adamantane profile

Adamantane is a tricyclic organic compound with the formula C10H16. It is a colorless, crystalline solid with a camphor-like odor. Adamantane is a saturated hydrocarbon, meaning that it contains only carbon and hydrogen atoms and has no double or triple bonds. It is a very stable molecule, due to its cage-like structure. Adamantane was first isolated from petroleum in 1932. It can be synthesized from cyclohexane by a series of reactions, including chlorination, dehydrochlorination, and hydrogenation. Adamantane has been studied extensively due to its unique properties, including its high melting point, chemical inertness, and ability to form stable derivatives. It has potential applications in the fields of medicine, materials science, and nanotechnology. For example, adamantane derivatives have been investigated as antiviral agents, anti-inflammatory drugs, and catalysts. Adamantane has also been used to modify the properties of polymers, such as increasing their hardness and thermal stability. The study of adamantane continues to be an active area of research, with the goal of developing new and improved applications for this versatile molecule.'

Adamantane: A tricyclo bridged hydrocarbon. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	9238
CHEMBL ID	1230831
CHEBI ID	40519
MeSH ID	M0000336

Synonym
CHEMBL1230831
adamantine
tricyclo[3.3.1.13,7]decane
nsc-527913
nsc527913
tricyclo[3.3.1.1(3,7)]decane
inchi=1/c10h16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10h,1-6h
tricyclo[3.3.1.1~3,7~]decane
281-23-2
adamantane
adamantan
CHEBI:40519 ,
DB03627
adamantane, >=99%
tricyclo(3.3.1.13,7)decane
nsc 527913
einecs 206-001-4
A0696
AKOS000119960
AKOS004908007
ec 206-001-4
unii-pjy633525u
pjy633525u ,
A819332
tricyclo[3.3.1.1]decane
FT-0621893
AKOS016354066
adamantane [mi]
tricyclo(3,3,1,1,<3,7>)-decane
tricyclo[3.3.1.1<3,7>]decane
W-107075
A3233
DTXSID5022017
mfcd00074719
F0001-0891
adamantane; >99%
DS-4960
AS-12242
Q351461
S2869
AMY793
a 0696; nsc 527913
adamantane; tricyclo[3.3.1.1(3),?]decane
D88553
adamantane tricyclo[3.3.1.1]decane
HY-N2427
CS-0022641
EN300-19684
adamantane (purified by sublimation)
Z104474730

Excerpt	Reference	Relevance
"Adamantane is a common pharmacophore for drug design, and myrtenal (M) demonstrated neuroprotective effects in our previous studies."	( New Myrtenal-Adamantane Conjugates Alleviate Alzheimer's-Type Dementia in Rat Model. Alexandrova, A; Bibi, A; Dragomanova, S; Georgieva, A; Kalfin, R; Lazarova, M; Munkuev, A; Reynisson, J; Salakhutdinov, N; Stefanova, M; Suslov, E; Tancheva, L; Tzvetanova, E; Uzunova, D; Volcho, K, 2022)	1.81
"As adamantane is a common structural feature in several 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors, we have explored the ability of the 6,7,8,9,10,11-hexahydro-5H-5,9:7,11-dimethanobenzo[9]annulen-7-yl scaffold to act as a surrogate of the adamantane nucleus in a novel series of 11β-HSD1 inhibitors."	( Searching for novel applications of the benzohomoadamantane scaffold in medicinal chemistry: Synthesis of novel 11β-HSD1 inhibitors. Bidon-Chanal, A; Binnie, M; Luque, FJ; McBride, A; Seira, C; Valverde, E; Vázquez, S; Webster, SP, 2015)	1.19
"The adamantanes are a class of compounds that have found use in the treatment of influenza A and Parkinson's disease, among others. "	( Distribution and dynamics of adamantanes in a lipid bilayer. Biggin, PC; Chew, CF; Guy, A, 2008)	1.2
"Adamantane is a spherical top molecule with tetrahedral symmetry (T(d) point group) and has no permanent dipole moment in its vibronic ground state."	( Rotationally resolved infrared spectroscopy of adamantane. Boudon, V; Oomens, J; Pirali, O; Vervloet, M, 2012)	1.36
"Adamantane diazirine is a hydrophobic photoactivated probe that partitions into the cell membrane and can be used to identify regions of proteins that are embedded within the membrane."	( Identification of hydrophobic regions of the calcium-transport ATPase from sarcoplasmic reticulum after photochemical labeling with adamantane diazirine. Farley, RA, 1983)	1.19

Excerpt	Reference	Relevance
"Adamantane ring has been reported to exhibit significant inhibitory potential towards P2X receptors, especially for P2X7R."	( Design and synthesis of adamantane-1-carbonyl thiourea derivatives as potent and selective inhibitors of h-P2X4 and h-P2X7 receptors: An Emerging therapeutic tool for treatment of inflammation and neurological disorders. Ali Shah, SJ; Iqbal, J; Mahmood, A, 2022)	1.75
"Adamantane has been widely used as a "lipophilic bullet" in drug discovery and development, due to its unique diamond-like architecture with benign pharmacological/ pharmaceutical properties. "	( Synthesis and biological evaluation of platensic alcohol as an adamantane surrogate in antitumor drug lead adaphostin. Duan, Y; Huang, Y; Wen, Z; Xiong, Y, 2021)	2.3
"The adamantane derivatives have been used in HCV clinical trials, but large variation in drug efficacy among the various HCV genotypes has been difficult to explain without detailed molecular structures."	( Unusual architecture of the p7 channel from hepatitis C virus. Berardi, MJ; Chou, JJ; Dev, J; OuYang, B; Sun, B; Xie, S; Yu, W; Zhao, X, 2013)	0.87
"Adamantanes have been used by chronic care facilities for influenza A prophylaxis; however, genotypic resistance has altered prophylaxis recommendations."	( Control of an outbreak due to an adamantane-resistant strain of influenza A (H3N2) in a chronic care facility. Cohen, NJ; Gerber, SI; Jones, RC; Morita, JY; Nawrocki, J; Plate, DK; Simon, MT; Siston, AM, 2008)	1.35
"Adamantane-derived drugs have been used for treatment and prophylaxis of influenza A virus infection for many years worldwide. "	( A comprehensive surveillance of adamantane resistance among human influenza A virus isolated from mainland China between 1956 and 2009. Dong, L; Gao, Y; Guo, J; Guo, Y; Huang, W; Jiang, T; Lan, Y; Li, X; Li, Z; Peng, Y; Shu, Y; Wang, D; Wang, M; Wang, W; Wen, L; Xin, L; Xu, C; Yang, L; Zhang, Y; Zhao, X, 2010)	2.09
"Adamantanes have been used to treat influenza A virus infections for many years. "	( Incidence of adamantane resistance among influenza A (H3N2) viruses isolated worldwide from 1994 to 2005: a cause for concern. Bright, RA; Cox, NJ; Davis, XM; Klimov, AI; Medina, MJ; Perez-Oronoz, G; Povinelli, L; Wallis, TR; Xu, X, 2005)	2.14

Excerpt	Reference	Relevance
"Rimantadine has been shown to be more active in vitro and less toxic than amantadine in adults with influenza A disease."	( Serum concentrations and safety of rimantadine in paediatric patients. Brady, MT; Nahata, MC, 1986)	0.27
" The plasma drug concentrations after the first dose correlated significantly with total symptom sources for both amantadine and rimantadine, but the plasma levels of toxic and nontoxic subjects overlapped extensively."	( Differences in side effects of amantadine hydrochloride and rimantadine hydrochloride relate to differences in pharmacokinetics. Hayden, FG; Hoffman, HE; Spyker, DA, 1983)	0.27
" In contrast, APD-induced Fos expression increases in the caudate-putamen (CPu) and prefrontal cortex (PFC) are associated with the extrapyramidal side effect liability of typical APDs or the effectiveness against negative symptoms of atypical APDs, respectively."	( Neurotensin receptor antagonist SR 142948A alters Fos expression and extrapyramidal side effect profile of typical and atypical antipsychotic drugs. Binder, EB; Kinkead, B; Nemeroff, CB; Owens, MJ, 2004)	0.32
" These data suggest that ethanol withdrawal can be created in HT22 cells in a manner that is more toxic than ethanol exposure and that ZYC26 is a more potent cytoprotectant than 17beta-estradiol against cell death and oxidative damage induced by ethanol withdrawal."	( A nonfeminizing estrogen analog protects against ethanol withdrawal toxicity in immortalized hippocampal cells. Jung, ME; Simpkins, JW; Wilson, AM, 2006)	0.33
" The combination therapy escaped these adverse effects."	( Combination of dipeptidylpeptidase IV inhibitor and low dose thiazolidinedione: preclinical efficacy and safety in db/db mice. Bansal, VS; Davis, JA; Dhar, A; Khanna, V; Mahajan, DC; Mittra, S; Priyadarsiny, P; Roy, S; Saini, KS; Sattigeri, J; Singh, S, 2007)	0.34
" Careful postmarketing surveillance for adverse effects, especially among the DPP4 inhibitors, and continued evaluation in longer-term studies and in clinical practice are required to determine the role of this new class among current pharmacotherapies for type 2 diabetes."	( Efficacy and safety of incretin therapy in type 2 diabetes: systematic review and meta-analysis. Amori, RE; Lau, J; Pittas, AG, 2007)	0.34
" One or more adverse event (AE) was reported by 82."	( Efficacy and safety of vildagliptin monotherapy during 2-year treatment of drug-naïve patients with type 2 diabetes: comparison with metformin. Calle Pascual, A; Dejager, S; Foley, J; Göke, B; Hershon, K; Kerr, D; Schweizer, A; Shao, Q, 2008)	0.35
" The incidence of adverse events (AEs), serious AEs and adjudicated cardiovascular events was 74."	( Fifty-two-week efficacy and safety of vildagliptin vs. glimepiride in patients with type 2 diabetes mellitus inadequately controlled on metformin monotherapy. Ahrén, B; Byiers, S; Dejager, S; Ferrannini, E; Fonseca, V; Matthews, D; Shao, Q; Zinman, B, 2009)	0.35
" More serious adverse events (SAEs) occurred in vildagliptin- than rosiglitazone-treated patients (12."	( Long-term 2-year safety and efficacy of vildagliptin compared with rosiglitazone in drug-naïve patients with type 2 diabetes mellitus. Maldonado-Lutomirsky, M; Niggli, M; Rosenstock, J, 2009)	0.35
" Incidence of hypoglycemic adverse events and weight reductions were similar to those with placebo."	( The efficacy and safety of saxagliptin when added to metformin therapy in patients with inadequately controlled type 2 diabetes with metformin alone. Chen, RS; DeFronzo, RA; Garber, AJ; Hissa, MN; Luiz Gross, J; Ravichandran, S; Yuyan Duan, R, 2009)	0.35
" DPP-4 inhibitors are safe and tolerable with no increased risk of adverse events compared to placebo and have a low risk of hypoglycaemia."	( Clinical results of treating type 2 diabetic patients with sitagliptin, vildagliptin or saxagliptin--diabetes control and potential adverse events. Ahrén, B, 2009)	0.35
" To assess potential neurologic adverse effects of oseltamivir use in infants, a retrospective chart review was performed in infants less than 12 months of age who received oseltamivir, amantadine, or rimantadine."	( Safety of oseltamivir compared with the adamantanes in children less than 12 months of age. Abughali, N; Abzug, MJ; Bradley, JS; Cloud, GA; Englund, J; Griffin, J; Guzman-Cottrill, J; Jacobs, RF; Jester, P; Kimberlin, DW; Lang, D; Leach, C; Ramilo, O; Robinson, J; Romero, JR; Shalabi, M; Shelton, M; Storch, G; Wade, KC; Whitley, RJ, 2010)	0.63
"The primary objective was to describe the frequency of neurologic adverse events among children less than 12 months of age who received oseltamivir compared with those receiving adamantanes."	( Safety of oseltamivir compared with the adamantanes in children less than 12 months of age. Abughali, N; Abzug, MJ; Bradley, JS; Cloud, GA; Englund, J; Griffin, J; Guzman-Cottrill, J; Jacobs, RF; Jester, P; Kimberlin, DW; Lang, D; Leach, C; Ramilo, O; Robinson, J; Romero, JR; Shalabi, M; Shelton, M; Storch, G; Wade, KC; Whitley, RJ, 2010)	0.82
" The overall incidence of any adverse events was similar in both groups (approximately 61%), but the number of serious adverse events was higher in the gliclazide group (8."	( A comparison of efficacy and safety of vildagliptin and gliclazide in combination with metformin in patients with Type 2 diabetes inadequately controlled with metformin alone: a 52-week, randomized study. Filozof, C; Gautier, JF, 2010)	0.36
" Overall adverse events (AEs) were lower in the vildagliptin-treated patients compared with that in the voglibose-treated patients (61."	( Efficacy and safety of vildagliptin and voglibose in Japanese patients with type 2 diabetes: a 12-week, randomized, double-blind, active-controlled study. Iwamoto, Y; Kashiwagi, A; Mimori, N; Suzuki, M; Tachibana, H; Terao, S; Yamada, N, 2010)	0.36
" Apart from significant subcutaneous swelling at the injection sites of most of the treated animals, no other treatment related adverse events occurred."	( Efficacy, safety and pharmacokinetics of 1,2,4-trioxolane OZ78 against an experimental infection with Fasciola hepatica in sheep. Dong, Y; Haschke, M; Huwyler, J; Kaminsky, R; Keiser, J; Kirchhofer, C; Malikides, N; Vanhoff, K; Vennerstrom, JL, 2010)	0.36
" Both treatments were generally well tolerated; incidence and types of adverse events were comparable between groups."	( Efficacy and safety of saxagliptin in combination with metformin compared with sitagliptin in combination with metformin in adult patients with type 2 diabetes mellitus. Charpentier, G; Gause-Nilsson, I; Hellqvist, A; Ostgren, CJ; Scheen, AJ, 2010)	0.36
" Adverse event rates were similar with saxagliptin 5 mg once-daily compared with placebo in older patients."	( Efficacy and safety of saxagliptin in older patients with type 2 diabetes mellitus. Chacra, A; Doucet, J; Harris, S; Lu, J; Maheux, P; Rosenstock, J, 2011)	0.37
" The aim of this paper is therefore to assess the general safety and tolerability, including incidences of the most common adverse events (AEs), of vildagliptin based on a large pooled database of Phase II and III clinical trials."	( Assessing the general safety and tolerability of vildagliptin: value of pooled analyses from a large safety database versus evaluation of individual studies. Dejager, S; Foley, JE; Kothny, W; Schweizer, A, 2011)	0.37
" Adverse event frequency was similar between groups."	( Safety and efficacy of saxagliptin added to thiazolidinedione over 76 weeks in patients with type 2 diabetes mellitus. Allen, E; Chen, R; Frederich, R; Hollander, PL; Li, J, 2011)	0.37
" Adverse event frequency was similar in all treatment groups; reported hypoglycaemia event rates were 24."	( Safety and efficacy of saxagliptin in combination with submaximal sulphonylurea versus up-titrated sulphonylurea over 76 weeks. Chacra, AR; Chen, R; List, J; Ravichandran, S; Tan, GH, 2011)	0.37
" Adverse events for the US cohort were consistent with previously reported data from the 3 trials."	( Efficacy and safety of saxagliptin combination therapy in US patients with type 2 diabetes. Allen, E; Chen, R; Donovan, M; Fleming, D; Karyekar, C; Ravichandran, S, 2011)	0.37
"5 or 5 mg as add-on therapy to OADs results in improvement across key glycemic parameters compared with placebo add-on and was generally safe and well tolerated."	( Efficacy and safety of saxagliptin combination therapy in US patients with type 2 diabetes. Allen, E; Chen, R; Donovan, M; Fleming, D; Karyekar, C; Ravichandran, S, 2011)	0.37
" The proportion of patients experiencing adverse events (excluding hypoglycemia) was similar for saxagliptin plus metformin (42."	( Efficacy and safety of saxagliptin added to metformin in Asian people with type 2 diabetes mellitus: a randomized controlled trial. Gause-Nilsson, I; Pan, CY; Tou, C; Yang, W; Zhao, J, 2011)	0.37
" Adverse events (AEs) and serious AEs (SAEs) were evaluated."	( Efficacy and safety of saxagliptin in drug-naïve Asian patients with type 2 diabetes mellitus: a randomized controlled trial. Gause-Nilsson, I; Pan, CY; Tou, C; Yang, W; Zhao, J, 2012)	0.38
" Meta-analyses were conducted for HbA1c, weight, fasting plasma glucose (FPG), hypoglycaemia and other adverse events."	( The efficacy and safety of vildagliptin in patients with type 2 diabetes: a meta-analysis of randomized clinical trials. Cai, L; Cai, Y; Liu, P; Lu, ZJ; Zhang, Y, 2012)	0.38
" In addition, compared to comparators, vildagliptin was not associated with an increase in overall risk for any adverse events [RR, 0·97 (95% CI, 0·94-0·99)]."	( The efficacy and safety of vildagliptin in patients with type 2 diabetes: a meta-analysis of randomized clinical trials. Cai, L; Cai, Y; Liu, P; Lu, ZJ; Zhang, Y, 2012)	0.38
"Vildagliptin is effective in glycaemic control with a low risk of hypoglycaemia and other adverse reactions."	( The efficacy and safety of vildagliptin in patients with type 2 diabetes: a meta-analysis of randomized clinical trials. Cai, L; Cai, Y; Liu, P; Lu, ZJ; Zhang, Y, 2012)	0.38
" In patients with moderate RI, similar proportions of patients experienced any adverse event (AE) (84 vs."	( One-year safety, tolerability and efficacy of vildagliptin in patients with type 2 diabetes and moderate or severe renal impairment. Groop, PH; Kothny, W; Lukashevich, V; Shao, Q, 2012)	0.38
" Treatment with saxagliptin is effective, generally safe and well tolerated, apart from a small increase in the incidence of infections such as nasopharyngitis."	( Saxagliptin overview: special focus on safety and adverse effects. Ali, S; Fonseca, V, 2013)	0.39
" The paper highlights in detail saxagliptin-associated adverse effects, drug interactions, its use in patients with renal and hepatic disease and long-term safety concerns."	( Saxagliptin overview: special focus on safety and adverse effects. Ali, S; Fonseca, V, 2013)	0.39
" It is generally safe and well tolerated; however, it requires dose adjustment in renal disease as well as when used with drugs that are strong inhibitor or inducer of CYP3A4/A5 isoforms."	( Saxagliptin overview: special focus on safety and adverse effects. Ali, S; Fonseca, V, 2013)	0.39
" Safety was assessed by adverse events, hypoglycemia, and body weight."	( Saxagliptin efficacy and safety in patients with type 2 diabetes mellitus and cardiovascular disease history or cardiovascular risk factors: results of a pooled analysis of phase 3 clinical trials. Allen, E; Bryzinski, B; Cook, W; Frederich, R; Slater, J, 2013)	0.39
" Saxagliptin was well tolerated, with similar adverse event rates and types compared with placebo."	( Saxagliptin efficacy and safety in patients with type 2 diabetes mellitus and cardiovascular disease history or cardiovascular risk factors: results of a pooled analysis of phase 3 clinical trials. Allen, E; Bryzinski, B; Cook, W; Frederich, R; Slater, J, 2013)	0.39
" Most adverse events were mild or moderate, with slightly greater frequency of upper respiratory infections with saxagliptin."	( Long-term 4-year safety of saxagliptin in drug-naive and metformin-treated patients with Type 2 diabetes. Aguilar-Salinas, C; Berglind, N; Fleming, D; Gross, JL; Hissa, M; Ravichandran, S; Rosenstock, J, 2013)	0.39
"Saxagliptin monotherapy or add-on to metformin is generally safe and well tolerated, with no increased risk of hypoglycaemia, for up to 4 years."	( Long-term 4-year safety of saxagliptin in drug-naive and metformin-treated patients with Type 2 diabetes. Aguilar-Salinas, C; Berglind, N; Fleming, D; Gross, JL; Hissa, M; Ravichandran, S; Rosenstock, J, 2013)	0.39
" During the 52-week study period, the proportion of patients reporting ≥1 adverse event (AE) was 66."	( Saxagliptin add-on therapy to insulin with or without metformin for type 2 diabetes mellitus: 52-week safety and efficacy. Barnett, AH; Charbonnel, B; Donovan, M; Fleming, D; Iqbal, N; Li, J, 2013)	0.39
"Teneligliptin is a novel DPP-4 inhibitor in development for treating type 2 diabetes mellitus that does not require dose adjustment for diabetic patients with end-stage renal disease; however, it had not been known whether or not teneligliptin is safe or potent in dialysis patients."	( Safety and efficacy of teneligliptin: a novel DPP-4 inhibitor for hemodialysis patients with type 2 diabetes. Kosaka, T; Kuwahara, Y; Nakamura, K; Otsuki, H; Shimomura, F; Tsukamoto, T, 2014)	0.4
" Safety and tolerability assessments included adverse events (AEs), hypoglycaemia and body weight."	( A randomized controlled trial of the efficacy and safety of saxagliptin as add-on therapy in patients with type 2 diabetes and inadequate glycaemic control on metformin plus a sulphonylurea. Brook, D; Fisher, SA; Kalra, S; Montanaro, M; Monyak, J; Moses, RG; Sockler, J; Visvanathan, J, 2014)	0.4
" Adverse events were generally mild and occurred at similar rates in both groups."	( Efficacy and safety of vildagliptin in new-onset diabetes after kidney transplantation--a randomized, double-blind, placebo-controlled trial. Antlanger, M; Döller, D; Haidinger, M; Hecking, M; Kopecky, C; Kovarik, JJ; Pacini, G; Pleiner, J; Säemann, MD; Stemer, G; Werzowa, J, 2014)	0.4
" Open-label design and under reporting of adverse events are limitations of this post hoc analysis."	( Real-life efficacy and safety of vildagliptin compared with sulfonylureas as add-on to metformin in patients with type 2 diabetes mellitus in Germany. Bader, G; Dworak, M; Göke, R; Gruenberger, JB, 2014)	0.4
" The rate of adverse events was comparable in both groups."	( [Efficacy and safety of vildagliptin as a second-line therapy vs other oral antidiabetic agents in patients with type 2 diabetes: Czech results within the worldwide prospective cohort EDGE study]. Brada, M; Dohnalová, L; Edelsberger, T; Gerle, J; Haluzík, M; Houdová, J; Veselá, V, 2013)	0.39
" Adverse events and events of special interest (gastrointestinal adverse events, infections, hypersensitivity, pancreatitis, skin lesions, lymphopenia, thrombocytopenia, hypoglycaemia, bone fracture, severe cutaneous adverse reactions, opportunistic infection, angioedema, malignancy, worsening renal function, and specific laboratory events) were assessed; incidence rates (events/100 person-years) and incidence rates ratios (saxagliptin/control) were calculated (Mantel-Haenszel method)."	( Safety of saxagliptin: events of special interest in 9156 patients with type 2 diabetes mellitus. Donovan, M; Edelberg, H; Hirshberg, B; Iqbal, N; Parker, A, 2014)	0.4
" Overall incidence of adverse events was similar among treatment groups."	( Efficacy and safety evaluation of HSD-1 inhibitor ABT-384 in Alzheimer's disease. Greco, N; Katz, DA; Lenz, RA; Liu, W; Marek, GJ; Meier, A; Zhang, W, 2014)	0.4
" Adjudicated major adverse CV events (MACE; CV death, myocardial infarction [MI], and stroke) and investigator-reported heart failure were assessed, and incidence rates (IRs; events/100 patient-years) and IR ratios (IRRs; saxagliptin/control) were calculated (Mantel-Haenszel method)."	( Assessment of the cardiovascular safety of saxagliptin in patients with type 2 diabetes mellitus: pooled analysis of 20 clinical trials. Donovan, M; Frederich, R; Hirshberg, B; Iqbal, N; Parker, A, 2014)	0.4
"This review considers the pharmacokinetic profile, adverse effects and drug interactions of DPP-4 inhibitors."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" However, DPP-4 inhibitors have certain differences in their pharmacokinetic properties that may be associated with different clinical effects and adverse event profiles."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" Glycosylated hemoglobin (HbA1c) values, fasting and postprandial blood glucose (FBG and P2BG), body weight, body mass index (BMI), episodes of hypoglycemia and adverse events were evaluated."	( Efficacy and safety comparison of add-on therapy with liraglutide, saxagliptin and vildagliptin, all in combination with current conventional oral hypoglycemic agents therapy in poorly controlled Chinese type 2 diabetes. Ding, M; Li, CJ; Liu, XJ; Yu, DM; Yu, P; Yu, Q; Zhang, QM, 2014)	0.4
"5 and 5mg and placebo, the proportion of patients with ≥1 adverse event (AE) was 78."	( Saxagliptin efficacy and safety in patients with type 2 diabetes receiving concomitant statin therapy. Allen, E; Bryzinski, B; Cook, W; Hirshberg, B, )	0.13
"Treatment decisions for older patients with type 2 diabetes mellitus must balance glycemic control and adverse event risk."	( Long-term safety and tolerability of saxagliptin add-on therapy in older patients (aged ≥ 65 years) with type 2 diabetes. Allen, E; Iqbal, N; Öhman, P, 2014)	0.4
"Pooled adverse event data from three placebo-controlled trials of 76-206 weeks' duration in older (≥ 65 years) and younger (<65 years) patients receiving saxagliptin 5 mg or matching placebo added to metformin, glyburide, or a thiazolidinedione were analyzed."	( Long-term safety and tolerability of saxagliptin add-on therapy in older patients (aged ≥ 65 years) with type 2 diabetes. Allen, E; Iqbal, N; Öhman, P, 2014)	0.4
" Adverse events (AE) and hypoglycemia were monitored."	( Saxagliptin efficacy and safety in patients with type 2 diabetes mellitus stratified by cardiovascular disease history and cardiovascular risk factors: analysis of 3 clinical trials. Bryzinski, B; Cook, W; Hirshberg, B; Minervini, G, 2014)	0.4
" In total, 136 adverse events (AEs) were observed in 71 (10."	( Real-life safety and efficacy of vildagliptin as add-on to metformin in patients with type 2 diabetes in Turkey--GALATA study. Akin, F; Ar, IB; Ayvaz, G; Dokmetas, HS; Keskin, L; Tasan, E; Uren, E, 2015)	0.42
" ASP015K was generally well tolerated, with no serious adverse events (AEs) reported."	( A phase 2a randomized, double-blind, placebo-controlled, sequential dose-escalation study to evaluate the efficacy and safety of ASP015K, a novel Janus kinase inhibitor, in patients with moderate-to-severe psoriasis. Akinlade, B; Ball, G; Catlin, M; Krueger, JG; Papp, K; Pariser, D; Wierz, G; Zeiher, B, 2015)	0.42
" The incidence of overall adverse events (AEs) and serious AEs was similar between saxagliptin and placebo in all cohorts; however, hypoglycemic events were higher for saxagliptin versus placebo regardless of age."	( Efficacy and safety of saxagliptin in older participants in the SAVOR-TIMI 53 trial. Bhatt, DL; Bonnici, F; Braunwald, E; Cahn, A; Frederich, R; Hirshberg, B; Kumar, KM; Leiter, LA; Mosenzon, O; Raz, I; Scirica, BM; Smahelova, A; Stahre, C; Teoh, H, 2015)	0.42
" The main outcomes were changes in glycosylated hemoglobin and the occurrence of adverse effects."	( [Safety and efficacy of Vildagliptin in real life Chilean diabetic patients]. Godoy J, G; Gutiérrez, V; Montecinos, M; Yenes, A, 2015)	0.42
" AZD9056 was well-tolerated, and no serious adverse events were reported."	( Safety and Efficacy of an Oral Inhibitor of the Purinergic Receptor P2X7 in Adult Patients with Moderately to Severely Active Crohn's Disease: A Randomized Placebo-controlled, Double-blind, Phase IIa Study. Braddock, M; Colombel, JF; Eser, A; Persson, T; Reinisch, W; Rutgeerts, P; Vermeire, S; Vogelsang, H, 2015)	0.42
" The primary endpoint was occurrence of major adverse CV events (MACEs; myocardial infarction, stroke and CV death)."	( Cardiovascular and heart failure safety profile of vildagliptin: a meta-analysis of 17 000 patients. Del Prato, S; Evans, M; Kothny, W; Lukashevich, V; McInnes, G; Schweizer, A; Shao, Q; Stumvoll, M, 2015)	0.42
" The total incidence of treatment-emergent adverse events (TEAEs) was similar between the placebo (64."	( Efficacy and safety of the oral Janus kinase inhibitor peficitinib (ASP015K) monotherapy in patients with moderate to severe rheumatoid arthritis in Japan: a 12-week, randomised, double-blind, placebo-controlled phase IIb study. Ishikura, H; Iwasaki, M; Kaneko, Y; Saeki, S; Takeuchi, T; Tanaka, Y, 2016)	0.43
" Safety endpoints included adverse events (AEs) and the incidence of hypoglycemia."	( Efficacy and safety of saxagliptin monotherapy or added to metformin in Chinese patients with type 2 diabetes mellitus: results from the 24-week, post-marketing SUNSHINE study. Gu, W; Li, Y; Liang, L; Ning, G; Piao, C; Tan, X; Tian, J; Wang, S; Wang, W; Wang, Y; Wu, Y; Xin, X; Yang, G; Yin, J, 2016)	0.43
" This paper discusses the tolerability and safety profile of the agent, including cardiovascular, renal, pancreatic, hepatic and bone adverse events."	( Saxagliptin for the treatment of diabetes - a focus on safety. Cahn, A; Cernea, S; Raz, I, 2016)	0.43
"Saxagliptin is a safe therapeutic option for patients with T2D, with low risk of hypoglycemia and good tolerability."	( Saxagliptin for the treatment of diabetes - a focus on safety. Cahn, A; Cernea, S; Raz, I, 2016)	0.43
" Pooled safety data were analyzed for adverse events (AEs) and hypoglycemia."	( A post hoc analysis of saxagliptin efficacy and safety in patients with type 2 diabetes stratified by UKPDS 10-year cardiovascular risk score. Bonora, E; Bryzinski, B; Cook, W; Hirshberg, B, 2016)	0.43
"We tested the possible association between dipeptidyl peptidase-4 inhibitors (DPP-4-I) use and heart failure (HF) occurrence by assessing the publicly available US-FDA Adverse Event Reporting System (FAERS)."	( Dipeptidyl peptidase-4 inhibitors and heart failure: Analysis of spontaneous reports submitted to the FDA Adverse Event Reporting System. Antonazzo, IC; De Ponti, F; Koci, A; Marchesini, G; Poluzzi, E; Raschi, E, 2016)	0.43
" Endpoints included changes in glycated albumin (GA), hemoglobin A1c (HbA1c), postprandial plasma glucose (PPG), and adverse events."	( Efficacy and safety of saxagliptin, a dipeptidyl peptidase-4 inhibitor, in hemodialysis patients with diabetic nephropathy: A randomized open-label prospective trial. Abe, M; Higuchi, T; Kikuchi, F; Moriuchi, M; Nagura, C; Okada, K; Okamura, M; Takashima, H; Tei, R; Tomita, H, 2016)	0.43
" There were no adverse events associated with saxagliptin."	( Efficacy and safety of saxagliptin, a dipeptidyl peptidase-4 inhibitor, in hemodialysis patients with diabetic nephropathy: A randomized open-label prospective trial. Abe, M; Higuchi, T; Kikuchi, F; Moriuchi, M; Nagura, C; Okada, K; Okamura, M; Takashima, H; Tei, R; Tomita, H, 2016)	0.43
" Adverse events were similar with dapagliflozin (66%) and placebo (71%), and hypoglycaemia was rare (≤2%)."	( Efficacy and safety of triple therapy with dapagliflozin add-on to saxagliptin plus metformin over 52 weeks in patients with type 2 diabetes. Chen, H; Garcia-Sanchez, R; González González, JG; Hansen, L; Herrera Marmolejo, M; Iqbal, N; Johnsson, E; Mathieu, C, 2016)	0.43
" Similar proportions of patients reported ≥1 adverse event with saxagliptin (58."	( One-year efficacy and safety of saxagliptin add-on in patients receiving dapagliflozin and metformin. Aggarwal, N; Chen, H; Chin, A; Garcia-Hernandez, P; Hansen, L; Iqbal, N; Johnsson, E; Matthaei, S, 2016)	0.43
" The key secondary endpoints included percentage of patients achieving target HbA1c without adverse gastrointestinal (GI) events and mean change in fasting plasma glucose (FPG) from baseline to week 24."	( Efficacy and safety of combination therapy with vildagliptin and metformin versus metformin uptitration in Chinese patients with type 2 diabetes inadequately controlled with metformin monotherapy: a randomized, open-label, prospective study (VISION). Ji, LN; Li, H; Li, Q; Li, QF; Lu, JM; Pan, CY; Peng, YD; Tian, HM; Wang, BH; Wang, L; Yao, C; Zhao, ZG; Zhu, DL, 2016)	0.43
"0%, the proportion of patients with gastrointestinal adverse events (GI AEs), and the proportion of patients achieving HbA1c < 7."	( Efficacy and safety of saxagliptin compared with acarbose in Chinese patients with type 2 diabetes mellitus uncontrolled on metformin monotherapy: Results of a Phase IV open-label randomized controlled study (the SMART study). Bian, F; Du, J; Fang, H; Li, W; Liang, L; Mu, Y; Shen, L; Wang, X; Xu, C; Xu, F, 2017)	0.46
" Safety was assessed by reporting of adverse events and serious adverse events (SAEs)."	( Effectiveness and safety of vildagliptin and vildagliptin add-on to metformin in real-world settings in Egypt - results from the GUARD study. Rakha, S; Shelbaya, S, 2017)	0.46
" The IRRs and their 95% CIs were close to 1, demonstrating no increased risk of adverse CV events, including the risk of CHF, with vildagliptin vs other NIADs in real-world conditions."	( Cardiovascular safety of vildagliptin in patients with type 2 diabetes: A European multi-database, non-interventional post-authorization safety study. Chu, C; de Vries, F; Kothny, W; Lopez-Leon, S; Schlienger, R; Serban, C; Williams, R, 2017)	0.46
" In terms of safety, the rate of adverse events in patients with T2D who received empagliflozin plus metformin was relatively lower when compared with saxagliptin plus metformin (OR=0."	( A network meta-analysis for efficacy and safety of seven regimens in the treatment of type II diabetes. Hua, WC; Li, CM; Liu, Q; Wang, H; Wang, LG, 2017)	0.46
"In the Saxagliptin Assessment of Vascular Outcomes Recorded in Patients with Diabetes Mellitus (SAVOR) trial in patients with type 2 diabetes mellitus (T2D) at high risk of cardiovascular (CV) disease, saxagliptin did not increase the risk for major CV adverse events."	( Nonclinical and clinical pharmacology evidence for cardiovascular safety of saxagliptin. Billger, M; Boulton, DW; Chadwick, KD; Hirshberg, B; Iqbal, N; Pollack, PS; Smith, DM, 2017)	0.46
" No treatment-emergent adverse events suggestive of heart failure or myocardial damage were reported."	( Nonclinical and clinical pharmacology evidence for cardiovascular safety of saxagliptin. Billger, M; Boulton, DW; Chadwick, KD; Hirshberg, B; Iqbal, N; Pollack, PS; Smith, DM, 2017)	0.46
" After 24 weeks, incidences of adverse events and serious adverse events were similar between triple and dual therapy and between concomitant and sequential add-on regimens."	( Safety and tolerability of dapagliflozin, saxagliptin and metformin in combination: Post-hoc analysis of concomitant add-on versus sequential add-on to metformin and of triple versus dual therapy with metformin. Chen, H; Del Prato, S; Garcia-Sanchez, R; Hansen, L; Iqbal, N; Johnsson, E; Mathieu, C; Rosenstock, J, 2018)	0.48
" As such, we assessed disproportionate reporting of major adverse cardiac events (MACE) among reports for DPP-4i submitted to the FDA Adverse Event Reporting System (FAERS) from 2006 to 2015."	( Cardiovascular safety signals with dipeptidyl peptidase-4 inhibitors: A disproportionality analysis among high-risk patients. Alexander, GC; Baksh, SN; McAdams-DeMarco, M; Segal, JB, 2018)	0.48
"3 million adverse event reports, 13."	( Cardiovascular safety signals with dipeptidyl peptidase-4 inhibitors: A disproportionality analysis among high-risk patients. Alexander, GC; Baksh, SN; McAdams-DeMarco, M; Segal, JB, 2018)	0.48
"Lipotoxicity cardiomyopathy is the result of excessive accumulation and oxidation of toxic lipids in the heart."	( Glucagon-like peptide-1 ameliorates cardiac lipotoxicity in diabetic cardiomyopathy via the PPARα pathway. Liu, L; Wang, DW; Wang, K; Wang, P; Wang, W; Wen, Z; Wu, L, 2018)	0.48
"Nephrotoxicity is a serious adverse effect frequently encountered with aminoglycosides administration."	( Nephroprotective effect of saxagliptin against gentamicin-induced nephrotoxicity, emphasis on anti-oxidant, anti-inflammatory and anti-apoptic effects. Helal, MG; Said, E; Zaki, MMAF, 2018)	0.48
" DAPA plus SAXA was generally well tolerated and the incidence of adverse events was similar in both treatment arms."	( Sustained 52-week efficacy and safety of triple therapy with dapagliflozin plus saxagliptin versus dual therapy with sitagliptin added to metformin in patients with uncontrolled type 2 diabetes. Del Prato, S; Garcia-Sanchez, R; Handelsman, Y; Iqbal, N; Johnsson, E; Kurlyandskaya, R; Mathieu, C; Rosenstock, J, 2019)	0.51
" Secondary endpoints (assessed throughout) included ACR20, ACR50 and ACR70 response, changes from baseline in disease activity scores (DAS)28 and ACR core parameters, adverse events (AEs) and changes in clinical or laboratory measurements."	( Efficacy and safety of peficitinib (ASP015K) in patients with rheumatoid arthritis and an inadequate response to conventional DMARDs: a randomised, double-blind, placebo-controlled phase III trial (RAJ3). Akazawa, R; Chen, YH; Iwasaki, M; Izutsu, H; Kaneko, Y; Kawakami, A; Lee, SH; Rokuda, M; Shiomi, T; Song, YW; Takeuchi, T; Tanaka, S; Tanaka, Y; Ushijima, S; Wei, JC; Yamada, E, 2019)	0.51
" The difference in the number of patients with adverse events (AEs) among the intervention groups was not statistically significant."	( Comparative Efficacy and Safety of Peficitinib 25, 50, 100, and 150 mg in Patients with Active Rheumatoid Arthritis: A Bayesian Network Meta-Analysis of Randomized Controlled Trials. Lee, YH; Song, GG, 2020)	0.56
" Two subjects (one in the normal group and one in the mildly impaired group) each experienced a treatment-emergent adverse event (TEAE)."	( Pharmacokinetics and Safety of a Single Oral Dose of Peficitinib (ASP015K) in Japanese Subjects with Normal and Impaired Renal Function. Furihata, K; Kaneko, Y; Katashima, M; Miyatake, D; Nishimura, T; Oda, K; Sekino, H; Shibata, M; Shibata, T; Urae, A, 2020)	0.56
" Treatment-emergent adverse events (TEAEs) were reported in 757/843 (89."	( Safety and effectiveness of peficitinib (ASP015K) in patients with rheumatoid arthritis: interim data (22.7 months mean peficitinib treatment) from a long-term, open-label extension study in Japan, Korea, and Taiwan. Chen, YH; Izutsu, H; Kaneko, Y; Kawakami, A; Nakashima, Y; Rokuda, M; Shiomi, T; Song, YW; Takeuchi, T; Tanaka, S; Tanaka, Y; Ushijima, S; Yamada, E, 2020)	0.56
" Pharmacokinetic and pharmacodynamic parameters were assessed, and adverse events (AEs) monitored throughout."	( Pharmacokinetics, Pharmacodynamics, and Safety of Peficitinib (ASP015K) in Healthy Male Caucasian and Japanese Subjects. Hatta, T; Kaneko, Y; Nishimura, T; Oda, K; Saito, M; Shibata, M; Toyoshima, J, 2020)	0.56
" Abuse of SCs is dangerous because users may mistake them for natural cannabis, which is generally considered to be unlikely to elicit adverse effects."	( Metabolism, CB1 cannabinoid receptor binding and in vivo activity of synthetic cannabinoid 5F-AKB48: Implications for toxicity. Bush, JM; Cabanlong, CV; Fantegrossi, WE; Fujiwara, R; Fukuda, S; Gogoi, J; Jackson, BK; McCain, K; Pinson, A; Prather, PL; Radominska-Pandya, A; Shoeib, A; Yarbrough, AL, 2020)	0.56
" No significant differences were observed in the incidence of serious adverse events after treatment with tofacitinib+MTX, peficitinib+MTX, adalimumab+MTX, or placebo+MTX."	( Comparison of the efficacy and safety of tofacitinib and peficitinib in patients with active rheumatoid arthritis: A Bayesian network meta-analysis of randomized controlled trials. Lee, YH; Song, GG, 2020)	0.56
"In patients with RA with an inadequate response to DMARDs, tofacitinib 10 mg+MTX and peficitinib 150 mg+MTX were the most efficacious interventions and were not associated with a significant risk of serious adverse events."	( Comparison of the efficacy and safety of tofacitinib and peficitinib in patients with active rheumatoid arthritis: A Bayesian network meta-analysis of randomized controlled trials. Lee, YH; Song, GG, 2020)	0.56
" However, the number of patients who experienced serious adverse events did not differ significantly between the JAK inhibitors, except for tofacitinib 5 mg, and placebo."	( Comparative efficacy and safety of tofacitinib, baricitinib, upadacitinib, filgotinib and peficitinib as monotherapy for active rheumatoid arthritis. Gyu Song, G; Ho Lee, Y, 2020)	0.56
" The outcomes included changes in HbA1c, FPG, body weight, SBP, DBP and adverse reactions."	( Efficacy and safety of dapagliflozin plus saxagliptin vs monotherapy as added to metformin in patients with type 2 diabetes: A meta-analysis. Li, M; Song, J; Ying, M; Zhuang, Y, 2020)	0.56
" Incidence rates per 100 patient-years (PY) of adverse events (AEs) of special interest were calculated."	( A pooled safety analysis of peficitinib (ASP015K) in Asian patients with rheumatoid arthritis treated over a median of 2 years. Fukuda, M; Izutsu, H; Kaneko, Y; Kato, D; Rokuda, M; Takeuchi, T; Tanaka, Y, 2021)	0.62
" Saxagliptin showed higher adverse reactions than acarbose and vildagliptin."	( A comparative study of acarbose, vildagliptin and saxagliptin intended for better efficacy and safety on type 2 diabetes mellitus treatment. Chen, Y; Dong, B; Hu, J; Wang, J; Wang, Y; Wang, Z, 2021)	0.62
" Incidence rates per 100 patient-years of adverse events of special interest were calculated, and Cox proportional hazard analysis was conducted."	( Impact of age on the efficacy and safety of peficitinib (ASP015K) for the treatment of rheumatoid arthritis. Fukuda, M; Kaneko, Y; Kato, D; Miyatake, D; Takeuchi, T; Tanaka, Y, 2022)	0.72
" The incidence of treatment-related adverse events (AEs) was also assessed."	( The efficacy and safety of tofacitinib, peficitinib, solcitinib, baricitinib, abrocitinib and deucravacitinib in plaque psoriasis - A network meta-analysis. Guo, L; Jiang, X; Wang, L; Zhang, L, 2022)	0.72
" 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

Excerpt	Reference	Relevance
"A phase I and pharmacokinetic study of a novel lipid-soluble antifolate, 2,4 diamino-5-adamantyl-6-methyl pyrimidine ethane sulfonate (DAMP-ES) has been carried out on two schedules: I--daily x5; II--24-h continuous infusion."	( Phase I clinical trial and human pharmacokinetics of 2,4-diamino-5-adamantyl-6-methyl pyrimidine ethane sulfonate (DAMP-ES): a lipid-soluble antifolate. Creaven, PJ; Greco, WR; Karakousis, C; Madajewicz, S; Mittelman, A; Pontes, JE; Proefrock, A; Takita, H; Zakrzewski, SF, 1988)	0.27
" No differences were observed among the age-stratified groups in measured or derived pharmacokinetic parameters."	( Multiple-dose pharmacokinetics of rimantadine in elderly adults. Gustavson, LE; Hayden, FG; Tominack, RL; Wills, RJ, 1988)	0.27
" The plasma half-life (43."	( Rimantadine pharmacokinetics in healthy subjects and patients with end-stage renal failure. Capparelli, EV; Chow, MS; Izard, M; Stevens, RC; Wills, RJ, 1988)	0.27
" The half-life of rimantadine in young adults was 27."	( Pharmacokinetics of a single dose of rimantadine in young adults and children. Anderson, EL; Bartram, J; Belshe, RB; Hoffman, HE; Van Voris, LP, 1987)	0.27
"22 micrograms/ml), plasma elimination half-life (36."	( Comparative single-dose pharmacokinetics of amantadine hydrochloride and rimantadine hydrochloride in young and elderly adults. Hayden, FG; Hoffman, HE; Minocha, A; Spyker, DA, 1985)	0.27
" Pharmacokinetic data were successfully fitted to a model consisting of central and peripheral DAMP compartments and a DAMP metabolite compartment."	( Toxicity and pharmacokinetics of a new antifolate, 2,4-diamino-5-adamantyl-6-methylpyrimidine, in dogs. Bullard, G; Creaven, PJ; Greco, WR; Mihich, E; Pavelic, Z; Zakrzewski, SF, 1982)	0.26
" Thus, there was a need to identify an analogue with an improved pharmacokinetic (PK) profile."	( Second generation "peptoid" CCK-B receptor antagonists: identification and development of N-(adamantyloxycarbonyl)-alpha-methyl-(R)-tryptophan derivative (CI-1015) with an improved pharmacokinetic profile. Boden, P; Eden, JM; Field, MJ; Hill, D; Hinton, JP; Holmes, A; Kneen, C; Padia, JK; Pritchard, MC; Rose, S; Singh, L; Suman-Chauhan, N; Trivedi, BK; Webdale, L; Wright, DS, 1998)	0.3
" equivalent body surface area dose, the terminal half-life (t1/2) of SQ109 in dogs was longer than that in rodents, reflected by a larger volume of distribution (Vss) and a higher clearance rate of SQ109 in dogs, compared to that in rodents."	( Interspecies pharmacokinetics and in vitro metabolism of SQ109. Coward, L; Gorman, GS; Jia, L; Noker, PE; Protopopova, M; Tomaszewski, JE, 2006)	0.33
"To assess the pharmacokinetic and pharmacodynamic characteristics and tolerability of vildagliptin at doses of 10 mg, 25 mg and 100 mg twice daily following oral administration in patients with type 2 diabetes."	( Pharmacokinetics and pharmacodynamics of vildagliptin in patients with type 2 diabetes mellitus. Campestrini, J; Deacon, CF; He, YL; Holst, JJ; Ligueros-Saylan, M; Nielsen, JC; Riviere, GJ; Schwartz, S; Serra, D; Wang, Y, 2007)	0.34
" This open-label, randomized, 3-period crossover study investigated the potential for pharmacokinetic interactions in 18 healthy subjects during coadministration of vildagliptin and digoxin."	( Evaluation of pharmacokinetic interactions between vildagliptin and digoxin in healthy volunteers. Bizot, MN; Dole, WP; He, YL; Howard, D; Leon, S; Ligueros-Saylan, M; Riviere, GJ; Sabo, R; Sunkara, G, 2007)	0.34
" Noncompartmental analysis and population pharmacokinetic modelling were performed."	( The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers. Balez, S; Campestrini, J; He, YL; Howard, D; Laurent, A; Ligueros-Saylan, M; Sabo, R; Sadler, BM; Wang, Y, 2007)	0.34
"Both noncompartmental analysis and population pharmacokinetic modelling estimated the absolute oral bioavailability of vildagliptin to be 85%."	( The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers. Balez, S; Campestrini, J; He, YL; Howard, D; Laurent, A; Ligueros-Saylan, M; Sabo, R; Sadler, BM; Wang, Y, 2007)	0.34
" However, their relatively low metabolic stability leads to poor pharmacokinetic properties."	( 1,3-disubstituted ureas functionalized with ether groups are potent inhibitors of the soluble epoxide hydrolase with improved pharmacokinetic properties. Hammock, BD; Kasagami, T; Kim, IH; Morisseau, C; Nishi, K; Tsai, HJ, 2007)	0.34
" There fore, this study was conducted to determine the potential for pharmacokinetic drug-drug interaction between vildagliptin and simvastatin at steady-state."	( Evaluation of the potential for steady-state pharmacokinetic interaction between vildagliptin and simvastatin in healthy subjects. Ayalasomayajula, SP; Campestrini, J; Dole, K; He, YL; Humbert, H; Ligueros-Saylan, M; Sunkara, G; Wang, Y, 2007)	0.34
" Pharmacokinetic and statistical analyses were performed using WinNonlin and SAS, respectively."	( Evaluation of the potential for steady-state pharmacokinetic interaction between vildagliptin and simvastatin in healthy subjects. Ayalasomayajula, SP; Campestrini, J; Dole, K; He, YL; Humbert, H; Ligueros-Saylan, M; Sunkara, G; Wang, Y, 2007)	0.34
"We conducted 3 open-label, multiple-dose, 3-period, randomized, crossover studies in healthy subjects to assess the potential pharmacokinetic interaction between vildagliptin, a novel dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes, and representatives of 3 commonly prescribed antihypertensive drug classes: (1) the calcium channel blocker, amlodipine; (2) the angiotensin receptor blocker, valsartan; and (3) the angiotensin-converting enzyme inhibitor, ramipril."	( Vildagliptin, a novel dipeptidyl peptidase IV inhibitor, has no pharmacokinetic interactions with the antihypertensive agents amlodipine, valsartan, and ramipril in healthy subjects. Campestrini, J; Dole, K; Dole, WP; He, YL; Howard, D; Ligueros-Saylan, M; Marion, A; Pommier, F; Sabo, R; Sunkara, G; Wang, Y; Zhao, C, 2008)	0.35
" Two studies were performed to determine the potential for pharmacokinetic and pharmacodynamic interactions between vildagliptin and the sulfonylurea, glyburide, or pioglitazone in patients with Type 2 diabetes."	( Evaluation of pharmacokinetic and pharmacodynamic interaction between the dipeptidyl peptidase IV inhibitor vildagliptin, glyburide and pioglitazone in patients with Type 2 diabetes. Balez, S; Bullock, J; Dole, WP; He, YL; Jarugula, V; Ligueros-Saylan, M; Riviere, GJ; Schwartz, S; Serra, D; Wang, Y, 2008)	0.35
" Changes in AUC and Cmax during combination treatment were small ( pound 15%), and 90% confidence intervals for the geometric mean ratios (drug coadministration/monotherapy) were generally contained within the acceptance range for bioequivalence (0."	( Evaluation of pharmacokinetic and pharmacodynamic interaction between the dipeptidyl peptidase IV inhibitor vildagliptin, glyburide and pioglitazone in patients with Type 2 diabetes. Balez, S; Bullock, J; Dole, WP; He, YL; Jarugula, V; Ligueros-Saylan, M; Riviere, GJ; Schwartz, S; Serra, D; Wang, Y, 2008)	0.35
"0 hours) across the dose range of 25 to 200 mg and was quickly eliminated with a terminal elimination half-life (t1/2) of approximately 2 hours."	( Pharmacokinetics and pharmacodynamics of vildagliptin in healthy Chinese volunteers. Deckert, F; Dole, WP; He, YL; Hu, P; Jiang, J; Kjems, L; Liu, D; Yin, Q, 2009)	0.35
" Blood samples for pharmacokinetic sampling were taken frequently on the final day (Day 5) of each treatment period."	( Study of the pharmacokinetic interaction of vildagliptin and metformin in patients with type 2 diabetes. Dole, WP; He, YL; Herron, J; Ligueros-Saylan, M; Picard, F; Sabo, R; Wang, Y, 2009)	0.35
" PK/pharmacodynamics characteristics, that is, sufficiently prolonged half-life and sustained DPP-4 enzyme inactivation, generally allow one single oral administration per day for the management of T2DM; the only exception is vildagliptin for which a twice-daily administration is recommended because of a shorter half-life."	( Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Scheen, AJ, 2010)	0.36
" In the present study, OZ78 was administered at 50mg/kg orally and subcutaneously to sheep harbouring an experimental Fasciola hepatica infection and the efficacy, tolerability and pharmacokinetic profiles were monitored."	( Efficacy, safety and pharmacokinetics of 1,2,4-trioxolane OZ78 against an experimental infection with Fasciola hepatica in sheep. Dong, Y; Haschke, M; Huwyler, J; Kaminsky, R; Keiser, J; Kirchhofer, C; Malikides, N; Vanhoff, K; Vennerstrom, JL, 2010)	0.36
" Oral administration of 13 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors in mice revealed substantial improvements in pharmacokinetic parameters over previously reported 1-adamantylurea based inhibitors."	( 1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain. Hammock, BD; Inceoglu, B; Jones, PD; Liu, JY; Morisseau, C; Rose, TE; Sanborn, JR, 2010)	0.36
" In order to support the development of OZ78, including pharmacokinetic (PK) studies an accurate, precise, and selective liquid chromatography/mass spectrometry (LC/MS) method for OZ78 was developed for sheep plasma and validated in accordance with the US Food and Drug Administration Guidance on Bioanalytical Method Validation."	( Development and validation of a liquid chromatography/mass spectrometry method for pharmacokinetic studies of OZ78, a fasciocidal drug candidate. Huwyler, J; Keiser, J; Kirchhofer, C, 2010)	0.36
"Vildagliptin demonstrated similar pharmacokinetic and pharmacodynamic effects in Japanese patients to those observed previously in non-Japanese patients with Type 2 diabetes."	( Pharmacokinetics and pharmacodynamics of vildagliptin in Japanese patients with type 2 diabetes. He, YL; Ito, H; Sekiguchi, K; Terao, S; Yamaguchi, M, 2010)	0.36
"91 μM × h, and its half-life was 11."	( Adamantanyl-histone deacetylase inhibitor H6CAHA exhibits favorable pharmacokinetics and augments prostate cancer radiation sensitivity. Cao, H; Jung, M; Konsoula, Z; Velena, A, 2011)	0.37
"To evaluate the pharmacokinetic interactions of the potent, selective, dipeptidyl peptidase-4 inhibitor, saxagliptin, in combination with metformin, glyburide or pioglitazone."	( Saxagliptin, a potent, selective inhibitor of DPP-4, does not alter the pharmacokinetics of three oral antidiabetic drugs (metformin, glyburide or pioglitazone) in healthy subjects. Boulton, DW; Brenner, E; Handschuh del Corral, M; Komoroski, B; Kornhauser, D; Li, L; Patel, CG; Vachharajani, N, 2011)	0.37
" The drug was rapidly absorbed with a mean terminal half-life ranging from 3 to 5 hours."	( Pharmacokinetics and pharmacodynamics of AR9281, an inhibitor of soluble epoxide hydrolase, in single- and multiple-dose studies in healthy human subjects. Anandan, SK; Chen, D; Do, ZN; Gless, R; MacIntyre, E; Patel, DV; Sabry, J; Tran, V; Webb, HK; Whitcomb, R, 2012)	0.38
" Vildagliptin possesses several desirable pharmacokinetic properties that contribute to its lower variability and low potential for drug interaction."	( Clinical pharmacokinetics and pharmacodynamics of vildagliptin. He, YL, 2012)	0.38
" By utilizing the TMDD approach, slow dissociation of vildagliptin from DPP-4 was found in patients and the half-life of hydrolysis by DPP-4 estimated."	( Mechanism-based population pharmacokinetic modelling in diabetes: vildagliptin as a tight binding inhibitor and substrate of dipeptidyl peptidase IV. He, YL; Jusko, WJ; Landersdorfer, CB, 2012)	0.38
" Pharmacokinetic variables for saxagliptin (primary outcome) and its active metabolite, 5-hydroxy saxagliptin (secondary outcome), after single and multiple oral doses of saxagliptin were assessed."	( Pharmacokinetic study of saxagliptin in healthy Chinese subjects. Li, H; Patel, CG; Tou, CK; Yang, L; Zhao, J, 2012)	0.38
"The safety and pharmacokinetic profile of OZ439 merits progression to phase 2a proof of concept studies in the target population of acute uncomplicated malaria."	( First-in-man safety and pharmacokinetics of synthetic ozonide OZ439 demonstrates an improved exposure profile relative to other peroxide antimalarials. Arbe-Barnes, S; Charman, SA; Craft, JC; Duparc, S; Gutierrez, M; Moehrle, JJ; Siethoff, C; van Giersbergen, PL; Vennerstrom, JL; Wittlin, S, 2013)	0.39
" A population pharmacokinetic model was constructed for ABT-384 and its metabolites using NonMEM."	( Effect of ketoconazole on the pharmacokinetics of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor ABT-384 and its two active metabolites in healthy volunteers: population analysis of data from a drug-drug interaction study. An, G; Awni, W; Dutta, S; Katz, DA; Liu, W; Marek, G, 2013)	0.39
"Reliable prediction of two fundamental human pharmacokinetic (PK) parameters, systemic clearance (CL) and apparent volume of distribution (Vd), determine the size and frequency of drug dosing and are at the heart of drug discovery and development."	( Quantitative structure-activity relationship models of clinical pharmacokinetics: clearance and volume of distribution. Gombar, VK; Hall, SD, 2013)	0.39
"Compared to age-, gender-, BMI-matched subjects with normal renal function, the mean AUC of vildagliptin after 14 days in patients with mild, moderate, and severe RI increased by 40%, 71%, and 100%, respectively, and the Cmax of vildagliptin showed similar and minimal increases of 37%, 32% and 36%, respectively."	( Pharmacokinetics of vildagliptin in patients with varying degrees of renal impairment. He, YL; Kulmatycki, K; Ligueros-Saylan, M; Reynolds, C; Taylor, A; Zhang, Y; Zhou, W, 2013)	0.39
"To assess the extent of pharmacokinetic and pharmacodynamic interaction between vildagliptin, a potent and selective inhibitor of dipeptidyl peptidase IV (DPP-4) enzyme, and voglibose, an α-glucosidase inhibitor widely prescribed in Japan, when coadministered in Japanese patients with Type 2 diabetes."	( Pharmacokinetic and pharmacodynamic interaction of vildagliptin and voglibose in Japanese patients with Type 2 diabetes. Furihata, K; He, YL; Kulmatycki, K; Mita, S; Saji, T; Sekiguchi, K; Yamaguchi, M, 2013)	0.39
" Co-administration led to significantly better pharmacodynamic response compared with each treatment alone, including higher active GLP-1 and lower glucose levels."	( Pharmacokinetic and pharmacodynamic interaction of vildagliptin and voglibose in Japanese patients with Type 2 diabetes. Furihata, K; He, YL; Kulmatycki, K; Mita, S; Saji, T; Sekiguchi, K; Yamaguchi, M, 2013)	0.39
" Plasma mean peak concentration was 11."	( Efficacy and pharmacokinetics of OZ78 and MT04 against a natural infection with Fasciola hepatica in sheep. Bosco, A; Cringoli, G; Duthaler, U; Huwyler, J; Keiser, J; Meister, I; Rinaldi, L, 2013)	0.39
" Four of the five commercially available DPP-4 inhibitors are subject to significant renal clearance, and pharmacokinetic studies in people with renal impairment have led to lower recommended doses based on creatinine clearance in order to prevent drug accumulation."	( Dipeptidyl peptidase-4 inhibitors: pharmacokinetics, efficacy, tolerability and safety in renal impairment. Davis, TM, 2014)	0.4
"This review considers the pharmacokinetic profile, adverse effects and drug interactions of DPP-4 inhibitors."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" However, DPP-4 inhibitors have certain differences in their pharmacokinetic properties that may be associated with different clinical effects and adverse event profiles."	( The pharmacokinetic considerations and adverse effects of DPP-4 inhibitors [corrected]. Athyros, VG; Elisaf, MS; Filippatos, TD, 2014)	0.4
" This phenomenon cannot be explained by the half-life of ABT-384."	( Population pharmacokinetics of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor ABT-384 in healthy volunteers following single and multiple dose regimens. An, G; Awni, W; Dutta, S; Katz, DA; Liu, W; Marek, GJ, 2014)	0.4
"The availability of intravenous and oral pharmacokinetic data in animals enabled the allometry scaling of 6 DPP-IV inhibitors."	( Retrospective and Prospective Human Intravenous and Oral Pharmacokinetic Projection of Dipeptidyl peptidase-IV Inhibitors Using Simple Allometric Principles - Case Studies of ABT-279, ABT-341, Alogliptin, Carmegliptin, Sitagliptin and Vildagliptin. Bhamidipati, RK; Gilibili, RR; Mullangi, R; Srinivas, NR, 2015)	0.42
" A population pharmacokinetic (PPK) analysis of pooled metformin concentration-time data was performed to evaluate whether country-sourced metformin is a significant covariate."	( Population pharmacokinetic modeling and noncompartmental analysis demonstrated bioequivalence between metformin component of metformin/vildagliptin fixed-dose combination products and metformin immediate-release tablet sourced from various countries. Chitnis, SD; Han, Y; Kulmatycki, K; Mita, S; Sunkara, G; Yamaguchi, M; Zhao, R, 2016)	0.43
" The half-life of plasma DPP-4 inhibition with saxagliptin 5 mg is ~27 h, which supports a once-daily dosing regimen."	( Clinical Pharmacokinetics and Pharmacodynamics of Saxagliptin, a Dipeptidyl Peptidase-4 Inhibitor. Boulton, DW, 2017)	0.46
"This single-dose, open-label, randomized, 3-period, 3-treatment crossover drug-drug interaction study was conducted to evaluate differences in the pharmacokinetic properties of saxagliptin and dapagliflozin when coadministered."	( Lack of a Pharmacokinetic Interaction Between Saxagliptin and Dapagliflozin in Healthy Subjects: A Randomized Crossover Study. Boulton, DW; LaCreta, F; Liang, D; Lubin, S; Marion, AS; Reynolds, L; Vakkalagadda, B, 2016)	0.43
" Serial blood samples for determining saxagliptin, 5-hydroxy saxagliptin (5-OH saxagliptin; major active metabolite) and dapagliflozin plasma concentrations and pharmacokinetic parameters were collected before and up to 60 hours after the dose."	( Lack of a Pharmacokinetic Interaction Between Saxagliptin and Dapagliflozin in Healthy Subjects: A Randomized Crossover Study. Boulton, DW; LaCreta, F; Liang, D; Lubin, S; Marion, AS; Reynolds, L; Vakkalagadda, B, 2016)	0.43
"The results indicated that dapagliflozin had no effect on the pharmacokinetic properties of saxagliptin, 5-OH saxagliptin, or saxagliptin total active moiety and vice versa."	( Lack of a Pharmacokinetic Interaction Between Saxagliptin and Dapagliflozin in Healthy Subjects: A Randomized Crossover Study. Boulton, DW; LaCreta, F; Liang, D; Lubin, S; Marion, AS; Reynolds, L; Vakkalagadda, B, 2016)	0.43
"These data indicate that coadministration of saxagliptin and dapagliflozin exhibits no pharmacokinetic interaction and is well tolerated."	( Lack of a Pharmacokinetic Interaction Between Saxagliptin and Dapagliflozin in Healthy Subjects: A Randomized Crossover Study. Boulton, DW; LaCreta, F; Liang, D; Lubin, S; Marion, AS; Reynolds, L; Vakkalagadda, B, 2016)	0.43
" To determine the rate of DPP-4 inhibition induced by these inhibitors, pharmacokinetic and pharmacodynamic parameters were used to theoretically examine the relationship between the rate of DPP-4 inhibition and clinical efficacy following the administration of four different DPP-4 inhibitors (sitagliptin, vildagliptin, alogliptin, linagliptin) by focusing on the increase in the level of glucagon-like peptide-1 (GLP-1) induced by their administration."	( Evaluation of drug efficacy of DPP-4 inhibitors based on theoretical analysis with pharmacokinetics and pharmacodynamics. Kimura, K; Takayanagi, R; Uchida, T; Yamada, Y, 2017)	0.46
" The effects of verapamil, an inhibitor of the efflux pump P-gp, on the pharmacokinetic profile of peficitinib were assessed in this open-label, single-center, single-sequence, crossover drug-interaction study."	( The Effect of Verapamil, a P-Glycoprotein Inhibitor, on the Pharmacokinetics of Peficitinib, an Orally Administered, Once-Daily JAK Inhibitor. Fisniku, O; Garg, JP; Han, D; Howieson, C; Keirns, J; Wojtkowski, T; Zhu, T, 2017)	0.46
" Areas covered: The saxagliptin plus dapagliflozin combination is carefully analysed, focusing on: 1) pharmacokinetic properties, 2) pharmacodynamics data, and 3) results of randomised controlled trials (dual combination versus either monotherapy, sequential therapy saxagliptin added to dapagliflozin or dapagliflozin added to saxagliptin)."	( Pharmacokinetic drug evaluation of saxagliptin plus dapagliflozin for the treatment of type 2 diabetes. Scheen, AJ, 2017)	0.46
" Blood samples were collected prior to administration and up to 72 h post-dose for pharmacokinetic assessment."	( Pharmacokinetics and Safety of a Single Oral Dose of Peficitinib (ASP015K) in Japanese Subjects with Normal and Impaired Renal Function. Furihata, K; Kaneko, Y; Katashima, M; Miyatake, D; Nishimura, T; Oda, K; Sekino, H; Shibata, M; Shibata, T; Urae, A, 2020)	0.56
" The impact of hepatic impairment on the peficitinib pharmacokinetic (PK) and safety profile was investigated in non-RA subjects (n = 24) in an open-label, parallel-group, multicenter comparative study in Japan."	( Pharmacokinetics and Safety of a Single Oral Dose of Peficitinib (ASP015K) in Japanese Subjects With Normal and Impaired Hepatic Function. Furihata, K; Inoue, K; Ito, T; Kaneko, Y; Katashima, M; Miyatake, D; Nishimura, T; Oda, K; Sakaki, M; Shibata, T; Toyoshima, J; Uchida, N; Urae, A, 2020)	0.56
" Pharmacokinetic and pharmacodynamic parameters were assessed, and adverse events (AEs) monitored throughout."	( Pharmacokinetics, Pharmacodynamics, and Safety of Peficitinib (ASP015K) in Healthy Male Caucasian and Japanese Subjects. Hatta, T; Kaneko, Y; Nishimura, T; Oda, K; Saito, M; Shibata, M; Toyoshima, J, 2020)	0.56
" Samples for pharmacokinetic analysis were collected before dose and ≤72 hours after dose."	( The Bioequivalence of Two Peficitinib Formulations, and the Effect of Food on the Pharmacokinetics of Peficitinib: Two-Way Crossover Studies of a Single Dose of 150 mg Peficitinib in Healthy Volunteers. Kambayashi, A; Kaneko, Y; Kiyota, T; Nishimura, T; Oda, K; Shibata, M; Toyoshima, J, 2021)	0.62
"1 L/kg), and a short terminal half-life (0."	( Pharmacokinetic Characterization of LW6, a Novel Hypoxia-Inducible Factor-1α (HIF-1α) Inhibitor in Mice. Kang, JS; Kim, JA; Kim, MJ; Lee, JY; Lee, K; Oh, SJ; Shin, EJ; Yoo, DG, 2021)	0.62
"We characterized the impact of chronic kidney disease (CKD) on the cytochrome P450 (CYP) 3A4-mediated metabolism of saxagliptin to its metabolite, 5-hydroxysaxagliptin, using a physiologically based pharmacokinetic (PBPK) model."	( Use of Physiologically Based Pharmacokinetic Modeling to Evaluate the Impact of Chronic Kidney Disease on CYP3A4-Mediated Metabolism of Saxagliptin. Boulton, DW; Butrovich, MA; Nolin, TD; Sharma, P; Tang, W, 2022)	0.72
"The aim of the present study is to develop physiologically based pharmacokinetic (PBPK) models for saxagliptin and its active metabolite, 5-hydroxy saxagliptin, and to predict the effect of coadministration of rifampicin, a strong inducer of cytochrome P450 3A4 enzymes, on the pharmacokinetics of saxagliptin and 5-hydroxy saxagliptin in patients with renal impairment."	( Physiologically Based Pharmacokinetic Modeling Characterizes the Drug-Drug Interaction Between Saxagliptin and Rifampicin in Patients With Renal Impairment. Ke, M; Lin, C; Lin, R; Wu, W; Ye, L, 2023)	0.91

Excerpt	Reference	Relevance
" Inoculation of remantadine in combination with nontoxic concentrations of sodium selenite was found to be a promising combination for inhibition of experimental influenza infection."	( [Antiviral action of sodium selenite and its combination with remantadine]. Abdullaev, FI; Abdullaev, II; Lazymova, ZA; Sycheva, IV; Veselovskaia, TV, )	0.13
"It was shown advisable to use ribavirin (a weak inhibitor of Sindbis virus reproduction) in combination with ACAA."	( [Effect of the amide of 1-adamantanecarboxylic acid (AACA) and its combination with ribavirin on the course of experimental infection, caused by the sindbis virus in tissue culture and in mouse brain. Possible isolation of the virus mutant resistant to ri Andronova, VL, 1997)	0.6
"The purpose of this study was to assess the efficacy and tolerability of the dipeptidyl peptidase-4 inhibitor vildagliptin in combination with the thiazolidinedione (TZD) pioglitazone in patients with type 2 diabetes (T2DM)."	( Vildagliptin in combination with pioglitazone improves glycaemic control in patients with type 2 diabetes failing thiazolidinedione monotherapy: a randomized, placebo-controlled study. Baron, MA; Dejager, S; Garber, AJ; Rochotte, E; Schweizer, A, 2007)	0.34
" The added efficacy of saxagliptin in combination with other OADs in improving glycemic parameters has resulted in a significant proportion of patients achieving an HbA1c <7% versus monotherapy or active comparator."	( Reaching HbA1c goals with saxagliptin in combination with other oral antidiabetic drugs. LaSalle, JR, 2010)	0.36
"Patients with type 2 diabetes mellitus (T2DM) are generally treated with many pharmacological compounds and are exposed to a high risk of drug-drug interactions."	( Dipeptidylpeptidase-4 inhibitors (gliptins): focus on drug-drug interactions. Scheen, AJ, 2010)	0.36
"Dipeptidyl peptidase-4 inhibitors improve glycaemic control in patients with type 2 diabetes mellitus when used as monotherapy or in combination with other anti-diabetic drugs (metformin, sulphonylurea, or thiazolidinedione)."	( Efficacy and safety of saxagliptin in combination with metformin compared with sitagliptin in combination with metformin in adult patients with type 2 diabetes mellitus. Charpentier, G; Gause-Nilsson, I; Hellqvist, A; Ostgren, CJ; Scheen, AJ, 2010)	0.36
" A third gliptin, saxagliptin, is now authorised in the European Union for second-line treatment of type 2 diabetes, in combination with metformin, a glucose-lowering sulphonylurea, or a glitazone."	( Saxagliptin. No more effective than other gliptins, but a high potential for drug interactions. , 2011)	0.37
"Saxagliptin in combination with MET or SU is likely to represent a cost-effective treatment option in Polish patients with type 2 diabetes failing first-line treatment."	( The cost-effectiveness of saxagliptin versus NPH insulin when used in combination with other oral antidiabetes agents in the treatment of type 2 diabetes mellitus in Poland. Czupryniak, L; Grzeszczak, W; Kolasa, K; Lomon, ID; McEwan, P; Sciborski, C, 2012)	0.38
"To evaluate efficacy and safety of saxagliptin as add-on therapy in patients with type 2 diabetes (T2D) with inadequate glycemic control on insulin alone or combined with metformin."	( Effect of saxagliptin as add-on therapy in patients with poorly controlled type 2 diabetes on insulin alone or insulin combined with metformin. Barnett, AH; Charbonnel, B; Chen, R; Donovan, M; Fleming, D, 2012)	0.38
"Saxagliptin 5-mg once-daily add-on therapy improves glycemic control in T2D patients on insulin alone or combined with metformin and is generally well-tolerated."	( Effect of saxagliptin as add-on therapy in patients with poorly controlled type 2 diabetes on insulin alone or insulin combined with metformin. Barnett, AH; Charbonnel, B; Chen, R; Donovan, M; Fleming, D, 2012)	0.38
"73 m(2), 100 randomized to vildagliptin, 78 randomized to placebo), all of whom were receiving insulin therapy (alone or in combination with an oral antidiabetic agent) for longstanding type 2 diabetes (mean approximately 19 years)."	( Efficacy of vildagliptin in combination with insulin in patients with type 2 diabetes and severe renal impairment. Dickinson, S; Foley, JE; Groop, PH; Kothny, W; Lukashevich, V; Schweizer, A, 2013)	0.39
"With vildagliptin in combination with insulin, the adjusted mean change (AMΔ) in HbA(1c) from baseline (7."	( Efficacy of vildagliptin in combination with insulin in patients with type 2 diabetes and severe renal impairment. Dickinson, S; Foley, JE; Groop, PH; Kothny, W; Lukashevich, V; Schweizer, A, 2013)	0.39
" The data support the use of vildagliptin in combination with insulin in general and, in line with emerging clinical practice, suggest that treating patients with vildagliptin, metformin, and basal insulin could be an attractive therapeutic option."	( Clinical evidence and mechanistic basis for vildagliptin's effect in combination with insulin. Ahrén, B; Foley, JE; Kothny, W; Schweizer, A, 2013)	0.39
" We evaluated the effects of long-term treatment with vildagliptin, a DPP-4 inhibitor, on metabolic parameters and β-cell function, in combination with miglitol, an alpha-glucosidase inhibitor, in diet-controlled db/db mice."	( Beneficial effects of vildagliptin combined with miglitol on glucose tolerance and islet morphology in diet-controlled db/db mice. Abe, H; Fujitani, Y; Hara, A; Ishibashi, K; Kanazawa, A; Kawamori, R; Komiya, K; Ogihara, T; Tamaki, M; Uchida, T; Watada, H, 2013)	0.39
" This first study in patients was done to determine safety, tolerability, pharmacokinetics and bacteriological effect of different doses of SQ109 alone and in combination with rifampicin when administered over 14 days."	( Early phase evaluation of SQ109 alone and in combination with rifampicin in pulmonary TB patients. Aarnoutse, RE; Boeree, MJ; Dawson, R; Diacon, AH; du Bois, J; Gillespie, SH; Heinrich, N; Henne, S; Hoelscher, M; Horwith, G; Nacy, CA; Narunsky, K; Phillips, PP; Phipps, AJ; Rachow, A; Venter, A, 2015)	0.42
" We report here that a low-carbohydrate diet combined with an SGLT2 inhibitor was effective and safe to treat refractory hyperglycemia in the perioperative period in a type 2 diabetes patient complicated with a high titer of insulin antibodies."	( Low-carbohydrate diet combined with SGLT2 inhibitor for refractory hyperglycemia caused by insulin antibodies. Abiru, N; Ando, T; Horie, I; Kawakami, A; Shigeno, R, 2016)	0.43
"To evaluate the efficacy and safety of orally administered once-daily peficitinib in combination with limited conventional synthetic disease-modifying antirheumatic drugs (csDMARDs) in patients with moderate-to-severe rheumatoid arthritis (RA)."	( Peficitinib, a JAK Inhibitor, in Combination With Limited Conventional Synthetic Disease-Modifying Antirheumatic Drugs in the Treatment of Moderate-to-Severe Rheumatoid Arthritis. Cardiel, MH; Codding, C; Garg, JP; Genovese, MC; Greenwald, M; Kivitz, AJ; Shay, K; Wang, A; Wang, X; Zubrzycka-Sienkiewicz, A, 2017)	0.46
"In patients with moderate-to-severe RA, orally administered once-daily peficitinib in combination with limited csDMARDs resulted in a dose-dependent ACR20 response rate over 12 weeks with satisfactory tolerability."	( Peficitinib, a JAK Inhibitor, in Combination With Limited Conventional Synthetic Disease-Modifying Antirheumatic Drugs in the Treatment of Moderate-to-Severe Rheumatoid Arthritis. Cardiel, MH; Codding, C; Garg, JP; Genovese, MC; Greenwald, M; Kivitz, AJ; Shay, K; Wang, A; Wang, X; Zubrzycka-Sienkiewicz, A, 2017)	0.46
" In an open-label, drug-drug interaction study, 24 healthy volunteers received a single dose of metformin 750 mg on Days 1 and 10, and a single dose of peficitinib 150 mg on Days 3 and 5-11."	( A drug-drug interaction study to evaluate the impact of peficitinib on OCT1- and MATE1-mediated transport of metformin in healthy volunteers. Kaneko, Y; Nishimura, T; Oda, K; Shibata, M; Toyoshima, J, 2020)	0.56
"Nowadays, it is possible to combine X-ray crystallography and fragment screening in a medium throughput fashion to chemically probe the surfaces used by proteins to interact and use the outcome of the screens to systematically design protein-protein inhibitors."	( Mining the PDB for Tractable Cases Where X-ray Crystallography Combined with Fragment Screens Can Be Used to Systematically Design Protein-Protein Inhibitors: Two Test Cases Illustrated by IL1β-IL1R and p38α-TAB1 Complexes. Conte, MR; De Nicola, GF; Fraternali, F; Kelly, G; Keshu, A; Marber, MS; Ng, J; Nichols, C, 2020)	0.56
"The objective of this study was to investigate potential drug-drug interactions of peficitinib with methotrexate and the short-term safety of coadministration."	( Investigation of Potential Drug-Drug Interactions between Peficitinib (ASP015K) and Methotrexate in Patients with Rheumatoid Arthritis. Akinlade, B; Cao, Y; Chindalore, V; Moy, S; Sawamoto, T; Valluri, U; Zhang, W; Zhu, T, 2020)	0.56
" Then, the effect of renal impairment combined with drug-drug interaction on saxagliptin and 5-hydroxy saxagliptin pharmacokinetics was investigated."	( Physiologically Based Pharmacokinetic Modeling Characterizes the Drug-Drug Interaction Between Saxagliptin and Rifampicin in Patients With Renal Impairment. Ke, M; Lin, C; Lin, R; Wu, W; Ye, L, 2023)	0.91

Excerpt	Reference	Relevance
" There were no changes in the rate of absorption and the renal clearance of rimantadine when it was administered with cimetidine."	( Effect of cimetidine on the disposition of rimantadine in healthy subjects. Brown, SY; Choma, N; Holazo, AA; Lee, LF; Wills, RJ, 1989)	0.28
" The bioavailability after an oral dose of 40 mg/kg was 58."	( Pharmacokinetics and metabolism of rimantadine hydrochloride in mice and dogs. Blasecki, JW; Gaylord, JC; Hoffman, HE; Shalaby, LM; Whitney, CC, 1988)	0.27
"Twenty healthy male subjects completed an open-label randomized crossover design to assess the bioavailability of 100 mg of rimantadine HCl in tablet and syrup forms relative to an oral solution."	( Relative bioavailability of rimantadine HCl tablet and syrup formulations in healthy subjects. Buonpane, G; Choma, N; Keigher, N; Lin, A; Wills, RJ, 1987)	0.27
" dose ratio was approximately one, suggesting that LY353433 was well absorbed with excellent pharmacodynamics in the rat."	( LY353433, a potent, orally effective, long-acting 5-HT(4) receptor antagonist: comparison to cisapride and RS23597-190. Bloomquist, W; Calligaro, DA; Cohen, I; Cohen, ML; Schaus, JM; Susemichel, AD; Thompson, DC, 1996)	0.29
"Based on the physicochemical and pharmacological properties of drugs having an adamantane skeleton, an adamantane-based moiety was evaluated as a drug carrier for poorly absorbed compounds, including peptides, active towards the central nervous system (CNS)."	( Synthesis and antinociceptive activity of [D-Ala2]Leu-enkephalin derivatives conjugated with the adamantane moiety. Futaki, S; Hama, T; Hibi, T; Kitagawa, K; Konishi, R; Mizobuchi, N, 1997)	0.74
" However, during its development, it was determined that CI-988 had low bioavailability in both rodent and nonrodent species."	( Second generation "peptoid" CCK-B receptor antagonists: identification and development of N-(adamantyloxycarbonyl)-alpha-methyl-(R)-tryptophan derivative (CI-1015) with an improved pharmacokinetic profile. Boden, P; Eden, JM; Field, MJ; Hill, D; Hinton, JP; Holmes, A; Kneen, C; Padia, JK; Pritchard, MC; Rose, S; Singh, L; Suman-Chauhan, N; Trivedi, BK; Webdale, L; Wright, DS, 1998)	0.3
"Although prediction of the plasma profile of lipophilic drugs solely on the basis of in vitro data remains an ambitious target, this study shows that the plasma profile of a lipophilic drug can be predicted with appropriate in vitro dissolution data, provided that the absolute bioavailability of the drug is known and the drug has dissolution limited absorption."	( Biorelevant dissolution testing to predict the plasma profile of lipophilic drugs after oral administration. Dressman, JB; Nicolaides, E; Reppas, C; Symillides, M, 2001)	0.31
" The results suggest that 12j is a potent, stable, selective DPP-IV inhibitor possessing excellent oral bioavailability and potent antihyperglycemic activity with potential for once-a-day administration."	( 1-[[(3-hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties. Brinkman, JA; Burkey, BF; Dunning, BE; Hughes, TE; Mangold, BL; Naderi, GB; Prasad, K; Russell, ME; Villhauer, EB, 2003)	0.32
"1-[[(3-Hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties."	( Inhibition of dipeptidyl-peptidase IV catalyzed peptide truncation by Vildagliptin ((2S)-{[(3-hydroxyadamantan-1-yl)amino]acetyl}-pyrrolidine-2-carbonitrile). Brandt, I; Chen, X; De Meester, I; Joossens, J; Lambeir, AM; Maes, MB; Scharpé, S, 2005)	0.33
" Pharmacokinetic studies showed that the esters possess improved oral bioavailability in mice."	( Design of bioavailable derivatives of 12-(3-adamantan-1-yl-ureido)dodecanoic acid, a potent inhibitor of the soluble epoxide hydrolase. Blanchfield, J; Bradford, T; Hammock, BD; Kim, IH; Koda, Y; Morisseau, C; Nishi, K; Toth, I; Tsai, HJ; Watanabe, T, 2007)	0.34
"05 nM) had excellent oral bioavailability (98%, n = 2) and blood area under the curve in dogs and was effective in vivo to treat hypotension in lipopolysaccharide challenged murine models."	( Orally bioavailable potent soluble epoxide hydrolase inhibitors. Hammock, BD; Hwang, SH; Liu, JY; Morisseau, C; Tsai, HJ, 2007)	0.34
" The objective of this study was to assess the absolute oral bioavailability of vildagliptin by comparing the systemic exposure after oral and intravenous administration in healthy volunteers."	( The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers. Balez, S; Campestrini, J; He, YL; Howard, D; Laurent, A; Ligueros-Saylan, M; Sabo, R; Sadler, BM; Wang, Y, 2007)	0.34
"Both noncompartmental analysis and population pharmacokinetic modelling estimated the absolute oral bioavailability of vildagliptin to be 85%."	( The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers. Balez, S; Campestrini, J; He, YL; Howard, D; Laurent, A; Ligueros-Saylan, M; Sabo, R; Sadler, BM; Wang, Y, 2007)	0.34
"Vildagliptin is rapidly and well absorbed with an estimated absolute bioavailability of 85%."	( The absolute oral bioavailability and population-based pharmacokinetic modelling of a novel dipeptidylpeptidase-IV inhibitor, vildagliptin, in healthy volunteers. Balez, S; Campestrini, J; He, YL; Howard, D; Laurent, A; Ligueros-Saylan, M; Sabo, R; Sadler, BM; Wang, Y, 2007)	0.34
" Thus, a functional interplay between membrane Gb3 and MDR1 provides a more physiologically based approach to MDR1 regulation to increase the bioavailability of chemotherapeutic drugs."	( Inhibition of multidrug resistance by adamantylgb3, a globotriaosylceramide analog. Ackerley, C; Clarke, DM; De Rosa, MF; Ito, S; Lingwood, C; Wang, B, 2008)	0.35
" An optimal pharmacokinetic profile of low oral bioavailability was combined with a strong pharmacology profile when assessed using a guinea pig trachea tissue model."	( The discovery of adamantyl-derived, inhaled, long acting beta(2)-adrenoreceptor agonists. Brown, AD; Bunnage, ME; Glossop, PA; James, K; Jones, R; Lane, CA; Lewthwaite, RA; Mantell, S; Perros-Huguet, C; Price, DA; Trevethick, M; Webster, R, 2008)	0.35
" The rate of absorption of metformin was decreased when given with food, as reflected by the prolonged t(max) (2-4 h) and reduction in C(max) (by 26%), but the extent of absorption was not changed."	( Effect of food on the pharmacokinetics of a vildagliptin/metformin (50/1000 mg) fixed-dose combination tablet in healthy volunteers. Campestrini, J; Flannery, B; He, YL; Jarugula, V; Leon, S; Ligueros-Saylan, M; Zinny, MA, 2008)	0.35
" Moderate to high bioavailability was observed in both species (45-100%)."	( Disposition of vildagliptin, a novel dipeptidyl peptidase 4 inhibitor, in rats and dogs. Filipeck, R; Fischer, V; Flood, D; He, H; Howard, D; Kramp, R; Smith, H; Tran, P; Yin, H, 2009)	0.35
" Saxagliptin was rapidly absorbed and had good bioavailability (50-75%) in the species tested."	( Pharmacokinetics of the dipeptidyl peptidase 4 inhibitor saxagliptin in rats, dogs, and monkeys and clinical projections. Boulton, DW; Caporuscio, C; Chadwick, KD; Chang, SY; Christopher, LJ; Fura, A; Hamann, LG; Humphreys, WG; Khanna, A; Kirby, M; Koplowitz, B; Vyas, V, 2009)	0.35
"The low bioavailability of SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy."	( Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents. Li, W; Liu, Y; Luo, H; Meng, Q; Yao, Q; Zhang, W, 2009)	0.35
" Preliminary results show low and variable drug absorption in patients, with extensive glucuroconjugation influencing the bioavailability of ST1926."	( Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ST1926, a novel oral antitumor agent, adamantyl retinoid derivative, in plasma of patients in a Phase I study. Bagnati, R; Capocasa, F; D'Incalci, M; Marangon, E; Pace, S; Sala, F; Zucchetti, M, 2009)	0.35
"Although considerably less potent than specified DPP-IV inhibitors, the possibility that some of the beneficial actions of nateglinide are indirectly mediated through DPP-IV inhibition and increased bioavailability of GIP and other incretins merits consideration."	( Insulinotropic actions of nateglinide in type 2 diabetic patients and effects on dipeptidyl peptidase-IV activity and glucose-dependent insulinotropic polypeptide degradation. Bell, PM; Duffy, NA; Flatt, PR; Green, BD; Lindsay, JR; McKillop, AM; O'Harte, FP; Patterson, S, 2009)	0.35
" Saxagliptin is well absorbed and has low plasma protein binding and displays slow-binding properties to DPP IV."	( Saxagliptin: a new drug for the treatment of type 2 diabetes. Aggarwal, S; Bhardwaj, TR; Haksar, D; Kumar, M; Malla, P; Thareja, S, 2010)	0.36
" Saxagliptin is well absorbed after oral administration and demonstrates a pharmacokinetic profile that is compatible with once-daily dosing."	( Saxagliptin: a new dipeptidyl peptidase 4 inhibitor for type 2 diabetes. Borja-Hart, NL; Whalen, KL, 2010)	0.36
" All together gliptins have a good oral bioavailability which is not significantly influenced by food intake."	( Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Scheen, AJ, 2010)	0.36
" Lipoyl vildagliptin might have very high CL/F values and V(d)/F values, which indicated that the bioavailability of this drug might be low or lipoyl vildagliptin might distribute extensively or accumulate in tissues in view of its high liposolubility."	( Pharmacokinetics of lipoyl vildagliptin, a novel dipeptidyl peptidase IV inhibitor after oral administration in rats. Liu, H; Wang, W; Wang, X; Xu, W; Zhang, D, 2010)	0.36
" Optimization for increased adipocyte potency, metabolic stability and selectivity afforded 11k and 11l, both of which were >25% orally bioavailable in rat."	( Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1. Berbaum, J; Bruno, JG; Bukhtiyarov, Y; Claremon, DA; Gregg, RE; Guo, J; Guo, R; Harrison, RK; Howard, L; Johnson, JA; Krosky, PM; Kruk, BA; Leftheris, K; Lindblom, PR; McGeehan, GM; McKeever, BM; Nar, H; Panemangalore, R; Schuler-Metz, A; Scott, BB; Singh, SB; Tice, CM; Togias, J; Ye, YJ; Zhao, W; Zhao, Y; Zhuang, L, 2010)	0.36
" These results indicate that pharmacological inhibition of Sphk2 with the orally bioavailable selective inhibitor, ABC294640, has therapeutic potential in the treatment of chemo- and endocrine therapy- resistant breast cancer."	( Targeting NFĸB mediated breast cancer chemoresistance through selective inhibition of sphingosine kinase-2. Antoon, JW; Beckman, BS; Burow, ME; Driver, JL; Elliott, S; Khalili, HS; Slaughter, EM; Smith, CD; White, MD, 2011)	0.37
" We also demonstrated a markedly enhanced oral bioavailability of the prodrugs versus the parent drug in mice."	( Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues. Andrei, G; Balzarini, J; Camarasa, MJ; De Meester, I; Diez-Torrubia, A; Snoeck, R; Velázquez, S, 2011)	0.37
" N-(1-adamantyl)-2-oxo-chromene-3-carboxamide (8), N-adamantan-1-yl-5-dimethyl-amino-1-naphthalenesulfonic acid (11) and N-(1-cyano-2H-isoindol-2-yl) adamantan-1-amine (12) were found to possess a high degree of multifunctionality with favourable physical-chemical properties for bioavailability and blood-brain barrier permeability."	( Synthesis and evaluation of fluorescent heterocyclic aminoadamantanes as multifunctional neuroprotective agents. Green, IR; Joubert, J; Malan, SF; van Dyk, S, 2011)	0.61
" Following oral administration, vildagliptin is rapidly and well absorbed with an absolute bioavailability of 85%."	( Clinical pharmacokinetics and pharmacodynamics of vildagliptin. He, YL, 2012)	0.38
" Taken together, the excretion data suggest that saxagliptin was well absorbed and was subsequently cleared by both urinary excretion and metabolism; the formation of M2 was the major metabolic pathway."	( Characterization of the in vitro and in vivo metabolism and disposition and cytochrome P450 inhibition/induction profile of saxagliptin in human. Barros, A; Bonacorsi, SJ; Boulton, DW; Cao, K; Christopher, LJ; Humphreys, WG; Iyer, RA; Su, H; Wang, L, 2012)	0.38
" However, active compounds to date have high cLogP's and are poorly soluble, leading to low bioavailability and thus limiting any therapeutic application."	( Screening a library of 1600 adamantyl ureas for anti-Mycobacterium tuberculosis activity in vitro and for better physical chemical properties for bioavailability. Grzegorzewicz, AE; Hess, TN; Jackson, M; Jones, V; Kasagami, T; Kim, IH; Lee, RE; Lenaerts, AJ; McNeil, MR; Merzlikin, O; Morisseau, C; North, EJ; Scherman, MS, 2012)	0.38
" It was established that the original substance is characterized by low absolute bioavailability (7."	( Absolute bioavailability of himantane in rabbits. Alekseev, KV; Bastrygin, DV; Kolyvanov, GB; Litvin, EA; Zherdev, VP, 2012)	0.38
"To determine the absolute oral bioavailability (F(p."	( Simultaneous oral therapeutic and intravenous ¹⁴C-microdoses to determine the absolute oral bioavailability of saxagliptin and dapagliflozin. Arnold, ME; Boulton, DW; Christopher, LJ; Kasichayanula, S; Keung, CF; Lacreta, F; Xu, XS, 2013)	0.39
"An absolute bioavailability study that utilized an intravenous [(14)C]microdose was conducted for saxagliptin (Onglyza(®)), a marketed drug product for the treatment of Type 2 diabetes mellitus."	( Overcoming bioanalytical challenges in an Onglyza(®) intravenous [(14)C]microdose absolute bioavailability study with accelerator MS. Arnold, ME; Bonacorsi, SJ; Cao, KK; Christopher, LJ; Cojocaru, L; Dueker, SR; Humphreys, WG; Keung, CF; Lohstroh, PN; Shen, JX; Stouffer, B; Xu, XS, 2012)	0.38
" In this study, we have conjugated DFOB to derivatives of adamantane or the clinical iron chelator deferasirox to produce lipophilic compounds designed to increase the bioavailability of DFOB to brain cells."	( Lipophilic adamantyl- or deferasirox-based conjugates of desferrioxamine B have enhanced neuroprotective capacity: implications for Parkinson disease. Codd, R; Crouch, PJ; Ganio, G; Liddell, JR; Liu, J; Mok, SS; Obando, D; Volitakis, I; White, AR, 2013)	0.63
" These efforts led to the identification of 26, an orally bioavailable inhibitor of human 11β-HSD1 with a favorable development profile."	( Synthesis and structure-activity relationship of 2-adamantylmethyl tetrazoles as potent and selective inhibitors of human 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). Apedo, A; Chen, SY; Golla, R; Gordon, DA; Harper, T; He, B; Kirby, M; Li, YX; Nayeem, A; Robl, JA; Seethala, R; Sleczka, BG; Wang, M; Ye, XY; Yoon, D, 2014)	0.4
"The characterization of absolute bioavailability (BA) is useful for non-intravenous (iv."	( Sensitivity-based analytical approaches to support human absolute bioavailability studies. Arnold, ME; Christopher, LJ; Jiang, H; Shen, JX; Xu, XS; Zeng, J, 2014)	0.4
" The rate of absorption of metformin decreased when administered under fed condition, as reflected by a prolonged t(max) (3 hours in fasted state vs."	( Bioequivalence and food effect assessment for vildagliptin/metformin fixed-dose combination tablets relative to free combination of vildagliptin and metformin in Japanese healthy subjects. Chitnis, SD; He, YL; Kulmatycki, K; Mita, S; Salunke, A; Suzuki, H; Zhou, W, 2016)	0.43
" Pharmacokinetic and pharmacodynamic evaluations of 18a revealed improved bioavailability and superior gonadotropic suppression activity compared with Elagolix, the most clinically advanced compound."	( Discovery of an Orally Bioavailable Gonadotropin-Releasing Hormone Receptor Antagonist. Ann, J; Han, MY; Kim, EJ; Kim, SM; Lee, J; Lee, M; Lee, SM; Lee, SY; Park, E; Yoo, T; Yoon, S, 2016)	0.43
" The combination of the replacement of a pyridine ring of 9 with a pyrimidine ring and the introduction of an additional fluorine substituent at the 2-position of the phenyl ring resulted in the discovery of a potent, selective, and orally bioavailable inhibitor, 18a (SKI2852), which demonstrated no CYP and PXR liabilities, excellent PK profiles across species, and highly potent and sustainable PD activity."	( Discovery of 2-((R)-4-(2-Fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1R,2s,3S,5S,7S)-5-hydroxyadamantan-2-yl)pyrimidine-4-carboxamide (SKI2852): A Highly Potent, Selective, and Orally Bioavailable Inhibitor of 11β-Hydroxysteroid Dehydroge Han, HY; Kim, JS; Kim, S; Kim, YH; Lee, J; Lee, JA; Park, HG; Ryu, JH; Sa, JH; Shin, YA; Son, HJ; Yang, J, 2016)	0.43
" We have applied Flash NanoPrecipitation (FNP), a polymer-directed self-assembly process, to form stable, water-dispersible nanoparticles (NPs) of 50-400 nm in size containing OZ439, a poorly orally bioavailable but promising candidate for single-dose malaria treatment developed by Medicines for Malaria Venture (MMV)."	( Encapsulation of OZ439 into Nanoparticles for Supersaturated Drug Release in Oral Malaria Therapy. Dobrijevic, ELK; Feng, J; Lu, HD; McManus, SA; Mulhearn, WD; Patel, A; Prud'homme, RK; Ramachandruni, H; Ristroph, KD; Zhang, Y, 2018)	0.48
"Milk has been used as a vehicle for the delivery of antimalarial drugs during clinical trials to test for a food effect and artefenomel (OZ439) showed enhanced oral bioavailability with milk."	( Interactions of Artefenomel (OZ439) with Milk during Digestion: Insights into Digestion-Driven Solubilization and Polymorphic Transformations. Boyd, BJ; Clulow, AJ; Hawley, A; Khan, J; Ramachandruni, H; Ramirez, G; Salim, M, 2018)	0.48
" Here, we describe the identification of the novel orally bioavailable JAK inhibitor 18, peficitinib (also known as ASP015K), which showed moderate selectivity for JAK3 over JAK1, JAK2, and TYK2 in enzyme assays."	( Discovery and structural characterization of peficitinib (ASP015K) as a novel and potent JAK inhibitor. Amano, Y; Hamaguchi, H; Higashi, Y; Inoue, T; Ito, M; Moritomo, A; Nakai, K; Nakajima, Y; Nomura, N; Shirakami, S, 2018)	0.48
" Therefore, synthetic retinoids were developed, such as the atypical adamantyl retinoid ST1926 that provides enhanced bioavailability and reduced toxicity."	( The synthetic retinoid ST1926 attenuates prostate cancer growth and potentially targets prostate cancer stem-like cells. Abdel-Samad, R; Abou-Kheir, W; Bahmad, HF; Cheaito, K; Darwiche, N; Hadadeh, O; Hayar, B; Liu, YN; Monzer, A; Msheik, H; Pisano, C; Samman, H, 2019)	0.51
", 7-day treatment) with LC478 on P-gp known to affect docetaxel bioavailability in rats."	( Effect of treatment period with LC478, a disubstituted adamantayl derivative, on P-glycoprotein inhibition: its application to increase docetaxel absorption in rats. Ahn, HC; Chae, HS; Chin, YW; Choi, YH; Chung, SJ; Han, SY; Kim, ES; Lee, K; Lu, Q; You, BH, 2020)	0.56
" Peficitinib, an orally bioavailable inhibitor of the Janus kinase (JAK) receptor family, was approved in Japan in 2019 and Korea in 2020 for the treatment of RA."	( Peficitinib for the treatment of rheumatoid arthritis: an overview from clinical trials. Izutsu, H; Tanaka, Y, 2020)	0.56
"Topical formulation of non-steroidal anti-inflammatory drugs (NSAIDs) exhibits many advantages over the oral administration route, such as avoiding the direct effect on GIT and avoiding the poor oral bioavailability of such drugs."	( Cyclodextrin/Adamantane-Grafted Polyethylene Glycol-Based Self-assembling Constructs for Topical Delivery of Ketorolac Tromethamine: Formulation, Characterization, and In Vivo Studies. Abdellatif, AAH; Almawash, S; El-Rasoul, SA; Mohammed, AM; Osman, SK; Safwat, MA; Zayed, G, 2022)	1.09
" The main objective was to modify therapy with adamantane derivatives: amantadine and rimantadine, to increase their bioavailability and evaluate the influence of such therapy on drug metabolism using Saccharomyces cerevisiae as the model organism."	( Metabolic profiling to evaluate the impact of amantadine and rimantadine on the secondary metabolism of a model organism. Barchanska, H; Kostina-Bednarz, M; Płonka, J, 2023)	1.17

Excerpt	Relevance	Reference
" These findings suggest that rimantadine dosage may need to be reduced in patients with end-stage renal disease but supplemental doses on dialysis days are not required."	( Rimantadine pharmacokinetics in healthy subjects and patients with end-stage renal failure. Capparelli, EV; Chow, MS; Izard, M; Stevens, RC; Wills, RJ, 1988)	0.27
" Concomitant intratracheal dosing of 200 micrograms of inhibitor with the enzyme significantly reduces lung damage as measured by quasi-static lung compliance and by histological assessment of the emphysema."	( The effect of a peptide aldehyde reversible inhibitor of elastase on a human leucocyte elastase-induced model of emphysema in the hamster. Cline, A; Johnson, WH; Kennedy, AJ; Ney, UM; Roberts, NA, 1987)	0.27
" A dosage of 200 mg of either drug for a 3-5-day period is effective but treatment has to commence on the first day of symptoms."	( Current status of amantadine and rimantadine as anti-influenza-A agents: memorandum from a WHO meeting. , 1985)	0.27
" Administration of 50 mg of the drug for 15-30 days was effective for prevention of influenza, and administration, early in the course of illness, of dosage of 150 mg per day for three to five days resulted in a favorable clinical response."	( Study of rimantadine in the USSR: a review of the literature. Kamforin, LE; Kovaleva, TP; Kubar, OI; Zlydnikov, DM, )	0.13
" To provide an overview for physicians and patients on the diversity of preparations available in the different countries, we compiled the most commonly used substances along with their size of dosage and formula in an international guide to drugs for PD."	( International guide to drugs for Parkinson's disease. Dodel, RC; Oertel, WH, 1995)	0.29
" dosing with responses returning to control by 16 hr, indicative of long duration receptor blockade."	( LY353433, a potent, orally effective, long-acting 5-HT(4) receptor antagonist: comparison to cisapride and RS23597-190. Bloomquist, W; Calligaro, DA; Cohen, I; Cohen, ML; Schaus, JM; Susemichel, AD; Thompson, DC, 1996)	0.29
" Thrice daily dosing at a 4-h interval with the short-acting agent SKF 82958 maintained the maximal antiparkinsonian response but some shortening in the duration of response was observed after several days."	( Dopamine D1 receptor desensitization profile in MPTP-lesioned primates. Bédard, PJ; Blanchet, PJ; Britton, DR; Grondin, R; Shiosaki, K, 1996)	0.29
" Although the compound is less water soluble than CI-988, oral bioavailability in rat was improved nearly 10 times relative to CI-988 when dosed in HP beta CD."	( Second generation "peptoid" CCK-B receptor antagonists: identification and development of N-(adamantyloxycarbonyl)-alpha-methyl-(R)-tryptophan derivative (CI-1015) with an improved pharmacokinetic profile. Boden, P; Eden, JM; Field, MJ; Hill, D; Hinton, JP; Holmes, A; Kneen, C; Padia, JK; Pritchard, MC; Rose, S; Singh, L; Suman-Chauhan, N; Trivedi, BK; Webdale, L; Wright, DS, 1998)	0.3
") increased Na+ excretion and reduced renal venous PRA independent of hemodynamics, whereas half this dosage selectively reduced renal venous PRA and renin release, independent of hemodynamics and natriuresis."	( K-ATP-blocking diuretic PNU-37883A reduces plasma renin activity in dogs. Humphrey, SJ; Ludens, JH, 1998)	0.3
" Differences between products (both in vitro or in vivo) were less pronounced than differences due to media composition (in vitro) or dosing conditions (in vivo)."	( Forecasting the in vivo performance of four low solubility drugs from their in vitro dissolution data. Dressman, JB; Efthymiopoulos, C; Galia, E; Nicolaides, E; Reppas, C, 1999)	0.3
" We also provide evidence of deficient NT neurotransmission as well as a left-shifted antipsychotic drug dose-response curve in isolation-reared rats."	( Enhanced neurotensin neurotransmission is involved in the clinically relevant behavioral effects of antipsychotic drugs: evidence from animal models of sensorimotor gating. Binder, EB; Kilts, CD; Kinkead, B; Nemeroff, CB; Owens, MJ, 2001)	0.31
" In patients with renal insufficiency, careful dosage adjustment is mandatory to optimize drug exposure and reduce the risk for adverse events."	( Anti-viral drugs in continuous ambulatory peritoneal dialysis (CAPD). Deray, G; Issad, B; Izzedine, H; Launay-Vacher, V, 2002)	0.31
" This study examined acute (single dose) and chronic (once-a-day dosing for 21 days) effects of the DPP-4 inhibitor vildagliptin (0."	( Acute and chronic effects of the incretin enhancer vildagliptin in insulin-resistant rats. Balkan, B; Bolognese, L; Burkey, BF; Hughes, TE; Li, X; Mone, M; Russell, M; Wang, PR, 2005)	0.33
" In mice and dogs dosed with adaphostin, plasma concentrations of the compound decreased rapidly."	( Preclinical pharmacology of the novel antitumor agent adaphostin, a tyrphostin analog that inhibits bcr/abl. Covey, JM; Grossi, I; Hill, DL; Li, M; Peggins, J; Stinson, S; Veley, K; Wang, H; Zhang, R, 2006)	0.33
" There was no apparent dose-response in the overall population; however, in patients with high baseline HbA1c, there were greater reductions with either 100 mg dose regimen (Delta=-1."	( Vildagliptin in drug-naïve patients with type 2 diabetes: a 24-week, double-blind, randomized, placebo-controlled, multiple-dose study. Dejager, S; Foley, JE; Razac, S; Schweizer, A, 2007)	0.34
" Because no prospective data exist on the efficacy of these agents in humans for H5N1 strains, the dosage and duration of therapy in adults and children may differ from those documented to be effective for epidemic influenza strains."	( Antiviral therapy and prophylaxis for influenza in children. , 2007)	0.34
"This randomized, open-label, placebo-controlled, 7-period crossover study assessed dose-response relationships following single oral doses (10-400 mg) of vildagliptin in 16 patients with type 2 diabetes mellitus."	( Pharmacodynamics of vildagliptin in patients with type 2 diabetes during OGTT. Bullock, JM; Deacon, CF; Dunning, BE; Foley, JE; He, YL; Holst, JJ; Ligueros-Saylan, M; Wang, Y, 2007)	0.34
" No dosage adjustment of either warfarin or vildagliptin is necessary when these drugs are co-medicated."	( Effect of the novel oral dipeptidyl peptidase IV inhibitor vildagliptin on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects. Dole, WP; He, YL; Howard, D; Leon, S; Ligueros-Saylan, M; Riviere, GJ; Rosenberg, M; Sabo, R; Sunkara, G, 2007)	0.34
" No adjustment in dosage based on pharmacokinetic considerations is required should vildagliptin be coadministered with amlodipine, valsartan, or ramipril in patients with type 2 diabetes and hypertension."	( Vildagliptin, a novel dipeptidyl peptidase IV inhibitor, has no pharmacokinetic interactions with the antihypertensive agents amlodipine, valsartan, and ramipril in healthy subjects. Campestrini, J; Dole, K; Dole, WP; He, YL; Howard, D; Ligueros-Saylan, M; Marion, A; Pommier, F; Sabo, R; Sunkara, G; Wang, Y; Zhao, C, 2008)	0.35
" Both types of blocker weakened arecoline tremor, though the dose-response relationships were different for mono-and dications."	( Involvement of ionotropic glutamate receptors in the appearance of arecoline tremor in mice. Gmiro, VE; Lavrent'eva, VV; Lukomskaya, NY; Magazanik, LG; Starshinova, LA; Zhabko, EP, 2008)	0.35
" The mean plasma concentration 24 h after dose after 12-week daily dosing with 1500 mg/kg/day in mice was 2279 nM."	( Adverse effects of dipeptidyl peptidases 8 and 9 inhibition in rodents revisited. Burkey, BF; Foley, JE; Hassiepen, U; Hoffmann, PK; Juedes, M; Trappe, J, 2008)	0.35
"The domestic drug himantane has been used as a monotherapy in dosage 25 mg daily during 12 weeks in patients with Parkinson's disease."	( [The possibilities of using himantane in the treatment of Parkinson's disease]. Avakian, GN; Katunina, EA; Nerobkova, LN; Petrukhova, AV; Saiadian, KhS; Val'dman, EA; Voronina, TA, 2008)	0.35
" Continuous dosing of the sEH inhibitors 12-(3-adamantan-1-ylureido)-dodecanoic acid (AUDA), a polyethylene glycol ester of AUDA, and 1-adamantan-1-yl-3-(5-(2-(2-ethoxyethoxy)ethoxy)-pentyl)urea resulted in robust exposure to the inhibitor and target engagement, as evidenced by significant increases in plasma EET/DHET ratios following 6 days of inhibitor treatment."	( Inhibition of soluble epoxide hydrolase does not protect against endotoxin-mediated hepatic inflammation. Fife, KL; Hammock, BD; Kim, IH; Kroetz, DL; Liu, Y; Morisseau, C; Schmelzer, KR; Tsai, HJ, 2008)	0.35
" Vildagliptin 25 to 200 mg qd exhibits approximately dose-proportional pharmacokinetics with no evidence of accumulation after multiple dosing in healthy Chinese participants."	( Pharmacokinetics and pharmacodynamics of vildagliptin in healthy Chinese volunteers. Deckert, F; Dole, WP; He, YL; Hu, P; Jiang, J; Kjems, L; Liu, D; Yin, Q, 2009)	0.35
" The primary objective was to demonstrate that HbA(1c) reduction with once-daily vildagliptin 100 mg AM dosing is superior to placebo."	( Efficacy and tolerability of vildagliptin in patients with type 2 diabetes inadequately controlled with metformin monotherapy. Goodman, M; Penman, J; Thurston, H, 2009)	0.35
" Data from previous experiments were included, and negative binomial regression analyses were carried out to determine dose-response relationships and to study the effect of drug combination."	( Combination chemotherapy against Clonorchis sinensis: experiments with artemether, artesunate, OZ78, praziquantel, and tribendimidine in a rat model. Keiser, J; Smith, TA; Utzinger, J; Xiao, SH, 2009)	0.35
" Dosing of oseltamivir was variable, illustrating the need for pharmacokinetic data in this younger population."	( Safety of oseltamivir compared with the adamantanes in children less than 12 months of age. Abughali, N; Abzug, MJ; Bradley, JS; Cloud, GA; Englund, J; Griffin, J; Guzman-Cottrill, J; Jacobs, RF; Jester, P; Kimberlin, DW; Lang, D; Leach, C; Ramilo, O; Robinson, J; Romero, JR; Shalabi, M; Shelton, M; Storch, G; Wade, KC; Whitley, RJ, 2010)	0.63
" sinensis, dosed orally with single agents or combination treatments and flukes recovered at 3 or 5 days post-treatment."	( Effect of artemether, artesunate, OZ78, praziquantel, and tribendimidine alone or in combination chemotherapy on the tegument of Clonorchis sinensis. Keiser, J; Vargas, M, 2010)	0.36
" In clinical trials, once or twice daily dosing with vildagliptin (up to 100 mg day(-1)) has been shown to reduce endogenous glucose production and fasting plasma glucose in patients with type 2 diabetes."	( Hormonal and metabolic effects of morning or evening dosing of the dipeptidyl peptidase IV inhibitor vildagliptin in patients with type 2 diabetes. Dole, WP; Foley, J; He, YL; Ligueros-Saylan, M; Schwartz, SL; Valencia, J; Zhang, Y, 2010)	0.36
"Once daily dosing with vildagliptin 100 mg for 28 days improved glycaemic control in patients with type 2 diabetes independent of whether vildagliptin was administered in the morning or evening."	( Hormonal and metabolic effects of morning or evening dosing of the dipeptidyl peptidase IV inhibitor vildagliptin in patients with type 2 diabetes. Dole, WP; Foley, J; He, YL; Ligueros-Saylan, M; Schwartz, SL; Valencia, J; Zhang, Y, 2010)	0.36
"Forty-eight patients were randomized to once daily vildagliptin 100 mg administered before breakfast or before dinner for 28 days then crossed over to the other dosing regimen."	( Hormonal and metabolic effects of morning or evening dosing of the dipeptidyl peptidase IV inhibitor vildagliptin in patients with type 2 diabetes. Dole, WP; Foley, J; He, YL; Ligueros-Saylan, M; Schwartz, SL; Valencia, J; Zhang, Y, 2010)	0.36
"5,24 h) was greater with evening than morning dosing (-336 vs."	( Hormonal and metabolic effects of morning or evening dosing of the dipeptidyl peptidase IV inhibitor vildagliptin in patients with type 2 diabetes. Dole, WP; Foley, J; He, YL; Ligueros-Saylan, M; Schwartz, SL; Valencia, J; Zhang, Y, 2010)	0.36
"Both morning and evening dosing of once daily vildagliptin 100 mg significantly reduced post-prandial glucose in patients with type 2 diabetes; only evening dosing significantly decreased fasting plasma glucose."	( Hormonal and metabolic effects of morning or evening dosing of the dipeptidyl peptidase IV inhibitor vildagliptin in patients with type 2 diabetes. Dole, WP; Foley, J; He, YL; Ligueros-Saylan, M; Schwartz, SL; Valencia, J; Zhang, Y, 2010)	0.36
" Negative binomial regressions of worm and egg counts were used to analyze dose-response relationships and whether the effects of drug combinations were synergistic or antagonistic."	( In vivo and in vitro sensitivity of Fasciola hepatica to triclabendazole combined with artesunate, artemether, or OZ78. Duthaler, U; Keiser, J; Smith, TA, 2010)	0.36
" Oseltamivir may be particularly appealing for treating children since it is available in multiple oral dosage formulations, whereas commercially available zanamivir use is limited in young children because it requires inhalation."	( Antivirals for influenza: strategies for use in pediatrics. Gums, JG; Smith, SM, 2010)	0.36
"In patients with T2DM treated with metformin XR, saxagliptin 5 mg orally administered once daily in the evening for 4 weeks effectively lowered plasma glucose concentrations through the 24-hour dosing interval and was well tolerated."	( Saxagliptin and metformin XR combination therapy provides glycemic control over 24 hours in patients with T2DM inadequately controlled with metformin. Berglind, N; Chen, R; Neutel, J; Ravichandran, S; Raz, I; Stenlöf, K, 2010)	0.36
"The pharmacology, pharmacokinetics, efficacy, safety, and dosage and administration of saxagliptin are reviewed."	( Saxagliptin: a dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes mellitus. Campbell, RK; Neumiller, JJ, 2010)	0.36
" There are important differences in the kinetics of the interaction of different gliptins with the catalytic site of DPP-4, which may lead to varying pharmacokinetics, pharmacodynamics and dosing regimens."	( Clinical evidence and mechanistic basis for vildagliptin's action when added to metformin. Ahrén, B; Bosi, E; Foley, JE, 2011)	0.37
" AR9281 pharmacokinetic and pharmacodynamic characteristics support a twice-daily or thrice-daily dosing regimen in patients."	( Pharmacokinetics and pharmacodynamics of AR9281, an inhibitor of soluble epoxide hydrolase, in single- and multiple-dose studies in healthy human subjects. Anandan, SK; Chen, D; Do, ZN; Gless, R; MacIntyre, E; Patel, DV; Sabry, J; Tran, V; Webb, HK; Whitcomb, R, 2012)	0.38
" Placebo-adjusted mean change from baseline in QT interval, heart-rate-corrected QT intervals by Fridericia's (QTcF) or Bazett's (QTcB) formula, and PR and QRS intervals were compared at each time-point (time-matched analysis) and for values averaged across the dosing period (time-averaged analysis)."	( Thorough QT study of the effects of vildagliptin, a dipeptidyl peptidase IV inhibitor, on cardiac repolarization and conduction in healthy volunteers. Dole, WP; He, YL; Ligueros-Saylan, M; Serra, D; Wang, Y; Zhang, Y, 2011)	0.37
" Two bioequivalence studies assessed the fed-state bioequivalence of saxagliptin/metformin XR 5 mg/500 mg FDC (study 1) and saxagliptin/metformin XR 5 mg/1000 mg FDC (study 2) relative to the same dosage strengths of individual component tablets administered concurrently."	( Bioequivalence of saxagliptin/metformin extended-release (XR) fixed-dose combination tablets and single-component saxagliptin and metformin XR tablets in healthy adult subjects. Boulton, DW; Huang, J; LaCreta, FP; Li, L; Smith, CH; Tang, A, 2011)	0.37
"Liraglutide has been shown to improve glucose control and weight loss compared to other pharmacologic treatments with diabetes and may offer improved control with a decrease in daily dosing compared to exenatide."	( Place in therapy for liraglutide and saxagliptin for type 2 diabetes. Brock, M; McFarland, MS; Ryals, C, 2011)	0.37
" Furthermore, in patients with higher baseline GA levels, a higher vildagliptin dosage was required to produce a noticeable effect."	( The dipeptidyl peptidase-4 (DPP-4) inhibitor vildagliptin improves glycemic control in type 2 diabetic patients undergoing hemodialysis. Abe, M; Higuchi, T; Ito, M; Kikuchi, F; Maruyama, N; Okada, K; Sasaki, H; Soma, M; Tsuchida, M, 2011)	0.37
" This study examined chronic (once-a-day dosing for 8 weeks) effects of the DPP-4 inhibitor PKF-275-055 (1, 3, and 10mg/kg) on β-cell regeneration and plasma DPP-IV activity, intact GLP-1, glucose, and insulin after an oral glucose load in neonatal wistar rats injected with streptozotocin (STZ) (n2-STZ model), a recognized model of type 2 diabetes."	( A novel long acting DPP-IV inhibitor PKF-275-055 stimulates β-cell proliferation resulting in improved glucose homeostasis in diabetic rats. Akarte, AS; Gandhi, S; Srinivasan, BP, 2012)	0.38
" The objective of this model-based meta-analysis was to describe the time course of HbA1c response after dosing with alogliptin (ALOG), saxagliptin (SAXA), sitagliptin (SITA), or vildagliptin (VILD)."	( Quantitative model of the relationship between dipeptidyl peptidase-4 (DPP-4) inhibition and response: meta-analysis of alogliptin, saxagliptin, sitagliptin, and vildagliptin efficacy results. Barbee, T; Correa, I; Fredrickson, J; Gibbs, JP; Gibbs, MA; Lin, SL; Smith, B, 2012)	0.38
" The present model can be used to predict the effects of other dosage regimens of vildagliptin on DPP-4 inhibition, active GLP-1, glucose and insulin concentrations, or can be modified and applied to other incretin-related anti-diabetes therapies."	( Mechanism-based population modelling of the effects of vildagliptin on GLP-1, glucose and insulin in patients with type 2 diabetes. He, YL; Jusko, WJ; Landersdorfer, CB, 2012)	0.38
" This model can be used to predict DPP-4 inhibition effects of other dosage regimens and be modified for other DPP-4 inhibitors to differentiate their properties."	( Mechanism-based population pharmacokinetic modelling in diabetes: vildagliptin as a tight binding inhibitor and substrate of dipeptidyl peptidase IV. He, YL; Jusko, WJ; Landersdorfer, CB, 2012)	0.38
"A simple, precise and stability-indicating reversed-phase liquid chromatography method was developed and validated for the determination of vildagliptin (VLG) in pharmaceutical dosage form."	( Stability-indicating RP-LC method for the determination of vildagliptin and mass spectrometry detection for a main degradation product. Barden, AT; Salamon, B; Schapoval, EE; Steppe, M, 2012)	0.38
"One hundred seventy-one type 2 diabetes patients, naive to antidiabetes therapy and with poor glycemic control, were instructed to take metformin for 8±2 months up to a mean dosage of 2,500±500 mg/day; then they were randomly assigned to add vildaglipin 50 mg twice a day or placebo for 12 months."	( Vildagliptin added to metformin on β-cell function after a euglycemic hyperinsulinemic and hyperglycemic clamp in type 2 diabetes patients. Bianchi, L; Bonaventura, A; Carbone, A; Cicero, AF; Derosa, G; Fogari, E; Maffioli, P; Ragonesi, PD; Romano, D, 2012)	0.38
" The proposed method could be applied to the determination of AM, MM and RM in dosage forms."	( Determination of adamantane derivatives in pharmaceutical formulations by using spectrophotometric UV-Vis method. Dotka, H; Inerowicz, T; Jelińska, A; Muszalska, I; Rohowska, P; Sobczak, A, 2013)	0.73
" Finally, the rationale for vildagliptin dosing frequency in monotherapy is discussed."	( Evidence to support the use of vildagliptin monotherapy in the treatment of type 2 diabetes mellitus. Dejager, S; Foley, JE; Schweizer, A, 2012)	0.38
" Following dosing for 3 days, accumulation was less than two-fold but steady-state was not achieved."	( First-in-man safety and pharmacokinetics of synthetic ozonide OZ439 demonstrates an improved exposure profile relative to other peroxide antimalarials. Arbe-Barnes, S; Charman, SA; Craft, JC; Duparc, S; Gutierrez, M; Moehrle, JJ; Siethoff, C; van Giersbergen, PL; Vennerstrom, JL; Wittlin, S, 2013)	0.39
") ) of saxagliptin and dapagliflozin using simultaneous intravenous ¹⁴C-microdose/therapeutic oral dosing (i."	( Simultaneous oral therapeutic and intravenous ¹⁴C-microdoses to determine the absolute oral bioavailability of saxagliptin and dapagliflozin. Arnold, ME; Boulton, DW; Christopher, LJ; Kasichayanula, S; Keung, CF; Lacreta, F; Xu, XS, 2013)	0.39
"micro + oraltherap dosing is a valuable tool to assess human absolute bioavailability."	( Simultaneous oral therapeutic and intravenous ¹⁴C-microdoses to determine the absolute oral bioavailability of saxagliptin and dapagliflozin. Arnold, ME; Boulton, DW; Christopher, LJ; Kasichayanula, S; Keung, CF; Lacreta, F; Xu, XS, 2013)	0.39
" When saxagliptin is used in combination with a strong inhibitor of CYP3A4/A5, reduction in the daily dosage is recommended."	( Saxagliptin overview: special focus on safety and adverse effects. Ali, S; Fonseca, V, 2013)	0.39
"Reliable prediction of two fundamental human pharmacokinetic (PK) parameters, systemic clearance (CL) and apparent volume of distribution (Vd), determine the size and frequency of drug dosing and are at the heart of drug discovery and development."	( Quantitative structure-activity relationship models of clinical pharmacokinetics: clearance and volume of distribution. Gombar, VK; Hall, SD, 2013)	0.39
"5 mg/1,000 mg FDC (study 2) relative to the same dosage strengths of the individual component tablets [saxagliptin (Onglyza™) and metformin IR (Glucophage(®))] administered concurrently."	( Bioequivalence of saxagliptin/metformin immediate release (IR) fixed-dose combination tablets and single-component saxagliptin and metformin IR tablets in healthy adult subjects. Boulton, DW; Chang, M; Frevert, EU; Hsiang, BC; Keung, CF; Lacreta, FP; Li, L; Quamina-Edghill, D; Tang, A; Upreti, VV, 2013)	0.39
"A total of 96 subjects were enrolled, and each subject received vildagliptin 50 mg dosed orally once daily for 14 days."	( Pharmacokinetics of vildagliptin in patients with varying degrees of renal impairment. He, YL; Kulmatycki, K; Ligueros-Saylan, M; Reynolds, C; Taylor, A; Zhang, Y; Zhou, W, 2013)	0.39
" The differences in the reductions achieved in FPG and HbA1c with the two dosing regimens were significant."	( Glycemic effects of vildagliptin and metformin combination therapy in Indian patients with type 2 diabetes: an observational study. Chatterjee, S, 2014)	0.4
" In contrast with the goal of maintaining a stable insulin dosage during the short-term phase, during the extension phase the insulin dosage was flexible and adjusted as deemed appropriate by the investigator."	( Saxagliptin add-on therapy to insulin with or without metformin for type 2 diabetes mellitus: 52-week safety and efficacy. Barnett, AH; Charbonnel, B; Donovan, M; Fleming, D; Iqbal, N; Li, J, 2013)	0.39
"A simple, precise and stability-indicating HPLC method was developed and validated for the simultaneous determination of metformin hydrochloride (MET) and vildagliptin (VLG) in pharmaceutical dosage forms."	( Development of validated stability indicating assay method for simultaneous estimation of metformin hydrochloride and vildagliptin by RP-HPLC. Pradeepkumar, M; Rao, VJ; Satheeshkumar, N; Shanthikumar, S, 2014)	0.4
" Compound 40 was dosed to diet-induced obese (DIO) mice and gave excellent target engagement in the liver and high free exposures of drug, both peripherally and in the CNS."	( Optimization of brain penetrant 11β-hydroxysteroid dehydrogenase type I inhibitors and in vivo testing in diet-induced obese mice. Boyd, S; deSchoolmeester, J; Dossetter, AG; Goldberg, FW; Groombridge, SD; Gutierrez, PM; Kemmitt, PD; Robb, GR; Scott, JS; Sjögren, T; Swales, JG; Turnbull, AV; Wild, MJ, 2014)	0.4
" It is dosed orally and can be used safely as monotherapy or in combination with other oral anti-hyperglycemic agents and insulin."	( Vildagliptin, a dipeptidyl peptidase-4 inhibitor, for the treatment of type 2 diabetes. Davis, SN; Lamos, EM; Stein, SA, 2014)	0.4
" The developed methods were satisfactorily applied to analysis of the investigated drugs and proved to be specific and accurate for quality control of them in pharmaceutical dosage forms."	( Validation of different spectrophotometric methods for determination of vildagliptin and metformin in binary mixture. Abdel-Aziz, O; Abdel-Ghany, MF; Ayad, MF; Tadros, MM, 2014)	0.4
"A stability-indicating capillary zone electrophoresis (CZE) method was validated for the determination of vildagliptin (VLG) in pharmaceutical dosage forms using ranitidine hydrochloride (RH) as internal standard."	( Capillary zone electrophoresis for determination of vildagliptin (a DPP-4 inhibitor) in pharmaceutical formulation and comparative study with HPLC. Barden, AT; Piccoli, BL; Schapoval, EE; Steppe, M; Volpato, NM, 2014)	0.4
" This is the first report on the tissue pharmacokinetics of a DPP-4 inhibitor and could contribute to drug dosage optimization in the future."	( Validation of LC-MS/MS method applied to evaluation of free tissue concentrations of vildagliptin in diabetic rats by microdialysis. Costa, TD; de Andrade, C; de Araújo Lock, G; de Araújo, BV; Haas, SE; Pigatto, MC, 2014)	0.4
" It is established that the antidyskinetic effect of the injectable dosage form of a new antiparkinsonian drug hemantane (5 mg/kg) after a single intravenous administration is weaker than that of the most effective in clinical practice antidyskinetic drug amantadine (20 mg/kg)."	( [Influence of hemantane in injectable dosage form on levodopa-induced dyskinesia in rats with model parkinsonian syndrome]. Ivanova, EA; Kapitsa, IG; Kokshenev, II; Nepoklonov, AV; Val'dman, EA; Voronina, TA, 2014)	0.4
" The constructed model would be useful in predicting ABT-384 concentrations at different doses and guiding the selection of dosing regimens in further clinical trials."	( Population pharmacokinetics of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor ABT-384 in healthy volunteers following single and multiple dose regimens. An, G; Awni, W; Dutta, S; Katz, DA; Liu, W; Marek, GJ, 2014)	0.4
" The developed method was validated and proved to be specific and accurate for quality control of SXG in pharmaceutical dosage form."	( Stability-indicating liquid chromatographic method for determination of saxagliptin and structure elucidation of the major degradation products using LC-MS. Abdel-Aziz, O; Abdel-Ghany, MF; Ayad, MF; Tadros, MM, 2015)	0.42
"Simple, selective and reproducible spectrofluorimetric and spectrophotometric methods have been developed for the determination of vildagliptin and saxagliptin in bulk and their pharmaceutical dosage forms."	( Compatible validated spectrofluorimetric and spectrophotometric methods for determination of vildagliptin and saxagliptin by factorial design experiments. Abdel-Aziz, O; Ayad, MF; Tadros, MM, 2015)	0.42
" Five sequential ASP015K cohorts were enrolled, consisting of four twice-daily dosing groups (10, 25, 60, 100 mg) and one once-daily dosing group (50 mg) for 6 weeks."	( A phase 2a randomized, double-blind, placebo-controlled, sequential dose-escalation study to evaluate the efficacy and safety of ASP015K, a novel Janus kinase inhibitor, in patients with moderate-to-severe psoriasis. Akinlade, B; Ball, G; Catlin, M; Krueger, JG; Papp, K; Pariser, D; Wierz, G; Zeiher, B, 2015)	0.42
" Rat biological samples collected after oral dosing of (14)C-labelled ASP015K were examined using a liquid chromatography-radiometric detector and mass spectrometer (LC-RAD/MS)."	( Identification and characterization of metabolites of ASP015K, a novel oral Janus kinase inhibitor, in rats, chimeric mice with humanized liver, and humans. Nakada, N; Oda, K, 2015)	0.42
"0%) with a stable dosage of metformin plus gliclazide for more than 3 months were randomized to receive either vildagliptin 50 mg twice daily (BID, n = 37) or saxagliptin 5 mg once daily (QD, n = 36)."	( Effects of vildagliptin versus saxagliptin on daily acute glucose fluctuations in Chinese patients with T2DM inadequately controlled with a combination of metformin and sulfonylurea. Jing, W; Shunyou, D; Xiaochun, H; Xiaoyan, C; Yingyu, F; Yuyu, T, 2016)	0.43
" After determination of control dose-response functions, mice received 10 mg/kg daily of THC for 7 days, and dose-response functions were re-determined 24 hours, 7 days, or 14 days later."	( Tolerance to the Diuretic Effects of Cannabinoids and Cross-Tolerance to a κ-Opioid Agonist in THC-Treated Mice. Chopda, GR; Gatley, SJ; Makriyannis, A; Parge, V; Paronis, CA; Thakur, GA, 2016)	0.43
" The half-life of plasma DPP-4 inhibition with saxagliptin 5 mg is ~27 h, which supports a once-daily dosing regimen."	( Clinical Pharmacokinetics and Pharmacodynamics of Saxagliptin, a Dipeptidyl Peptidase-4 Inhibitor. Boulton, DW, 2017)	0.46
" This prescribing could have been due to the complexity of different dosing requirements, or a lack of awareness of the need for dose adjustment of most DPP-4 inhibitors in patients with renal impairment."	( Demographic and Clinical Characteristics of Patients With Type 2 Diabetes Mellitus Initiating Dipeptidyl Peptidase 4 Inhibitors: A Retrospective Study of UK General Practice. Bingham-Gardiner, P; Bolodeoku, J; Hassan, SW; Lee, S; Scowcroft, A; Spencer, W; Tebboth, A, 2016)	0.43
" On the basis of the relationship shown, changes in clinical efficacy in association with dose change were examined in order to discuss clinical dosage from the standpoint of proper usage."	( Evaluation of drug efficacy of DPP-4 inhibitors based on theoretical analysis with pharmacokinetics and pharmacodynamics. Kimura, K; Takayanagi, R; Uchida, T; Yamada, Y, 2017)	0.46
" Furthermore, peficitinib dose-dependently suppressed bone destruction and paw swelling in an adjuvant-induced arthritis model in rats via prophylactic or therapeutic oral dosing regimens."	( A novel JAK inhibitor, peficitinib, demonstrates potent efficacy in a rat adjuvant-induced arthritis model. Chida, N; Higashi, Y; Inami, M; Inoue, T; Ito, M; Kuno, M; Morita, Y; Nakamura, K; Okuma, K; Shirakami, S; Yamagami, K; Yamazaki, S, 2017)	0.46
" While generally efficacious, ACTs and the first generation fully synthetic ozonide, arterolane (OZ277, 1), suffer from rapid clearance requiring 3-day dosing regimens."	( Seeking the Elusive Long-Acting Ozonide: Discovery of Artefenomel (OZ439). Guy, RK; Hammill, JT; Kim, HS, 2017)	0.46
"As part of its development, the new synthetic trioxolane antimalarial artefenomel (OZ439) was tested in rat whole embryo culture and in rat embryo-fetal toxicity studies with dosing throughout organogenesis or with a single dose on Gestational Day (GD) 12."	( Improved safety margin for embryotoxicity in rats for the new endoperoxide artefenomel (OZ439) as compared to artesunate. Andenmatten, N; Clark, RL; Clode, SA; Edwards, TL; Huber, AC; Kinney, J; Longo, M; Rhodes, J; Rückle, T; Walker, DK; Wells, T, 2018)	0.48
"To estimate the proportion of patients with moderate to severe chronic kidney disease (CKD) whose initial dipeptidyl-peptidase-4 inhibitor (DPP4-i) dosage was concordant with prescribing information (label) recommendations in the United States."	( Concordance with prescribing information dosage recommendations for dipeptidyl-peptidase-4 inhibitors among type 2 diabetes mellitus patients with moderate to severe chronic kidney disease. Bauer, E; Huang, H; Lang, K; Shetty, S, 2018)	0.48
"9% for saxagliptin and 0% for linagliptin [which does not require dosage adjustment])."	( Concordance with prescribing information dosage recommendations for dipeptidyl-peptidase-4 inhibitors among type 2 diabetes mellitus patients with moderate to severe chronic kidney disease. Bauer, E; Huang, H; Lang, K; Shetty, S, 2018)	0.48
"More than a third of DPP4-i patients with CKD stage 3b or higher were prescribed doses not concordant with DPP4-i label dosage recommendations."	( Concordance with prescribing information dosage recommendations for dipeptidyl-peptidase-4 inhibitors among type 2 diabetes mellitus patients with moderate to severe chronic kidney disease. Bauer, E; Huang, H; Lang, K; Shetty, S, 2018)	0.48
" The resistance issue is further exacerbated by a lack of patient adherence to multi-day dosing regimens."	( Encapsulation of OZ439 into Nanoparticles for Supersaturated Drug Release in Oral Malaria Therapy. Dobrijevic, ELK; Feng, J; Lu, HD; McManus, SA; Mulhearn, WD; Patel, A; Prud'homme, RK; Ramachandruni, H; Ristroph, KD; Zhang, Y, 2018)	0.48
" The primary outcome was peficitinib dose-response at Week 8, with response assessed using Mayo score change from baseline."	( Peficitinib, an Oral Janus Kinase Inhibitor, in Moderate-to-severe Ulcerative Colitis: Results From a Randomised, Phase 2 Study. Bertelsen, K; Feagan, BG; Johanns, J; Lichtenstein, GR; Marano, C; O'Brien, CD; Panes, J; Sandborn, WJ; Sands, BE; Strauss, R; Szapary, P; Vermeire, S; Yang, Z; Zhang, H, 2018)	0.48
"Recently, 2 dipeptidyl peptidase-4 (DPP-4) inhibitors, sitagliptin and saxagliptin, adjusted dosing specification from creatinine clearance to glomerular filtration rate, more typically reported in routine laboratory tests."	( DPP-4 Inhibitor Dose Selection According to Manufacturer Specifications: A Contemporary Experience From UK General Practice. Busse, M; Gollop, ND; Marcus, MW; Spanopoulos, D; Tebboth, A; Webb, J, 2019)	0.51
" Mosquito feeding assays were conducted before artefenomel dosing to investigate parasite transmissibility."	( Antimalarial Activity of Artefenomel Against Asexual Parasites and Transmissible Gametocytes During Experimental Blood-Stage Plasmodium vivax Infection. Abd-Rahman, AN; Ballard, E; Chalon, S; Collins, KA; Gobeau, N; Griffin, P; Marquart, L; McCarthy, JS; Möhrle, JJ, 2022)	0.72
" Serial blood samples were collected for methotrexate concentration after dosing on Days 1 (methotrexate alone) and 8 (methotrexate plus peficitinib) and for peficitinib concentration after dosing on Days 7 (peficitinib alone) and 8 (methotrexate plus peficitinib)."	( Investigation of Potential Drug-Drug Interactions between Peficitinib (ASP015K) and Methotrexate in Patients with Rheumatoid Arthritis. Akinlade, B; Cao, Y; Chindalore, V; Moy, S; Sawamoto, T; Valluri, U; Zhang, W; Zhu, T, 2020)	0.56
" Administration of peficitinib did not result in changes to methotrexate area under the concentration-time curve from time zero to infinity or maximum observed concentration following a methotrexate dose (15-25 mg), and there was no significant effect of methotrexate (15-25 mg) on peficitinib area under the concentration-time curve within a 12-hour dosing interval."	( Investigation of Potential Drug-Drug Interactions between Peficitinib (ASP015K) and Methotrexate in Patients with Rheumatoid Arthritis. Akinlade, B; Cao, Y; Chindalore, V; Moy, S; Sawamoto, T; Valluri, U; Zhang, W; Zhu, T, 2020)	0.56
" Therefore, we designed this updated network meta-analysis to further establish the optimal dosage of peficitinib in treating RA."	( The optimal dosage of pefcitinib for the treatment of active rheumatoid arthritis: A protocol for an updated network meta-analysis. Chen, C; Sun, C; Zhou, Y, 2021)	0.62
"A simple, precise, and rapid stability-indicating reversed-phase-HPLC method was developed and validated for the estimation of metformin (MET), dapagliflozin (DAP), and saxagliptin (SAX) combination in bulk and tablet dosage forms."	( Stability-indicating HPLC method development and validation for simultaneous estimation of metformin, dapagliflozin, and saxagliptin in bulk drug and pharmaceutical dosage form. Alegete, P; Boodida, S; Vankalapati, KR, 2022)	0.72
" For patients with the same degree of renal impairment, rifampicin would have a slightly synergistic effect on the increase of 5-hydroxy saxagliptin exposure compared with dosed alone."	( Physiologically Based Pharmacokinetic Modeling Characterizes the Drug-Drug Interaction Between Saxagliptin and Rifampicin in Patients With Renal Impairment. Ke, M; Lin, C; Lin, R; Wu, W; Ye, L, 2023)	0.91

Class	Description
polycyclic alkane	A polycyclic saturated hydrocarbon.
adamantanes	Compounds containing an adamantane skeleton.
[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]

Assay ID	Title	Year	Journal	Article
AID603957	Octanol-water partition coefficient, log P of the compound	2008	European journal of medicinal chemistry, Apr, Volume: 43, Issue:4	QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.
AID1816797	Antiproliferative activity against human MDA-MB-468 cells expressing p53 R273H mutant assessed as inhibition of cell growth at 10 to 50 uM incubated for 24 to 72 hrs by WST-1 assay	2021	Journal of medicinal chemistry, 05-27, Volume: 64, Issue:10	Adamantyl Isothiocyanates as Mutant p53 Rescuing Agents and Their Structure-Activity Relationships.
AID1816759	Antiproliferative activity against human MCF7 cells expressing WT p53 assessed as inhibition of cell growth at 10 to 50 uM incubated for 24 to 72 hrs by WST-1 assay	2021	Journal of medicinal chemistry, 05-27, Volume: 64, Issue:10	Adamantyl Isothiocyanates as Mutant p53 Rescuing Agents and Their Structure-Activity Relationships.
AID1816754	Antiproliferative activity against human MDA-MB-231 cells expressing p53 R280K mutant assessed as inhibition of cell growth at 10 to 50 uM incubated for 24 to 72 hrs by WST-1 assay	2021	Journal of medicinal chemistry, 05-27, Volume: 64, Issue:10	Adamantyl Isothiocyanates as Mutant p53 Rescuing Agents and Their Structure-Activity Relationships.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	254 (7.86)	18.7374
1990's	243 (7.52)	18.2507
2000's	777 (24.04)	29.6817
2010's	1676 (51.86)	24.3611
2020's	282 (8.73)	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	360 (10.44%)	5.53%
Reviews	314 (9.10%)	6.00%
Case Studies	35 (1.01%)	4.05%
Observational	26 (0.75%)	0.25%
Other	2,714 (78.69%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
ethylene dichloride ethylene dichloride: RN given refers to 1,2-isomer; structure given in first source. 1,2-dichloroethane : A member of the class of chloroethanes substituted by two chloro groups at positions 1 and 2.	2.04	1	0	chloroethanes	hepatotoxic agent; mutagen; non-polar solvent
1,2,4-trichlorobenzene 1,2,4-trichlorobenzene : A trichlorobenzene with chloro substituents at positions 1, 2 and 4.	2.04	1	0	trichlorobenzene
phosphoserine Phosphoserine: The phosphoric acid ester of serine.	2.11	1	0	non-proteinogenic alpha-amino acid; O-phosphoamino acid; serine derivative	human metabolite
n-carbamoyl-beta-alanine N-carbamoyl-beta-alanine: RN given refers to parent cpd. N-carbamoyl-beta-alanine : A beta-alanine derivative that is propionic acid bearing a ureido group at position 3.	2.13	1	0	beta-alanine derivative	metabolite; mouse 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.	4.83	10	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
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.	2.13	1	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.	2.99	4	0	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
adenine [no description available]	4.5	5	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	2.03	1	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
beta-alanine [no description available]	2.13	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
benzene [no description available]	8.13	5	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.	2.13	1	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
betaine glycine betaine : The amino acid betaine derived from glycine.	7.25	1	0	amino-acid betaine; glycine derivative	fundamental metabolite
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)	2.49	2	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.	2.13	1	0	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
cadaverine [no description available]	2.4	2	0	alkane-alpha,omega-diamine	Daphnia magna metabolite; Escherichia coli metabolite; mouse metabolite; plant metabolite
carbamates [no description available]	4.8	7	1	amino-acid anion
carbamic acid carbamic acid : A one-carbon compound that is ammonia in which one of the hydrogens is replaced by a carboxy group. Although carbamic acid derivatives are common, carbamic acid itself has never been synthesised.	2.03	1	0	carbon oxoacid; one-carbon compound; organonitrogen compound	Escherichia coli metabolite
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.	2.44	2	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
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).	9.86	10	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	7.39	2	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.96	4	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.	2.01	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse 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.	3	4	0	alkane	xenobiotic
phloroglucinol Phloroglucinol: A trinitrobenzene derivative with antispasmodic properties that is used primarily as a laboratory reagent.. phloroglucinol : A benzenetriol with hydroxy groups at position 1, 3 and 5.	3.7	9	0	benzenetriol; phenolic donor	algal 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.	2.67	3	0	aryl phosphate	mouse metabolite
hydrogen sulfide Hydrogen Sulfide: A flammable, poisonous gas with a characteristic odor of rotten eggs. It is used in the manufacture of chemicals, in metallurgy, and as an analytical reagent. (From Merck Index, 11th ed). hydrogen sulfide : A sulfur hydride consisting of a single sulfur atom bonded to two hydrogen atoms. A highly poisonous, flammable gas with a characteristic odour of rotten eggs, it is often produced by bacterial decomposition of organic matter in the absence of oxygen.. thiol : An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.	2.08	1	0	gas molecular entity; hydracid; mononuclear parent hydride; sulfur hydride	Escherichia coli metabolite; genotoxin; metabolite; signalling molecule; toxin; vasodilator agent
n(g),n(g')-dimethyl-l-arginine N,N-dimethylarginine: asymmetric dimethylarginine; do not confuse with N,N'-dimethylarginine	3.48	1	1	alpha-amino acid
phosphonoacetic acid Phosphonoacetic Acid: A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.. phosphonoacetic acid : A member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.	1.95	1	0	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
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.	2.04	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
cytosine [no description available]	7.78	3	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.47	2	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna 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.	2.91	4	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glutaric acid glutaric acid: RN given refers to parent cpd. glutaric acid : An alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid.	2.13	1	0	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	Daphnia magna metabolite; human metabolite
glycine [no description available]	11.42	12	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.	2.77	3	0	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
histamine [no description available]	3.24	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.	9.71	6	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.98	4	0	imidazole
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..	7.77	3	0	diatomic iodine	nutrient
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.	2.49	2	0	dithiolanes; heterocyclic fatty acid; thia fatty acid	fundamental metabolite; geroprotector
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.46	2	0	alpha,omega-dicarboxylic acid	human metabolite
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.	2.15	1	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
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.	5.99	3	3	cyclitol; hexol
melatonin [no description available]	2.1	1	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
naphthalene [no description available]	2.46	2	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.	2.17	1	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.	17.06	70	21	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
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	7.92	4	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
nitric acid Nitric Acid: Nitric acid (HNO3). A colorless liquid that is used in the manufacture of inorganic and organic nitrates and nitro compounds for fertilizers, dye intermediates, explosives, and many different organic chemicals. Continued exposure to vapor may cause chronic bronchitis; chemical pneumonitis may occur. (From Merck Index, 11th ed). nitric acid : A nitrogen oxoacid of formula HNO3 in which the nitrogen atom is bonded to a hydroxy group and by equivalent bonds to the remaining two oxygen atoms.	3.13	1	0	nitrogen oxoacid	protic solvent; reagent
nitroxyl nitroxyl: hydroxamic acid oxidized to nitroxyl free radical. nitroxyl : A nitrogen oxoacid consisting of an oxygen atom double-bonded to an NH group.	3.29	6	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)	2.07	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
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.	2.44	2	0	octanol; primary alcohol	antifungal agent; bacterial metabolite; fuel additive; kairomone; plant metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2.04	1	0	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
oxamic acid Oxamic Acid: Amino-substituted glyoxylic acid derivative.. oxamic acid : A dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia.	1.95	1	0	dicarboxylic acid monoamide	Escherichia coli 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.	2.04	1	0	aminobenzoic acid; aromatic amino-acid zwitterion	allergen; Escherichia coli metabolite; plant metabolite
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.	2.31	1	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
phenanthrene phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'	2.46	2	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon; phenanthrenes	environmental contaminant; mouse metabolite
phosphorylcholine Phosphorylcholine: Calcium and magnesium salts used therapeutically in hepatobiliary dysfunction.. phosphocholine : The phosphate of choline; and the parent compound of the phosphocholine family.	3.05	4	0	phosphocholines	allergen; epitope; hapten; human metabolite; mouse 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.	2.03	1	0	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.	1.98	1	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
putrescine [no description available]	2.11	1	0	alkane-alpha,omega-diamine	antioxidant; fundamental metabolite
pyrazinamide pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.	10.04	9	4	monocarboxylic acid amide; N-acylammonia; pyrazines	antitubercular agent; prodrug
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	8	4	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.7	3	0	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfide dimethyl sulfide: structure. dimethyl sulfide : A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.. methyl sulfide : Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group.	2.04	1	0	aliphatic sulfide	algal metabolite; bacterial xenobiotic metabolite; EC 3.5.1.4 (amidase) inhibitor; Escherichia coli metabolite; marine 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).	7.49	2	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion
spermine [no description available]	2.97	4	0	polyazaalkane; tetramine	antioxidant; fundamental metabolite; immunosuppressive agent
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.	2.04	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.74	3	0	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	12.71	54	2	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
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.	2.15	1	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.	12.49	37	1	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	2.44	2	0	xanthine	Saccharomyces cerevisiae metabolite
2-amino-5-phosphonovalerate 2-Amino-5-phosphonovalerate: The D-enantiomer is a potent and specific antagonist of NMDA glutamate receptors (RECEPTORS, N-METHYL-D-ASPARTATE). The L form is inactive at NMDA receptors but may affect the AP4 (2-amino-4-phosphonobutyrate; APB) excitatory amino acid receptors.	2.47	2	0	non-proteinogenic alpha-amino acid	NMDA receptor antagonist
sk&f 81297 [no description available]	2.69	3	0	benzazepine
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	2.4	2	0	phenols; tertiary amino compound; tetralins	serotonergic antagonist
alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid: An IBOTENIC ACID homolog and glutamate agonist. The compound is the defining agonist for the AMPA subtype of glutamate receptors (RECEPTORS, AMPA). It has been used as a radionuclide imaging agent but is more commonly used as an experimental tool in cell biological studies.	2.73	3	0	non-proteinogenic alpha-amino acid
sk&f 82958 [no description available]	2.41	2	0	benzazepine
4-iodo-2,5-dimethoxyphenylisopropylamine 4-iodo-2,5-dimethoxyphenylisopropylamine: RN given refers to unlabeled parent cpd without isomeric designation; a serotonin agonist. 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine : An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.	2.05	1	0	amphetamines; dimethoxybenzene; organoiodine compound
gallopamil Gallopamil: Coronary vasodilator that is an analog of iproveratril (VERAPAMIL) with one more methoxy group on the benzene ring.	1.98	1	0	benzenes; organic amino compound
sk&f-38393 2,3,4,5-Tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine: A selective D1 dopamine receptor agonist used primarily as a research tool.. 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1 and two hydroxy substituents at positions 7 and 8.. SKF 38393 : A racemate comprising equimolar amounts of (R)- and (S)-SKF 38393	2.68	3	0	benzazepine; catechols; secondary amino compound
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.15	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
1,3-dipropyl-8-cyclopentylxanthine DPCPX : An oxopurine that is 7H-xanthine substituted at positions 1 and 3 by propyl groups and at position 8 by a cyclohexyl group.	2.41	2	0	oxopurine	adenosine A1 receptor antagonist; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
1-aminocyclohexanecarboxylic acid 1-aminocyclohexanecarboxylic acid: RN given refers to parent cpd. 1-amino-1-cyclohexanecarboxylic acid : An alpha-amino acid that is cyclohexanecarboxylic acid substituted by an amino group at position 1.	2.02	1	0	alpha-amino acid
1-aminobenzotriazole [no description available]	2.03	1	0
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.	2.79	3	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.	3.81	11	0	methylpyridines; phenylpyridine; tetrahydropyridine	neurotoxin
14,15-epoxy-5,8,11-eicosatrienoic acid 14,15-epoxy-5,8,11-eicosatrienoic acid: RN given refers to cpd without isomeric designation	3.49	7	0	long-chain fatty acid
1h-(1,2,4)oxadiazolo(4,3-a)quinoxalin-1-one 1H-(1,2,4)oxadiazolo(4,3-a)quinoxalin-1-one: structure given in first source; inhibits guanylyl cyclase. 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one : A member of the class of oxadiazoloquinoxalines that is 1H-[1,2,4]oxadiazolo[4,3-a]quinoxaline substituted at position 1 by an oxo group.	2.42	2	0	oxadiazoloquinoxaline	EC 4.6.1.2 (guanylate cyclase) inhibitor
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'.	2.15	1	0	bipyridine	chelator; ferroptosis inhibitor
pyrithione pyrithione: split from cephalosporin molecule; some metal complexes of this have fumarate reductase inhibitory activity and may be useful against trypanosomes; RN given refers to parent cpd; structure. pyrithione : A pyridinethione that is pyridine-2(1H)-thione in which the hydrogen attached to the nitrogen is replaced by a hydroxy group. It is a Zn(2+) ionophore; the zinc salt is used as an antifungal and antibacterial agent.	2.21	1	0	monohydroxypyridine; pyridinethione	ionophore
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.	2.04	1	0	benzodioxoles
3-hydroxybenzylhydrazine 3-hydroxybenzylhydrazine: decarboxylase inhibitor; RN given refers to parent cpd; structure	2.05	1	0	phenols
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.95	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
4-amino-1,8-naphthalimide 4-amino-1,8-naphthalimide: inhibits ADP-ribosylation; sometimes abreviated as 4-AN;	2.05	1	0	benzoisoquinoline; dicarboximide
phenytoin [no description available]	2.4	2	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
5-carboxamidotryptamine 5-carboxamidotryptamine: agonist of 5-HT receptor; structure given in first source	2.39	2	0	tryptamines
5-hydroxydecanoate 5-hydroxydecanoic acid: Potassium Channel Blocker; RN refers to parent cpd	2.05	1	0	medium-chain fatty acid
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.	1.95	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
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.	7.21	1	0	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor
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.	5.9	3	3	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
tyrphostin ag957 tyrphostin AG957: tyrosine kinase blocker; structure given in first source	2.41	2	0	aromatic amine
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.	3.16	5	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	13.49	75	7	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.1	1	0	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
theophylline [no description available]	7.48	2	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
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.	3.43	1	1	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent
amodiaquine Amodiaquine: A 4-aminoquinoline compound with anti-inflammatory properties.. amodiaquine : A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.	2.07	1	0	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug
aniracetam [no description available]	2	1	0	N-acylpyrrolidine; pyrrolidin-2-ones
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.	2.03	1	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
arcaine arcaine: RN given refers to parent cpd; structure. 1,4-diguanidinobutane : A guanidine derivative consisting of butane having guanidino groups at the 1- and 4-positions.	2.04	1	0	guanidines
arecoline Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.	2.04	1	0	enoate ester; methyl ester; pyridine alkaloid; tetrahydropyridine	metabolite; muscarinic agonist
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.	2.67	3	0	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
baclofen [no description available]	2.07	1	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.	2.41	2	0	(trifluoromethyl)benzenes; C-nitro compound; dihydropyridine; methyl ester
benserazide Benserazide: An inhibitor of DOPA DECARBOXYLASE that does not enter the central nervous system. It is often given with LEVODOPA in the treatment of parkinsonism to prevent the conversion of levodopa to dopamine in the periphery, thereby increasing the amount that reaches the central nervous system and reducing the required dose. It has no antiparkinson actions when given alone.. benserazide : A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.	2.46	2	0	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor
benzamide benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.	2.05	1	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.	2.04	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mouse metabolite
berberine [no description available]	2.41	1	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
bisacodyl Bisacodyl: A diphenylmethane stimulant laxative used for the treatment of CONSTIPATION and for bowel evacuation. (From Martindale, The Extra Pharmacopoeia, 30th ed, p871)	1.98	1	0	diarylmethane
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.	2.69	3	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
caffeine [no description available]	2.06	1	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.	4.65	6	1	aromatic ether; nitrile; polyether; tertiary amino compound
camphor, (+-)-isomer [no description available]	3.87	12	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
candesartan candesartan: a nonpeptide angiotensin II receptor antagonist. candesartan : A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin receptor antagonist used for the treatment of hypertension.	2	1	0	benzimidazolecarboxylic acid; biphenylyltetrazole	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
cannabinol Cannabinol: A physiologically inactive constituent of Cannabis sativa L.	3.2	5	0	dibenzopyran
carbonyl cyanide m-chlorophenyl hydrazone Carbonyl Cyanide m-Chlorophenyl Hydrazone: A proton ionophore. It is commonly used as an uncoupling agent and inhibitor of photosynthesis because of its effects on mitochondrial and chloroplast membranes.. CCCP : A member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death.	2.1	1	0	hydrazone; monochlorobenzenes; nitrile	antibacterial agent; geroprotector; ionophore
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.	1.99	1	0	quaternary ammonium ion
cgs 15943 9-chloro-2-(2-furyl)-(1,2,4)triazolo(1,5-c)quinazolin-5-imine: non-xanthine triazoloquinazoline adenosine antagonist. CGS 15943 : A member of the class of triazoloquinazolines that is [1,2,4]triazolo[1,5-c]quinazoline substited at positions 2, 5 and 9 by furan-2-yl, amino and chloro groups respectively. A potent antagonist at adenosine A1 and adenosine A2A receptors.	1.98	1	0	aromatic amine; biaryl; furans; organochlorine compound; primary amino compound; quinazolines; triazoloquinazoline	adenosine A1 receptor antagonist; adenosine A2A receptor antagonist; antineoplastic agent; central nervous system stimulant
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.	5.77	7	1	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
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.	3.34	1	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.	1.96	1	0	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
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.	2.08	1	0	1,3-benzoxazoles; heteroaryl hydroxy compound; organochlorine compound	muscle relaxant; sedative
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.	2.38	2	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
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.	2.41	1	0	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.	1.99	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.	2.13	1	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
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	1.95	1	0	aromatic ether; ethyl ester; monochlorobenzenes	anticholesteremic drug; antilipemic drug; geroprotector; PPARalpha agonist
cyclothiazide cyclothiazide: inhibits the desensitization of AMPA-type receptors; structure. cyclothiazide : 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide substituted at positions 3, 5 and 6 by a 2-norbornen-5-yl group, chlorine, and a sulfonamide group, respectively. A thiazide diuretic, it has been used in the management of hypertension and oedema.	2.4	2	0	benzothiadiazine	antihypertensive agent; diuretic
dapsone [no description available]	2.08	1	0	substituted aniline; sulfone	anti-inflammatory drug; antiinfective agent; antimalarial; leprostatic drug
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.	2.47	2	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
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.	8.39	7	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.	2.72	3	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; 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.	2.04	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
diphenhydramine Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.	2.89	4	0	ether; tertiary amino compound	anti-allergic agent; antidyskinesia agent; antiemetic; antiparkinson drug; antipruritic drug; antitussive; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; oneirogen; sedative
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.	1.98	1	0	piperidines; pyrimidopyrimidine; tertiary amino compound; tetrol	adenosine phosphodiesterase inhibitor; EC 3.5.4.4 (adenosine deaminase) inhibitor; platelet aggregation inhibitor; vasodilator agent
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.08	1	0	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
racemetirosine alpha-Methyltyrosine: An inhibitor of the enzyme TYROSINE 3-MONOOXYGENASE, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with PHEOCHROMOCYTOMA. (Martindale, The Extra Pharmacopoeia, 30th ed)	2	1	0
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.	4.4	1	1	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
droperidol Droperidol: A butyrophenone with general properties similar to those of HALOPERIDOL. It is used in conjunction with an opioid analgesic such as FENTANYL to maintain the patient in a calm state of neuroleptanalgesia with indifference to surroundings but still able to cooperate with the surgeon. It is also used as a premedicant, as an antiemetic, and for the control of agitation in acute psychoses. (From Martindale, The Extra Pharmacopoeia, 29th ed, p593). droperidol : An organofluorine compound that is haloperidol in which the hydroxy group has been eliminated with the introduction of a double bond in the piperidine ring, and the 4-chlorophenyl group has been replaced by a benzimidazol-2-on-1-yl group. It is used in the management of chemotherapy-induced nausea and vomiting, and in conjunction with an opioid analgesic such as fentanyl to maintain the patient in a calm state of neuroleptanalgesia with indifference to surroundings but still able to cooperate with the surgeon.	1.96	1	0	aromatic ketone; benzimidazoles; organofluorine compound	anaesthesia adjuvant; antiemetic; dopaminergic antagonist; first generation antipsychotic
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.	2.94	4	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.	2.13	1	0	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
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.	2.52	2	0	alkane-alpha,omega-diamine	GABA agonist
famotidine Famotidine: A competitive histamine H2-receptor antagonist. Its main pharmacodynamic effect is the inhibition of gastric secretion.	3.59	1	1	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
fenfluramine Fenfluramine: A centrally active drug that apparently both blocks serotonin uptake and provokes transport-mediated serotonin release.. fenfluramine : A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.	2.15	1	0	(trifluoromethyl)benzenes; secondary amino compound	appetite depressant; serotonergic agonist; serotonin uptake inhibitor
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	2.03	1	0	aromatic ether; chlorobenzophenone; isopropyl ester; monochlorobenzenes	antilipemic drug; environmental contaminant; geroprotector; xenobiotic
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.	2.48	2	0	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
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
fluphenazine [no description available]	1.95	1	0	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.01	1	0	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
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.	2.06	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.	2.96	4	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.	2.54	2	0	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
foscarnet Foscarnet: An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV.. phosphonoformic acid : Phosphoric acid in which one of the hydroxy groups is replaced by a carboxylic acid group. It is used as the trisodium salt as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.	3.11	1	0	carboxylic acid; one-carbon compound; phosphonic acids	antiviral drug; geroprotector; HIV-1 reverse transcriptase inhibitor; sodium-dependent Pi-transporter 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.	2.91	4	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.	8.54	2	0	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic
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.	2.59	2	0
gliclazide Gliclazide: An oral sulfonylurea hypoglycemic agent which stimulates insulin secretion.	9.05	10	5	N-sulfonylurea	hypoglycemic agent; insulin secretagogue; radical scavenger
glimepiride glimepiride: structure given in first source	14.23	32	28	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.	8.77	9	6	aromatic amide; monocarboxylic acid amide; N-sulfonylurea; pyrazines	EC 2.7.1.33 (pantothenate kinase) inhibitor; hypoglycemic agent; insulin secretagogue
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.	13.35	33	12	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
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.	1.95	1	0
guaifenesin Guaifenesin: An expectorant that also has some muscle relaxing action. It is used in many cough preparations.	3.35	1	1	methoxybenzenes
guanfacine Guanfacine: A centrally acting antihypertensive agent with specificity towards ADRENERGIC ALPHA-2 RECEPTORS.	4.04	1	0	acetamides
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.	3.1	5	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.	3.11	5	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
miltefosine miltefosine: hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin. miltefosine : A phospholipid that is the hexadecyl monoester of phosphocholine.	2.57	2	0	phosphocholines; phospholipid	anti-inflammatory agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antiprotozoal drug; apoptosis inducer; immunomodulator; protein kinase inhibitor
hexahydrosiladifenidol [no description available]	1.97	1	0
alpha-methylhistamine alpha-methylhistamine: a histamine H3 receptor agonist; RN given refers to parent cpd without isomeric designation. alpha-methylhistamine : An aralkylamino compound that is histamine bearing a methyl substituent at the alpha-position.	2.02	1	0	aralkylamino compound; imidazoles	animal metabolite; H3-receptor agonist
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.	4.45	1	1	aminoquinoline; organochlorine compound; primary alcohol; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; dermatologic drug
hydroxyurea [no description available]	2.31	1	0	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	4.39	4	1	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
ifenprodil ifenprodil: NMDA receptor antagonist	2.08	1	0	piperidines
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.	2.73	3	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.	2.96	4	0	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
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	2.1	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).	9.9	10	4	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.	2.15	1	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.	3.26	6	0	catechols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; cardiotonic drug; sympathomimetic agent
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.	4.7	4	0	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2	1	0	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
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.	2.43	2	0	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine
kojic acid [no description available]	2.07	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
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	2.07	1	0	chromones; morpholines; organochlorine compound	autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector
edaravone [no description available]	7.6	1	0	pyrazolone	antioxidant; radical scavenger
mecamylamine Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.	2.44	2	0	primary aliphatic amine
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.	3.79	11	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
memantine [no description available]	12.58	17	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.	2.44	2	0	1,4-naphthoquinones; vitamin K	angiogenesis inhibitor; antineoplastic agent; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; human urinary metabolite; nutraceutical
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.	22.06	243	140	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
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.	2.48	2	0	polyazaalkane; polycyclic cage; tetramine	antibacterial drug
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
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.	2.08	1	0	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic
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.	2.03	1	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.	2.13	1	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
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.	2.67	3	0	dialkylarylamine; tertiary amino compound
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.	1.95	1	0	diarylmethane
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.	1.96	1	0	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent
entinostat [no description available]	2.17	1	0	benzamides; carbamate ester; primary amino compound; pyridines; substituted aniline	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
muscimol Muscimol: A neurotoxic isoxazole isolated from species of AMANITA. It is obtained by decarboxylation of IBOTENIC ACID. Muscimol is a potent agonist of GABA-A RECEPTORS and is used mainly as an experimental tool in animal and tissue studies.. muscimol : A member of the class of isoxazoles that is 1,2-oxazol-3(2H)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus Amanita.	2.17	1	0	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug
1,3-dicyclohexylurea 1,3-dicyclohexylurea: degradation product of 1-(2-chloroethyl)-3- cyclohexyl-1-nitrosourea; structure	2	1	0	ureas
nan 190 1-(2-methoxyphenyl)-4-(4-(2-phthalimido)butyl)piperazine: RN from Toxlit. NAN 190 : An N-alkylpiperazine that consists of (2-methoxyphenyl)piperazine in which the amine hydrogen is substituted by a 4-(2-phthalimido)butyl group.	2.4	2	0	N-alkylpiperazine; N-arylpiperazine; phthalimides	serotonergic antagonist
activins Activins: Activins are produced in the pituitary, gonads, and other tissues. By acting locally, they stimulate pituitary FSH secretion and have diverse effects on cell differentiation and embryonic development. Activins are glycoproteins that are hetero- or homodimers of INHIBIN-BETA SUBUNITS.	2.17	1	0
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.	2.39	2	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
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.	2.52	2	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
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
nitromide nitromide: antibacterial agent for prevention & treatment of Salmonella pullorum infections in chickens & turkeys & for fowl typhoid & paratyphoid; used in feed; structure	3.23	1	0
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.	3.59	1	1	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.	3.5	1	1	carbazoles
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).	3.82	11	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
oxymetazoline Oxymetazoline: A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251). oxymetazoline : A member of the class of phenols that is 2,4-dimethylphenol which is substituted at positions 3 and 6 by 4,5-dihydro-1H-imidazol-2-ylmethyl and tert-butyl groups, respectively. A direct-acting sympathomimetic with marked alpha-adrenergic activity, it is a vasoconstrictor that is used (generally as the hydrochloride salt) to relieve nasal congestion.	2.15	1	0	carboxamidine; imidazolines; phenols	alpha-adrenergic agonist; nasal decongestant; sympathomimetic agent; vasoconstrictor 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).	2.11	1	0	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
4-dichlorobenzene dichlorobenzene : Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.. 1,4-dichlorobenzene : A dichlorobenzene carrying chloro groups at positions 1 and 4.	2.04	1	0	dichlorobenzene	insecticide
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'.	2.03	1	0	aromatic amine; monomethoxyflavone	EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; geroprotector
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.	2.44	2	0	barbiturates	GABAA receptor agonist
pentoxifylline [no description available]	3.5	1	1	oxopurine
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.	1.97	1	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.	1.96	1	0	phenols
phenyl biguanide phenyl biguanide: RN given refers to parent cpd. phenyl biguanide : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a phenyl group.	2.08	1	0	guanidines	central nervous system drug
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)	3.26	6	0	pyridines
pioglitazone Pioglitazone: A thiazolidinedione and PPAR GAMMA agonist that is used in the treatment of TYPE 2 DIABETES MELLITUS.. pioglitazone : A member of the class of thiazolidenediones that is 1,3-thiazolidine-2,4-dione substituted by a benzyl group at position 5 which in turn is substituted by a 2-(5-ethylpyridin-2-yl)ethoxy group at position 4 of the phenyl ring. It exhibits hypoglycemic activity.	16	43	11	aromatic ether; pyridines; thiazolidinediones	antidepressant; cardioprotective agent; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; geroprotector; hypoglycemic agent; insulin-sensitizing drug; PPARgamma agonist; xenobiotic
piperazine [no description available]	2.11	1	0	azacycloalkane; piperazines; saturated organic heteromonocyclic parent	anthelminthic drug
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	2.13	1	0	organonitrogen compound; organooxygen compound
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.	2.89	4	0	pyridobenzodiazepine	anti-ulcer drug; antispasmodic drug; muscarinic antagonist
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.	1.95	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.	3.11	5	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.	1.99	1	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid pyridoxal phosphate-6-azophenyl-2',4'-disulfonic acid: a novel antagonist that selectively blocks P2 purinoceptor receptors; a useful tool to study co-transmission in tissues when ATP and coexisting neurotransmitters act in concert. 5'-phosphopyridoxal-6-azobenzene-2,4-disulfonic acid : An arenesulfonic acid that is pyridoxal 5'-phosphate carrying an additional 2,4-disulfophenylazo substituent at position 6.	2	1	0	arenesulfonic acid; azobenzenes; methylpyridines; monohydroxypyridine; organic phosphate; pyridinecarbaldehyde	purinergic receptor P2X antagonist
praziquantel azinox: Russian drug	2.46	2	0	isoquinolines
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.	6.42	4	2	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
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.	2.04	1	0	benzoate ester; substituted aniline; tertiary amino compound	central nervous system depressant; drug allergen; local anaesthetic; peripheral nervous system drug
proglumide Proglumide: A drug that exerts an inhibitory effect on gastric secretion and reduces gastrointestinal motility. It is used clinically in the drug therapy of gastrointestinal ulcers.. proglumide : A racemate composed of equal amounts of (R)- and (S)-proglumide. A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs.. N(2)-benzoyl-N,N-dipropyl-alpha-glutamine : A dicarboxylic acid monoamide obtained by formal condensation of the alpha-carboxy group of N-benzoylglutamic acid with dippropylamine.	2	1	0	benzamides; dicarboxylic acid monoamide; glutamine derivative; racemate	anti-ulcer drug; cholecystokinin antagonist; cholinergic antagonist; delta-opioid receptor agonist; drug metabolite; gastrointestinal drug; opioid analgesic; xenobiotic metabolite
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.	2.55	2	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.	2	1	0	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.	2.38	2	0	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
protoporphyrin ix protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685. protoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.	2.31	1	0
pyrilamine Pyrilamine: A histamine H1 antagonist. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.. mepyramine : An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.	1.99	1	0	aromatic ether; ethylenediamine derivative	H1-receptor antagonist
pyrimethamine Maloprim: contains above 2 cpds	1.96	1	0	aminopyrimidine; monochlorobenzenes	antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor
riluzole Riluzole: A glutamate antagonist (RECEPTORS, GLUTAMATE) used as an anticonvulsant (ANTICONVULSANTS) and to prolong the survival of patients with AMYOTROPHIC LATERAL SCLEROSIS.	2.6	1	0	benzothiazoles
rimantadine Rimantadine: An RNA synthesis inhibitor that is used as an antiviral agent in the prophylaxis and treatment of influenza.	19.42	119	18	alkylamine
ritanserin Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.	1.98	1	0	organofluorine compound; piperidines; thiazolopyrimidine	antidepressant; antipsychotic agent; anxiolytic drug; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
rolipram [no description available]	2.72	3	0	pyrrolidin-2-ones	antidepressant; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
ropinirole [no description available]	2.15	1	0	indolones; tertiary amine	antidyskinesia agent; antiparkinson drug; central nervous system drug; dopamine agonist
carbamylhydrazine carbamylhydrazine: RN given refers to parent cpd	2.02	1	0	carbohydrazide; monocarboxylic acid amide; one-carbon compound; ureas
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.	2.15	1	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).	4.23	3	1	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) 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.	2.15	1	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
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.	4.45	1	1
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.	2.01	1	0	benzamides; N-alkylpyrrolidine; sulfonamide	antidepressant; antiemetic; antipsychotic agent; dopaminergic antagonist
temozolomide [no description available]	2.6	1	0	imidazotetrazine; monocarboxylic acid amide; triazene derivative	alkylating agent; antineoplastic agent; prodrug
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.	1.97	1	0	benzoate ester; tertiary amino compound	local anaesthetic
tetraethylammonium Tetraethylammonium: A potassium-selective ion channel blocker. (From J Gen Phys 1994;104(1):173-90)	1.99	1	0	quaternary ammonium ion
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.	4.36	3	0	phthalimides; piperidones
2,4-thiazolidinedione thiazolidine-2,4-dione: structure in first source. 1,3-thiazolidine-2,4-dione : A thiazolidenedione carrying oxo substituents at positions 2 and 4.	10.09	10	7	thiazolidenedione
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.	2.08	1	0	N-sulfonylurea	human metabolite; hypoglycemic agent; insulin secretagogue; potassium channel blocker
triclosan [no description available]	2.15	1	0	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
trigonelline trigonelline: in hydra among other organisms; RN given refers to hydroxide inner salt; structure. N-methylnicotinic acid : A pyridinium ion consisting of nicotinic acid having a methyl substituent on the pyridine nitrogen.. N-methylnicotinate : An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.	2.15	1	0	alkaloid; iminium betaine	food component; human urinary metabolite; plant metabolite
troglitazone Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.	2.41	2	0	chromanes; thiazolidinone	anticoagulant; anticonvulsant; antineoplastic agent; antioxidant; EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; hypoglycemic agent; platelet aggregation inhibitor; vasodilator agent
8-(4-((2-aminoethyl)aminocarbonylmethyloxy)phenyl)-1,3-dipropylxanthine 8-(4-((2-aminoethyl)aminocarbonylmethyloxy)phenyl)-1,3-dipropylxanthine: adenosine receptor antagonist	1.99	1	0
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.	3.63	2	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
lysergic acid diethylamide Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.	2.13	1	0	ergoline alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound	dopamine agonist; hallucinogen; serotonergic agonist
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.	2.37	2	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
phentolamine Phentolamine: A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.. phentolamine : A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used for the treatment of hypertension.	2.9	4	0	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.03	1	0	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
thymidine [no description available]	2.4	2	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.31	1	0	benzimidazole; polycyclic heteroarene
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.	2.4	2	0	1-phenylpropan-2-amine	adrenergic agent; adrenergic uptake inhibitor; dopamine uptake inhibitor; dopaminergic agent; neurotoxin; sympathomimetic agent
pentolinium tartrate Pentolinium Tartrate: A nicotinic antagonist that has been used as a ganglionic blocking agent in hypertension.. pentolinium tartrate : The bitartrate salt of pentolinium.	2.07	1	0	tartrate salt	antihypertensive agent
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.72	3	0	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.	2.15	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
1,2,5,6-dibenzanthracene 1,2,5,6-dibenzanthracene: RN given refers to parent cpd	2.04	1	0	ortho-fused polycyclic arene	mutagen
azauridine Azauridine: A triazine nucleoside used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic.	1.96	1	0	N-glycosyl-1,2,4-triazine	antimetabolite; antineoplastic agent; drug metabolite
idoxuridine [no description available]	1.95	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.	2.86	3	0	pilocarpine	antiglaucoma drug
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	2.02	1	0	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
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.	3.19	5	0	organic heterobicyclic compound; organonitrogen heterocyclic compound
biguanides Biguanides: Derivatives of biguanide (the structure formula HN(C(NH)NH2)2) that are primarily used as oral HYPOGLYCEMIC AGENTS for the treatment of DIABETES MELLITUS, TYPE 2 and PREDIABETES.. biguanides : A class of oral hypoglycemic drugs used for diabetes mellitus or prediabetes treatment. They have a structure based on the 2-carbamimidoylguanidine skeleton.	3.86	3	0	guanidines
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.	2.49	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.	2.97	4	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.	2.96	4	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.	2.04	1	0	ortho-fused polycyclic arene; tetraphenes
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.08	1	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.	3.09	5	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
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.	2.67	3	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
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.03	1	0	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
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.	3.46	1	1	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
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.	3.09	5	0	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	2.66	3	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.68	3	0	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
uridine [no description available]	4.2	2	0	uridines	drug metabolite; fundamental metabolite; human 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.	2.48	2	0	pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent
galactose galactopyranose : The pyranose form of galactose.	2.46	2	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.	5.84	16	0	monohydroxyquinoline; quinolone	bacterial xenobiotic metabolite
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.	2.03	1	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	4.03	14	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.	2	1	0	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
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)	2.41	1	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.	2.04	1	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.	5.02	9	1	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.	2.36	2	0	amine; thiol	geroprotector; human metabolite; mouse metabolite; radiation protective agent
phlorhizin [no description available]	2.08	1	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 .	1.98	1	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.	2.68	3	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.	2.05	1	0	penicillin allergen; penicillin	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.	2.39	2	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
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.	2.06	1	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
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.	2.03	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
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.	2.05	1	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.	2.03	1	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.	1.99	1	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.	5.69	10	2	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.	7.99	4	0	alkaloid; colchicine	anti-inflammatory agent; gout suppressant; mutagen
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.	2.36	2	0	antibiotic fungicide; cyclic ketone; dicarboximide; piperidine antibiotic; piperidones; secondary alcohol	anticoronaviral agent; bacterial metabolite; ferroptosis inhibitor; neuroprotective agent; protein synthesis inhibitor
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.	2.78	3	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
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.	2.06	1	0	formamides; volatile organic compound	geroprotector; hepatotoxic agent; polar aprotic solvent
cytarabine [no description available]	2.38	2	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ornithine Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.	2.39	2	0	non-proteinogenic L-alpha-amino acid; ornithine	algal metabolite; hepatoprotective agent; mouse metabolite
asparagine Asparagine: A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. (From Concise Encyclopedia Biochemistry and Molecular Biology, 3rd ed). asparagine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group.	2.21	1	0	amino acid zwitterion; asparagine; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
2-thiomalic acid [no description available]	2.41	1	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.	2.53	2	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
1,1,1-trichloroethane Trichloroethanes: Chlorinated ethanes which are used extensively as industrial solvents. They have been utilized in numerous home-use products including spot remover preparations and inhalant decongestant sprays. These compounds cause central nervous system and cardiovascular depression and are hepatotoxic. Include 1,1,1- and 1,1,2-isomers.. 1,1,1-trichloroethane : A member of the class of chloroethanes carrying three chloro substituents at position 1.	2.04	1	0	chloroethanes	polar solvent
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.	5.82	6	1	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
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.	4.2	5	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.	2.03	1	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.	5.48	15	1	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	7.45	2	0	alkane; gas molecular entity	plant metabolite; 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.	2.02	1	0	chloromethanes; methyl halides	marine metabolite; mutagen; refrigerant
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.	2.11	1	0	boranes; mononuclear parent hydride
ethyl chloride Ethyl Chloride: A gas that condenses under slight pressure. Because of its low boiling point ethyl chloride sprayed on skin produces an intense cold by evaporation. Cold blocks nerve conduction. Ethyl chloride has been used in surgery but is primarily used to relieve local pain in sports medicine.. chloroethane : The simplest and least toxic member of the class of chloroethanes, that is ethane in which a single hydrogen is substituted by a chlorine. A colourless gas at room temperature and pressure (boiling point 12degreeC), it is used as a mild topical anaesthetic to numb the skin prior to ear piercing, skin biopsies, etc., and is also used in the treatment of sports injuries. It was formerly used in the production of tetraethyllead.	2.04	1	0	chloroethanes	antipruritic drug; inhalation anaesthetic; local anaesthetic
trichlorofluoromethane trichlorofluoromethane: refrigerant, aerosol propellant; RN given refers to parent cpd; structure. trichlorofluoromethane : A one-carbon compound that is methane in which the hydrogens have been replaced by three chlorine and one fluorine atom.	2.04	1	0	chlorofluorocarbon; halomethane	environmental contaminant; NMR chemical shift reference compound; NMR solvent; refrigerant
methanesulfonic acid [no description available]	2.48	2	0	alkanesulfonic acid; one-carbon compound	Escherichia coli metabolite
pentachloroethane [no description available]	2.04	1	0	chloroethanes	non-polar solvent
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.	3.51	8	0	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
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)	2.01	1	0	primary amino compound; triol	buffer
isopentane [no description available]	2.04	1	0	alkane	refrigerant
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]	2.54	2	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.	2.54	2	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
peracetic acid Peracetic Acid: A liquid that functions as a strong oxidizing agent. It has an acrid odor and is used as a disinfectant.. peracetic acid : A peroxy acid that is acetic acid in which the OH group is substituted by a hydroperoxy group. It is a versatile oxidising agent that is used as a disinfectant.	2.05	1	0	a peroxy acid	disinfectant; oxidising agent
1,1,2,2-tetrachloroethane 1,1,2,2-tetrachloroethane: see also record for tetrachloroethane. 1,1,2,2-tetrachloroethane : A member of the class of chloroethanes that is ethane substituted by chloro groups at positions 1, 1, 2 and 2.	2.04	1	0	chloroethanes
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.04	1	0	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum 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.	2.02	1	0	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
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.	2.52	2	0	organic chloride salt; xanthene dye	fluorescent probe; fluorochrome; histological dye
acenaphthene [no description available]	2.04	1	0	acenaphthenes
methylprednisolone Methylprednisolone: A PREDNISOLONE derivative with similar anti-inflammatory action.. 6alpha-methylprednisolone : The 6alpha-stereoisomer of 6-methylprednisolone.	2.15	1	0	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.52	2	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione [no description available]	2.04	1	0	flavin
phthalimide phthalimide: RN given refers to parent cpd. phthalimide : A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.	2.25	1	0	phthalimides
fluorene [no description available]	2.04	1	0	ortho-fused polycyclic arene; ortho-fused tricyclic hydrocarbon
1,2,3-trichlorobenzene trichlorobenzene: commercial grade of trichlorobenzene containing 70% 1,2,4-trichlorobenzene & 30% 1,2,3-trichlorobenzene; see also record for 1,2,4-trichlorobenzene. trichlorobenzene : Any member of the class of chlorobenzenes carrying three chloro substituents at unspecified positions.. 1,2,3-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 2 and 3.	2.04	1	0	trichlorobenzene
hexamethylbenzene hexamethylbenzene : A methylbenzene that is benzene in which all six hydrogens have been replaced by methyl groups.	2.45	2	0	methylbenzene
n-vinyl-2-pyrrolidinone N-vinyl-2-pyrrolidinone: monomer of POVIDONE; structure given in first source	2.15	1	0	pyrrolidin-2-ones
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.	7.25	1	0	benzoic acids; tetracarboxylic acid
1-methylnaphthalene 1-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 1.	2.04	1	0	methylnaphthalene	carcinogenic agent; plant metabolite
1-chloronaphthalene 1-chloronaphthalene: word preservative; in xylamon the active ingredient is 60% 1-chloronaphthalene; structure in Merck Index, 9th ed, #2126	2.04	1	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.	2.03	1	0	naphthol	genotoxin; human xenobiotic metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	5.58	21	0	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
1,2,3,4-tetrahydroisoquinoline 1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified	2.46	2	0	isoquinolines
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	3.5	2	0	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
2-methylnaphthalene 2-methylnaphthalene: RN given refers to parent cpd. 2-methylnaphthalene : A methylnaphthalene carrying a methyl substituent at position 2.	2.04	1	0	methylnaphthalene
2-chloronaphthalene 2-chloronaphthalene: structure in first source	2.04	1	0
naphthacene tetracene : An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.	2.04	1	0	acene; tetracenes
diphenyl diphenyl: RN given refers to unlabeled cpd; structure	2.76	3	0	aromatic fungicide; benzenes; biphenyls	antifungal agrochemical; antimicrobial food preservative
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.11	1	0	xanthene
benzothiophene [no description available]	2.17	1	0	1-benzothiophenes; benzothiophene
2-xylene 2-xylene: RN given refers to parent cpd. o-xylene : A xylene substituted by methyl groups at positions 1 and 2.	2.04	1	0	xylene
2-chlorotoluene 2-chlorotoluene: RN given refers to parent cpd	2.04	1	0
2-dichlorobenzene 2-dichlorobenzene: structure. 1,2-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 2.	2.04	1	0	dichlorobenzene	hepatotoxic agent; metabolite
pseudocumene 1,2,4-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 4.	2.04	1	0	trimethylbenzene	neurotoxin
durene durene: structure. durene : A tetramethylbenzene carrying methyl groups at positions 1, 2, 4 and 5.	2.04	1	0	tetramethylbenzene
1,2,4,5-tetrachlorobenzene 1,2,4,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.	2.04	1	0	tetrachlorobenzene
dilactide dilactide: structure given in first source	2.15	1	0	dioxanes
soman Soman: An organophosphorus compound that inhibits cholinesterase. It causes seizures and has been used as a chemical warfare agent.	2.03	1	0	phosphonic ester
butyl methacrylate [no description available]	2.05	1	0	enoate ester
tert-butylbenzene [no description available]	2.04	1	0
cumene cumene : An alkylbenzene that is benzene carrying an isopropyl group.	2.04	1	0	alkylbenzene
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	1.98	1	0	nitroarene; nitrobenzenes
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.48	2	0	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.04	1	0	botanical anti-fungal agent; carvones	allergen
4-cymene 4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.	2.48	2	0	monoterpene; toluenes	human urinary metabolite; plant metabolite; volatile oil component
ethylbenzene [no description available]	2.04	1	0	alkylbenzene
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	3.58	2	0	quinuclidines; saturated organic heterobicyclic parent
monobenzone monobenzone: structure. monobenzone : The monobenzyl ether of hydroquinone. It is used as a topical drug for medical depigmentation.	2.13	1	0	benzyl ether	allergen; dermatologic drug; melanin synthesis inhibitor
1,2-dihydrostilbene 1,2-dihydrostilbene: intermdiate in biosynthesis of dihydrophenanthrenes from phenylalanine. 1,2-dihydrostilbene : A diphenylethane that is the 1,2-dihydro derivative of stilbene.	2.04	1	0	diphenylethane
n-propylbenzene n-propylbenzene: RN given refers to parent cpd. propylbenzene : An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.	2.04	1	0	alkylbenzene
n-butylbenzene butylbenzene : An alkylbenzene that is benzene substituted by a butyl group at position 1.	2.04	1	0	alkylbenzene
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.	2.04	1	0	caprolactams	human blood serum metabolite
1,4-dibromobenzene [no description available]	2.04	1	0	dibromobenzene
4-xylene p-xylene : A xylene with methyl groups at positions 1 and 4.	2.7	3	0	xylene
4-chlorotoluene 4-chlorotoluene: RN given refers to unlabeled cpd	2.04	1	0	monochlorobenzenes
1,2-epoxybutane 1,2-epoxybutane: RN given refers to cpd with unspecified isomeric designation	2.03	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.	2.76	3	0	epoxide; organochlorine compound
ethylene dibromide Ethylene Dibromide: An effective soil fumigant, insecticide, and nematocide. In humans, it causes severe burning of skin and irritation of the eyes and respiratory tract. Prolonged inhalation may cause liver necrosis. It is also used in gasoline. Members of this group have caused liver and lung cancers in rodents. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), 1,2-dibromoethane may reasonably be anticipated to be a carcinogen.. 1,2-dibromoethane : A bromoalkane that is ethane carrying bromo substituents at positions 1 and 2. It is produced by marine algae.	2.04	1	0	bromoalkane; bromohydrocarbon	algal metabolite; carcinogenic agent; fumigant; marine metabolite; mouse metabolite; mutagen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.04	1	0	alkane; gas molecular entity	food propellant; refrigerant
1-butene but-1-ene : A butene with unsaturation at position 1.	2.04	1	0	butene
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.	2.06	1	0	alkylamine
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.52	2	0	alkane
3-hydroxybutanal [no description available]	2.48	2	0
acetic anhydride acetic anhydride: RN given refers to unlabeled cpd; structure. acetic anhydride : An acyclic carboxylic anhydride derived from acetic acid.	1.99	1	0	acyclic carboxylic anhydride	metabolite; reagent
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.	3.17	5	0	cyclic dicarboxylic anhydride; furans	allergen
3-xylene m-xylene : A xylene carrying methyl groups at positions 1 and 3.	2.04	1	0	xylene
mesitylene mesitylene: structure. 1,3,5-trimethylbenzene : A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.	2.04	1	0	trimethylbenzene
1,3,5-trichlorobenzene 1,3,5-trichlorobenzene: structure in first source. 1,3,5-trichlorobenzene : A trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.	2.04	1	0	trichlorobenzene
bromobenzene [no description available]	2.04	1	0	bromoarene; bromobenzenes; volatile organic compound	hepatotoxic agent; mouse metabolite; non-polar solvent
chlorobenzene [no description available]	2.04	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.	2.73	3	0	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	2	1	0	cyclohexanones	human xenobiotic metabolite
thiophenol thiophenol : A thiol in which the sulfanyl group is attached to a phenyl group.	2.41	1	0	aryl thiol
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.45	2	0	alkane; volatile organic compound	non-polar solvent; refrigerant
1-pentene 1-pentene: structure in first source	2.04	1	0
butyl chloride butyl chloride: structure	2.75	3	0
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.	8.35	21	0	pyrrole; secondary amine
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.	2.47	2	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.	3.79	10	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
n-hexane hexane : An unbranched alkane containing six carbon atoms.	2.04	1	0	alkane; volatile organic compound	neurotoxin; non-polar solvent
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	7.99	4	0	cycloalkane; volatile organic compound	non-polar solvent
cyclohexene cyclohexene : A cycloalkene that is cylohexane with a single double bond.	3.55	2	0	cycloalkene
s-trioxane s-trioxane: a 6-membered ring composed of 3 carbons and 3 oxygens. 1,3,5-trioxane : A saturated organic heteromonocyclic parent that is cyclohexane in which the carbon atoms at positions 1, 3 and 5 are replaced by oxygen atoms.	2.02	1	0	saturated organic heteromonocyclic parent; trioxane
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.73	3	0	alkane	plant metabolite; volatile oil component
n-octanethiol octane-1-thiol : An alkanethiol that is octane substituted by a thiol group at position 1.	2.03	1	0	alkanethiol
n-dodecane dodecane : A straight-chain alkane with 12 carbon atoms. It has been isolated from the essential oils of various plants including Zingiber officinale (ginger).	2.03	1	0	alkane	plant metabolite
dodecylmercaptan dodecylmercaptan: used in polymerization of neoprenes; structure	2.03	1	0
propylene propylene: structure	2.01	1	0	alkene; gas molecular entity	refrigerant; xenobiotic
bromphenol blue Bromphenol Blue: A dye that has been used as an industrial dye, a laboratory indicator, and a biological stain.. bromophenol blue : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.	2.08	1	0	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; phenols; sultone	acid-base indicator; dye; two-colour indicator
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.	2.04	1	0	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
chloranil Chloranil: A quinone fungicide used for treatment of seeds and foliage.. tetrachloro-1,4-benzoquinone : A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.	2.11	1	0	1,4-benzoquinones; organochlorine compound	EC 2.7.1.33 (pantothenate kinase) inhibitor; metabolite
framycetin Framycetin: A component of NEOMYCIN that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). framycetin : A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.	1.98	1	0	aminoglycoside	allergen; antibacterial drug; Escherichia coli metabolite
isoquinoline [no description available]	2.15	1	0	azaarene; isoquinolines; mancude organic heterobicyclic parent; ortho-fused heteroarene
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.	2.04	1	0	acene; anthracenes; ortho-fused tricyclic hydrocarbon
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	2.04	1	0	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
pyrazolanthrone pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source. anthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.	2.07	1	0	anthrapyrazole; aromatic ketone; cyclic ketone	antineoplastic agent; c-Jun N-terminal kinase inhibitor; geroprotector
iodoantipyrine [no description available]	2.03	1	0
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.	4.71	5	0	hexosamine; secondary amino compound
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.	2.05	1	0	naphthylamine	human xenobiotic 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.	2.98	4	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.)	2.17	1	0	NTA; tricarboxylic acid	carcinogenic agent; nephrotoxic agent
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
guanidine carboxamide guanidine carboxamide: RN given refers to parent cpd	1.96	1	0	organooxygen compound
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2.13	1	0	monohydroxypyridine	plant metabolite
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).	2.46	2	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
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.	2.01	1	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.	1.97	1	0	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative
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.	2.05	1	0	catechin	antioxidant; plant metabolite
coronene coronene: structure. coronene : A ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.	2.06	1	0	ortho- and peri-fused polycyclic arene
1,12-benzoperylene 1,12-benzoperylene: structure; see also record for benzoperylene	2.04	1	0	ortho- and peri-fused polycyclic arene
benzo(e)pyrene benzo(e)pyrene: RN given refers to parent cpd. benzo[e]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings. It is listed as a Group 3 carcinogen by the IARC.	2.04	1	0	ortho- and peri-fused polycyclic arene	carcinogenic agent; mutagen
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.	2.04	1	0	ortho- and peri-fused polycyclic arene; perylenes
benzo(j)fluoranthene benzo(j)fluoranthene: dihydrodiol metabolites identified as mutagens; structure given in first source	2.04	1	0	naphthalenes
benzo(b)fluoranthene benzo[b]fluoranthene : An ortho- and peri-fused polycyclic arene that consists of a benzene ring fused with a acephenanthrylene ring.	2.04	1	0	ortho- and peri-fused polycyclic arene	mutagen
fluoranthene fluoranthene: structure. fluoranthene : An ortho- and peri-fused polycyclic arene consisting of a naphthalene and benzene unit connected by a five-membered ring.	2.04	1	0	ortho- and peri-fused polycyclic arene
benzo(k)fluoranthene [no description available]	2.04	1	0	naphthalenes
triphenylene triphenylene: structure. triphenylene : An ortho-fused polycyclic arene consisting of four fused benzene rings.	2.04	1	0	ortho-fused polycyclic arene
chrysene chrysene: structure in Merck Index, 9th ed, #2252. chrysene : An ortho-fused polycyclic arene found commonly in the coal tar.	2.46	2	0	ortho-fused polycyclic arene	plant metabolite
dibenzo(aj)anthracene dibenzo(aj)anthracene: structure in first source	2.04	1	0	phenanthrenes
benzo(a)fluorene benzo(a)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
benzo(b)fluorene benzo(b)fluorene: structure in first source	2.04	1	0	carbotetracyclic compound
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.	8.39	17	0	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.	3.46	2	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.	6.44	29	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.	2.48	2	0	1,3-benzoxazoles; mancude organic heterobicyclic parent
bicyclo(2.2.2)octane bicyclo(2.2.2)octane: structure in first source	2.11	1	0
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	4.55	7	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.	3.24	5	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.	6.15	7	0	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	6.47	22	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
1,2,4-triazole 1,2,4-triazole: RN given refers to 1H-1,2,4-triazole	7.53	2	0	1,2,4-triazole
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	2.25	1	0	diazine; pyrimidines	Daphnia magna metabolite
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.	22.87	123	11	diazine; pyrazines	Daphnia magna metabolite
cyclooctane [no description available]	2.04	1	0
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.	2.89	4	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.	1.95	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
hydrazine diamine : Any polyamine that contains two amino groups.	3.75	10	0	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
testosterone enanthate [no description available]	3.19	1	0	heptanoate ester; sterol ester	androgen
diethyl sulfide ethyl sulfide : An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.. diethyl sulfide : An ethyl sulfide compound having two ethyl groups attached to a sulfur atom.	2.04	1	0	ethyl sulfide
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.	2.11	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.	1.98	1	0	ergoline alkaloid
thymidine monophosphate Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety.. dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate).	2.37	2	0	thymidine 5'-monophosphate	fundamental metabolite
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	2.71	3	0	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
perflubron perflubron: potential anti-obesity compound; reduces food adsorption; 8-carbon perfluorocarbon radiopaque compound; an oral contrast agent for use with MRI to enhance delineation of the bowel distinguishing it from adjacent organs. perflubron : A haloalkane that is perfluorooctane in which a fluorine attached to one of the terminal carbons has been replaced by a bromine.	1.97	1	0	haloalkane; organobromine compound; perfluorinated compound	blood substitute; radioopaque medium
dicyandiamido dicyandiamido: RN given refers to parent cpd; structure. cyanoguanidine : A guanidine in which one of the amino hydrogens of guanidine itself is substituted by a cyano group. It is used in the manufacture of fertilizers, pharmaceuticals, explosives, oil well drilling muds, and dyestuffs.	2.15	1	0	guanidines; nitrile	curing agent; explosive; fertilizer; flame retardant; nitrification inhibitor
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.	2.48	2	0	monofluorobenzenes	NMR chemical shift reference compound
neopentane pediocin 5: from Pediococcus acidilactici UL5; 43 amino acid residues	2.05	1	0	alkane
propiolic acid propiolic acid: RN given refers to parent cpd; structure. propynoic acid : A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond.	2.03	1	0	acetylenic fatty acid; alpha,beta-unsaturated monocarboxylic acid; monounsaturated fatty acid; short-chain fatty acid; terminal acetylenic compound	xenobiotic metabolite
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.	2.07	1	0	calcium salt; carbonate salt; inorganic calcium salt; one-carbon compound	antacid; fertilizer; food colouring; food firming agent
cholanthrene cholanthrene: structure given in first source	2.04	1	0
menadiol [no description available]	2.04	1	0	methylnaphthalenes; naphthalenediols; naphthohydroquinone
cytisine [no description available]	2.41	1	0	alkaloid; bridged compound; lactam; organic heterotricyclic compound; secondary amino compound	nicotinic acetylcholine receptor agonist; phytotoxin; plant metabolite
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	2.76	3	0	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
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.	3.73	10	0	dicarboxylic acid; L-proline derivative; non-proteinogenic L-alpha-amino acid; pyrrolidinecarboxylic acid	antinematodal drug; excitatory amino acid agonist
norcamphor norcamphor: RN given refers to cpd without isomeric desination	2.68	3	0
caprolactone hexano-6-lactone : A epsilon-lactone that is oxepane substituted by an oxo group at position 2.	2.57	2	0	epsilon-lactone
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.	4.31	5	0
1,3-propanediol propane-1,3-diol : The simplest member of the class of propane-1,3-diols, consisting of propane in which one hydrogen from each methyl group is substituted by a hydroxy group. A colourless, viscous, water-miscible liquid with a high (210degreeC) boiling point, it is used in the synthesis of certain polymers and as a solvent and antifreeze.	2.08	1	0	propane-1,3-diols	metabolite; protic solvent
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	6.2	9	1	thiazolidine
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	4.72	5	0
hemimellitene hemimellitene: structure. 1,2,3-trimethylbenzene : A trimethylbenzene carrying methyl groups at positions 1, 2 and 3. It has been found in Centaurium erythraea.	2.04	1	0	trimethylbenzene	neurotoxin; plant metabolite
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2	1	0	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2	1	0	organic molecular entity
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	8.2	11	0	C-nitro compound; imidazoles	antitubercular agent
2-methylbenzaldehyde 2-methylbenzaldehyde: structure in first source. o-tolualdehyde : A tolualdehyde compound with the methyl substituent at the 2-position.	2.21	1	0	tolualdehyde	plant metabolite
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.	2.71	3	0	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
dicyclohexylcarbodiimide 1,3-dicyclohexylcarbodiimide : A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.	1.96	1	0	carbodiimide	ATP synthase inhibitor; cross-linking reagent; peptide coupling reagent
4-iodophenol [no description available]	2.38	2	0	iodophenol
1-chloropropane 1-chloropropane: structure in first source	2.04	1	0
2,2,4-trimethylpentane 2,2,4-trimethylpentane: nephrotoxic. isooctane : An alkane that consists of pentane bearing two methyl substituents at position 2 and a single methyl substituent at position 4.	2.04	1	0	alkane; volatile organic compound	fuel additive; nephrotoxin; non-polar solvent
butyramide butanamide : A monocarboxylic acid amide obtained by formal condensation of butanoic acid and ammonia.	2.03	1	0	butanamides; primary fatty amide
1,3-dichlorobenzene 1,3-dichlorobenzene : A dichlorobenzene carrying chloro substituents at positions 1 and 3.	2.04	1	0	dichlorobenzene
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.	3.9	11	0	dialdehyde	biomarker
1-chlorohexane [no description available]	2.04	1	0
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
lucanthone hydrochloride Schistosomicides: Agents that act systemically to kill adult schistosomes.	2.78	3	0
resazurin resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure	2.11	1	0	phenoxazine
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'.	2.04	1	0	bipyridine
tristearin tristearoylglycerol : A triglyceride that is glycerol in which all three hydroxy groups have been formally esterified with stearic acid.	2.07	1	0	triacylglycerol 54:0	Caenorhabditis elegans metabolite; plant metabolite
1,4-cyclohexanediol [no description available]	2.08	1	0
carbon tetrabromide tetrabromomethane : A one-carbon compound substituted by 4 bromo groups.	2.17	1	0	bromomethanes
diepoxybutane diepoxybutane: difunctional alkylating agent; RN given refers to cpd with unspecified isomeric designation; structure	1.98	1	0	epoxide	mutagen
1,4-dimethylnaphthalene 1,4-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 1 and 4.	2.04	1	0	dimethylnaphthalene
2,6-dimethylnaphthalene 2,6-dimethylnaphthalene: RN given refers to parent cpd. 2,6-dimethylnaphthalene : A dimethylnaphthalene carrying methyl groups at positions 2 and 6.	2.04	1	0	dimethylnaphthalene	environmental contaminant
1,2-dibromobenzene dibromobenzene : Any member of the class of bromobenzenes that consists of a benzene or a substituted benzene ring carrying two bromo groups at unspecified positions.	2.04	1	0	dibromobenzene
iodobenzene iodobenzene: RN given refers to unlabeled parent cpd	2.04	1	0
1-hexene 1-hexene: structure in first source. 1-hexene : An alkene that is hexane carrying a double bond at position 1.	2.04	1	0	alkene
pentachlorobenzene pentachlorobenzene: structure. pentachlorobenzene : A member of the class of pentachlorobenzenes that is benzene in which five of the hydrogens are replaced by chlorines. Now classed as a persistent organic pollutant under the Stockholm Convention.	2.04	1	0	pentachlorobenzenes	persistent organic pollutant
2-methylanthracene 2-methylanthracene: structure given in first source	2.04	1	0
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.44	2	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
chorismic acid Chorismic Acid: A cyclohexadiene carboxylic acid derived from SHIKIMIC ACID and a precursor for the biosynthesis of UBIQUINONE and the AROMATIC AMINO ACIDS.. chorismic acid : The (3R,4R)-stereoisomer of 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid.	2.37	2	0	5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
4-hydroxypyridine 4-pyridone: structure in first source. 4-hydroxypyridine : A monohydroxypyridine that is pyridine in which the hydrogen at position 4 has been replaced by a hydroxy group.. 4-pyridone : The simplest member of the class of pyridin-4-ones, that is 1,4-dihydropyridine in which the hydrogens at position 4 have been replaced by an oxo group.	2.13	1	0	4-pyridones; monohydroxypyridine
n-methylpiperidine N-methylpiperidine: RN given refers to parent cpd	2	1	0
n-tetradecane tetradecane : A straight chain alkane consisting of 14 carbon atoms.	7.03	1	0	long-chain alkane	plant metabolite; volatile oil component
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.	2.25	1	0
1,2,3-trimethoxybenzene 1,2,3-trimethoxybenzene : A methoxybenzene that is benzene substituted by methoxy groups at positions 1, 2 and 3 respectively.	2.05	1	0	methoxybenzenes	plant metabolite
1,2,3,4-tetrachlorobenzene 1,2,3,4-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4.. tetrachlorobenzene : Any member of the class of chlorobenzenes carrying four chloro groups at unspecified positions.	2.04	1	0	tetrachlorobenzene
1,2,3,5-tetrachlorobenzene 1,2,3,5-tetrachlorobenzene : A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.	2.04	1	0	tetrachlorobenzene
formal glycol [no description available]	2.08	1	0	cyclic acetal; dioxolane
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.	1.98	1	0	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-monophosphate	fundamental 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.	4.15	2	0	delta-lactam; piperidones	EC 1.2.1.88 (L-glutamate gamma-semialdehyde dehydrogenase) inhibitor
9-methylanthracene [no description available]	2.04	1	0
9,10-dimethylanthracene 9,10-dimethylanthracene: RN given refers to parent ion	2.04	1	0
ameltolide ameltolide: structure given in first source; RN given refers to parent cpd	1.99	1	0	benzamides
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.	3.19	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin; synthetic oral contraceptive
adamantanecarboxylic acid [no description available]	4.27	18	0
2-aminobenzimidazole 2-aminobenzimidazole: metabolite of benomyl; RN given refers to parent cpd. 2-aminobenzimidazole : A member of the class of benzimidazoles that is benzimidazole in which the hydrogen at position 2 is replaced by an amino group.	1.98	1	0	benzimidazoles	marine xenobiotic metabolite
deoxycytidine [no description available]	2.43	2	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxyuridine [no description available]	2.01	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxycytidine monophosphate Deoxycytidine Monophosphate: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.. 2'-deoxycytosine 5'-monophosphate : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.66	3	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
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.	9.23	8	4	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.04	1	0	alkane
fenchone, (+-)-isomer fenchone: RN given refers to cpd with unspecified isomeric designation. fenchone : A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare).	2.01	1	0	carbobicyclic compound; cyclic terpene ketone; fenchane monoterpenoid	plant metabolite
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.48	2	0	alkali metal hydroxide
manganese dioxide [no description available]	2.17	1	0	manganese molecular entity; metal oxide
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.	2.77	3	0
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	2.04	1	0	pinene	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.	2.47	2	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
digoxigenin Digoxigenin: 3 beta,12 beta,14-Trihydroxy-5 beta-card-20(22)-enolide. A cardenolide which is the aglycon of digoxin. Can be obtained by hydrolysis of digoxin or from Digitalis orientalis L. and Digitalis lanata Ehrh.. digoxigenin : A hydroxy steroid that consists of 5beta-cardanolide having a double bond at the 20(22)-position as well as hydroxy groups at the 3beta-, 12beta- and 14beta-positions. It has been isolated from the plant species of the genus Digitalis.	3.69	10	0	12beta-hydroxy steroid; 14beta-hydroxy steroid; 3beta-hydroxy steroid; 3beta-sterol	hapten; plant metabolite
[2-(2,6-dimethylanilino)-2-oxoethyl]-diethyl-(phenylmethyl)ammonium denatonium: a potent bittering agent	2.25	1	0	amino acid amide
6-methylchrysene 6-methylchrysene: RN given refers to parent cpd; structure given in first source	2.04	1	0	carbopolycyclic compound
decane decane : A straight-chain alkane with 10 carbon atoms.	2.04	1	0	alkane
4-octylphenol 4-octylphenol: xenoestrogen. 4-octylphenol : A member of the class of phenols that is phenol which is substituted at the para- position by an octyl group.	1.99	1	0	phenols	metabolite; surfactant; xenoestrogen
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.	2.49	2	0	organic cation	geroprotector; herbicide
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.	2.4	2	0	tertiary amine
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.	5.02	12	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.	1.97	1	0	aromatic amine; guanidines; organochlorine compound; pyrazines	diuretic; sodium channel blocker
diallyl disulfide diallyl disulfide: major constituent of garlic oil. diallyl disulfide : An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.	2	1	0	organic disulfide	antifungal agent; antineoplastic agent; plant metabolite
phenethyl isothiocyanate phenethyl isothiocyanate: a dietary liver aldehyde dehydrogenase inhibitor; promotes urinary bladder carcinoma. phenethyl isothiocyanate : An isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties.	2.31	1	0	isothiocyanate	antineoplastic agent; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; metabolite
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.	2.44	2	0	2-benzofurans; gamma-lactone; organic heteropentacyclic compound; oxaspiro compound; polyphenol; xanthene dye	fluorescent dye; radioopaque medium
flupenthixol Flupenthixol: A thioxanthene neuroleptic that, unlike CHLORPROMAZINE, is claimed to have CNS-activating properties. It is used in the treatment of psychoses although not in excited or manic patients. (From Martindale, The Extra Pharmacopoeia, 30th ed, p595). flupenthixol : A thioxanthene derivative having a trifluoromethyl substituent at the 2-position and a 3-(4-(2-hydroxyethyl)piperazin-1-yl)propylidene group at the 10-position with undefined double bond stereochemistry.	1.95	1	0	thioxanthenes
12-methylbenzanthracene [no description available]	2.04	1	0
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.	3.5	1	1	hydrochloride	fluorochrome; histological dye
2-methylphenanthrene [no description available]	2.04	1	0
7-methylbenzanthracene [no description available]	2.04	1	0
ddms DDMS: a water soluble and highly specific inhibitor of cytochrome P-450 omega-hydroxylase	2.44	2	0	chlorophenylethane; monochlorobenzenes
n,n-dimethylacrylamide [no description available]	2.1	1	0
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.	2.71	3	0	fluorescein isothiocyanate
mannose mannopyranose : The pyranose form of mannose.	3.19	5	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.	1.99	1	0	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
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.	2.05	1	0	3',5'-cyclic pyrimidine nucleotide	human metabolite
5-methylchrysene 5-methylchrysene: methylchrysenes in tobacco smoke are suspected to contribute to tumorigenicity of this inhalant; RN given refers to unlabeled cpd; structure	2.04	1	0	carbopolycyclic compound
5,6-dimethylchrysene 5,6-dimethylchrysene: structure given in first source	2.04	1	0
7-ethylbenz(a)anthracene [no description available]	2.04	1	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.	2.01	1	0	diastereoisomeric mixture; homocysteines; non-proteinogenic alpha-amino acid; sulfoximide	EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor; ferroptosis inducer
raspberry ketone rheosmin: an NSAID that blocks NF-kappaB activation; isolated from Pinus densiflora; structure in first source. raspberry ketone : A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at position 4 by a hydroxy group. It is found in a variety of fruits including raspberries, blackberries and cranberries, and is used in perfumery and cosmetics.	2.13	1	0	methyl ketone; phenols	androgen antagonist; cosmetic; flavouring agent; fragrance; hepatoprotective agent; metabolite
1-adamantanecarboxamide [no description available]	2.4	2	0
vidarabine adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.	2.38	2	0	beta-D-arabinoside; purine nucleoside	antineoplastic agent; bacterial metabolite; nucleoside antibiotic
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.	2.05	1	0	azobenzenes; dicarboxylic acid	non-steroidal anti-inflammatory drug; prodrug
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.	3.64	9	0	amino dicarboxylic acid; D-alpha-amino acid; D-aspartic acid derivative; secondary amino compound	neurotransmitter agent
tert-nitrosobutane [no description available]	1.98	1	0
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.49	2	0	cobalt group element atom; platinum group metal atom
lanthanum [no description available]	2.06	1	0	f-block element atom; lanthanoid atom; scandium group element 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.	3.14	5	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.	2.46	2	0	elemental mercury; zinc group element atom	neurotoxin
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.	4.79	9	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.	3.33	6	0	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	7.74	3	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.	8.29	6	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.	9.23	16	0	iron group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	2.03	1	0	f-block element atom; lanthanoid 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.	3.61	8	0	copper group element atom; elemental silver	Escherichia coli metabolite
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.	2.03	1	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.	2.48	2	0	titanium group element atom
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.	2.49	2	0	cadmium molecular entity; zinc group element 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.	2.72	3	0	chromium group element atom; metal allergen	micronutrient
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.	2.17	1	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.	3.77	10	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.	5.47	19	0	copper group element atom; elemental gold
helium Helium: A noble gas with the atomic symbol He, atomic number 2, and atomic weight 4.003. It is a colorless, odorless, tasteless gas that is not combustible and does not support combustion. It was first detected in the sun and is now obtained from natural gas. Medically it is used as a diluent for other gases, being especially useful with oxygen in the treatment of certain cases of respiratory obstruction, and as a vehicle for general anesthetics.	2.43	2	0	monoatomic helium; noble gas atom; s-block element atom	food packaging gas
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.	2.63	2	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.	2.17	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.	2.05	1	0	titanium group element atom
galactosamine 2-amino-2-deoxy-D-galactopyranose : The pyranose form of D-galactosamine.. D-galactosamine : The D-stereoisomer of galactosamine.	7.15	1	0	D-galactosamine; primary amino compound	toxin
sodium nitrate sodium nitrate : The inorganic nitrate salt of sodium.	2.03	1	0	inorganic nitrate salt; inorganic sodium salt	fertilizer; NMR chemical shift reference compound
palladium chloride palladium chloride: RN given refers to parent cpd; structure. palladium(II) chloride : A palladium coordination entity consisting of palladium(II) bound to two chlorine atoms.	2.06	1	0	palladium coordination entity	catalyst
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	3.21	5	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
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.	2.78	3	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.	2.03	1	0	diatomic bromine
metoprine metoprine: histamine methyltransferase antagonist	1.96	1	0
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.11	5	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.	2.7	3	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.	2.31	1	0	diatomic chlorine; gas molecular entity	bleaching agent
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).	2.37	2	0	epoxide
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.	2.02	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
trolamine salicylate Arthritis: Acute or chronic inflammation of JOINTS.	3.68	3	0
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.	2.37	2	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
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.	2.48	2	0	titanium oxides	food colouring
misonidazole Misonidazole: A nitroimidazole that sensitizes normally radio-resistant hypoxic cells to radiation. It may also be directly cytotoxic to hypoxic cells and has been proposed as an antineoplastic.	1.96	1	0
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	1	0
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.	2.76	3	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
sodium bisulfide sodium bisulfide: RN given refers to sodium sulfide (Na(SH)); see also record for sodium sulfide (Na2S)	2.08	1	0
fluorides [no description available]	2.17	1	0	halide anion; monoatomic fluorine
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.	7.06	1	0	crown ether; saturated organic heteromonocyclic parent	phase-transfer catalyst
methasquin methasquin: folic acid antagonist that has been used in the treatment of experimental leukemia; acts by inhibiting the dihydrofolate reductase in the cell; minor descriptor (75-85); on-line & Index Medicus search ASPARTIC ACID/AA (75-85); RN given refers to parent cpd	1.96	1	0
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.	5.76	15	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]	2.03	1	0	halide anion; monoatomic iodine	human metabolite
fludarabine phosphate fludarabine phosphate: structure given in first source. fludarabine phosphate : A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Once incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas.	2.01	1	0	nucleoside analogue; organofluorine compound; purine arabinonucleoside monophosphate	antimetabolite; antineoplastic agent; antiviral agent; DNA synthesis inhibitor; immunosuppressive agent; prodrug
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.	3.75	10	0	benzenes; phenyl acetates
n-phenylethanolamine [no description available]	2.13	1	0	aralkylamine
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.	4.4	2	2	chloride salt; organic chloride salt	antiseptic drug; surfactant
pyrrolidine [no description available]	7.44	2	0	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
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.	2.1	1	0	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
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
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.	2.76	3	0	ortho- and peri-fused polycyclic arene	fluorescent probe; persistent organic pollutant
dihydro-beta-erythroidine Dihydro-beta-Erythroidine: Dihydro analog of beta-erythroidine, which is isolated from the seeds and other plant parts of Erythrina sp. Leguminosae. It is an alkaloid with curarimimetic properties.. dihydro-beta-erythroidine : An organic heterotetracyclic compound resulting from the partial hydrogenation of the 1,3-diene moiety of beta-erythroidine to give the corresponding 2-ene.	2.02	1	0	delta-lactone; organic heterotetracyclic compound; tertiary amino compound	nicotinic antagonist
1-phenylcyclohexylamine 1-phenylcyclohexylamine: RN given refers to parent cpd	2.77	3	0
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.	3.3	6	0
alkenes [no description available]	3.14	5	0
calcium oxalate Calcium Oxalate: The calcium salt of oxalic acid, occurring in the urine as crystals and in certain calculi.. calcium oxalate : The calcium salt of oxalic acid, which in excess in the urine may lead to formation of oxalate calculi (kidney stones).	2.13	1	0	organic calcium salt
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.	3.67	9	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	2.05	1	0
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.	7.38	2	0
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.3	6	0	pseudohalide anion	mitochondrial respiratory-chain inhibitor
diadonium diadonium: RN given refers to diiodide; structure	4.28	4	1
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.	2.08	1	0	penicillin allergen; penicillin	antibacterial drug
vidarabine phosphate Vidarabine Phosphate: An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.	2.01	1	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.	2.92	4	0	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
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).	3.16	5	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
2,3,4,5-tetrachlorobiphenyl tetrachlorobiphenyl : Any polychlorobiphenyl with molecular formula C12H6Cl4.	2.04	1	0	tetrachlorobenzene; tetrachlorobiphenyl
etoposide [no description available]	2.05	1	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
substance p [no description available]	2.07	1	0	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent
2,5-dichlorobiphenyl 2,5-dichlorobiphenyl : A dichlorobiphenyl that is p-dichlorobenzene in which one of the hydrogens has been replaced by a phenyl group.	2.04	1	0	dichlorobenzene; dichlorobiphenyl
2,4'-dichlorobiphenyl 2,4'-dichlorobiphenyl: RN given refers to unlabeled cpd. 2,4'-dichlorobiphenyl : A dichlorobiphenyl that is chlorobenzene in which the hydrogen at position 2 has been replaced by a 4-chlorophenyl group.	2.04	1	0	dichlorobiphenyl; monochlorobenzenes
2,4,6-trichlorobiphenyl 2,4,6-trichlorobiphenyl: structure given in first source	2.04	1	0
ribavirin Rebetron: Rebetron is tradename	9.94	12	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
fluorescamine Fluorescamine: A nonfluorescent reagent for the detection of primary amines, peptides and proteins. The reaction products are highly fluorescent.	7.4	2	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
n-(2-hydroxypropyl)methacrylamide Duxon: RN given refers to unlabeled cpd	2.1	1	0
ng-nitroarginine methyl ester NG-Nitroarginine Methyl Ester: A non-selective inhibitor of nitric oxide synthase. It has been used experimentally to induce hypertension.	4.2	17	0	alpha-amino acid ester; L-arginine derivative; methyl ester; N-nitro compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor
quisqualic acid Quisqualic Acid: An agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis.	2.01	1	0	non-proteinogenic alpha-amino acid
desogestrel Desogestrel: A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents (ORAL CONTRACEPTIVES, COMBINED).	3.19	1	0	17beta-hydroxy steroid; terminal acetylenic compound	contraceptive drug; progestin; synthetic oral contraceptive
torsemide Torsemide: A pyridine and sulfonamide derivative that acts as a sodium-potassium chloride symporter inhibitor (loop diuretic). It is used for the treatment of EDEMA associated with CONGESTIVE HEART FAILURE; CHRONIC RENAL INSUFFICIENCY; and LIVER DISEASES. It is also used for the management of HYPERTENSION.. torasemide : An N-sulfonylurea obtained by formal condensation of [(3-methylphenyl)amino]pyridine-3-sulfonic acid with the free amino group of N-isopropylurea. It is a potent loop diuretic used for the treatment of hypertension and edema in patients with congestive heart failure.	1.99	1	0	aminopyridine; N-sulfonylurea; secondary amino compound	antihypertensive agent; loop diuretic
epirubicin Epirubicin: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.	2.02	1	0	aminoglycoside; anthracycline antibiotic; anthracycline; deoxy hexoside; monosaccharide derivative; p-quinones; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	antimicrobial agent; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
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.	2.71	3	0
n-cyano-n'-(1,1-dimethylpropyl)-n''-(3-pyridinyl)guanidine N-cyano-N'-(1,1-dimethylpropyl)-N''-(3-pyridinyl)guanidine: potassium channel opener	2.42	2	0	pyridines
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.	2.25	1	0	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor
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.	2.46	2	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
triclabendazole [no description available]	2.45	2	0	aromatic ether
ck 0569 a guanidino propyl piperazine: anti-plaque agent; RN given refers to dimethanesulfonate; structure given in first source	1.96	1	0
piritrexim piritrexim: RN given refers to parent cpd; structure given in first source	1.96	1	0
levocabastine levocabastine: for the temporary relief of the signs and symptoms of seasonal allergic conjunctivitis	2.91	4	0	piperidines
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.	3.42	1	1	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
quinpirole Quinpirole: A dopamine D2/D3 receptor agonist.. quinpirole : A pyrazoloquinoline that is (4aR,8aR)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrazolo[3,4-g]quinoline substituted by a propyl group at position 5. It acts as a dopamine agonist.	3.7	10	0	pyrazoloquinoline	dopamine agonist
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.	2.13	1	0	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic
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.	2.05	1	0	hydrochloride	bone density conservation agent; estrogen antagonist; estrogen receptor modulator
adapalene Adapalene: A naphthalene derivative that has specificity for RETINOIC ACID RECEPTORS. It is used as a DERMATOLOGIC AGENT for the treatment of ACNE.. adapalene : A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.	2.06	1	0	adamantanes; monocarboxylic acid; naphthoic acid	dermatologic drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; non-steroidal anti-inflammatory drug
topotecan Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.	7.66	2	0	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
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.	2.13	1	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
irinotecan [no description available]	2.03	1	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.	4.36	4	1	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic
zanamivir Zanamivir: A guanido-neuraminic acid that is used to inhibit NEURAMINIDASE.	7.48	11	0	guanidines	antiviral agent; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	4.71	9	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
myrtenal myrtenal: RN refers to cpd without isomeric designation; structure given in first source	7.41	1	0
gadolinium chloride gadolinium chloride: a macrophage inhibitor; reduces pulmonary injury and inflammatory mediator production induced by inhaled ozone	3.19	5	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.	2.51	2	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
glycoluril glycoluril: a compound made of two 2-imidazolidinone fused at the 4 and 5 positions	2.4	2	0	azabicycloalkane; ureas
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.46	2	0	one-carbon compound; perfluoroalkanesulfonic acid
isothiocyanic acid [no description available]	2.07	1	0	hydracid; one-carbon compound
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.	2.65	3	0
tenocyclidine tenocyclidine : A tertiary amino compound that consists of cyclohexane having piperidin-1-yl and thiophen-2-yl groups attached at position 1. A dissociative anaesthetic drug with halluccinogenic and stimulant effects. Its effects are similar to those of phencyclidine (PCP, an analogue with the thienyl group replaced by phenyl), but it is rather more potent.	7.44	2	0	piperidines; tertiary amino compound; thiophenes	central nervous system stimulant; hallucinogen; neuroprotective agent; NMDA receptor antagonist
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.	2.31	1	0	beta-D-glucoside	plant metabolite
nelfinavir Nelfinavir: A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.. nelfinavir : An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.	3.44	1	1	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor
2-adamantanol [no description available]	2.94	4	0
adamantanone adamantanone: structure	5.1	14	0	adamantanones
1-adamantanol [no description available]	8.3	6	0
kemantane kemantane: used in the treatment of pulmonary tuberculosis patients	3.07	5	0	adamantanones
2,4-diamino-5-adamantyl-6-methylpyrimidine [no description available]	4.54	25	0
1,3-adamantanedicarboxylic acid [no description available]	7.96	4	0
adamantane diazirine adamantane diazirine: structure in second source	3.57	9	0
tromantadine [no description available]	3.75	2	1	secondary carboxamide
u 37883a U 37883A: an antagonist of vascular ATP-sensitive potassium channel openers; structure given in first source	6.57	63	0
adamantylidene adamantylidene: structure	3.68	9	0
3-(2'-spiroadamantane)-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane 3-(2'-spiroadamantane)-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane: chemiluminescent substrate for alkaline phosphatase	6.51	36	0
rolofylline rolofylline: selective antagonist for adenosine receptors; a cardiovascular agent	2.41	2	0	oxopurine
3-(2'-(spiro-5-chloroadamantane))-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane 3-(2'-(spiro-5-chloroadamantane))-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane: used as reagent in DNA sequencing	3.38	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.	16.44	56	26	D-glucopyranose	epitope; mouse metabolite
simvastatin acid simvastatin acid: structure given in first source	3.42	1	1	carbonyl compound
1,5-anhydroglucitol 1,5-anhydroglucitol: structure. 1,5-anhydro-D-glucitol : An anhydro sugar of D-glucitol.	4.45	2	2	anhydro sugar	human metabolite
thymidine 5'-triphosphate thymidine 5'-triphosphate: RN given refers to parent cpd. dTTP : A thymidine phosphate having a triphosphate group at the 5'-position.	2.38	2	0	pyrimidine 2'-deoxyribonucleoside 5'-triphosphate; thymidine phosphate	Escherichia coli metabolite; mouse metabolite
plerixafor plerixafor: a bicyclam derivate, highly potent & selective inhibitor of HIV-1 & HIV-2. plerixafor : An azamacrocycle consisting of two cyclam rings connected by a 1,4-phenylenebis(methylene) linker. It is a CXCR4 chemokine receptor antagonist and a hematopoietic stem cell mobilizer. It is used in combination with grulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells to the perpheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin's lymphoma and multiple myeloma.	2.13	1	0	azacycloalkane; azamacrocycle; benzenes; crown amine; secondary amino compound; tertiary amino compound	anti-HIV agent; antineoplastic agent; C-X-C chemokine receptor type 4 antagonist; immunological adjuvant
amprenavir [no description available]	3.44	1	1	carbamate ester; sulfonamide; tetrahydrofuryl ester	antiviral drug; HIV protease inhibitor
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.	8.44	23	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	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.	2.13	1	0	methylcytosine; pyrimidines	human metabolite
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.	2.05	1	0	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
fluorexon fluorexon: structure	2.43	2	0	xanthene dye	fluorochrome
2'-deoxycytidine 5'-triphosphate 2'-deoxycytidine 5'-triphosphate: RN given refers to unlabeled parent cpd	1.97	1	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite
10,10'-dimethyl-9,9'-biacridinium 10,10'-dimethyl-9,9'-biacridinium: chemoluminescent probe; RN given refers to dinitrate; Lucigenin refers to dinitrate	3.31	1	0
aica ribonucleotide AICA ribonucleotide: purine precursor that has antineoplastic activity. AICA ribonucleotide : A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative.	2.11	1	0	1-(phosphoribosyl)imidazolecarboxamide; aminoimidazole	cardiovascular drug; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
4-methylumbelliferyl phosphate [no description available]	2.38	2	0
testosterone undecanoate [no description available]	3.19	1	0	steroid ester
nile red nile red : An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.	3.5	1	1	aromatic amine; cyclic ketone; organic heterotetracyclic compound; tertiary amino compound	fluorochrome; histological dye
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.47	2	0
pyrrolidine dithiocarbamate pyrrolidine dithiocarbamic acid: spelled pyrolidine in J Nutr 1979 reference; RN given refers to parent cpd. pyrrolidine dithiocarbamate : A member of the class of dithiocarbamic acids that is the N-dithiocarboxy derivative of pyrrolidine.	2.08	1	0	dithiocarbamic acids; pyrrolidines	anticonvulsant; antineoplastic agent; geroprotector; neuroprotective agent; NF-kappaB inhibitor; radical scavenger
4-nitrobenzylthioinosine 4-nitrobenzylthioinosine: inhibitor of nucleoside transport; acts on ENT1	2	1	0	purine nucleoside
5-bromo-4-chloro-3-indoxyl phosphate 5-bromo-4-chloro-3-indoxyl phosphate: substrate for demonstration of activity of alkaline phosphatase; structure given in first source. 5-bromo-4-chloro-3-indolyl phosphate : An aryl phosphate that is indoxyl phopshate 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, alkaline phosphatase, which cleaves the phosphate group to give 5-bromo-4-chloroindoxyl, which immediately dimerises to give an intensely blue product.	2.67	3	0	aryl phosphate; indoles; organobromine compound; organochlorine compound	chromogenic compound
repaglinide [no description available]	2.08	1	0	piperidines
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.	2.1	1	0	benzimidazoles; biphenyls; carboxybiphenyl	angiotensin receptor antagonist; antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; environmental contaminant; xenobiotic
boron nitride [no description available]	2.31	1	0	nitride
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.	3.02	4	0
benzeneboronic acid [no description available]	2.06	1	0	boronic acids
1,7-phenanthroline [no description available]	2.73	3	0	phenanthroline
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.	18.27	147	12	1,2,3-triazole
diazobenzenesulfonic acid diazobenzenesulfonic acid: RN given refers to parent cpd; structure	1.96	1	0
4-aminoquinoline [no description available]	2.17	1	0
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.	3.19	5	0	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
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.	3.16	5	0	artemisinin derivative; cyclic acetal; organic peroxide; semisynthetic derivative; sesquiterpenoid	antimalarial
cyclopropylamine cyclopropylamine: RN given refers to parent cpd. cyclopropylamine : A primary aliphatic amine that consists of cyclopropane bearing a single amino substituent.	7.03	1	0	primary aliphatic amine	mouse metabolite
dibenzocycloheptadiene 10,11-dihydro-5H-dibenzo(a,d)cycloheptene: structure in first source	2.13	1	0
3-amino-1,2,4-triazine [no description available]	1.98	1	0
5-hydroxymethylcytosine 5-(hydroxymethyl)cytosine : A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a hydroxymethyl group.	2.13	1	0	aminopyrimidine; aromatic primary alcohol; nucleobase analogue; pyrimidone	human metabolite; mouse metabolite
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	1.97	1	0
enrofloxacin Enrofloxacin: A fluoroquinolone antibacterial and antimycoplasma agent that is used in veterinary practice.. enrofloxacin : A quinolinemonocarboxylic acid that is 1,4-dihydroquinoline-3-carboxylic acid substituted by an oxo group at position 4, a fluoro group at position 6, a cyclopropyl group at position 1 and a 4-ethylpiperazin-1-yl group at position 7. It is a veterinary antibacterial agent used for the treatment of pets.	2.07	1	0	cyclopropanes; N-alkylpiperazine; N-arylpiperazine; organofluorine compound; quinolinemonocarboxylic acid; quinolone	antibacterial agent; antimicrobial agent; antineoplastic agent
cromakalim Cromakalim: A potassium-channel opening vasodilator that has been investigated in the management of hypertension. It has also been tried in patients with asthma. (Martindale, The Extra Pharmacopoeia, 30th ed, p352)	3.79	11	0
sanfetrinem sanfetrinem: orally absorbed hexetil ester of GV-104326	2	1	0
carbohydrazide carbohydrazide: structure. carbohydrazide : A hydrazide consisting of hydrazine carrying one or more carboacyl groups.. carbonyl dihydrazine : A carbohydrazide obtained by formal condensation between hydrazinecarboxylic acid and hydrazine.	2.55	2	0	carbohydrazide; one-carbon compound
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.	7.49	9	0	carbamate ester; oxazolidinone	metabolite
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.	2.41	2	0	hydroxy-1,2-naphthoquinone
nalidixate sodium tris(hydroxymethyl)phosphine: coupling reagent for enzyme immobilization	2.04	1	0
6-carboxyfluorescein 6-carboxyfluorescein: originally sold as 6-carboxyfluorescein, but commercial product is a mixture of two isomers; correct name is 5(6)-carboxyfluorescein	2.07	1	0	monocarboxylic acid
rosiglitazone [no description available]	10.45	10	5	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
s20098 [no description available]	3.95	2	1	acetamides
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.	7.41	1	0	organoammonium salt	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor
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.	2.08	1	0	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic
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.	2.04	1	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
nsc-172755 butocin: S-substituted analog of mercaptopurine which functions as a cytostatic agent; minor descriptor (75-85); on-line search 6-MERCAPTOPURINE/AA (75-84); Index Medicus search MERCAPTOPURINE/analogs (75-84)	4.62	1	1
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.	3.89	2	1	iditol	fungal metabolite
1-cyanoadamantane [no description available]	7.04	1	0
irgarol 1051 irgarol 1051: a booster biocide; structure given in first source. irgarol 1051 : A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine carrying a N-tert-butyl, N'-cyclopropyl and a methylsulfanyl group at position 6.	2.03	1	0	aryl sulfide; cyclopropanes; diamino-1,3,5-triazine	antifouling biocide; environmental contaminant; xenobiotic
camphane camphane: structure given in first source	7.41	2	0	monoterpene; terpenoid fundamental parent
s 53482 flumioxazin : A benzoxazine that is N-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one which is substituted at position 6 by a 1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl group and at position 7 by a fluorine. A protoporphyrinogen oxidase inhibitor, it is used for the control of weeds in soya, peanuts, and a variety of vegetable and fruit crops.	2.17	1	0	benzoxazine; dicarboximide; organofluorine compound; terminal acetylenic compound	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide; teratogenic agent
lopinavir [no description available]	3.44	1	1	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
arginine methyl ester arginine methyl ester: RN given refers to (L)-isomer	2.05	1	0	alpha-amino acid ester
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	3.42	7	0
1-(2-pyridinyl)piperazine 1-(2-pyridinyl)piperazine: metabolite of buspirone & gepirone	2.06	1	0
diprotin a [no description available]	2.51	2	0	peptide
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.	2.05	1	0	D-glucuronic acid	algal metabolite
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.	2	1	0	beta-D-galactoside; C-nitro compound	chromogenic compound
1,3,4-oxadiazole 1,3,4-oxadiazole: structure in first source	2.11	1	0
lumisantonin lumisantonin: RN given refers to (3aR-(3aalpha,3bbeta,5abeta,6beta,8aalpha,8bR*))-isomer	2.13	1	0
1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol 1-(2-nitro-1-imidazolyl)-3-aziridino-2-propanol: structure given in first source	1.96	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.	3.03	4	0	cobalt group element atom; metal allergen	micronutrient
hydrogen sulfite [no description available]	2.13	1	0	sulfur oxoanion	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
1,2-bis(2-aminophenoxy)ethane-n,n,n',n'-tetraacetic acid 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid: structure in first source	2.46	2	0	polyamino carboxylic acid; tetracarboxylic acid	chelator
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.	2.42	2	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.	2.43	2	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	2.01	1	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.	2.01	1	0
1,4-dihydropyridine [no description available]	1.99	1	0
sr141716 [no description available]	5.07	7	0	amidopiperidine; carbohydrazide; dichlorobenzene; monochlorobenzenes; pyrazoles	anti-obesity agent; appetite depressant; CB1 receptor antagonist
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.	2.07	1	0	ether; imidazoles; monomethoxybenzene	TRP channel blocker
fpl 55712 FPL 55712: inhibitor of SRS-A and LTC4 and LTD4 receptors	1.97	1	0	aromatic ketone
artesunic acid [no description available]	3.17	5	0
bradykinin, des-arg(9)- bradykinin, des-Arg(9)-: RN given refers to parent cpd	2.39	2	0	oligopeptide	bradykinin receptor B2 agonist
epibatidine epibatidine: a powerful, though toxic, pain killer produced by the poison arrow frog, Epipedobates tricolor; structure given in first source; more potent than morphine but acts at nicotine rather than opiate receptors	2.01	1	0
u 69593 U 69593: selective ligand for opioid K-receptor. U69593 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of phenylacetic acid and the secodary amino group of (5R,7S,8S)-N-methyl-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-amine.	2.1	1	0	monocarboxylic acid amide; N-alkylpyrrolidine; organic heterobicyclic compound; oxaspiro compound	anti-inflammatory agent; diuretic; kappa-opioid receptor agonist
adamantyl isothiocyanate adamantyl isothiocyanate: structure in first source	2.82	3	0
afdx 116 otenzepad: cardioselective muscarinic receptor antagonist; structure given in first source	2.67	3	0	benzodiazepine
ecopipam ecopipam: structure given in first source	1.99	1	0	benzazepine
senktide [no description available]	2.07	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.	3.77	2	1	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
ci 988 PD 134308: selective cholecystokinin type B receptor antagonist; inhibits growth of LoVo, a human colon cancer cell line; structure given in first source	4	4	0
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.	4.65	3	2
tadalafil [no description available]	2.13	1	0	benzodioxoles; pyrazinopyridoindole	EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor; vasodilator agent
6-methyl-2-ethyl-3-hydroxypyridine 6-methyl-2-ethyl-3-hydroxypyridine: compound used in second source was chlorhydrate; has been used as retinoprotector	2.13	1	0
2-ethynylnaphthalene 2-ethynylnaphthalene: RN given refers to unlabeled parent cpd	2	1	0
delta-philanthotoxin delta-philanthotoxin: from wasp Philanthus triangulum; blocks transmission postsynaptically at excitory synapses	2.13	1	0
3'-o-(4-benzoyl)benzoyladenosine 5'-triphosphate 3'-O-(4-benzoyl)benzoyladenosine 5'-triphosphate: purinergic receptors agonist; structure given in first source	3.04	4	0	purine ribonucleoside triphosphate
morphiceptin, n-me-phe(3)- morphiceptin, N-Me-Phe(3)-: RN given refers to D-prolinamide, all L-isomer	2.4	2	0
sr 48692 SR 48692: structure in first source; a neurotensin receptor-1 antagonist	3.95	13	0	N-acyl-amino acid
n,n-dipropyl-2-(4-methoxy-3-(2-phenylethoxy)phenyl)ethylamine monohydrochloride N,N-dipropyl-2-(4-methoxy-3-(2-phenylethoxy)phenyl)ethylamine monohydrochloride: structure given in first source; a sigma receptor ligand	2.03	1	0
1,3,4-thiadiazole 1,3,4-thiadiazole: structure given in first source	7.31	1	0	thiadiazole
rb 101 RB 101: structure given in first source; inhibits enkephalinase and aminopeptidases; biologically cleaved at disulfide to produce inhibitors of both aminopeptidase N and neutral endopeptidase	1.98	1	0
a 71623 A 71623: structure given in first source; a cholecystokinin-A receptor agonist	1.98	1	0
1,2-dioxetane [no description available]	2.52	2	0
bw a1433u BW A1433U: adenosine A3 receptor antagonist; attenuates hypoxia-induced AH interval prolongation; derivative of 1,3-dipropyl-8-phenylxanthine	1.98	1	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	2.02	1	0
rti 121 RTI 121: structure given in first source; selectively binds to dopamine transporters	2.08	1	0
kallidin, des-arg(10)- kallidin, des-Arg(10)-: includes both L and D isomers of Phe(8)	1.98	1	0
piperaquine piperaquine : An aminoquinoline that is 1,3-di(piperazin-1-yl)propane in which the nitrogen at position 4 of each of the piperazine moieties is replaced by a 7-chloroquinolin-4-yl group.	7.67	6	4	aminoquinoline; N-arylpiperazine; organochlorine compound	antimalarial
emoxypine succinate emoxypine succinate: has antihypoxic effects	2.52	2	0
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).	4.08	4	0	carbene; methanediyl
1-adamantaneacetic acid [no description available]	2.95	4	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).	2.75	3	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.	3.42	7	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.	3.65	9	0	methanesulfonate salt	anticoronaviral agent; antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor
gefitinib [no description available]	2.02	1	0	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
t-kinin T-kinin: from rat plasma	1.99	1	0	peptide
2-nitrophenylgalactoside 2-nitrophenylgalactoside: RN given refers to cpd without isomeric designation	2	1	0
n(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine: structure given in first source; a selective A(3) adenosine receptor agonist. 3-iodobenzyl-5'-N-methylcarboxamidoadenosine : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function is substituted by a 3-iodobenzyl group.	3.56	2	0	adenosines; monocarboxylic acid amide; organoiodine compound	adenosine A3 receptor agonist
kf 17837s KF 17837: adenosine A(2a) receptor antagonist; KF17837S is the equilibrium mixture of (E)- and (Z)-isomers	1.99	1	0
neurotensin (8-13) neurotensin (8-13): binds in human brain to the same site as neurotensin but with higher affinity	2.69	3	0
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
phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide: endogenous opioid antagonist octapeptide from bovine brain	3.86	11	0
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
n,n-dimethylarginine N,N-dimethylarginine: asymmetric dimethylarginine; do not confuse with N,N'-dimethylarginine. N(omega),N(omega)-dimethyl-L-arginine : A L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group.	3.48	1	1	dimethylarginine; guanidines; L-arginine derivative; non-proteinogenic L-alpha-amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor
3-(trifluoromethyl)-3-(3-iodophenyl)diazirine 3-(trifluoromethyl)-3-(3-iodophenyl)diazirine: photoactivatable probe, carbene-generating reagent	1.97	1	0
cp 66713 CP 66713: adenosine receptor antagonist; structure given in first source	1.98	1	0
dibutyryl cyclic-3',5'-cytidine monophosphate [no description available]	2.05	1	0
methotrexate [no description available]	10.06	9	6	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
6-(5-methylimidazol-1-yl)methyl-2-naphthoic acid hydrochloride 6-(5-methylimidazol-1-yl)methyl-2-naphthoic acid hydrochloride: RN given refers to HCl; RN for parent cpd not available 6/89	1.97	1	0
1-naphthylacetylspermine [no description available]	2.05	1	0	naphthalenes
gamma-carboline gamma-carboline: RN given refers to parent cpd; structure given in first source	3.31	1	0	pyridoindole
umifenovir umifenovir: an antiviral agent	2.66	2	0	indolyl carboxylic acid
safinamide safinamide: short-acting inhibitor of MOA-B; FCE 26743 is (S)-isomer, FCE 28073 is (R)-isomer; structure in first source	2.15	1	0	amino acid amide
carbapenems [no description available]	4.07	1	0
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.	3.53	8	0	adamantanes; monocarboxylic acid; naphthoic acid; phenols	apoptosis inducer; retinoic acid receptor gamma agonist
fulvene fulvene: structure. fulvene : An organic cyclic compound that consists of cyclopentadiene bearing a methylene substituent. The parent of the class of fulvenes.	2.06	1	0	fulvenes
quinone methide quinone methide: intermediate in eumelanin biosynthesis; structure given in first source. quinomethane : A methylidenecyclohexadienone, formally derived from a benzoquinone by replacement of one of the quinone oxygens by a methylidene group.	2.47	2	0	quinomethane
perrhenate perrhenate: RN given refers to cpd with MF of O4-Re	2.08	1	0	monovalent inorganic anion; rhenium oxoanion
sperm motility inhibitor 2 [no description available]	2.03	1	0
1,3,5-triaza-7-phosphaadamantane 1,3,5-triaza-7-phosphaadamantane: structure in first source	6.28	43	0
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.	4.57	9	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
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.	2.25	1	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.	3.19	1	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
n(w)-nitroarginine benzyl ester N(w)-nitroarginine benzyl ester: potent irreversible inhibitor of endothelium dependent relaxation	2.69	3	0
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
3-o-sulfogalactose 3-O-sulfogalactose: component of seminolipid on sperm membrane	2.01	1	0
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.	8.98	6	4	aromatic ether; cyclopropanes; fluoroquinolone antibiotic; pyrrolidinopiperidine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug
ruboxistaurin ruboxistaurin: inhibits protein kinase C beta; structure in first source	3.13	1	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.	2.48	2	0	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
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	2.05	1	0	oxygen hydride; oxygen radical; reactive oxygen species
naphthalenediimide naphthalenediimide: structure in first source	2.02	1	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.	3.44	1	1	organic sulfate salt
nps-568 N-(2-chlorophenylpropyl)-1-(3-methoxyphenyl)ethylamine: NPS-568 is the ((R), HCl salt)-isomer; calcimimetic compound and calcium-sensing receptor agonist	2.84	3	0
philanthotoxin 343 philanthotoxin 343: structure given in first source (see article's footnote); identical to philanthotoxin 433 except that the number of methylene groups between the respective amine moieties is 3,4,3 instead of 4,3,3	1.99	1	0	N-acyl-amino acid
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.	2.69	2	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
cyc 202 seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.	3.15	1	0	2,6-diaminopurines	antiviral drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
2-hydroxy-5-nitrobenzylthioguanosine [no description available]	2	1	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.	3.8	11	0	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).	3.01	4	0	amino acid zwitterion; angiotensin II	human metabolite
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.	3.4	7	0
sb 203580 [no description available]	2.46	2	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
zm 241385 ZM 241385: a high affinity radioligand selective for the A2a adenosine receptor	2.08	1	0	diamino-1,3,5-triazine
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2.98	4	0	divalent inorganic anion; phosphite ion
gvs 111 [no description available]	2.06	1	0
3-(piperidine-1-yl)propyl 4-amino-5-chloro-2-methoxybenzoate hydrochloride 3-(piperidine-1-yl)propyl 4-amino-5-chloro-2-methoxybenzoate hydrochloride: structure given in first source; a 5-HT(4) receptor antagonist	1.99	1	0
propargylglycine propargylglycine: RN given refers to cpd without isomeric designation; structure	2.08	1	0
attophos AttoPhos: fluorescent substrate for alkaline phosphatase; patent pending	1.98	1	0
baconipyrone c baconipyrone C: RN given for (alphaR-(alphaR(1(R),2R),betaR,gammaS,epsilonS))-isomer; isolated from Siphonariid mollusks; structure in first source	2.05	1	0
anabasine Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.	2.41	1	0	anabasine
4-n-butylresorcinol 4-n-butylresorcinol: structure in first source	2.13	1	0	resorcinols
muraglitazar muraglitazar: has glucose- and lipid-lowering activities; structure in first source; molecule composed of benzyloxazole-phenoxy-oxybenzylglycine-phenoxyl having structural analogy to PHENOXYBENZAMINE	4.04	2	0	1,3-oxazoles
tesaglitazar tesaglitazar: structure in first source	3.13	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.	3.44	1	1	carbamate ester; furofuran; sulfonamide	antiviral drug; HIV protease inhibitor
azd2563 posizolid: an antitubercular agent; structure in first source	4.18	2	0
deferasirox Deferasirox: A triazole and benzoate derivative that acts as a selective iron chelator. It is used in the management of chronic IRON OVERLOAD due to blood transfusion or non-transfusion dependent THALASSEMIA.. deferasirox : A member of the class of triazoles, deferasirox is 1,2,4-triazole substituted by a 4-carboxyphenyl group at position 1 and by 2-hydroxyphenyl groups at positions 3 and 5. An orally active iron chelator, it is used to manage chronic iron overload in patients receiving long-term blood transfusions.	2.08	1	0	benzoic acids; monocarboxylic acid; phenols; triazoles	iron chelator
sorafenib [no description available]	4.85	7	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
alagebrium alagebrium: an advanced glycation endproducts (AGE) cross-link breaker	2.25	1	0
santonin Santonin: Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. (From Merck, 11th ed.)	2.13	1	0	botanical anti-fungal agent; santonin	plant metabolite
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.	2.49	2	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.	2.39	2	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
estradiol 3-benzoate 17beta-estradiol 3-benzoate : A benzoate ester resulting from the formal condensation of benzoic acid with the phenolic hydroxy group of 17beta-estradiol.	2.13	1	0	17beta-hydroxy steroid; benzoate ester	estrogen receptor agonist; xenoestrogen
cortisone [no description available]	2.68	3	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
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.	3.47	1	1	2-nitrophenols; C-nitro compound; nitrotyrosine; non-proteinogenic alpha-amino acid
2-chlorobiphenyl 2-chlorobiphenyl: RN from Toxlit. 2-chlorobiphenyl : A monochlorobiphenyl carrying a single chloro substituent at position 2.. monochlorobiphenyl : A chlorobiphenyl carrying a single chloro substituent at unspecified position.. chlorobiphenyl : A chloroarene that consists of a biphenyl skeleton substituted by one or more chloro groups.	2.04	1	0	monochlorobiphenyl
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	2.03	1	0	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	3.35	1	0
estramustine Estramustine: A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.. estramustine : A carbamate ester obtained by the formal condensation of the hydroxy group of 17beta-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.	1.96	1	0	17beta-hydroxy steroid; carbamate ester; organochlorine compound	alkylating agent; antineoplastic agent; radiation protective agent
3,4-dihydroxyphenylpropionic acid 3,4-dihydroxyphenylpropionic acid: metabolite of caffeic acid; RN given refers to parent cpd; structure. 3-(3,4-dihydroxyphenyl)propanoic acid : A monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity.	2.03	1	0	(dihydroxyphenyl)propanoic acid	antioxidant; human xenobiotic metabolite
tris(2-pyridylmethyl)amine tris(2-pyridylmethyl)amine: structure in first source	2.06	1	0
nsc668394 [no description available]	4.14	4	0
nsc 680410 NSC 680410: a bcr/abl kinase inhibitor; structure in first source	5.84	29	0
bortezomib [no description available]	2.99	4	0	amino acid amide; L-phenylalanine derivative; pyrazines	antineoplastic agent; antiprotozoal drug; protease inhibitor; proteasome inhibitor
jib-04 JIB-04: structure in first source	2.31	1	0
mrs 1191 MRS 1191: a selective A3 adenosine receptor antagonist; structure given in first source	2.02	1	0	cinnamate ester
dihydropyridines Dihydropyridines: Pyridine moieties which are partially saturated by the addition of two hydrogen atoms in any position.	2.7	3	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
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.	4.37	4	0
carboplatin [no description available]	2.54	2	0
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.	1.99	1	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.	2.07	1	0
mannose-6-phosphate beta-D-mannose 6-phosphate : A D-mannopyranose 6-phosphate with a beta-configuration at the anomeric position.	2.13	1	0	D-mannopyranose 6-phosphate
bradykinin [no description available]	5.4	14	1	oligopeptide	human blood serum metabolite; vasodilator agent
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.	1.96	1	0	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
7-dehydrocholesterol [no description available]	2.04	1	0	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; Delta(5),Delta(7)-sterol	human metabolite; 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.	2.08	1	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
tosylphenylalanyl chloromethyl ketone Tosylphenylalanyl Chloromethyl Ketone: An inhibitor of Serine Endopeptidases. Acts as alkylating agent and is known to interfere with the translation process.. N-tosyl-L-phenylalanyl chloromethyl ketone : The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.	2.15	1	0	alpha-chloroketone; sulfonamide	alkylating agent; serine proteinase inhibitor
pentostatin Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.. pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.	2.4	2	0	coformycins	antimetabolite; antineoplastic agent; Aspergillus metabolite; bacterial metabolite; EC 3.5.4.4 (adenosine deaminase) inhibitor
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.	2.02	1	0	guanidines; L-arginine derivative; N-nitro compound; non-proteinogenic L-alpha-amino acid
adenosine 5'-o-(3-thiotriphosphate) adenosine 5'-O-(3-thiotriphosphate): RN given refers to cpd with unspecified locant for thio group; see also records for 1-thio & 2-thio-isomers. adenosine 5'-[gamma-thio]triphosphate : A nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur.	2	1	0	nucleoside triphosphate analogue
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.	2.07	1	0	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen
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.	1.97	1	0	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
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.	3.44	1	1	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor
hyperforin hyperforin: a prenylated acylphloroglucinol derivative; antibiotic component of novoimanine; psychoactive agent in St. John's wort; Russian; structure;. hyperforin : A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.	2.01	1	0
miglitol [no description available]	2.49	2	0	piperidines
linezolid [no description available]	3.56	2	0	acetamides; morpholines; organofluorine compound; oxazolidinone	antibacterial drug; protein synthesis 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)	2.58	2	0
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.	1.98	1	0	tripeptide
devazepide Devazepide: A derivative of benzodiazepine that acts on the cholecystokinin A (CCKA) receptor to antagonize CCK-8's (SINCALIDE) physiological and behavioral effects, such as pancreatic stimulation and inhibition of feeding.. devazepide : An indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used for treatment of gastrointestinal disorders.	2.03	1	0	1,4-benzodiazepinone; indolecarboxamide	antineoplastic agent; apoptosis inducer; cholecystokinin antagonist; gastrointestinal drug
ao 128 AO 128: alpha-glucosidase inhibitor; structure given in first source	5.99	3	3	organic molecular entity
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	7.35	128	0	cyclodextrin
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.	3.15	5	0	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.	2.94	4	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.	2.39	2	0	cyclodextrin
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).	2.04	1	0	retinol; vitamin A	human metabolite; mouse metabolite; plant metabolite
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.	2.11	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
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.	3.11	5	0	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
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.	2.71	3	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.	2.11	1	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
tetragastrin Tetragastrin: L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalaninamide. The C-terminal tetrapeptide of gastrin. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin.. tetragastrin : A tetrapeptide composed of L-tryptophan, L-methione, L-aspartic acid and L-phenylalaninamide residues joined in sequence.	3.25	6	0	peptidyl amide; tetrapeptide	anxiogenic; human 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.	2.07	1	0	geranylgeranyl diphosphate	mouse metabolite
apstatin apstatin: inhibits aminopeptidase P; structure given in first source	2.05	1	0
isofagomine [no description available]	2.03	1	0	piperidines
adenosine-5'-(n-ethylcarboxamide) Adenosine-5'-(N-ethylcarboxamide): A stable adenosine A1 and A2 receptor agonist. Experimentally, it inhibits cAMP and cGMP phosphodiesterase activity.. N-ethyl-5'-carboxamidoadenosine : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group.	2.71	3	0	adenosines; monocarboxylic acid amide	adenosine A1 receptor agonist; adenosine A2A receptor agonist; antineoplastic agent; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; vasodilator agent
prostaglandin d2 Prostaglandin D2: The principal cyclooxygenase metabolite of arachidonic acid. It is released upon activation of mast cells and is also synthesized by alveolar macrophages. Among its many biological actions, the most important are its bronchoconstrictor, platelet-activating-factor-inhibitory, and cytotoxic effects.. prostaglandin D2 : A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).	2.13	1	0	prostaglandins D	human metabolite; mouse 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.	2.43	2	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
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.	2.47	2	0	N-[2-(4-bromocinnamylamino)ethyl]isoquinoline-5-sulfonamide
afimoxifene afimoxifene : A tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen.	2.43	2	0	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite
imidazolidines [no description available]	2.25	1	0	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
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	6.43	6	0
bm 212 BM 212: anti-mycobacterial agent; structure in first source	2.52	2	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)	1.95	1	0	actinomycin	mutagen
5-carboxy-8-hydroxyquinoline 5-carboxy-8-hydroxyquinoline: a JmjC histone demethylase inhibitor; structure in first source	2.31	1	0	quinolines
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.	2.03	1	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
enkephalin, leucine Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.	3.61	9	0	pentapeptide; peptide zwitterion	analgesic; delta-opioid receptor agonist; human metabolite; mu-opioid receptor agonist; neurotransmitter; rat metabolite
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.	4.37	4	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
u 100480 U 100480: structure given in first source	5.02	4	0
posaconazole [no description available]	2.11	1	0	aromatic ether; conazole antifungal drug; N-arylpiperazine; organofluorine compound; oxolanes; triazole antifungal drug; triazoles	trypanocidal drug
nsc305787 [no description available]	4.85	9	0
laninamivir laninamivir: an antiviral agent	2.05	1	0	acetamides
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)	2.17	1	0
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.	1.99	1	0	organic sodium salt	NMR chemical shift reference compound
zn(ii)-phthalocyanine [no description available]	2.31	1	0	metallophthalocyanine; zinc tetrapyrrole	fluorochrome
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.	2.67	3	0	organic sodium salt	anti-inflammatory agent; antipyretic; antirheumatic drug; cyclooxygenase 3 inhibitor; non-narcotic analgesic; peripheral nervous system drug; prodrug
11-mercaptoundecanoic acid [no description available]	2.03	1	0
calix(4)arene calix(4)arene: a cyclophane consisting of four phenolic units linked by methylene groups; structure in first source	2.03	1	0
carbenoxolone sodium Carbenoxolone: An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity.	2.54	2	0	triterpenoid
glycosides [no description available]	4.07	4	0
chalcone trans-chalcone : The trans-isomer of chalcone.	2.47	2	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)	2.75	3	0	isomethyleugenol
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2.11	1	0	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.02	1	0	stilbene
s 1033 [no description available]	2.17	1	0	(trifluoromethyl)benzenes; imidazoles; pyridines; pyrimidines; secondary amino compound; secondary carboxamide	anticoronaviral agent; antineoplastic agent; tyrosine kinase inhibitor
dodecylphosphocholine dodecylphosphocholine: phospholipase A2 inhibitor; RN refers to chloride. dodecylphosphocholine : A phosphocholine that is the monododecyl ester of phosphocholine	7.06	1	0	phosphocholines	detergent
fludarabine [no description available]	2.02	1	0	purine nucleoside
sesquiterpenes [no description available]	2.44	2	0
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.	2.36	2	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
thioinosine Thioinosine: Sulfhydryl analog of INOSINE that inhibits nucleoside transport across erythrocyte plasma membranes, and has immunosuppressive properties. It has been used similarly to MERCAPTOPURINE in the treatment of leukemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p503)	2	1	0
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	1.95	1	0	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
rhododendrol rhododendrol: structure in first source	2.13	1	0
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	2.11	1	0	thiazolidinone
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.	3.41	2	0	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	2.02	1	0
fatostatin fatostatin: inhibits activation of SREBP; structure in first source	3.17	1	0	thiazoles
benzotript benzotript: anti-gastrinic; active group is amide; structure	2	1	0
thiosemicarbazide thiosemicarbazide: glutamate decarboxylase antagonist; structure given in first source. hydrazinecarbothioamide : A member of the class of thioureas that is thiourea in which a hydrogen of one of the amino groups is replaced by an amino group.	2.1	1	0	hydrazines; thiocarboxamide; thioureas
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.	3.73	10	0	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	2.25	1	0	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
thioacetamide Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.	2.89	4	0	thiocarboxamide	hepatotoxic agent
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.	4.61	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	2.31	1	0
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.	3.42	1	1	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
tamoxifen [no description available]	2.71	3	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
nadp [no description available]	2.07	1	0
t 0070907 T 0070907: a PPARgamma antagonist; structure in first source	2.08	1	0	carbonyl compound; organohalogen compound
adhesamine adhesamine: synthetic diaryldispirotripiperazine that targets selective cell-surface glycosaminoglycans,especially heparan sulfate, for increasing cell adhesion and growth; a useful reagent for culturing neuronal cells	3.17	1	0
artemotil artemotil: structure given in first source; RN given refers to cpd without isomeric designation	2.04	1	0	artemisinin derivative
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.	2.1	1	0	cyclodepsipeptide; macrocycle	antimicrobial agent; antiviral agent; bacterial metabolite; potassium ionophore
6-mercapto-9-(tetrahydro-2-furyl)purine [no description available]	1.96	1	0	purines; thiocarbonyl compound
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.	1.98	1	0	C-nitro compound; furans; organic sulfide; tertiary amino compound	anti-ulcer drug; drug allergen; environmental contaminant; H2-receptor antagonist; xenobiotic
u 0126 U 0126: protein kinase kinase inhibitor; structure in first source	2.08	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
sq-641 SQ-641: a MurX inhibitor with antitubercular activity; structure in first source	4.2	2	0
6-methyl-2-(phenylethynyl)pyridine 6-methyl-2-(phenylethynyl)pyridine: an mGlu5 antagonist. 2-methyl-6-(phenylethynyl)pyridine : A methylpyridine that coinsists of 2-methylp[yridine bearing an additional phenylethynyl group at position 6. Potent and highly selective non-competitive antagonist at the mGlu5 receptor subtype (IC50 = 36 nM) and a positive allosteric modulator at mGlu4 receptors. Centrally active following systemic administration in vivo. Reverses mechanical hyperalgesia in the inflamed rat hind paw.	2.05	1	0	acetylenic compound; methylpyridines	anxiolytic drug; metabotropic glutamate receptor antagonist
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.	2.04	1	0	alkali metal atom
cobaltous chloride cobaltous chloride: RN given refers to unlabeled cpd; RN in Chemline for cobalt trichloride: 10241-04-0; RN for 60-labeled cpd: 14543-09-0; RN for 57-labeled cpd: 164113-89-1; RN for 58-labeled cpd: 29377-09-1; structure. cobalt dichloride : A cobalt salt in which the cobalt metal is in the +2 oxidation state and the counter-anion is chloride. It is used as an indicator for water in desiccants.	2.52	2	0	cobalt salt; inorganic chloride	allergen; calcium channel blocker; sensitiser; two-colour indicator
raclopride Raclopride: A substituted benzamide that has antipsychotic properties. It is a dopamine D2 receptor (see RECEPTORS, DOPAMINE D2) antagonist.	2.69	3	0	salicylamides
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.	2.08	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]	7.72	3	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
1,2-bis(2-aminophenoxy)ethane n,n,n',n'-tetraacetic acid acetoxymethyl ester [no description available]	2.25	1	0
peptidoglycan pentapeptide-mdap3 peptidoglycan pentapeptide-mDap3: peptide portion of peptidoglycan-mDap3 in Gram-negative bacteria	2.41	2	0
thioperamide thioperamide: structure given in first source; histamine H3 receptor antagonist	2.41	2	0	primary aliphatic amine
sch 23390 SCH 23390: a selective D1-receptor antagonist. SCH 23390 : A benzazepine that is 2,3,4,5-tetrahydro-3-benzazepine bearing a phenyl substituent at position 1, a methyl substituent at position 3, a chloro substituent at position 7 and a hydroxy substituent at position 8.	2.48	2	0	benzazepine
zelandopam zelandopam: structure given in first source	1.98	1	0
ethylphenidate ethylphenidate: structure given in first source	2.15	1	0
cholecystokinin pentapeptide cholecystokinin pentapeptide: RN given refers to all (L)-isomer	1.99	1	0
cholecystokinin (26-33) cholecystokinin (26-33): cholecystokinin receptor antagonists	1.98	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.	3.3	6	0
h-tyrosyl-cyclo(cysteinyl-phenylalanyl-penicillaminyl)-oh H-tyrosyl-cyclo(cysteinyl-phenylalanyl-penicillaminyl)-OH: a cyclic delta receptor selective tetrapeptide; RN given is for D-penicillamine	2.03	1	0
tribendimidine tribendimidine: structure given in first source	2.46	2	0
2-(4-(2-carboxyethyl)phenethylamino)-5'-n-ethylcarboxamidoadenosine 2-(4-(2-carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine: A2 adenosine receptor agonist; structure given in first source. CGS-21680 : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and the hydrogen at position 2 on the adenine is replaced by a 4-(2-carboxyethyl)phenethylamino group.	2.47	2	0	adenosines; dicarboxylic acid monoamide; monocarboxylic acid	adenosine A2A receptor agonist; anti-inflammatory agent
chromeceptin chromeceptin: inhibits Igf2 at the transcriptional level; structure in first source	3.17	1	0
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline 2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline: structure given in first source; neuroprotectant for cerebral ischemia; AMPA receptor antagonist	2.1	1	0	naphthalenes; sulfonic acid derivative
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	3.3	6	0
gw 7647 GW 7647: a PPAR-alpha agonist; structure in first source. GW 7647 : A monocarboxylic acid that is 2-(phenylsulfanyl)isobutyric acid in which the phenyl group is substituted at the para- position by a 3-aza-7-cyclohexylhept-1-yl group in which the nitrogen is acylated by a (cyclohexylamino)carbonyl group.	2.08	1	0	aryl sulfide; monocarboxylic acid; ureas	PPARalpha agonist
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.	2.13	1	0	organic sodium salt	detergent; protein denaturant
sto 609 STO 609: structure in first source	2.07	1	0	naphthoic acid
16-mercaptohexadecanoic acid [no description available]	2.03	1	0
zinc protoporphyrin ix [no description available]	7.31	1	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.	1.96	1	0
minoxidil sulfate ester minoxidil sulfate ester: metabolite of minoxidil; structure given in first source	2.38	2	0
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	3.1	5	0
jhw 015 [no description available]	3.25	1	0	indolecarboxamide
am 630 iodopravadoline: an aminoalkylindole; a competitive cannabinoid receptor antagonist; structure given in first source	3.25	1	0	N-acylindole
sc 560 SC560 : A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3 and 5 by 4-methoxyphenyl, trifluoromethyl and 4-chlorophenyl groups, respectively. Unlike many members of the diaryl heterocycle class of cyclooxygenase (COX) inhibitors, SC-560 is selective for COX-1.	2.13	1	0	aromatic ether; monochlorobenzenes; organofluorine compound; pyrazoles	angiogenesis modulating agent; antineoplastic agent; apoptosis inducer; cyclooxygenase 1 inhibitor; non-steroidal anti-inflammatory drug
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.	2.25	1	0
osteoprotegerin Osteoprotegerin: A secreted member of the TNF receptor superfamily that negatively regulates osteoclastogenesis. It is a soluble decoy receptor of RANK LIGAND that inhibits both CELL DIFFERENTIATION and function of OSTEOCLASTS by inhibiting the interaction between RANK LIGAND and RECEPTOR ACTIVATOR OF NUCLEAR FACTOR-KAPPA B.	2.15	1	0	long-chain fatty acid
1-cyclohexyl-3-dodecylurea [no description available]	2	1	0
rhodamine 123 Rhodamine 123: A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30). rhodamine 123(1+) : A cationic fluorescent dye derived from 9-phenylxanthene.	2.04	1	0	organic cation; xanthene dye	fluorochrome
bromantane bromantane: a derivative of 2-aminoadamantane; a CNS stimulant	3.1	1	0
mrs2159 MRS2159: an antagonist of both P2X1 and P2X7 receptors	2.11	1	0
sq 109 N-geranyl-N'-(2-adamantyl)ethane-1,2-diamine: has antitubercular activity	13.62	42	6
ku 55933 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one: specific inhibitor of the ataxia-telangiectasia mutated kinase ATM; structure in first source	2.1	1	0
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.	5.19	10	0	sphing-4-enine	human metabolite; mouse metabolite
quercetin [no description available]	2.41	1	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
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.	2.03	1	0	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.	4.45	1	1	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
arachidonyltrifluoromethane arachidonyltrifluoromethane: structure given in first source; inhibits 85-kDa phospholipase A2. AACOCF3 : A fatty acid derivative that is arachidonic acid in which the OH part of the carboxy group has been replaced by a trifluoromethyl group	2.07	1	0	fatty acid derivative; ketone; olefinic compound; organofluorine compound	EC 3.1.1.4 (phospholipase A2) inhibitor
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.	2.66	2	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	2.47	2	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
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.	2.07	1	0	retinal	chromophore; human metabolite; mouse 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.	2.38	2	0	hydroxycoumarin	antineoplastic agent; hyaluronic acid synthesis inhibitor
daphnetin [no description available]	2.31	1	0	hydroxycoumarin
8,11,14-eicosatrienoic acid 8,11,14-Eicosatrienoic Acid: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.. all-cis-icosa-8,11,14-trienoic acid : An icosatrienoic acid having three cis double bonds at positions 8, 11 and 14.	3.95	12	0	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
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.	2.04	1	0	hydroxy seco-steroid; seco-ergostane; vitamin D	bone density conservation agent; nutraceutical; plant metabolite; rodenticide
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.	4.4	4	1	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.	2.9	4	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
genistein [no description available]	2.05	1	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
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	2.13	1	0	alpha-humulene
ellagic acid [no description available]	1.99	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
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.48	2	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	4.45	1	1	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
n,n-dimethylsphingenine N,N-dimethylsphingosine: a sphingosine kinase inhibitor. N,N-dimethylsphingosine : A sphingoid that is sphingosine in which the two amino hydrogens are replaced by methyl groups.	2.17	1	0	aminodiol; sphingoid; tertiary amino compound	EC 2.7.1.91 (sphingosine kinase) inhibitor; metabolite
thromboxane b2 Thromboxane B2: A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).. thromboxane B2 : A member of the class of thromboxanes B that is (5Z,13E)-thromboxa-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15.	2.08	1	0	thromboxanes B	human metabolite; mouse metabolite
20-hydroxy-5,8,11,14-eicosatetraenoic acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid: stimulator of renal sodium, potassium atpase; RN given is for the (all-Z) isomer. 20-HETE : A HETE that consists of arachidonic acid bearing a hydroxy substituent at position 20.	2.02	1	0	HETE; hydroxy monocarboxylic acid	human metabolite; mouse metabolite
5,6-epoxy-8,11,14-eicosatrienoic acid 5,6-epoxy-8,11,14-eicosatrienoic acid: RN given refers to cpd without isomeric designation. 5,6-EET : An EET obtained by formal epoxidation of the 5,6-double bond of arachidonic acid.	2.1	1	0	EET	mouse metabolite
8,9-epoxyeicosatrienoic acid 8,9-epoxyeicosatrienoic acid: RN given refers to cpd without isomeric designation. 8,9-EET : An EET obtained by formal epoxidation of the 8,9-double bond of arachidonic acid.	2.1	1	0	EET	mouse metabolite
menaquinone 6 menaquinone 6: RN given refers to (all-E)-isomer	2.1	1	0
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	4.98	8	0	sphingoid 1-phosphate	mouse metabolite; signalling molecule; sphingosine-1-phosphate receptor agonist; T-cell proliferation inhibitor; vasodilator agent
codeine [no description available]	1.95	1	0	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic
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.	2.72	3	0	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
vitamin k 1 Vitamin K 1: A family of phylloquinones that contains a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Members of this group of vitamin K 1 have only one double bond on the proximal isoprene unit. Rich sources of vitamin K 1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity.. phylloquinone : A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.	2.04	1	0	phylloquinones; vitamin K	cofactor; human metabolite; plant metabolite
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.	2.41	1	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.	7.76	3	0	cyclodextrin
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.	3.16	5	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
beta-funaltrexamine beta-funaltrexamine: RN given refers to parent cpd(E)-isomer; structure given in first source	2.1	1	0	morphinane alkaloid
bibp 3226 BIBP 3226: a selective non-peptide neuropeptide Y Y1 receptor antagonist; structure given in first source; BIBP-3435 is the S-enantiomer	2.79	3	0
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.	2.15	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
endomorphin 1 endomorphin 1: isolated from bovine brain	2.71	3	0	oligopeptide
endomorphin 2 endomorphin 2: isolated from bovine brain	2.73	3	0
kallidin Kallidin: A decapeptide bradykinin homolog cleaved from kininogen by kallikreins. It is a smooth-muscle stimulant and hypotensive agent that acts by vasodilatation.	1.98	1	0	peptide
gv 150013x GV 150013X: CCK-B receptor antagonist; structure in first source	3.8	11	0	benzodiazepine
l 365260 L 365260: a CCK-B antagonist; structure given in first source; potent & selective CCK-B & gastrin receptor ligand; L 365260 and L 365346 are (R)- and (S)-stereoisomers, respectively	2.69	3	0	benzodiazepine
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.	2.15	1	0
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.	4.7	3	2	phenylalanine derivative
neurokinin b Neurokinin B: A mammalian neuropeptide of 10 amino acids that belongs to the tachykinin family. It is similar in structure and action to SUBSTANCE P and NEUROKININ A with the ability to excite neurons, dilate blood vessels, and contract smooth muscles, such as those in the URINARY BLADDER and UTERUS.	2.07	1	0	polypeptide
sq 29548 SQ 29548: SQ-26538 is the ((1S-1alpha,2beta(5Z),3beta(1E,3R*),4alpha))-isomer; thromboxane A2 antagonist; thromboxane receptor antagonist	2.13	1	0
ro 41-5253 Ro 41-5253: a synthetic retinoid with antiviral activity; a selective RAR alpha antagonist; structure given in first source. Ro 41-5253 : A thiochromane that is 3,4-dihydro-2H-1-benzothiopyran S,S-dioxide in which the hydrogens at position 4 are both replaced by methyl groups, the hydrogens at position 7 is replaced by a heptyloxy group, while the hydrogen at position 6 is replaced by a 1-phenylprop-1-en-2-yl group, the phenyl group of which is substituted at the para position by a carboxy group. It is a selective antagonist for retinoic acid receptor alpha.	2.55	2	0	aromatic ether; benzoic acids; sulfone; thiochromane	apoptosis inducer; retinoic acid receptor alpha antagonist
kn 93 KN 93: reduces dopamine content in PC12h cells. KN-93 : A sulfonamide resulting from the formal condensation of p-methoxybenzenesulfonic acid with the anilino nitrogen of 2-(aminomethyl)-N-(2-hydroxyethyl)aniline in which the hydrogens of the primary amino group have been replaced by methyl and p-chlorocinnamyl groups. KN-93 is a selective inhibitor of Ca(2+)/calmodulin-dependent protein kinase II.	2.25	1	0	monochlorobenzenes; monomethoxybenzene; primary alcohol; sulfonamide; tertiary amino compound	EC 2.7.11.17 (Ca(2+)/calmodulin-dependent protein kinase) inhibitor; geroprotector
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.	1.97	1	0	phosphatidylcholine(1+)
lead Lead: A soft, grayish metal with poisonous salts; atomic number 82, atomic weight 207.2, symbol Pb.	2.46	2	0	carbon group element atom; elemental lead; metal atom	neurotoxin
tin [no description available]	2.44	2	0	carbon group element atom; elemental tin; metal atom	micronutrient
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.	2.08	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
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	1	0
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	2.4	2	0	alkali metal atom
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.	2.71	3	0	alkaline earth metal atom; elemental barium
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.	1.99	1	0	alkali metal atom
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.43	2	0	boron group element atom; elemental aluminium; metal atom
bismuth Bismuth: A metallic element that has the atomic symbol Bi, and atomic number 83. Its principal isotope is Bismuth 209.	2.05	1	0	metal atom; pnictogen
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)	2.98	4	0	metalloid atom; pnictogen	micronutrient
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.	3.02	4	0	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
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.	3.87	2	1	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
ridogrel [no description available]	1.97	1	0	(trifluoromethyl)benzenes
indinavir sulfate Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.	3.44	1	1	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.	8.37	6	0	chalcogen; nonmetal atom	macronutrient
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.	2.1	1	0	alkatriene	fluorochrome
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.	8.43	14	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).	2.52	2	0	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug
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).	2.17	1	0	1,2-diacyl-sn-glycero-3-phosphocholine; phosphatidylcholine 28:0; tetradecanoate ester	antigen; mouse metabolite
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.	2.74	3	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].	2.03	1	0	carbon group element atom; metalloid atom; nonmetal atom
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.	2.53	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.	2.06	1	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.	2.03	1	0	morphinane alkaloid	mu-opioid receptor agonist; opioid analgesic; prodrug
ramiprilat ramiprilat : A dipeptide that is the active metabolite of ramipril. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.	3.43	1	1	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid; dipeptide	bradykinin receptor B2 agonist; cardioprotective agent; drug metabolite; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor
phytochlorin phytochlorin: RN given refers to (2S-trans)-isomer; structure given in the first source	2.61	2	0
norbinaltorphimine norbinaltorphimine: kappa opiate receptor antagonist; structure given in first source	2.49	2	0	isoquinolines
enkephalin, ala(2)-mephe(4)-gly(5)- Enkephalin, Ala(2)-MePhe(4)-Gly(5)-: An enkephalin analog that selectively binds to the MU OPIOID RECEPTOR. It is used as a model for drug permeability experiments.	2.71	3	0
neuromedin c neuromedin C: decapeptide isolated from porcine spinal cord; corresponds to the C-terminal decapeptide of gastrin-releasing peptide; bombesin-like peptide; RN given refers to all (L)-isomer	2.06	1	0
docosapentaenoic acid docosapentaenoic acid : Any straight-chain, C22 fatty acid having five C=C double bonds.. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid : The all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 7-, 10-, 13-, 16- and 19-positions.	2.13	1	0	docosapentaenoic acid; omega-3 fatty acid	algal metabolite; human metabolite
naltrindole naltrindole: delta opioid receptor antagonist	2.1	1	0	isoquinolines
carbocyanines Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.	2.51	2	0	cyanine dye; organic iodide salt	fluorochrome
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.	2.1	1	0	ammonium salt; inorganic sulfate salt	fertilizer
3,5-dihydroxy-4'-methoxystilbene 4'-methoxyresveratrol: has anti-inflammatory effects in cell culture model	2.02	1	0
coomassie brilliant blue [no description available]	2.25	1	0
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.	8.53	8	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
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.	2.11	1	0	chalcogen; metalloid atom
selenourea [no description available]	7.41	1	0
aluminum hydroxide, magnesium hydroxide, drug combination aluminum hydroxide, magnesium hydroxide, simethicone drug combination: antacid contains aluminum hydroxide, magnesium hydroxide and simethicone; mylanta II contains aluminum/magnesium hydroxide mixture	3.59	1	1
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.	3.53	8	0	maleate salt; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
simethicone Simethicone: A poly(dimethylsiloxane) which is a polymer of 200-350 units of dimethylsiloxane, along with added silica gel. It is used as an antiflatulent, surfactant, and ointment base.	3.59	1	1
bongkrekic acid Bongkrekic Acid: An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of MITOCHONDRIAL ADP, ATP TRANSLOCASES. Specifically, it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.. bongkrekic acid : A tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group. It is produced by the bacterium Burkholderia gladioli and implicated in outbreaks of food-borne illness involving coconut and corn-based products in Indonesia and China.	2.11	1	0	ether; olefinic compound; tricarboxylic acid	apoptosis inhibitor; ATP/ADP translocase inhibitor; bacterial metabolite; EC 2.5.1.18 (glutathione transferase) inhibitor; toxin
vitamin a2 vitamin A2: RN given refers to cpd without isomeric designation. all-trans-3,4-didehydroretinol : A retinoid derived from 3,4-desaturation of the beta-ionone ring of all-trans-retinol.	2.04	1	0	retinoid; vitamin A	human xenobiotic metabolite; marine xenobiotic metabolite; mouse metabolite
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.	2.61	2	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
biotin-11-dutp biotin-11-dUTP: used in detection of sickle cell anemia	1.97	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.	2.11	1	0	fluorenes; monochlorobenzenes; secondary alcohol; tertiary amine	antimalarial
14,15-episulfide eicosatrienoic acid 14,15-episulfide eicosatrienoic acid: inhibits ionophore but not thrombin-induced platelet aggregation	2.03	1	0
sr 31747 SR 31747: a sigma receptor antagonist and steroid isomerase inhibitor with immunosuppressive and anti-inflammatory activities; structure given in first source	4.03	1	0
pd 136450 PD 136450: gastrin receptor antagonist; dipeptoid which resembles the carboxy-terminal moiety of gastrin	1.99	1	0
lg100754 LG 100754: retinoic acid receptors antagonist & agonist; a mixed function retinoid whose activity is dimer-selective; structure given in first source	2.21	1	0
riligustilide riligustilide: isolated from Angelica sinensis; structure in first source	3.35	1	0
vernoleate vernolic acid : A monounsaturated epoxy fatty acid composed of cis-9-octadecenoic acid having a 12,13-epoxy group.. (+)-vernolic acid : An optically active form of vernolic acid having (12S,13R)-configuration.	2.25	1	0	oxylipin; vernolic acid
a 315675 [no description available]	2.05	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.	2.01	1	0	galactosylceramide sulfate; N-acyl-beta-D-galactosylsphingosine
oxepins Oxepins: Compounds based on a 7-membered heterocyclic ring including an oxygen. They can be considered a medium ring ether. A natural source is the MONTANOA plant genus. Some dibenzo-dioxepins, called depsidones, are found in GARCINIA plants.	2.11	1	0
glycylproline 4-nitroanilide glycylproline 4-nitroanilide: substrate for dipeptidyl peptidase IV	2.03	1	0
sudoterb sudoterb: an antibacterial active against M. tuberculosis; structure in first source	5.05	2	0
opc-67683 OPC-67683: an antitubercular agent	5.57	5	0	piperidines
tanespimycin CP 127374: analog of herbimycin A	2.03	1	0	1,4-benzoquinones; ansamycin; carbamate ester; organic heterobicyclic compound; secondary amino compound	antineoplastic agent; apoptosis inducer; Hsp90 inhibitor
a 77636 A 77636: structure given in first source; a selective dopamine D1 receptor agonist. (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydroisochromene-5,6-diol : An isochromene that is 3,4-dihydroisochromene-5,6-diol bearing additional aminomethyl and 1-adamantyl substituents at positions 1 and 3 respectively (the 1R,3S-diastereomer). Potent and selective dopamine D1-like receptor agonist (pEC50 values are 8.97 and < 5 for D1-like and D2-like receptors respectively). Displays anti-Parkinsonian activity following oral administration in vivo.	6.97	37	0	adamantanes; catechols; isochromenes; primary amino compound	antiparkinson drug; dopamine agonist
am 404 [no description available]	2.08	1	0	anilide
iem 1460 IEM 1460: structure in first source	5.06	39	0
nifurtimox Nifurtimox: A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.	7.21	1	0	nitrofuran antibiotic
ergoline Ergolines: A series of structurally-related alkaloids that contain the ergoline backbone structure.. ergoline : An indole alkaloid whose structural skeleton is found in many naturally occurring and synthetic ergolines which are known to bind to neurotransmitter receptors, such as dopamine, noradrenaline and serotonin receptors and function as unselective agonists or antagonists at these receptors.	2.39	2	0	diamine; ergoline alkaloid; indole alkaloid fundamental parent; indole alkaloid; organic heterotetracyclic compound
platensimycin platensimycin: has antidiabetic and antisteatotic activities; a pentacyclic ketolide (structurally similar to adamantane) connected by an amide bond to 3-amino-2,4-dihydroxybenzoic acid; inhibits cellular lipid biosynthesis; discovered while screening compounds from Streptomyces platensis bacteria in a South African soil sample with S. aureus bacteria deficient in FabF protein; structure in first source. platensimycin : A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the oxatetracyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase.	9.55	106	0	aromatic amide; cyclic ether; cyclic ketone; dihydroxybenzoic acid; monocarboxylic acid amide; polycyclic cage	antibacterial agent; antimicrobial agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor
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).	2.03	1	0	nucleoside 3',5'-cyclic phosphorothioate
etonogestrel [no description available]	3.19	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin
eleutherobin eleutherobin: structure in first source	2.21	1	0
vildagliptin [no description available]	24.9	592	181	amino acid amide
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.	2.31	1	0	beta-D-glucoside; rebaudioside; tetracyclic diterpenoid	sweetening agent
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2	1	0	borneol
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.	3.71	9	0	penicillanic acids
sidnocarb sidnocarb: Russian drug; structure	2.44	2	0
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.	2.39	2	0	biguanides; monochlorobenzenes	antibacterial agent; antiinfective agent
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	7.52	2	0
thioacetazone Thioacetazone: A thiosemicarbazone that is used in association with other antimycobacterial agents in the initial and continuation phases of antituberculosis regimens. Thiacetazone containing regimens are less effective than the short-course regimen recommended by the International Union Against Tuberculosis and are used in some developing countries to reduce drug costs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p217). thiosemicarbazone : A hydrazone resulting from the formal condensation of an aldehyde or ketone with the non-thioacylated nitrogen of thiosemicarbazide or its substituted derivatives.	2.31	1	0
tri-cyclen [no description available]	3.46	1	1
osu 6162 OSU 6162: reduces levodopa-induced dyskinesias without inducing akinesia	2	1	0
az 11645373 AZ 11645373: InChIKey: VQEHBLGYANQWEA-UHFFFAOYSA-N	2.05	1	0
dinapsoline dinapsoline: a dopamine D(1) agonist; structure in first source	2.03	1	0
bemethyl bemethyl: 2-mercaptobenzimidazole deriv.; alkylating agent and mutagen antagonist	2.52	2	0
sincalide Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.	3.1	5	0	oligopeptide
hemantane hemantane: an antiparkinsonian drug	3.96	12	0
2-propyl-4,5,5a,6,7,11b-hexahydro-3-thia-5-azacyclopent-1-ena(c)phenanthrene-9,10-diol A 86929: a selective dopamine D1 agonists; structure given in first source	2	1	0
gw791343 GW791343: inhibits human P2X-7 receptor but is a positive allosteric modulator of rat P2X-7 receptor; structure in first source	2.05	1	0
dc 107 leinamycin: a thiazole containing macrolide characterized by an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro fused to an 18 member macrolactam ring; isolated from Streptomyces; MF C22-H26-N2-O6-S3; possible DNA alkylator; the leinamycin biosynthetic gene cluster from Streptomyces atroolivaceus S-140 consists of two polyketide synthases genes	3.31	1	0	dithiolanes
pentagastrin Pentagastrin: A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid.	2.4	2	0	organic molecular entity
sm 346 SM 346: 2-mercaptobenzimidazole derivative	2.76	3	0
adarotene adarotene: structure in first source	7.19	27	1
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).	4.84	7	1	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
eslicarbazepine [no description available]	2.31	1	0	dibenzooxazepine
dapagliflozin [no description available]	16.26	51	26	aromatic ether; C-glycosyl compound; monochlorobenzenes	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
iem 1754 IEM 1754: structure given in first source	4.03	14	0
bay36-7620 BAY36-7620: a potent non-competitive mGlu1 receptor antagonist with inverse agonist activity. ; structure in first source	2.01	1	0
sr 48527 SR 48527: SR 48527 is the S-enantiomer; SR-49711 is the R-enantiomer	1.99	1	0
pd 140548 [no description available]	1.99	1	0
tofacitinib tofacitinib : A pyrrolopyrimidine that is pyrrolo[2,3-d]pyrimidine substituted at position 4 by an N-methyl,N-(1-cyanoacetyl-4-methylpiperidin-3-yl)amino moiety. Used as its citrate salt to treat moderately to severely active rheumatoid arthritis.	7.46	14	0	N-acylpiperidine; nitrile; pyrrolopyrimidine; tertiary amino compound	antirheumatic drug; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
sr 142948a SR 142948A: structure in first source	4.75	30	0
pasireotide pasireotide : A six-membered homodetic cyclic peptide composed from L-phenylglycyl, D-tryptophyl, L-lysyl, O-benzyl-L-tyrosyl, L-phenylalanyl and modified L-hydroxyproline residues joined in sequence. A somatostatin analogue with pharmacologic properties mimicking those of the natural hormone somatostatin; used (as its diaspartate salt) for treatment of Cushing's disease.	3.48	1	1	homodetic cyclic peptide; peptide hormone	antineoplastic agent
zeolites [no description available]	2	1	0
cgp 55845a CGP 55845A: GABA-B receptor antagonist; RN refers to cpd with no isomeric designation; CGP 55845 is the (1S,2S)-isomer	2.31	1	0
2-(4-bromo-2,5-dimethoxyphenyl)-n-((2-methoxyphenyl)methyl)ethanamine Cimbi-36: a PET radioligand; structure in first source	2.15	1	0
phosphoramidite phosphoramidite: structure in first source. phosphoramidite : A compound with the general formula (RO)2PNR2. Phosphoramidites can be regarded as phosphites that have an NR2 instead of an OH group, or as amides of phosphorous acid.	2.07	1	0
n-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide: inhibits rat renal microsomal arachidonic acid epoxidation	2.05	1	0
linagliptin Linagliptin: A purine and quinazoline derivative that functions as an INCRETIN and DIPEPTIDYL-PEPTIDASE IV INHIBTOR. It is used as a HYPOGLYCEMIC AGENT in the treatment of TYPE II DIABETES MELLITUS.. linagliptin : A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type II diabetes.	9.95	37	0	aminopiperidine; quinazolines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
fmrfamide FMRFamide: A molluscan neuroactive peptide which induces a fast excitatory depolarizing response due to direct activation of amiloride-sensitive SODIUM CHANNELS. (From Nature 1995; 378(6558): 730-3)	2.05	1	0
am 1241 AM 1241: a CB(2) receptor-selective agonist; no further information available 11/2001	2.08	1	0
nps r-467 NPS R-467: calcimimetic compound; structure given in first source	2.05	1	0
artenimol artenimol: derivative of antimalarial drug artemisinin (quinghaosu)	2.77	3	0
4-phenoxyphenoxyethyl thiocyanate 4-phenoxyphenoxyethyl thiocyanate: has antiparasitic activity; structure in first source	2.07	1	0
az10606120 AZ10606120: a P2X7 receptor antagonist	4.17	14	0
jwh 018 1-pentyl-3-(1-naphthoyl)indole: structure in first source	4.33	5	0	indolecarboxamide
6-chlorotacrine 6-chlorotacrine: structure given in first source	2.21	1	0
le 135 LE 135: structure given in first source	2.21	1	0	dibenzodiazepine
r 214127 R 214127: an mGlu1 receptor ligand; structure in first source	2.01	1	0
jwh-073 [no description available]	2.15	1	0	indolecarboxamide
arterolane arterolane: a trioxolane with antimalarial activity; structure in first source. arterolane : An oxaspiro compound that is dispiro[cyclohexane-1,3'-[1,2,4]trioxolane-5',2''-tricyclo[3.3.1.1(3,7)]decane] substituted by a 2-[(2-amino-2-methylpropyl)amino]-2-oxoethyl group at position 4s. Its maleic acid salt is used as an antimalarial drug in combination with piperaquine.	3.6	8	0
oxadiazoles Oxadiazoles: Compounds containing five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom which exist in various regioisomeric forms.	3.14	5	0
ribose ribopyranose : The pyranose form of ribose.	3.06	1	0	D-ribose; ribopyranose
5-formylcytosine 5-formylcytosine: structure in first source. 5-formylcytosine : A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a formyl group.	2.54	2	0	aminopyrimidine; heteroarenecarbaldehyde; nucleobase analogue; pyrimidone	metabolite
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.	2.05	1	0	alpha-D-glucosyl-(1->4)-D-mannopyranose
erastin erastin: an antineoplastic agent; structure in first source. erastin : A member of the class of quinazolines that is quinazolin-4(3H)-one in which the hydrogens at positions 2 and 3 are replaced by 1-{4-[(4-chlorophenoxy)acetyl]piperazin-1-yl}ethyl and 2-ethoxyphenyl groups, respectively. It is an inhibitor of voltage-dependent anion-selective channels (VDAC2 and VDAC3) and a potent ferroptosis inducer.	2.15	1	0	aromatic ether; diether; monochlorobenzenes; N-acylpiperazine; N-alkylpiperazine; quinazolines; tertiary carboxamide	antineoplastic agent; ferroptosis inducer; voltage-dependent anion channel inhibitor
wrenchnolol wrenchnolol: structure in first source	4.9	6	0
uamc00039 UAMC00039: dipeptidyl peptidase II inhibitor; structure in first source	2.03	1	0
elagolix [no description available]	2.13	1	0	organonitrogen compound; organooxygen compound
aspalathin aspalathin: structure in first source. aspalathin : A member of the class of dihydrochalcones that is the 2-C-beta-D-glucopyranide of phloroglucinol and which is substituted at position 4 by a 3-(3,4-dihydroxyphenyl)propanoyl group. A metabolite of red bush, Aspalathus linearis (and present in the herbal tea made from the leaves), aspalathin exhibits significant hypoglycemic activity.	2.07	1	0	C-glycosyl compound; catechols; dihydrochalcones; polyketide; polyphenol	antioxidant; EC 1.17.3.2 (xanthine oxidase) inhibitor; hypoglycemic agent; plant metabolite
ponesimod ponesimod: structure in first source	3.23	1	0
adamanolol adamanolol: structure in first source	5.07	5	0
alogliptin alogliptin: structure in first source. alogliptin : A piperidine that is 3-methyl-2,4-dioxo-3,4-dihydropyrimidine carrying additional 2-cyanobenzyl and 3-aminopiperidin-1-yl groups at positions 1 and 2 respectively (the R-enantiomer). Used in the form of its benzoate salt for treatment of type 2 diabetes.	12.6	48	2	nitrile; piperidines; primary amino compound; pyrimidines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent
garsubellin a garsubellin A: from wood of Garcinia subelliptica; structure given in first source	2.01	1	0
artemisone artemisone: second-generation semi-synthetic artemisinin derivative for antimalarial therapy devoid of neurotoxicity	2.07	1	0
apremilast [no description available]	4.15	2	0	aromatic ether; N-acetylarylamine; phthalimides; sulfone	non-steroidal anti-inflammatory drug; phosphodiesterase IV inhibitor
sitagliptin phosphate Sitagliptin Phosphate: A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.	19.74	188	17
alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc Sialyl Lewis X Antigen: A sialylated version of Lewis X antigen expressed on cell surfaces. It is a ligand for SELECTINS.. alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-D-GlcpNAc : A branched amino tetrasaccharide consisting of a sialyl residue, linked (2->3) to a galactosyl residue that in turn is linked (1->4) to a glucosaminyl residue, which is also carrying a fucosyl residue at the 3-position.	2.04	1	0	amino tetrasaccharide; glucosamine oligosaccharide	epitope
td-5108 TD-5108: a selective 5-HT(4) receptor agonist with high intrinsic activity; structure in first source	2.02	1	0
empagliflozin [no description available]	6.67	7	0	aromatic ether; C-glycosyl compound; monochlorobenzenes; tetrahydrofuryl ether	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
lc15-0444 LC15-0444: Dipeptidyl Peptidase IV Inhibitors; orally active small molecule for the treatment of type II diabetes	3.19	1	0	organonitrogen compound; organooxygen compound
peramivir peramivir hydrate : A hydrate that is the trihydrate form of peramivir. Used for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.. peramivir : A member of the class of guanidines that is used (as its trihydrate) for the treatment of acute uncomplicated influenza in patients 18 years and older who have been symptomatic for no more than two days.	2.48	2	0
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.	1.96	1	0	benzoxazole
scopolamine hydrobromide [no description available]	3.29	6	0
pituitrin Pituitrin: A substance or extract from the neurohypophysis (PITUITARY GLAND, POSTERIOR).	1.99	1	0
resorcinarene resorcinarene: structure in first source	2.74	3	0
rifamycins [no description available]	4.5	2	0
diborane diborane: reduces heterocyclic cpds. diborane : Boranes containing only two B atoms, linked either directly by a B-B bond or via hydrogen bridging atoms.	2.02	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.	2.69	3	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.	1.98	1	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.	1.99	1	0
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.	3.8	2	1
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2.9	4	0	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
isomigrastatin isomigrastatin: isolated from Streptomyces platensis; structure in first source	3.31	1	0	macrolide
trelagliptin trelagliptin: a dipeptidyl peptidase IV inhibitor	3.35	1	0	benzenes; nitrile
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.	3.16	5	0
arsenicin a arsenicin A: structure in first source	2.88	3	0
cholecystokinin Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.	2.93	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.	4.42	4	1	polypeptide
gala peptide GALA peptide: synthetic 30 amino acid peptide; its association with membrane vesicles has been studied; amino acid sequence given in first source	2.25	1	0
nociceptin [no description available]	2.7	3	0	organic molecular entity; polypeptide	human metabolite; rat metabolite
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.	2.42	2	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.	2.73	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.	14.62	41	24	peptide hormone
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.	3.46	7	0
iberiotoxin [no description available]	2.03	1	0
cucurbit(8)uril cucurbit(8)uril: a macrocyclic polymer compound comprising 8 GLYCOLURIL units with methylene bridges	2.07	1	0
oligonucleotides [no description available]	3.55	8	0
liraglutide [no description available]	13.83	52	2	lipopeptide; polypeptide	glucagon-like peptide-1 receptor agonist; neuroprotective agent
glucagon-like peptide 1 Glucagon-Like Peptide 1: A peptide of 36 or 37 amino acids that is derived from PROGLUCAGON and mainly produced by the INTESTINAL L CELLS. GLP-1(1-37 or 1-36) is further N-terminally truncated resulting in GLP-1(7-37) or GLP-1-(7-36) which can be amidated. These GLP-1 peptides are known to enhance glucose-dependent INSULIN release, suppress GLUCAGON release and gastric emptying, lower BLOOD GLUCOSE, and reduce food intake.	19.17	156	29
incretins Incretins: Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially.	15.53	75	10
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.	13.48	21	13
gastrin 17 gastrin-17 : One of the primary forms of gastrin that is a 17-membered peptide consisting of Glp, Gly, Pro, Trp, Leu, Glu, Glu, Glu, Glu, Glu, Ala, Tyr, Gly, Trp, Met, Asp and Phe-NH2 residues joined in sequence.	2.03	1	0	gastrin	antineoplastic agent
exendin (9-39) exendin (9-39): a peptide from the venom of the lizard Heloderma suspectum; inhibits glucagon-like peptide-1 (GLP-1) induced cAMP production; its structure is related to exendin-4	5.87	2	2
cellulose DEAE-Cellulose: Cellulose derivative used in chromatography, as ion-exchange material, and for various industrial applications.	8.27	5	0	glycoside
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	3.68	10	0	1,2-diacyl-sn-glycero-3-phosphocholine
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.	2.03	1	0	chlorophyll; methyl ester	cofactor
platencin platencin: inhibits both FabF and FabH; structure in first source. platencin : A monocarboxylic acid amide obtained by the formal condensation of the amino group of 3-amino-2,4-dihydroxybenzoic acid with the carboxy group of the polycyclic cage component. It is an antibiotic isolated from Streptomyces platensis and exhibits inhibitory activity against fatty acid synthase.	7.78	34	0	aromatic amide; cyclic ketone; dihydroxybenzoic acid; monocarboxylic acid amide; polycyclic cage	antibacterial agent; antimicrobial agent; bacterial metabolite; EC 2.3.1.85 (fatty acid synthase) inhibitor
dihydroceramide dihydroceramide: lacks the 4-5 trans double bond of the sphingosine moiety of ceramides; structure in first source. N-acylsphinganine : A ceramide consisting of sphinganine in which one of the amino hydrogens is substituted by a fatty acyl group.. dihydroceramide : An N-acylsphingoid obtained by formal condensation of the carboxy group of any fatty acid with the amino group of any dihydrosphingoid base.	2.11	1	0
adenosine kinase Adenosine Kinase: An enzyme that catalyzes the formation of ADP plus AMP from adenosine plus ATP. It can serve as a salvage mechanism for returning adenosine to nucleic acids. EC 2.7.1.20.	2.39	2	0
sphingosine kinase [no description available]	6.9	28	0
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.	2.08	1	0
1,2,4-trioxane 1,2,4-trioxane: structure in first source	3.19	5	0
chitosan [no description available]	3.22	5	0
dioxetanone dioxetanone: structure in first source	2.21	1	0
15-deoxyprostaglandin j2 15-deoxyprostaglandin J2: 15d-PGJ2 abbreviation is also used for 15-deoxy-delta(12,14)PGJ2	2.13	1	0
sodium nitrite Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.	2.39	2	0	inorganic sodium salt; nitrite salt	antidote to cyanide poisoning; antihypertensive agent; antimicrobial food preservative; food antioxidant; poison
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	1.96	1	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.	2.31	1	0
canagliflozin canagliflozin hydrate : A hydrate that is the hemihydrate form of canagliflozin. Used for treatment of type II diabetes via inhibition of sodium-glucose transport protein subtype 2.	5.72	3	0	C-glycosyl compound; organofluorine compound; thiophenes	hypoglycemic agent; sodium-glucose transport protein subtype 2 inhibitor
insulin, isophane Insulin, Isophane: An intermediate-acting INSULIN preparation with onset time of 2 hours and duration of 24 hours. It is produced by crystallizing ZINC-insulin-PROTAMINES at neutral pH 7. Thus it is called neutral protamine Hagedorn for inventor Hans Christian Hagedorn.	4.8	2	1
oz 439 artefenomel: an antimalarial ozonide; structure in first source	11.84	32	8
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)	1.99	1	0
n-(adamantan-1-yl)-4-oxo-1-pentyl-6-phenyl-1,4-dihydroquinoline-3-carboxamide N-(adamantan-1-yl)-4-oxo-1-pentyl-6-phenyl-1,4-dihydroquinoline-3-carboxamide: structure in first source	3.01	4	0
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.83	3	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	1	0	fumarate salt
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.4	2	0
neurotensin neurotensin, Tyr(11)-: RN given refers to parent cpd & (D)-isomer; RN for cpd without isomeric designation not avail 5/91	4.53	24	0	peptide hormone	human metabolite; mitogen; neurotransmitter; vulnerary
bradykinin, 1-adamantanecarboxylic acid-arg(0)-hyp(3)-thi(5,8)-phe(7)- bradykinin, 1-adamantanecarboxylic acid-Arg(0)-Hyp(3)-Thi(5,8)-Phe(7)-: bradykinin B2 receptor antagonist; structure given in first source	4.99	9	1
incb-018424 [no description available]	4.2	2	0	nitrile; pyrazoles; pyrrolopyrimidine	antineoplastic agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
11,12-epoxy-5,8,14-eicosatrienoic acid 11,12-epoxy-5,8,14-eicosatrienoic acid: RN given refers to cpd without isomeric designation. (11S,12R)-EET : An 11,12-EET in which the epoxy moiety has 11S,12R-configuration.. 11,12-EET : An EET obtained by formal epoxidation of the 11,12-double bond of arachidonic acid.	2.98	4	0	11,12-EET	human xenobiotic metabolite
plx4032 [no description available]	2.31	1	0	aromatic ketone; difluorobenzene; monochlorobenzenes; pyrrolopyridine; sulfonamide	antineoplastic agent; B-Raf inhibitor
glycolipids [no description available]	2.93	4	0
baricitinib [no description available]	6.85	11	0	azetidines; nitrile; pyrazoles; pyrrolopyrimidine; sulfonamide	anti-inflammatory agent; antirheumatic drug; antiviral agent; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; immunosuppressive agent
piperidines Piperidines: A family of hexahydropyridines.	19.48	107	3
jwh-122 (4-methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone: structure in first source	2.55	2	0
nitd 609 NITD 609: an antimalarial and coccidiostat; structure in first source	2.57	2	0
anagliptin anagliptin: anagliptin hydrochloride salt is the active compound	3.19	1	0	amino acid amide
plukenetione a plukenetione A: produced by honey bees from various plant sources; structure in first source	2.04	1	0
ur-144 (1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone: structure in first source	2.53	2	0
jwh-210 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone: a cannabimimetic; structure in first source	2.15	1	0	indolecarboxamide
exenatide Exenatide: A synthetic form of exendin-4, a 39-amino acid peptide isolated from the venom of the Gila monster lizard (Heloderma suspectum). Exenatide increases CYCLIC AMP levels in pancreatic acinar cells and acts as a GLUCAGON-LIKE PEPTIDE-1 RECEPTOR (GLP-1) agonist and incretin mimetic, enhancing insulin secretion in response to increased glucose levels; it also suppresses inappropriate glucagon secretion and slows gastric emptying. It is used an anti-diabetic and anti-obesity agent.	14.43	61	2
glpg0634 [no description available]	5.92	6	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	7.94	8	6	polypeptide
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.	2.69	3	0
incb039110 INCB039110: a JAK1 inhibitor; structure in first source	3.23	1	0
AM2201 1-(5-fluoropentyl)-3-(1-naphthoyl)indole: a cannabimimetic; structure in first source	2.53	2	0	indolecarboxamide
tuftsin Tuftsin: N(2)-((1-(N(2)-L-Threonyl)-L-lysyl)-L-prolyl)-L-arginine. A tetrapeptide produced in the spleen by enzymatic cleavage of a leukophilic gamma-globulin. It stimulates the phagocytic activity of blood polymorphonuclear leukocytes and neutrophils in particular. The peptide is located in the Fd fragment of the gamma-globulin molecule.	2.02	1	0	peptide
norbornene anhydride [no description available]	2.02	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.	3.09	5	0	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
coumermycin coumermycin: RN given refers to coumermycin A1; structure. coumermycin A1 : A hydroxycoumarin antibiotic that is obtained from Streptomyces rishiriensis and exhibits potent antibacterial and anticancer activity.	2.06	1	0	aromatic amide; coumarins; glycoside; heteroarenecarboxylate ester; pyrroles	antimicrobial agent; antineoplastic agent; bacterial metabolite; DNA synthesis inhibitor; Hsp90 inhibitor; topoisomerase IV inhibitor
novobiocin Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.	2.06	1	0	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent
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.	3.23	1	0
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.	2.11	1	0	monohydroxybenzoate	plant metabolite
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.	3.85	2	1	benzenes; hydroxycoumarin; methyl ketone
tipranavir tipranavir: inhibits HIV-1 protease. tipranavir : A pyridine-2-sulfonamide substituted at C-5 by a trifluoromethyl group and at the sulfonamide nitrogen by a dihydropyrone-containing m-tolyl substituent. It is an HIV-1 protease inhibitor.	3.44	1	1	sulfonamide	antiviral drug; HIV protease inhibitor
tigecycline [no description available]	3.23	1	0
nickel nitrilotriacetic acid [no description available]	2.17	1	0
spliceosomal peptide p140 spliceosomal peptide P140: synthetic peptide, sequence 131-151 of the U1-70K protein phosphorylated at Ser140, which is recognized by lupus CD4+ T cells for the treatment of patients with systemic lupus erythematosus	2.1	1	0
charybdotoxin [no description available]	2.42	2	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.	2.77	3	0
5-adamantan-1-yl-n-(2,4-dihydroxybenzyl)-2,4-dimethoxybenzamide 5-adamantan-1-yl-N-(2,4-dihydroxybenzyl)-2,4-dimethoxybenzamide: a tyrosinase inhibitor; structure in first source	4.89	7	1
pbtz169 macozinone: an antitubercular agent; structure in first source	3.23	1	0
sr9009 [no description available]	2.41	1	0
sts-135 N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide: a synthetic cannabinoid; structure in first source	3.39	6	0	indolecarboxamide
AKB48 N-(1-adamantyl)-1-pentylindazole-3-carboxamide: a synthetic cannabinoid; structure in first source	5.22	13	0	aromatic amide; indazoles
xlr-11 XLR-11: synthetic cannabinoid; structure in first source	2.83	3	0
bananin bananin: structure in first source	7.72	3	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.	3.12	5	0
am4113 AM4113: a cannabinoid CB1 receptor neutral antagonist	2.04	1	0
cpzen-45 CPZEN-45: caprazamycin derivative; structure in first source	3.23	1	0
kiss1 protein, human Kisspeptins: Intercellular signaling peptides that were originally characterized by their ability to suppress NEOPLASM METASTASIS. Kisspeptins have since been found to play an important role in the neuroendocrine regulation of REPRODUCTION.	3.2	5	0
sdb-001 N-(adamtan-1-yl)-1-pentyl-1H-indole-3-carboxamide: a cannabimimetic; structure in first source	2.8	3	0
3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide 3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide: an antineoplastic agent that inhibits sphingosine kinase-2; structure in first source	11.93	49	4
1-pentyl-1h-indole-3-carboxylic acid 8-quinolinyl ester 1-pentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester: a recreational synthetic cannabinoid; structure in first source	2.53	2	0
n-(1-adamantyl)-1-(5-fluoropentyl)-1h-indazole-3-carboxamide N-(1-adamantyl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide: a cannabinoid receptor agonist; structure in first source	3.94	11	0	aromatic amide; indazoles
glutaminase [no description available]	3.14	1	0
deitiforin deitiforin: Russian drug	2.38	2	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.	2.13	1	0	phthalocyanines; tetrapyrrole fundamental parent
n-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1h-indazole-3-carboxamide N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide: a synthetic cannabinoid known as black mamba	2.15	1	0
benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone benzyloxycarbonylvalyl-alanyl-aspartyl fluoromethyl ketone: an interleukin-1beta converting enzyme (ICE)-like protease inhibitor	2.07	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.67	3	0
sj733 SJ733: antimalarial; structure in first source	2.25	1	0
peptide yy peptide YY (3-36): amino acid sequence given in first source	3.48	1	1
adrenomedullin Adrenomedullin: A 52-amino acid peptide with multi-functions. It was originally isolated from PHEOCHROMOCYTOMA and ADRENAL MEDULLA but is widely distributed throughout the body including lung and kidney tissues. Besides controlling fluid-electrolyte homeostasis, adrenomedullin is a potent vasodilator and can inhibit pituitary ACTH secretion.	2.69	3	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)	2.25	1	0
aconitine Aconitine: A C19 norditerpenoid alkaloid (DITERPENES) from the root of ACONITUM; DELPHINIUM and larkspurs. It activates VOLTAGE-GATED SODIUM CHANNELS. It has been used to induce ARRHYTHMIAS in experimental animals and it has anti-inflammatory and anti-neuralgic properties.. aconitine : A diterpenoid that is 20-ethyl-3alpha,13,15alpha-trihydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitane-8,14alpha-diol having acetate and benzoate groups at the 8- and 14-positions respectively.	2.08	1	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.	12.03	16	1
ecallantide ecallantide: an NSAID and analgesic	2.05	1	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.	3.46	1	1
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.	4.07	2	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).	3.01	4	0
peptide yy Peptide YY: A 36-amino acid peptide produced by the L cells of the distal small intestine and colon. Peptide YY inhibits gastric and pancreatic secretion.. peptide YY : A 36-membered human gut polypeptide consisting of Tyr, Pro, Ile, Lys, Pro, Glu, Ala, Pro, Gly, Glu, Asp, Ala, Ser, Pro, Glu, Glu, Leu, Asn, Arg, Tyr, Tyr, Ala, Ser, Leu, Arg, His, Tyr, Leu, Asn, Leu, Val, Thr, Arg, Gln, Arg and Tyr-NH2 residues joined in sequence.	4.17	3	1
n-adamantyl-4-methylthiazol-2-amine N-adamantyl-4-methylthiazol-2-amine: structure in first source	3.38	6	0
carboxymethyl-beta-cyclodextrin [no description available]	2.13	1	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.	2.44	2	0
cord factors Cord Factors: Toxic glycolipids composed of trehalose dimycolate derivatives. They are produced by MYCOBACTERIUM TUBERCULOSIS and other species of MYCOBACTERIUM. They induce cellular dysfunction in animals.	2.77	3	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	2.17	1	0
trehalose monomycolate trehalose monomycolate : Any trehalose bearing a single O-mycolate substituent; obtained via extraction of the cell wall of Mycobacterium bovis.	2.77	3	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.	2.08	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
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.	2.44	2	0	3',5'-cyclic purine nucleotide; guanyl ribonucleotide	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	3.39	2	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2'-deoxyguanosine 5'-phosphate 2'-deoxyguanosine 5'-phosphate: RN given refers to parent cpd.. 2'-deoxyguanosine 5'-monophosphate : A purine 2'-deoxyribonucleoside 5'-monophosphate having guanine as the nucleobase.	2.37	2	0	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
guanosine diphosphate Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.	2.71	3	0	guanosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	2.41	2	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	1	0	guanosines; purines D-ribonucleoside	fundamental metabolite
hypoxanthine [no description available]	1.98	1	0	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
inosinic acid Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.	2.37	2	0	inosine phosphate; purine ribonucleoside 5'-monophosphate	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.	8.23	5	0	folic acids; N-acyl-amino acid	human metabolite; mouse metabolite; nutrient
3-methyladenine N3-methyladenine: structure in first source	3.85	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.	2.73	3	0	nucleoside triphosphate analogue
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)	10.73	16	6	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.	1.99	1	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
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.	2.11	1	0	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake inhibitor
zaprinast zaprinast: anaphylaxis inhibitor; structure	2.41	2	0	triazolopyrimidines
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.	2.03	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
thiolactomycin thiolactomycin: from actinomycetes; structure given in first source	2.04	1	0
guanosine 5'-o-(2-thiodiphosphate) [no description available]	2.71	3	0	nucleoside diphosphate analogue
trypan blue Trypan Blue: A diazo-naphthalene sulfonate that is widely used as a stain.. trypan blue : An organosulfonate salt that is the tetrasodium salt of 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonic acid).	2.03	1	0
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	3.39	2	0	guanosines	biomarker
asoxime chloride [no description available]	2.01	1	0
8-oxyguanine 8-oxyguanine: structure given in first source. 8-oxoguanine : An oxopurine that is guanine which is substituted by an oxo group at position 8.	1.98	1	0	2-aminopurines; oxopurine
cyanine dye 3 cyanine dye 3: structures of Cy3 derivatives given in first source	2.11	1	0
eye [no description available]	2.21	1	0
ferroquine ferroquine: an antimalarial agent; structure in first source	5.47	4	1
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.	2.05	1	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.	1.98	1	0
yo-pro 1 YO-PRO 1: a generally membrane impermeable fluorescent dye	2.48	2	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	3.36	7	0
galanin-like peptide Galanin-Like Peptide: A neuropeptide that is highly homologous to GALANIN. It is produced by proteolytic processing of a larger protein that is unrelated to prepro-galanin and preferentially binds to GALANIN-2 RECEPTOR.	2.07	1	0
preproenkephalin preproenkephalin: initial enkephalin precursor	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.	2.17	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	3.44	1	1
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.	2.08	1	0

Condition	Relationship Strength	Studies	Trials
Diabetes Mellitus, Adult-Onset [description not available]	28.44	1,063	356
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.	28.44	1,063	356
Central European Encephalitis [description not available]	2.31	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	9.52	112	0
Infection, Wound [description not available]	2.31	1	0
Infections, Staphylococcal Skin [description not available]	2.66	2	0
Staphylococcal Skin Infections Infections to the skin caused by bacteria of the genus STAPHYLOCOCCUS.	2.66	2	0
Benign Neoplasms [description not available]	12.3	34	7
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.	12.3	34	7
Cancer of Colon [description not available]	3.74	10	0
Colonic Neoplasms Tumors or cancer of the COLON.	3.74	10	0
Innate Inflammatory Response [description not available]	10.54	36	8
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	8.31	16	1
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.	10.54	36	8
Colitis Gravis [description not available]	9.35	6	4
Colitis, Granulomatous [description not available]	5.11	3	1
Bowel Diseases, Inflammatory [description not available]	4.11	2	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.	9.09	5	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.	9.35	6	4
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.	5.11	3	1
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.	4.11	2	0
Aura [description not available]	2.85	3	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)	2.85	3	0
Rheumatoid Arthritis [description not available]	15.34	43	14
Shingles [description not available]	9.63	7	4
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.	15.34	43	14
Herpes Zoster An acute infectious, usually self-limited, disease believed to represent activation of latent varicella-zoster virus (HERPESVIRUS 3, HUMAN) in those who have been rendered partially immune after a previous attack of CHICKENPOX. It involves the SENSORY GANGLIA and their areas of innervation and is characterized by severe neuralgic pain along the distribution of the affected nerve and crops of clustered vesicles over the area. (From Dorland, 27th ed)	9.63	7	4
Bone Loss, Osteoclastic [description not available]	4.45	4	1
Age-Related Osteoporosis [description not available]	2.41	1	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.	2.41	1	0
Autoimmune Disease [description not available]	2.41	1	0
Pemphigoid [description not available]	4.77	10	0
Drug-Induced Stevens Johnson Syndrome [description not available]	2.41	1	0
Autoimmune Diseases Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.	2.41	1	0
Pemphigoid, Bullous A chronic and relatively benign subepidermal blistering disease usually of the elderly and without histopathologic acantholysis.	4.77	10	0
Stevens-Johnson Syndrome Rare cutaneous eruption characterized by extensive KERATINOCYTE apoptosis resulting in skin detachment with mucosal involvement. It is often provoked by the use of drugs (e.g., antibiotics and anticonvulsants) or associated with PNEUMONIA, MYCOPLASMA. It is considered a continuum of Toxic Epidermal Necrolysis.	2.41	1	0
Nervous System Disorders [description not available]	3.98	4	0
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	3.98	4	0
Chronic Kidney Diseases [description not available]	7.24	7	1
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)	7.24	7	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	17.96	91	25
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	22.82	94	42
Alloxan Diabetes [description not available]	6.35	55	0
Cognitive Decline [description not available]	3.65	7	0
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	9.14	18	2
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	3.65	7	0
Adenocarcinoma, Basal Cell [description not available]	2.83	3	0
Cancer of Pancreas [description not available]	8.9	24	2
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.83	3	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).	8.9	24	2
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).	16.99	45	8
Palmoplantaris Pustulosis [description not available]	7.97	7	1
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.	7.97	7	1
Cancer of Nasopharynx [description not available]	2.41	1	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.41	1	0
Atherogenesis [description not available]	6.65	10	2
Atheroma [description not available]	3.05	4	0
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	6.65	10	2
Phlegmon [description not available]	2.41	1	0
Infectious Skin Diseases [description not available]	2.41	1	0
Cellulitis An acute, diffuse, and suppurative inflammation of loose connective tissue, particularly the deep subcutaneous tissues, and sometimes muscle, which is most commonly seen as a result of infection of a wound, ulcer, or other skin lesions.	2.41	1	0
Skin Diseases, Infectious Skin diseases caused by bacteria, fungi, parasites, or viruses.	2.41	1	0
Acute Confusional Senile Dementia [description not available]	8.57	22	1
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)	8.57	22	1
Koch's Disease [description not available]	6.42	14	0
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	6.42	14	0
Degenerative Diseases, Central Nervous System [description not available]	4.01	4	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.	9.01	4	0
Benign Neoplasms, Brain [description not available]	3.05	4	0
Astrocytoma, Grade IV [description not available]	3.21	5	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.	3.05	4	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.	3.21	5	0
2019 Novel Coronavirus Disease [description not available]	4.47	6	0
ALS - Amyotrophic Lateral Sclerosis [description not available]	2.89	3	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)	2.89	3	0
Injury, Ischemia-Reperfusion [description not available]	4.23	16	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.	4.23	16	0
Cardiac Failure [description not available]	15.89	55	18
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.	15.89	55	18
Diabetic Cardiomyopathies Diabetes complications in which VENTRICULAR REMODELING in the absence of CORONARY ATHEROSCLEROSIS and hypertension results in cardiac dysfunctions, typically LEFT VENTRICULAR DYSFUNCTION. The changes also result in myocardial hypertrophy, myocardial necrosis and fibrosis, and collagen deposition due to impaired glucose tolerance.	7.48	9	1
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)	2.21	1	0
Intraocular Pressure The pressure of the fluids in the eye.	2.44	2	0
American Trypanosomiasis [description not available]	2.87	3	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.	2.87	3	0
Diabetic Glomerulosclerosis [description not available]	14.62	55	10
Diabetic Nephropathies KIDNEY injuries associated with diabetes mellitus and affecting KIDNEY GLOMERULUS; ARTERIOLES; KIDNEY TUBULES; and the interstitium. Clinical signs include persistent PROTEINURIA, from microalbuminuria progressing to ALBUMINURIA of greater than 300 mg/24 h, leading to reduced GLOMERULAR FILTRATION RATE and END-STAGE RENAL DISEASE.	14.62	55	10
Glial Cell Tumors [description not available]	3.03	4	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)	8.03	4	0
Anoxemia [description not available]	4.31	6	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	4.31	6	0
Absence Status [description not available]	2.59	2	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)	2.59	2	0
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	7.27	13	1
Asthma, Bronchial [description not available]	2.74	3	0
Acute Disease Disease having a short and relatively severe course.	5.19	10	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).	2.74	3	0
Parasitemia The presence of parasites (especially malarial parasites) in the blood. (Dorland, 27th ed)	5.34	4	1
Plasmodium falciparum Malaria [description not available]	10.13	15	8
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.	10.13	15	8
Lung Injury, Acute [description not available]	3.11	4	0
Acute Lung Injury A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).	3.11	4	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.	8.22	8	3
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.	8.22	8	3
Sclerosis, Systemic [description not available]	2.25	1	0
Scleroderma, Systemic A chronic multi-system disorder of CONNECTIVE TISSUE. It is characterized by SCLEROSIS in the SKIN, the LUNGS, the HEART, the GASTROINTESTINAL TRACT, the KIDNEYS, and the MUSCULOSKELETAL SYSTEM. Other important features include diseased small BLOOD VESSELS and AUTOANTIBODIES. The disorder is named for its most prominent feature (hard skin), and classified into subsets by the extent of skin thickening: LIMITED SCLERODERMA and DIFFUSE SCLERODERMA.	2.25	1	0
Local Neoplasm Recurrence [description not available]	2.25	1	0
Liver Dysfunction [description not available]	5.25	4	1
Liver Diseases Pathological processes of the LIVER.	5.25	4	1
Angiogenesis, Pathologic [description not available]	3.37	6	0
Pulmonary Arterial Remodeling [description not available]	3.82	3	0
Airway Remodeling The structural changes in the number, mass, size and/or composition of the airway tissues.	2.25	1	0
Acute Edematous Pancreatitis [description not available]	12.22	19	10
Pancreatitis INFLAMMATION of the PANCREAS. Pancreatitis is classified as acute unless there are computed tomographic or endoscopic retrograde cholangiopancreatographic findings of CHRONIC PANCREATITIS (International Symposium on Acute Pancreatitis, Atlanta, 1992). The two most common forms of acute pancreatitis are ALCOHOLIC PANCREATITIS and gallstone pancreatitis.	12.22	19	10
Grippe [description not available]	15.65	107	15
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.	15.65	107	15
Black Fever [description not available]	2.25	1	0
Leishmaniasis, American [description not available]	2.25	1	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.	2.25	1	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.	2.25	1	0
Burns Injuries to tissues caused by contact with heat, steam, chemicals (BURNS, CHEMICAL), electricity (BURNS, ELECTRIC), or the like.	2.76	3	0
Diabetes Mellitus Type 1.5 [description not available]	4.53	2	2
Deficiency, Vitamin D [description not available]	3.64	1	1
Latent Autoimmune Diabetes in Adults Autoimmune diabetes in adults with slowly progressive PANCREATIC BETA CELL failure and the presence of circulating autoantibodies to PANCREATIC ISLETS cell antigens.	4.53	2	2
Vitamin D Deficiency A nutritional condition produced by a deficiency of VITAMIN D in the diet, insufficient production of vitamin D in the skin, inadequate absorption of vitamin D from the diet, or abnormal conversion of vitamin D to its bioactive metabolites. It is manifested clinically as RICKETS in children and OSTEOMALACIA in adults. (From Cecil Textbook of Medicine, 19th ed, p1406)	3.64	1	1
Fasting Hypoglycemia HYPOGLYCEMIA expressed in the postabsorptive state, after prolonged FASTING, or an overnight fast.	24.28	313	83
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.	24.28	313	83
Aggressive Natural Killer Cell Leukemia [description not available]	2.25	1	0
Leukemia, Large Granular Lymphocytic A spectrum of disorders characterized by clonal expansions of the peripheral blood LYMPHOCYTE populations known as large granular lymphocytes which contain abundant cytoplasm and azurophilic granules. Subtypes develop from either CD3-negative NATURAL KILLER CELLS or CD3-positive T-CELLS. The clinical course of both subtypes can vary from spontaneous regression to progressive, malignant disease.	2.25	1	0
Airflow Obstruction, Chronic [description not available]	2.25	1	0
Complications of Diabetes Mellitus [description not available]	9.02	12	2
Cancer of Lung [description not available]	5.24	18	0
Lung Neoplasms Tumors or cancer of the LUNG.	5.24	18	0
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	2.25	1	0
Schistosoma mansoni Infection [description not available]	2.25	1	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.	2.25	1	0
Nasopharyngitis Inflammation of the NASOPHARYNX, usually including its mucosa, related lymphoid structure, and glands.	4.55	1	1
Avian Flu [description not available]	3.14	5	0
Influenza in Birds Infection of domestic and wild fowl and other BIRDS with INFLUENZA A VIRUS. Avian influenza usually does not sicken birds, but can be highly pathogenic and fatal in domestic POULTRY.	3.14	5	0
Infections, Coronavirus [description not available]	2.66	2	0
Pneumonia, Viral Inflammation of the lung parenchyma that is caused by a viral infection.	4.04	5	0
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).	2.66	2	0
Insulin Sensitivity [description not available]	14.67	70	16
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.	14.67	70	16
Prediabetes [description not available]	8.57	8	3
Prediabetic State The time period before the development of symptomatic diabetes. For example, certain risk factors can be observed in subjects who subsequently develop INSULIN RESISTANCE as in type 2 diabetes (DIABETES MELLITUS, TYPE 2).	8.57	8	3
Infections, Orthomyxoviridae [description not available]	5.38	23	0
Orthomyxoviridae Infections Virus diseases caused by the ORTHOMYXOVIRIDAE.	5.38	23	0
Breast Cancer [description not available]	9.04	13	0
Cancer of Liver [description not available]	3.34	6	0
Breast Neoplasms Tumors or cancer of the human BREAST.	4.04	13	0
Liver Neoplasms Tumors or cancer of the LIVER.	3.34	6	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.	3.13	5	0
Acute Liver Injury, Drug-Induced [description not available]	3.22	5	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.	3.22	5	0
Asymptomatic Colonization [description not available]	2.25	1	0
MS (Multiple Sclerosis) [description not available]	2.87	3	0
Idiopathic Parkinson Disease [description not available]	6.96	15	2
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)	7.87	3	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)	6.96	15	2
Acute Respiratory Distress Syndrome [description not available]	2.25	1	0
Acute Hypercapnic Respiratory Failure [description not available]	2.43	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.	2.25	1	0
Respiratory Insufficiency Failure to adequately provide oxygen to cells of the body and to remove excess carbon dioxide from them. (Stedman, 25th ed)	2.43	2	0
Dry Eye [description not available]	2.25	1	0
Dry Eye Syndromes Corneal and conjunctival dryness due to deficient tear production, predominantly in menopausal and post-menopausal women. Filamentary keratitis or erosion of the conjunctival and corneal epithelium may be caused by these disorders. Sensation of the presence of a foreign body in the eye and burning of the eyes may occur.	2.25	1	0
Plasmodium vivax Malaria [description not available]	5.64	3	1
Malaria, Vivax Malaria caused by PLASMODIUM VIVAX. This form of malaria is less severe than MALARIA, FALCIPARUM, but there is a higher probability for relapses to occur. Febrile paroxysms often occur every other day.	5.64	3	1
Thromboembolism, Venous [description not available]	3.17	1	0
Neutropenia A decrease in the number of NEUTROPHILS found in the blood.	3.17	1	0
Venous Thromboembolism Obstruction of a vein or VEINS (embolism) by a blood clot (THROMBUS) in the blood stream.	3.17	1	0
Disease Exacerbation [description not available]	7.93	18	0
Infections, Plasmodium [description not available]	5.49	14	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.	10.49	14	0
Autoimmune Diabetes [description not available]	20.35	158	6
Complication, Postoperative [description not available]	17.29	144	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.	20.35	158	6
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.	17.29	144	0
Experimental Mammary Neoplasms [description not available]	2.48	2	0
Focal Segmental Glomerulosclerosis [description not available]	2.25	1	0
Nephritis Inflammation of any part of the KIDNEY.	2.25	1	0
Glomerulosclerosis, Focal Segmental A clinicopathological syndrome or diagnostic term for a type of glomerular injury that has multiple causes, primary or secondary. Clinical features include PROTEINURIA, reduced GLOMERULAR FILTRATION RATE, and EDEMA. Kidney biopsy initially indicates focal segmental glomerular consolidation (hyalinosis) or scarring which can progress to globally sclerotic glomeruli leading to eventual KIDNEY FAILURE.	2.25	1	0
Familial Nonmedullary Thyroid Cancer [description not available]	2.25	1	0
Invasiveness, Neoplasm [description not available]	3.05	4	0
Airway Hyper-Responsiveness [description not available]	2.25	1	0
ATLL [description not available]	3	4	0
Leukemia-Lymphoma, Adult T-Cell Aggressive T-Cell malignancy with adult onset, caused by HUMAN T-LYMPHOTROPIC VIRUS 1. It is endemic in Japan, the Caribbean basin, Southeastern United States, Hawaii, and parts of Central and South America and sub-Saharan Africa.	3	4	0
Blood Pressure, High [description not available]	9.75	43	0
Albuminuria The presence of albumin in the urine, an indicator of KIDNEY DISEASES.	6.94	9	1
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.	9.75	43	0
Bechterew Syndrome [description not available]	3.23	1	0
Ankylosing Spondylarthritis [description not available]	3.23	1	0
Psoriasis Arthropathica [description not available]	4.3	3	0
Spondylitis, Ankylosing A chronic inflammatory condition affecting the axial joints, such as the SACROILIAC JOINT and other intervertebral or costovertebral joints. It occurs predominantly in young males and is characterized by pain and stiffness of joints (ANKYLOSIS) with inflammation at tendon insertions.	3.23	1	0
Arthritis, Psoriatic A type of inflammatory arthritis associated with PSORIASIS, often involving the axial joints and the peripheral terminal interphalangeal joints. It is characterized by the presence of HLA-B27-associated SPONDYLARTHROPATHY, and the absence of rheumatoid factor.	4.3	3	0
Spondylarthropathies Heterogeneous group of arthritic diseases sharing clinical and radiologic features. They are associated with the HLA-B27 ANTIGEN and some with a triggering infection. Most involve the axial joints in the SPINE, particularly the SACROILIAC JOINT, but can also involve asymmetric peripheral joints. Subsets include ANKYLOSING SPONDYLITIS; REACTIVE ARTHRITIS; PSORIATIC ARTHRITIS; and others.	3.23	1	0
Tuberculosis, Drug-Resistant [description not available]	5.65	7	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.	5.65	7	0
Pulmonary Hypertension [description not available]	3.38	2	0
Hypertension, Pulmonary Increased VASCULAR RESISTANCE in the PULMONARY CIRCULATION, usually secondary to HEART DISEASES or LUNG DISEASES.	3.38	2	0
Cardiac Diseases [description not available]	4.58	5	1
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	4.58	5	1
Teratogenesis The formation of CONGENITAL ABNORMALITIES.	2.31	1	0
Acidosis, Diabetic [description not available]	2.31	1	0
Diabetic Ketoacidosis A life-threatening complication of diabetes mellitus, primarily of TYPE 1 DIABETES MELLITUS with severe INSULIN deficiency and extreme HYPERGLYCEMIA. It is characterized by KETOSIS; DEHYDRATION; and depressed consciousness leading to COMA.	2.31	1	0
Impaired Glucose Tolerance [description not available]	11.18	17	10
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.	11.18	17	10
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.03	14	0
Absence Seizure [description not available]	4.12	15	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.	4.12	15	0
Arteriosclerosis, Coronary [description not available]	9.91	9	6
Cardiac Arrest, Sudden [description not available]	3.68	2	0
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	9.91	9	6
Death, Sudden, Cardiac Unexpected rapid natural death due to cardiovascular collapse within one hour of initial symptoms. It is usually caused by the worsening of existing heart diseases. The sudden onset of symptoms, such as CHEST PAIN and CARDIAC ARRHYTHMIAS, particularly VENTRICULAR TACHYCARDIA, can lead to the loss of consciousness and cardiac arrest followed by biological death. (from Braunwald's Heart Disease: A Textbook of Cardiovascular Medicine, 7th ed., 2005)	3.68	2	0
Cirrhosis [description not available]	4.84	11	0
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	4.84	11	0
Hepatocellular Carcinoma [description not available]	2.53	2	0
Experimental Hepatoma [description not available]	2.31	1	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.	2.53	2	0
Porphyria [description not available]	2.31	1	0
Porphyrias A diverse group of metabolic diseases characterized by errors in the biosynthetic pathway of HEME in the LIVER, the BONE MARROW, or both. They are classified by the deficiency of specific enzymes, the tissue site of enzyme defect, or the clinical features that include neurological (acute) or cutaneous (skin lesions). Porphyrias can be hereditary or acquired as a result of toxicity to the hepatic or erythropoietic marrow tissues.	2.31	1	0
Gastric Diseases [description not available]	2.31	1	0
Granulocytic Leukemia [description not available]	2.97	4	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.	2.97	4	0
Arrhythmia [description not available]	2.83	3	0
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.	2.83	3	0
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.	5.78	7	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.	5.78	7	1
Encephalopathy, Traumatic [description not available]	2.15	1	0
Brain Swelling [description not available]	2.15	1	0
Brain Injuries, Traumatic A form of acquired brain injury which occurs when a sudden trauma causes damage to the brain.	2.15	1	0
Brain Edema Increased intracellular or extracellular fluid in brain tissue. Cytotoxic brain edema (swelling due to increased intracellular fluid) is indicative of a disturbance in cell metabolism, and is commonly associated with hypoxic or ischemic injuries (see HYPOXIA, BRAIN). An increase in extracellular fluid may be caused by increased brain capillary permeability (vasogenic edema), an osmotic gradient, local blockages in interstitial fluid pathways, or by obstruction of CSF flow (e.g., obstructive HYDROCEPHALUS). (From Childs Nerv Syst 1992 Sep; 8(6):301-6)	2.15	1	0
Cardiac Toxicity [description not available]	2.15	1	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.15	1	0
Carcinoma, Epidermoid [description not available]	2.78	3	0
Cancer of Larynx [description not available]	2.15	1	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)	2.78	3	0
Laryngeal Neoplasms Cancers or tumors of the LARYNX or any of its parts: the GLOTTIS; EPIGLOTTIS; LARYNGEAL CARTILAGES; LARYNGEAL MUSCLES; and VOCAL CORDS.	2.15	1	0
Tauopathies Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.	2.15	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	3.03	4	0
Left Ventricular Dysfunction [description not available]	2.81	3	0
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.	2.81	3	0
Lassitude [description not available]	7.96	5	5
Emesis [description not available]	9.1	7	5
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli.	7.96	5	5
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	9.39	8	6
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	9.1	7	5
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2.15	1	0
Acute Hepatic Failure [description not available]	2.15	1	0
Liver Failure, Acute A form of rapid-onset LIVER FAILURE, also known as fulminant hepatic failure, caused by severe liver injury or massive loss of HEPATOCYTES. It is characterized by sudden development of liver dysfunction and JAUNDICE. Acute liver failure may progress to exhibit cerebral dysfunction even HEPATIC COMA depending on the etiology that includes hepatic ISCHEMIA, drug toxicity, malignant infiltration, and viral hepatitis such as post-transfusion HEPATITIS B and HEPATITIS C.	2.15	1	0
ER-Negative PR-Negative HER2-Negative Breast Cancer [description not available]	2.15	1	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.	2.15	1	0
As If Personality [description not available]	2.15	1	0
Abnormal Deep Tendon Reflex [description not available]	2.54	2	0
MPTP Neurotoxicity Syndrome [description not available]	2.78	3	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.	3.7	10	0
Reflex, Abnormal An abnormal response to a stimulus applied to the sensory components of the nervous system. This may take the form of increased, decreased, or absent reflexes.	2.54	2	0
Angioneurotic Edema [description not available]	3.9	4	0
Microglossia [description not available]	2.15	1	0
Angioedema Swelling involving the deep DERMIS, subcutaneous, or submucosal tissues, representing localized EDEMA. Angioedema often occurs in the face, lips, tongue, and larynx.	3.9	4	0
Ache [description not available]	3.67	9	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	3.67	9	0
Colorectal Cancer [description not available]	8.53	7	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.	3.53	7	0
Diabetic Angiopathies VASCULAR DISEASES that are associated with DIABETES MELLITUS.	9.4	9	3
Fatty Liver, Nonalcoholic [description not available]	4.29	6	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	4.29	6	0
Cancer of Ovary [description not available]	5.22	11	1
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.	5.22	11	1
Kahler Disease [description not available]	7.98	7	4
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.	7.98	7	4
Infections, Chlamydia [description not available]	2.15	1	0
Chlamydia Infections Infections with bacteria of the genus CHLAMYDIA.	2.15	1	0
Liver Steatosis [description not available]	6.68	7	1
Cardiomyopathies, Primary [description not available]	2.15	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.	6.68	7	1
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).	2.15	1	0
Amentia [description not available]	2.15	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	5.12	10	0
Dementia An acquired organic mental disorder with loss of intellectual abilities of sufficient severity to interfere with social or occupational functioning. The dysfunction is multifaceted and involves memory, behavior, personality, judgment, attention, spatial relations, language, abstract thought, and other executive functions. The intellectual decline is usually progressive, and initially spares the level of consciousness.	2.15	1	0
Carcinoma, Non-Small Cell Lung [description not available]	3.33	6	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.	3.33	6	0
Cardiac Hypertrophy Enlargement of the HEART due to chamber HYPERTROPHY, an increase in wall thickness without an increase in the number of cells (MYOCYTES, CARDIAC). It is the result of increase in myocyte size, mitochondrial and myofibrillar mass, as well as changes in extracellular matrix.	3.92	4	0
Cardiomegaly Enlargement of the HEART, usually indicated by a cardiothoracic ratio above 0.50. Heart enlargement may involve the right, the left, or both HEART VENTRICLES or HEART ATRIA. Cardiomegaly is a nonspecific symptom seen in patients with chronic systolic heart failure (HEART FAILURE) or several forms of CARDIOMYOPATHIES.	3.92	4	0
Granulocytic Leukemia, Chronic [description not available]	3.42	7	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.	3.42	7	0
Chronic Lung Injury [description not available]	2.15	1	0
Alveolitis, Fibrosing [description not available]	2.15	1	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	2.15	1	0
Colicky Pain [description not available]	2.15	1	0
Abdominal Pain Sensation of discomfort, distress, or agony in the abdominal region.	2.15	1	0
Cardiovascular Stroke [description not available]	13.01	39	14
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	13.01	39	14
Alcohol Abuse [description not available]	2.44	2	0
Drug Withdrawal Symptoms [description not available]	3.18	5	0
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	2.44	2	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.	3.18	5	0
Apoplexy [description not available]	9.69	13	8
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)	9.69	13	8
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.	4.2	3	0
B Virus Infection [description not available]	3.38	2	0
Hyperactivity, Motor [description not available]	2.17	1	0
Dementia Praecox [description not available]	2.98	4	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.	2.98	4	0
Acute Lymphoid Leukemia [description not available]	2.53	2	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.	2.53	2	0
Basal Ganglia Diseases Diseases of the BASAL GANGLIA including the PUTAMEN; GLOBUS PALLIDUS; claustrum; AMYGDALA; and CAUDATE NUCLEUS. DYSKINESIAS (most notably involuntary movements and alterations of the rate of movement) represent the primary clinical manifestations of these disorders. Common etiologies include CEREBROVASCULAR DISORDERS; NEURODEGENERATIVE DISEASES; and CRANIOCEREBRAL TRAUMA.	2.17	1	0
Action Tremor [description not available]	4.32	4	1
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.	4.32	4	1
Carcinoma, Anaplastic [description not available]	2.97	4	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.	2.97	4	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	14.67	37	24
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	14.67	37	24
Cancer of Skin [description not available]	2.52	2	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.52	2	0
Endotoxemia A condition characterized by the presence of ENDOTOXINS in the blood. On lysis, the outer cell wall of gram-negative bacteria enters the systemic circulation and initiates a pathophysiologic cascade of pro-inflammatory mediators.	2.17	1	0
Polycystic Ovarian Syndrome [description not available]	5.43	2	2
Polycystic Ovary Syndrome A complex disorder characterized by infertility, HIRSUTISM; OBESITY; and various menstrual disturbances such as OLIGOMENORRHEA; AMENORRHEA; ANOVULATION. Polycystic ovary syndrome is usually associated with bilateral enlarged ovaries studded with atretic follicles, not with cysts. The term, polycystic ovary, is misleading.	5.43	2	2
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)	7.59	32	1
Genital Herpes [description not available]	2.17	1	0
Herpes Simplex Virus Infection [description not available]	4.08	3	1
Herpes Genitalis Infection of the genitals (GENITALIA) with HERPES SIMPLEX VIRUS in either the males or the females.	2.17	1	0
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	4.08	3	1
Caries, Dental [description not available]	2.17	1	0
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	2.17	1	0
Hematologic Malignancies [description not available]	3.41	2	0
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.85	3	0
Mast Cell Activation Disease [description not available]	2.17	1	0
Mastocytosis A rare neoplastic disorder characterized by a clonal proliferation of MAST CELLS, associated with KIT-D816 mutations, and accompanied by aberrant mast cell activation. The abnormal increase of MAST CELLS may occur in only the skin (MASTOCYTOSIS, CUTANEOUS), in extracutaneous tissues involving multiple organs (MASTOCYTOSIS, SYSTEMIC), or in solid tumors (MASTOCYTOMA).	2.17	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.	3.41	2	0
Heart Disease, Ischemic [description not available]	4.42	4	1
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).	4.42	4	1
Atherosclerotic Parkinsonism [description not available]	3.44	7	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)	3.44	7	0
Cardiac Remodeling, Ventricular [description not available]	3.22	5	0
Urinary Tract Infections Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.	10.52	10	9
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.98	4	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.	2.98	4	0
Lassa Virus Infection [description not available]	2.17	1	0
Lassa Fever An acute febrile human disease caused by the LASSA VIRUS.	2.17	1	0
Genital Tract Infections [description not available]	4.48	1	1
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).	2.83	3	0
Brain Vascular Disorders [description not available]	5.09	3	1
Coronary Heart Disease [description not available]	4.8	2	1
Diseases, Peripheral Vascular [description not available]	3.87	2	1
Cerebrovascular Disorders A spectrum of pathological conditions of impaired blood flow in the brain. They can involve vessels (ARTERIES or VEINS) in the CEREBRUM, the CEREBELLUM, and the BRAIN STEM. Major categories include INTRACRANIAL ARTERIOVENOUS MALFORMATIONS; BRAIN ISCHEMIA; CEREBRAL HEMORRHAGE; and others.	5.09	3	1
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	4.8	2	1
Peripheral Vascular Diseases Pathological processes involving any one of the BLOOD VESSELS in the vasculature outside the HEART.	3.87	2	1
Primary Peritonitis [description not available]	2.89	3	0
Infections, Staphylococcal [description not available]	3.02	4	0
Peritonitis INFLAMMATION of the PERITONEUM lining the ABDOMINAL CAVITY as the result of infectious, autoimmune, or chemical processes. Primary peritonitis is due to infection of the PERITONEAL CAVITY via hematogenous or lymphatic spread and without intra-abdominal source. Secondary peritonitis arises from the ABDOMINAL CAVITY itself through RUPTURE or ABSCESS of intra-abdominal organs.	2.89	3	0
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	3.02	4	0
Weight Gain Increase in BODY WEIGHT over existing weight.	11.91	18	9
Encephalopathy, Toxic [description not available]	2.21	1	0
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	6.5	4	4
Carcinoma, Ductal, Pancreatic [description not available]	2.83	3	0
Carcinoma, Pancreatic Ductal Carcinoma that arises from the PANCREATIC DUCTS. It accounts for the majority of cancers derived from the PANCREAS.	2.83	3	0
Pain, Chronic [description not available]	2.55	2	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.	2.55	2	0
Injury, Myocardial Reperfusion [description not available]	3.71	9	0
Ebola Hemorrhagic Fever [description not available]	2.52	2	0
Hemorrhagic Fever, Ebola A highly fatal, acute hemorrhagic fever caused by EBOLAVIRUS.	2.52	2	0
Cancer of Prostate [description not available]	3.9	12	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	3.9	12	0
Cerebral Ischemia [description not available]	5.04	9	1
Brain Inflammation [description not available]	2.55	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.	5.04	9	1
Encephalitis Inflammation of the BRAIN due to infection, autoimmune processes, toxins, and other conditions. Viral infections (see ENCEPHALITIS, VIRAL) are a relatively frequent cause of this condition.	2.55	2	0
Allodynia [description not available]	2.99	4	0
Morphine Abuse [description not available]	2.21	1	0
Weight Reduction [description not available]	7.92	13	2
Morphine Dependence Strong dependence, both physiological and emotional, upon morphine.	2.21	1	0
Weight Loss Decrease in existing BODY WEIGHT.	7.92	13	2
Age-Related Memory Disorders [description not available]	2.79	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.	2.78	3	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.	2.79	3	0
Hypergonadotropic Hypogonadism [description not available]	2.52	2	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).	2.52	2	0
Infection [description not available]	5.94	2	2
Infections Invasion of the host organism by microorganisms or their toxins or by parasites that can cause pathological conditions or diseases.	5.94	2	2
Arthritis, Degenerative [description not available]	2.52	2	0
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.	2.52	2	0
Central Nervous System Disease [description not available]	6.39	3	1
Viral Diseases [description not available]	4.29	4	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.	6.39	3	1
Virus Diseases A general term for diseases caused by viruses.	4.29	4	0
Polyarthritis [description not available]	3.68	3	0
Arthritis Acute or chronic inflammation of JOINTS.	3.68	3	0
Hypothermia, Accidental [description not available]	2.98	4	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.98	4	0
Malignant Melanoma [description not available]	3.3	6	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)	3.3	6	0
Curling Ulcer Acute stress DUODENAL ULCER, usually observed in patients with extensive third-degree burns.	4.79	2	1
Duodenal Ulcer A PEPTIC ULCER located in the DUODENUM.	4.79	2	1
Lactic Acidosis [description not available]	2.08	1	0
Hemorrhagic Shock [description not available]	2.08	1	0
Acidosis, Lactic Acidosis caused by accumulation of lactic acid more rapidly than it can be metabolized. It may occur spontaneously or in association with diseases such as DIABETES MELLITUS; LEUKEMIA; or LIVER FAILURE.	2.08	1	0
Anasarca [description not available]	8.54	13	2
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	8.54	13	2
Erosive Duodenitis [description not available]	2.08	1	0
Gastric Ulcer [description not available]	2.08	1	0
Infections, Helicobacter [description not available]	2.08	1	0
Duodenitis Inflammation of the DUODENUM section of the small intestine (INTESTINE, SMALL). Erosive duodenitis may cause bleeding in the UPPER GI TRACT and PEPTIC ULCER.	2.08	1	0
Gastritis Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.	2.08	1	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).	2.08	1	0
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.	2.08	1	0
Bilateral Headache [description not available]	6.53	3	2
Headache The symptom of PAIN in the cranial region. It may be an isolated benign occurrence or manifestation of a wide variety of HEADACHE DISORDERS.	6.53	3	2
Fasciola Infection [description not available]	5.05	9	1
Ovine Diseases [description not available]	3.86	2	1
Fascioliasis Liver disease caused by infections with parasitic flukes of the genus FASCIOLA, such as FASCIOLA HEPATICA.	5.05	9	1
Chronic Kidney Failure [description not available]	8.53	10	6
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.	8.53	10	6
Angina at Rest [description not available]	3.19	5	0
Angina, Unstable Precordial pain at rest, which may precede a MYOCARDIAL INFARCTION.	3.19	5	0
Sclerosis A pathological process consisting of hardening or fibrosis of an anatomical structure, often a vessel or a nerve.	2.1	1	0
Proteinuria The presence of proteins in the urine, an indicator of KIDNEY DISEASES.	2.1	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.	2.08	1	0
Hypermelanosis [description not available]	3.89	2	1
B16 Melanoma [description not available]	2.74	3	0
Hyperpigmentation Excessive pigmentation of the skin, usually as a result of increased epidermal or dermal melanin pigmentation, hypermelanosis. Hyperpigmentation can be localized or generalized. The condition may arise from exposure to light, chemicals or other substances, or from a primary metabolic imbalance.	3.89	2	1
Adverse Drug Event [description not available]	8.4	9	5
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.	8.4	9	5
Extensively Drug-Resistant Tuberculosis Tuberculosis resistant to ISONIAZID and RIFAMPIN and at least three of the six main classes of second-line drugs (AMINOGLYCOSIDES; polypeptide agents; FLUOROQUINOLONES; THIOAMIDES; CYCLOSERINE; and PARA-AMINOSALICYLIC ACID) as defined by the CDC.	5.61	4	0
Vascular Injuries [description not available]	2.48	2	0
Dermatoses [description not available]	2.1	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	2.1	1	0
Inadequate Sleep [description not available]	2.08	1	0
Nerve Pain [description not available]	3	4	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	3	4	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.1	1	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.	7.1	1	0
Experimental Neoplasms [description not available]	5.37	7	0
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	4.55	5	1
Hyperlipemia [description not available]	10.46	31	2
Hyperlipidemias Conditions with excess LIPIDS in the blood.	10.46	31	2
Anterior Circulation Transient Ischemic Attack [description not available]	2.79	3	0
Ischemic Attack, Transient Brief reversible episodes of focal, nonconvulsive ischemic dysfunction of the brain having a duration of less than 24 hours, and usually less than one hour, caused by transient thrombotic or embolic blood vessel occlusion or stenosis. Events may be classified by arterial distribution, temporal pattern, or etiology (e.g., embolic vs. thrombotic). (From Adams et al., Principles of Neurology, 6th ed, pp814-6)	2.79	3	0
Schistosoma japonicum Infection [description not available]	2.48	2	0
Libman-Sacks Disease [description not available]	2.1	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.	2.1	1	0
Bone Cancer [description not available]	3.93	4	0
Osteogenic Sarcoma [description not available]	4.12	5	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	3.93	4	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)	4.12	5	0
Recrudescence [description not available]	3.13	5	0
Hypospermatogenesis [description not available]	3.01	1	0
Azoospermia A condition of having no sperm present in the ejaculate (SEMEN).	3.01	1	0
Autosomal Dominant Juvenile Parkinson Disease [description not available]	3.57	8	0
Dyskinesia, Medication-Induced [description not available]	3.29	6	0
Dyskinesia, Drug-Induced Abnormal movements, including HYPERKINESIS; HYPOKINESIA; TREMOR; and DYSTONIA, associated with the use of certain medications or drugs. Muscles of the face, trunk, neck, and extremities are most commonly affected. Tardive dyskinesia refers to abnormal hyperkinetic movements of the muscles of the face, tongue, and neck associated with the use of neuroleptic agents (see ANTIPSYCHOTIC AGENTS). (Adams et al., Principles of Neurology, 6th ed, p1199)	3.29	6	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.	3.57	8	0
Leukemic Infiltration A pathologic change in leukemia in which leukemic cells permeate various organs at any stage of the disease. All types of leukemia show various degrees of infiltration, depending upon the type of leukemia. The degree of infiltration may vary from site to site. The liver and spleen are common sites of infiltration, the greatest appearing in myelocytic leukemia, but infiltration is seen also in the granulocytic and lymphocytic types. The kidney is also a common site and of the gastrointestinal system, the stomach and ileum are commonly involved. In lymphocytic leukemia the skin is often infiltrated. The central nervous system too is a common site.	2.1	1	0
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.	2.42	2	0
Adjuvant Arthritis [description not available]	2.95	4	0
HIV Coinfection [description not available]	5.26	4	1
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).	5.26	4	1
Extravascular Hemolysis [description not available]	3.12	5	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	3.12	5	0
Pulmonary Consumption [description not available]	13.53	22	18
Tuberculosis, Pulmonary MYCOBACTERIUM infections of the lung.	13.53	22	18
Neointima The new and thickened layer of scar tissue that forms on a PROSTHESIS, or as a result of vessel injury especially following ANGIOPLASTY or stent placement.	2.13	1	0
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.	2.75	3	0
Injuries, Spinal Cord [description not available]	2.13	1	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.).	2.13	1	0
Swine Diseases Diseases of domestic swine and of the wild boar of the genus Sus.	2.48	2	0
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	2.44	2	0
Electrocardiogram QT Prolonged [description not available]	3.5	1	1
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.	3.5	1	1
Muscular Weakness [description not available]	3.5	1	1
Symptom Cluster [description not available]	5.44	5	3
Syndrome A characteristic symptom complex.	5.44	5	3
Muscle Weakness A vague complaint of debility, fatigue, or exhaustion attributable to weakness of various muscles. The weakness can be characterized as subacute or chronic, often progressive, and is a manifestation of many muscle and neuromuscular diseases. (From Wyngaarden et al., Cecil Textbook of Medicine, 19th ed, p2251)	3.5	1	1
Anochlesia [description not available]	3.4	7	0
Blood Clot [description not available]	6.47	3	1
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	6.47	3	1
Osteoporotic Fractures Breaks in bones resulting from low bone mass and microarchitectural deterioration characteristic of OSTEOPOROSIS.	4.41	1	1
Bright Disease A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.	2.13	1	0
Interstitial Nephritis [description not available]	2.13	1	0
Glomerulonephritis Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.	2.13	1	0
Nephritis, Interstitial Inflammation of the interstitial tissue of the kidney. This term is generally used for primary inflammation of KIDNEY TUBULES and/or surrounding interstitium. For primary inflammation of glomerular interstitium, see GLOMERULONEPHRITIS. Infiltration of the inflammatory cells into the interstitial compartment results in EDEMA, increased spaces between the tubules, and tubular renal dysfunction.	2.13	1	0
Acute Onset Vascular Dementia [description not available]	3.38	2	0
Dementia, Vascular An imprecise term referring to dementia associated with CEREBROVASCULAR DISORDERS, including CEREBRAL INFARCTION (single or multiple), and conditions associated with chronic BRAIN ISCHEMIA. Diffuse, cortical, and subcortical subtypes have been described. (From Gerontol Geriatr 1998 Feb;31(1):36-44)	3.38	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.45	2	0
Dyslipidemia [description not available]	3.92	2	1
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.	3.92	2	1
Rhabdomyosarcoma A malignant solid tumor arising from mesenchymal tissues which normally differentiate to form striated muscle. It can occur in a wide variety of sites. It is divided into four distinct types: pleomorphic, predominantly in male adults; alveolar (RHABDOMYOSARCOMA, ALVEOLAR), mainly in adolescents and young adults; embryonal (RHABDOMYOSARCOMA, EMBRYONAL), predominantly in infants and children; and botryoidal, also in young children. It is one of the most frequently occurring soft tissue sarcomas and the most common in children under 15. (From Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p2186; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, pp1647-9)	2.13	1	0
Androgen-Independent Prostatic Cancer [description not available]	2.52	2	0
Prostatic Neoplasms, Castration-Resistant Tumors or cancer of the PROSTATE which can grow in the presence of low or residual amount of androgen hormones such as TESTOSTERONE.	2.52	2	0
Cancer of Kidney [description not available]	2.49	2	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	2.49	2	0
Atypical Mycobacterial Infection, Disseminated [description not available]	3.04	1	0
Colitis, Mucous [description not available]	3.87	2	1
Visceral Pain Pain originating from internal organs (VISCERA) associated with autonomic phenomena (PALLOR; SWEATING; NAUSEA; and VOMITING). It often becomes a REFERRED PAIN.	2.11	1	0
Irritable Bowel Syndrome A disorder with chronic or recurrent colonic symptoms without a clearcut etiology. This condition is characterized by chronic or recurrent ABDOMINAL PAIN, bloating, MUCUS in FECES, and an erratic disturbance of DEFECATION.	3.87	2	1
Facial Dermatoses Skin diseases involving the FACE.	3.51	1	1
Glue Abuse [description not available]	2.13	1	0
Dermatitis Medicamentosa [description not available]	3.46	2	0
Constriction, Pathological [description not available]	2.46	2	0
Constriction, Pathologic The condition of an anatomical structure's being constricted beyond normal dimensions.	2.46	2	0
Cholangiocellular Carcinoma [description not available]	4.99	4	0
Bile Duct Cancer [description not available]	4.99	4	0
Bile Duct Neoplasms Tumors or cancer of the BILE DUCTS.	4.99	4	0
Cholangiocarcinoma A malignant tumor arising from the epithelium of the BILE DUCTS.	4.99	4	0
Metastase [description not available]	2.13	1	0
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	2.13	1	0
Left Ventricular Hypertrophy [description not available]	2.13	1	0
Hypertrophy, Left Ventricular Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.	2.13	1	0
Tachyarrhythmia [description not available]	2.74	3	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.	2.74	3	0
Auricular Fibrillation [description not available]	2.13	1	0
Endomyocardial Fibrosis A condition characterized by the thickening of the ventricular ENDOCARDIUM and subendocardium (MYOCARDIUM), seen mostly in children and young adults in the TROPICAL CLIMATE. The fibrous tissue extends from the apex toward and often involves the HEART VALVES causing restrictive blood flow into the respective ventricles (CARDIOMYOPATHY, RESTRICTIVE).	2.13	1	0
Atrial Fibrillation Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.	2.13	1	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)	2.76	3	0
Delayed Effects, Prenatal Exposure [description not available]	2.49	2	0
Menopause, Premature The premature cessation of menses (MENSTRUATION) when the last menstrual period occurs in a woman under the age of 40. It is due to the depletion of OVARIAN FOLLICLES. Premature MENOPAUSE can be caused by diseases; OVARIECTOMY; RADIATION; chemicals; and chromosomal abnormalities.	2.13	1	0
Amnesia-Memory Loss [description not available]	2.13	1	0
Amnesia Pathologic partial or complete loss of the ability to recall past experiences (AMNESIA, RETROGRADE) or to form new memories (AMNESIA, ANTEROGRADE). This condition may be of organic or psychologic origin. Organic forms of amnesia are usually associated with dysfunction of the DIENCEPHALON or HIPPOCAMPUS. (From Adams et al., Principles of Neurology, 6th ed, pp426-7)	2.13	1	0
Anoxia-Ischemia, Brain [description not available]	2.13	1	0
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.	2.13	1	0
Hallucination of Body Sensation [description not available]	2.13	1	0
Agitation, Psychomotor [description not available]	2.13	1	0
Hallucinations Subjectively experienced sensations in the absence of an appropriate stimulus, but which are regarded by the individual as real. They may be of organic origin or associated with MENTAL DISORDERS.	2.13	1	0
Psychomotor Agitation A feeling of restlessness associated with increased motor activity. This may occur as a manifestation of nervous system drug toxicity or other conditions.	2.13	1	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	2.13	1	0
Chronic Pancreatitis [description not available]	2.13	1	0
Carcinoma, Intraepithelial [description not available]	2.13	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)	2.13	1	0
Carcinoma in Situ A lesion with cytological characteristics associated with invasive carcinoma but the tumor cells are confined to the epithelium of origin, without invasion of the basement membrane.	2.13	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.	2.13	1	0
Pancreatitis, Chronic INFLAMMATION of the PANCREAS that is characterized by recurring or persistent ABDOMINAL PAIN with or without STEATORRHEA or DIABETES MELLITUS. It is characterized by the irregular destruction of the pancreatic parenchyma which may be focal, segmental, or diffuse.	2.13	1	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.	2.15	1	0
Infectious Diseases [description not available]	3.06	1	0
Communicable Diseases An illness caused by an infectious agent or its toxins that occurs through the direct or indirect transmission of the infectious agent or its products from an infected individual or via an animal, vector or the inanimate environment to a susceptible animal or human host.	3.06	1	0
Aseptic Necrosis of Bone [description not available]	2.15	1	0
Osteonecrosis Death of a bone or part of a bone, either atraumatic or posttraumatic.	2.15	1	0
Nephrolithiasis Formation of stones in the KIDNEY.	2.13	1	0
Vasculitis, Retinal [description not available]	2.13	1	0
Retinal Vasculitis Inflammation of the retinal vasculature with various causes including infectious disease; LUPUS ERYTHEMATOSUS, SYSTEMIC; MULTIPLE SCLEROSIS; BEHCET SYNDROME; and CHORIORETINITIS.	2.13	1	0
Arterial Diseases, Carotid [description not available]	4.17	3	1
Carotid Artery Diseases Pathological conditions involving the CAROTID ARTERIES, including the common, internal, and external carotid arteries. ATHEROSCLEROSIS and TRAUMA are relatively frequent causes of carotid artery pathology.	4.17	3	1
Abnormalities, Autosome [description not available]	2.44	2	0
Hepatitis, Animal INFLAMMATION of the LIVER in non-human animals.	2.04	1	0
Asystole [description not available]	2.96	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.	2.96	1	0
Cholera Infantum [description not available]	5.25	2	2
Bodily Distress Disorder [description not available]	5.06	3	3
Clonorchiasis Infection of the biliary passages with CLONORCHIS SINENSIS, also called Opisthorchis sinensis. It may lead to inflammation of the biliary tract, proliferation of biliary epithelium, progressive portal fibrosis, and sometimes bile duct carcinoma. Extension to the liver may lead to fatty changes and cirrhosis. (From Dorland, 27th ed)	2.74	3	0
Diseases, Metabolic [description not available]	2.75	3	0
Metabolic Diseases Generic term for diseases caused by an abnormal metabolic process. It can be congenital due to inherited enzyme abnormality (METABOLISM, INBORN ERRORS) or acquired due to disease of an endocrine organ or failure of a metabolically important organ such as the liver. (Stedman, 26th ed)	2.75	3	0
Sarcoma, Epithelioid [description not available]	2.05	1	0
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	2.05	1	0
(pPNET) Peripheral Primitive Neuroectodermal Tumors [description not available]	2.05	1	0
Neuroectodermal Tumors, Primitive, Peripheral A group of highly cellular primitive round cell neoplasms which occur extracranially in soft tissue and bone and are derived from embryonal neural crest cells. These tumors occur primarily in children and adolescents and share a number of characteristics with EWING SARCOMA.	2.05	1	0
Iron Overload An excessive accumulation of iron in the body due to a greater than normal absorption of iron from the gastrointestinal tract or from parenteral injection. This may arise from idiopathic hemochromatosis, excessive iron intake, chronic alcoholism, certain types of refractory anemia, or transfusional hemosiderosis. (From Churchill's Illustrated Medical Dictionary, 1989)	8.38	2	0
Bacterial Infections, Gram-Positive [description not available]	3.38	2	0
Gram-Positive Bacterial Infections Infections caused by bacteria that retain the crystal violet stain (positive) when treated by the gram-staining method.	3.38	2	0
Organophosphorus Poisoning [description not available]	2.43	2	0
Organophosphate Poisoning Poisoning due to exposure to ORGANOPHOSPHORUS COMPOUNDS, such as ORGANOPHOSPHATES; ORGANOTHIOPHOSPHATES; and ORGANOTHIOPHOSPHONATES.	2.43	2	0
Infections, Respiratory [description not available]	3.32	2	0
Respiratory Tract Infections Invasion of the host RESPIRATORY SYSTEM by microorganisms, usually leading to pathological processes or diseases.	3.32	2	0
Long Sleeper Syndrome [description not available]	6.46	3	2
Briquet Syndrome [description not available]	3.44	1	1
Asthenia Clinical sign or symptom manifested as debility, or lack or loss of strength and energy.	5.05	3	3
Sleep Wake Disorders Abnormal sleep-wake schedule or pattern associated with the CIRCADIAN RHYTHM which affect the length, timing, and/or rigidity of the sleep-wake cycle relative to the day-night cycle.	6.46	3	2
Somatoform Disorders Disorders having the presence of physical symptoms that suggest a general medical condition but that are not fully explained by another medical condition, by the direct effects of a substance, or by another mental disorder. The MEDICALLY UNEXPLAINED SYMPTOMS must cause clinically significant distress or impairment in social, occupational, or other areas of functioning. In contrast to FACTITIOUS DISORDERS and MALINGERING, the physical symptoms are not under voluntary control. (APA, DSM-V)	3.44	1	1
Angiomatosis Retinae [description not available]	2.05	1	0
von Hippel-Lindau Disease An autosomal dominant disorder caused by mutations in a tumor suppressor gene. This syndrome is characterized by abnormal growth of small blood vessels leading to a host of neoplasms. They include HEMANGIOBLASTOMA in the RETINA; CEREBELLUM; and SPINAL CORD; PHEOCHROMOCYTOMA; pancreatic tumors; and renal cell carcinoma (see CARCINOMA, RENAL CELL). Common clinical signs include HYPERTENSION and neurological dysfunctions.	2.05	1	0
Donohue Syndrome Rare autosomal recessive syndrome of extreme insulin resistance due to mutations in the binding domain of INSULIN RECEPTOR. Clinical features include severe intrauterine and postnatal growth restriction, characteristic dysmorphic FACIES; HIRSUTISM; VIRILIZATION; multiple endocrine abnormalities, and early death.	2.05	1	0
Incontinentia Pigmenti Achromians [description not available]	2.06	1	0
Enlarged Spleen [description not available]	2.06	1	0
Acute Myelogenous Leukemia [description not available]	4.05	5	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.	4.05	5	0
Respiratory Syndrome, Acute, Severe [description not available]	2.06	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.	2.06	1	0
Pyrexia [description not available]	3.78	2	1
Fever An abnormal elevation of body temperature, usually as a result of a pathologic process.	3.78	2	1
Acute Brain Injuries [description not available]	2.06	1	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.	2.06	1	0
Echinostomiasis Infection by flukes of the genus Echinostoma.	2.45	2	0
ANS (Autonomic Nervous System) Diseases [description not available]	3.44	1	1
Behavior Disorders [description not available]	3.44	1	1
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.	3.44	1	1
Hepatic Insufficiency Conditions in which the LIVER functions fall below the normal ranges. Severe hepatic insufficiency may cause LIVER FAILURE or DEATH. Treatment may include LIVER TRANSPLANTATION.	3.45	1	1
Addiction, Opioid [description not available]	2.07	1	0
Opioid-Related Disorders Disorders related to or resulting from abuse or misuse of OPIOIDS.	2.07	1	0
AIDS-Related Opportunistic Infections Opportunistic infections found in patients who test positive for human immunodeficiency virus (HIV). The most common include PNEUMOCYSTIS PNEUMONIA, Kaposi's sarcoma, cryptosporidiosis, herpes simplex, toxoplasmosis, cryptococcosis, and infections with Mycobacterium avium complex, Microsporidium, and Cytomegalovirus.	3.37	2	0
Leucocythaemia [description not available]	3.29	6	0
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)	3.29	6	0
Deficiency, Vitamin B 12 [description not available]	2.98	1	0
Vitamin B 12 Deficiency A nutritional condition produced by a deficiency of VITAMIN B 12 in the diet, characterized by megaloblastic anemia. Since vitamin B 12 is not present in plants, humans have obtained their supply from animal products, from multivitamin supplements in the form of pills, and as additives to food preparations. A wide variety of neuropsychiatric abnormalities is also seen in vitamin B 12 deficiency and appears to be due to an undefined defect involving myelin synthesis. (From Cecil Textbook of Medicine, 19th ed, p848)	2.98	1	0
Acid beta-Glucosidase Deficiency [description not available]	3.67	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.	3.67	3	0
Asymmetric Diabetic Proximal Motor Neuropathy [description not available]	2.07	1	0
Peripheral Nerve Diseases [description not available]	2.07	1	0
Diabetic Neuropathies Peripheral, autonomic, and cranial nerve disorders that are associated with DIABETES MELLITUS. These conditions usually result from diabetic microvascular injury involving small blood vessels that supply nerves (VASA NERVORUM). Relatively common conditions which may be associated with diabetic neuropathy include third nerve palsy (see OCULOMOTOR NERVE DISEASES); MONONEUROPATHY; mononeuropathy multiplex; diabetic amyotrophy; a painful POLYNEUROPATHY; autonomic neuropathy; and thoracoabdominal neuropathy. (From Adams et al., Principles of Neurology, 6th ed, p1325)	2.07	1	0
Peripheral Nervous System Diseases Diseases of the peripheral nerves external to the brain and spinal cord, which includes diseases of the nerve roots, ganglia, plexi, autonomic nerves, sensory nerves, and motor nerves.	2.07	1	0
Bacterial Disease [description not available]	2.06	1	0
Candida Infection [description not available]	2.45	2	0
Bacterial Infections Infections by bacteria, general or unspecified.	2.06	1	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)	2.45	2	0
Abnormal Movements [description not available]	2.06	1	0
Ambulation Disorders, Neurologic [description not available]	2.07	1	0
Chronic Illness [description not available]	5.97	5	2
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).	5.97	5	2
Anxiety Neuroses [description not available]	2.06	1	0
Anxiety Disorders Persistent and disabling ANXIETY.	2.06	1	0
Chronic Insomnia [description not available]	3.45	1	1
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.	3.45	1	1
Acute Kidney Failure [description not available]	2.07	1	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.	2.07	1	0
Blood Poisoning [description not available]	2.07	1	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.	2.07	1	0
Metabolic Acidosis [description not available]	2.07	1	0
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	2.07	1	0
Audiogenic Epilepsy [description not available]	2.48	2	0
Epilepsy, Reflex A subtype of epilepsy characterized by seizures that are consistently provoked by a certain specific stimulus. Auditory, visual, and somatosensory stimuli as well as the acts of writing, reading, eating, and decision making are examples of events or activities that may induce seizure activity in affected individuals. (From Neurol Clin 1994 Feb;12(1):57-8)	2.48	2	0
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	2.07	1	0
Dyskinesia Syndromes [description not available]	2.43	2	0
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	2.43	2	0
Diabetic Feet [description not available]	4.37	1	1
Diabetic Foot Common foot problems in persons with DIABETES MELLITUS, caused by any combination of factors such as DIABETIC NEUROPATHIES; PERIPHERAL VASCULAR DISEASES; and INFECTION. With the loss of sensation and poor circulation, injuries and infections often lead to severe foot ulceration, GANGRENE and AMPUTATION.	4.37	1	1
Brain Hemorrhage, Cerebral, Traumatic [description not available]	2.07	1	0
Blood Pressure, Low [description not available]	3.63	3	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.	3.63	3	0
Glomerulonephritis, Lupus [description not available]	2.08	1	0
Lupus Nephritis Glomerulonephritis associated with autoimmune disease SYSTEMIC LUPUS ERYTHEMATOSUS. Lupus nephritis is histologically classified into 6 classes: class I - normal glomeruli, class II - pure mesangial alterations, class III - focal segmental glomerulonephritis, class IV - diffuse glomerulonephritis, class V - diffuse membranous glomerulonephritis, and class VI - advanced sclerosing glomerulonephritis (The World Health Organization classification 1982).	2.08	1	0
Acute Necrotizing Pancreatitis [description not available]	2.08	1	0
Graft-Versus-Host Disease [description not available]	2.01	1	0
Graft vs Host Disease The clinical entity characterized by anorexia, diarrhea, loss of hair, leukopenia, thrombocytopenia, growth retardation, and eventual death brought about by the GRAFT VS HOST REACTION.	2.01	1	0
Leukemia, Lymphocytic, T Cell [description not available]	2.01	1	0
Leukemia, T-Cell A malignant disease of the T-LYMPHOCYTES in the bone marrow, thymus, and/or blood.	2.01	1	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	2.42	2	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.	2.42	2	0
Itching [description not available]	2.02	1	0
Pruritus An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.	2.02	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.	2.02	1	0
Idiopathic Hypoparathyroidism A condition of low or absent PTH level and HYPOCALCEMIA. It usually occurs as part of an autoimmune syndrome.	2.02	1	0
Hyperparathyroidism A condition of abnormally elevated output of PARATHYROID HORMONE (or PTH) triggering responses that increase blood CALCIUM. It is characterized by HYPERCALCEMIA and BONE RESORPTION, eventually leading to bone diseases. PRIMARY HYPERPARATHYROIDISM is caused by parathyroid HYPERPLASIA or PARATHYROID NEOPLASMS. SECONDARY HYPERPARATHYROIDISM is increased PTH secretion in response to HYPOCALCEMIA, usually caused by chronic KIDNEY DISEASES.	2.02	1	0
Hypoparathyroidism A condition caused by a deficiency of PARATHYROID HORMONE (or PTH). It is characterized by HYPOCALCEMIA and hyperphosphatemia. Hypocalcemia leads to TETANY. The acquired form is due to removal or injuries to the PARATHYROID GLANDS. The congenital form is due to mutations of genes, such as TBX1; (see DIGEORGE SYNDROME); CASR encoding CALCIUM-SENSING RECEPTOR; or PTH encoding parathyroid hormone.	2.02	1	0
Acne [description not available]	2.02	1	0
Hormone-Dependent Neoplasms [description not available]	2.02	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.	2.02	1	0
Cancer of the Vulva [description not available]	2.02	1	0
Vulvar Neoplasms Tumors or cancer of the VULVA.	2.02	1	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)	2.41	2	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.	2.38	2	0
Anterior Choroidal Artery Infarction [description not available]	2.69	3	0
Cerebral Infarction The formation of an area of NECROSIS in the CEREBRUM caused by an insufficiency of arterial or venous blood flow. Infarcts of the cerebrum are generally classified by hemisphere (i.e., left vs. right), lobe (e.g., frontal lobe infarction), arterial distribution (e.g., INFARCTION, ANTERIOR CEREBRAL ARTERY), and etiology (e.g., embolic infarction).	2.69	3	0
Lymph Node Metastasis [description not available]	2.02	1	0
T-Cell Lymphoma [description not available]	2.02	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)	2.02	1	0
Lymphoma, T-Cell A group of heterogeneous lymphoid tumors representing malignant transformations of T-lymphocytes.	2.02	1	0
Retinal Diseases Diseases involving the RETINA.	2.03	1	0
Carcinoma, Large Cell A tumor of undifferentiated (anaplastic) cells of large size. It is usually bronchogenic. (From Dorland, 27th ed)	2.03	1	0
Teratocarcinoma A malignant neoplasm consisting of elements of teratoma with those of embryonal carcinoma or choriocarcinoma, or both. It occurs most often in the testis. (Dorland, 27th ed)	2.03	1	0
Atypical Chronic Myeloid Leukemia [description not available]	2.03	1	0
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.	8.62	3	0
Health Care Associated Infection [description not available]	3.78	2	1
Cross Infection Any infection which a patient contracts in a health-care institution.	3.78	2	1
Bilharziasis [description not available]	2.03	1	0
Schistosomiasis Infection with flukes (trematodes) of the genus SCHISTOSOMA. Three species produce the most frequent clinical diseases: SCHISTOSOMA HAEMATOBIUM (endemic in Africa and the Middle East), SCHISTOSOMA MANSONI (in Egypt, northern and southern Africa, some West Indies islands, northern 2/3 of South America), and SCHISTOSOMA JAPONICUM (in Japan, China, the Philippines, Celebes, Thailand, Laos). S. mansoni is often seen in Puerto Ricans living in the United States.	2.03	1	0
Di Guglielmo Disease [description not available]	2.03	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.	2.03	1	0
Leukemoid Reaction A peripheral blood picture resembling that of leukemia or indistinguishable from it on the basis of morphologic appearance alone. (Dorland, 27th ed)	2.03	1	0
Hypertension, Renal Persistent high BLOOD PRESSURE due to KIDNEY DISEASES, such as those involving the renal parenchyma, the renal vasculature, or tumors that secrete RENIN.	2.03	1	0
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	4.29	4	1
Emergencies Situations or conditions requiring immediate intervention to avoid serious adverse results.	1.96	1	0
Bleeding [description not available]	2.36	2	0
Hemorrhage Bleeding or escape of blood from a vessel.	2.36	2	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	1.96	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.	4.05	3	1
Cerebral Arteriosclerosis [description not available]	1.96	1	0
Intracranial Arteriosclerosis Vascular diseases characterized by thickening and hardening of the walls of ARTERIES inside the SKULL. There are three subtypes: (1) atherosclerosis with fatty deposits in the ARTERIAL INTIMA; (2) Monckeberg's sclerosis with calcium deposits in the media and (3) arteriolosclerosis involving the small caliber arteries. Clinical signs include HEADACHE; CONFUSION; transient blindness (AMAUROSIS FUGAX); speech impairment; and HEMIPARESIS.	1.96	1	0
Brain Disorders [description not available]	2.38	2	0
Break-Bone Fever [description not available]	2.36	2	0
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	2.38	2	0
Dengue An acute febrile disease transmitted by the bite of AEDES mosquitoes infected with DENGUE VIRUS. It is self-limiting and characterized by fever, myalgia, headache, and rash. SEVERE DENGUE is a more virulent form of dengue.	2.36	2	0
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	1.96	1	0
Tooth Discoloration Any change in the hue, color, or translucency of a tooth due to any cause. Restorative filling materials, drugs (both topical and systemic), pulpal necrosis, or hemorrhage may be responsible. (Jablonski, Dictionary of Dentistry, 1992, p253)	1.96	1	0
Gingivitis Inflammation of gum tissue (GINGIVA) without loss of connective tissue.	2.37	2	0
Contact Dermatitis [description not available]	1.96	1	0
Allergy, Drug [description not available]	1.96	1	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	1.96	1	0
Drug Hypersensitivity Immunologically mediated adverse reactions to medicinal substances used legally or illegally.	1.96	1	0
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	1.96	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.	1.96	1	0
Active Hyperemia [description not available]	1.98	1	0
Hyperemia The presence of an increased amount of blood in a body part or an organ leading to congestion or engorgement of blood vessels. Hyperemia can be due to increase of blood flow into the area (active or arterial), or due to obstruction of outflow of blood from the area (passive or venous).	1.98	1	0
Chemical Dependence [description not available]	2.9	1	0
Substance-Related Disorders Disorders related to substance use or abuse.	2.9	1	0
Adenoma, beta-Cell [description not available]	1.98	1	0
Insulinoma A benign tumor of the PANCREATIC BETA CELLS. Insulinoma secretes excess INSULIN resulting in HYPOGLYCEMIA.	1.98	1	0
Elevated Cholesterol [description not available]	2.87	4	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.	2.87	4	0
Alpha Virus Infections [description not available]	1.99	1	0
Cancer of Stomach [description not available]	1.99	1	0
Stomach Neoplasms Tumors or cancer of the STOMACH.	1.99	1	0
Cocaine Abuse [description not available]	1.99	1	0
Cocaine-Related Disorders Disorders related or resulting from use of cocaine.	1.99	1	0
Obstructive Lung Diseases [description not available]	3.77	2	1
Lung Diseases, Obstructive Any disorder marked by obstruction of conducting airways of the lung. AIRWAY OBSTRUCTION may be acute, chronic, intermittent, or persistent.	3.77	2	1
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.	2	1	0
Trypanosomiasis Infection with protozoa of the genus TRYPANOSOMA.	2	1	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.	2.01	1	0
Cancer of Endometrium [description not available]	2.01	1	0
Endometrial Neoplasms Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.	2.01	1	0
Viral Hepatitis, Human [description not available]	2.92	1	0
Hepatitis, Viral, Human INFLAMMATION of the LIVER in humans due to infection by VIRUSES. There are several significant types of human viral hepatitis with infection caused by enteric-transmission (HEPATITIS A; HEPATITIS E) or blood transfusion (HEPATITIS B; HEPATITIS C; and HEPATITIS D).	2.92	1	0
Arbovirus Infections Infections caused by arthropod-borne viruses, general or unspecified.	2.35	2	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.	1.95	1	0
Carcinoma 256, Walker A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)	1.95	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	1.95	1	0
EHS Tumor [description not available]	1.95	1	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	1.95	1	0
Leukemia L 1210 [description not available]	2.36	2	0
Experimental Radiation Injuries [description not available]	1.95	1	0
Cane-Cutter Fever [description not available]	1.98	1	0
Leptospirosis Infections with bacteria of the genus LEPTOSPIRA.	1.98	1	0
Hypophosphatasia A genetic metabolic disorder resulting from serum and bone alkaline phosphatase deficiency leading to hypercalcemia, ethanolamine phosphatemia, and ethanolamine phosphaturia. Clinical manifestations include severe skeletal defects resembling vitamin D-resistant rickets, failure of the calvarium to calcify, dyspnea, cyanosis, vomiting, constipation, renal calcinosis, failure to thrive, disorders of movement, beading of the costochondral junction, and rachitic bone changes. (From Dorland, 27th ed)	2.89	1	0
Bronchitis Inflammation of the large airways in the lung including any part of the BRONCHI, from the PRIMARY BRONCHI to the TERTIARY BRONCHI.	1.98	1	0
Antibody Deficiency Syndrome [description not available]	1.97	1	0
Immunologic Deficiency Syndromes Syndromes in which there is a deficiency or defect in the mechanisms of immunity, either cellular or humoral.	1.97	1	0
Anaphylactic Reaction [description not available]	1.97	1	0
Anaphylaxis An acute hypersensitivity reaction due to exposure to a previously encountered ANTIGEN. The reaction may include rapidly progressing URTICARIA, respiratory distress, vascular collapse, systemic SHOCK, and death.	1.97	1	0
Centriacinar Emphysema [description not available]	1.97	1	0
Hematuria Presence of blood in the urine.	1.96	1	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
Hepatitis, Infectious [description not available]	1.96	1	0
Hepatitis B Virus Infection [description not available]	1.96	1	0
Viremia The presence of viruses in the blood.	1.96	1	0
Hepatitis A INFLAMMATION of the LIVER in humans caused by a member of the HEPATOVIRUS genus, HUMAN HEPATITIS A VIRUS. It can be transmitted through fecal contamination of food or water.	1.96	1	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.	1.96	1	0
Emphysema A pathological accumulation of air in tissues or organs.	1.96	1	0

adamantane

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Research Demand Index: 52.69

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