycoluril units in the macrocycle is denoted by the "n" in cucurbit[n]uril name.	2.97	4	0
fe(iii)-edta Fe(III)-EDTA: iron fortifying agent; RN given refers to parent cpd	2.6	1	0	iron coordination entity
3-hydroxy-5-estrane-17-carbonitrile 3-hydroxy-5-estrane-17-carbonitrile: RN refers to (3alpha,5alpha,17beta)-isomer; structure given in first source	2.02	1	0
yh 1885 YH 1885: proton pump inhibitor; structure in first source	2.17	1	0
maropitant maropitant: neurokinin-1 receptor antagonist for treatment and prevention of emesis	4.95	2	1
dronedarone Dronedarone: A non-iodinated derivative of amiodarone that is used for the treatment of ARRHYTHMIA.. dronedarone : A member of the class of 1-benzofurans used for the treatment of cardiac arrhythmias.	2.21	1	0	1-benzofurans; aromatic ether; aromatic ketone; sulfonamide; tertiary amino compound	anti-arrhythmia drug; environmental contaminant; xenobiotic
lapatinib [no description available]	2.6	1	0	furans; organochlorine compound; organofluorine compound; quinazolines	antineoplastic agent; tyrosine kinase inhibitor
arimoclomol arimoclomol: a coinducer of heat shock proteins, delays disease progression in ALS mice	2.21	1	0
darunavir Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.	2.1	1	0	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
dapivirine Dapivirine: effectively prevented human immunodeficiency virus (HIV) infection in cocultures of monocyte-derived dendritic cells and T cells, representing primary targets in sexual transmission	2.1	1	0
sorafenib [no description available]	2.69	2	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; phenylureas; pyridinecarboxamide	angiogenesis inhibitor; anticoronaviral agent; antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; ferroptosis inducer; tyrosine kinase inhibitor
succinobucol succinobucol: monosuccinic acid ester of probucol; a metabolically stable modification of probucol, an equipotent antioxidant to probucol but is pharmacologically distinct	2.13	1	0	benzoate ester; phenols
phenoxodiol phenoxodiol: a synthetic derivative of DAIDZEIN	2.15	1	0
cp 101,606 traxoprodil mesylate: a selective NMDA antagonist; structure given in first source	2.13	1	0
cholic acid Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.. cholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.	3.75	10	0	12alpha-hydroxy steroid; 3alpha-hydroxy steroid; 7alpha-hydroxy steroid; bile acid; C24-steroid; trihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	4.29	18	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
cortisone [no description available]	3.13	5	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
equilin Equilin: An estrogenic steroid produced by HORSES. It has a total of four double bonds in the A- and B-ring. High concentration of euilin is found in the URINE of pregnant mares.	1.98	1	0	17-oxo steroid; 3-hydroxy steroid
cellulose triacetate cellulose triacetate: for hemodialysis filtration	2	1	0
1,1-bis(4-hydroxyphenyl)cyclohexane 1,1-bis(4-hydroxyphenyl)cyclohexane: structure in first source	2.03	1	0	diarylmethane
3-nitrotyrosine 3-nitrotyrosine: RN given refers to parent cpd without isomeric designation. 3-nitrotyrosine : A nitrotyrosine comprising tyrosine having a nitro group at the 3-position on the phenyl ring.	2.77	3	0	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
epinastine dexamethasone acetate: RN given refers to (11beta,16alpha)-isomer	2.4	2	0	corticosteroid hormone
sodium sulfide sodium sulfide: see also record for sodium bisulfide; actisoufre is the sodium sulfide component of sulfur-containing thermal springs which is also found in Saccharomyces cerevisiae	2.44	2	0
propargylamine propargylamine: RN given refers to parent cpd; structure	2.39	2	0
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.6	8	0
noscapine Noscapine: A naturally occurring opium alkaloid that is a centrally acting antitussive agent.. (-)-noscapine : A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.	2.48	2	0	aromatic ether; benzylisoquinoline alkaloid; cyclic acetal; isobenzofuranone; organic heterobicyclic compound; organic heterotricyclic compound; tertiary amino compound	antineoplastic agent; antitussive; apoptosis inducer; plant metabolite
1,3-cyclooctadiene [no description available]	2.05	1	0
wortmannin [no description available]	3.74	10	0	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
nsc281612 NSC281612: antineoplastic; structure in first source	2.02	1	0
lariciresinol lariciresinol: found in human urine. (+)-lariciresinol : A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).	2.11	1	0	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite
medicarpin (-)-medicarpin : The (-)-enantiomer of medicarpin.	2	1	0	medicarpin	plant metabolite
dentatin dentatin: from Clausena excavata; structure in first source	2.13	1	0	coumarins	metabolite
anthricin anthricin: antitumor constituent from Anthriscus sylvestris (L.) Hoffm; structure in first source. deoxypodophyllotoxin : A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group.	2.13	1	0	furonaphthodioxole; gamma-lactone; lignan; methoxybenzenes	antineoplastic agent; apoptosis inducer; plant metabolite
trimethoprim, sulfamethoxazole drug combination Trimethoprim, Sulfamethoxazole Drug Combination: A drug combination with broad-spectrum antibacterial activity against both gram-positive and gram-negative organisms. It is effective in the treatment of many infections, including PNEUMOCYSTIS PNEUMONIA in AIDS.. co-trimoxazole : A two-component mixture comprising trimethoprim and sulfamethoxazole.	2.46	2	0
o-(chloroacetylcarbamoyl)fumagillol O-(Chloroacetylcarbamoyl)fumagillol: Semisynthetic analog of fumagillin (a cyclohexane-sesquiterpene antibiotic isolated from ASPERGILLUS FUMIGATUS) that inhibits angiogenesis.. O-(chloroacetylcarbamoyl)fumagillol : A carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative.	2.39	2	0	carbamate ester; organochlorine compound; semisynthetic derivative; sesquiterpenoid; spiro-epoxide	angiogenesis inhibitor; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; methionine aminopeptidase 2 inhibitor; retinoic acid receptor alpha antagonist
taurochenodeoxycholic acid Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.. taurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.	1.99	1	0	bile acid taurine conjugate	human metabolite; mouse metabolite
calcein am calcein AM: a non-fluorescent compound cleaved to a fluorescent compound by non-specific intracellular esterases. calcein am : An organic heteropentacyclic compound that is calcein in which all four carboxy group hydrogens have been substituted by (acetyloxy)methoxy groups and the hyrodgens of the two hydroxy groups have been substituted by acetyl groups. It is a a non-fluorescent probe cleaved to a fluorescent probe by non-specific intracellular esterases.	2.13	1	0	2-benzofurans; acetate ester; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; xanthene dye	fluorochrome
ritonavir Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.	2.1	1	0	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic
acetogenins Acetogenins: Polyketides of up to a few dozen carbons in length, formed by chain extension of multiple PROPIONATES and oxygenated to form tetrahydrofuran and lactone rings along the length of the chain. They are found in ANNONACEAE and other PLANTS. Related compounds cyclize to MACROLIDES.	2.15	1	0
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	3.52	8	0
daunosamine daunosamine: amino sugar moiety common to adriamycin & daunomycin; RN given refers to (L-lyxo)-isomer; see also ristosamine, (L-ribo)-isomer: 51869-30-8 & acosamine, (L-arabino)-isomer: 41094-24-0; structure	2.25	1	0
permanganate [no description available]	2.44	2	0	manganese oxoacid
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.44	2	0
carboplatin [no description available]	2.78	3	0
anatoxin a anatoxin a: found in Anabaena; was indexed to cyanobacterial toxin (MARINE TOXINS) 1978-2006; also see anatoxin-a(s)	1.98	1	0	tropane alkaloid
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	2.41	2	0	inorganic chloride; lithium salt	antimanic drug; geroprotector
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.95	4	0
xylulose-5-phosphate, (d)-isomer D-xylulose 5-phosphate : The D-enantiomer of xylulose 5-phosphate.	2.1	1	0	xylulose 5-phosphate	Escherichia coli metabolite; mouse metabolite
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.41	2	0	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
bradykinin [no description available]	3.54	8	0	oligopeptide	human blood serum metabolite; vasodilator agent
amylopectin Amylopectin: A highly branched glucan in starch.. amylopectin : A polydisperse highly branched polysaccharide derivative composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage. The chains are joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some 6-phosphate ester groups also may occur. The branches in amylopectin typically contain 24 to 30 glucose residues.	3.43	7	0
hexacyanoferrate iii hexacyanoferrate III: RN given refers to parent cpd	1.97	1	0
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	2.73	3	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
carnosine polaprezinc: stimulates bone growth	2.43	2	0	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
mevalonic acid Mevalonic Acid: A dihydroxy monocarboxylic acid and precursor in the biosynthetic pathway known as the mevalonate pathway, which produces terpenes and steroids that are vital for diverse cellular functions.. mevalonic acid : A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.. (R)-mevalonic acid : The (R)-enantiomer of mevalonic acid.	3.54	8	0	3,5-dihydroxy-3-methylpentanoic acid
raffinose Raffinose: A trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal.. raffinose : A trisaccharide composed of alpha-D-galactopyranose, alpha-D-glucopyranose and beta-D-fructofuranose joined in sequence by 1->6 and 1<->2 glycosidic linkages, respectively.	2.73	3	0	raffinose family oligosaccharide; trisaccharide	mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	3.98	12	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
epiglucan epiglucan: a highly side-chain/branched alkali-insoluble cell wall glucan from fungus such as Epicoccum nigrum, Botrytis cinerea, ascomycetes & basidiomycetes; also isolated S-4001 from Lei Wan (polyporus mylitiae), HA-beta-glucan from mushroom Pleutotus ostreatus (Fr.) Quel., and translam from seaweed Laminaria cichorioides; with commercially important functional properties including emulsification and friction reduction.	2.85	3	0
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	4.83	10	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
vestitone [no description available]	2	1	0	(3R)-2'-hydroxyisoflavanones; hydroxyisoflavanone; methoxyisoflavanone	antibacterial agent; metabolite
pantolactone pantolactone: degradation product of pantothenic acid in liver; RN given refers to (+-)-isomer; structure. (R)-pantolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a hydroxy group at position 3 and two methyl groups at position 4 (the R-stereoisomer).	1.98	1	0	butan-4-olide	Saccharomyces cerevisiae metabolite
theanine theanine: RN given refers to (L)-isomer; precursor of ethylamine; found in green tea. N(5)-ethyl-L-glutamine : A N(5)-alkylglutamine where the alkyl group is ethyl. It has been isolated from green tea.	2.17	1	0	amino acid zwitterion; N(5)-alkyl-L-glutamine	geroprotector; neuroprotective agent; plant metabolite
7-dehydrocholesterol [no description available]	2.13	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; Delta(5),Delta(7)-sterol	human metabolite; mouse metabolite
inositol 1,4,5-trisphosphate Inositol 1,4,5-Trisphosphate: Intracellular messenger formed by the action of phospholipase C on phosphatidylinositol 4,5-bisphosphate, which is one of the phospholipids that make up the cell membrane. Inositol 1,4,5-trisphosphate is released into the cytoplasm where it releases calcium ions from internal stores within the cell's endoplasmic reticulum. These calcium ions stimulate the activity of B kinase or calmodulin.	2.46	2	0	myo-inositol trisphosphate	mouse metabolite
ouabain Ouabain: A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like DIGITALIS. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-EXCHANGING ATPASE.. cardiac glycoside : Steroid lactones containing sugar residues that act on the contractile force of the cardiac muscles.. ouabain : A steroid hormone that is a multi-hydroxylated alpha-L-rhamnosyl cardenoloide. It binds to and inhibits the plasma membrane Na(+)/K(+)-ATPase (sodium pump). It has been isolated naturally from Strophanthus gratus.	2.95	4	0	11alpha-hydroxy steroid; 14beta-hydroxy steroid; 5beta-hydroxy steroid; alpha-L-rhamnoside; cardenolide glycoside; steroid hormone	anti-arrhythmia drug; cardiotonic drug; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; ion transport inhibitor; plant metabolite
taxifolin (+)-taxifolin : A taxifolin that has (2R,3R)-configuration.	2.15	1	0	taxifolin	metabolite
desmosterol Desmosterol: An intermediate in the synthesis of cholesterol.. desmosterol : A cholestanoid that is cholesta-5,24-diene substituted by a beta-hydroxy group at position 3. It is an intermediate metabolite obtained during the synthesis of cholesterol.	2.46	2	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C27-steroid; cholestanoid	human metabolite; mouse metabolite
maltohexaose alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp : A maltohexaose hexasaccharide consisting of five alpha-D-glucopyranose residues and a D-glucopyranose residue joined in sequence by (1->4) glycosidic bonds.	2.7	3	0	maltohexaose hexasaccharide
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	3.31	6	0	tartaric acid	Escherichia coli metabolite
taurolithocholic acid Taurolithocholic Acid: A bile salt formed in the liver from lithocholic acid conjugation with taurine, usually as the sodium salt. It solubilizes fats for absorption and is itself absorbed. It is a cholagogue and choleretic.. taurolithocholic acid : The bile acid taurine conjugate of lithocholic acid.	2.03	1	0	bile acid taurine conjugate; monocarboxylic acid amide	human metabolite
nitroarginine Nitroarginine: An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6). N(gamma)-nitro-L-arginine : An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.	2.41	1	0	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
dehydroascorbic acid Dehydroascorbic Acid: The reversibly oxidized form of ascorbic acid. It is the lactone of 2,3-DIKETOGULONIC ACID and has antiscorbutic activity in man on oral ingestion.. L-dehydroascorbate : An organic anion and the conjugate base of L-dehydroascorbic acid, arising from deprotonation of the acidic C2-position.. L-dehydroascorbic acid : Dehydroascorbic acid having the L-configuration.	2.46	2	0	dehydroascorbic acid; vitamin C	coenzyme; mouse metabolite
cortodoxone Cortodoxone: 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.. 11-deoxycortisol : A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.	2.38	2	0	deoxycortisol; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
arbutin hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.	2.04	1	0	beta-D-glucoside; monosaccharide derivative	Escherichia coli metabolite; plant metabolite
fructans (2->6)-beta-D-fructan : A fructan compound consisting of repeating (2->6)-beta-linked fructofuranose units.	2.75	3	0
cellulase Cellulase: An endocellulase with specificity for the hydrolysis of 1,4-beta-glucosidic linkages in CELLULOSE, lichenin, and cereal beta-glucans.. beta-cellotriose : A cellotriose with a beta-configuration at the anomeric position.	2.98	4	0	cellotriose
meropenem Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.	2.52	2	0	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	3.28	6	0	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	3.27	6	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
digitoxin Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.	1.97	1	0	cardenolide glycoside	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
saquinavir Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.	3.13	5	0	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
netilmicin Netilmicin: Semisynthetic 1-N-ethyl derivative of SISOMYCIN, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity.	2.48	2	0
linezolid [no description available]	3.02	4	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis inhibitor
norpseudoephedrine norpseudoephedrine: major metabolite of diethylpropion in man under acidic urine conditions; RN given refers to cpd without isomeric designation;. cathine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1S,2S-stereoisomer).	2.07	1	0	amphetamines; phenethylamine alkaloid	central nervous system stimulant; plant metabolite; psychotropic drug
phalloidine Phalloidine: Very toxic polypeptide isolated mainly from AMANITA phalloides (Agaricaceae) or death cup; causes fatal liver, kidney and CNS damage in mushroom poisoning; used in the study of liver damage.. phalloidin : A homodetic bicyclic heptapeptide having a sulfide bridge.	2.44	2	0	homodetic cyclic peptide
indican [no description available]	2.89	3	0	beta-D-glucoside; exopolysaccharide; indolyl carbohydrate
ryanodine Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.	2.42	2	0
stevioside stevioside: Kaurene glucoside from leaves of Stevia rebaudiana; 300 times as sweet as sugar. stevioside : A diterpene glycoside that is rubusoside in which the hydroxy group at position 2 of the allylic beta-D-glucoside has been converted to the corresponding beta-D-glucoside. It is a natural herbal sweetener that is 250-300 times sweeter than sucrose (though with a bitter aftertaste), extracted from the Stevia rebaudiana plant native to South America.. diterpene glycoside : A terpene glycoside in which the terpene moiety is a diterpenoid.	2.05	1	0	beta-D-glucoside; bridged compound; diterpene glycoside; ent-kaurane diterpenoid; tetracyclic diterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; hypoglycemic agent; plant metabolite; sweetening agent
patchouli alcohol patchouli alcohol: major component of the essential oil of patchouli; perfumery raw material. patchouli alcohol : A carbotricyclic compound and sesquiterpenoid tertiary alcohol that is tricyclo[5.3.1.0(3,8)]undecan-3-ol which is substituted at positions 2, 2, 6 and 8 by methyl groups (the 1R,3R,6S,7S,8S-diastereoisomer).	2.15	1	0
genipin [no description available]	2.77	3	0	iridoid monoterpenoid	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cross-linking reagent; hepatotoxic agent; uncoupling protein inhibitor
naringin [no description available]	3.19	5	0	(2S)-flavan-4-one; 4'-hydroxyflavanones; dihydroxyflavanone; disaccharide derivative; neohesperidoside	anti-inflammatory agent; antineoplastic agent; metabolite
ochratoxin a ochratoxin A: structure in first source & in Merck, 9th ed, #6549. ochratoxin A : A phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid (ochratoxin alpha). It is among the most widely occurring food-contaminating mycotoxins, produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum.	3.03	4	0	isochromanes; monocarboxylic acid amide; N-acyl-L-phenylalanine; organochlorine compound; phenylalanine derivative	Aspergillus metabolite; calcium channel blocker; carcinogenic agent; mycotoxin; nephrotoxin; Penicillium metabolite; teratogenic agent
cyclopamine [no description available]	2.13	1	0	piperidines	glioma-associated oncogene inhibitor
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.75	9	0
acriflavine Acriflavine: 3,6-Diamino-10-methylacridinium chloride mixt. with 3,6-acridinediamine. Fluorescent dye used as a local antiseptic and also as a biological stain. It intercalates into nucleic acids thereby inhibiting bacterial and viral replication.	2.1	1	0
acetylleucyl-leucyl-norleucinal acetylleucyl-leucyl-norleucinal: a proteasome inhibitor. acetylleucyl-leucyl-norleucinal : A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.	1.99	1	0	aldehyde; tripeptide	cysteine protease inhibitor
n-formylmethionine leucyl-phenylalanine N-Formylmethionine Leucyl-Phenylalanine: A formylated tripeptide originally isolated from bacterial filtrates that is positively chemotactic to polymorphonuclear leucocytes, and causes them to release lysosomal enzymes and become metabolically activated.. N-formyl-L-methionyl-L-leucyl-L-phenylalanine : A tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor.	3.12	5	0	tripeptide
sb 243213 SB 243213: a 5-HT2c inverse agonist; structure in first source	2.01	1	0	indolyl carboxylic acid
diprenorphine Diprenorphine: A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.	2.03	1	0	morphinane alkaloid
plasminogen activator inhibitor 2 N-butyrylhomoserine lactone: quorum sensing compound biosynthesized by LasI protein; structure given in first source	2.13	1	0	N-acyl-amino acid
sodium arsenite sodium arsenite : An inoganic sodium salt with formula with formula NaAsO2.	2.43	2	0	arsenic molecular entity; inorganic sodium salt	antibacterial agent; antifungal agent; antineoplastic agent; carcinogenic agent; herbicide; insecticide; rodenticide
vinpocetine vinpocetine: whole issue of Arzneim Forsch (23 articles) discuss this drug; Arzneim Forsch 26(10a);1976; RN given refers to parent cpd with unspecified isomeric designation	3.4	7	0	alkaloid	geroprotector
sultamicillin sultamicillin: contains ampicillin & sulbactam	2.03	1	0	penicillanic acid ester
loteprednol etabonate Loteprednol Etabonate: An androstadiene derivative corticosteroid that is used as an ANTI-ALLERGIC AGENT for the treatment of inflammatory and allergic eye conditions.	2.15	1	0	11beta-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; etabonate ester; organochlorine compound; steroid acid ester; steroid ester	anti-inflammatory drug
sucrose octasulfate [no description available]	2.17	1	0
maleic acid maleic acid: RN given refers to parent cpd(Z)-isomer which is maleic acid; all RR's given refer to (Z)-isomer; (E)-isomer is fumaric acid. maleic acid : A butenedioic acid in which the double bond has cis- (Z)-configuration.	2.99	4	0	butenedioic acid	algal metabolite; mouse metabolite; plant metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.02	1	0	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2	1	0	cinnamic acid	plant metabolite
ergosterol [no description available]	3.66	9	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	fungal metabolite; Saccharomyces cerevisiae metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	5.21	11	1	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	3.14	5	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	7.78	126	0	cyclodextrin
fumaric acid fumaric acid: see also record for ferrous fumarate; use FUMARATES for general fumaric acid esters. fumaric acid : A butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle.	2.45	2	0	butenedioic acid	food acidity regulator; fundamental metabolite; geroprotector
farnesol Farnesol: A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose. It is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates. It has a delicate odor and is used in perfumery. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). (2-trans,6-trans)-farnesol : The (2-trans,6-trans)-stereoisomer of farnesol.. farnesol : A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.	2.82	2	0	farnesol	plant metabolite
bombykol bombykol: RN given refers to (Z,E)-isomer; structure	2.08	1	0	long-chain primary fatty alcohol	pheromone
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	6.83	22	1	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
retinol Vitamin A: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.. vitamin A : Any member of a group of fat-soluble retinoids produced via metabolism of provitamin A carotenoids that exhibit biological activity against vitamin A deficiency. Vitamin A is involved in immune function, vision, reproduction, and cellular communication.. all-trans-retinol : A retinol in which all four exocyclic double bonds have E- (trans-) geometry.. retinol : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraen-1-ol substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).	3.53	8	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
latrunculin a latrunculin A: 16-membered macrolide attached to 2-thiazolidinone moiety; from Red Sea sponge Latrunculia magnifica; see also latrunculin B; structure given in first source. latrunculin A : A bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica and from the Fiji Islands sponge Cacospongia mycofijiensis. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes.	3.16	5	0	cyclic hemiketal; macrolide; oxabicycloalkane; thiazolidinone	actin polymerisation inhibitor; metabolite; toxin
palmitoleic acid hexadecenoate : A long-chain unsaturated fatty acid anion that is the conjugate base of hexadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	1.99	1	0	hexadec-9-enoic acid	algal metabolite; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; human blood serum metabolite
oleic acid Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.	4.3	18	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	3.31	6	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
farnesyl pyrophosphate farnesyl pyrophosphate: a sesquiterpene that dimerizes to SQUALENE; RN given refers to cpd without isomeric designation. 2-trans,6-trans-farnesyl diphosphate : The trans,trans-stereoisomer of farnesyl diphosphate.	2.08	1	0	farnesyl diphosphate	Escherichia coli metabolite; mouse metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	3.09	4	0	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
pectins Pectins: High molecular weight polysaccharides present in the cell walls of all plants. Pectins cement cell walls together. They are used as emulsifiers and stabilizers in the food industry. They have been tried for a variety of therapeutic uses including as antidiarrheals, where they are now generally considered ineffective, and in the treatment of hypercholesterolemia.. alpha-D-galacturonic acid : The alpha-anomer of D-galacturonic acid.	3.72	9	0	D-galactopyranuronic acid
cerivastatin cerivastatin: cerivastatin is the ((E)-(+))-isomer; structure given in first source. cerivastatin : (3R,5S)-3,5-dihydroxyhept-6-enoic acid in which the (7E)-hydrogen is substituted by a 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl group. Formerly used (as its sodium salt) to lower cholesterol and prevent cardiovascular disease, it was withdrawn from the market worldwide in 2001 following reports of a severe form of muscle toxicity.	2.08	1	0	dihydroxy monocarboxylic acid; pyridines; statin (synthetic)
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	5.86	8	1	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	2.47	2	0	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
thapsigargin Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.	3.56	8	0	butyrate ester; organic heterotricyclic compound; sesquiterpene lactone	calcium channel blocker; EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	2.79	3	0	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
mupirocin Mupirocin: A topically used antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.. mupirocin : An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.	2.1	1	0	alpha,beta-unsaturated carboxylic ester; epoxide; monocarboxylic acid; oxanes; secondary alcohol; triol	antibacterial drug; bacterial metabolite; protein synthesis inhibitor
lycopene [no description available]	3.14	5	0	acyclic carotene	antioxidant; plant metabolite
geranylgeranyl pyrophosphate geranylgeranyl pyrophosphate: RN given refers to (E,E,E)-isomer. geranylgeranyl diphosphate : A polyprenol diphosphate having geranylgeranyl as the polyprenyl component.. 2-trans,6-trans,10-trans-geranylgeranyl diphosphate : The all-trans-isomer of geranylgeranyl diphosphate.	2.44	2	0	geranylgeranyl diphosphate	mouse metabolite
t0901317 T0901317: an LXRalpha and LXRbeta agonist	2.03	1	0
y 27632 Y 27632: RN given for di-HCl salt; inhibits Rho-associated protein kinase; inhibits calcium sensitization to affect smooth muscle relaxation; structure in first source. Y-27632 : A monocarboxylic acid amide that is trans-[(1R)-1-aminoethyl]cyclohexanecarboxamide in which one of the nitrogens of the aminocarbony group is substituted by a pyridine nucleus. It has been shown to exhibit inhibitory activity against Rho-associated protein kinase (ROCK) enzyme.	2.47	2	0	aromatic amide
benzoylecgonine benzoylecgonine: cocaine is benzoyl methyl ecgonine; RN given refers to (1R-(exo,exo))-isomer; structure. ecgonine benzoate : A benzoate ester metabolite of cocaine formed by hydrolysis of the methyl ester group, catalysed by carboxylesterases.	2.11	1	0	benzoate ester; tropane alkaloid	epitope; human xenobiotic metabolite; marine xenobiotic metabolite; plant metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	2.05	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
roflumilast [no description available]	3.56	1	1	aromatic ether; benzamides; chloropyridine; cyclopropanes; organofluorine compound	anti-asthmatic drug; phosphodiesterase IV inhibitor
h 89 N-(2-(4-bromocinnamylamino)ethyl)-5-isoquinolinesulfonamide: structure given in first source. N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A member of the class of isoquinolines that is the sulfonamide obtained by formal condensation of the sulfo group of isoquinoline-5-sulfonic acid with the primary amino group of N(1)-[3-(4-bromophenyl)prop-2-en-1-yl]ethane-1,2-diamine. It is a protein kinase A inhibitor.. (E)-N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide : A N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide in which the double bond adopts a trans-configuration.	2.73	3	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
imidazolidines [no description available]	2.25	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
thymopentin Thymopentin: Synthetic pentapeptide corresponding to the amino acids 32-36 of thymopoietin and exhibiting the full biological activity of the natural hormone. It is an immunomodulator which has been studied for possible use in the treatment of rheumatoid arthritis, AIDS, and other primary immunodeficiencies.	1.98	1	0	oligopeptide
decitabine [no description available]	2.07	1	0	2'-deoxyribonucleoside
colfosceril palmitate colfosceril palmitate: used in the treatment of unilateral pulmonary interstitial emphysema; component of Exosurf. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine : A phosphatidylcholine 32:0 in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl). A synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of pulmonary surfactants.	2.17	1	0	1-acyl-2-hexadecanoyl-sn-glycero-3-phosphocholine; phosphatidylcholine 32:0	mouse metabolite; surfactant
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	3.18	5	0
pa 824 pretomanid: nitroimidazopyran derived from 5-nitroimidazoles; a prodrug that requires activation by a bacterial F420-depedent glucose-6-phosphate dehydrogenase (Fgd) and nitroreductase to activate components that then inhibit bacterial mycolic acid and protein synthesis; structure in first source	2.25	1	0
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	2.04	1	0	actinomycin	mutagen
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	3.18	5	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
melphalan Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.	3.32	6	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.15	1	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	2.05	1	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
u 100480 U 100480: structure given in first source	2.21	1	0
schizandrin schizandrin: a dibenzocyclooctadiene lignan; schizandra is the plant name	2.21	1	0
posaconazole [no description available]	3.05	4	0	aromatic ether; conazole antifungal drug; N-arylpiperazine; organofluorine compound; oxolanes; triazole antifungal drug; triazoles	trypanocidal drug
rubitecan rubitecan: RN refers to (+-)-isomer; anti-HIV agent; DNA Topoisomerases, Type I inhibitor. rubitecan : A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.	2.46	2	0	C-nitro compound; delta-lactone; pyranoindolizinoquinoline; semisynthetic derivative; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
terameprocol [no description available]	2.03	1	0	lignan
shikonin shikonin: a naphthazarin; has antineoplastic and angiogenesis inhibiting activities	2.49	2	0	hydroxy-1,4-naphthoquinone
favipiravir favipiravir : A member of the class of pyrazines that is pyrazine substituted by aminocarbonyl, hydroxy and fluoro groups at positions 2, 3 and 6, respectively. It is an anti-viral agent that inhibits RNA-dependent RNA polymerase of several RNA viruses and is approved for the treatment of influenza in Japan.	2.6	1	0	hydroxypyrazine; organofluorine compound; primary carboxamide	anticoronaviral agent; antiviral drug; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor
riboflavin vitamin B2 : Any member of a group of vitamers that belong to the chemical structural class called flavins that exhibit biological activity against vitamin B2 deficiency. Symptoms associated with vitamin B2 deficiency include glossitis, seborrhea, angular stomaitis, cheilosis and photophobia. The vitamers include riboflavin and its phosphate derivatives (and includes their salt, ionised and hydrate forms).	2.96	4	0	flavin; vitamin B2	anti-inflammatory agent; antioxidant; cofactor; Escherichia coli metabolite; food colouring; fundamental metabolite; human urinary metabolite; mouse metabolite; photosensitizing agent; plant metabolite
likviriton liquiritin: isoalted from Glycyrrhizae radix. liquiritin : A flavanone glycoside that is liquiritigenin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage.	2.41	1	0	beta-D-glucoside; flavanone glycoside; monohydroxyflavanone; monosaccharide derivative	anti-inflammatory agent; anticoronaviral agent; plant metabolite
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	2.02	1	0
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	2.42	2	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
sodium chlorate sodium chlorate : An inorganic sodium salt that has chlorate as the counter-ion. An oxidising agent, it is used for bleaching paper and as a herbicide. It is also used in the manufacture of dyes, explosives and matches.	2.43	2	0	chlorate salt; inorganic sodium salt	herbicide
sodium acetate, anhydrous Sodium Acetate: The trihydrate sodium salt of acetic acid, which is used as a source of sodium ions in solutions for dialysis and as a systemic and urinary alkalizer, diuretic, and expectorant.	2.01	1	0	organic sodium salt	NMR chemical shift reference compound
ammonium acetate ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.	3.15	5	0	acetate salt; ammonium salt	buffer; food acidity regulator
zn(ii)-phthalocyanine [no description available]	2.83	3	0	metallophthalocyanine; zinc tetrapyrrole	fluorochrome
spathulenol spathulenol: sesquiterpene alcohol isolated from essential oils of Artemisia vulgaris L. & Artemisia dracunculus L.. spathulenol : A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7.	2.13	1	0
dipyrone Dipyrone: A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE.. metamizole sodium : An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic.	3.08	1	0	organic sodium salt	anti-inflammatory agent; antipyretic; antirheumatic drug; cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug; prodrug
oxazolidine oxazolidine: structure given in first source	1.99	1	0	oxazolidine
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.46	2	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
11-mercaptoundecanoic acid [no description available]	2.57	2	0
calix(4)arene calix(4)arene: a cyclophane consisting of four phenolic units linked by methylene groups; structure in first source	2.98	4	0
2-vinyl-4,6-diamino-1,3,5-triazine 2-vinyl-4,6-diamino-1,3,5-triazine: used to create a DNA-imprinted polymer; structure in first source	2.08	1	0
mansonone g [no description available]	2.21	1	0
tolfenamic acid tolfenamic acid: structure. tolfenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 3-chloro-2-methylphenyl group. Tolfenamic acid is used specifically for relieving the pain of migraine. It also shows anticancer activity.	2	1	0	aminobenzoic acid; organochlorine compound; secondary amino compound	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; EC 2.7.1.33 (pantothenate kinase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
desmethylclomipramine desmethylclomipramine: RN given refers to parent cpd	2.17	1	0	dibenzoazepine
alpha-asarone asarone: structure in Merck Index, 9th ed, #847. asarone : A phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus.. alpha-asarone : The trans-isomer of asarone.	2.03	1	0	asarone	anticonvulsant; GABA modulator
rhapontin rhapontin: constituent of rhubarb rhizome	2.08	1	0	rhaponticin	angiogenesis inhibitor; anti-allergic agent; anti-inflammatory agent; antilipemic drug; antineoplastic agent; apoptosis inducer; EC 2.3.1.85 (fatty acid synthase) inhibitor; hypoglycemic agent; neuroprotective agent; plant metabolite
cinnamaldehyde 3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.	3.78	8	0	3-phenylprop-2-enal; cinnamaldehydes	antifungal agent; EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor; flavouring agent; hypoglycemic agent; plant metabolite; sensitiser; vasodilator agent
elaidic acid [no description available]	2.21	1	0	octadec-9-enoic acid	food component
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.52	2	0	4-coumaric acid	food component; mouse metabolite; plant metabolite
anethole anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.	2.54	2	0	anethole	flavouring agent
geraniol [no description available]	2.04	1	0	3,7-dimethylocta-2,6-dien-1-ol; monoterpenoid; primary alcohol	allergen; fragrance; plant metabolite; volatile oil component
glycosides [no description available]	4.04	14	0
chalcone trans-chalcone : The trans-isomer of chalcone.	3.16	5	0	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed)	6.9	85	0	isomethyleugenol
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	2.61	2	0	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
retinaldehyde Retinaldehyde: A diterpene derived from the carotenoid VITAMIN A which functions as the active component of the visual cycle. It is the prosthetic group of RHODOPSIN (i.e., covalently bonded to ROD OPSIN as 11-cis-retinal). When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer.. all-trans-retinal : A retinal in which all four exocyclic double bonds have E- (trans-) geometry.	1.99	1	0	retinal; vitamin A	gap junctional intercellular communication inhibitor; human metabolite; mouse metabolite
piperine piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.	2.31	1	0	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
retinol acetate retinol acetate: structure given in first source	2.11	1	0	acetate ester
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	7.42	41	1	stilbene
isoliquiritigenin [no description available]	2.11	1	0	chalcones	antineoplastic agent; biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; GABA modulator; geroprotector; metabolite; NMDA receptor antagonist
phenyl-n-tert-butylnitrone phenyl-N-tert-butylnitrone: a spin-trapping agent	2.03	1	0
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	3.14	5	0	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
cocaethylene cocaethylene: RN given refers to (1R-(exo,exo))-isomer; cocaine metabolite produced in vivo when cocaine and ethanol are taken together; as potent as cocaine in blocking uptake of the neurotransmitter dopamine synapses	2.11	1	0	benzoate ester
cannabidiol Cannabidiol: Compound isolated from Cannabis sativa extract.. cannabidiol : An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.	2.73	3	0	olefinic compound; phytocannabinoid; resorcinols	antimicrobial agent; plant metabolite
buprenorphine Buprenorphine: A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.. buprenorphine : A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.	2.52	2	0	morphinane alkaloid	delta-opioid receptor antagonist; kappa-opioid receptor antagonist; mu-opioid receptor agonist; opioid analgesic
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	2.76	3	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	2.06	1	0	diphosphate ion
dodecylphosphocholine dodecylphosphocholine: phospholipase A2 inhibitor; RN refers to chloride. dodecylphosphocholine : A phosphocholine that is the monododecyl ester of phosphocholine	3.64	2	0	phosphocholines	detergent
polidocanol Polidocanol: An alkyl polyglycol ether of LAURYL ALCOHOL, chemically defined as an alcohol ethoxylate having an average alkyl chain of 12–14 carbon atoms, and an ethylene oxide chain of 9 ethylene oxide units. It is used as a detergent, and medically as a local anesthetic, and as a sclerosing agent for the treatment of ESOPHAGEAL AND GASTRIC VARICES and VARICOSE VEINS.. polidocanol : A hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group.	3.42	7	0	hydroxypolyether	hepatotoxic agent; nonionic surfactant; sclerotherapy agent
sodium metabisulfite sodium metabisulfite: request from searcher; RN given refers to disulfurous acid, di-Na salt. sodium disulfite : An inorganic sodium salt composed of sodium and disulfite ions in a 2:1 ratio.	2.44	2	0	inorganic sodium salt	food antioxidant
tram 34 TRAM 34: inhibits IKCa1; structure in first source	2.03	1	0	organochlorine compound
prednisolone hemisuccinate prednisolone hemisuccinate: RN given refers to (11 beta)-isomer. prednisolone succinate : A hemisuccinate resulting from the formal condensation of the 21-hydroxy group prednisolone with one of the carboxy groups of succinic acid. It is used to treat mild to moderate non-infectious eye allergies and inflammation, including damage caused by chemical and thermal burns.	2	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; hemisuccinate; tertiary alpha-hydroxy ketone	anti-inflammatory drug
leuprolide Leuprolide: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.. leuprolide : An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.	2.53	2	0	oligopeptide	anti-estrogen; antineoplastic agent; gonadotropin releasing hormone agonist
sesquiterpenes [no description available]	6.15	29	1
etomidate Etomidate: Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic.. etomidate : The ethyl ester of 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. It is an intravenous general anaesthetic with no analgesic activity.	4.09	3	1	ethyl ester; imidazoles	intravenous anaesthetic; sedative
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	2.46	2	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
3,3',4,5'-tetrahydroxystilbene 3,3',4,5'-tetrahydroxystilbene: demethyl derivative of isorhapontigenin; structure in first source; a Syk kinase inhibitor; found in heartwood of FABACEAE; inhibitor of photosynthesis in spinach chloroplasts; may be inhibitor of plant growth; RN given refers to (E)-isomer. piceatannol : A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.	2.5	2	0	catechols; polyphenol; resorcinols; stilbenol	antineoplastic agent; apoptosis inducer; geroprotector; hypoglycemic agent; plant metabolite; protein kinase inhibitor; tyrosine kinase inhibitor
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	3.61	8	0	caffeic acid	geroprotector; mouse metabolite
diphenylthiourea N,N'-diphenylthiourea : Thiourea in which each nitrogen carries a phenyl substituent.	2.03	1	0	thioureas	allergen
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2.1	1	0	methoxycinnamic acid
4-(4-dimethylaminostyryl)-1-methylpyridinium 4-(4-dimethylaminostyryl)-1-methylpyridinium: fluorescent probe for living cells; structure in first source. 4-[4-(dimethylamino)styryl]-N-methylpyridinium : A pyridinium cation obtained by methylation at position 1 of 4-(4-dimethylaminostyryl)pyridine	2.03	1	0	pyridinium ion
ethyl ferulate ethyl ferulate: structure in first source	2.25	1	0
4-acetylaminostilbene 4-acetylaminostilbene: RN given refers to non-specified isomer	1.98	1	0
flunarizine Flunarizine: Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 blocking activity. It is effective in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy.	2	1	0	diarylmethane
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	7.39	95	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	2.15	1	0	thiazolidinone
thiohydantoins Thiohydantoins: Sulfur analogs of hydantoins with one or both carbonyl groups replaced by thiocarbonyl groups.	2.08	1	0
triethylammonium cation triethylammonium ion : An organoammonium cation having three ethyl substituents on the nitrogen atom.	2.07	1	0	ammonium ion derivative
cinnarizine Cinnarizine: A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.	3.59	9	0	diarylmethane; N-alkylpiperazine; olefinic compound	anti-allergic agent; antiemetic; calcium channel blocker; geroprotector; H1-receptor antagonist; histamine antagonist; muscarinic antagonist
sulindac Sulindac: A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.. sulindac : A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.	2.41	2	0	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	5.39	13	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
enclomiphene Enclomiphene: The trans or (E)-isomer of clomiphene.	1.99	1	0
levocetirizine [no description available]	2.76	3	0	diarylmethane
Jasmone jasmone: RN refers to (Z)-isomer; structure given in first source	2.1	1	0	cyclic ketone
epalrestat epalrestat : A monocarboxylic acid that is 1,3-thiazolidine which is substituted on the nitrogen by a carboxymethyl group, at positions 2 and 4 by thioxo and oxo groups, respectively, and at position 5 by a 2-methyl-3-phenylprop-2-en-1-ylidene group. It is an inhibitor of aldose reductase (which catalyses the conversion of glucose to sorbitol) and is used for the treatment of some diabetic complications, including neuropathy.	2.15	1	0	monocarboxylic acid; thiazolidines	EC 1.1.1.21 (aldehyde reductase) inhibitor
aurapten aurapten: RN refers to (E)-isomer; structure given in first source. auraptene : A member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties.	2.49	2	0	coumarins; monoterpenoid	antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; dopaminergic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; gamma-secretase modulator; gastrointestinal drug; hepatoprotective agent; matrix metalloproteinase inhibitor; neuroprotective agent; plant metabolite; PPARalpha agonist; vulnerary
n-glycylalanine Gly-Ala : A dipeptide formed from glycine and L-alanine residues.	2.03	1	0	dipeptide	metabolite
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	2.07	1	0
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	3.32	6	0	cinnamate ester; tannin	food component; plant metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	2.15	1	0	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
thiobarbituric acid thiobarbituric acid: RN given refers to parent cpd. 2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur.	2.71	3	0	barbiturates	allergen; reagent
s-phenyl-n-acetylcysteine S-phenyl-N-acetylcysteine: found in urine of rats exposed to benzene; RN given refers to (L)-isomer; RN for cpd without isomeric designation not available 4/88	2.21	1	0	aryl sulfide; S-substituted N-acetyl-L-cysteine	biomarker; human urinary metabolite
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	3.16	5	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
safranine t safranin O : An organic chloride salt having 3,7-diamino-2,8-dimethyl-5-phenylphenazin-5-ium as the counterion. It is commonly used for staining Gram negative bacteria.	2.58	2	0	organic chloride salt	fluorochrome; histological dye
sodium propionate sodium propionate: was term of propionic acid (1986-2006). sodium propionate : An organic sodium salt comprising equal numbers of sodium and propionate ions.	2.06	1	0	organic sodium salt	antifungal drug; food preservative
D-fructopyranose [no description available]	3.56	8	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
sodium ethoxide sodium ethoxide : An organic monosodium salt that has ethoxide as the counterion.	2.03	1	0	organic sodium salt	nucleophilic reagent
tempo TEMPO: structure. TEMPO : A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.	2.98	4	0	aminoxyls; piperidines	catalyst; ferroptosis inhibitor; radical scavenger
ferric ferrocyanide ferric ferrocyanide: antidote to thallium poisoning; RN given refers to Fe(+3)[3:4] salt; structure	2.78	3	0
brij-58 Cetomacrogol: Non-ionic surfactant of the polyethylene glycol family. It is used as a solubilizer and emulsifying agent in foods, cosmetics, and pharmaceuticals, often as an ointment base, and also as a research tool.	2.42	2	0
5-doxylstearate [no description available]	2.44	2	0	aminoxyls
succimer Succimer: A mercaptodicarboxylic acid used as an antidote to heavy metal poisoning because it forms strong chelates with them.. succimer : A sulfur-containing carboxylic acid that is succinic acid bearing two mercapto substituents at positions 2 and 3. A lead chelator used as an antedote to lead poisoning.	2.21	1	0	dicarboxylic acid; dithiol; sulfur-containing carboxylic acid	chelator
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.02	1	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
capsazepine capsazepine: modified capsaicin molecule; a capsaicin receptor antagonist. capsazepine : A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.	2.1	1	0	benzazepine; catechols; monochlorobenzenes; thioureas	capsaicin receptor antagonist
fumonisin b1 fumonisin B1: isolated from Fusarium moniliforme MRC 826; structure given in first source; has cancer-promoting activity; inhibits ceramide synthase. fumonisin B1 : A diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol.	3.29	6	0	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite
tamoxifen [no description available]	4.34	19	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
hydroxypropyl-gamma-cyclodextrin [no description available]	6.31	48	0
sodium taurodeoxycholate Taurodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with taurine, usually as the sodium salt. It is used as a cholagogue and choleretic, also industrially as a fat emulsifier.. taurodeoxycholic acid : A bile acid taurine conjugate of deoxycholic acid.. taurodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurodeoxycholic acid.	3.12	5	0	bile acid taurine conjugate	human metabolite
tetraoctylammonium bromide tetraoctylammonium bromide: a phase transfer reagent	2.06	1	0
1-butyl-3-methylimidazolium chloride 1-butyl-3-methylimidazolium chloride: structure in first source	2.46	2	0
1-butyl-3-methylimidazolium tetrafluoroborate [no description available]	2.02	1	0
1-dodecyl-3-methylimidazolium 1-dodecyl-3-methylimidazolium: structure in first source. 1-dodecyl-3-methylimidazolium : A 1-alkyl-3-methylimidazolium in which the alkyl substituent at C-1 is dodecyl.	2.03	1	0	1-alkyl-3-methylimidazolium
1-tetradecyl-3-methylimidazolium [no description available]	2.03	1	0
1-ethyl-3-methylimidazolium bromide 1-ethyl-3-methylimidazolium bromide: structure in first source	2.08	1	0
1-octyl-3-methylimidazolium hexafluorophosphate 1-octyl-3-methylimidazolium hexafluorophosphate: is a nonaqueous ionic liquid	2.31	1	0
nadp [no description available]	2.71	3	0
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	4.47	20	0
ethionamide Ethionamide: A second-line antitubercular agent that inhibits mycolic acid synthesis.. ethionamide : A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding S-oxide.	2.84	3	0	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug
6-carboxytetramethylrhodamine [no description available]	2.17	1	0
wiskostatin wiskostatin: induces folding of N-WASP's GTPase-binding domain into its autoinhibited conformation; structure in first source. wiskostatin : A racemate comprising equimolar amounts of (R)- and (S)-wiskostatin.. 1-(3,6-dibromocarbazol-9-yl)-3-(dimethylamino)propan-2-ol : A member of the class of carbazoles that is 1-(carbazol-9-yl)-3-(dimethylamino)propan-2-ol bearing two additional bromo substituents at positions 3 and 6 on the carbazole ring system.	2.06	1	0	carbazoles; organobromine compound; secondary alcohol; tertiary amino compound
zeranol Zeranol: A non-steroidal estrogen analog.	2.63	2	0	macrolide
fusidic acid Fusidic Acid: An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed). It acts by inhibiting translocation during protein synthesis.. fusidic acid : A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum.	2.94	4	0	11alpha-hydroxy steroid; 3alpha-hydroxy steroid; alpha,beta-unsaturated monocarboxylic acid; steroid acid; steroid antibiotic; sterol ester	EC 2.7.1.33 (pantothenate kinase) inhibitor; Escherichia coli metabolite; protein synthesis inhibitor
valinomycin Valinomycin: A cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins. It is composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form a 36-membered ring. (From Merck Index, 11th ed) Valinomycin is a potassium selective ionophore and is commonly used as a tool in biochemical studies.. valinomycin : A twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.	2.44	2	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
thiopental Thiopental: A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.. thiopental : A barbiturate, the structure of which is that of 2-thiobarbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.4	2	0	barbiturates	anticonvulsant; drug allergen; environmental contaminant; intravenous anaesthetic; sedative; xenobiotic
uc-781 [no description available]	2.74	3	0
estrone sulfate estrone sulfate: sulfoconjugated estrone; RN given refers to parent cpd	2.48	2	0	17-oxo steroid; steroid sulfate	human metabolite; mouse metabolite
ranitidine Ranitidine: A non-imidazole blocker of those histamine receptors that mediate gastric secretion (H2 receptors). It is used to treat gastrointestinal ulcers.. ranitidine : A member of the class of furans used to treat peptic ulcer disease (PUD) and gastroesophageal reflux disease.	2.73	3	0	C-nitro compound; furans; organic sulfide; tertiary amino compound	anti-ulcer drug; drug allergen; environmental contaminant; H2-receptor antagonist; xenobiotic
helvolic acid helvolic acid: structure. helvolic acid : A steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.	2.42	2	0	3-oxo-Delta(1) steroid; acetate ester; monocarboxylic acid; steroid acid	antibacterial agent; fungal metabolite; mycotoxin
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.03	1	0	aryl sulfide; dinitrile; enamine; substituted aniline	antineoplastic agent; antioxidant; apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; osteogenesis regulator; vasoconstrictor agent
ggti 286 GGTI 286: the methyl ester of GGTI-287; inhibits geranylgeranyltransferase	2.03	1	0
laccase Laccase: A copper-containing oxidoreductase enzyme that catalyzes the oxidation of 4-benzenediol to 4-benzosemiquinone. It also has activity towards a variety of O-quinols and P-quinols. It primarily found in FUNGI and is involved in LIGNIN degradation, pigment biosynthesis and detoxification of lignin-derived products.	2.13	1	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.55	2	0	alkali metal atom
dermatan sulfate Dermatan Sulfate: A naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from CHONDROITIN SULFATE A (see CHONDROITIN SULFATES) by containing IDURONIC ACID in place of glucuronic acid, its epimer, at carbon atom 5. (from Merck, 12th ed). alpha-L-IdopA-(1->3)-beta-D-GalpNAc4S : An oligosaccharide sulfate that is 2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranose in which the hydroxy group at position 3 has been converted to the corresponding alpha-L-idopyranuronoside.. dermatan sulfate : Any of a group of glycosaminoglycans with repeating units consisting of variously sulfated beta1->4-linked L-iduronyl-(alpha1->3)-N-acetyl-D-galactosamine units.	2.05	1	0	amino disaccharide; glycosylgalactose derivative; iduronic acids; oligosaccharide sulfate
nizatidine Nizatidine: A histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers.. nizatidine : A member of the class of 1,3-thiazoles having a dimethylaminomethyl substituent at position 2 and an alkylthiomethyl moiety at position 4.	2.25	1	0
monooctanoin monooctanoin: dissolution agent for retained cholesterol bile duct stones; RN in Chemline for octanoic acid, ester with 1,2,3-propanetriol, MF unknown: 11140-04-8; RN for octanoic acid, 2,3-dihydroxypropyl ester (1-monooctanoin): 502-54-5; RN in 9th CI Form Index for (+-)-1-monooctanoin: 19670-49-6. rac-1-monooctanoylglycerol : A rac-1-monoacylglycerol comprising equal amounts of 1-octanoyl-sn-glycerol and 3-octanoyl-sn-glycerol.. 1-monooctanoylglycerol : A 1-monoglyceride that has octanoyl as the acyl group.	2.08	1	0	1-monoglyceride; octanoate ester; rac-1-monoacylglycerol
1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene: structure given in first source	1.98	1	0	stilbenoid
orlistat Orlistat: A lactone derivative of LEUCINE that acts as a pancreatic lipase inhibitor to limit the absorption of dietary fat; it is used in the management of obesity.. orlistat : A carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug.	2.31	1	0	beta-lactone; carboxylic ester; formamides; L-leucine derivative	anti-obesity agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor; EC 3.1.1.3 (triacylglycerol lipase) inhibitor
quinine [no description available]	2.44	2	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
kaurenoic acid kaurenoic acid: isolated from leaves of Montanoa tomentosa; structure given in first source. ent-kaur-16-en-19-oic acid : An ent-kaurane diterpenoid that is ent-kauran-19-oic acid in which a double bond is present at position 16(17); exhibits anticancer and anti-HIV 1 activity.	2.6	1	0
azoxystrobin azoxystrobin: a methoxyacrylate analog; a strobilurin fungicide; structure given in first source. azoxystrobin : An aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 2-methoxy-1-(methoxycarbonyl)vinyl substituent, also at C-2. An inhibitor of mitochondrial respiration by blocking electron transfer between cytochromes b and c1, it is used widely as a fungicide in agriculture.	2.11	1	0	aryloxypyrimidine; enoate ester; enol ether; methoxyacrylate strobilurin antifungal agent; methyl ester; nitrile	antifungal agrochemical; environmental contaminant; mitochondrial cytochrome-bc1 complex inhibitor; quinone outside inhibitor; xenobiotic
mitragynine [no description available]	2.41	1	0	monoterpenoid indole alkaloid
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester [no description available]	2.71	3	0
methyl radical [no description available]	2.07	1	0	organic radical
tauro-24,25-dihydrofusidate tauro-24,25-dihydrofusidate: affects nasal absorption of insulin in sheep	1.99	1	0
glycodeoxycholic acid Glycodeoxycholic Acid: A bile salt formed in the liver by conjugation of deoxycholate with glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic.. glycodeoxycholic acid : A bile acid glycine conjugate of deoxycholic acid.	2.46	2	0	bile acid glycine conjugate	human metabolite
deltorphin deltorphin: isolated from skin of Phyllomedusa sauvagei; has affinity to opioid receptor; note deltorphin I and deltorphin II are available, they have Ala in position 2	2.05	1	0	peptide
rtki cpd RTKI cpd: preferentially inhibits human glioma cells expressing truncated rather than wild-type epidermal growth factor receptors	2.74	3	0
3-hydroxymexiletine 3-hydroxymexiletine: metabolite of mexiletine; structure given in first source	2.07	1	0
8-bromoguanosino-3',5'-cyclic monophosphorothioate [no description available]	2.07	1	0
cystine [no description available]	2.51	2	0
beta-cyclodextrin tetradecasulfate beta-cyclodextrin tetradecasulfate: RN given refers to cpd without isomeric designation	4.33	20	0
fospropofol [no description available]	2.07	1	0	alkylbenzene
rasagiline [no description available]	2.21	1	0	indanes; secondary amine; terminal acetylenic compound	EC 1.4.3.4 (monoamine oxidase) inhibitor; neuroprotective agent
dasatinib N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxamide: a dasatinib prodrug; structure in first source. dasatinib (anhydrous) : An aminopyrimidine that is 2-methylpyrimidine which is substituted at position 4 by the primary amino group of 2-amino-1,3-thiazole-5-carboxylic acid and at position 6 by a 4-(2-hydroxyethyl)piperazin-1-yl group, and in which the carboxylic acid group has been formally condensed with 2-chloro-6-methylaniline to afford the corresponding amide. A multi-targeted kinase inhibitor, it is used, particularly as the monohydrate, for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhydrous dasatinib (INN).	2.11	1	0	1,3-thiazoles; aminopyrimidine; monocarboxylic acid amide; N-(2-hydroxyethyl)piperazine; N-arylpiperazine; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antineoplastic agent; tyrosine kinase inhibitor
3-deoxyhexulose 3-deoxyhexulose: interacts with the enzymes of fructose metabolism; structure given in first source; RN given refers to (D)-isomer; RN for cpd without isomeric designation not avail 5/91. 3-deoxy-keto-D-fructose : A deoxyketohexose that is keto-D-fructose that is lacking the hydroxy group at position 3. A metabolite of 3-deoxyglucosone, a dicarbonyl sugar synthesised through the Maillard reaction.	1.98	1	0	alpha-hydroxy ketone; beta-hydroxy ketone; deoxyketohexose; hexanone
5-nitroso-salicylate 5-nitroso-salicylate: metabolite of 5-aminosalicylic acid	2.02	1	0	hydroxybenzoic acid
ethylphenidate ethylphenidate: structure given in first source	2.1	1	0
piperolactam a piperolactam A: isolated from Houttynia cordata; structure in first source	2.13	1	0	alkaloid
telavancin telavancin: an anti-infective agent; structure in first source. telavancin : A glycopeptide that is vancomycin substituted at position N-3'' by a 2-(decylamino)ethyl group and at position C-29 by a (phosphonomethyl)aminomethyl group. Used as its hydrochloride salt for treatment of adults with complicated skin and skin structure infections caused by bacteria.	2.05	1	0	glycopeptide	antibacterial drug; antimicrobial agent
ferrocenium ferrocenium: structure given in first source	2	1	0
nitinol nitinol: RN given refers to cpd with MF of Ni-Ti; do not confuse with titanium nickelide; other nitinols (nitinol SE and nitinol 55) are Co-Ni-Ti alloys	2.25	1	0
calixarenes Calixarenes: Phenolic metacyclophanes derived from condensation of PHENOLS and ALDEHYDES. The name derives from the vase-like molecular structures. A bracketed [n] indicates the number of aromatic rings.. calixarenes : Originally macrocyclic compounds capable of assuming a basket (or "calix") shaped conformation. They are formed from p-hydrocarbyl phenols and formaldehyde. The term now applies to a variety of derivatives by substitution of the hydrocarbon cyclo{oligo[(1,3-phenylene)methylene]}.. calixarene : A macrocycle composed of 1,3-phenylene groups linked by methylene groups. The number of 1,3-phenylene units in the macrocycle is denoted by the "n" in calix[n]arene name.	6.21	17	0
gma-edma GMA-EDMA: copolymer of glycidyl methacrylate & ethylene dimethacrylate; used for enzyme immobilization	2.76	3	0
sulfaton sulfaton: Russian drug; structure given in first source	2.02	1	0
18-crown-6 2,3,11,12-tetracarboxylic acid 18-crown-6 2,3,11,12-tetracarboxylic acid: structure in first source; RN given for (2R,3R,11,12)-isomer	2.46	2	0
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	3.18	5	0
metaphosphoric acid metaphosphoric acid: RN given refers to cpd with structure HPO3. phosphonate(1-) : A monovalent inorganic anion obtained by deprotonation of one of the two OH groups in phosphonic acid.	1.99	1	0
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	3.33	6	0
conferone conferone: structure in first source; from Ferula schtschurowskiana	2.31	1	0	coumarins
poly(sodium vinyl sulfonate) lyapolate: sulfonic acid polymers represent a new class of HIV inhibitors	2.01	1	0
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.95	4	0
sodium dodecyl sulfate Sodium Dodecyl Sulfate: An anionic surfactant, usually a mixture of sodium alkyl sulfates, mainly the lauryl; lowers surface tension of aqueous solutions; used as fat emulsifier, wetting agent, detergent in cosmetics, pharmaceuticals and toothpastes; also as research tool in protein biochemistry.. sodium dodecyl sulfate : An organic sodium salt that is the sodium salt of dodecyl hydrogen sulfate.	5.46	60	0	organic sodium salt	detergent; protein denaturant
mtt formazan MTT formazan: a blue MEM-insoluble mitochondrial byproduct; used to determine viability of cells with active mitochondrial dehydrogenase enzymes	2.45	2	0
zinc protoporphyrin ix [no description available]	2.49	2	0
alpha-chymotrypsin Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.	3.7	10	0
alpinetin alpinetin: from Alpinia henryi K. Schum.; structure in first source	2.08	1	0	ether; flavonoids
sew2871 SEW2871: structure in first source	2.04	1	0	oxadiazole; ring assembly
tetramethylrhodamine isothiocyanate tetramethylrhodamine isothiocyanate: used for labeling of antibodies with fluorochromes; easily dissolved with DMSO; conjugates with immunoglobulins	2.02	1	0
clopidogrel carboxylic acid clopidogrel carboxylic acid: InChIKey: DCASRSISIKYPDD-UHFFFAOYSA-N. clopidogrel carboxylic acid : A thienopyridine that is 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-ylacetic acid substituted by a 2-chlorophenyl group at position 2. It is a metabolite of the drug clopidogrel.	3.46	1	1	monocarboxylic acid; monochlorobenzenes; tertiary amino compound; thienopyridine	drug metabolite; marine xenobiotic metabolite
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	4.07	14	0
d 609 [no description available]	2.05	1	0
am 630 iodopravadoline: an aminoalkylindole; a competitive cannabinoid receptor antagonist; structure given in first source	2.06	1	0	N-acylindole
sodium borohydride sodium borohydride: RN given refers to parent cpd	2.1	1	0	inorganic sodium salt; metal tetrahydridoborate
hydroxyethylcellulose hydroxyethylcellulose: component of contact lens wetting solutions; aldiamed is an artificial saliva; RN given refers to parent cpd. hydroxyethylcellulose : A polysaccharide derivative that is cellulose in which hydroxyethyl groups are bound to some of the hydroxyl groups of the glucopyranose monomers.	3.22	5	0
ethyl 4-chloro-3-hydroxybutanoate ethyl 4-chloro-3-hydroxybutanoate: an optically active compound	2.81	3	0
myelin basic protein Myelin Basic Protein: An abundant cytosolic protein that plays a critical role in the structure of multilamellar myelin. Myelin basic protein binds to the cytosolic sides of myelin cell membranes and causes a tight adhesion between opposing cell membranes.	2.04	1	0
palladium oxide palladium oxide: RN given refers to PdO	2.6	1	0
cinnamamide cinnamamide: structure in first source. cinnamamide : The simplest member of the class of cinnamamides that consists of acrylamide bearing a phenyl substituent at the 3-position.. trans-cinnamamide : The E (trans) isomer of cinnamamide.	2.03	1	0	cinnamamide
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	3.44	7	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	5.12	40	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	3.32	6	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	5.36	13	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.05	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
formononetin [no description available]	2.31	1	0	4'-methoxyisoflavones; 7-hydroxyisoflavones	phytoestrogen; plant metabolite
vitexin [no description available]	2.6	1	0	C-glycosyl compound; trihydroxyflavone	antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite; platelet aggregation inhibitor
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	3.98	12	0	trihydroxyflavone	antineoplastic agent; metabolite
luteolin [no description available]	2.54	2	0	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.3	6	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
calcitriol dihydroxy-vitamin D3: as a major in vitro metabolite of 1alpha,25-dihydroxyvitamin D3, produced in primary cultures of neonatal human keratinocytes	3.55	8	0	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	1.96	1	0
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	3.56	8	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
11-cis-retinal Rhodopsin: A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm.. 11-cis-retinal : A retinal having 2E,4Z,6E,8E-double bond geometry.	2.95	4	0	retinal	chromophore; human metabolite; mouse metabolite
thromboxane a2 Thromboxane A2: An unstable intermediate between the prostaglandin endoperoxides and thromboxane B2. The compound has a bicyclic oxaneoxetane structure. It is a potent inducer of platelet aggregation and causes vasoconstriction. It is the principal component of rabbit aorta contracting substance (RCS).. thromboxane A2 : A thromboxane which is produced by activated platelets and has prothrombotic properties: it stimulates activation of new platelets as well as increases platelet aggregation.	2.04	1	0	epoxy monocarboxylic acid; thromboxanes A	mouse metabolite
retinol palmitate retinol palmitate: RN given refers to parent cpd; structure. retinyl palmitate : A palmitate ester of retinol with undefined geometry about the C=C bonds.. all-trans-retinyl palmitate : An all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis.	2.61	2	0	all-trans-retinyl ester; retinyl palmitate	antioxidant; Escherichia coli metabolite; human xenobiotic metabolite
hymecromone Hymecromone: A coumarin derivative possessing properties as a spasmolytic, choleretic and light-protective agent. It is also used in ANALYTICAL CHEMISTRY TECHNIQUES for the determination of NITRIC ACID.	2.49	2	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
rosin rosin: Resin from plant. Do not confuse with the specific compound: 3-phenyl-2-propenyl-(E)-beta-D-glucopyranoside, also know as rosin.	2.25	1	0
alprostadil [no description available]	3.91	12	0	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
vitamin d 2 Ergocalciferols: Derivatives of ERGOSTEROL formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. They differ from CHOLECALCIFEROL in having a double bond between C22 and C23 and a methyl group at C24.. vitamin D2 : A vitamin D supplement and has been isolated from alfalfa.	2.38	2	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
stigmasterol stigmasta-5,22-dien-3-ol: isolated from freeze-dried powder of Blackberries (Rubus ursinus L.) which showed an activity on inhibition of chemocarcinogen. stigmasterol : A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.	2.72	3	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols; stigmastane sterol	plant metabolite
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	2.94	4	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	4.4	20	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
kaempferol [no description available]	2.8	3	0	7-hydroxyflavonol; flavonols; tetrahydroxyflavone	antibacterial agent; geroprotector; human blood serum metabolite; human urinary metabolite; human xenobiotic metabolite; plant metabolite
6-ketoprostaglandin f1 alpha 6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue.. 6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position.	1.98	1	0	prostaglandins Falpha	human metabolite; mouse metabolite
gamma-linolenic acid gamma-Linolenic Acid: An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed). gamma-linolenic acid : A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.	2.03	1	0	linolenic acid; omega-6 fatty acid	human metabolite; mouse metabolite; plant metabolite
harmine Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.	3.02	4	0	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
genistein [no description available]	4.14	15	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	4.78	9	0	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
pulmicort Budesonide: A glucocorticoid used in the management of ASTHMA, the treatment of various skin disorders, and allergic RHINITIS.. budesonide : A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.	3.32	6	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen
eprosartan eprosartan: angiotensin II receptor antagonist. eprosartan : A member of the class of imidazoles and thiophenes that is an angiotensin II receptor antagonist used for the treatment of high blood pressure.	2.41	1	0	dicarboxylic acid; imidazoles; thiophenes	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
montelukast montelukast: a leukotriene D4 receptor antagonist	2.13	1	0	aliphatic sulfide; monocarboxylic acid; quinolines	anti-arrhythmia drug; anti-asthmatic drug; leukotriene antagonist
kava Kava: Dried rhizome and roots of Piper methysticum, a shrub native to Oceania and known for its anti-anxiety and sedative properties. Heavy usage results in some adverse effects. It contains ALKALOIDS; LACTONES; kawain, methysticin, mucilage, STARCH, and yangonin. Kava is also the name of the pungent beverage prepared from the plant's roots.	2.05	1	0
previtamin d(3) previtamin D3 : A hydroxy seco-steroid which is an intermediate in the production of vitamin D3 in human skin.	1.98	1	0	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol	human metabolite
11-octadecenoic acid 11-octadecenoic acid: vaccenic acid is the (E)-isomer. trans-vaccenic acid : The trans- isomer of vaccenic acid.	2.21	1	0	vaccenic acid
2-hexenal, z-isomer 2-hexenal: product of lipid peroxidation in the rat liver; a green odor chemical; do not confuse with the hexabarbital synonym, hexenal; RN given refers to cpd without isomeric designation. 2-hexenal : A hexenal having the double bond at the 2-position.. (2E)-hexenal : A 2-hexenal in which the olefinic double bond has E configuration. It occurs naturally in a wide range of fruits, vegetables, and spices.	2.07	1	0	2-hexenal	antibacterial agent; flavouring agent; plant metabolite
astaxanthine astaxanthine: a keto form of carotene; pigment in flesh of Scottish salmon (Salmo salar) crustacoa-lobster (Homarus gammarus, flamingo feathers; structure; a carotenoid without vitamin A activity, has shown anti-oxidant and anti-inflammatory activities. astaxanthin : A carotenone that consists of beta,beta-carotene-4,4'-dione bearing two hydroxy substituents at positions 3 and 3' (the 3S,3'S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein.	2.74	3	0	carotenol; carotenone	animal metabolite; anticoagulant; antioxidant; food colouring; plant metabolite
canthaxanthin Canthaxanthin: A trans-carotenoid pigment widely distributed in nature. The compound is used as an oral suntanning agent and as a food and drug coloring agent. Oral ingestion of the compound causes canthaxanthin retinopathy.. canthaxanthin : A carotenone that consists of beta,beta-carotene bearing two oxo substituents at positions 4 and 4'.	2.44	2	0	carotenone	biological pigment; Escherichia coli metabolite; food colouring; fungal metabolite
lutein Lutein: A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.. xanthophyll : A subclass of carotenoids consisting of the oxygenated carotenes.	2.74	3	0	carotenol	food colouring; plant metabolite
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	2.78	3	0	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2.13	1	0	hydroxycoumarin	fluorescent probe; food component; plant metabolite
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	2.03	1	0	alpha-humulene
oleuropein oleuropein: iridoid isolated from leaves and fruit of Olea and Ligustrum (Oleaceae). oleuropein : A secoiridoid glycoside that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the anomeric hydroxy group at position 2 has been converted into its beta-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.	2.81	3	0	beta-D-glucoside; catechols; diester; methyl ester; pyrans; secoiridoid glycoside	anti-inflammatory agent; antihypertensive agent; antineoplastic agent; antioxidant; apoptosis inducer; NF-kappaB inhibitor; nutraceutical; plant metabolite; radical scavenger
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	2.88	3	0	macrolide; resorcinols	fungal metabolite; mycoestrogen
baicalein [no description available]	3.49	7	0	trihydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 4.1.1.17 (ornithine decarboxylase) inhibitor; ferroptosis inhibitor; geroprotector; hormone antagonist; plant metabolite; prostaglandin antagonist; radical scavenger
chrysin chrysin : A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.	2.25	1	0	7-hydroxyflavonol; dihydroxyflavone	anti-inflammatory agent; antineoplastic agent; antioxidant; EC 2.7.11.18 (myosin-light-chain kinase) inhibitor; hepatoprotective agent; plant metabolite
fisetin [no description available]	3.04	4	0	3'-hydroxyflavonoid; 7-hydroxyflavonol; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; metabolite; plant metabolite
galangin 5,7-dihydroxyflavonol: antimicrobial from the twigs of Populus nigra x Populus deltoides; structure in first source. galangin : A 7-hydroxyflavonol with additional hydroxy groups at positions 3 and 5 respectively; a growth inhibitor of breast tumor cells.	2.41	1	0	7-hydroxyflavonol; trihydroxyflavone	antimicrobial agent; EC 3.1.1.3 (triacylglycerol lipase) inhibitor; plant metabolite
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.03	1	0	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	2.76	3	0	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
mangostin mangostin: xanthone from rind of Garcinia mangostana Linn. fruit. alpha-mangostin : A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities.	2.61	2	0	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite
3-methylquercetin isorhamnetin : A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group.	2.21	1	0	7-hydroxyflavonol; monomethoxyflavone; tetrahydroxyflavone	anticoagulant; EC 1.14.18.1 (tyrosinase) inhibitor; metabolite
morin morin: a light yellowish pigment found in the wood of old fustic (Chlorophora tinctoria). morin : A pentahydroxyflavone that is 7-hydroxyflavonol bearing three additional hydroxy substituents at positions 2' 4' and 5.	2.78	3	0	7-hydroxyflavonol; pentahydroxyflavone	angiogenesis modulating agent; anti-inflammatory agent; antibacterial agent; antihypertensive agent; antineoplastic agent; antioxidant; EC 5.99.1.2 (DNA topoisomerase) inhibitor; hepatoprotective agent; metabolite; neuroprotective agent
myricetin [no description available]	2.99	4	0	7-hydroxyflavonol; hexahydroxyflavone	antineoplastic agent; antioxidant; cyclooxygenase 1 inhibitor; food component; geroprotector; hypoglycemic agent; plant metabolite
robinetin robinetin: structure given in first source. robinetin : A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 7, 3, 4' and 5'.	2.03	1	0	7-hydroxyflavonol; pentahydroxyflavone	plant metabolite
scutellarein scutellarein: aglycone of scutellarin from Scutellaria baicalensis; carthamidin is 2S isomer of scutellarein; do not confuse with isoscutellarein and/or isocarthamidin which are respective regioisomers, or with the scutelarin protein. scutellarein : Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.	2.5	2	0	tetrahydroxyflavone	metabolite
wogonin wogonin: structure in first source. wogonin : A dihydroxy- and monomethoxy-flavone in which the hydroxy groups are positioned at C-5 and C-7 and the methoxy group is at C-8.	2.07	1	0	dihydroxyflavone; monomethoxyflavone	angiogenesis inhibitor; antineoplastic agent; cyclooxygenase 2 inhibitor; plant metabolite
coumestrol Coumestrol: A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.. coumestrol : A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.	2.75	3	0	coumestans; delta-lactone; polyphenol	anti-inflammatory agent; antioxidant; plant metabolite
daidzein [no description available]	3.59	8	0	7-hydroxyisoflavones	antineoplastic agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; phytoestrogen; plant metabolite
trans-2,3',4,5'-tetrahydroxystilbene trans-2,3',4,5'-tetrahydroxystilbene: hydroxystilbene oxyresveratrol	2.81	3	0	stilbenoid
pterostilbene [no description available]	2.78	3	0	diether; methoxybenzenes; stilbenol	anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; hypoglycemic agent; neuroprotective agent; neurotransmitter; plant metabolite; radical scavenger
epsilon-viniferin epsilon-viniferin: stilbene dimer; isolated from the Oriental medicinal plant Vitis coignetiae; structure given in first source. (-)-trans-epsilon-viniferin : A stilbenoid that is the (-)-trans-stereoisomer of epsilon-viniferin, obtained by cyclodimerisation of trans-resveratrol.	2.13	1	0	1-benzofurans; polyphenol; stilbenoid	metabolite
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.03	1	0	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
rosmarinic acid rosmarinic acid: RN given refers to parent cpd; promote OT project. (R)-rosmarinic acid : A stereoisomer of rosmarinic acid having (R)-configuration.. rosmarinic acid : The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid.	2.13	1	0	rosmarinic acid	geroprotector; plant metabolite
rottlerin rottlerin: an angiogenesis inhibitor; an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III; RN refers to (E)-isomer; do not confuse this chalcone with an anthraquinone that is also called rottlerin (RN 481-72-1);. rottlerin : A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.	2.45	2	0	aromatic ketone; benzenetriol; chromenol; enone; methyl ketone	anti-allergic agent; antihypertensive agent; antineoplastic agent; apoptosis inducer; K-ATP channel agonist; metabolite
ellagic acid [no description available]	2.15	1	0	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
cyhalothrin cyhalothrin: acaricidal & insecticidal synthetic pyrethroid; structure given in first source. cyhalothrin : A carboxylic ester obtained by formal condensation between 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol.	2.41	1	0	aromatic ether; cyclopropanecarboxylate ester; nitrile; organochlorine compound; organofluorine compound	agrochemical; pyrethroid ester acaricide; pyrethroid ester insecticide
prostaglandin a1 [no description available]	1.99	1	0	prostaglandins A
coenzyme q10 coenzyme Q10: Ubiquinone ring with a chain of 10 isoprene units; redox equilibrium with ubiqunol serving in mitochondrial inner membrane to transfer electrons; presence during reconstitution of acetylcholine receptor into phospholipid vesicles yields vesicles active in catalyzing carbamylcholine-sensitive Na+ flux; coenzyme Q10 depletion has been noted with use of statins. coenzyme Q10 : A ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration.	4.34	4	1	ubiquinones	antioxidant; ferroptosis inhibitor; human metabolite
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	3.82	11	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
cilnidipine [no description available]	2.07	1	0	2-methoxyethyl ester; C-nitro compound; dihydropyridine	antihypertensive agent; calcium channel blocker; cardiovascular drug
tranilast tranilast: antiallergic drug; potent inhibitor of homologous passive cutaneous anaphylaxis. tranilast : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.	2.46	2	0	amidobenzoic acid; cinnamamides; dimethoxybenzene; secondary carboxamide	anti-allergic agent; anti-asthmatic drug; antineoplastic agent; aryl hydrocarbon receptor agonist; calcium channel blocker; hepatoprotective agent; nephroprotective agent
glyceryl 2-arachidonate glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source. 2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.	2.76	3	0	2-acylglycerol 20:4; endocannabinoid	human metabolite
1-palmitoyl-2-oleoyl-sn-glycerol 1-palmitoyl-2-oleoyl-sn-glycerol: a long-chain diacylglycerol; RN given refers to compound with no isomeric designation of the glycerol C2. 1-palmitoyl-2-oleoyl-sn-glycerol : A 1,2-diacyl-sn-glycerol with palmitoyl as the 1-acyl group and oleoyl as the 2-acyl group.	2.07	1	0	1,2-diacyl-sn-glycerol; 1-palmitoyl-2-oleoylglycerol	mouse metabolite
isotretinoin Isotretinoin: A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.. isotretinoin : A retinoic acid that is all-trans-retinoic acid in which the double bond which is alpha,beta- to the carboxy group is isomerised to Z configuration. A synthetic retinoid, it is used for the treatment of severe cases of acne and other skin diseases.	2.43	2	0	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent
fondaparinux Fondaparinux: Synthetic pentasaccharide that mediates the interaction of HEPARIN with ANTITHROMBINS and inhibits FACTOR Xa; it is used for prevention of VENOUS THROMBOEMBOLISM after surgery.. fondaparinux : A synthetic pentasaccharide which, apart from the O-methyl group at the reducing end of the molecule, consists of monomeric sugar units which are identical to a sequence of five monomeric sugar units that can be isolated after either chemical or enzymatic cleavage of the polymeric glycosaminoglycans heparin and heparan sulfate.	2.31	1	0	amino sugar; oligosaccharide sulfate; pentasaccharide derivative	anticoagulant
9,11-linoleic acid 9,11-linoleic acid: a conjugated dienoic linoleate (CLA); RN given refers to cpd without isomeric designation in Chemline. (9E,11E)-octadecadienoic acid : An octadeca-9,11-dienoic acid having 9-trans,11-trans-stereochemistry.	2.15	1	0	octadeca-9,11-dienoic acid	anti-inflammatory agent; antiatherogenic agent; antineoplastic agent; apoptosis inducer; bacterial xenobiotic metabolite; human metabolite
9-hydroxy-10,12-octadecadienoic acid 9-hydroxy-10,12-octadecadienoic acid: RN given refers to unspecified stereoisomer. 9-HODE : A HODE that consists of (10E,12Z)-octadecadienoic acid with the hydroxy substituent located at position 9.	2.01	1	0	HODE; octadecadienoic acid	human metabolite; metabolite; mouse metabolite; plant metabolite
2,4-heptadienal 2,4-heptadienal: structure in first source. (E,E)-hepta-2,4-dienal : A heptadienal in which the two double bonds are located at positions 2 and 4 (the E,E-geoisomer).	2.11	1	0	heptadienal	flavouring agent
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	3.06	4	0	4-hydroxynon-2-enal; 4-hydroxynonenal
1-monooleoyl-rac-glycerol Peceol: lipid excipient containing readily dispersible mixture of mono- & diglycerides of oleic acid. 1-oleoylglycerol : A 1-monoglyceride where the acyl group is oleoyl.. monooleoylglycerol : A monoglyceride in which the acyl group is oleoyl with the position of acylation unspecified.	2.5	2	0	1-acylglycerol 18:1; monooleoylglycerol	plant metabolite
sphingosine 1-phosphate sphingosine 1-phosphate: RN given refers to (R-(R,S-(E)))-isomer; RN for cpd without isomeric designation not available 8/89. sphingosine 1-phosphate : A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1	2.04	1	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
n-palmitoylsphingosine N-palmitoylsphingosine: structure given in first source; RN given refers to (R,S-(E))-isomer. N-hexadecanoylsphingosine : A N-acylsphingosine in which the ceramide N-acyl group is specified as hexadecanoyl (palmitoyl).	2.77	3	0	Cer(d34:1); N-acylsphingosine; N-palmitoyl-sphingoid base	human blood serum metabolite; Mycoplasma genitalium metabolite
ceramide 1-phosphate ceramide 1-phosphate : A phosphosphingolipid consisting of any ceramide phosphorylated at position 1. N-octadecanoylsphingosine 1-phosphate : A ceramide 1-phosphate that is the N-octadecananoyl (stearoyl) derivative of sphingosine.	2.02	1	0	N-acylsphingosine 1-phosphate
cholesteryl oleate cholesteryl oleate: RN given refers to ((Z)-isomer). cholesteryl oleate : The (Z)-stereoisomer of cholesteryl octadec-9-enoate.	2.06	1	0	CE(18:1); cholesteryl octadec-9-enoate	mouse metabolite
fucosterol [no description available]	1.98	1	0	steroid
codeine [no description available]	2.03	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
methyl linoleate [no description available]	2.02	1	0	fatty acid methyl ester	plant metabolite
4-dimethylaminocinnamaldehyde [no description available]	2.01	1	0	cinnamaldehydes
acitretin Acitretin: An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of ETRETINATE with the advantage of a much shorter half-life when compared with etretinate.. acitretin : A retinoid that consists of 3,7-dimethylnona-2,4,6,8-tetraenoic acid having a 4-methoxy-2,3,6-trimethylphenyl group attached at position 9.	2.02	1	0	acitretin; alpha,beta-unsaturated monocarboxylic acid; retinoid	keratolytic drug
dorzolamide dorzolamide: topically effective ocular hypotensive carbonic anhydrase inhibitor; RN refers to mono-HCl (4S-trans)-isomer. dorzolamide : 5,6-Dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide in which hydrogens at the 4 and 6 positions are substituted by ethylamino and methyl groups, respectively (4S, trans-configuration). A carbonic anhydrase inhibitor, it is used as the hydrochloride in ophthalmic solutions to lower increased intraocular pressure in the treatment of open-angle glaucoma and ocular hypertension.	2.13	1	0	sulfonamide; thiophenes	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor
granisetron Granisetron: A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.. granisetron : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT3 receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting.	2.74	3	0	aromatic amide; indazoles
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	2.95	4	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
sirolimus Sirolimus: A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.. sirolimus : A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.	3.48	7	0	antibiotic antifungal drug; cyclic acetal; cyclic ketone; ether; macrolide lactam; organic heterotricyclic compound; secondary alcohol	antibacterial drug; anticoronaviral agent; antineoplastic agent; bacterial metabolite; geroprotector; immunosuppressive agent; mTOR inhibitor
gamma-cyclodextrin gamma-cyclodextrin : A cycloamylose composed of eight alpha-(1->4) linked D-glucopyranose units.	7.08	104	0	cyclodextrin
brefeldin a [no description available]	3.9	12	0	macrolide antibiotic	Penicillium metabolite
lobeline Lobeline: An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.	2.4	2	0
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	3.98	13	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
2-methylthio-atp 2-methylthio-ATP: purinergic receptors agonist; relaxes mammalian gut preparations; structure given in first source	2.08	1	0
atosiban [no description available]	2.07	1	0	oligopeptide
cicaprost cicaprost: RN given refers to (3aS-(2E,3aalpha,4alpha(3R,4R),5beta,6aalpha))-isomer	1.97	1	0	monoterpenoid
clobetasol Clobetasol: A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.. clobetasol : A 3-oxo-Delta(1),Delta(4)-steroid that is 16beta-methylpregna-1,4-diene-3,20-dione bearing hydroxy groups at the 11beta and 17alpha positions, fluorine at position 9, and a chlorine substituent at position 21. It is used as its 17alpha-propionate ester to treat various skin disorders, including exzema and psoriasis.	2.21	1	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; fluorinated steroid; glucocorticoid; tertiary alpha-hydroxy ketone	anti-inflammatory drug; SMO receptor agonist
cloprostenol Cloprostenol: A synthetic prostaglandin F2alpha analog. The compound has luteolytic effects and is used for the synchronization of estrus in cattle.	2.04	1	0	prostanoid
denopamine denopamine: structure given in first source	2	1	0	dimethoxybenzene
dexmedetomidine [no description available]	2.31	1	0	medetomidine	alpha-adrenergic agonist; analgesic; non-narcotic analgesic; sedative
fluticasone Fluticasone: A STEROID with GLUCOCORTICOID RECEPTOR activity that is used to manage the symptoms of ASTHMA; ALLERGIC RHINITIS, and ATOPIC DERMATITIS.. fluticasone : A trifluorinated corticosteroid used in the form of its propionate ester for treatment of allergic rhinitis.	2.52	2	0	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; corticosteroid; fluorinated steroid; thioester	anti-allergic agent; anti-asthmatic drug
kallidin Kallidin: A decapeptide bradykinin homolog cleaved from kininogen by kallikreins. It is a smooth-muscle stimulant and hypotensive agent that acts by vasodilatation.	2.71	3	0	peptide
halobetasol halobetasol: used in ointment to treat psoriasis; Ulobetasol cream contains 0.05% 6-fluoroclobetasol 17-propionate	2.21	1	0	corticosteroid hormone
lysophosphatidic acid lysophosphatidic acid: RN given refers to parent cpd. 1-oleoyl-sn-glycerol 3-phosphate : A 1-acyl-sn-glycerol 3-phosphate having oleoyl as the 1-O-acyl group.. lysophosphatidic acid : A member of the class of lysophosphatidic acids obtained by hydrolytic removal of one of the two acyl groups of any phosphatidic acid. A 'closed' class.	2.25	1	0	1-acyl-sn-glycerol 3-phosphate
lysophosphatidylcholines lysophosphatidylcholine : An acylglycerophosphocholine resulting from partial hydrolysis of a phosphatidylcholine, which removes one of the fatty acyl groups. The structure is depicted in the image where R1 = acyl, R2 = H or where R1 = H, R2 = acyl.	3.29	6	0	1-O-acyl-sn-glycero-3-phosphocholine
magnesium trisilicate magnesium trisilicate: RN given refers to parent cpd	2.13	1	0
mdl 100907 Serotonin 5-HT2 Receptor Antagonists: Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes.	2.74	3	0
cytochalasin b Cytochalasin B: A cytotoxic member of the CYTOCHALASINS.. cytochalasin B : An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.	3.44	7	0	cytochalasin; lactam; lactone; organic heterotricyclic compound	actin polymerisation inhibitor; metabolite; mycotoxin; platelet aggregation inhibitor
nateglinide Nateglinide: A phenylalanine and cyclohexane derivative that acts as a hypoglycemic agent by stimulating the release of insulin from the pancreas. It is used in the treatment of TYPE 2 DIABETES.. nateglinide : An N-acyl-D-phenylalanine resulting from the formal condensation of the amino group of D-phenylalanine with the carboxy group of trans-4-isopropylcyclohexanecarboxylic acid. An orally-administered, rapidly-absorbed, short-acting insulinotropic agent, it is used for the treatment of type 2 diabetes mellitus.	2.44	2	0	phenylalanine derivative
calyculin a calyculin A: RN given refers to (5S-(5alpha(2R(1S,3S,4S,5R,6R,7E,9E,11E,13Z),3R),7beta(E(S)),*beta,9alpha))-isomer	2.42	2	0
1,2-oleoylphosphatidylcholine 1,2-oleoylphosphatidylcholine: RN given refers to (Z,Z)-isomer. dioleoyl phosphatidylcholine : A phosphatidylcholine in which the phosphatidyl acyl groups are both oleoyl.	3.35	6	0	phosphatidylcholine(1+)
bisdemethoxycurcumin curcumin III: structure in first source. bisdemethoxycurcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.	2.21	1	0	beta-diketone; diarylheptanoid; enone; polyphenol	EC 3.2.1.1 (alpha-amylase) inhibitor; metabolite
irisquinone irisquinone: from seeds of Iris pallasii Iridaceae; RN given refers to (Z)-isomer	2.02	1	0
andrographolide [no description available]	2.49	2	0	carbobicyclic compound; gamma-lactone; labdane diterpenoid; primary alcohol; secondary alcohol	anti-HIV agent; anti-inflammatory drug; antineoplastic agent; metabolite
icariin [no description available]	2.52	2	0	flavonols; glycosyloxyflavone	antioxidant; bone density conservation agent; EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; phytoestrogen
ligustilide ligustilide: found in Umbelliferae plants; RN given refers to cpd without isomeric designation; structure in first source	2.47	2	0	butenolide	metabolite
nerolidol nerolidol: sesquiterpene; RN given refers to cpd without isomeric designation; nerol is also available. nerolidol : A farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent.. (6Z)-nerolidol : A nerolidol in which the double bond at position 6 adopts a cis-configuration.	2.31	1	0	nerolidol
beta-ocimene beta-ocimene : The trans-stereoisomer of ocimene.. (Z)-beta-ocimene : A beta-ocimene that consists of octa-1,3,6-triene bearing two methyl substituents at positions 3 and 7 (the 3Z-isomer).	2.13	1	0	beta-ocimene	plant metabolite
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.51	2	0
acetaldehyde oxime acetaldehyde oxime: structure. (E)-acetaldehyde oxime : The (E)-stereoisomer of acetaldehyde oxime.. acetaldehyde oxime : An aldoxime derived from acetaldehyde.	2.07	1	0	acetaldehyde oxime
fluvoxamine Fluvoxamine: A selective serotonin reuptake inhibitor that is used in the treatment of DEPRESSION and a variety of ANXIETY DISORDERS.. fluvoxamine : An oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder.	2.04	1	0	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor
7,8-dimethylalloxazine 7,8-dimethylalloxazine: structure. 7,8-dimethylisoalloxazine : A 7,8-dimethylbenzo[g]pteridine-2,4-dione that is isoalloxazine substituted by methyl groups at positions 7 and 8.. lumichrome : A compound showing blue fluorescence, formed by a photolysis of riboflavin in acid or neutral solution.	2.46	2	0	7,8-dimethylbenzo[g]pteridine-2,4-dione	plant metabolite
ag-490 [no description available]	2.15	1	0	catechols; enamide; monocarboxylic acid amide; nitrile; secondary carboxamide	anti-inflammatory agent; antioxidant; apoptosis inducer; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector; STAT3 inhibitor
su 11248 [no description available]	2.21	1	0	monocarboxylic acid amide; pyrroles	angiogenesis inhibitor; antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; immunomodulator; neuroprotective agent; vascular endothelial growth factor receptor antagonist
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2.1	1	0
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	4.32	17	0	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	2.05	1	0	carbon group element atom; elemental tin; metal atom	micronutrient
sulindac sulfide sulindac sulfide: sulfated analog of indomethacin & inhibitor of prostaglandin synthesis in vitro; RN given refers to cpd without isomeric designation; structure given in first source. sulindac sulfide : An aryl sulfide that is a metabolite of sulindac. A non-steroidal anti-inflammatory drug, which also has anticancer activity.	2.03	1	0	aryl sulfide; monocarboxylic acid; organofluorine compound	antineoplastic agent; apoptosis inducer; non-steroidal anti-inflammatory drug
bay 11-7082 (E)-3-tosylacrylonitrile : A nitrile that is acrylonitrile in which the hydrogen located beta,trans to the cyano group is replaced by a tosyl group. It is an inhibitor of cytokine-induced IkappaB-alpha phosphorylation in cells.	2.07	1	0	nitrile; sulfone	apoptosis inducer; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; non-steroidal anti-inflammatory drug; platelet aggregation inhibitor
diamide Diamide: A sulfhydryl reagent which oxidizes sulfhydryl groups to the disulfide form. It is a radiation-sensitizing agent of anoxic bacterial and mammalian cells.	2.03	1	0	1,1'-azobis(N,N-dimethylformamide)
15-hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic acid 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid: A stable prostaglandin endoperoxide analog which serves as a thromboxane mimetic. Its actions include mimicking the hydro-osmotic effect of VASOPRESSIN and activation of TYPE C PHOSPHOLIPASES. (From J Pharmacol Exp Ther 1983;224(1): 108-117; Biochem J 1984;222(1):103-110)	2.21	1	0
antimony Antimony: A metallic element that has the atomic symbol Sb, atomic number 51, and atomic weight 121.75. It is used as a metal alloy and as medicinal and poisonous salts. It is toxic and an irritant to the skin and the mucous membranes.	2.45	2	0	metalloid atom; pnictogen
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	2.4	2	0	alkaline earth metal atom; elemental barium
oleylamine oleylamine: promotes fusion of mouse A(9) fibroblasts; RN given refers to parent cpd with unspecified isomeric designation; structure	2.25	1	0
muconic acid muconic acid: a metabolite of benzene; reported to be a reliable indicator of occupational exposure to benzene; structure given in first source. trans,trans-muconic acid : The trans,trans-isomer of muconic acid. It is metabolite of benzene in humans and serves as a biomarker of occupational exposure to benzene.. muconic acid : A hexadienedioic acid with unsaturation at positions 2 and 4.	2.05	1	0	muconic acid	biomarker; human xenobiotic metabolite
triphenyltin triphenyltin: triphenyltin derivatives widely used as pesticides; all of first source is triphenyltin cpds	2.03	1	0
rubidium Rubidium: An element that is an alkali metal. It has an atomic symbol Rb, atomic number 37, and atomic weight 85.47. It is used as a chemical reagent and in the manufacture of photoelectric cells.	2.03	1	0	alkali metal atom
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	3.15	5	0	boron group element atom; elemental aluminium; metal atom
levorphanol Levorphanol: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection.	2.03	1	0	morphinane alkaloid
strontium Strontium: An element of the alkaline earth family of metals. It has the atomic symbol Sr, atomic number 38, and atomic weight 87.62.	2.1	1	0	alkaline earth metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.9	2	0	metal atom; pnictogen
alternariol alternariol: structure. alternariol : A benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alternaria species, which are the most common mycoflora infecting small grain cereals worldwide.	2.25	1	0	benzochromenone; phenols	EC 3.1.1.8 (cholinesterase) inhibitor; metabolite; mycotoxin
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	3.45	7	0	metalloid atom; pnictogen	micronutrient
manganite [no description available]	2.08	1	0
indium Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.	2.17	1	0	boron group element atom
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	2.05	1	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
gallium Gallium: A rare, metallic element designated by the symbol, Ga, atomic number 31, and atomic weight 69.72.. gallium atom : A metallic element predicted as eka-aluminium by Mendeleev in 1870 and discovered by Paul-Emile Lecoq de Boisbaudran in 1875. Named in honour of France (Latin Gallia) and perhaps also from the Latin gallus cock, a translation of Lecoq.	3.1	4	0	boron group element atom
ramipril Ramipril: A long-acting angiotensin-converting enzyme inhibitor. It is a prodrug that is transformed in the liver to its active metabolite ramiprilat.. ramipril : A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.. quark : Quarks comprise one of two classes of the fundamental particles. Quarks possess fractional electric charges and are not observed in free state. The word "quark" first appears in James Joyce's Finnegans Wake and has been chosen by Murray Gell-Mann as a name for fundamental building blocks of particles.	2.11	1	0	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug
batimastat batimastat: structure given in first source; a synthetic matrix metalloproteinase inhibitor. batimastat : A secondary carboxamide resulting from the formal condensation of the carboxy group of (2S,3R)-5-methyl-3-{[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2-[(thiophen-2-ylsulfanyl)methyl]hexanoic acid with the amino group of hydroxylamine. It a broad-spectrum matrix metalloprotease inhibitor.	2.08	1	0	hydroxamic acid; L-phenylalanine derivative; organic sulfide; secondary carboxamide; thiophenes; triamide	angiogenesis inhibitor; antineoplastic agent; matrix metalloproteinase inhibitor
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	2.05	1	0	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.95	4	0	chalcogen; nonmetal atom	macronutrient
ethyl oleate [no description available]	2.11	1	0	long-chain fatty acid ethyl ester	acaricide; plant metabolite
11-cis-vaccenyl acetate 11-cis-vaccenyl acetate: a volatile pheromone; a male-specific lipid that is transferred in the ejaculate to females during copulation	2.08	1	0	acetate ester
geldanamycin [no description available]	2.41	2	0
methyl oleate [no description available]	2.08	1	0	fatty acid methyl ester
germacrene d germacrene D: RN in 9th CI Form Index for unspecified stereoisomer: 37839-63-7	2.13	1	0
plastoquinone [no description available]	1.99	1	0	plastoquinone
diphenylhexatriene Diphenylhexatriene: A fluorescent compound that emits light only in specific configurations in certain lipid media. It is used as a tool in the study of membrane lipids.	3.13	5	0	alkatriene	fluorochrome
2',4'-dihydroxychalcone 2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source	2.13	1	0
puerarin [no description available]	4.07	14	0	C-glycosyl compound; isoflavonoid
eleostearic acid eleostearic acid: RN given refers to cpd with unspecified isomeric designation	2.1	1	0	octadecatrienoic acid
3,4',5-trimethoxystilbene 3,4',5-trimethoxystilbene: structure in first source	2.46	2	0
bedaquiline bedaquiline: a diarylquinoline Antitubercular Agent. bedaquiline : A quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria.	2.31	1	0	aromatic ether; naphthalenes; organobromine compound; quinolines; tertiary alcohol; tertiary amino compound	antitubercular agent; ATP synthase inhibitor
enalapril Enalapril: An angiotensin-converting enzyme inhibitor that is used to treat HYPERTENSION and HEART FAILURE.. enalapril : A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).	2.04	1	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
nitrofurazone Nitrofurazone: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.. nitrofurazone : A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections.	3	4	0
catharanthine [no description available]	2.11	1	0	alkaloid ester; bridged compound; methyl ester; monoterpenoid indole alkaloid; organic heteropentacyclic compound; tertiary amino compound
sinomenine sinomenine: isolated from root of Sinomenium acutum; antirheumatic, antineuralgic	2.17	1	0	morphinane alkaloid
dimyristoylphosphatidylcholine 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).. dimyristoyl phosphatidylcholine : A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).	3.93	12	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
ecdysterone Ecdysterone: A steroid hormone that regulates the processes of MOLTING or ecdysis in insects. Ecdysterone is the 20-hydroxylated ECDYSONE.. 20-hydroxyecdysone : An ecdysteroid that is ecdysone substituted by a hydroxy group at position 20.	2.63	2	0	14alpha-hydroxy steroid; 20-hydroxy steroid; 22-hydroxy steroid; 25-hydroxy steroid; 2beta-hydroxy steroid; 3beta-sterol; ecdysteroid; phytoecdysteroid	animal metabolite; plant metabolite
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.45	2	0	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
acetyl acetonate [no description available]	2.03	1	0
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	4.07	14	0	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	3.58	8	0	carbon group element atom; metalloid atom; nonmetal atom
indium [no description available]	2.21	1	0
n-acetylmuramic acid N-acetylmuramic acid: RN given refers to D-Glucopyranose, (R)-isomer. N-acetyl-D-muramic acid : The pyranose form of N-acetylmuramic acid.	2.08	1	0	N-acetylmuramic acid
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	2.58	2	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	2.79	3	0	boron group element atom; metalloid atom; nonmetal atom	micronutrient
heroin Heroin: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed). heroin : A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.	2.41	2	0	morphinane alkaloid	mu-opioid receptor agonist; opioid analgesic; prodrug
dimethomorph dimethomorph: structure given in first source; RN given refers to cpd without isomeric designation. (Z)-dimethomorph : An enamide resulting from the formal condensation of (2Z)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylic acid with the amino group of morpholine. The agricultural fungicide dimethomorph is a mixture of (E)- and (Z)-dimethomorph; only the Z isomer has fungicidal activity.. dimethomorph : A mixture of (E)- and (Z)-dimethomorph in an unspecified ratio. It is used as a systemic fungicide used on vines, potatoes, and greenhouse crops; only the Z isomer has fungicidal activity.	2.5	2	0	aromatic ether; enamide; monochlorobenzenes; morpholine fungicide; tertiary carboxamide
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid: chromogen in glucose oxidase-peroxidase method for determining serum glucose; used in free radical scavenging assays; structure in first source	2.53	2	0
zerumbone zerumbone: RN given for (E,E,E)-isomer; structure in first source. zerumbone : A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillation from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.	2.06	1	0	cyclic ketone; sesquiterpenoid	anti-inflammatory agent; glioma-associated oncogene inhibitor; plant metabolite
sulindac sulfone sulindac sulfone: inhibits K-ras-dependent cyclooxygenase-2; sulfated analog of indomethacin;; CP248 is an antineoplastic agent that fosters microtubule depolymerization; structure in first source. sulindac sulfone : A sulfone metabolite of sulindac that inhibits cell growth by inducing apoptosis independently of cyclooxygenase inhibition. It inhibits the development and induces regression of premalignant adenomatous polyps. Lipoxygenase and Cox-2 inhibitor.	2.03	1	0	monocarboxylic acid; organofluorine compound; sulfone	apoptosis inducer; cyclooxygenase 2 inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor
phytochlorin phytochlorin: RN given refers to (2S-trans)-isomer; structure given in the first source	3.12	4	0
ici 118551 ICI 118551: RN given refers to (R,R)-(+-)-isomer; structure in first source; ICI 111581 is hydrochloride of ICI 118551. ICI 118551 : An indane substituted at position 7 by a methyl group and at position 4 by a 3-(isopropylamino)-2-hydroxybutoxy group (the 2R,3S-diastereomer).	2.03	1	0	aromatic ether; indanes; secondary alcohol; secondary amino compound	beta-adrenergic antagonist
troxerutin troxerutin: used in treatment of venous disorders; structure; venoruton & oxerutin is a mixture of hydroxyethyl rutinosides	2.02	1	0
n-acetylsphingosine N-acetylsphingosine: inhibits phospholipase D. N-acetylsphingosine : A N-acylsphingosine that has an acetamido group at position 2.	2.03	1	0	N-acylsphingosine
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	2.08	1	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
epicinchonine epicinchonine: structure in first source. cinchonine : Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	2.02	1	0	cinchona alkaloid
abscisic acid Abscisic Acid: Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits.. (S)-2-trans-abscisic acid : A 2-trans-abscisic acid with (S)-configuration at the chiral centre.. (+)-abscisic acid : The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.	2.57	2	0	2-trans-abscisic acid
n-caproylsphingosine N-(hexanoyl)sphing-4-enine : An N-acylsphingosine consisting of sphing-4-enine bearing a hexanoyl group on nitrogen.	2.05	1	0	N-acylsphingosine
3,3'-dioctadecylindocarbocyanine 3,3'-dioctadecylindocarbocyanine: RN given refers to parent cpd. dilC18(3)(1+) : The cationic form of a C3 cyanine dye having 3,3-dimethyl-1-octadecylindoleinine units at each end.	2.43	2	0	Cy5 dye; indolium ion	fluorochrome
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	3.56	8	0	cyanine dye; organic iodide salt	fluorochrome
25-hydroxyvitamin d 2 25-Hydroxyvitamin D 2: 9,10-Secoergosta-5,7,10(19),22-tetraene-3,25-diol. Biologically active metabolite of vitamin D2 which is more active in curing rickets than its parent. The compound is believed to attach to the same receptor as vitamin D2 and 25-hydroxyvitamin D3.	2.08	1	0	hydroxycalciol; seco-ergostane; vitamin D	bone density conservation agent; human xenobiotic metabolite; nutraceutical
apaziquone apaziquone: structure given in first source; RN given refers to (E)-isomer	2.44	2	0	indoles
zearalenol zearalenol: RN given refers to (3S-(3R,7S,11E))-isomer	2.15	1	0
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2h-pyran-2-one 6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2H-pyran-2-one: structure given in first source; potent irreversible, mechanism-based inhibitor of myocardial calcium-independent phospholipase A2	2.06	1	0	naphthalenes
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	3.01	4	0	ammonium salt; inorganic sulfate salt	fertilizer
bisabolol bisabolol: monocyclic sesquiterpene alcohol with strong bacteriocidal effects, especilly against M. Tuberc.; isolated from seed plant Populus tacamacaha; RN given refers to cpd without isomeric desigation	3.38	6	0
kresoxim-methyl kresoxim-methyl: strobilurin analogue; an industrial fungicide. kresoxim-methyl : A carboxylic ester that is the methyl ester of (2E)-(methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}acetic acid. A fungicide for the control of scab on apples and pears and other fungal diseases on a wide range of crops.	2.04	1	0	aromatic ether; methoxyiminoacetate strobilurin antifungal agent; methyl ester; oxime O-ether	antifungal agrochemical; environmental contaminant; mitochondrial cytochrome-bc1 complex inhibitor; xenobiotic
4,4'-diisothiocyanostilbene-2,2'-disulfonic acid 4,4'-Diisothiocyanostilbene-2,2'-Disulfonic Acid: An inhibitor of anion conductance including band 3-mediated anion transport.	2.05	1	0
am-356 methanandamide: structure given in first source; RN given refers to (all-Z)-(+-)-isomer	2.42	2	0	fatty amide
rifamycin sv rifamycin SV: RN given refers to parent cpd; structure in Merck Index, 9th ed, #8009. rifamycin SV : A member of the class of rifamycins that exhibits antibiotic and antitubercular properties.	2.45	2	0	acetate ester; cyclic ketal; lactam; macrocycle; organic heterotetracyclic compound; polyphenol; rifamycins	antimicrobial agent; antitubercular agent; bacterial metabolite
mastoparan [no description available]	3.55	2	0	mastoparans; peptidyl amide	antimicrobial agent
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.07	1	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	3.29	6	0	chalcogen; nonmetal atom	micronutrient
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	3.21	5	0	chalcogen; metalloid atom
selenourea [no description available]	2.03	1	0
triethoxysilane [no description available]	2.08	1	0
octadecylsilane [no description available]	2.44	2	0
palonosetron Palonosetron: Isoquinoline and quinuclidine derivative that acts as a 5-HT3 RECEPTOR antagonist. It is used in the prevention of nausea and vomiting induced by cytotoxic chemotherapy, and for the prevention of post-operative nausea and vomiting.. palonosetron : An organic heterotricyclic compound that is an antiemetic used (as its hydrochloride salt) in combination with netupitant (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy.	2.05	1	0	azabicycloalkane; delta-lactam; organic heterotricyclic compound	antiemetic; serotonergic antagonist
(3S,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid Fluvastatin: An indole-heptanoic acid derivative that inhibits HMG COA REDUCTASE and is used to treat HYPERCHOLESTEROLEMIA. In contrast to other statins, it does not appear to interact with other drugs that inhibit CYP3A4.. (3S,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid : A (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which both chiral centres have S configuration.. fluvastatin : A racemate comprising equimolar amounts of (3R,5S)- and (3S,5R)-fluvastatin. An HMG-CoA reductase inhibitor, it is used (often as the corresponding sodium salt) to reduce triglycerides and LDL-cholesterol, and increase HDL-chloesterol, in the treatment of hyperlipidaemia.	2.08	1	0	(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
mevalonolactone mevalonolactone: RN given refers to unlabeled cpd without isomeric designation; structure. mevalonolactone : A racemate comprising equimolar amounts of (R)-mevalonolactone and (S)-mevalonolactone.	1.98	1	0	4-hydroxy-4-methyloxan-2-one	fungal metabolite; plant metabolite
raubasine raubasine: RN given refers to (19alpha)-isomer; structure	2.11	1	0	yohimban alkaloid
dizocilpine maleate Dizocilpine Maleate: A potent noncompetitive antagonist of the NMDA receptor (RECEPTORS, N-METHYL-D-ASPARTATE) used mainly as a research tool. The drug has been considered for the wide variety of neurodegenerative conditions or disorders in which NMDA receptors may play an important role. Its use has been primarily limited to animal and tissue experiments because of its psychotropic effects.. dizocilpine maleate : A maleate salt obtained by reaction of dizocilpine with one equivalent of maleic acid.	2	1	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
cholestanol Cholestanol: A cholesterol derivative found in human feces, gallstones, eggs, and other biological matter.	2.44	2	0	cholestanoid
s-(1,2-dichlorovinyl)cysteine S-(1,2-dichlorovinyl)cysteine: RN given refers to (L-Cys)-isomer; structure given in first source. S-(cis-1,2-dichlorovinyl)-L-cysteine : An S-(1,2-dichlorovinyl)-L-cysteine in which the dichlorovinyl group has cis- (Z-) geometry.	1.97	1	0	S-(1,2-dichlorovinyl)-L-cysteine
dolichols Dolichols: A class of polyprenols which contain approximately 20 isoprene residues. Although considered ISOPRENOIDS, they terminate with an alpha-saturated isoprenoid group at the hydroxy end of the molecule.	1.98	1	0	polyterpene
cilastatin [no description available]	2.25	1	0	carboxamide; L-cysteine derivative; non-proteinogenic L-alpha-amino acid; organic sulfide	EC 3.4.13.19 (membrane dipeptidase) inhibitor; environmental contaminant; protease inhibitor; xenobiotic
1-palmitoyl-2-oleoylphosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine: RN given refers to (Z)-isomer	3.86	11	0
latrunculin b latrunculin B: 14-membered macrolide attached to 2-thiazolidinone moiety; from Red Sea sponge Latrunculia magnifica; see also latrunculin A; structure given in first source. latrunculin B : A macrolide consisting of a 14-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica.	3.15	5	0	cyclic hemiketal; macrolide; oxabicycloalkane; thiazolidinone	actin polymerisation inhibitor; metabolite; toxin
bafilomycin a1 bafilomycin A1: from Streptomyces griseus; structure given in first source. bafilomycin A1 : The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.	3.14	5	0	cyclic hemiketal; macrolide antibiotic; oxanes	apoptosis inducer; autophagy inhibitor; bacterial metabolite; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; ferroptosis inhibitor; fungicide; potassium ionophore; toxin
dehydroergosterol dehydroergosterol : A phytosterol consiting of ergostane having double bonds at the 5,6-, 7,8- 9,11- and 22,23-positions as well as a 3beta-hydroxy group.	2.94	4	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; ergostanoid; phytosterols	biomarker; metabolite
involucrin involucrin: soluble precursor protein of cross-linked envelope characteristic of epidermal s. corneum synthesized by keratinocytes in natural & cultured human epithelia; see also related records for prekeratin & stratum corneum basic protein precursor	2.02	1	0
1,2-dioleoyloxy-3-(trimethylammonium)propane 1,2-dioleoyloxy-3-(trimethylammonium)propane: fluorescent probe for phospholipids; RN & structure given in first source	2.07	1	0
lumefantrine Lumefantrine: A fluorene derivative that is used in combination with ARTEMETHER for the treatment of MALARIA (see ARTEMETHER-LUMEFANTRINE DRUG COMBINATION).. lumefantrine : A member of the class of fluorenes that is 9-(p-chlorobenzylidene)-9H-fluorene which is substitutec by chlorine at positions 2 and 7, and by a 2-(dibutylamino)-1-hydroxyethyl group at position 4. An antimalarial drug used in combination with artemether for the treatment of multi-drug resistant strains of falciparum malaria.	2.15	1	0	fluorenes; monochlorobenzenes; secondary alcohol; tertiary amine	antimalarial
sphingosine phosphorylcholine sphingosine phosphorylcholine: a wound healing agent	2.52	2	0
concanamycin a concanamycin A: from Streptomyces diastatochromogenes S-45; inhibits vacuolar H+ ATPase. concanamycin A : A concanamycin in which the lactone ring contains 4 double bonds and is substituted by 4 methyl groups, 2 hydroxy groups, 2 methoxy groups and an ethyl group.	2.17	1	0	carbamate ester; concanamycin	antifungal agent; EC 3.6.3.14 (H(+)-transporting two-sector ATPase) inhibitor; metabolite
squalestatin 1 squalestatin 1: structure given in first source; inhibits both mammalian and fungal squalene synthetase; from fungus Phoma sp (Coelomycetes). zaragozic acid A : A polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase.	2.93	4	0	acetate ester; cyclic ketal; oxabicycloalkane; polyketide; tertiary alcohol; tricarboxylic acid	EC 2.5.1.21 (squalene synthase) inhibitor; fungal metabolite
1-palmitoyl-2-linoleoylphosphatidylcholine [no description available]	2.05	1	0
limaprost limaprost: RN given refers to (2E,11alpha,13E,15S,17S)-isomer	2.8	3	0	long-chain fatty acid
thermozymocidin thermozymocidin: a serine palmitoyltransferase inhibitor; FTY720 is an analog	2.99	4	0	alpha-amino fatty acid; hydroxy monocarboxylic acid; non-proteinogenic alpha-amino acid; sphingoid	antifungal agent; antimicrobial agent; antineoplastic agent; apoptosis inducer; EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor; fungal metabolite; immunosuppressive agent
9-hydroxy-10,12,15-octadecatrienoic acid 9-hydroxy-10,12,15-octadecatrienoic acid: structure given in first source; RN given refers to (S-(E,Z,Z))-isomer; cpd without isomeric designation not avail 1/90. 9(S)-HOTrE : A 9-HOTrE consisting of (10E,12Z,15Z)-octadecatrienoic acid in which the 9-hydroxy group has S-configuration.	2.01	1	0	9-HOTrE	plant metabolite
bacteriochlorophylls Bacteriochlorophylls: Pyrrole containing pigments found in photosynthetic bacteria.	2.13	1	0
sanshool sanshool: isolated from the stem bark of Zanthoxylum liebmannianum; RN given for (E,E,Z,E)-isomer; structure in first source	2.17	1	0	fatty amide
1,2-linoleoylphosphatidylcholine 1,2-linoleoylphosphatidylcholine: used for premature induction of labor in rabbits; RN given refers to (all Z)-isomer	2.76	3	0
bifenthrin bifenthrin: a type I pyrethroid. bifenthrin : A carboxylic ester obtained by formal condensation of cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid and [(2-methyl-1,1'-biphenyl)-3-yl]methanol.. kappa-bifenthrin : A carboxylic ester obtained by formal condensation of the carboxy group of (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid with the hydroxy group of [(2-methyl-1,1'-biphenyl)-3-yl]methanol.	2.44	2	0	carboxylic ester; cyclopropanecarboxylate ester; cyclopropanes; organochlorine compound; organofluorine compound	pyrethroid ester acaricide; pyrethroid ester insecticide
nb 598 NB 598: decreases serum total & LDL-cholesterol levels; structure given in first source; inhibits squalene epoxidase	2.06	1	0
1-stearoyl-2-oleoyl-sn-glycerol 1-octadecanoyl-2-[(9Z)-octadecenoyl]-sn-glycerol : A 1,2-diacyl-sn-glycerol that has stearoyl and oleoyl as the 1- and 2-acyl groups respectively.	2.07	1	0	1,2-diacyl-sn-glycerol; 1-stearoyl-2-oleoylglycerol; diacylglycerol 36:1	mouse metabolite
1-oleoyl-2-palmitoylphosphatidylcholine 1-oleoyl-2-palmitoylphosphatidylcholine: RN given refers to (Z)-isomer	2.05	1	0
cdw17 antigen [no description available]	2.74	3	0
trisialoganglioside gt1 [no description available]	2.02	1	0
i(3)so3-galactosylceramide Sulfoglycosphingolipids: GLYCOSPHINGOLIPIDS with a sulfate group esterified to one of the sugar groups.. 1-(3-O-sulfo-beta-D-galactosyl)-N-tetracosanoylsphingosine : A D-galactosyl-N-acylsphingosine having a sulfo group at the 3-position on the galactose ring and tetracosanoyl as the N-acyl group.	2.74	3	0	galactosylceramide sulfate; N-acyl-beta-D-galactosylsphingosine
prothioconazole prothioconazole: a fungicide. prothioconazole : A racemate comprising equal amounts of (R)- and (S)-prothioconazole. A fungicide for use both as a seed treatment and foliar spray to treat a variety of diseases in cereals.. 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione : A member of the class of triazoles that is 1,2,4-triazole-3-thione substituted at position 2 by a 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl group.	2.31	1	0	cyclopropanes; monochlorobenzenes; tertiary alcohol; thiocarbonyl compound; triazoles
rilpivirine [no description available]	2.15	1	0	aminopyrimidine; nitrile	EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor
alpha-cyperone alpha-cyperone: isolated from the rhizomes of Cyperus rotundus; structure in first source	3.14	1	0
engeletin engeletin: dihydroflavonol glycoside from the leaves of Stelechocarpus cauliflorus; structure in first source	2.11	1	0
beta-escin Escin: Pentacyclic triterpene saponins, biosynthesized from protoaescigenin and barringtogenol, occurring in the seeds of AESCULUS. It inhibits edema formation and decreases vascular fragility.	2.06	1	0	triterpenoid saponin
tanespimycin CP 127374: analog of herbimycin A	2.1	1	0	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound; secondary amino compound	antineoplastic agent; apoptosis inducer; Hsp90 inhibitor
fm1 43 FM1 43: labels motor nerve terminals in an activity-dependent fashion that involves dye uptake by synaptic vesicles that are recycling; structure given in second source	2.08	1	0	organic bromide salt; pyridinium salt; quaternary ammonium salt; tertiary amine	fluorochrome
cefpodoxime proxetil cefpodoxime proxetil: structure given in first source; prodrug for cefpodoxime. cefpodoxime proxetil : The 1-[(isopropoxycarbonyl)oxy]ethyl (proxetil) ester prodrug of cefpodoxime. After swallowing, hydrolysis of the ester group occurs in the intestinal epithelium, to release active cefpodoxime in the bloodstream. It is used to treat acute otitis media, pharyngitis, and sinusitis.	2.46	2	0	carboxylic acid; carboxylic ester; cephalosporin	antibacterial drug; prodrug
beta-escin [no description available]	6.47	13	1
glucoraphanin glucoraphanin: precursor of sulforaphane. glucoraphanin : A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide.	2.21	1	0	sulfoxide; thia-alkylglucosinolic acid
s-nitroso-n-acetylpenicillamine S-Nitroso-N-Acetylpenicillamine: A sulfur-containing alkyl thionitrite that is one of the NITRIC OXIDE DONORS.	2.21	1	0	nitroso compound; nitrosothio compound	nitric oxide donor; vasodilator agent
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2.21	1	0	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
sb 269970 SB 269970: a 5-HT(7) antagonist; structure in first source	2.03	1	0	sulfonamide
madecassic acid [no description available]	2.03	1	0
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	2.17	1	0	isoquinoline alkaloid fundamental parent; morphinane alkaloid
adenosine-3',5'-cyclic phosphorothioate adenosine-3',5'-cyclic phosphorothioate: RP-cAMP-S is a protein kinase A inhibitor; SP-cAMP-S is a protein kinase A agonist. (Sp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Sp-stereoisomer).. (Rp)-cAMPS : A nucleoside 3',5'-cyclic phosphorothioate having adenine as the nucleobase (the Rp-stereoisomer).	2	1	0	nucleoside 3',5'-cyclic phosphorothioate
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	2.49	2	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
org 2766 Org 2766: ACTH 4-9 (H-Met(O)-Glu-His-Phe-D-Lys-Phe-OH) analog in which 4-Met position of fragment substituted by 4-Met sulfoxide, 8-Arg replaced by 8-D-Lys & 9-Trp replaced by 9-Phe; RN given refers to (D-Lys)-isomer	1.98	1	0
enkephalin, leucine-2-alanine Enkephalin, Leucine-2-Alanine: A delta-selective opioid (ANALGESICS, OPIOID). It can cause transient depression of mean arterial blood pressure and heart rate.	2.4	2	0
nocloprost nocloprost: phalloidin transport inhibitor	3.37	1	1
tiapamil hydrochloride Tiapamil Hydrochloride: A phenylethylamine derivative that acts as a calcium antagonist showing hemodynamic effects in patients with acute myocardial infarction.	2.03	1	0
artesunate artesunic acid: RN given for (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,(2aR*))-isomer; succinic ester of artemether	2.02	1	0	artemisinin derivative; cyclic acetal; dicarboxylic acid monoester; hemisuccinate; semisynthetic derivative; sesquiterpenoid	antimalarial; antineoplastic agent; ferroptosis inducer
enkephalin-leu, ala(2)-arg(6)- enkephalin-Leu, Ala(2)-Arg(6)-: RN refers to (L-Arg-L-Tyr-D-Ala-L-Phe-L-Leu)-isomer	2.04	1	0
tipredane [no description available]	1.98	1	0	3-hydroxy steroid	androgen
bufogenin bufogenin: respiratory stimulant; from toad; structure. bufogenin : A steroid lactone of Chan su (toad venom), a Chinese medicine obtained from the skin venom gland of toads. A specific Na/K-ATPase protein inhibitor, it is used as a cardiotonic and central nervous system (CNS) respiratory agent, an analgesic and anesthetic, and as a remedy for ulcers.	2.5	2	0	epoxy steroid; steroid lactone	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
dutasteride Dutasteride: A 5-ALPHA-REDUCTASE INHIBITOR that is reported to inhibit both type-1 and type2 isoforms of the enzyme and is used to treat BENIGN PROSTATIC HYPERPLASIA.. dutasteride : An aza-steroid that is inasteride in which the tert-butyl group is replaced by a 2,5-bis(trifluoromethyl)phenyl group. A synthetic 4-azasteroid, dutasteride is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5alpha-reductase, an intracellular enzyme that converts testosterone to 5alpha-dihydrotestosterone. Dutasteride is used for the treatment of symptomatic benign prostatic hyperplasia in men with an enlarged prostate gland.	2.48	2	0	(trifluoromethyl)benzenes; aza-steroid; delta-lactam	antihyperplasia drug; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
ganaxolone ganaxolone: a selective, high-affinity, steroid modulator of the GABA(A) receptor; structure given in first source; RN given refers to (3alpha,5alpha)-isomer	2.25	1	0	corticosteroid hormone
panobinostat Panobinostat: An indole and hydroxamic acid derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used as an antineoplastic agent in combination with BORTEZOMIB and DEXAMETHASONE for the treatment of MULTIPLE MYELOMA.. panobinostat : A hydroxamic acid obtained by formal condensation of the carboxy group of (2E)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydroxylamine. A histone deacetylase inhibitor used (as its lactate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma.	2.54	2	0	cinnamamides; hydroxamic acid; methylindole; secondary amino compound	angiogenesis modulating agent; antineoplastic agent; EC 3.5.1.98 (histone deacetylase) inhibitor
rebaudioside a rebaudioside A: glucoside isolated from the leaves of the paraguayan shrub, Stevia rebaudiana; has taste properties superior to stevioside; structure in first source. rebaudioside A : A rebaudioside that is rubusoside in which the hydroxy groups at positions 3 and 4 of the beta-D-glucopyranosyloxy group at the 13alpha position have both been converted to the corresponding beta-D-glucopyranoside.	2.07	1	0	beta-D-glucoside; rebaudioside; tetracyclic diterpenoid	sweetening agent
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	3.87	11	0	borneol
leucyl-phenylalanine Leu-Phe : A dipeptide formed from L-leucine and L-phenylalanine residues.	2	1	0	dipeptide	metabolite
bromopyruvate [no description available]	2.1	1	0	2-oxo monocarboxylic acid anion
4-benzoylphenylalanine 4-benzoylphenylalanine: structure in first source; do not confuse with N-benzoylphenylalanine	2.15	1	0
staurosporine staurosporinium : Conjugate acid of staurosporine.	2.94	4	0	ammonium ion derivative
chloralose Chloralose: A derivative of CHLORAL HYDRATE that was used as a sedative but has been replaced by safer and more effective drugs. Its most common use is as a general anesthetic in animal experiments.	1.99	1	0
bufalin bufalin: cardiotonic; powerful anesthetic & one of the active constituents of the Chinese drug ch'an su(senso); in Japan prepared from skin of Bufo bufo garfarizans; RN given refers to (3beta,5beta)-isomer. bufalin : A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.	2.52	2	0	14beta-hydroxy steroid; 3beta-hydroxy steroid	animal metabolite; anti-inflammatory agent; antineoplastic agent; cardiotonic drug
hypericum Hypericum: Genus of perennial plants in the family CLUSIACEAE (sometimes classified as Hypericaceae). Herbal and homeopathic preparations are used for depression, neuralgias, and a variety of other conditions. Hypericum contains flavonoids; GLYCOSIDES; mucilage, TANNINS; volatile oils (OILS, ESSENTIAL), hypericin and hyperforin.. 6-formamidopenicillanic acid : A penicillanic acid having a (6R)-formamido substituent.	2.05	1	0	penicillanic acids
taxane taxane: produced by Taxomyces andreanae	2	1	0	diterpene; terpenoid fundamental parent
chlorhexidine Chlorhexidine: A disinfectant and topical anti-infective agent used also as mouthwash to prevent oral plaque.. chlorhexidine : A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge.	3.79	10	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
formazans Formazans: Colored azo compounds formed by the reduction of tetrazolium salts. Employing this reaction, oxidoreductase activity can be determined quantitatively in tissue sections by allowing the enzymes to act on their specific substrates in the presence of tetrazolium salts.	2.45	2	0
aldicarb Aldicarb: Carbamate derivative used as an insecticide, acaricide, and nematocide.. aldicarb : The oxime carbamate resulting from the addition of 2-methyl-2-(methylsulfanyl)propanaldoxime to methyl isocyanate. A member of the class of oxime carbamate insecticides, aldicarb is a mixture of E and Z isomers; it is not known which isomer is more active.	2.02	1	0
gemifloxacin Gemifloxacin: A naphthyridine and fluoroquinolone derivative antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used for the treatment of community-acquired pneumonia and acute bacterial infections associated with chronic bronchitis.. gemifloxacin : A 1,4-dihydro-1,8-naphthyridine with a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a substituted pyrrolin-1-yl group at the 7-position.	2.11	1	0	1,8-naphthyridine derivative; fluoroquinolone antibiotic; monocarboxylic acid; quinolone antibiotic	antibacterial drug; antimicrobial agent; topoisomerase IV inhibitor
triacsin c triacsin C: from Streptomyces No. 1228; structure given in first source; an acyl-CoA synthetase antagonist. triacsin C : A nitroso compound that is N-undecylnitrous hydrazide carrying double bonds at positions 1,2,4, and 7. It is a long-chain fatty acyl CoA synthetase inhibitor and interferes with lipid metabolism by inhibiting the de novo synthesis of glycerolipids and cholesterol esters.	2.03	1	0	hydrazone; nitroso compound; olefinic compound	antimalarial; apoptosis inhibitor; bacterial metabolite; EC 3.1.1.64 (retinoid isomerohydrolase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; vasodilator agent
dexlansoprazole Dexlansoprazole: The R-isomer of lansoprazole that is used to treat severe GASTROESOPHAGEAL REFLUX DISEASE.	2.15	1	0	benzimidazoles; sulfoxide
fpl 15896ar [no description available]	2.13	1	0
6-(2-aminopropyl)benzofuran 6-(2-aminopropyl)benzofuran: do not confuse with 1-(2, 3-dihydro-1-benzofuran-6-yl)propan-2-amine, which is also known as 6-APB	2.1	1	0
desvenlafaxine succinate Desvenlafaxine Succinate: A cyclohexanol and phenol derivative and metabolite of venlafaxine that functions as a SEROTONIN AND NORADRENALINE REUPTAKE INHIBITOR (SNRI) and is used as an ANTIDEPRESSIVE AGENT.	2.25	1	0
tebipenem tebipenem: an oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae; structure in first source	2.21	1	0
amoxicillin-potassium clavulanate combination Amoxicillin-Potassium Clavulanate Combination: A fixed-ratio combination of amoxicillin trihydrate and potassium clavulanate.	1.99	1	0
abiraterone acetate Abiraterone Acetate: An androstene derivative that inhibits STEROID 17-ALPHA-HYDROXYLASE and is used as an ANTINEOPLASTIC AGENT in the treatment of metastatic castration-resistant PROSTATE CANCER.. abiraterone acetate : A sterol ester obtained by formal condensation of the 3-hydroxy group of abiraterone with the carboxy group of acetic acid. A prodrug that is converted in vivo into abiraterone. Used for treatment of metastatic castrate-resistant prostate cancer.	2.08	1	0	pyridines; sterol ester	antineoplastic agent; EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor; prodrug
levamlodipine levamlodipine: used to treat angina and hypertension; structure in first source. (S)-amlodipine : The (4S)-enantiomer of amlodipine.	2.1	1	0	amlodipine
kb r7943 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate: inhibits the reverse mode of Na+/Ca++ exchange in cells expressing NCX1; structure in first source	2.1	1	0
ly 295427 [no description available]	2.05	1	0
jasplakinolide jasplakinolide: cyclodepsipeptide isolated from marine sponge Jaspis; active against Candida; RN refers to 2S-(2R,4E,6S,8R*)-isomer; structure in first source. jaspamide : A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity. It is an actin polymerization and stabilization inducer.	2.71	3	0	cyclodepsipeptide; phenols	actin polymerisation inducer; animal metabolite; antifungal agent; antineoplastic agent; apoptosis inducer; marine metabolite; neuroprotective agent
ro 28-2653 Ro 28-2653: a synthetic matrix metalloproteinase inhibitor reduces tumor growth and prolongs survival in a prostate cancer standard rat model	2.03	1	0
vestipitant [no description available]	2.13	1	0
tapentadol Tapentadol: An opioid analgesic, MU OPIOID RECEPTOR agonist, and noradrenaline reuptake inhibitor that is used in the treatment of moderate to severe pain, and of pain associated with DIABETIC NEUROPATHIES.	2.1	1	0	alkylbenzene
delta9-tetrahydrocannabinol hemisuccinate [no description available]	2.05	1	0
ursodoxicoltaurine tauroursodeoxycholate : An organosulfonate oxoanion that is the conjugate base of tauroursodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.. tauroursodeoxycholic acid : A bile acid taurine conjugate derived from ursoodeoxycholic acid.	1.99	1	0	bile acid taurine conjugate	anti-inflammatory agent; apoptosis inhibitor; bone density conservation agent; cardioprotective agent; human metabolite; neuroprotective agent
wck 771 WCK 771: structure in first source	2.03	1	0
ginsenoside m1 ginsenoside M1: structure in first source. ginsenoside C-K : A ginsenoside found in Panax species that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 20 has been converted to the corresponding beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.47	2	0	12beta-hydroxy steroid; 3beta-hydroxy-4,4-dimethylsteroid; 3beta-hydroxy steroid; beta-D-glucoside; ginsenoside; tetracyclic triterpenoid	anti-allergic agent; anti-inflammatory agent; antineoplastic agent; hepatoprotective agent; plant metabolite
paliperidone palmitate Paliperidone Palmitate: A benzisoxazole derivative and active metabolite of RISPERIDONE that functions as a DOPAMINE D2 RECEPTOR ANTAGONIST and SEROTONIN 5-HT2 RECEPTOR ANTAGONIST. It is an ANTIPSYCHOTIC AGENT used in the treatment of SCHIZOPHRENIA.. 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl hexadecanoate : A fatty acid ester obtained by the formal condensation of the carboxy group of hexadecanoic acid with the hydroxy group of 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one.. paliperidone palmitate : A racemate comprising equimolar amounts of (R)- and (S)-paliperidone palmitate. A long-acting injectable formulation of paliperidone (the major active metabolite of risperidone) that is used for treatment of schizophrenia.	2.78	3	0	1,2-benzoxazoles; fatty acid ester; heteroarylpiperidine; organofluorine compound; pyridopyrimidine
cabazitaxel cabazitaxel: an antineoplastic agent; structure in first source. cabazitaxel : A tetracyclic diterpenoid that is 10-deacetylbaccatin III having O-methyl groups attached at positions 7 and 10 as well as an O-(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl group attached at position 13. Acts as a microtubule inhibitor, binds tubulin and promotes microtubule assembly and simultaneously inhibits disassembly.	2.21	1	0	tetracyclic diterpenoid	antineoplastic agent; microtubule-stabilising agent
flag peptide FLAG peptide: engineered as a tag for immunoaffinity purification of genetically-engineered proteins; amino acid sequence given in first source; a polar octapeptide. FLAG peptide : An eight amino acid peptide consisting of L-aspartic acid, L-tyrosine, L-lysine, four L-aspartic acid residues, and L-lysine joined in sequence by peptide linkages. It is widely used as a fusion tag for the purification and detection of a wide variety of recombinant proteins.	2.03	1	0	peptide
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	3.15	5	0	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
avanafil [no description available]	2.13	1	0	aromatic amide; monocarboxylic acid amide; organochlorine compound; prolinols; pyrimidines	EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; vasodilator agent
ticagrelor Ticagrelor: An adenosine triphosphate analogue and reversible P2Y12 PURINORECEPTOR antagonist that inhibits ADP-mediated PLATELET AGGREGATION. It is used for the prevention of THROMBOEMBOLISM by patients with ACUTE CORONARY SYNDROME or a history of MYOCARDIAL INFARCTION.. ticagrelor : A triazolopyrimidine that is an adenosine isostere; the cyclopentane ring is similar to ribose and the nitrogen-rich [1,2,3]triazolo[4,5-d]pyrimidine moiety resembles the nucleobase adenine. A platelet aggregation inhibitor which is used for prevention of thromboembolic events in patients with acute coronary syndrome.	2.25	1	0	aryl sulfide; hydroxyether; organofluorine compound; secondary amino compound; triazolopyrimidines	P2Y12 receptor antagonist; platelet aggregation inhibitor
rivaroxaban Rivaroxaban: A morpholine and thiophene derivative that functions as a FACTOR XA INHIBITOR and is used in the treatment and prevention of DEEP-VEIN THROMBOSIS and PULMONARY EMBOLISM. It is also used for the prevention of STROKE and systemic embolization in patients with non-valvular ATRIAL FIBRILLATION, and for the prevention of atherothrombotic events in patients after an ACUTE CORONARY SYNDROME.. rivaroxaban : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-chlorothiophene-2-carboxylic acid with the amino group of 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. An anticoagulant used for prophylaxis of venous thromboembolism in patients with knee or hip replacement surgery.	2.17	1	0	aromatic amide; lactam; monocarboxylic acid amide; morpholines; organochlorine compound; oxazolidinone; thiophenes	anticoagulant; EC 3.4.21.6 (coagulation factor Xa) inhibitor
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	2.45	2	0	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
sb 3ct compound SB 3CT compound: a matrix metalloproteinase-2 inhibitor; structure in first source	2.41	1	0	aromatic ether
sucrose monolaurate sucrose monolaurate: RN given refers to monolaurate	2.05	1	0
g(m2) ganglioside G(M2) Ganglioside: A glycosphingolipid that accumulates due to a deficiency of hexosaminidase A or B (BETA-N-ACETYLHEXOSAMINIDASES), or GM2 activator protein, resulting in GANGLIOSIDOSES, heredity metabolic disorders that include TAY-SACHS DISEASE and SANDHOFF DISEASE.. ganglioside GM2 (18:0) : A sialotriaosylceramide that is N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine in which the acyl group on the sphingosine nitrogen is octadecanoyl. A constituent of natural ganglioside GM2.	4.4	4	0	N-acetyl-beta-D-galactosaminyl-(1->4)-alpha-N-acetylneuraminosyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-N-acylsphingosine; sialotriaosylceramide	antigen
ginsenoside rg3 ginsenoside Rg3: from Red ginseng; inhibits lung metastasis of tumor cells; structure given in first source. (20S)-ginsenoside Rg3 : A ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranosyl-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.	2.48	2	0	ginsenoside; glycoside; tetracyclic triterpenoid	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; plant metabolite
ym-254890 YM-254890: structure in first source	2.06	1	0
es-285 spisulosine: from marine organism, Spisula polynyma; structure in first source. 1-deoxysphinganine : A bioactive sphingoid, sphinganine, in which the terminal hydroxy group has been replaced by a hydrogen.	2.03	1	0	amino alcohol; sphingoid	antineoplastic agent
tocotrienols tocotrienol : A tocol in which the hydrocarbon chain at position 2 contains three double bonds.	2.17	1	0	diterpenoid
samarium sphingomyelin 16:0 : A sphingomyelin in which the total number of carbons contained in the sphingoid base and fatty acyl groups is 16 with zero double bonds.. sphingomyelin d18:1/16:0 : A sphingomyelin d18:1 in which the fatty acyl group contains 16 carbons and is fully saturated.. N-hexadecanoylsphingosine-1-phosphocholine : A sphingomyelin 34:1 in which the N-acyl group and sphingoid base are specified as hexadecanoyl and sphingosine respectively.	2.04	1	0	sphingomyelin d18:1/16:0	mouse metabolite
zeolites [no description available]	3.26	5	0
dimethoxycurcumin dimethoxycurcumin: has antineoplsatic activity; structure in first source	2.21	1	0
e-6087 enflicoxib: structure in first source	2.01	1	0
u 18666a 3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one: inhibits cycloartenol synthase. 3beta-(2-diethylaminoethoxy)androst-5-en-17-one hydrochloride : A hydrochloride obtained by reaction of 3beta-(2-diethylaminoethoxy)androst-5-en-17-one with one equivalent of hydrochloric acid. It is a cholesterol synthesis and transport inhibitor.	2.97	4	0	hydrochloride	antiviral agent; EC 1.3.1.72 (Delta(24)-sterol reductase) inhibitor; Hedgehog signaling pathway inhibitor; nicotinic antagonist; sterol biosynthesis inhibitor
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	5.21	47	0	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.77	3	0
trantinterol trantinterol: beta(2)-adrenoceptor agonist, structure in first source	2.21	1	0
deltorphin i, ala(2)- deltorphin I, Ala(2)-: isolated from skin extracts of frogs belonging to the genus Phyllomedusa; has affinity to opioid receptors	2.02	1	0	peptide
pimavanserin pimavanserin: A 5-HT(2A) inverse agonist; ACP-103 is the dihydroxybutanedioate (2:1) salt. It is used to treat hallucinations and delusions associated with PARKINSON DISEASE; structure in first source.. pimavanserin : A member of the class of ureas in which three of the four hydrogens are replaced by 4-fluorobenzyl, 1-methylpiperidin-4-yl, and 4-(isopropyloxy)benzyl groups. An atypical antipsychotic that is used (in the form of its tartrate salt) for treatment of hallucinations and delusions associated with Parkinson's disease.	2.25	1	0	aromatic ether; monofluorobenzenes; piperidines; tertiary amino compound; ureas	5-hydroxytryptamine 2A receptor inverse agonist; antipsychotic agent; serotonergic antagonist
delta-viniferin delta-viniferin: resveratrol dehydrodimer, an isomer of epsilon-viniferin; isolated from grapevine leaves; structure in first source. (2S,3S)-trans-delta-viniferin : A stilbenoid that is the (2S,3S)-trans-stereoisomer of delta-viniferin, obtained by cyclodimerisation of trans-resveratrol.	2.52	2	0	1-benzofurans; polyphenol; stilbenoid
heptakis(2,6-o-dimethyl)beta-cyclodextrin heptakis(2,6-O-dimethyl)beta-cyclodextrin: stimulant for Bordetella pertussis Phase I	6.31	145	0
dihydrokavain dihydrokavain: inhibits binding of batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated sodium channels	2.05	1	0	2-pyranones; aromatic ether
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	2.98	4	0
homocarnosine homocarnosine: RN given refers to parent cpd. homocarnosine : A histidine derivative that is histidine in which one of the hydrogens attached to the alpha-amino group has been replaced by a 4-aminobutanoyl group.	2.03	1	0	dipeptide zwitterion; dipeptide; homocarnosine; L-histidine derivative; N-acyl-L-alpha-amino acid anion; N-acyl-L-alpha-amino acid	human metabolite
alpha-synuclein alpha-Synuclein: A synuclein that is a major component of LEWY BODIES and plays a role in SYNUCLEINOPATHIES, neurodegeneration and neuroprotection.	3.47	7	0
artelinic acid artelinic acid: RN given refers to parent cpd without isomeric designation; benzyl ether of artemether	2.02	1	0
13-ethyl-gon-4-ene-3,17-dione 13-ethyl-gon-4-ene-3,17-dione: impurity found in Chinese norgestrel; RN given refers to cpd without isomeric designation	1.98	1	0
macelignan macelignan: an NSAID with antioxidant, free radical scavenging, and neuroprotective activities; structure in first source	2.15	1	0	lignan
homatropine methylbromide homatropine methylbromide: RN given refers to bromide (endo-(+-))-isomer	2.13	1	0
hydroxyibuprofen hydroxyibuprofen: major urinary metabolite of ibuprofen; structure in first source. 2-hydroxyibuprofen : A hydroxy monocarboxylic acid that is ibuprofen in which the methine proton on the isobutyl group has been replaced by a hydroxy group.	1.99	1	0	hydroxy monocarboxylic acid; tertiary alcohol	drug metabolite
carboxyibuprofen carboxyibuprofen: major urinary metabolite of ibuprofen; structure in first source. carboxyibuprofen : A dicarboxylic acid that is ibuprofen in which one of the methyl groups in the isobutyl portion has been converted to the corresponding carboxylic acid.	1.99	1	0	dicarboxylic acid	drug metabolite
demethylmirtazapine demethylmirtazapine: structure in first source. N-demethylmirtazapine : A benzazepine metabolite resulting from demethylation of the antidpressant, mirtazapine.	2.1	1	0	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; human xenobiotic metabolite; serotonergic antagonist
glaucocalyxin a glaucocalyxin A: chemical constituent of Rabdosia japonica var. glaucocalyx	2.54	2	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	2.97	4	0
homocamptothecin homocamptothecin: a DNA topoisomerase I antagonists, is a semisynthetic analogue of camptothecin (CPT) with a seven-membered beta-hydroxylactone resulting from the insertion of a mehthylene spacer between the alcohol moiety and the carboxyl function of the naturally occurring six-membered alpha-hydroxylactone of CPT; structure in first source	2.03	1	0	epsilon-lactone; organic heteropentacyclic compound; organonitrogen heterocyclic compound; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
per-6-amino-beta-cyclodextrin [no description available]	3.34	6	0
acebutolol alpha-D-glucosyl-(1->4)-alpha-D-mannose : An alpha-D-glucosyl-(1->4)-D-mannopyranose in which the anomeric hydroxy group has alpha configuration.	4.76	30	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
lactulose Lactulose: A synthetic disaccharide used in the treatment of constipation and hepatic encephalopathy. It has also been used in the diagnosis of gastrointestinal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p887). lactulose : A synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy.	1.98	1	0
1-phenyl-2-(1-pyrrolidinyl)-1-pentanone alpha-pyrrolidinovalerophenone: a designer drug; structure in first source	2.17	1	0
regorafenib [no description available]	2.55	2	0	(trifluoromethyl)benzenes; aromatic ether; monochlorobenzenes; monofluorobenzenes; phenylureas; pyridinecarboxamide	antineoplastic agent; hepatotoxic agent; tyrosine kinase inhibitor
arachidin-1 arachidin-1: structure in first source	2.11	1	0
radezolid [no description available]	2.31	1	0
tedizolid DA 7157: an anti-infective agent; structure in first source. tedizolid : A member of the class of pyridines that is pyridine which is substituted by a 2-methyl-2H-tetrazol-5-yl group at position 2 and by a 2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl group at position 5. It is used as its phosphate pro-drug used for the treatment of acute bacterial skin and skin structure infections caused by certain susceptible bacteria, including Staphylococcus aureus (including methicillin-resistant strains (MRSA) and methicillin-susceptible strains), various Streptococcus species, and Enterococcus faecalis.	3.16	4	0	carbamate ester; organofluorine compound; oxazolidinone; primary alcohol; pyridines; tetrazoles	antimicrobial agent; drug metabolite; protein synthesis inhibitor
delta-cyclodextrin delta-cyclodextrin: structure in first source	2.11	1	0
nystatin a1 Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.	4.81	31	0	nystatins
marizomib marizomib: a proteasome inhibitor from a marine bacterium Salinospora; structure in first source	2.03	1	0	beta-lactone; gamma-lactam; organic heterobicyclic compound; organochlorine compound; salinosporamide	antineoplastic agent; proteasome inhibitor
arachidin-3 arachidin-3: an NSAID and antioxidant isolated from Arachis hypogaea; structure in first source	2.11	1	0
8-hydroxymirtazapine [no description available]	2.1	1	0
aclidinium bromide aclidinium bromide: a long-acting, inhaled antimuscarinic; in phase I trial 8/2008. aclidinium bromide : A quaternary ammonium salt that is the bromide salt of aclidinium. A muscarinic acetylcholine M3 receptor antagonist, for the long-term maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD).	2.21	1	0	organic bromide salt; quaternary ammonium salt	bronchodilator agent; muscarinic antagonist
carfilzomib [no description available]	3.18	1	0	epoxide; morpholines; tetrapeptide	antineoplastic agent; proteasome inhibitor
cefdinir Cefdinir: A third-generation oral cephalosporin antibacterial agent that is used to treat bacterial infections of the respiratory tract and skin.. cefdinir : A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups.	3.56	2	0
jnj-26483327 JNJ-26483327: an orally active macrocyclic tyrosine kinase inhibitor for treatment of patients with advanced solid tumours; in Phase I trial, 9/2010	2.1	1	0
palmitoylcarnitine Palmitoylcarnitine: A long-chain fatty acid ester of carnitine which facilitates the transfer of long-chain fatty acids from cytoplasm into mitochondria during the oxidation of fatty acids.. O-palmitoyl-L-carnitine : An O-acyl-L-carnitine in which the acyl group is specified as palmitoyl (hexadecanoyl).	2.06	1	0	O-palmitoylcarnitine; saturated fatty acyl-L-carnitine	EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; human metabolite; mouse metabolite
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	3.54	8	0	benzoxazole
dextrothyroxine [no description available]	2.48	2	0
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	3.77	10	0
indocyanine green Indocyanine Green: A tricarbocyanine dye that is used diagnostically in liver function tests and to determine blood volume and cardiac output.	2.58	2	0	1,1-diunsubstituted alkanesulfonate; benzoindole; cyanine dye
scopolamine hydrobromide [no description available]	2.38	2	0
cinobufagin cinobufagin: isolated from Chinese medicinal preparation ch'an su; derived from toad venom	2.03	1	0	steroid lactone
vindoline [no description available]	2.11	1	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	2.94	4	0
tubulysin a tubulysin A: has both antiangiogenic and antineoplastic activities; structure in first source	2.05	1	0	carboxylic acid; diester
resorcinarene resorcinarene: structure in first source	3.53	2	0
24-hydroxycholesterol 24-hydroxycholesterol : An oxysterol that is cholesterol which is substituted by a hydroxy group at position 24.	2.1	1	0	24-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; oxysterol
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	4.1	14	0
alpha-amyrenone alpha-amyrenone: from Marsdenia officinalis Tsiang	2.31	1	0
rifamycins [no description available]	2.77	3	0
santalol santalol: combination of alpha and beta isomers	2.11	1	0
titanocene titanocene: C10-H10-Ti. titanocene : A bis(eta(5)-cyclopentadienyl)metal(II) having Ti(II) as the metal(II) species. The parent of the class of titanonocenes.	2.01	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	2.41	1	0
erythrosine Erythrosine: A tetraiodofluorescein used as a red coloring in some foods (cherries, fish), as a disclosure of DENTAL PLAQUE, and as a stain of some cell types. It has structural similarity to THYROXINE.. erythrosin B : An organic sodium salt that is the disodium salt of 2-(2,4,5,7-tetraiodo-6-oxido-3-oxo-8a,10a-dihydroxanthen-9-yl)benzoic acid.	2.44	2	0
mefloquine Mefloquine: A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.. mefloquine : A racemate composed of (+)-(11R,2'S)- and (-)-(11S,2'R)-enantiomers of mefloquine. An antimalarial agent which acts as a blood schizonticide; its mechanism of action is unknown.	2.47	2	0
estradiol 17-dihydrotrigonelline estradiol 17-dihydrotrigonelline: lipophilic dihydropyridine coupled estradiol; chemical system for delivery to central nervous system; structure given in first source	1.97	1	0
aflatoxin g1 aflatoxin G1: RN given refers to (7aR-cis)-isomer & is from 9th CI Form Index	1.99	1	0
maltoheptaose maltoheptaose: consists of seven glucose residues in a linear 1,4-alpha-linkage; substrate for determining alpha-amylase in serum; RN given refers to (D-glucopyranose)-isomer. maltoheptaose : A maltoheptaose heptasaccharide in which the glucose residue at the reducing end is in the aldehydo open-chain form.. alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-alpha-D-Glcp-(1->4)-D-Glcp : A maltoheptaose heptasaccharide consisting of six alpha-D-glucose residues and a D-glucose residue joined in sequence by (1->4) glycosidic bonds.	3.88	12	0	maltoheptaose heptasaccharide
curcumol [no description available]	2.58	2	0	sesquiterpenoid
1-stearoyl-2-arachidonoylglycerol 1-stearoyl-2-arachidonoylglycerol : A 1,2-diglyceride in which the acyl groups at positions 1 and 2 are specifed as stearoyl and arachidonoyl respectively.	2.07	1	0	1,2-diglyceride
icatibant icatibant: a potent bradykinin (B2) receptor antagonist; WIN 65365 is an L-Tic(7) stereoisomer. icatibant : A ten-membered synthetic oligopeptide consisting of D-Arg, Arg, Pro, Hyp, Gly, Thi, Ser, D-Tic, Oic, and Arg residues joined in sequrence. A bradykinin receptor antagonist used as its acetate salt for the treatment of acute attacks of hereditary angioedema in adult patients.	2.02	1	0
bioallethrin bioallethrin: RN given refers to (1R-(1alpha(S*),3beta))-isomer; see also record for ALLETHRIN which is cpd without isomeric designation. bioallethrin : A partly enantiopure variant of allethrin consisting of a mixture of two allethrin isomers (1R,trans;1R and 1R,trans;1S) in an approximate ratio of 1:1. Widely registered mosquito adulticide and spatial repellent. Bioallethrin is a synthetic pyrethroid used as a pesticide against household pest insects such as mosquitoes, houseflies and cockroaches.	2.52	2	0	allethrin; trans-allethrin
6-o-maltosyl-beta-cyclodextrin 6-O-maltosyl-beta-cyclodextrin: structure given in first source; forms inclusion complexes with p-nitrophenol	4.17	16	0
cyanidin-3-o-beta-glucopyranoside cyanidin-3-O-beta-glucopyranoside: a natural compound distributed in several fruits & vegetables, such as strawberry, rhubarb, cherry, red cabbage, red onion, cranberries, etc.	2.41	1	0
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	3.16	5	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	3.77	10	0
gw 4869 GW 4869: inhibits neutral sphingomyelinase; structure in first source	2.07	1	0
calcitonin [no description available]	2.94	4	0
melitten Melitten: Basic polypeptide from the venom of the honey bee (Apis mellifera). It contains 26 amino acids, has cytolytic properties, causes contracture of muscle, releases histamine, and disrupts surface tension, probably due to lysis of cell and mitochondrial membranes.	2.97	4	0
atrial natriuretic factor Atrial Natriuretic Factor: A potent natriuretic and vasodilatory peptide or mixture of different-sized low molecular weight PEPTIDES derived from a common precursor and secreted mainly by the HEART ATRIUM. All these peptides share a sequence of about 20 AMINO ACIDS.	2.06	1	0	polypeptide
magainin 2 peptide, xenopus magainin 2 peptide, Xenopus: from skin of Xenopus laevis; 23-amino acid sequence given in first source; differs from magainin 1 by substitution of Lys instead of Gly at position 10 & Asn instead of Lys at position 22; also used to prevent development of malarial oocysts in mosquito vector; Z-12 is magainin 2 with Lys and Phe residues replaced with their respective D-isomers; homologue of the Xenopus laevis cement; GenBank AF004262 (mouse), AF007791, AF038451-2 (human)	2	1	0
hen egg lysozyme peptide (46-61) [no description available]	2.01	1	0
glycoprotein e2, hepatitis c virus glycoprotein E2, Hepatitis C virus: RN refers to quasispecies 4E; amino acid sequence known; caution: HCV also stands for hog cholera virus	2.01	1	0
humanin humanin: suppresses neuronal cell death induced by the Swedish mutant of amyloid precursor protein; suppresses neuronal cell death induced by three different types of FAD genes and amyloid beta; amino acid sequence in first source	2.04	1	0
gastrin heptadecapeptide, nle(15)- gastrin heptadecapeptide, Nle(15)-: minigastrin II is the hydrogen sulfate ester of the minigastrin I	2.02	1	0
gastrins Gastrins: A family of gastrointestinal peptide hormones that excite the secretion of GASTRIC JUICE. They may also occur in the central nervous system where they are presumed to be neurotransmitters.	2.02	1	0
gramicidin a Gramicidin: A group of peptide antibiotics from BACILLUS brevis. Gramicidin C or S is a cyclic, ten-amino acid polypeptide and gramicidins A, B, D are linear. Gramicidin is one of the two principal components of TYROTHRICIN.	2.71	3	0
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	5.23	3	1	peptide hormone
ceca1 protein, drosophila [no description available]	2.11	1	0
neuropeptide y Neuropeptide Y: A 36-amino acid peptide present in many organs and in many sympathetic noradrenergic neurons. It has vasoconstrictor and natriuretic activity and regulates local blood flow, glandular secretion, and smooth muscle activity. The peptide also stimulates feeding and drinking behavior and influences secretion of pituitary hormones.	2.76	3	0
iberiotoxin [no description available]	2.03	1	0
triacetyl-beta-cyclodextrin triacetyl-beta-cyclodextrin: structure in first source	3.42	7	0
cucurbit(8)uril cucurbit(8)uril: a macrocyclic polymer compound comprising 8 GLYCOLURIL units with methylene bridges	2.51	2	0
forapin Forapin: used as ointment for treatment of myositis & arthritis; contains bee venom, salicylate, nicotinate & vanillylnonamide	2.17	1	0	peptidyl amide; polypeptide	animal metabolite; antineoplastic agent; apoptosis inducer; EC 2.7.11.13 (protein kinase C) inhibitor; hepatoprotective agent; neuroprotective agent; venom
irl 1620 sovateltide: a potent, specific ligand for the endothelin-B receptor	2.04	1	0
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	2.76	2	0
oligonucleotides [no description available]	3.54	8	0
prosaptide prosaptide: 22-mer active peptide of prosaposin; amino acid sequence in first source	2.1	1	0
c-peptide C-Peptide: The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.	3.39	1	1
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	7.11	102	0	glycoside
sodium borate borax: see also sodium borate. borax : A hydrate that is the decahydrate form of disodium tetraborate.	2.31	1	0
endothelin-1 Endothelin-1: A 21-amino acid peptide produced in a variety of tissues including endothelial and vascular smooth-muscle cells, neurons and astrocytes in the central nervous system, and endometrial cells. It acts as a modulator of vasomotor tone, cell proliferation, and hormone production. (N Eng J Med 1995;333(6):356-63)	2.73	3	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	5.41	57	0	1,2-diacyl-sn-glycero-3-phosphocholine
1,2-dicapryl-sn-3-glycerophosphocholine didecanoylphosphatidylcholine: permeation enhancer. 1,2-dicapryl-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine in which the acyl groups at positions 1 and 2 are specified as capryl (decanoyl).	2.03	1	0	1,2-diacyl-sn-glycero-3-phosphocholine; decanoate ester
vx-770 ivacaftor: a CFTR potentiator; structure in first source. ivacaftor : An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.	2.25	1	0	aromatic amide; monocarboxylic acid amide; phenols; quinolone	CFTR potentiator; orphan drug
chlorophyll a Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.	3.27	6	0	chlorophyll; methyl ester	cofactor
vendex Torque: The rotational force about an axis that is equal to the product of a force times the distance from the axis where the force is applied.	2.03	1	0	organotin acaricide
hoe 33342 bisbenzimide ethoxide trihydrochloride: benzimidazole fluorescent dye	2.07	1	0
sodium salicylate [no description available]	3.14	5	0	organic molecular entity
sphingosine kinase [no description available]	2.07	1	0
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	4.53	5	1
pinoresinol pinoresinol: in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol. pinoresinol : A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl groups.	2.11	1	0
n-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide N-cyclopropyl-5-(thiophen-2-yl)isoxazole-3-carboxamide: has antineoplastic activity; structure in first source	2.13	1	0	aromatic amide; heteroarene
hydrocortisone sodium phosphate hydrocortisone sodium phosphate: RN given refers to (11beta)-isomer. cortisol phosphate(2-) : A steroid phosphate oxoanion which is the dianion obtained by deprotonation of the phosphate OH groups of cortisol phosphate.	2.39	2	0	steroid phosphate oxoanion
calpain Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.	2.42	2	0
tetronic 701 tetronic 701: series of surface-active block polymers with added hydrophilic (polyoxyethylene) and hydrophobic (polyoxypropylene) side chains to ethylene-diamine; used as a drug carrier	2.1	1	0
lucifer yellow lucifer yellow: RN given refers to di-Li salt	2.03	1	0	organic lithium salt	fluorochrome
sapogenins Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.	3.08	4	0
1,2,4-trioxane 1,2,4-trioxane: structure in first source	2.07	1	0
n-methylcarbamate N-methylcarbamate: RN given refers to parent cpd	2.58	2	0	amino-acid anion
ilexgenin a ilexgenin A: extract from the leaves of the plant	2.08	1	0
chitosan [no description available]	8.36	204	0
9-(tetrahydro-2-furyl)-adenine [no description available]	2.07	1	0
1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine 1-O-palmitoyl-2-O-(5-oxovaleryl)-sn-glycero-3-phosphocholine : A 1,2-diacyl-sn-glycero-3-phosphocholine having palmitoyl and 5-oxovaleryl groups at the 1- and 2-positions respectively; major species at pH 7.3.	2.02	1	0	1,2-diacyl-sn-glycero-3-phosphocholine; aldehyde	apoptosis inducer
s-nitro-n-acetylpenicillamine S-nitro-N-acetylpenicillamine: a NO donor	2.02	1	0
bucladesine Bucladesine: A cyclic nucleotide derivative that mimics the action of endogenous CYCLIC AMP and is capable of permeating the cell membrane. It has vasodilator properties and is used as a cardiac stimulant. (From Merck Index, 11th ed). bucladesine : A 3',5'-cyclic purine nucleotide that is the 2'-butanoate ester and 6-N-butanoyl derivative of 3',5'-cyclic AMP.	3.27	6	0	3',5'-cyclic purine nucleotide
potassium iodate [no description available]	2.03	1	0
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2.13	1	0	inorganic sodium salt	bleaching agent; disinfectant
sodium bisulfite sodium bisulfite: has been used externally for parasitic skin diseases and as gastrointestinal antiseptic; structure. sodium hydrogensulfite : An inorganic sodium salt having hydrogensulfite as the counterion.	2.05	1	0	inorganic sodium salt; sulfite salt	allergen; food antioxidant; food colour retention agent; mutagen; reducing agent
sodium tetradecyl sulfate [no description available]	2.13	1	0
sarkosyl sarkosyl: RN given is for sarkosyl L, the parent cpd; structure	2.48	2	0
methyl orange methyl orange: indictor of pH with strong acids & bases; also used as reagent to form ion pairs with, and thereby isolate, certain compounds from biological material; minor descriptor (75-86); on-line & INDEX MEDICUS search AZO COMPOUNDS (75-86); file maintained to Azo cpds	2.89	3	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	2.25	1	0
xk 469 XK 469: structure in first source	2.03	1	0
merocyanine dye merocyanine dye: fluorescent dye used for studying axons 2 position on pyrimidine ring may be S or O; RN given refers to Na salt; structure	2.43	2	0
chiniofon Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.	3.08	4	0
methyl jasmonate [no description available]	4.11	14	0
phosphatidylinositol 4-phosphate phosphatidylinositol 4-phosphate : A phosphatidylinositol monophosphate carrying the phosphate group at the 4-position.	2.05	1	0
pci 32765 ibrutinib: a Btk protein inhibitor. ibrutinib : A member of the class of acrylamides that is (3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine in which the piperidine nitrogen is replaced by an acryloyl group. A selective and covalent inhibitor of the enzyme Bruton's tyrosine kinase, it is used for treatment of B-cell malignancies.	2.25	1	0	acrylamides; aromatic amine; aromatic ether; N-acylpiperidine; pyrazolopyrimidine; tertiary carboxamide	antineoplastic agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
ethyl cellulose [no description available]	3.14	5	0	glycoside
navitoclax [no description available]	2.11	1	0	aryl sulfide; monochlorobenzenes; morpholines; N-sulfonylcarboxamide; organofluorine compound; piperazines; secondary amino compound; sulfone; tertiary amino compound	antineoplastic agent; apoptosis inducer; B-cell lymphoma 2 inhibitor
egg white Egg White: The white of an egg, especially a chicken's egg, used in cooking. It contains albumin. (Random House Unabridged Dictionary, 2d ed)	2.21	1	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	3.5	7	0	BODIPY compound
quetiapine fumarate Quetiapine Fumarate: A dibenzothiazepine and ANTIPSYCHOTIC AGENT that targets the SEROTONIN 5-HT2 RECEPTOR; HISTAMINE H1 RECEPTOR, adrenergic alpha1 and alpha2 receptors, as well as the DOPAMINE D1 RECEPTOR and DOPAMINE D2 RECEPTOR. It is used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER and DEPRESSIVE DISORDER.	2.25	1	0	fumarate salt
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	3	4	0
trelstar Triptorelin Pamoate: A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE with D-tryptophan substitution at residue 6.	2.42	2	0
nonaarginine [no description available]	2.05	1	0
deslorelin deslorelin: Ovuplant is tradename for a short-term-release implant containing deslorelin acetate; RN given refers to D-isomer; RN for cpd without isomeric designation not avail 12/90	2.42	2	0	oligopeptide
tolterodine tartrate Tolterodine Tartrate: An ANTIMUSCARINIC AGENT selective for the MUSCARINIC RECEPTORS of the BLADDER that is used in the treatment of URINARY INCONTINENCE and URINARY URGE INCONTINENCE.	2.21	1	0	tartrate salt
mannans [no description available]	3.44	7	0
bms-790052 daclatasvir: an HCV NS5A inhibitor. daclatasvir : A member of the class of biphenyls that is a potent inhibitor of nonstructural protein 5A and is used (as its hydrochloride salt) for treatment of hepatitis C.	2.41	1	0	biphenyls; carbamate ester; carboxamide; imidazoles; valine derivative	antiviral drug; nonstructural protein 5A inhibitor
4'-geranyloxyferulic acid 4'-geranyloxyferulic acid: a colon cancer chemopreventive agent isolated from grapefruit skin; structure in first source	2.13	1	0
peptones Peptones: Derived proteins or mixtures of cleavage products produced by the partial hydrolysis of a native protein either by an acid or by an enzyme. Peptones are readily soluble in water, and are not precipitable by heat, by alkalis, or by saturation with ammonium sulfate. (Dorland, 28th ed)	2.41	1	0
lysophosphatidylserine lysophosphatidylserine: stimulates histamine secretion from isolated mast cells in mouse plasma. lysophosphatidylserine : An acylglycerophosphoserine resulting from partial hydrolysis of a phosphatidylserine, which removes one of the fatty acid groups. The structure is depicted in the image where R(1) = acyl, R(2) = H or where R(1) = H, R(2) = acyl. Formula C7H13NO9PR, where R represents the hydrocarbon chain of the fatty acyl group.. 1-stearoyl-sn-glycero-3-phosphoserine : A 1-acyl-sn-glycerophosphoserine in which the acyl group is specified as stearoyl (octadecanoyl).	2.05	1	0	1-acyl-sn-glycero-3-phosphoserine
prunin prunin: structure in first source	2.08	1	0
mk-7655 relebactam: structure in first source	2.25	1	0
glycolipids [no description available]	6.96	49	0
elafin Elafin: A secretory proteinase inhibitory protein that was initially purified from human SKIN. It is found in a variety mucosal secretions and is present at high levels in SPUTUM. Elafin may play a role in the innate immunity (IMMUNITY, INNATE) response of the LUNG.	2.21	1	0
piperidines Piperidines: A family of hexahydropyridines.	5.49	24	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	4	13	0
GS-441524 [no description available]	2.94	3	0	aromatic amine; C-nucleoside; nitrile; pyrrolotriazine	anticoronaviral agent; antiviral agent; drug metabolite
avicin g avicin G: from the seed pods of the desert legume plant Acacia victoriae; structure in first source	3.17	1	0
siponimod siponimod: S1P receptor modulator	2.21	1	0
shepherdin shepherdin: a cell permeable peptidomimetic drug derived from a survivin peptide fragment K79-L87 that binds to ATP pocket of HSP90; anticancer agent	2.05	1	0
mephedrone mephedrone: a beta-keto (bk) designer drug; Central Nervous System Stimulants. mephedrone : An aromatic ketone that is propiophenone substituted at C-4 and at C-beta with methyl and methylamino groups respectively. It is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes.	2.52	2	0	amphetamines; aromatic ketone; secondary amino compound	environmental contaminant; xenobiotic
fosinopril Fosinopril: A phosphinic acid-containing angiotensin-converting enzyme inhibitor that is effective in the treatment of hypertension. It is a prodrug that is converted to its active metabolite fosinoprilat.. fosinopril : A phosphinate ester-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. It is used for the treatment of hypertension and heart failure. A pro-drug, it is hydrolysed in vivo to the corresponding phosphininc acid, fosinoprilat, which is the active metabolite.	2.06	1	0
sofosbuvir Sofosbuvir: A uridine monophosphate analog inhibitor of HEPATITIS C VIRUS (HCV) polymerase NS5B that is used as an ANTIVIRAL AGENT in the treatment of CHRONIC HEPATITIS C.. sofosbuvir : A nucleotide conjugate that is used in combination with ledipasvir (under the trade name Harvoni) for the treatment of chronic hepatitis C genotype 1 infection.	2.41	1	0	isopropyl ester; L-alanyl ester; nucleotide conjugate; organofluorine compound; phosphoramidate ester	antiviral drug; hepatitis C protease inhibitor; prodrug
bufadienolide bufadienolide: isolated from liushen pills; RN given for (14beta)-isomer. bufadienolide : The simplest member of the class of bufadienolides that is bufanolide with unsaturation at positions 20 and 22.	2.01	1	0	bufadienolides
6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1h-benzimidazole 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole: antiparasitic; structure in first source	2.06	1	0
dinaciclib [no description available]	2.08	1	0	pyrazolopyrimidine
fructose-1,6-diphosphate fructose-1,6-diphosphate: RN refers to (D)-isomer	2	1	0
methylcellulose Methylcellulose: Methylester of cellulose. Methylcellulose is used as an emulsifying and suspending agent in cosmetics, pharmaceutics and the chemical industry. It is used therapeutically as a bulk laxative.	7.39	60	2
isoquercitrin [no description available]	2.52	2	0
di-4-aneppdhq di-4-ANEPPDHQ: a commercially available voltage-sensitive dye used for probing live primary and immortalized neurons; structure in first source	2.79	3	0
1,2-dioleoyl-sn-glycero-3-phosphoglycerol 1,2-dioleoyl-sn-glycero-3-phospho-(1'-sn-glycerol) : A 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) in which both acyl groups are specified as oleoyl.	2.21	1	0	1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)
6-ketocholestanol 6-ketocholestanol: RN given refers to the (3beta)-isomer; RN for cpd without isomeric designation not avail 5/90	2	1	0	cholestanoid
heme Heme: The color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins.. ferroheme : Any iron(II)--porphyrin coordination complex.. ferroheme b : Heme b in which the iron has oxidation state +2.. heme : A heme is any tetrapyrrolic chelate of iron.	2.53	2	0
heparitin sulfate Heparitin Sulfate: A heteropolysaccharide that is similar in structure to HEPARIN. It accumulates in individuals with MUCOPOLYSACCHARIDOSIS.	2.93	4	0
trifloxystrobin trifloxystrobin : The methyl ester of (2E)-(methoxyimino)[2-({[(E)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetic acid. A foliar applied fungicide for cereals which is particularly active against Ascomycetes, Deuteromycetes and Oomycetes	2.11	1	0
yellow 2g yellow 2G: RN given refers to parent cpd. lissamine fast yellow : An organic sodium salt that is the disodium salt of 2,5-dichloro-4-{5-hydroxy-3-methyl-4-[(4-sulfophenyl)diazenyl]pyrazol-1-yl}benzene-1-sulfonic acid. It is used as the erythrocyte stain in Garvey's method for elastic, fibrin and collagen as well as a substitute for martius yellow in Lendrum's MSB.	2.05	1	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	4.98	36	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
tetracycline Tetracycline: A naphthacene antibiotic that inhibits AMINO ACYL TRNA binding during protein synthesis.. tetracycline : A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.	3.04	4	0
chlortetracycline Chlortetracycline: A TETRACYCLINE with a 7-chloro substitution.. chlortetracycline : A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens.	2.71	3	0
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.02	1	0
minocycline Minocycline: A TETRACYCLINE analog, having a 7-dimethylamino and lacking the 5 methyl and hydroxyl groups, which is effective against tetracycline-resistant STAPHYLOCOCCUS infections.. minocycline : A tetracycline analogue having a dimethylamino group at position 7 and lacking the methyl and hydroxy groups at position 5.	2.38	2	0
methacycline Methacycline: A broad-spectrum semisynthetic antibiotic related to TETRACYCLINE but excreted more slowly and maintaining effective blood levels for a more extended period.. methacycline : A tetracycline that is the 6-methylene analogue of oxytetracycline, obtained by formal dehydration at position 6.	2.44	2	0
isoascorbic acid isoascorbic acid: food antioxidant; (L)-isomer is ascorbic acid; RN given refers to (D)-isomer; structure	1.99	1	0	ascorbic acid
salicylates Salicylates: The salts or esters of salicylic acids, or salicylate esters of an organic acid. Some of these have analgesic, antipyretic, and anti-inflammatory activities by inhibiting prostaglandin synthesis.. hydroxybenzoate : Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.. salicylates : Any salt or ester arising from reaction of the carboxy group of salicylic acid, or any ester resulting from the condensation of the phenolic hydroxy group of salicylic acid with an organic acid.. salicylate : A monohydroxybenzoate that is the conjugate base of salicylic acid.	5.11	10	1	monohydroxybenzoate	plant metabolite
dicumarol Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.	1.96	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; Hsp90 inhibitor; vitamin K antagonist
piroxicam [no description available]	11.73	61	16	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug
meclan [no description available]	2.03	1	0
mobic Meloxicam: A benzothiazine and thiazole derivative that acts as a NSAID and cyclooxygenase-2 (COX-2) inhibitor. It is used in the treatment of RHEUMATOID ARTHRITIS; OSTEOARTHRITIS; and ANKYLOSING SPONDYLITIS.. meloxicam : A benzothiazine that is piroxicam in which the pyridin-2-yl group is replaced by a 5-methyl-1,3-thiazol-2-yl group. A non-steroidal anti-inflammatory drug and selective inhibitor of COX-2, it is used particularly for the management of rheumatoid arthritis.	5.9	22	1	1,3-thiazoles; benzothiazine; monocarboxylic acid amide	analgesic; antirheumatic drug; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug
mobiflex tenoxicam : A thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short term treatment of acute musculoskeletal disorders including strains, sprains and other soft-tissue injuries.	3.37	1	1	heteroaryl hydroxy compound; monocarboxylic acid amide; pyridines; thienothiazine	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	5.09	41	0	benzenes; hydroxycoumarin; methyl ketone
bromadiolone [no description available]	2.02	1	0	diarylheptanoid
6-o-palmitoylascorbic acid [no description available]	2.17	1	0	fatty acid ester
bromfenacoum [no description available]	2.05	1	0	benzenes; naphthalenes; ring assembly
phenprocoumon Phenprocoumon: Coumarin derivative that acts as a long acting oral anticoagulant.. phenprocoumon : A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group.	2	1	0	hydroxycoumarin	anticoagulant; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor
4-hydroxycoumarin 2-hydroxychromone: structure	2.02	1	0	hydroxycoumarin
rolitetracycline Rolitetracycline: A pyrrolidinylmethyl TETRACYCLINE.. rolitetracycline : A derivative of tetracycline in which the amide function is substituted with a pyrrolidinomethyl group.	2.03	1	0
tetronasin tetronasin: RN refers to the Na-salt; from Streptomyces longisporoflavus	2.01	1	0	terpene glycoside
lornoxicam lornoxicam : A thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 6-chloro-4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain, primarily resulting from inflammatory diseases of the joints, osteoarthritis, surgery, sciatica and other inflammations.	4.66	3	2	heteroaryl hydroxy compound; monocarboxylic acid amide; organochlorine compound; pyridines; thienothiazine	antipyretic; non-narcotic analgesic; non-steroidal anti-inflammatory drug
piroxicam-beta-cyclodextrin piroxicam-beta-cyclodextrin: drug combination consisting of beta-cyclodextrin & piroxicam; RN given refers to unknown ratio	10.69	26	13
dolutegravir [no description available]	2.21	1	0	difluorobenzene; monocarboxylic acid amide; organic heterotricyclic compound; secondary carboxamide	HIV-1 integrase inhibitor
urmc-099 URMC-099: inhibits mixed lineage kinase 3	2.17	1	0
nickel nitrilotriacetic acid [no description available]	2.17	1	0
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	4.04	14	0
microcystin microcystin: microcystins have the general structure cyclo(D-Ala-L-X-D-erythro--methylisoasp-L-Y-Adda-D-isoGlu-N-methyldehydroAla) where X and Y are variable L-amino acids;. microcystin : A family of cyclic heptapeptide hepatotoxins produced by a number of cyanobacteria, the most notable of which is Microcystis, from which the name of the family is derived. Microcystins consist of a heptapeptide macrocycle made up of five non-protein amino acids and two protein amino acids.	2.13	1	0	peptide
kaolinite Kaolin: The most common mineral of a group of hydrated aluminum silicates, approximately H2Al2Si2O8-H2O. It is prepared for pharmaceutical and medicinal purposes by levigating with water to remove sand, etc. (From Merck Index, 11th ed) The name is derived from Kao-ling (Chinese: high ridge), the original site. (From Grant & Hackh's Chemical Dictionary, 5th ed). kaolin : An aluminosilicate soft white mineral named after the hill in China (Kao-ling) from which it was mined for centuries. In its natural state kaolin is a white, soft powder consisting principally of the mineral kaolinite, and varying amounts of other minerals such as muscovite, quartz, feldspar, and anatase. It is used in the manufacture of china and porcelain and also widely used in the production of paper, rubber, paint, drying agents, and many other products.	2.03	1	0	aluminosilicate mineral; mixture	antidiarrhoeal drug; excipient
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	3.33	6	0
transforming growth factor beta Transforming Growth Factor beta: A factor synthesized in a wide variety of tissues. It acts synergistically with TGF-alpha in inducing phenotypic transformation and can also act as a negative autocrine growth factor. TGF-beta has a potential role in embryonal development, cellular differentiation, hormone secretion, and immune function. TGF-beta is found mostly as homodimer forms of separate gene products TGF-beta1, TGF-beta2 or TGF-beta3. Heterodimers composed of TGF-beta1 and 2 (TGF-beta1.2) or of TGF-beta2 and 3 (TGF-beta2.3) have been isolated. The TGF-beta proteins are synthesized as precursor proteins.	3.46	7	0
phytoestrogens Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.	3.17	5	0
okadaic acid Okadaic Acid: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. It is produced by DINOFLAGELLATES and causes diarrhetic SHELLFISH POISONING.. okadaic acid : A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.	2.44	2	0	ketal
pyrethrins [no description available]	4.01	13	0
globotriaosylceramide globotriaosylceramide: receptor for Shigella. alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide : A glycotriaosylceramide having alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosyl component attached to the primary hydroxy function of a ceramide with undefined sphingoid base.	2.01	1	0
bgp 15 BGP 15: A PARP (poy(ADP)-ribose polymerase) inhibitor; structure in first source; do not confuse with BGP-15 calcipotriene cpd	2.06	1	0
4-nitrophenyl maltopentaoside 4-nitrophenyl maltopentaoside: RN given is for all alpha sugars	2	1	0
fti 277 FTI 277: a ras CAAX (C - Cys; A - aliphatic amino acid; X - Ser or Met) peptidomimetic; inhibits farnesyltransferase; blocks Ras oncogenic signaling by accumulating Ras/Raf complexes in the cytoplasm; structure given in first source	2.03	1	0
trp-lys-tyr-met-val-met Trp-Lys-Tyr-Met-Val-Met: a synthetic peptide, stimulates phosphoinositide hyrolysis in human leukocytes	2.01	1	0
agar Agar: A complex sulfated polymer of galactose units, extracted from Gelidium cartilagineum, Gracilaria confervoides, and related red algae. It is used as a gel in the preparation of solid culture media for microorganisms, as a bulk laxative, in making emulsions, and as a supporting medium for immunodiffusion and immunoelectrophoresis.. agar : A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.	2.13	1	0
3-methylmethcathinone 3-methylmethcathinone: synthetic street drug, structure in first source	2.17	1	0
greigite greigite: component of magnetosomes (membrane-bound magnetic crystals) in bacteria that causes them to be oriented in magnetic fields; used as biomarkers. greigite : An iron sulfide mineral with formula Fe3S4.	2.08	1	0	iron(2+) sulfides; iron(3+) sulfides; sulfide mineral	catalyst
hirudin Hirudin: A 65-residue polypeptide from LEECHES.	2.03	1	0
ephrin-a5 Ephrin-A5: A GLYCOINOSITOL PHOSPHOLIPID MEMBRANE ANCHOR containing ephrin found in developing tectum. It has been shown to mediate the bundling of cortical axons and repel the axonal growth of retinal ganglia axons. It is found in a variety of adult tissues of BRAIN; HEART; and KIDNEY.	2.07	1	0
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.05	1	0
contraceptives, postcoital Contraceptives, Postcoital: Contraceptive substances to be used after COITUS. These agents include high doses of estrogenic drugs; progesterone-receptor blockers; ANTIMETABOLITES; ALKALOIDS, and PROSTAGLANDINS.	2.03	1	0
ganglioside gm1alpha [no description available]	2.03	1	0
qs 21 [no description available]	3.39	1	1
lysophosphatidylinositol [no description available]	2.45	2	0
lysophosphatidylethanolamine lysophosphatidylethanolamine : A glycerophosphoethanolamine resulting from partial hydrolysis of a phosphatidylethanolamine, which removes one of the fatty acid groups. The structure is depicted in the image where R(1) = acyl, R(2) = H or where R(1) = H, R(2) = acyl.	2.01	1	0
caseins Caseins: A mixture of related phosphoproteins occurring in milk and cheese. The group is characterized as one of the most nutritive milk proteins, containing all of the common amino acids and rich in the essential ones.	3.67	9	0
ckd732 CKD732: angiogenesis inhibitor	2.02	1	0
nov 002 NOV 002: a 1000-to-1 mixture of glutathione disulfide and cisplatin that is used to increase efficacy of chemotherapy against advanced non-small cell lung cancer; modulates cellular redox balance	2.13	1	0
hydroxymethylnitrofurazone hydroxymethylnitrofurazone: structure in first source	2.04	1	0
phthalocyanine phthalocyanine : A tetrapyrrole fundamental parent that consists of four isoindole-type units, with the connecting carbon atoms in the macrocycle replaced by nitrogen.	3.59	8	0	phthalocyanines; tetrapyrrole fundamental parent
tetraphenylporphine tetraphenylporphyrin: structure in first source	2.8	3	0
g(m3) ganglioside G(M3) Ganglioside: A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.. alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/24:1(15Z)) : A sialotriaosylceramide consisting of beta-D-GalNAc-(1->4)-[alpha-Neu5Ac-(2->3)]-beta-D-Gal-(1->4)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/24:1(15Z)).	3.12	5	0	alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-ceramide; sialodiosylceramide; sialotriaosylceramide	mouse metabolite
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.46	2	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	4.69	27	0
lewis x antigen Lewis X Antigen: A trisaccharide antigen expressed on glycolipids and many cell-surface glycoproteins. In the blood the antigen is found on the surface of NEUTROPHILS; EOSINOPHILS; and MONOCYTES. In addition, Lewis X antigen is a stage-specific embryonic antigen.	2.03	1	0
glucagon-like peptide 2 Glucagon-Like Peptide 2: A 33-amino acid peptide derived from the C-terminal of PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. It stimulates intestinal mucosal growth and decreased apoptosis of ENTEROCYTES. GLP-2 enhances gastrointestinal function and plays an important role in nutrient homeostasis.	2.13	1	0
angiotensin i Angiotensin I: A decapeptide that is cleaved from precursor angiotensinogen by RENIN. Angiotensin I has limited biological activity. It is converted to angiotensin II, a potent vasoconstrictor, after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME.. angiotensin I : A ten amino acid peptide formed by renin cleavage of angiotensinogen. Angiotensin I has no direct biological function except that high levels can stimulate catecholamine production. It is metabolized to its biologically active byproduct angiotensin II, a potent vasoconstrictor, by angiotensin converting enzyme (ACE) through cleavage of the two terminal amino acids.. angiotensin I dizwitterion : A peptide zwitterion that is the dizwitterionic form of angiotensin I having both carboxy groups deprotonated and the aspartyl amino group and arginine side-chain protonated. It is the major species at pH 7.3.	2.72	3	0	angiotensin; peptide zwitterion	human metabolite; neurotransmitter agent
carbopol 941 Carbopol 981: high molecular mucoadhesive polymer substance	2.48	2	0
lipofectamine Lipofectamine: mediates gene transfer; a polycationic lipid reagent	2.13	1	0
nephrin nephrin: gene nephrin is mutated in congenital nephrotic syndrome; amino acid sequence in first source; GenBank F19541; RefSeq NM_019459 (mouse), NM_004646 (human), NM_022628 (rat)	2.47	2	0
oridonin [no description available]	2.96	4	0
gibberellins [no description available]	2.1	1	0
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	2.44	2	0
insulin glargine Insulin Glargine: A recombinant LONG ACTING INSULIN and HYPOGLYCEMIC AGENT that is used to manage BLOOD GLUCOSE in patients with DIABETES MELLITUS.	2.47	2	0
norgestrel Norgestrel: A synthetic progestational agent with actions similar to those of PROGESTERONE. This racemic or (+-)-form has about half the potency of the levo form (LEVONORGESTREL). Norgestrel is used as a contraceptive, ovulation inhibitor, and for the control of menstrual disorders and endometriosis.	2.03	1	0
s 8932 [no description available]	3.38	5	0	aromatic amine; C-nucleoside; carboxylic ester; nitrile; phosphoramidate ester; pyrrolotriazine	anticoronaviral agent; antiviral drug; prodrug
oxyntomodulin Glucagon-Like Peptides: Peptides derived from proglucagon which is also the precursor of pancreatic GLUCAGON. Despite expression of proglucagon in multiple tissues, the major production site of glucagon-like peptides (GLPs) is the INTESTINAL L CELLS. GLPs include glucagon-like peptide 1, glucagon-like peptide 2, and the various truncated forms.	3.38	1	1
as 1411 AGRO 100: an antineoplastic agent that inhibits nuclear factor-kappaB activation; base sequence in first source	2.11	1	0
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	3.64	9	0
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	4.72	6	1
cytochalasin d Cytochalasin D: A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.. cytochalasin D : An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.	4.45	21	0
lactoferrin Lactoferrin: An iron-binding protein that was originally characterized as a milk protein. It is widely distributed in secretory fluids and is found in the neutrophilic granules of LEUKOCYTES. The N-terminal part of lactoferrin possesses a serine protease which functions to inactivate the TYPE III SECRETION SYSTEM used by bacteria to export virulence proteins for host cell invasion.	3.41	6	0
digitonin Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.	2.73	3	0
catalpol catalpol: component of dihuang; RN given refers to (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-isomer; RN for cpd without isomeric designation not avail 12/92	2.1	1	0
2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone 2,5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1,4-benzoquinone: structure in first source	2.01	1	0
carboxymethyl-beta-cyclodextrin [no description available]	5.77	79	0
orabase Orabase: used in therapy of oral mucosal ulcers	5.77	26	0
apyrase Apyrase: A calcium-activated enzyme that catalyzes the hydrolysis of ATP to yield AMP and orthophosphate. It can also act on ADP and other nucleoside triphosphates and diphosphates. EC 3.6.1.5.	2.06	1	0
thromboplastin Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.	2.43	2	0
muramidase Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.	4.79	30	0
caloxin 2a1 [no description available]	2.1	1	0
amyloid beta-peptides amyloid beta-protein (1-40): although acutely neurotoxic in both rat & monkey cerebral cortex, neuronal degeneration in primates resembles more closely to that found in Alzheimer's disease; amino acid sequence has been determined	3.28	6	0
chondroitin sulfates Chondroitin Sulfates: Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.	3.14	5	0
exudates Malaysia: A parliamentary democracy with a constitutional monarch in southeast Asia, consisting of 11 states (West Malaysia) on the Malay Peninsula and two states (East Malaysia) on the island of BORNEO. It is also called the Federation of Malaysia. Its capital is Kuala Lumpur. Before 1963 it was the Union of Malaya. It reorganized in 1948 as the Federation of Malaya, becoming independent from British Malaya in 1957 and becoming Malaysia in 1963 as a federation of Malaya, Sabah, Sarawak, and Singapore (which seceded in 1965). The form Malay- probably derives from the Tamil malay, mountain, with reference to its geography. (From Webster's New Geographical Dictionary, 1988, p715 & Room, Brewer's Dictionary of Names, 1992, p329)	2.21	1	0
bixin bixin: structure. bixin : A carotenoic acid that is the 6'-monomethyl ester of 9'-cis-6,6'-diapocarotene-6,6'-dioic acid.	2.51	2	0
protopanaxatriol protopanaxatriol: triterpenoid sapogenin of ginsenosides from leaves of Panax ginseng; acid hydrolysis leads to panaxatriol. protopanaxatriol : A tetracyclic triterpenoid sapogenin (isolated from ginseng and notoginseng) that is that is dammarane which is substituted by hydroxy groups at the 3beta, 6alpha, 12beta and 20 pro-S positions and in which a double bond has been introduced at the 24-25 position.	2.76	2	0
tetra(4-n-methylpyridyl)porphine tetra(4-N-methylpyridyl)porphine: structure in first source	2.01	1	0
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	5.82	20	1	2-aminopurines; oxopurine	antimetabolite; antiviral drug
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	3.13	5	0	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
cyclic gmp Cyclic GMP: Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). 3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine.	3.17	5	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
sepiapterin sepiapterin: A substrate of sepiapterin reductase	2.54	2	0	sepiapterin
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.03	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.72	3	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	3	4	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.66	2	0	guanosines; purines D-ribonucleoside	fundamental metabolite
hypoxanthine [no description available]	2.07	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
inosine [no description available]	2.52	2	0	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
inosine triphosphate Inosine Triphosphate: Inosine 5'-(tetrahydrogen triphosphate). An inosine nucleotide containing three phosphate groups esterified to the sugar moiety. Synonym: IRPPP.	2.21	1	0	inosine phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
folic acid folcysteine: used to promote fertility in chickens. vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin.	5.22	43	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	2.52	2	0
guanosine 5'-o-(3-thiotriphosphate) Guanosine 5'-O-(3-Thiotriphosphate): Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes.	3.89	12	0	nucleoside triphosphate analogue
pheophytin a pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S,11S),4beta,21beta))-isomer	2.73	3	0
rifampin Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)	3.9	11	0	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor
clozapine Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.	3.31	6	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic
ganciclovir [no description available]	2.71	3	0	2-aminopurines; oxopurine	antiinfective agent; antiviral drug
olanzapine Olanzapine: A benzodiazepine derivative that binds SEROTONIN RECEPTORS; MUSCARINIC RECEPTORS; HISTAMINE H1 RECEPTORS; ADRENERGIC ALPHA-1 RECEPTORS; and DOPAMINE RECEPTORS. It is an antipsychotic agent used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER; and MAJOR DEPRESSIVE DISORDER; it may also reduce nausea and vomiting in patients undergoing chemotherapy.. olanzapine : A benzodiazepine that is 10H-thieno[2,3-b][1,5]benzodiazepine substituted by a methyl group at position 2 and a 4-methylpiperazin-1-yl group at position 4.	3.16	5	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake inhibitor
raltitrexed [no description available]	2.05	1	0	N-acyl-amino acid
syringaldazine syringaldazine: used for detection of laccase in sporophores of wood rotting fungi; structure	2.03	1	0
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.94	4	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
azaguanine Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.. 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.	2.02	1	0	nucleobase analogue; triazolopyrimidines	antimetabolite; antineoplastic agent; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
xanthopterin [no description available]	2.08	1	0
bropirimine [no description available]	2	1	0	pyrimidines
sildenafil citrate Sildenafil Citrate: A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.. sildenafil citrate : The citrate salt of sildenafil.	3.93	2	1	citrate salt	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
aprepitant Aprepitant: A morpholine neurokinin-1 (NK1) receptor antagonist that is used in the management of nausea and vomiting caused by DRUG THERAPY, and for the prevention of POSTOPERATIVE NAUSEA AND VOMITING.. aprepitant : A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors.	2.1	1	0	(trifluoromethyl)benzenes; cyclic acetal; morpholines; triazoles	antidepressant; antiemetic; neurokinin-1 receptor antagonist; peripheral nervous system drug; substance P receptor antagonist
direct yellow 4 dye Direct Yellow 4 dye: RN given refers to parent cpd	2.01	1	0
8-bromocyclic gmp 8-bromo-3',5'-cyclic GMP : A 3',5'-cyclic purine nucleotide that is 3',5'-cyclic GMP bearing an additional bromo substituent at position 8 on the guanine ring. A membrane permeable cGMP analogue that activates protein kinase G (PKG). It is 4.3-fold more potent than cGMP in activating PKG1alpha and promotes relaxation of tracheal and vascular smooth muscle tissue in vitro.	2.02	1	0	3',5'-cyclic purine nucleotide; organobromine compound	muscle relaxant; protein kinase G agonist
azure c Azure C: RN given refers to chloride. azure C : An organic chloride salt having 3-amino-7-(methylamino)phenothiazin-5-ium as the counterion.	2.03	1	0
nsc 614846 carbovir: structure given in first source; potent & selective anti-HIV agent. carbovir : Cyclopent-2-en-1-ylmethanol in which the 4-position is substituted by a 2-amino-6-hydroxy-9H-purin-9-yl group such that the two substitutents on the cyclopentene ring are in a cis relationship. The (-)-enantiomer, also known as carbovir, is a potent inhibitor of HIV replication replication in cell cultures.. (-)-carbovir : The (active) (-)-enantiomer of the carbocyclic analogue of 2',3'-dideoxy-2',3'-didehydroguanosine.	1.97	1	0	carbovir	HIV-1 reverse transcriptase inhibitor
5,10,15,20-tetra(4-hydroxyphenyl)porphyrin 5,10,15,20-tetra(4-hydroxyphenyl)porphyrin: structure in first source; tumor localizer; do not confuse with THPP	2.17	1	0
prodigiosin Prodigiosin: 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)- 2,2'-bi-1H-pyrrole. A toxic, bright red tripyrrole pigment from Serratia marcescens and others. It has antibacterial, anticoccidial, antimalarial, and antifungal activities, but is used mainly as a biochemical tool.. prodigiosin : A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.	2.15	1	0
8-nitroguanine [no description available]	2.17	1	0	oxopurine
ns 309 6,7-dichloro-1H-indole-2,3-dione 3-oxime: activates IK and SK calcium-activated channels; structure in first source	2.03	1	0
imidacloprid imidacloprid: systemic & contact insecticide exhibiting low mammalian toxicity; structure given in first source; it is one of the neonicotinoid insecticides, which acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. imidacloprid : An imidazolidine that is N-nitroimidazolidin-2-imine bearing a (6-chloro-3-pyridinyl)methyl substituent at position 1.	2.59	2	0	imidacloprid; imidazolidines; monochloropyridine	environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic
r 80122 R 80122: structure given in first source; inhibits cyclic nucleotide phosphodiesterase type III; RN given refers to the E- isomer; R 79595 has no isomeric designation; R 80123 is the Z-isomer	3.37	1	1
guanosine 5'-o-(2-thiotriphosphate) [no description available]	2.08	1	0
lipoteichoic acid lipoteichoic acid: lipopolysaccharides with an acyl group anchored to the cell membrane of gram-positive bacteria; functions as an adhesion molecule to facilitate the binding of bacteria to cells, colonization, and invasion; interacts with CD14 to induce NF-κB activation and inflammatory cytokine production; can function as surface antigen; inhibits remineraliztion of artificial lesions and surface-softened enamels;. lipoteichoic acid : A teichoic acid which is covalently bound to a lipid.	2.04	1	0
avermectin avermectin: produced by actinomycete, Streptomyces avermitilis; structure; see also records for specific avermectins. avermectin : Any of the macrolides obtained as fermentation products from the bacterium Streptomyces avermitilis and consisting of a 16-membered macrocyclic backbone that is fused both benzofuran and spiroketal functions and contains a disaccharide substituent. They have significant anthelmintic and insecticidal properties.	2.1	1	0
cholestyramine resin Cholestyramine Resin: A strongly basic anion exchange resin whose main constituent is polystyrene trimethylbenzylammonium Cl(-) anion.	2.93	4	0
eye [no description available]	4.11	15	0
quillaja saponins Quillaja Saponins: Natural detergents made up of a heterogeneous mixture of molecules having a triterpenoid core structure. They vary in aglycone (sapogenin) and sugar moieties, including glucose.	2.11	1	0
maltodextrin maltodextrin : A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.	4.22	16	0
acetylcellulose acetylcellulose: coating compound. cellulose acetate : A glucan derivative obtained through the esterification of cellulose by acetic anhydride or acetic acid, resulting in the substitution of some of the hydroxy groups of cellulose by acetyl groups. It is used in a variety of applications including base material for photographic film, clothing, membrane filters, coatings, food packaging, and as a frame material for eyeglasses.	3.34	6	0
carbidopa Carbidopa: An inhibitor of DOPA DECARBOXYLASE that prevents conversion of LEVODOPA to dopamine. It is used in PARKINSON DISEASE to reduce peripheral adverse effects of LEVODOPA. It has no anti-parkinson activity by itself.. carbidopa : The hydrate of 3-(3,4-dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.	2	1	0
succinoglycan succinoglycan: extracellular heteropolysaccharides from Rhizobium meliloti; polymer of octasacharide subunits, one pyruvate, one acetyl & one succinyl group per subunit	2.6	1	0
thienorphine thienorphine: structure in first source	2.07	1	0
concanavalin a Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.	4	13	0
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	2	1	0
dinitrobenzenes Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.	3.13	5	0
biphenylylacetic acid biphenylylacetic acid: metabolite of BHD 7538; RN given refers to cpd with unspecified locants for acetic acid moities	3.49	8	0
2',7'-bis(carboxyethyl)-5(6)-carboxyfluorescein [no description available]	2.03	1	0
thrombin aptamer thrombin aptamer: nucleotide sequence given in first source; a synthetic polynucleotide	2.78	3	0
octaarginine octaarginine: structure in first source	2.8	3	0
phosphatidylbutanol [no description available]	2.05	1	0
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.81	3	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.95	4	0
cnicin cnicin: extract from CENTAUREA BENEDICTA	2.31	1	0
filipin Filipin: A complex of polyene antibiotics obtained from Streptomyces filipinensis. Filipin III alters membrane function by interfering with membrane sterols, inhibits mitochondrial respiration, and is proposed as an antifungal agent. Filipins I, II, and IV are less important.	5.68	76	0
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	4.85	32	0

Condition	Relationship Strength	Studies	Trials
Amyloid Deposits [description not available]	2.75	3	0
Acute Confusional Senile Dementia [description not available]	4.26	17	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	4.26	17	0
Elevated Cholesterol [description not available]	4.59	9	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	4.59	9	0
Congenital Zika Syndrome [description not available]	2.69	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	10.58	115	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.69	2	0
Benign Neoplasms [description not available]	8.21	87	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	8.21	87	1
Palmoplantaris Pustulosis [description not available]	2.9	3	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	2.9	3	0
Extravascular Hemolysis [description not available]	5.35	53	0
Age-Related Osteoporosis [description not available]	3.2	5	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	5.35	53	0
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	3.2	5	0
Cancer-Associated Pain [description not available]	2.9	2	0
Ache [description not available]	9.83	22	8
Cancer Pain Pain that may be caused by or related to cellular, tissue, and systemic changes that occur during NEOPLASM growth, tissue invasion, and METASTASIS.	2.9	2	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	9.83	22	8
HIV Coinfection [description not available]	6.59	11	1
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	2.42	2	0
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	6.59	11	1
Cancer of Ovary [description not available]	3.66	9	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	3.66	9	0
Adenocarcinoma Of Kidney [description not available]	2.42	2	0
Cancer of Kidney [description not available]	3.08	5	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	2.42	2	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	3.08	5	0
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	5.31	52	0
Chronic Illness [description not available]	6.08	8	4
Innate Inflammatory Response [description not available]	9.71	47	1
Acute Disease Disease having a short and relatively severe course.	3.35	2	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	6.08	8	4
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	9.71	47	1
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.88	3	0
Cancer of Cervix [description not available]	3.41	6	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	3.41	6	0
Muscle Pain [description not available]	2.58	2	0
Allodynia [description not available]	6.03	23	1
Myalgia Painful sensation in the muscles.	2.58	2	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.52	2	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	3.23	5	0
Alloxan Diabetes [description not available]	4.2	15	0
Attachment Loss, Periodontal [description not available]	3.64	1	1
Pericementitis [description not available]	5.44	7	2
Periodontitis Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)	5.44	7	2
Malignant Melanoma [description not available]	4.29	18	0
Cancer of Skin [description not available]	2.82	3	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	4.29	18	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.82	3	0
Cancer of Pancreas [description not available]	4.48	8	0
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	4.48	8	0
Necrotizing Enterocolitis [description not available]	2.25	1	0
Amnionitis [description not available]	2.25	1	0
Infections, Ureaplasma [description not available]	2.25	1	0
Chorioamnionitis INFLAMMATION of the placental membranes (CHORION; AMNION) and connected tissues such as fetal BLOOD VESSELS and UMBILICAL CORD. It is often associated with intrauterine ascending infections during PREGNANCY.	2.25	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	13.55	40	9
Enterocolitis, Necrotizing ENTEROCOLITIS with extensive ulceration (ULCER) and NECROSIS. It is observed primarily in LOW BIRTH WEIGHT INFANT.	2.25	1	0
Colorectal Cancer [description not available]	3.73	9	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.73	9	0
Atherogenesis [description not available]	5.27	17	0
Atheroma [description not available]	4.49	7	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	5.27	17	0
Anasarca [description not available]	4.31	18	0
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	4.31	18	0
Acquired Immune Deficiency Syndrome [description not available]	3.84	2	1
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	3.84	2	1
Alcoholic Liver Diseases [description not available]	3.85	2	1
Liver Diseases, Alcoholic Liver diseases associated with ALCOHOLISM. It usually refers to the coexistence of two or more subentities, i.e., ALCOHOLIC FATTY LIVER; ALCOHOLIC HEPATITIS; and ALCOHOLIC CIRRHOSIS.	3.85	2	1
Infections, Coronavirus [description not available]	4.96	2	1
2019 Novel Coronavirus Disease [description not available]	6.76	6	1
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	4.96	2	1
Coronavirus Infections Virus diseases caused by the CORONAVIRUS genus. Some specifics include transmissible enteritis of turkeys (ENTERITIS, TRANSMISSIBLE, OF TURKEYS); FELINE INFECTIOUS PERITONITIS; and transmissible gastroenteritis of swine (GASTROENTERITIS, TRANSMISSIBLE, OF SWINE).	4.96	2	1
Schistosoma mansoni Infection [description not available]	2.52	2	0
Schistosomiasis mansoni Schistosomiasis caused by Schistosoma mansoni. It is endemic in Africa, the Middle East, South America, and the Caribbean and affects mainly the bowel, spleen, and liver.	2.52	2	0
Cancer of Liver [description not available]	4.35	18	0
Liver Neoplasms Tumors or cancer of the LIVER.	4.35	18	0
Cancer of Colon [description not available]	6.58	25	0
Colonic Neoplasms Tumors or cancer of the COLON.	6.58	25	0
Benign Neoplasms, Brain [description not available]	4.41	7	0
Astrocytoma, Grade IV [description not available]	3.06	4	0
Brain Neoplasms Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.	4.41	7	0
Glioblastoma A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.	3.06	4	0
Experimental Neoplasms [description not available]	4.23	17	0
Carcinoma, Non-Small Cell Lung [description not available]	3.51	7	0
Cancer of Lung [description not available]	4.65	26	0
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	3.51	7	0
Lung Neoplasms Tumors or cancer of the LUNG.	4.65	26	0
B16 Melanoma [description not available]	3.9	11	0
Invasiveness, Neoplasm [description not available]	3.81	10	0
Pain, Chronic [description not available]	3.27	5	0
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	3.27	5	0
Musculoskeletal Pain Discomfort stemming from muscles, LIGAMENTS, tendons, and bones.	2.87	3	0
Cardiovascular Stroke [description not available]	2.81	3	0
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.81	3	0
Neurovisceral Storage Disease with Vertical Supranuclear Ophthalmoplegia [description not available]	11.09	68	1
Niemann-Pick Disease, Type C An autosomal recessive lipid storage disorder that is characterized by accumulation of CHOLESTEROL and SPHINGOMYELINS in cells of the VISCERA and the CENTRAL NERVOUS SYSTEM. Type C (or C1) and type D are allelic disorders caused by mutation of the NPC1 gene, which encodes a protein that mediates intracellular cholesterol transport from LYSOSOMES. Clinical signs include hepatosplenomegaly and chronic neurological symptoms. Type D is a variant in people with a Nova Scotia ancestry.	11.09	68	1
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	2.57	2	0
Diabetes Mellitus, Adult-Onset [description not available]	5.64	6	1
Insulin Sensitivity [description not available]	4.57	5	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	5.64	6	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	4.57	5	1
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	2.57	2	0
Tuberculosis, Drug-Resistant [description not available]	2.15	1	0
Pulmonary Consumption [description not available]	2.15	1	0
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	2.15	1	0
Tuberculosis, Multidrug-Resistant Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.	2.15	1	0
Bacterial Pneumonia [description not available]	2.15	1	0
Acinetobacter Infections Infections with bacteria of the genus ACINETOBACTER.	2.15	1	0
Candida Infection [description not available]	3.85	2	1
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	3.04	4	0
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	3.85	2	1
Pneumonia Infection of the lung often accompanied by inflammation.	3.04	4	0
Pneumonia, Bacterial Inflammation of the lung parenchyma that is caused by bacterial infections.	2.15	1	0
Breast Cancer [description not available]	5.45	56	0
Breast Neoplasms Tumors or cancer of the human BREAST.	5.45	56	0
Nasopharyngeal Carcinoma A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.	2.54	2	0
Carcinoma, Anaplastic [description not available]	3.16	5	0
Cancer of Nasopharynx [description not available]	2.88	3	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	3.16	5	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.88	3	0
Experimental Mammary Neoplasms [description not available]	3.14	5	0
Carcinoma, Lewis Lung A carcinoma discovered by Dr. Margaret R. Lewis of the Wistar Institute in 1951. This tumor originated spontaneously as a carcinoma of the lung of a C57BL mouse. The tumor does not appear to be grossly hemorrhagic and the majority of the tumor tissue is a semifirm homogeneous mass. (From Cancer Chemother Rep 2 1972 Nov;(3)1:325) It is also called 3LL and LLC and is used as a transplantable malignancy.	2.74	3	0
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	2.77	3	0
Infections, Nematode [description not available]	3.56	1	1
Ovine Diseases [description not available]	4.88	4	2
Intestinal Diseases, Parasitic Infections of the INTESTINES with PARASITES, commonly involving PARASITIC WORMS. Infections with roundworms (NEMATODE INFECTIONS) and tapeworms (CESTODE INFECTIONS) are also known as HELMINTHIASIS.	3.56	1	1
Blood Pressure, High [description not available]	3.25	5	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	3.25	5	0
Autoimmune Diabetes [description not available]	3.09	1	0
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	3.09	1	0
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	3.09	1	0
Hypoglycemia A syndrome of abnormally low BLOOD GLUCOSE level. Clinical hypoglycemia has diverse etiologies. Severe hypoglycemia eventually lead to glucose deprivation of the CENTRAL NERVOUS SYSTEM resulting in HUNGER; SWEATING; PARESTHESIA; impaired mental function; SEIZURES; COMA; and even DEATH.	3.09	1	0
Sexually Transmitted Diseases Diseases due to or propagated by sexual contact.	2.17	1	0
Trichomoniasis, Human [description not available]	2.17	1	0
Trichomonas Vaginitis Inflammation of the vagina, marked by a purulent discharge. This disease is caused by the protozoan TRICHOMONAS VAGINALIS.	2.17	1	0
Bone Diseases Diseases of BONES.	3.09	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	3.26	5	0
Triple Negative Breast Neoplasms Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.	3.26	5	0
Protein Aggregation, Pathological A biochemical phenomenon in which misfolded proteins aggregate either intra- or extracellularly. Triggered by factors such as MUTATION; POST-TRANSLATIONAL MODIFICATIONS, and environmental stress, it is generally associated with ALZHEIMER DISEASE; PARKINSON DISEASE; HUNTINGTON DISEASE; and TYPE 2 DIABETES MELLITUS.	2.85	3	0
Legionellosis Infections with bacteria of the genus LEGIONELLA.	2.21	1	0
Niemann-Pick Disease [description not available]	7.36	11	0
Niemann-Pick Diseases A group of autosomal recessive disorders in which harmful quantities of lipids accumulate in the viscera and the central nervous system. They can be caused by deficiencies of enzyme activities (SPHINGOMYELIN PHOSPHODIESTERASE) or defects in intracellular transport, resulting in the accumulation of SPHINGOMYELINS and CHOLESTEROL. There are various subtypes based on their clinical and genetic differences.	7.36	11	0
Alveolalgia [description not available]	2.21	1	0
Infection, Postoperative Wound [description not available]	2.21	1	0
Anoxemia [description not available]	3.1	4	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	3.1	4	0
Cells, Neoplasm Circulating [description not available]	2.21	1	0
Cancer of Stomach [description not available]	2.61	2	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.61	2	0
Cirrhosis [description not available]	3.02	4	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	3.02	4	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	6.47	168	0
Adjuvant Arthritis [description not available]	3.46	7	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	3.25	5	0
Cancer of Esophagus [description not available]	2.58	2	0
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.58	2	0
Hyperlipemia [description not available]	4.4	4	1
Hyperlipidemias Conditions with excess LIPIDS in the blood.	4.4	4	1
Glial Cell Tumors [description not available]	3.75	10	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	3.75	10	0
Skin Aging The process of aging due to changes in the structure and elasticity of the skin over time. It may be a part of physiological aging or it may be due to the effects of ultraviolet radiation, usually through exposure to sunlight.	4.77	3	2
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	5.56	16	1
Abdominal Migraine [description not available]	2.42	2	0
Migraine Disorders A class of disabling primary headache disorders, characterized by recurrent unilateral pulsatile headaches. The two major subtypes are common migraine (without aura) and classic migraine (with aura or neurological symptoms). (International Classification of Headache Disorders, 2nd ed. Cephalalgia 2004: suppl 1)	2.42	2	0
Rodent Diseases Diseases of rodents of the order RODENTIA. This term includes diseases of Sciuridae (squirrels), Geomyidae (gophers), Heteromyidae (pouched mice), Castoridae (beavers), Cricetidae (rats and mice), Muridae (Old World rats and mice), Erethizontidae (porcupines), and Caviidae (guinea pigs).	2.1	1	0
Pocket, Periodontal [description not available]	2.55	2	0
Periodontal Pocket An abnormal extension of a gingival sulcus accompanied by the apical migration of the epithelial attachment and bone resorption.	2.55	2	0
African Sleeping Sickness [description not available]	2.1	1	0
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.1	1	0
Blood Poisoning [description not available]	2.1	1	0
MODS [description not available]	2.55	2	0
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	2.55	2	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.1	1	0
Acid beta-Glucosidase Deficiency [description not available]	2.81	3	0
Gaucher Disease An autosomal recessive disorder caused by a deficiency of acid beta-glucosidase (GLUCOSYLCERAMIDASE) leading to intralysosomal accumulation of glycosylceramide mainly in cells of the MONONUCLEAR PHAGOCYTE SYSTEM. The characteristic Gaucher cells, glycosphingolipid-filled HISTIOCYTES, displace normal cells in BONE MARROW and visceral organs causing skeletal deterioration, hepatosplenomegaly, and organ dysfunction. There are several subtypes based on the presence and severity of neurological involvement.	2.81	3	0
Acute Liver Injury, Drug-Induced [description not available]	3.6	8	0
Carbon Tetrachloride Poisoning Poisoning that results from ingestion, injection, inhalation, or skin absorption of CARBON TETRACHLORIDE.	2.49	2	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	3.6	8	0
Carcinoma, Epidermoid [description not available]	3.65	9	0
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	3.65	9	0
Infection, Toxoplasma gondii [description not available]	2.1	1	0
Toxoplasmosis The acquired form of infection by Toxoplasma gondii in animals and man.	2.1	1	0
Degenerative Diseases, Central Nervous System [description not available]	6.53	9	0
Neurodegenerative Diseases Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.	6.53	9	0
Cirrhosis, Liver [description not available]	2.1	1	0
Cardiomyopathies, Primary [description not available]	2.57	2	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.1	1	0
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	2.57	2	0
Diffuse Myofascial Pain Syndrome [description not available]	3.04	4	0
Fibromyalgia A common nonarticular rheumatic syndrome characterized by myalgia and multiple points of focal muscle tenderness to palpation (trigger points). Muscle pain is typically aggravated by inactivity or exposure to cold. This condition is often associated with general symptoms, such as sleep disturbances, fatigue, stiffness, HEADACHES, and occasionally DEPRESSION. There is significant overlap between fibromyalgia and the chronic fatigue syndrome (FATIGUE SYNDROME, CHRONIC). Fibromyalgia may arise as a primary or secondary disease process. It is most frequent in females aged 20 to 50 years. (From Adams et al., Principles of Neurology, 6th ed, p1494-95)	3.04	4	0
Adenocarcinoma, Basal Cell [description not available]	3.66	9	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	3.66	9	0
Human Trichinellosis [description not available]	3.14	5	0
Trichinellosis An infection with TRICHINELLA. It is caused by eating raw or undercooked meat that is infected with larvae of nematode worms TRICHINELLA genus. All members of the TRICHINELLA genus can infect human in addition to TRICHINELLA SPIRALIS, the traditional etiological agent. It is distributed throughout much of the world and is re-emerging in some parts as a public health hazard and a food safety problem.	3.14	5	0
Colitis, Granulomatous [description not available]	2.11	1	0
E coli Infections [description not available]	3.17	5	0
Crohn Disease A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.	2.11	1	0
Escherichia coli Infections Infections with bacteria of the species ESCHERICHIA COLI.	3.17	5	0
Cancer of Prostate [description not available]	4.52	22	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	4.52	22	0
Bacterial Disease [description not available]	2.61	2	0
Bacterial Infections Infections by bacteria, general or unspecified.	2.61	2	0
Cardiac Toxicity [description not available]	2.81	3	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.81	3	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.78	3	0
Allergic Conjunctivitis [description not available]	2.15	1	0
Conjunctivitis, Allergic Conjunctivitis due to hypersensitivity to various allergens.	2.15	1	0
Arterial Inflammation [description not available]	2.13	1	0
Coronary Restenosis Recurrent narrowing or constriction of a coronary artery following surgical procedures performed to alleviate a prior obstruction.	2.13	1	0
Craniofacial Pain [description not available]	3.26	5	0
Facial Pain Pain in the facial region including orofacial pain and craniofacial pain. Associated conditions include local inflammatory and neoplastic disorders and neuralgic syndromes involving the trigeminal, facial, and glossopharyngeal nerves. Conditions which feature recurrent or persistent facial pain as the primary manifestation of disease are referred to as FACIAL PAIN SYNDROMES.	3.26	5	0
Idiopathic Parkinson Disease [description not available]	3.09	4	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	3.09	4	0
Caliciviridae Infections Virus diseases caused by CALICIVIRIDAE. They include HEPATITIS E; VESICULAR EXANTHEMA OF SWINE; acute respiratory infections in felines, rabbit hemorrhagic disease, and some cases of gastroenteritis in humans.	2.15	1	0
Edema, Pulmonary [description not available]	2.04	1	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	2.04	1	0
Blood Clot [description not available]	2.46	2	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.46	2	0
Peritoneal Carcinomatosis [description not available]	2.46	2	0
Peritoneal Neoplasms Tumors or cancer of the PERITONEUM.	2.46	2	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	6.06	15	0
Bone Cancer [description not available]	2.77	3	0
Metastase [description not available]	3.29	6	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.77	3	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	3.29	6	0
Acne [description not available]	2.05	1	0
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.05	1	0
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	4.55	5	1
Fungal Diseases [description not available]	6.52	9	2
Critical Illness A disease or state in which death is possible or imminent.	3.9	4	0
Mycoses Diseases caused by FUNGI.	6.52	9	2
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	4.55	5	1
Bacillus anthracis Infection [description not available]	3.15	5	0
Anthrax An acute infection caused by the spore-forming bacteria BACILLUS ANTHRACIS. It commonly affects hoofed animals such as sheep and goats. Infection in humans often involves the skin (cutaneous anthrax), the lungs (inhalation anthrax), or the gastrointestinal tract. Anthrax is not contagious and can be treated with antibiotics.	3.15	5	0
Lung Adenocarcinoma [description not available]	2.47	2	0
Adenocarcinoma of Lung A carcinoma originating in the lung and the most common lung cancer type in never-smokers. Malignant cells exhibit distinct features such as glandular epithelial, or tubular morphology. Mutations in KRAS, EGFR, BRAF, and ERBB2 genes are associated with this cancer.	2.47	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.98	4	0
Celiac Sprue [description not available]	2.06	1	0
Celiac Disease A malabsorption syndrome that is precipitated by the ingestion of foods containing GLUTEN, such as wheat, rye, and barley. It is characterized by INFLAMMATION of the SMALL INTESTINE, loss of MICROVILLI structure, failed INTESTINAL ABSORPTION, and MALNUTRITION.	2.06	1	0
Food Poisoning [description not available]	2.06	1	0
Venous Insufficiency Impaired venous blood flow or venous return (venous stasis), usually caused by inadequate venous valves. Venous insufficiency often occurs in the legs, and is associated with EDEMA and sometimes with VENOUS STASIS ULCERS at the ankle.	2.06	1	0
Black Fever [description not available]	3.31	6	0
Leishmaniasis, Visceral A chronic disease caused by LEISHMANIA DONOVANI and transmitted by the bite of several sandflies of the genera Phlebotomus and Lutzomyia. It is commonly characterized by fever, chills, vomiting, anemia, hepatosplenomegaly, leukopenia, hypergammaglobulinemia, emaciation, and an earth-gray color of the skin. The disease is classified into three main types according to geographic distribution: Indian, Mediterranean (or infantile), and African.	3.31	6	0
Demineralization, Tooth [description not available]	2.08	1	0
Alveolar Bone Atrophy [description not available]	2.54	2	0
Maxillary Diseases Diseases involving the MAXILLA.	2.08	1	0
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.45	2	0
Cocaine Abuse [description not available]	2.01	1	0
Cocaine-Related Disorders Disorders related or resulting from use of cocaine.	2.01	1	0
Middle Ear Inflammation [description not available]	3.39	1	1
Otitis Media Inflammation of the MIDDLE EAR including the AUDITORY OSSICLES and the EUSTACHIAN TUBE.	3.39	1	1
Infections, Pseudomonas [description not available]	2.71	3	0
Pseudomonas Infections Infections with bacteria of the genus PSEUDOMONAS.	2.71	3	0
Gastric Ulcer [description not available]	3.97	13	0
Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	3.97	13	0
Plasmodium falciparum Malaria [description not available]	4.12	3	1
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	4.12	3	1
Weight Gain Increase in BODY WEIGHT over existing weight.	3.12	5	0
Cryptosporidium Infection [description not available]	4.64	6	1
Cryptosporidiosis Intestinal infection with organisms of the genus CRYPTOSPORIDIUM. It occurs in both animals and humans. Symptoms include severe DIARRHEA.	4.64	6	1
Leishmaniasis, American [description not available]	2.49	2	0
Leishmaniasis, Cutaneous An endemic disease that is characterized by the development of single or multiple localized lesions on exposed areas of skin that typically ulcerate. The disease has been divided into Old and New World forms. Old World leishmaniasis is separated into three distinct types according to epidemiology and clinical manifestations and is caused by species of the L. tropica and L. aethiopica complexes as well as by species of the L. major genus. New World leishmaniasis, also called American leishmaniasis, occurs in South and Central America and is caused by species of the L. mexicana or L. braziliensis complexes.	2.49	2	0
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.94	4	0
Pyrexia [description not available]	2.02	1	0
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	2.02	1	0
Hepatocellular Carcinoma [description not available]	4.1	14	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	4.1	14	0
Brucella Infection [description not available]	2.5	2	0
Brucellosis Infection caused by bacteria of the genus BRUCELLA mainly involving the MONONUCLEAR PHAGOCYTE SYSTEM. This condition is characterized by fever, weakness, malaise, and weight loss.	2.5	2	0
Vaginitis Inflammation of the vagina characterized by pain and a purulent discharge.	2.03	1	0
Encephalitis, Viral Inflammation of brain parenchymal tissue as a result of viral infection. Encephalitis may occur as primary or secondary manifestation of TOGAVIRIDAE INFECTIONS; HERPESVIRIDAE INFECTIONS; ADENOVIRIDAE INFECTIONS; FLAVIVIRIDAE INFECTIONS; BUNYAVIRIDAE INFECTIONS; PICORNAVIRIDAE INFECTIONS; PARAMYXOVIRIDAE INFECTIONS; ORTHOMYXOVIRIDAE INFECTIONS; RETROVIRIDAE INFECTIONS; and ARENAVIRIDAE INFECTIONS.	2.03	1	0
Rubeola [description not available]	2.03	1	0
Measles A highly contagious infectious disease caused by MORBILLIVIRUS, common among children but also seen in the nonimmune of any age, in which the virus enters the respiratory tract via droplet nuclei and multiplies in the epithelial cells, spreading throughout the MONONUCLEAR PHAGOCYTE SYSTEM.	2.03	1	0
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	4.28	18	0
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	4.06	14	0
Dementias, Transmissible [description not available]	2.03	1	0
Injury, Myocardial Reperfusion [description not available]	3.17	5	0
Acute Respiratory Distress Syndrome [description not available]	2.41	2	0
Respiratory Distress Syndrome A syndrome characterized by progressive life-threatening RESPIRATORY INSUFFICIENCY in the absence of known LUNG DISEASES, usually following a systemic insult such as surgery or major TRAUMA.	2.41	2	0
Poultry Diseases Diseases of birds which are raised as a source of meat or eggs for human consumption and are usually found in barnyards, hatcheries, etc. The concept is differentiated from BIRD DISEASES which is for diseases of birds not considered poultry and usually found in zoos, parks, and the wild.	1.96	1	0
Deficiency, Vitamin K [description not available]	1.96	1	0
Vitamin K Deficiency A nutritional condition produced by a deficiency of VITAMIN K in the diet, characterized by an increased tendency to hemorrhage (HEMORRHAGIC DISORDERS). Such bleeding episodes may be particularly severe in newborn infants. (From Cecil Textbook of Medicine, 19th ed, p1182)	1.96	1	0
Cocarcinogenesis The combination of two or more different factors in the production of cancer.	2.66	3	0
Granulomas [description not available]	1.98	1	0
Pleurisy INFLAMMATION of PLEURA, the lining of the LUNG. When PARIETAL PLEURA is involved, there is pleuritic CHEST PAIN.	1.98	1	0
Granuloma A relatively small nodular inflammatory lesion containing grouped mononuclear phagocytes, caused by infectious and noninfectious agents.	1.98	1	0
Cystadenoma A benign neoplasm derived from glandular epithelium, in which cystic accumulations of retained secretions are formed. In some instances, considerable portions of the neoplasm, or even the entire mass, may be cystic. (Stedman, 25th ed)	1.98	1	0
Adenoma, Chromophobe A benign tumor of the anterior pituitary in which the cells do not stain with acidic or basic dyes.	1.98	1	0
Constricted Pupil [description not available]	2.7	3	0
Miosis Pupillary constriction. This may result from congenital absence of the dilatator pupillary muscle, defective sympathetic innervation, or irritation of the CONJUNCTIVA or CORNEA.	2.7	3	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.42	2	0
Chemical Dependence [description not available]	1.99	1	0
Substance-Related Disorders Disorders related to substance use or abuse.	1.99	1	0
Dermatitis, Contact, Photoallergic [description not available]	2.4	2	0
Cadaver A dead body, usually a human body.	2.43	2	0
Gallstone Disease [description not available]	2	1	0
Cholelithiasis Presence or formation of GALLSTONES in the BILIARY TRACT, usually in the gallbladder (CHOLECYSTOLITHIASIS) or the common bile duct (CHOLEDOCHOLITHIASIS).	2	1	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	2.94	4	0
Bovine Diseases [description not available]	2.45	2	0
Arthritis, Degenerative [description not available]	5.21	4	3
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	5.21	4	3
Angiogenesis, Pathologic [description not available]	3.88	12	0
Cytomegalic Inclusion Disease [description not available]	2.01	1	0
Cytomegalovirus Infections Infection with CYTOMEGALOVIRUS, characterized by enlarged cells bearing intranuclear inclusions. Infection may be in almost any organ, but the salivary glands are the most common site in children, as are the lungs in adults.	2.01	1	0
Gastric Diseases [description not available]	2.69	3	0
Hematochezia The passage of bright red blood from the rectum. The blood may or may not be mixed with formed stool in the form of blood, blood clots, bloody stool or diarrhea.	5.53	3	2
Gastrointestinal Hemorrhage Bleeding in any segment of the GASTROINTESTINAL TRACT from ESOPHAGUS to RECTUM.	5.53	3	2
Sarcoma, Epithelioid [description not available]	2.41	2	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	2.41	2	0
Leucocythaemia [description not available]	5.59	6	1
Dysmyelopoietic Syndromes [description not available]	3.36	1	1
Aphthae [description not available]	4.33	2	2
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	5.59	6	1
Myelodysplastic Syndromes Clonal hematopoietic stem cell disorders characterized by dysplasia in one or more hematopoietic cell lineages. They predominantly affect patients over 60, are considered preleukemic conditions, and have high probability of transformation into ACUTE MYELOID LEUKEMIA.	3.36	1	1
Stomatitis, Aphthous A recurrent disease of the oral mucosa of unknown etiology. It is characterized by small white ulcerative lesions, single or multiple, round or oval. Two to eight crops of lesions occur per year, lasting for 7 to 14 days and then heal without scarring. (From Jablonski's Dictionary of Dentistry, 1992, p742)	4.33	2	2
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.93	4	0
Arthropathies [description not available]	4.34	2	2
Joint Diseases Diseases involving the JOINTS.	4.34	2	2
Glaucoma, Suspect [description not available]	2.71	3	0
Intraocular Pressure The pressure of the fluids in the eye.	8.37	15	2
Ocular Hypertension A condition in which the intraocular pressure is elevated above normal and which may lead to glaucoma.	2.71	3	0
Adverse Drug Event [description not available]	2.31	1	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.31	1	0
Grippe [description not available]	2.41	1	0
Lupus Erythematosus, Cutaneous, Subacute [description not available]	2.41	1	0
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	2.41	1	0
Lupus Erythematosus, Cutaneous A form of lupus erythematosus in which the skin may be the only organ involved or in which skin involvement precedes the spread into other body systems. It has been classified into three forms - acute (= LUPUS ERYTHEMATOSUS, SYSTEMIC with skin lesions), subacute, and chronic (= LUPUS ERYTHEMATOSUS, DISCOID).	2.41	1	0
Chronic Kidney Failure [description not available]	6.34	7	2
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	6.34	7	2
Post-Natal Depression [description not available]	16.61	60	15
Depression, Postpartum Depression in POSTPARTUM WOMEN, usually within four weeks after giving birth (PARTURITION). The degree of depression ranges from mild transient depression to neurotic or psychotic depressive disorders. (From DSM-IV, p386)	16.61	60	15
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	4.64	5	1
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.77	3	0
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	2.77	3	0
Bone Loss, Osteoclastic [description not available]	2.55	2	0
Polyarthritis [description not available]	3.69	3	0
Arthritis Acute or chronic inflammation of JOINTS.	3.69	3	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.41	1	0
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.41	1	0
Vitiligo A disorder consisting of areas of macular depigmentation, commonly on extensor aspects of extremities, on the face or neck, and in skin folds. Age of onset is often in young adulthood and the condition tends to progress gradually with lesions enlarging and extending until a quiescent state is reached.	2.41	1	0
Aura [description not available]	3.44	7	0
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	3.44	7	0
Injuries, Spinal Cord [description not available]	2.96	3	0
Spinal Cord Injuries Penetrating and non-penetrating injuries to the spinal cord resulting from traumatic external forces (e.g., WOUNDS, GUNSHOT; WHIPLASH INJURIES; etc.).	2.96	3	0
Cystic Echinococcosis [description not available]	4	10	0
Osteomyelitis INFLAMMATION of the bone as a result of infection. It may be caused by a variety of infectious agents, especially pyogenic (PUS - producing) BACTERIA.	3.52	4	0
Sarcoma 180 An experimental sarcoma of mice.	3.38	5	0
Diabetes Insipidus and Mellitus with Optic Atrophy and Deafness [description not available]	3.33	1	0
Wolfram Syndrome A hereditary condition characterized by multiple symptoms including those of DIABETES INSIPIDUS; DIABETES MELLITUS; OPTIC ATROPHY; and DEAFNESS. This syndrome is also known as DIDMOAD (first letter of each word) and is usually associated with VASOPRESSIN deficiency. It is caused by mutations in gene WFS1 encoding wolframin, a 100-kDa transmembrane protein.	3.33	1	0
Canine Diseases [description not available]	3.91	2	1
Chronic Insomnia [description not available]	3.14	1	0
Sleep Initiation and Maintenance Disorders Disorders characterized by impairment of the ability to initiate or maintain sleep. This may occur as a primary disorder or in association with another medical or psychiatric condition.	3.14	1	0
Dermatoses [description not available]	2.6	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.6	1	0
Lesion of Sciatic Nerve [description not available]	2.21	1	0
Astrocytosis [description not available]	2.21	1	0
Nerve Pain [description not available]	2.21	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.21	1	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.55	2	0
Anoxia-Ischemia, Brain [description not available]	4.18	3	1
Hypoxia-Ischemia, Brain A disorder characterized by a reduction of oxygen in the blood combined with reduced blood flow (ISCHEMIA) to the brain from a localized obstruction of a cerebral artery or from systemic hypoperfusion. Prolonged hypoxia-ischemia is associated with ISCHEMIC ATTACK, TRANSIENT; BRAIN INFARCTION; BRAIN EDEMA; COMA; and other conditions.	4.18	3	1
Refractory Depression [description not available]	3.86	3	0
Depressive Disorder, Treatment-Resistant Failure to respond to two or more trials of antidepressant monotherapy or failure to respond to four or more trials of different antidepressant therapies. (Campbell's Psychiatric Dictionary, 9th ed.)	3.86	3	0
Infections, Staphylococcal [description not available]	3.03	4	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	3.03	4	0
Absence Seizure [description not available]	2.47	2	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	2.47	2	0
Infections, Rhabdoviridae [description not available]	2.25	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	5.15	5	0
C gattii Infection [description not available]	2.44	2	0
Cryptococcosis Fungal infection caused by genus CRYPTOCOCCUS.	2.44	2	0
Hypothermia, Accidental [description not available]	2.25	1	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.25	1	0
Osteogenic Sarcoma [description not available]	2.73	3	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	2.73	3	0
Candidiasis, Cutaneous Candidiasis of the skin manifested as eczema-like lesions of the interdigital spaces, perleche, or chronic paronychia. (Dorland, 27th ed)	2.25	1	0
Nociceptive Pain Dull or sharp aching pain caused by stimulated NOCICEPTORS due to tissue injury, inflammation or diseases. It can be divided into somatic or tissue pain and VISCERAL PAIN.	2.25	1	0
Cognitive Decline [description not available]	2.25	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	2.25	1	0
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	3.55	2	0
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	3.55	2	0
Consciousness, Loss of [description not available]	3.33	1	0
Keratoconus A noninflammatory, usually bilateral protrusion of the cornea, the apex being displaced downward and nasally. It occurs most commonly in females at about puberty. The cause is unknown but hereditary factors may play a role. The -conus refers to the cone shape of the corneal protrusion. (From Dorland, 27th ed)	2.31	1	0
Infections, Pneumococcal [description not available]	2.31	1	0
Pneumococcal Infections Infections with bacteria of the species STREPTOCOCCUS PNEUMONIAE.	2.31	1	0
Chronic Kidney Diseases [description not available]	2.31	1	0
Uremia A clinical syndrome associated with the retention of renal waste products or uremic toxins in the blood. It is usually the result of RENAL INSUFFICIENCY. Most uremic toxins are end products of protein or nitrogen CATABOLISM, such as UREA or CREATININE. Severe uremia can lead to multiple organ dysfunctions with a constellation of symptoms.	2.31	1	0
Renal Insufficiency, Chronic Conditions in which the KIDNEYS perform below the normal level for more than three months. Chronic kidney insufficiency is classified by five stages according to the decline in GLOMERULAR FILTRATION RATE and the degree of kidney damage (as measured by the level of PROTEINURIA). The most severe form is the end-stage renal disease (CHRONIC KIDNEY FAILURE). (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002)	2.31	1	0
Bradyarrhythmia [description not available]	2.45	2	0
Bradycardia Cardiac arrhythmias that are characterized by excessively slow HEART RATE, usually below 50 beats per minute in human adults. They can be classified broadly into SINOATRIAL NODE dysfunction and ATRIOVENTRICULAR BLOCK.	2.45	2	0
Experimental Hepatoma [description not available]	2.31	1	0
Algodystrophic Syndrome [description not available]	2.31	1	0
Reflex Sympathetic Dystrophy A syndrome characterized by severe burning pain in an extremity accompanied by sudomotor, vasomotor, and trophic changes in bone without an associated specific nerve injury. This condition is most often precipitated by trauma to soft tissue or nerve complexes. The skin over the affected region is usually erythematous and demonstrates hypersensitivity to tactile stimuli and erythema. (Adams et al., Principles of Neurology, 6th ed, p1360; Pain 1995 Oct;63(1):127-33)	2.31	1	0
Affective Psychosis, Bipolar [description not available]	3.23	1	0
Depression, Endogenous [description not available]	3.35	2	0
Bipolar Disorder A major affective disorder marked by severe mood swings (manic or major depressive episodes) and a tendency to remission and recurrence.	3.23	1	0
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	3.35	2	0
Bone Loss, Perimenopausal [description not available]	2.31	1	0
Osteoporosis, Postmenopausal Metabolic disorder associated with fractures of the femoral neck, vertebrae, and distal forearm. It occurs commonly in women within 15-20 years after menopause, and is caused by factors associated with menopause including estrogen deficiency.	2.31	1	0
Cardiac Failure [description not available]	2.45	2	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.45	2	0
Barrett Epithelium [description not available]	2.31	1	0
Esophageal Reflux [description not available]	2.31	1	0
Barrett Esophagus A condition with damage to the lining of the lower ESOPHAGUS resulting from chronic acid reflux (ESOPHAGITIS, REFLUX). Through the process of metaplasia, the squamous cells are replaced by a columnar epithelium with cells resembling those of the INTESTINE or the salmon-pink mucosa of the STOMACH. Barrett's columnar epithelium is a marker for severe reflux and precursor to ADENOCARCINOMA of the esophagus.	2.31	1	0
Gastroesophageal Reflux Retrograde flow of gastric juice (GASTRIC ACID) and/or duodenal contents (BILE ACIDS; PANCREATIC JUICE) into the distal ESOPHAGUS, commonly due to incompetence of the LOWER ESOPHAGEAL SPHINCTER.	2.31	1	0
Diffuse Parenchymal Lung Disease [description not available]	2.53	2	0
Cystic Fibrosis of Pancreas [description not available]	2.78	3	0
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	2.78	3	0
Lung Diseases, Interstitial A diverse group of lung diseases that affect the lung parenchyma. They are characterized by an initial inflammation of PULMONARY ALVEOLI that extends to the interstitium and beyond leading to diffuse PULMONARY FIBROSIS. Interstitial lung diseases are classified by their etiology (known or unknown causes), and radiological-pathological features.	2.53	2	0
Infections, Respirovirus [description not available]	2.15	1	0
Corneal Dystrophies [description not available]	2.15	1	0
Hepato-Pulmonary Syndrome [description not available]	2.15	1	0
Hepatopulmonary Syndrome A syndrome characterized by the clinical triad of advanced chronic liver disease, pulmonary vascular dilatations, and reduced arterial oxygenation (HYPOXEMIA) in the absence of intrinsic cardiopulmonary disease. This syndrome is common in the patients with LIVER CIRRHOSIS or portal hypertension (HYPERTENSION, PORTAL).	2.15	1	0
Bowel Diseases, Inflammatory [description not available]	2.76	3	0
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	2.76	3	0
Surgical Incision [description not available]	2.15	1	0
Age-Related Macular Degeneration [description not available]	2.84	3	0
Actinic Reticuloid Syndrome [description not available]	2.15	1	0
Macular Degeneration Degenerative changes in the RETINA usually of older adults which results in a loss of vision in the center of the visual field (the MACULA LUTEA) because of damage to the retina. It occurs in dry and wet forms.	2.84	3	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.17	1	0
Amyotrophic Lateral Sclerosis A degenerative disorder affecting upper MOTOR NEURONS in the brain and lower motor neurons in the brain stem and SPINAL CORD. Disease onset is usually after the age of 50 and the process is usually fatal within 3 to 6 years. Clinical manifestations include progressive weakness, atrophy, FASCICULATION, hyperreflexia, DYSARTHRIA, dysphagia, and eventual paralysis of respiratory function. Pathologic features include the replacement of motor neurons with fibrous ASTROCYTES and atrophy of anterior SPINAL NERVE ROOTS and corticospinal tracts. (From Adams et al., Principles of Neurology, 6th ed, pp1089-94)	2.17	1	0
Viral Diseases [description not available]	2.17	1	0
Virus Diseases A general term for diseases caused by viruses.	2.17	1	0
Equine Diseases [description not available]	2.17	1	0
Hepatitis B Virus Infection [description not available]	2.52	2	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	2.52	2	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	2.17	1	0
Rotavirus Infections Infection with any of the rotaviruses. Specific infections include human infantile diarrhea, neonatal calf diarrhea, and epidemic diarrhea of infant mice.	2.17	1	0
Parasite Infections [description not available]	2.17	1	0
Glucose Metabolic Disorder [description not available]	2.17	1	0
Liver Steatosis [description not available]	2.17	1	0
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.17	1	0
Edema-Proteinuria-Hypertension Gestosis [description not available]	2.52	2	0
Pre-Eclampsia A complication of PREGNANCY, characterized by a complex of symptoms including maternal HYPERTENSION and PROTEINURIA with or without pathological EDEMA. Symptoms may range between mild and severe. Pre-eclampsia usually occurs after the 20th week of gestation, but may develop before this time in the presence of trophoblastic disease.	2.52	2	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.52	2	0
Aspergillus Infection [description not available]	2.55	2	0
Eye Infections, Fungal Infection by a variety of fungi, usually through four possible mechanisms: superficial infection producing conjunctivitis, keratitis, or lacrimal obstruction; extension of infection from neighboring structures - skin, paranasal sinuses, nasopharynx; direct introduction during surgery or accidental penetrating trauma; or via the blood or lymphatic routes in patients with underlying mycoses.	2.17	1	0
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	2.55	2	0
Keratitis Inflammation of the cornea.	2.17	1	0
Recrudescence [description not available]	2.48	2	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	2.17	1	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	2.17	1	0
Atherosclerotic Parkinsonism [description not available]	2.21	1	0
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	2.21	1	0
Libman-Sacks Disease [description not available]	2.17	1	0
Lupus Erythematosus, Systemic A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.	2.17	1	0
Affective Disorders [description not available]	2.21	1	0
Mood Disorders Those disorders that have a disturbance in mood as their predominant feature.	2.21	1	0
Koch's Disease [description not available]	2.49	2	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.49	2	0
Behavior Disorders [description not available]	3.12	1	0
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	3.12	1	0
Choked Disk [description not available]	2.21	1	0
Episcleritis [description not available]	2.21	1	0
Ocular Infections [description not available]	2.21	1	0
Papilledema Swelling of the OPTIC DISK, usually in association with increased intracranial pressure, characterized by hyperemia, blurring of the disk margins, microhemorrhages, blind spot enlargement, and engorgement of retinal veins. Chronic papilledema may cause OPTIC ATROPHY and visual loss. (Miller et al., Clinical Neuro-Ophthalmology, 4th ed, p175)	2.21	1	0
Uveitis Inflammation of part or all of the uvea, the middle (vascular) tunic of the eye, and commonly involving the other tunics (sclera and cornea, and the retina). (Dorland, 27th ed)	2.81	3	0
Scleritis Refers to any inflammation of the sclera including episcleritis, a benign condition affecting only the episclera, which is generally short-lived and easily treated. Classic scleritis, on the other hand, affects deeper tissue and is characterized by higher rates of visual acuity loss and even mortality, particularly in necrotizing form. Its characteristic symptom is severe and general head pain. Scleritis has also been associated with systemic collagen disease. Etiology is unknown but is thought to involve a local immune response. Treatment is difficult and includes administration of anti-inflammatory and immunosuppressive agents such as corticosteroids. Inflammation of the sclera may also be secondary to inflammation of adjacent tissues, such as the conjunctiva.	2.21	1	0
Eye Infections Infection, moderate to severe, caused by bacteria, fungi, or viruses, which occurs either on the external surface of the eye or intraocularly with probable inflammation, visual impairment, or blindness.	2.21	1	0
Impaired Glucose Tolerance [description not available]	2.21	1	0
Compensatory Hyperinsulinemia A GLUCOSE-induced HYPERINSULINEMIA, a marker of insulin-resistant state. It is a mechanism to compensate for reduced sensitivity to insulin.	2.21	1	0
Hyperinsulinism A syndrome with excessively high INSULIN levels in the BLOOD. It may cause HYPOGLYCEMIA. Etiology of hyperinsulinism varies, including hypersecretion of a beta cell tumor (INSULINOMA); autoantibodies against insulin (INSULIN ANTIBODIES); defective insulin receptor (INSULIN RESISTANCE); or overuse of exogenous insulin or HYPOGLYCEMIC AGENTS.	2.21	1	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.21	1	0
Complications, Labor [description not available]	2.21	1	0
Menstruation, Painful [description not available]	3.4	2	0
Dysmenorrhea Painful menstruation.	3.4	2	0
Adenomyosis The extension of endometrial tissue (ENDOMETRIUM) into the MYOMETRIUM. It usually occurs in women in their reproductive years and may result in a diffusely enlarged uterus with ectopic and benign endometrial glands and stroma.	2.08	1	0
Arrhythmia [description not available]	5.84	4	2
Electrocardiogram QT Prolonged [description not available]	4.39	1	1
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	5.84	4	2
Long QT Syndrome A condition that is characterized by episodes of fainting (SYNCOPE) and varying degree of ventricular arrhythmia as indicated by the prolonged QT interval. The inherited forms are caused by mutation of genes encoding cardiac ion channel proteins. The two major forms are ROMANO-WARD SYNDROME and JERVELL-LANGE NIELSEN SYNDROME.	4.39	1	1
Acute Pain Intensely discomforting, distressful, or agonizing sensation associated with trauma or disease, with well-defined location, character, and timing.	5.67	3	2
Cold Sore [description not available]	3.47	1	1
Herpes Labialis Herpes simplex, caused by type 1 virus, primarily spread by oral secretions and usually occurring as a concomitant of fever. It may also develop in the absence of fever or prior illness. It commonly involves the facial region, especially the lips and the nares. (Dorland, 27th ed.)	3.47	1	1
Kahler Disease [description not available]	3	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	3	1	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.08	1	0
Anal Fissure [description not available]	2.08	1	0
Fissure in Ano A painful linear tear at the margin of the anus. It appears as a crack or slit in the mucous membrane of the anus and is very painful and difficult to heal.	2.08	1	0
Bacterial Vaginitides [description not available]	2.08	1	0
Bacterial Infections, Gram-Positive [description not available]	2.08	1	0
Vaginosis, Bacterial Polymicrobial, nonspecific vaginitis associated with positive cultures of Gardnerella vaginalis and other anaerobic organisms and a decrease in lactobacilli. It remains unclear whether the initial pathogenic event is caused by the growth of anaerobes or a primary decrease in lactobacilli.	2.08	1	0
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	2.08	1	0
Acute Post-operative Pain [description not available]	7.67	9	7
Pain, Postoperative Pain during the period after surgery.	7.67	9	7
Orphan Diseases Rare diseases that have not been well studied.	3.01	1	0
Neglected Diseases Diseases that are underfunded and have low name recognition but are major burdens in less developed countries. The World Health Organization has designated six tropical infectious diseases as being neglected in industrialized countries that are endemic in many developing countries (HELMINTHIASIS; LEPROSY; LYMPHATIC FILARIASIS; ONCHOCERCIASIS; SCHISTOSOMIASIS; and TRACHOMA).	3.01	1	0
Rheumatoid Arthritis [description not available]	4.65	3	2
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	4.65	3	2
Moniliasis, Oral [description not available]	2.1	1	0
Candidiasis, Oral Infection of the mucous membranes of the mouth by a fungus of the genus CANDIDA. (Dorland, 27th ed)	2.1	1	0
Lysosomal Enzyme Disorders [description not available]	2.1	1	0
Organophosphorus Poisoning [description not available]	2.1	1	0
Organophosphate Poisoning Poisoning due to exposure to ORGANOPHOSPHORUS COMPOUNDS, such as ORGANOPHOSPHATES; ORGANOTHIOPHOSPHATES; and ORGANOTHIOPHOSPHONATES.	2.1	1	0
Alopecia Cicatrisata [description not available]	2.11	1	0
Alopecia Absence of hair from areas where it is normally present.	2.11	1	0
Dementia Praecox [description not available]	2.46	2	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.46	2	0
Choroid Neovascularization [description not available]	2.48	2	0
Impotence [description not available]	3.51	1	1
Erectile Dysfunction The inability in the male to have a PENILE ERECTION due to psychological or organ dysfunction.	3.51	1	1
Infections, Prosthesis-Related [description not available]	2.49	2	0
Cherry Red Spot Myoclonus Syndrome [description not available]	2.1	1	0
Devic Disease [description not available]	2.1	1	0
Neuromyelitis Optica A syndrome characterized by acute OPTIC NEURITIS; MYELITIS, TRANSVERSE; demyelinating and/or necrotizing lesions in the OPTIC NERVES and SPINAL CORD; and presence of specific autoantibodies to AQUAPORIN 4.	2.1	1	0
Brain Hemorrhage, Cerebral [description not available]	2.42	2	0
Cerebral Hemorrhage Bleeding into one or both CEREBRAL HEMISPHERES including the BASAL GANGLIA and the CEREBRAL CORTEX. It is often associated with HYPERTENSION and CRANIOCEREBRAL TRAUMA.	2.42	2	0
Central Retinal Edema, Cystoid [description not available]	5.08	3	1
Cyclitis, Chronic [description not available]	2.1	1	0
Macular Edema Fluid accumulation in the outer layer of the MACULA LUTEA that results from intraocular or systemic insults. It may develop in a diffuse pattern where the macula appears thickened or it may acquire the characteristic petaloid appearance referred to as cystoid macular edema. Although macular edema may be associated with various underlying conditions, it is most commonly seen following intraocular surgery, venous occlusive disease, DIABETIC RETINOPATHY, and posterior segment inflammatory disease. (From Survey of Ophthalmology 2004; 49(5) 470-90)	5.08	3	1
Uveitis, Posterior Inflammation of the choroid as well as the retina and vitreous body. Some form of visual disturbance is usually present. The most important characteristics of posterior uveitis are vitreous opacities, choroiditis, and chorioretinitis.	2.1	1	0
Uveitis, Intermediate Inflammation of the pars plana, ciliary body, and adjacent structures.	2.1	1	0
Iris Diseases Diseases, dysfunctions, or disorders of or located in the iris.	2.11	1	0
Sterility, Female [description not available]	2.1	1	0
Infertility, Female Diminished or absent ability of a female to achieve conception.	2.1	1	0
Cerebral Ischemia [description not available]	2.49	2	0
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.49	2	0
Lymphoma, Primary Effusion A rare neoplasm of large B-cells usually presenting as serious effusions without detectable tumor masses. The most common sites of involvement are the pleural, pericardial, and peritoneal cavities. It is associated with HUMAN HERPESVIRUS 8, most often occurring in the setting of immunodeficiency.	2.1	1	0
Apoplexy [description not available]	3.4	2	0
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	3.4	2	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.11	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.11	1	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	2.11	1	0
Eczema, Atopic [description not available]	2.83	3	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.83	3	0
Angiospasm, Intracranial [description not available]	2.11	1	0
Vasospasm, Intracranial Constriction of arteries in the SKULL due to sudden, sharp, and often persistent smooth muscle contraction in blood vessels. Intracranial vasospasm results in reduced vessel lumen caliber, restricted blood flow to the brain, and BRAIN ISCHEMIA that may lead to hypoxic-ischemic brain injury (HYPOXIA-ISCHEMIA, BRAIN).	2.11	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2.11	1	0
Infections, Orthomyxoviridae [description not available]	2.76	3	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	2.76	3	0
Ataxia Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.	5.38	7	0
Liver Dysfunction [description not available]	7.8	11	1
Liver Diseases Pathological processes of the LIVER.	7.8	11	1
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.11	1	0
Bed Sores [description not available]	2.78	3	0
Pressure Ulcer An ulceration caused by prolonged pressure on the SKIN and TISSUES when one stays in one position for a long period of time, such as lying in bed. The bony areas of the body are the most frequently affected sites which become ischemic (ISCHEMIA) under sustained and constant pressure.	2.78	3	0
Eye Disorders [description not available]	2.76	3	0
Eye Diseases Diseases affecting the eye.	2.76	3	0
Deafness, Transitory [description not available]	2.49	2	0
Hearing Loss A general term for the complete or partial loss of the ability to hear from one or both ears.	2.49	2	0
Toxoplasmosis, Animal Acquired infection of non-human animals by organisms of the genus TOXOPLASMA.	2.11	1	0
Granulocytic Leukemia [description not available]	2.11	1	0
Leukemia, Myeloid Form of leukemia characterized by an uncontrolled proliferation of the myeloid lineage and their precursors (MYELOID PROGENITOR CELLS) in the bone marrow and other sites.	2.11	1	0
Autoimmune Thrombocytopenia [description not available]	2.13	1	0
Purpura, Thrombocytopenic, Idiopathic Thrombocytopenia occurring in the absence of toxic exposure or a disease associated with decreased platelets. It is mediated by immune mechanisms, in most cases IMMUNOGLOBULIN G autoantibodies which attach to platelets and subsequently undergo destruction by macrophages. The disease is seen in acute (affecting children) and chronic (adult) forms.	2.13	1	0
Pemphigus Foliaceus [description not available]	2.11	1	0
Pemphigus Group of chronic blistering diseases characterized histologically by ACANTHOLYSIS and blister formation within the EPIDERMIS.	2.11	1	0
Cardiac Remodeling, Ventricular [description not available]	2.49	2	0
Heart Disease, Ischemic [description not available]	2.11	1	0
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2.11	1	0
Bladder Cancer [description not available]	2.48	2	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.48	2	0
Asthma, Bronchial [description not available]	2.49	2	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	2.49	2	0
Granulocytic Leukemia, Chronic [description not available]	2.73	3	0
Acute Myelogenous Leukemia [description not available]	2.49	2	0
Leukemia, Myelogenous, Chronic, BCR-ABL Positive Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.	2.73	3	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.49	2	0
Colitis Gravis [description not available]	2.49	2	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.49	2	0
Dyslipidemia [description not available]	2.13	1	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	2.13	1	0
Infections, Spirochaetales [description not available]	2.13	1	0
Stomatitis, Denture Inflammation of the mouth due to denture irritation.	2.13	1	0
Disease Exacerbation [description not available]	3.7	3	0
Nerve Degeneration Loss of functional activity and trophic degeneration of nerve axons and their terminal arborizations following the destruction of their cells of origin or interruption of their continuity with these cells. The pathology is characteristic of neurodegenerative diseases. Often the process of nerve degeneration is studied in research on neuroanatomical localization and correlation of the neurophysiology of neural pathways.	2.76	3	0
Diathesis [description not available]	2.13	1	0
Cochlear Hearing Loss [description not available]	2.13	1	0
Hearing Loss, Sensorineural Hearing loss resulting from damage to the COCHLEA and the sensorineural elements which lie internally beyond the oval and round windows. These elements include the AUDITORY NERVE and its connections in the BRAINSTEM.	2.13	1	0
Leishmania Infection [description not available]	2.13	1	0
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	2.13	1	0
Carcinoma, Squamous Cell of Head and Neck [description not available]	2.13	1	0
Cancer of Head [description not available]	2.73	3	0
Cancer of Mouth [description not available]	2.73	3	0
Squamous Cell Carcinoma of Head and Neck The most common type of head and neck carcinoma that originates from cells on the surface of the NASAL CAVITY; MOUTH; PARANASAL SINUSES, SALIVARY GLANDS, and LARYNX. Mutations in TNFRSF10B, PTEN, and ING1 genes are associated with this cancer.	2.13	1	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.73	3	0
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.73	3	0
7-Dehydrocholesterol Reductase Deficiency [description not available]	2.47	2	0
Smith-Lemli-Opitz Syndrome An autosomal recessive disorder of CHOLESTEROL metabolism. It is caused by a deficiency of 7-dehydrocholesterol reductase, the enzyme that converts 7-dehydrocholesterol to cholesterol, leading to an abnormally low plasma cholesterol. This syndrome is characterized by multiple CONGENITAL ABNORMALITIES, growth deficiency, and INTELLECTUAL DISABILITY.	2.47	2	0
Acute Kidney Failure [description not available]	2.44	2	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	2.44	2	0
Infections, Vibrio [description not available]	2.13	1	0
Acetyl-CoA:alpha-Glucosaminide N-Acetyltransferase Deficiency [description not available]	2.15	1	0
Mucopolysaccharidosis III Mucopolysaccharidosis characterized by heparitin sulfate in the urine, progressive mental retardation, mild dwarfism, and other skeletal disorders. There are four clinically indistinguishable but biochemically distinct forms, each due to a deficiency of a different enzyme.	2.15	1	0
Breast Cancer, Male [description not available]	2.13	1	0
Breast Neoplasms, Male Any neoplasms of the male breast. These occur infrequently in males in developed countries, the incidence being about 1% of that in females.	2.13	1	0
Adhesions, Tissue [description not available]	2.13	1	0
Hematologic Malignancies [description not available]	2.13	1	0
Disseminated Fungal Infection [description not available]	2.13	1	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.13	1	0
Classical Niemann-Pick Disease [description not available]	2.13	1	0
Niemann-Pick Disease, Type A The classic infantile form of Niemann-Pick Disease, caused by mutation in SPHINGOMYELIN PHOSPHODIESTERASE. It is characterized by accumulation of SPHINGOMYELINS in the cells of the MONONUCLEAR PHAGOCYTE SYSTEM and other cell throughout the body leading to cell death. Clinical signs include JAUNDICE, hepatosplenomegaly, and severe brain damage.	2.13	1	0
Central Nervous System Disease [description not available]	2.13	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	2.13	1	0
Nasal Bleeding [description not available]	2.13	1	0
Hereditary Hemorrhagic Telangiectasia [description not available]	2.13	1	0
Epistaxis Bleeding from the nose.	2.13	1	0
Telangiectasia, Hereditary Hemorrhagic An autosomal dominant vascular anomaly characterized by telangiectases of the skin and mucous membranes and by recurrent gastrointestinal bleeding. This disorder is caused by mutations of a gene (on chromosome 9q3) which encodes endoglin, a membrane glycoprotein that binds TRANSFORMING GROWTH FACTOR BETA.	2.13	1	0
Infections, Plasmodium [description not available]	2.51	2	0
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.51	2	0
B. burgdorferi Infection [description not available]	2.15	1	0
Lyme Disease An infectious disease caused by a spirochete, BORRELIA BURGDORFERI, which is transmitted chiefly by Ixodes dammini (see IXODES) and pacificus ticks in the United States and Ixodes ricinis (see IXODES) in Europe. It is a disease with early and late cutaneous manifestations plus involvement of the nervous system, heart, eye, and joints in variable combinations. The disease was formerly known as Lyme arthritis and first discovered at Old Lyme, Connecticut.	2.15	1	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	2.15	1	0
Nephrosis Pathological processes of the KIDNEY without inflammatory or neoplastic components. Nephrosis may be a primary disorder or secondary complication of other diseases. It is characterized by the NEPHROTIC SYNDROME indicating the presence of PROTEINURIA and HYPOALBUMINEMIA with accompanying EDEMA.	2.15	1	0
Neuroendocrine Tumors Tumors whose cells possess secretory granules and originate from the neuroectoderm, i.e., the cells of the ectoblast or epiblast that program the neuroendocrine system. Common properties across most neuroendocrine tumors include ectopic hormone production (often via APUD CELLS), the presence of tumor-associated antigens, and isozyme composition.	2.15	1	0
Glaucoma An ocular disease, occurring in many forms, having as its primary characteristics an unstable or a sustained increase in the intraocular pressure which the eye cannot withstand without damage to its structure or impairment of its function. The consequences of the increased pressure may be manifested in a variety of symptoms, depending upon type and severity, such as excavation of the optic disk, hardness of the eyeball, corneal anesthesia, reduced visual acuity, seeing of colored halos around lights, disturbed dark adaptation, visual field defects, and headaches. (Dictionary of Visual Science, 4th ed)	3.87	4	0
Dermatitis, Contact, Phototoxic [description not available]	2.04	1	0
Low Back Ache [description not available]	3.43	1	1
Low Back Pain Acute or chronic pain in the lumbar or sacral regions, which may be associated with musculo-ligamentous SPRAINS AND STRAINS; INTERVERTEBRAL DISK DISPLACEMENT; and other conditions.	3.43	1	1
Hydrophobia [description not available]	2.05	1	0
Keratitis, Ulcerative [description not available]	2.45	2	0
Bacterial Eye Infections [description not available]	2.45	2	0
Corneal Ulcer Loss of epithelial tissue from the surface of the cornea due to progressive erosion and necrosis of the tissue; usually caused by bacterial, fungal, or viral infection.	2.45	2	0
Blood Pressure, Low [description not available]	2.05	1	0
Hypotension Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.	2.05	1	0
Adult GM1 Gangliosidosis [description not available]	2.74	3	0
Gangliosidosis, GM1 An autosomal recessive neurodegenerative disorder caused by the absence or deficiency of BETA-GALACTOSIDASE. It is characterized by intralysosomal accumulation of G(M1) GANGLIOSIDE and oligosaccharides, primarily in neurons of the central nervous system. The infantile form is characterized by MUSCLE HYPOTONIA, poor psychomotor development, HIRSUTISM, hepatosplenomegaly, and facial abnormalities. The juvenile form features HYPERACUSIS; SEIZURES; and psychomotor retardation. The adult form features progressive DEMENTIA; ATAXIA; and MUSCLE SPASTICITY. (From Menkes, Textbook of Child Neurology, 5th ed, pp96-7)	2.74	3	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.05	1	0
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.05	1	0
Bordetella Infections Infections with bacteria of the genus BORDETELLA.	2.45	2	0
Neovascularization, Optic Disc [description not available]	2.05	1	0
Retinal Neovascularization Formation of new blood vessels originating from the retinal veins and extending along the inner (vitreal) surface of the retina.	2.05	1	0
Addison Disease and Cerebral Sclerosis [description not available]	2.05	1	0
Adrenoleukodystrophy An X-linked recessive disorder characterized by the accumulation of saturated very long chain fatty acids in the LYSOSOMES of ADRENAL CORTEX and the white matter of CENTRAL NERVOUS SYSTEM. This disease occurs almost exclusively in the males. Clinical features include the childhood onset of ATAXIA; NEUROBEHAVIORAL MANIFESTATIONS; HYPERPIGMENTATION; ADRENAL INSUFFICIENCY; SEIZURES; MUSCLE SPASTICITY; and DEMENTIA. The slowly progressive adult form is called adrenomyeloneuropathy. The defective gene ABCD1 is located at Xq28, and encodes the adrenoleukodystrophy protein (ATP-BINDING CASSETTE TRANSPORTERS).	2.05	1	0
Staphylococcal Pneumonia [description not available]	2.05	1	0
Pneumonia, Staphylococcal Pneumonia caused by infections with bacteria of the genus STAPHYLOCOCCUS, usually with STAPHYLOCOCCUS AUREUS.	2.05	1	0
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.46	2	0
Postherpetic Neuralgia [description not available]	2.05	1	0
Neuralgia, Postherpetic Pain in nerves, frequently involving facial SKIN, resulting from the activation the latent varicella-zoster virus (HERPESVIRUS 3, HUMAN). The two forms of the condition preceding the pain are HERPES ZOSTER OTICUS; and HERPES ZOSTER OPHTHALMICUS. Following the healing of the rashes and blisters, the pain sometimes persists.	2.05	1	0
Acquired Metabolic Diseases, Brain [description not available]	2.05	1	0
Pain, Intractable Persistent pain that is refractory to some or all forms of treatment.	2.05	1	0
Abnormalities, Autosome [description not available]	2.05	1	0
B Virus Infection [description not available]	2.05	1	0
Cystitis Inflammation of the URINARY BLADDER, either from bacterial or non-bacterial causes. Cystitis is usually associated with painful urination (dysuria), increased frequency, urgency, and suprapubic pain.	2.05	1	0
Infection, Wound [description not available]	2.05	1	0
Disease, Pulmonary [description not available]	2.44	2	0
Lung Diseases Pathological processes involving any part of the LUNG.	2.44	2	0
Sinus Infections [description not available]	3.44	1	1
Sinusitis Inflammation of the NASAL MUCOSA in one or more of the PARANASAL SINUSES.	3.44	1	1
Bronchiolitis, Exudative [description not available]	2.05	1	0
Bronchiolitis Obliterans Inflammation of the BRONCHIOLES leading to an obstructive lung disease. Bronchioles are characterized by fibrous granulation tissue with bronchial exudates in the lumens. Clinical features include a nonproductive cough and DYSPNEA.	2.05	1	0
Akinetic-Rigid Variant of Huntington Disease [description not available]	2.47	2	0
Huntington Disease A familial disorder inherited as an autosomal dominant trait and characterized by the onset of progressive CHOREA and DEMENTIA in the fourth or fifth decade of life. Common initial manifestations include paranoia; poor impulse control; DEPRESSION; HALLUCINATIONS; and DELUSIONS. Eventually intellectual impairment; loss of fine motor control; ATHETOSIS; and diffuse chorea involving axial and limb musculature develops, leading to a vegetative state within 10-15 years of disease onset. The juvenile variant has a more fulminant course including SEIZURES; ATAXIA; dementia; and chorea. (From Adams et al., Principles of Neurology, 6th ed, pp1060-4)	2.47	2	0
Asystole [description not available]	2.42	2	0
Shock, Cardiogenic Shock resulting from diminution of cardiac output in heart disease.	2.06	1	0
Apnea A transient absence of spontaneous respiration.	2.06	1	0
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	2.42	2	0
Prosthesis Durability [description not available]	2.06	1	0
Corneal Angiogenesis [description not available]	2.41	2	0
Corneal Neovascularization New blood vessels originating from the corneal blood vessels and extending from the limbus into the adjacent CORNEAL STROMA. Neovascularization in the superficial and/or deep corneal stroma is a sequel to numerous inflammatory diseases of the ocular anterior segment, such as TRACHOMA, viral interstitial KERATITIS, microbial KERATOCONJUNCTIVITIS, and the immune response elicited by CORNEAL TRANSPLANTATION.	2.41	2	0
Addiction, Opioid [description not available]	2.05	1	0
Opioid-Related Disorders Disorders related to or resulting from abuse or misuse of OPIOIDS.	2.05	1	0
Abnormalities, Drug-Induced Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.	2.05	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.73	3	0
Coronary Artery Stenosis [description not available]	2.05	1	0
Coronary Stenosis Narrowing or constriction of a coronary artery.	2.05	1	0
Mastitis, Bovine INFLAMMATION of the UDDER in cows.	2.06	1	0
Burns, Chemical Burns caused by contact with or exposure to CAUSTICS or strong ACIDS.	2.06	1	0
Eye Burns Injury to any part of the eye by extreme heat, chemical agents, or ultraviolet radiation.	2.06	1	0
Thromboembolism Obstruction of a blood vessel (embolism) by a blood clot (THROMBUS) in the blood stream.	2.06	1	0
American Trypanosomiasis [description not available]	2.06	1	0
Chagas Disease Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.	2.06	1	0
Bancroftian Elephantiasis [description not available]	2.06	1	0
Elephantiasis, Filarial Parasitic infestation of the human lymphatic system by WUCHERERIA BANCROFTI or BRUGIA MALAYI. It is also called lymphatic filariasis.	2.06	1	0
Onchocerciasis Infection with nematodes of the genus ONCHOCERCA. Characteristics include the presence of firm subcutaneous nodules filled with adult worms, PRURITUS, and ocular lesions.	2.06	1	0
Heritable Pulmonary Arterial Hypertension [description not available]	2.06	1	0
Pulmonary Hypertension [description not available]	2.06	1	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	2.06	1	0
Familial Primary Pulmonary Hypertension Familial or idiopathic hypertension in the PULMONARY CIRCULATION which is not secondary to other disease.	2.06	1	0
ADPKD [description not available]	2.06	1	0
Polycystic Kidney, Autosomal Dominant Kidney disorders with autosomal dominant inheritance and characterized by multiple CYSTS in both KIDNEYS with progressive deterioration of renal function.	2.06	1	0
Antibiotic-Associated Colitis [description not available]	2.06	1	0
Enterocolitis, Pseudomembranous An acute inflammation of the INTESTINAL MUCOSA that is characterized by the presence of pseudomembranes or plaques in the SMALL INTESTINE (pseudomembranous enteritis) and the LARGE INTESTINE (pseudomembranous colitis). It is commonly associated with antibiotic therapy and CLOSTRIDIUM DIFFICILE colonization.	2.06	1	0
Diabetic Retinopathy Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.	4.37	1	1
Enterovirus Infections Diseases caused by ENTEROVIRUS.	2.06	1	0
Uveitis, Anterior Inflammation of the anterior uvea comprising the iris, angle structures, and the ciliary body. Manifestations of this disorder include ciliary injection, exudation into the anterior chamber, iris changes, and adhesions between the iris and lens (posterior synechiae). Intraocular pressure may be increased or reduced.	4.75	2	1
Diseases in Twins Disorders affecting TWINS, one or both, at any age.	2.06	1	0
Kidney Stones [description not available]	2.07	1	0
Kidney Calculi Stones in the KIDNEY, usually formed in the urine-collecting area of the kidney (KIDNEY PELVIS). Their sizes vary and most contains CALCIUM OXALATE.	2.07	1	0
Mouth Diseases Diseases involving the MOUTH.	3.81	2	1
Group A Strep Infection [description not available]	2.46	2	0
Streptococcal Infections Infections with bacteria of the genus STREPTOCOCCUS.	2.46	2	0
Fish Diseases Diseases of freshwater, marine, hatchery or aquarium fish. This term includes diseases of both teleosts (true fish) and elasmobranchs (sharks, rays and skates).	2.07	1	0
DNA Virus Infections Diseases caused by DNA VIRUSES.	2.07	1	0
Blue-Eared Pig Disease [description not available]	2.06	1	0
Cancer of Pituitary [description not available]	2.45	2	0
Pituitary Neoplasms Neoplasms which arise from or metastasize to the PITUITARY GLAND. The majority of pituitary neoplasms are adenomas, which are divided into non-secreting and secreting forms. Hormone producing forms are further classified by the type of hormone they secrete. Pituitary adenomas may also be characterized by their staining properties (see ADENOMA, BASOPHIL; ADENOMA, ACIDOPHIL; and ADENOMA, CHROMOPHOBE). Pituitary tumors may compress adjacent structures, including the HYPOTHALAMUS, several CRANIAL NERVES, and the OPTIC CHIASM. Chiasmal compression may result in bitemporal HEMIANOPSIA.	2.45	2	0
Anterior Cerebral Circulation Infarction [description not available]	2.07	1	0
Brain Infarction Tissue NECROSIS in any area of the brain, including the CEREBRAL HEMISPHERES, the CEREBELLUM, and the BRAIN STEM. Brain infarction is the result of a cascade of events initiated by inadequate blood flow through the brain that is followed by HYPOXIA and HYPOGLYCEMIA in brain tissue. Damage may be temporary, permanent, selective or pan-necrosis.	2.07	1	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.07	1	0
Newcastle Disease An acute febrile, contagious, viral disease of birds caused by an AVULAVIRUS called NEWCASTLE DISEASE VIRUS. It is characterized by respiratory and nervous symptoms in fowl and is transmissible to man causing a severe, but transient conjunctivitis.	2.07	1	0
Histoplasma capsulatum Infection [description not available]	2.07	1	0
Histoplasmosis Infection resulting from exposure to the fungus HISTOPLASMA. It is worldwide in distribution and particularly common in the central and eastern states, especially areas around the Ohio and Mississippi River valleys.	2.07	1	0
Allergy, Food [description not available]	2.07	1	0
Food Hypersensitivity Gastrointestinal disturbances, skin eruptions, or shock due to allergic reactions to allergens in food.	2.07	1	0
Dermatitis, Irritant A non-allergic contact dermatitis caused by prolonged exposure to irritants and not explained by delayed hypersensitivity mechanisms.	3.46	1	1
Adult Periodontitis [description not available]	2.07	1	0
Low Bone Density [description not available]	2.07	1	0
Bone Diseases, Metabolic Diseases that affect the METABOLIC PROCESSES of BONE TISSUE.	2.07	1	0
Benign Mastocytoma [description not available]	2.07	1	0
Acute Brain Injuries [description not available]	2.45	2	0
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.45	2	0
Bilirubinemia [description not available]	2.07	1	0
Clinically Isolated CNS Demyelinating Syndrome [description not available]	2.07	1	0
Age-Related Memory Disorders [description not available]	2.07	1	0
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	2.07	1	0
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.07	1	0
Di Guglielmo Disease [description not available]	2.08	1	0
Leukemia, Megakaryocytic [description not available]	2.08	1	0
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.08	1	0
Leukemia, Megakaryoblastic, Acute An acute myeloid leukemia in which 20-30% of the bone marrow or peripheral blood cells are of megakaryocyte lineage. MYELOFIBROSIS or increased bone marrow RETICULIN is common.	2.08	1	0
Myeloproliferative Disorders Conditions which cause proliferation of hemopoietically active tissue or of tissue which has embryonic hemopoietic potential. They all involve dysregulation of multipotent MYELOID PROGENITOR CELLS, most often caused by a mutation in the JAK2 PROTEIN TYROSINE KINASE.	2.08	1	0
Injury, Ischemia-Reperfusion [description not available]	2.08	1	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.08	1	0
Orthopedic Disorders [description not available]	3	1	0
Musculoskeletal Diseases Diseases of the muscles and their associated ligaments and other connective tissue and of the bones and cartilage viewed collectively.	3	1	0
Coronary Thrombosis Coagulation of blood in any of the CORONARY VESSELS. The presence of a blood clot (THROMBUS) often leads to MYOCARDIAL INFARCTION.	2.01	1	0
B-Cell Lymphoma [description not available]	2.01	1	0
Lymphoma, B-Cell A group of heterogeneous lymphoid tumors generally expressing one or more B-cell antigens or representing malignant transformations of B-lymphocytes.	2.01	1	0
Back Ache [description not available]	3.39	1	1
Back Pain Acute or chronic pain located in the posterior regions of the THORAX; LUMBOSACRAL REGION; or the adjacent regions.	3.39	1	1
A-alphalipoprotein Neuropathy [description not available]	2.01	1	0
Vaginal Diseases Pathological processes of the VAGINA.	3.4	1	1
E chaffeensis Infection [description not available]	2.01	1	0
African Lymphoma [description not available]	2.01	1	0
Burkitt Lymphoma A form of undifferentiated malignant LYMPHOMA usually found in central Africa, but also reported in other parts of the world. It is commonly manifested as a large osteolytic lesion in the jaw or as an abdominal mass. B-cell antigens are expressed on the immature cells that make up the tumor in virtually all cases of Burkitt lymphoma. The Epstein-Barr virus (HERPESVIRUS 4, HUMAN) has been isolated from Burkitt lymphoma cases in Africa and it is implicated as the causative agent in these cases; however, most non-African cases are EBV-negative.	2.01	1	0
Palsy [description not available]	2.02	1	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	2.02	1	0
Basophilic Leukemia, Acute [description not available]	2.02	1	0
Leukemia, Basophilic, Acute A rare acute myeloid leukemia in which the primary differentiation is to BASOPHILS. It is characterized by an extreme increase of immature basophilic granulated cells in the bone marrow and blood. Mature basophils are usually sparse.	2.02	1	0
Infections, Listeria [description not available]	2.02	1	0
Cataract, Membranous [description not available]	2.71	3	0
Cataract Partial or complete opacity on or in the lens or capsule of one or both eyes, impairing vision or causing blindness. The many kinds of cataract are classified by their morphology (size, shape, location) or etiology (cause and time of occurrence). (Dorland, 27th ed)	2.71	3	0
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2.91	4	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	2.02	1	0
Angor Pectoris [description not available]	2.39	2	0
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	2.39	2	0
Hemorrhagic Shock [description not available]	2.02	1	0
Atopic Hypersensitivity [description not available]	2.02	1	0
Drug Withdrawal Symptoms [description not available]	2.02	1	0
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	2.02	1	0
Endotoxin Shock [description not available]	2.02	1	0
Shock, Septic Sepsis associated with HYPOTENSION or hypoperfusion despite adequate fluid resuscitation. Perfusion abnormalities may include but are not limited to LACTIC ACIDOSIS; OLIGURIA; or acute alteration in mental status.	2.02	1	0
Complication, Postoperative [description not available]	4.33	1	1
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	4.33	1	1
B-Cell Chronic Lymphocytic Leukemia [description not available]	2.03	1	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	2.03	1	0
Acquired Nephrogenic Diabetes Insipidus [description not available]	2.03	1	0
Infections, Picornaviridae [description not available]	2.03	1	0
Acute Lymphoid Leukemia [description not available]	2.03	1	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	2.03	1	0
Encephalitis, Polio [description not available]	2.03	1	0
Poliomyelitis An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)	2.03	1	0
Encephalopathy, Toxic [description not available]	2.44	2	0
Acrania [description not available]	2.03	1	0
Neural Tube Defects Congenital malformations of the central nervous system and adjacent structures related to defective neural tube closure during the first trimester of pregnancy generally occurring between days 18-29 of gestation. Ectodermal and mesodermal malformations (mainly involving the skull and vertebrae) may occur as a result of defects of neural tube closure. (From Joynt, Clinical Neurology, 1992, Ch55, pp31-41)	2.03	1	0
Emesis [description not available]	2.03	1	0
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	2.03	1	0
Respiratory Syndrome, Acute, Severe [description not available]	2.03	1	0
Severe Acute Respiratory Syndrome A viral disorder characterized by high FEVER, dry COUGH, shortness of breath (DYSPNEA) or breathing difficulties, and atypical PNEUMONIA. A virus in the genus CORONAVIRUS is the suspected agent.	2.03	1	0
Cholangiocellular Carcinoma [description not available]	2.03	1	0
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	2.03	1	0
Polyomavirus Infections Infections with POLYOMAVIRUS, which are often cultured from the urine of kidney transplant patients. Excretion of BK VIRUS is associated with ureteral strictures and CYSTITIS, and that of JC VIRUS with progressive multifocal leukoencephalopathy (LEUKOENCEPHALOPATHY, PROGRESSIVE MULTIFOCAL).	2.03	1	0
Nephritis Inflammation of any part of the KIDNEY.	2.03	1	0
Disc, Herniated [description not available]	2.03	1	0
Intervertebral Disc Displacement An INTERVERTEBRAL DISC in which the NUCLEUS PULPOSUS has protruded through surrounding ANNULUS FIBROSUS. This occurs most frequently in the lower lumbar region.	2.03	1	0
Corneal Edema An excessive amount of fluid in the cornea due to damage of the epithelium or endothelium causing decreased visual acuity.	2.03	1	0
Tachyarrhythmia [description not available]	2.04	1	0
Tachycardia Abnormally rapid heartbeat, usually with a HEART RATE above 100 beats per minute for adults. Tachycardia accompanied by disturbance in the cardiac depolarization (cardiac arrhythmia) is called tachyarrhythmia.	2.04	1	0
MS (Multiple Sclerosis) [description not available]	2.04	1	0
Multiple Sclerosis An autoimmune disorder mainly affecting young adults and characterized by destruction of myelin in the central nervous system. Pathologic findings include multiple sharply demarcated areas of demyelination throughout the white matter of the central nervous system. Clinical manifestations include visual loss, extra-ocular movement disorders, paresthesias, loss of sensation, weakness, dysarthria, spasticity, ataxia, and bladder dysfunction. The usual pattern is one of recurrent attacks followed by partial recovery (see MULTIPLE SCLEROSIS, RELAPSING-REMITTING), but acute fulminating and chronic progressive forms (see MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVE) also occur. (Adams et al., Principles of Neurology, 6th ed, p903)	2.04	1	0
Blastomyces brasiliensis Infection [description not available]	2.04	1	0
AIDS, Simian [description not available]	2.04	1	0
Cholera Infantum [description not available]	4.69	2	1
Rheumatism [description not available]	3.77	2	0
Rheumatic Diseases Disorders of connective tissue, especially the joints and related structures, characterized by inflammation, degeneration, or metabolic derangement.	3.77	2	0
Left Ventricular Dysfunction [description not available]	3.37	1	1
Ventricular Dysfunction, Left A condition in which the LEFT VENTRICLE of the heart was functionally impaired. This condition usually leads to HEART FAILURE; MYOCARDIAL INFARCTION; and other cardiovascular complications. Diagnosis is made by measuring the diminished ejection fraction and a depressed level of motility of the left ventricular wall.	3.37	1	1
Hypervitaminosis A A symptom complex resulting from ingesting excessive amounts of VITAMIN A.	2.67	3	0
Indigestion [description not available]	3.37	1	1
Infections, Helicobacter [description not available]	3.37	1	1
Dyspepsia Impaired digestion, especially after eating.	3.37	1	1
Helicobacter Infections Infections with organisms of the genus HELICOBACTER, particularly, in humans, HELICOBACTER PYLORI. The clinical manifestations are focused in the stomach, usually the gastric mucosa and antrum, and the upper duodenum. This infection plays a major role in the pathogenesis of type B gastritis and peptic ulcer disease.	3.37	1	1
Constriction, Pathological [description not available]	2.38	2	0
Apolipoprotein B-100, Familial Defective [description not available]	1.98	1	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	2.38	2	0
Hyperlipoproteinemia Type II A group of familial disorders characterized by elevated circulating cholesterol contained in either LOW-DENSITY LIPOPROTEINS alone or also in VERY-LOW-DENSITY LIPOPROTEINS (pre-beta lipoproteins).	1.98	1	0
Germinoblastoma [description not available]	1.98	1	0
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	1.98	1	0
Circulatory Collapse [description not available]	1.98	1	0
Shock A pathological condition manifested by failure to perfuse or oxygenate vital organs.	1.98	1	0
Vascular Diseases Pathological processes involving any of the BLOOD VESSELS in the cardiac or peripheral circulation. They include diseases of ARTERIES; VEINS; and rest of the vasculature system in the body.	1.98	1	0
Arrhythmia, Sinoatrial [description not available]	1.99	1	0
A-V Dissociation [description not available]	1.99	1	0
Foreign-Body Reaction Chronic inflammation and granuloma formation around irritating foreign bodies.	1.99	1	0
Experimental Leukemia [description not available]	1.99	1	0
Infections, Retroviridae [description not available]	1.99	1	0
Fibroma, Shope [description not available]	1.99	1	0
Retroviridae Infections Virus diseases caused by the RETROVIRIDAE.	1.99	1	0
Enlarged Spleen [description not available]	1.99	1	0
Absence Status [description not available]	1.99	1	0
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	1.99	1	0
Lichen Planus, Oral Oral lesions accompanying cutaneous lichen planus or often occurring alone. The buccal mucosa, lips, gingivae, floor of the mouth, and palate are usually affected (in a descending order of frequency). Typically, oral lesions consist of radiating white or gray, velvety, threadlike lines, arranged in a reticular pattern, at the intersection of which there may be minute, white, elevated dots or streaks (Wickham's striae). (Jablonski, Illustrated Dictionary of Dentistry)	3.38	1	1
Muscle Disorders [description not available]	2	1	0
Muscular Diseases Acquired, familial, and congenital disorders of SKELETAL MUSCLE and SMOOTH MUSCLE.	2	1	0
Neutropenia A decrease in the number of NEUTROPHILS found in the blood.	3.38	1	1
Biliary Fistula Abnormal passage in any organ of the biliary tract or between biliary organs and other organs.	2	1	0
Marchiafava-Micheli Syndrome [description not available]	2	1	0
Hemoglobinuria, Paroxysmal A condition characterized by the recurrence of HEMOGLOBINURIA caused by intravascular HEMOLYSIS. In cases occurring upon cold exposure (paroxysmal cold hemoglobinuria), usually after infections, there is a circulating antibody which is also a cold hemolysin. In cases occurring during or after sleep (paroxysmal nocturnal hemoglobinuria), the clonal hematopoietic stem cells exhibit a global deficiency of cell membrane proteins.	2	1	0
Aortic Diseases Pathological processes involving any part of the AORTA.	2	1	0
Action Tremor [description not available]	2	1	0
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	2	1	0
Anochlesia [description not available]	1.98	1	0
Hypergonadotropic Hypogonadism [description not available]	1.97	1	0
Hypogonadism Condition resulting from deficient gonadal functions, such as GAMETOGENESIS and the production of GONADAL STEROID HORMONES. It is characterized by delay in GROWTH, germ cell maturation, and development of secondary sex characteristics. Hypogonadism can be due to a deficiency of GONADOTROPINS (hypogonadotropic hypogonadism) or due to primary gonadal failure (hypergonadotropic hypogonadism).	1.97	1	0
Lymphocytosis Excess of normal lymphocytes in the blood or in any effusion.	1.97	1	0
Bordetella pertussis Infection, Respiratory [description not available]	2.37	2	0
Whooping Cough A respiratory infection caused by BORDETELLA PERTUSSIS and characterized by paroxysmal coughing ending in a prolonged crowing intake of breath.	2.37	2	0
EHS Tumor [description not available]	1.97	1	0

betadex

Description

Cross-References

Synonyms (113)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (3 Product(s))

Product Categories

Products

Drug Classes (1)

Protein Targets (26)

Potency Measurements

Activation Measurements

Bioassays (79)

Research

Studies (8,586)

Study Types

Clinical Trials (12)

Trial Overview

betadex

Description

Cross-References

Synonyms (113)

Research Excerpts

Toxicity

Pharmacokinetics

Compound-Compound Interactions

Bioavailability

Dosage Studied

Occurs in Manufacturing (3 Product(s))

Product Categories

Products

Drug Classes (1)

Protein Targets (26)

Potency Measurements

Activation Measurements

Bioassays (79)

Research

Studies (8,586)

Study Types

Clinical Trials (12)

Trial Overview

Related Drugs (2,903)

Related Conditions (821)