vx profile

VX nerve agent : A organic thiophosphate that is the ethyl ester of S-{2-[di(propan-2-yl)amino]ethyl} O hydrogen methylphosphonothioate. A toxic nerve agent used in chemical warfare. [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]

ID Source	ID
PubMed CID	39793
CHEMBL ID	483105
CHEBI ID	136185
SCHEMBL ID	215425
MeSH ID	M0054577

Synonym
65167-63-7
65167-64-8
o-ethyl s-2-diisopropylaminoethyl methyl phosphonothiolate
(s)-s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl methylphosphonothioate
ethyl s-2-diisopropylaminoethyl methylphosphonothiolate
methylphosphonothioic acid s-(2-(bis(methylethyl)amino)ethyl) o-ethyl ester
methylphosphonothioic acid, s-(2-diisopropylamino)ethyl o-ethyl ester
hsdb 6459
(+-)-s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl methylphosphonothioate
phosphonothioic acid, methyl-, s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl ester
phosphonothioic acid, methyl-, s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl ester, (-)-
tx 60
ea 1701
phosphonothioic acid, methyl-, s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl ester, (+-)-
phosphonothioic acid, methyl-, s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl ester, (+)-
ethyl s-dimethylaminoethyl methylphosphonothiolate
methylphosphonothioic acid s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl ester
o-ethyl s-(2-diisopropylaminoethyl)methylphosphonothioate
ccris 3351
s-(2-diisopropylaminoethyl) o-ethyl methyl phosphonothiolate
phosphonothioic acid, methyl-, s-(2-(diisopropylamino)ethyl) o-ethyl ester
vx (van)
ethyl-s-diisopropylaminoethyl methylthiophosphonate
(r)-s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl methylphosphonothioate
o-ethyl-s-2-diisopropylaminoethylester kyseliny methylthiofosfonove [czech]
s-(2-diisopropylaminoethyl)-o-ethyl methylphosphonothiolate
brn 1949015
VX ,
s-{2-[di(propan-2-yl)amino]ethyl} o-ethyl methylphosphonothioate
o-ethyl s-(2-diisopropylaminoethyl) methylphosphonothioate
o-ethyl-s-[2-(n,n-diisopropylamino)ethyl] ester
50782-69-9
vx nerve agent
CHEBI:136185
bdbm50027342
CHEMBL483105 ,
9a4381183b ,
unii-9a4381183b
o-ethyl-s-2-diisopropylaminoethylester kyseliny methylthiofosfonove
phosphonothioic acid, p-methyl-, s-(2-(bis(1-methylethyl)amino)ethyl) o-ethyl ester
o-ethyl s-(2-(diisopropylamino)ethyl)methylphosphonothioate
vx [mi]
o-ethyl s-2-diisopropylaminoethyl methylphosphonothioate
vx [hsdb]
SCHEMBL215425
phosphonohioic acid, methyl, o-ethyl-s-(2-diisopropylaminoethyl) ester
o-ethyl s-2-diisopropylaminoethyl methylphosphonothiolate
JJIUCEJQJXNMHV-UHFFFAOYSA-N
methyl-phosphonothioic acid s-(2-diisopropylamino-ethyl) ester o-ethyl ester
s-[2-(diisopropylamino)ethyl] o-ethyl methylphosphonothioate
vx agent
o-ethyl s-(2-diisopropylaminoethyl) methylthiophosphonate
phosphonothioic acid, methyl-, s-[2-[bis(1-methylethyl)amino]ethyl] o-ethyl ester
vx.
o-ethyl s-[2-(diisopropylamino)ethyl] methylphosphonothioate
DTXSID80866161
Q421809
PD193129

Research Excerpts

Overview

VX is a highly toxic organophosphorus nerve agent. It reacts with a variety of endogenous proteins such as serum albumin under formation of adducts.

Excerpt	Reference	Relevance
"VX is a highly toxic organophosphorus nerve agent that reacts with a variety of endogenous proteins such as serum albumin under formation of adducts that can be targeted by analytical methods for biomedical verification of exposure. "	( Evidence of nerve agent VX exposure in rat plasma by detection of albumin-adducts in vitro and in vivo. John, H; Kranawetvogl, A; Kranawetvogl, T; Scheidegger, L; Steinritz, D; Thiermann, H; Wille, T; Worek, F, 2023)	2.66

Actions

Excerpt	Reference	Relevance
"VX induced an increase in LDH release in a concentration-dependent manner."	( VX-induced cell death involves activation of caspase-3 in cultured rat cortical neurons. Tenn, CC; Wang, Y, 2007)	2.5

Treatment

VX (10 or 20 x LD50) poisoned animals with oxime plus atropine improved respiration to various extents, restored circulation and prolonged the survival time. HLö 7 was more effective than HI 6 after VX 90 micrograms/kg.

Excerpt	Reference	Relevance
"VX treatment inhibited 50% of the AChE activity in brain and muscle of AChE+/+ and +/- mice, 50% of the BChE activity in all three AChE genotypes, but did not significantly inhibit acylpeptide hydrolase activity."	( Evidence for nonacetylcholinesterase targets of organophosphorus nerve agent: supersensitivity of acetylcholinesterase knockout mouse to VX lethality. Anderson, RS; Broomfield, CA; Duysen, EG; Li, B; Lockridge, O; Schopfer, LM; Xie, W, 2001)	1.23
"The VX-treated animals exhibited no clinical signs, despite aggressive dosing, and there were no significant changes in the electrophysiologic characteristics (conduction velocity, relative refractory period, strength-duration threshold) of either peripheral nerve."	( DFP-induced elevation of strength-duration threshold in hen peripheral nerve. Anderson, RJ; Henderson, JD; Robertson, DG; Wilson, BW, 1988)	0.76
"The treatment of VX (10 or 20 x LD50) poisoned animals with oxime plus atropine improved respiration to various extents, restored circulation and prolonged the survival time, HLö 7 being more effective than HI 6 after VX 90 micrograms/kg."	( Effect of atropine, HLö 7 and HI 6 on respiratory and circulatory function in guinea-pigs poisoned by O-ethyl S-[2-(diisopropylamino) ethyl] methylphosponothioate (VX). Kirchner, T; Szinicz, L; Worek, F, 1994)	0.81

Toxicity

The minimal effective concentration for two of the VX analogues was 2 orders of magnitude more toxic than the analogue for GD. Doses of PO and VX were at or above LD50 levels.

Excerpt	Reference	Relevance
" Doses of PO and VX were at or above LD50 levels."	( Toxicity of repeated doses of organophosphorus esters in the chicken. Dacre, JC; Goldman, M; Henderson, JD; Higgins, RJ; Kellner, TP; Wilson, BW, 1988)	0.61
"Fetal bovine serum acetylcholinesterase (FBS-AChE) protected mice from multiple LD50 doses of organophosphorus (OP) nerve agents."	( Acetylcholinesterase prophylaxis against organophosphate toxicity. Doctor, BP; Jones, D; Koplovitz, I; Rush, RS; Wolfe, AD, 1987)	0.27
" The oral LD50 in hens is 1186 mg kg-1."	( Neurotoxicity assessment of O-ethyl-O'-(2-diisopropylaminoethyl) methylphosphonite (QL) in hens. Bergmann, J; Olajos, EJ; Wall, H; Weimer, JT, 1986)	0.27
"Butyrylcholinesterase purified from human plasma (HuBChE) was evaluated both in vitro and in vivo in mice and rats as a single prophylactic antidote against the lethal effects of highly toxic organophosphates (OP)."	( Human butyrylcholinesterase as a general prophylactic antidote for nerve agent toxicity. In vitro and in vivo quantitative characterization. Ashani, Y; Cohen, E; Grunwald, J; Marcus, D; Papier, Y; Raveh, L, 1993)	0.29
" The minimal effective concentration for two of the VX analogues was 2 orders of magnitude more toxic than the analogue for GD and 4 orders of magnitude more toxic than the analogue for GB."	( Organophosphate nerve agent toxicity in Hydra attenuata. Huebner, HJ; Li, Y; Lum, KT; Phillips, TD; Raushel, FM, 2003)	0.57
" We investigated the toxic effects of nerve agent VX on the respiratory dynamics of guinea pigs following exposure to 90."	( Acute toxic effects of nerve agent VX on respiratory dynamics and functions following microinsillation inhalation exposure in guinea pigs. Doctor, BP; Gordon, RK; Graham, JR; Moran, TS; Nambiar, MP; Rezk, PE; Sciuto, AM, 2007)	0.87
" The lowest observable adverse effect level (LOAEL) for the production of major clinical signs was determined to be 42."	( Determination of threshold adverse effect doses of percutaneous VX exposure in African green monkeys. Benton, BJ; Byers, CE; Genovese, RF; Jakubowski, EM; Mioduszewski, RJ; Oubre, JL; Settle, TJ; Steinbach, TJ, 2011)	0.61
" Recently, a chimeric PON1 mutant, IIG1, was engineered toward the hydrolysis of the toxic isomers of soman and cyclosarin with high in vitro catalytic efficiency."	( Efficacy of the rePON1 mutant IIG1 to prevent cyclosarin toxicity in vivo and to detoxify structurally different nerve agents in vitro. Ashani, Y; Goldsmith, M; Leader, H; Seeger, T; Sussman, JS; Tawfik, D; Thiermann, H; Wille, T; Worek, F, 2014)	0.4
"Prevention of the penetration of toxic agents through the skin is crucial for both military troops and civilian populations."	( Dermostyx (IB1) - High efficacy and safe topical skin protectant against percutaneous toxic agents. Amir, A; Barness, I; Dachir, S; Eisenkraft, A; Fishbine, E; Kadar, T; Meshulam, J; Sahar, R, 2017)	0.46
" In the ED50 study, male guinea pigs clipped of hair received 2x LD50 topical challenges of undiluted Russian VX (VR), VX, or phorate oxon (PHO) and, at the onset of cholinergic signs, IM therapy of atropine (0."	( Toxicity and median effective doses of oxime therapies against percutaneous organophosphorus pesticide and nerve agent challenges in the Hartley guinea pig. Babin, MC; Jett, DA; Platoff, GE; Snider, TH; Yeung, DT, 2016)	0.65
" We further evaluated the efficacy of two different antidotal regimens, one comprising a single and the other repeated administration of antidotes, in countering the toxic effects of the exposure."	( Repetitive antidotal treatment is crucial in eliminating eye pathology, respiratory toxicity and death following whole-body VX vapor exposure in freely moving rats. Bloch-Shilderman, E; Cohen, L; Egoz, I; Gez, R; Gutman, H; Nili, U; Rabinovitz, I; Yacov, G, 2019)	0.72
" Taken together, these results suggest that Hu BChE-OP conjugates are safe and provide further support for the development of Hu BChE as a bioscavenger for use in humans."	( Conjugates of human serum butyrylcholinesterase and nerve agents are behaviorally safe in rhesus macaques. Myers, TM; Saxena, A; Sipos, ML, 2021)	0.62

Bioavailability

The amount of radioactivity in each sample was measured by liquid scintillation counting, from which the skin absorption rate and dose distribution of VX were calculated. In vivo in swine, absorption rate constants were practically identical for VX and VR enantiomers after percutaneous application of 3xLD₅₀.

Excerpt	Reference	Relevance
" High bioavailability of HuBChE in blood (>80%) was demonstrated after intramuscular injection."	( The stoichiometry of protection against soman and VX toxicity in monkeys pretreated with human butyrylcholinesterase. Ashani, Y; Cohen, E; Grauer, E; Grunwald, J; Raveh, L, 1997)	0.55
"5% bioavailability relative to iv administration."	( Toxicokinetics of the nerve agent (+/-)-VX in anesthetized and atropinized hairless guinea pigs and marmosets after intravenous and percutaneous administration. Benschop, HP; Lander, BJ; Langenberg, JP; van der Schans, MJ; van der Wiel, H, 2003)	0.59
" The amount of radioactivity in each sample was measured by liquid scintillation counting, from which the skin absorption rate and dose distribution of VX were calculated."	( In vivo skin absorption and distribution of the nerve agent VX (O-ethyl-S-[2(diisopropylamino)ethyl] methylphosphonothioate) in the domestic white pig. Blohm, KL; Chilcott, RP; Clarkson, ED; Dalton, CH; Davison, CM; Hamilton, MG; Hill, I, 2005)	0.77
" These findings together with the observations that the PEGylated rHuAChE exhibits unaltered biodistribution and high bioavailability present a case for using PEGylated rHuAChE as a very efficacious bioscavenger of OP agents."	( Comparison of polyethylene glycol-conjugated recombinant human acetylcholinesterase and serum human butyrylcholinesterase as bioscavengers of organophosphate compounds. Cohen, O; Kronman, C; Mazor, O; Ordentlich, A; Raveh, L; Shafferman, A, 2006)	0.33
" In vivo in swine, absorption rate constants were practically identical for VX and VR enantiomers after percutaneous application of 3xLD₅₀ underlining relevance of amine group and postulated equilibria shifts between charged, uncharged, open and cyclic form (skin depot)."	( In vitro and in vivo toxicological studies of V nerve agents: molecular and stereoselective aspects. Hill, I; Mikler, J; Müller, S; Reiter, G; Thiermann, H; Weatherby, K; Worek, F, 2015)	0.65

Dosage Studied

Study was designed to deliver aerosolized dilute nerve agents in a dose-response manner to investigate the extent of lethality of nerve agents: soman, sarin, VX and VR.

Excerpt	Relevance	Reference
"Male Sprague-Dawley rats injected with a sublethal sc dosage of 110 micrograms/kg of sarin (isopropyl methylphosphonofluoridate), or 12 micrograms/kg of VX (S-(2-diisopropylaminoethyl) O-ethyl methylphosphonothioate), developed severe toxic signs within 5-15 min after sarin and 20-50 min after VX lasting for 5 to 7 hr."	( Comparison of cholinergic and neuromuscular toxicity following acute exposure to sarin and VX in rat. Dettbarn, WD; Gupta, RC; Patterson, GT, 1991)	0.7
" Subacute dosing for 7 days was done via 14-day osmotic minipumps (OMPs)."	( Effects of subacute pretreatment with carbamate together with acute adjunct pretreatment against nerve agent exposure. Anderson, DR; Harris, LW; Lennox, WJ; Solana, RP, 1991)	0.28
" The QL-treated hens were observed for up to 24 h after dosing for acute toxicologic effects and over a 24 d post-dose period for evaluation of delayed neurotoxicity."	( Neurotoxicity assessment of O-ethyl-O'-(2-diisopropylaminoethyl) methylphosphonite (QL) in hens. Bergmann, J; Olajos, EJ; Wall, H; Weimer, JT, 1986)	0.27
" The insect repellent N,N-diethyl-m-toluamide (DEET) reduced the TSP protection against HD regardless of the order of application on rabbit skin prior to dosing of HD."	( Efficacy of the topical skin protectant in advanced development. Hayes, TL; Liu, DK; Snider, TH; Wannemacher, RW, 1999)	0.3
" Dosing of VX was calculated by the volume of aerosol produced per 200 pulses and diluting the agent accordingly."	( Acute lung injury following inhalation exposure to nerve agent VX in guinea pigs. Gordon, RK; Graham, JR; Nambiar, MP; Rezk, PE; Sciuto, AM; Steele, KE; Wright, BS, 2006)	0.96
" A computer simulation based on combination of AChE kinetic data (inhibition, reactivation, aging) with OP toxicokinetics and oxime pharmacokinetics allows the calculation of AChE activities at different scenarios and may facilitate to define effective oxime concentrations and to optimize oxime dosage in OP poisoning."	( Application of kinetic-based computer modelling to evaluate the efficacy of HI 6 in percutaneous VX poisoning. Aurbek, N; Eyer, P; Szinicz, L; Thiermann, H; Worek, F, 2006)	0.55
" Dose-response curves for VX exposure were generated after applying the fluoride ion reactivation assay to the RBC fraction of serially collected whole blood samples that were taken after whole-body exposures that varied in both duration and concentration."	( Gas chromatography-tandem mass spectrometry analysis of red blood cells from Göttingen minipig following whole-body vapor exposure to VX. Burnett, DC; Byers, CE; Gaviola, BI; Hulet, SW; Jakubowski, EM; McGuire, JM; Thomson, SA, )	0.63
" The dose-response effects of 4-PA alone were also examined."	( Effects of 4-pyridine aldoxime on nerve agent-inhibited acetylcholinesterase activity in guinea pigs. McDonough, JH; Shih, TM; Skovira, JW, 2009)	0.35
" Furthermore, we investigated the therapeutic efficacy of a single dose of atropine, obidoxime and diazepam, administered at appearance of first clinical signs, versus that of repetitive dosing of these drugs on the reappearance of signs."	( Percutaneous exposure to the nerve agent VX: Efficacy of combined atropine, obidoxime and diazepam treatment. Joosen, MJ; van der Schans, MJ; van Helden, HP, 2010)	0.63
" The protective ratio (PR, defined as the median lethal dose [LD(50)] of the treatment group divided by the LD(50) of the untreated positive control animals) was calculated from the probit dose-response curves established for each treatment group and nontreated control animals."	( Efficacy studies of Reactive Skin Decontamination Lotion, M291 Skin Decontamination Kit, 0.5% bleach, 1% soapy water, and Skin Exposure Reduction Paste Against Chemical Warfare Agents, part 1: guinea pigs challenged with VX. Braue, EH; Clarkson, ED; Doxzon, BF; Lumpkin, HL; Smith, KH, 2011)	0.55
" This study was designed to deliver aerosolized dilute nerve agents in a dose-response manner to investigate the extent of lethality of nerve agents: soman, sarin, VX and VR."	( Determination of LCt(50)s in anesthetized rats exposed to aerosolized nerve agents. Collins, JL; Lee, R; Peng, X; Pierre, Z; Sciuto, AM; Witriol, A, 2013)	0.59
" Our laboratories have developed novel substituted phenoxyalkyl pyridinium oximes that lead to reduced ChE inhibition in the brains of rats challenged with a high sublethal dosage of the sarin surrogate, whereas 2-PAM did not, using a paradigm designed to demonstrate brain penetration."	( Novel brain-penetrating oximes for reactivation of cholinesterase inhibited by sarin and VX surrogates. Chambers, HW; Chambers, JE; Meek, EC, 2016)	0.66
" A number of these novel oximes have shown the ability to decrease the level of ChE inhibition in the brains of rats treated with a high sublethal dosage of either a sarin surrogate (nitrophenyl isopropyl methylphosphonate, NIMP) or the VX surrogate NEMP."	( Efficacy of novel phenoxyalkyl pyridinium oximes as brain-penetrating reactivators of cholinesterase inhibited by surrogates of sarin and VX. Chambers, HW; Chambers, JE; Funck, KE; Meek, EC; Pringle, RB; Ross, MK, 2016)	0.82
" Our laboratories have invented and patented a platform of substituted phenoxyalkyl pyridinium oximes that have been tested for efficacy as therapy within the brains of adult male rats which were challenged with a high sublethal dosage of highly relevant surrogates of sarin (nitrophenyl isopropyl methylphosphonate, NIMP) and VX (nitrophenyl ethyl methylphosphonate, NEMP)."	( Neuroprotection From Organophosphate-Induced Damage by Novel Phenoxyalkyl Pyridinium Oximes in Rat Brain. Chambers, HW; Chambers, JE; Meek, EC; Pringle, RB, 2018)	0.65
" These data are important for informing adult and pediatric dosing recommendations for NA-induced seizures."	( Evaluation of first-line anticonvulsants to treat nerve agent-induced seizures and prevent neuropathology in adult and pediatric rats. Ardinger, C; Dunn, E; Haines, K; Lee-Stubbs, R; Matson, L; McCarren, H; McDonough, J; Miller-Smith, S; Whitten, K, 2019)	0.51
" Animals were subsequently dosed with either soman or VX in accordance with a stage-wise adaptive dose design to estimate the modified median lethal dose in treated animals."	( Butyrylcholinesterase, a stereospecific in vivo bioscavenger against nerve agent intoxication. Armstrong, SJ; Cadieux, CL; Capacio, BR; Cerasoli, DM; Hodgins, SM; Kasten, SA; Lee-Stubbs, RB; Lenz, DE; Otto, TC; Reeves, TE, 2020)	0.81
" All dosed subjects completed the study."	( A Phase 1, Randomized, Double-Blind, Placebo-Controlled, Crossover Study to Evaluate the Pharmacodynamic Effects of VX-150, a Highly Selective NaV1.8 Inhibitor, in Healthy Male Adults. de Kam, ML; Groeneveld, GJ; Hijma, HJ; Siebenga, PS, 2021)	0.83
" A battery of pain tests (pressure, electrical stair, [capsaicin-induced] heat, and cold pressor) was administered before dosing and repetitively up to 10 h after dosing, with blood sampling up to 24 h after dosing."	( A Phase 1, Randomized, Double-Blind, Placebo-Controlled, Crossover Study to Evaluate the Pharmacodynamic Effects of VX-150, a Highly Selective NaV1.8 Inhibitor, in Healthy Male Adults. de Kam, ML; Groeneveld, GJ; Hijma, HJ; Siebenga, PS, 2021)	0.83

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Role	Description
EC 3.1.1.7 (acetylcholinesterase) inhibitor	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
neurotoxin	A poison that interferes with the functions of the nervous system.
[role 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]

Class	Description
organic thiophosphate
tertiary amino compound	A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
[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
AID404439	Inhibition of bovine AChE	2008	Journal of medicinal chemistry, Jun-12, Volume: 51, Issue:11	Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.
AID407780	Inhibition of human AChE	2008	Journal of medicinal chemistry, Jun-12, Volume: 51, Issue:11	Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	37 (8.24)	18.7374
1990's	72 (16.04)	18.2507
2000's	117 (26.06)	29.6817
2010's	172 (38.31)	24.3611
2020's	51 (11.36)	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	4 (0.84%)	5.53%
Reviews	22 (4.62%)	6.00%
Case Studies	3 (0.63%)	4.05%
Observational	0 (0.00%)	0.25%
Other	447 (93.91%)	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
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.	2.4	2	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
ammonium hydroxide azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.	3.01	4	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
bis(4-nitrophenyl)phosphate bis(4-nitrophenyl)phosphate: RN given refers to parent cpd	2.03	1	0	aryl phosphate
carbamates [no description available]	2.89	4	0	amino-acid anion
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).	2.44	2	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
choline [no description available]	2.72	3	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.15	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.	2.1	1	0	catechols; dihydroxyphenylacetic acid	human metabolite
diacetyl butane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.	2.71	3	0	alpha-diketone	Escherichia coli metabolite; Saccharomyces cerevisiae metabolite
hydroxylamine amino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.	7.07	1	0	hydroxylamines	algal metabolite; bacterial xenobiotic metabolite; EC 1.1.3.13 (alcohol oxidase) inhibitor; EC 4.2.1.22 (cystathionine beta-synthase) inhibitor; EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor; nitric oxide donor; nucleophilic reagent
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.13	1	0	imidazole
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.	7.42	2	0	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.	2.13	1	0	pyridine alkaloid; pyridinecarboxamide; vitamin B3	anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	2.1	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
hydroxide ion [no description available]	2.76	3	0	oxygen hydride	mouse metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.53	2	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
parathion [no description available]	8.27	6	0	C-nitro compound; organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; avicide; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; mouse metabolite
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	2.52	2	0	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
thiosulfates Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.	2.08	1	0	divalent inorganic anion; sulfur oxide; sulfur oxoanion	human 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.	1.94	1	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
huperzine a huperzine A: RN given refers to 5R-(5alpha,9beta,11E)-isomer; structure given in first source. huperzine A : A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease.	1.99	1	0	quinolone
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	2.1	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) 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.	2.08	1	0	monohydroxypyridine; pyridinethione	ionophore
phenytoin [no description available]	2.25	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
tacrine Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.	2.76	3	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.	3.99	1	1	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
ambenonium ambenonium : A symmetrical oxalamide-based bis-quaternary ammonium ion having ethyl and 2-chlorobenzyl groups attached to the nitrogens.	2.04	1	0	quaternary ammonium ion	EC 3.1.1.8 (cholinesterase) inhibitor
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.	7.13	1	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
biperiden Biperiden: A muscarinic antagonist that has effects in both the central and peripheral nervous systems. It has been used in the treatment of arteriosclerotic, idiopathic, and postencephalitic parkinsonism. It has also been used to alleviate extrapyramidal symptoms induced by phenothiazine derivatives and reserpine.. biperiden : A member of the class of piperidines that is N-propylpiperidine in which the methyl hydrogens have been replaced by hydroxy, phenyl, and 5-norbornen-2-yl groups. A muscarinic antagonist affecting both the central and peripheral nervous systems, it is used in the treatment of all forms of Parkinson's disease.	1.99	1	0	piperidines; tertiary alcohol; tertiary amino compound	antidote to sarin poisoning; antidyskinesia agent; antiparkinson drug; muscarinic antagonist; parasympatholytic
chlorpyrifos Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.	2.72	3	0	chloropyridine; organic thiophosphate	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; environmental contaminant; insecticide; xenobiotic
decamethonium decamethonium: RN given refers to parent cpd. decamethonium : A quaternary ammonium ion that is a depolarising muscle relaxant whose structure comprises a decane-1,10-diamine core in which each amino group carries three methyl substituents.	2.04	1	0	quaternary ammonium ion	muscle relaxant; nicotinic acetylcholine receptor agonist
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	3.41	7	0	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
dichlorvos Dichlorvos: An organophosphorus insecticide that inhibits ACETYLCHOLINESTERASE.. dichlorvos : An alkenyl phosphate that is the 2,2-dichloroethenyl ester of dimethyl phosphate.	2	1	0	alkenyl phosphate; dialkyl phosphate; organochlorine acaricide; organophosphate insecticide	anthelminthic drug; antibacterial agent; antifungal agent; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor
disulfoton Disulfoton: An organothiophosphate insecticide.. disulfoton : An organic thiophosphate that is the diethyl ester of S-[2-(ethylsulfanyl)ethyl] dihydrogen phosphorodithioate.	2.03	1	0	organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
edrophonium Edrophonium: A rapid-onset, short-acting cholinesterase inhibitor used in cardiac arrhythmias and in the diagnosis of myasthenia gravis. It has also been used as an antidote to curare principles.. edrophonium : A quaternary ammonium ion that is N-ethyl-N,N-dimethylanilinium in which one of the meta positions is substituted by a hydroxy group. It is a reversible inhibitor of cholinesterase, with a rapid onset (30-60 seconds after injection) but a short duration of action (5-15 minutes). The chloride salt is used in myasthenia gravis both diagnostically and to distinguish between under- or over-treatment with other anticholinesterases. It has also been used for the reversal of neuromuscular blockade in anaesthesia, and for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals.	1.96	1	0	phenols; quaternary ammonium ion	antidote; diagnostic agent; EC 3.1.1.8 (cholinesterase) inhibitor
gallamine triethiodide [no description available]	2.04	1	0	aromatic ether
malathion Malathion: A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes.. malathion : A racemate comprising equimolar amounts of (R) and (S)-malathion. It is a broad spectrum organophosphate proinsecticide used to control a wide range of pests including Coleoptera, Diptera, fruit flies, mosquitos and spider mites.. diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate : A diester that is diethyl succinate in which position 2 is substituted by a (dimethoxyphosphorothioyl)thio group.	7.42	2	0	diester; ethyl ester; organic thiophosphate
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	2.11	1	0	nitrogen mustard; organochlorine compound	alkylating agent
memantine [no description available]	6.98	1	0	adamantanes; primary aliphatic amine	antidepressant; antiparkinson drug; dopaminergic agent; neuroprotective agent; NMDA receptor antagonist
methamidophos methamidophos: structure. methamidophos : An organic thiophosphate resulting from the N-deacylation of the proinsecticide acephate.	2.44	2	0	organic thiophosphate; organothiophosphate insecticide; phosphoramide	acaricide; agrochemical; avicide
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.	2.75	3	0	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative
deet N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.	2	1	0	benzamides; monocarboxylic acid amide	environmental contaminant; insect repellent; xenobiotic
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.	2.38	2	0	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
oxotremorine Oxotremorine: A non-hydrolyzed muscarinic agonist used as a research tool.	2.95	4	0	N-alkylpyrrolidine
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
piracetam Piracetam: A compound suggested to be both a nootropic and a neuroprotective agent.	2.11	1	0	organonitrogen compound; organooxygen compound
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.97	1	0	diarylmethane
procyclidine Procyclidine: A muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism.. procyclidine : A tertiary alcohol that consists of propan-1-ol substituted by a cyclohexyl and a phenyl group at position 1 and a pyrrolidin-1-yl group at position 3.	3.6	2	0	pyrrolidines; tertiary alcohol	antidyskinesia agent; antiparkinson drug; muscarinic antagonist
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.	1.97	1	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.	2.25	1	0	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative
spiperone Spiperone: A spiro butyrophenone analog similar to HALOPERIDOL and other related compounds. It has been recommended in the treatment of SCHIZOPHRENIA.. spiperone : An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.	1.97	1	0	aromatic ketone; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	alpha-adrenergic antagonist; antipsychotic agent; dopaminergic antagonist; psychotropic drug; serotonergic antagonist
succinylcholine Succinylcholine: A quaternary skeletal muscle relaxant usually used in the form of its bromide, chloride, or iodide. It is a depolarizing relaxant, acting in about 30 seconds and with a duration of effect averaging three to five minutes. Succinylcholine is used in surgical, anesthetic, and other procedures in which a brief period of muscle relaxation is called for.. succinylcholine : A quaternary ammonium ion that is the bis-choline ester of succinic acid.	2.46	2	0	quaternary ammonium ion; succinate ester	drug allergen; muscle relaxant; neuromuscular agent
m-(n,n,n-trimethylammonio)trifluoroacetophenone m-(N,N,N-trimethylammonio)trifluoroacetophenone: structure in first source	2.04	1	0
tolazoline Tolazoline: A vasodilator that apparently has direct actions on blood vessels and also increases cardiac output. Tolazoline can interact to some degree with histamine, adrenergic, and cholinergic receptors, but the mechanisms of its therapeutic effects are not clear. It is used in treatment of persistent pulmonary hypertension of the newborn.. tolazoline : A member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group.	1.99	1	0	imidazoles	alpha-adrenergic antagonist; antihypertensive agent; vasodilator agent
trihexyphenidyl Trihexyphenidyl: One of the centrally acting MUSCARINIC ANTAGONISTS used for treatment of PARKINSONIAN DISORDERS and drug-induced extrapyramidal movement disorders and as an antispasmodic.	2.67	3	0	amine
donepezil hydrochloride donepezil hydrochloride : A racemate comprising equimolar amounts of (R)- and (S)- donepezil hydrochloride. Its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.	2.04	1	0
corticosterone [no description available]	2.04	1	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.	2.04	1	0	2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine	antithyroid drug; human metabolite; mouse metabolite; thyroid hormone
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.97	1	0	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
isoflurophate Isoflurophate: A di-isopropyl-fluorophosphate which is an irreversible cholinesterase inhibitor used to investigate the NERVOUS SYSTEM.	4.01	14	0	dialkyl phosphate
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.	2.74	3	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
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.	2.02	1	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.	7.59	2	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
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	8.48	8	0	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	6.98	1	0	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
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.	2.21	1	0	monohydroxyquinoline; quinolone	bacterial xenobiotic 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.	3.65	8	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
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.	2.02	1	0	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
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.	2.48	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
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.07	1	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
ethanethiol ethanethiol: RN given refers to parent cpd; structure. ethanethiol : An alkanethiol that is ethane substituted by a thiol group at position 1. It is added to odorless gaseous products such as liquefied petroleum gas (LPG) to provide a garlic scent which helps warn of gas leaks.	2.02	1	0	alkanethiol	rodenticide
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.41	2	0	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
tabun tabun: proposed as military nerve gas and exptl cholinesterase inhibitor; extremely poisonous; structure	8.11	46	0
tri-o-cresyl phosphate tri-o-cresyl phosphate: see also related IMOL S-140	2.37	2	0
soman Soman: An organophosphorus compound that inhibits cholinesterase. It causes seizures and has been used as a chemical warfare agent.	8.62	98	0	phosphonic ester
quinuclidines Quinuclidines: A class of organic compounds which contain two rings that share a pair of bridgehead carbon atoms and contains an amine group.	1.96	1	0	quinuclidines; saturated organic heterobicyclic parent
pyridostigmine bromide Pyridostigmine Bromide: A cholinesterase inhibitor with a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.	5.32	10	0	pyridinium salt
triethanolamine triethanolamine: RN given refers to parent cpd. triethanolamine : A tertiary amino compound that is ammonia in which each of the hydrogens is substituted by a 2-hydroxyethyl group.	1.98	1	0	amino alcohol; tertiary amino compound; triol	buffer; surfactant
sarin Sarin: An organophosphorus ester compound that produces potent and irreversible inhibition of cholinesterase. It is toxic to the nervous system and is a chemical warfare agent.. isopropyl methylphosphonofluoridate : A phosphinic ester that is the isopropyl ester of methylphosphonofluoridic acid.. sarin : A racemate composed of equal amounts of (R)- and (S)-sarin. A potent and irreversible inhibitor of acetylcholinesterase that is toxic to the nervous system and is employed as a chemical warfare agent.	9.56	128	0	fluorine molecular entity; phosphinic ester
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.02	1	0	alkane
diisopropylamine diisopropylamine: structure given in first source	2.1	1	0
obidoxime chloride Obidoxime Chloride: Cholinesterase reactivator occurring in two interchangeable isomeric forms, syn and anti.	10.23	15	0
triethylamine [no description available]	2.06	1	0	tertiary amine
thiazoles [no description available]	2.11	1	0	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrazines Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.	3.01	1	0	diazine; pyrazines	Daphnia magna metabolite
benactyzine Benactyzine: A centrally acting muscarinic antagonist. Benactyzine has been used in the treatment of depression and is used in research to investigate the role of cholinergic systems on behavior.	2.44	2	0	diarylmethane
edrophonium bromide [no description available]	2.04	1	0
paraoxon [no description available]	4.22	17	0	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	7.45	2	0	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
benzenaminium, 4,4'-(3-oxo-1,5-pentanediyl)bis(n,n-dimethyl-n-2-propenyl-), dibromide Benzenaminium, 4,4'-(3-oxo-1,5-pentanediyl)bis(N,N-dimethyl-N-2-propenyl-), Dibromide: Proposed cholinesterase inhibitor.	2.04	1	0
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.	3.66	2	0	monofluorobenzenes	NMR chemical shift reference compound
cis methyldioxolane [no description available]	1.97	1	0
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.	2.13	1	0
mustard gas Mustard Gas: Severe irritant and vesicant of skin, eyes, and lungs. It may cause blindness and lethal lung edema and was formerly used as a war gas. The substance has been proposed as a cytostatic and for treatment of psoriasis. It has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP-85-002, 1985) (Merck, 11th ed).. bis(2-chloroethyl) sulfide : An ethyl sulfide that is diethyl sulfide in which a hydrogen from each of the terminal methyl groups is replaced by a chlorine. It is a powerful vesicant regulated under the Chemical Weapons Convention.	6.24	25	0	ethyl sulfide; organochlorine compound	alkylating agent; carcinogenic agent; vesicant
echothiophate iodide Echothiophate Iodide: A potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma.. ecothiopate iodide : The iodide salt of ecothiopate. An irreversible acetylcholinesterase inhibitor, it is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate.	2.92	4	0	iodide salt; quaternary ammonium salt	antiglaucoma drug; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
eosine yellowish-(ys) Eosine Yellowish-(YS): A versatile red dye used in cosmetics, pharmaceuticals, textiles, etc., and as tissue stain, vital stain, and counterstain with HEMATOXYLIN. It is also used in special culture media.. eosin YS dye : An organic sodium salt that is 2',4',5',7'-tetrabromofluorescein in which the carboxy group and the phenolic hydroxy group have been deprotonated and the resulting charge is neutralised by two sodium ions.	2.03	1	0	organic sodium salt; organobromine compound	fluorochrome; histological dye
pinacolyl methylphosphonic acid pinacolyl methylphosphonic acid: structure in first source	2.1	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.	2.03	1	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
dimethyl methylphosphonate [no description available]	2.05	1	0
demeton-s-methyl [no description available]	7.95	4	0	organic thiophosphate; organothiophosphate insecticide	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
methylphosphonic acid methylphosphonic acid : A one-carbon compound that is phosphonic acid in which the hydrogen attached to the phosphorus is substituted by a methyl group.	2.41	2	0	one-carbon compound; phosphonic acids
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2.41	1	0	alkali metal hydroxide
isopropyl methylphosphonic acid [no description available]	2.1	1	0
phenylphosphonothioic acid, 2-ethyl 2-(4-nitrophenyl) ester Phenylphosphonothioic Acid, 2-Ethyl 2-(4-Nitrophenyl) Ester: An organothiophosphorus cholinesterase inhibitor that is used as an insecticide and as a acaricide.	2	1	0	organic phosphonate; organothiophosphate insecticide; phosphonic ester	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
benzoylcholine Benzoylcholine: The benzoic acid ester of choline.	2	1	0	benzoate ester
acetylthiocholine Acetylthiocholine: An agent used as a substrate in assays for cholinesterases, especially to discriminate among enzyme types.	1.97	1	0
butyrylthiocholine Butyrylthiocholine: A sulfur-containing analog of butyrylcholine which is hydrolyzed by butyrylcholinesterase to butyrate and thiocholine. It is used as a reagent in the determination of butyrylcholinesterase activity.. butyrylthiocholine : A quaternary ammonium ion obtained by the formal condensation of the carboxy group of butyric acid with the thiol group of thiocholine. It is used as a reagent for determination of butyrylcholinesterase activity.	2.39	2	0	quaternary ammonium ion
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.	1.99	1	0	elemental mercury; zinc group element atom	neurotoxin
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.	2.46	2	0	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.05	1	0	chromium group element atom	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.	2.1	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.	2.03	1	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.	2.1	1	0	copper group element atom; elemental gold
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.11	1	0	titanium group element atom
hypochlorous acid Hypochlorous Acid: An oxyacid of chlorine (HClO) containing monovalent chlorine that acts as an oxidizing or reducing agent.. hypochlorous acid : A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.	2.31	1	0	chlorine oxoacid; reactive oxygen species	EC 2.5.1.18 (glutathione transferase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; human metabolite
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	3.01	1	0	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
chlorine Chlorine: An element with atomic symbol Cl, atomic number 17, and atomic weight 35, and member of the halogen family.	2.17	1	0	diatomic chlorine; gas molecular entity	bleaching agent
methyl demeton methyl mercaptophos: was MH 1972-91 (see under INSECTICIDES, ORGANOTHIOPHOSPHATE (1975-90, Prov 1972-74))	2.03	1	0
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	3.4	1	1	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
ammonium fluoride ammonium fluoride : A fluoride salt having ammonium (NH4+) as the counterion.	7.48	2	0	ammonium salt; fluoride salt
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.	2.46	2	0	titanium oxides	food colouring
fluorides [no description available]	8.32	6	0	halide anion; monoatomic fluorine
fenamiphos [no description available]	2.03	1	0	organophosphate insecticide; organophosphate nematicide; phosphoramidate ester	acaricide; agrochemical; EC 3.1.1.7 (acetylcholinesterase) inhibitor
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.	3.12	5	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	1.97	1	0	pseudohalide anion	mitochondrial respiratory-chain 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.	2.03	1	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
fosphenytoin fosphenytoin: structure given in first & second source	2.25	1	0	imidazolidine-2,4-dione
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.	3.01	1	0	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
irinotecan [no description available]	3.38	2	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
adenosine quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit	2.01	1	0	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent
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.	1.97	1	0
cyclohexyl methylphosphonofluoridate cyclohexyl methylphosphonofluoridate: acetylcholinesterase inhibitor	4.51	22	0
1,7-phenanthroline [no description available]	2.1	1	0	phenanthroline
delphinidin Paraffin: A mixture of solid hydrocarbons obtained from petroleum. It has a wide range of uses including as a stiffening agent in ointments, as a lubricant, and as a topical anti-inflammatory. It is also commonly used as an embedding material in histology.. delphinidin chloride : An anthocyanidin chloride that has delphinidin as the cationic counterpart.	2.1	1	0	anthocyanidin chloride
fluorodeoxyglucose f18 Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)	2.08	1	0	2-deoxy-2-((18)F)fluoro-D-glucose; 2-deoxy-2-fluoro-aldehydo-D-glucose
n-methylscopolamine N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.	2.7	3	0
pro-diazepam pro-diazepam: diazepam prodrug	2.17	1	0	peptide
pentafluorobenzyl bromide pentafluorobenzyl bromide : A member of the class benzyl bromides that is benzyl bromide in which the hydrogens at positions 2, 3, 4, 5 and 6 of the phenyl ring are replaced by fluoro groups. It is a versatile derivatization agent in chromatography and mass spectrometry.	3.66	2	0	benzyl bromides; fluorobenzenes
rivastigmine [no description available]	2.04	1	0	carbamate ester; tertiary amino compound	cholinergic drug; EC 3.1.1.8 (cholinesterase) inhibitor; neuroprotective agent
trimethyl(4-oxopentyl)ammonium trimethyl(4-oxopentyl)ammonium: RN given refers to parent cpd; acetylcholine antag. N,N,N-trimethyl-N-(4-oxopentyl)ammonium : A quaternary ammonium ion in which the substituents on nitrogen are methyl (three) and 4-oxopentyl.	2.04	1	0	quaternary ammonium ion
goethite [no description available]	2.02	1	0
o-ethyl s-(2-dimethylaminoethyl) methylphosphonothioate O-ethyl S-(2-dimethylaminoethyl) methylphosphonothioate: RN given refers to parent cpd; structure	1.97	1	0
propidium iodide [no description available]	2.04	1	0	organic iodide salt
2-(2-cresyl)-4h-1-3-2-benzodioxaphosphorin-2-oxide 2-(2-cresyl)-4H-1-3-2-benzodioxaphosphorin-2-oxide: cyclic metabolite of tri-o-cresyl phosphate; synergist for cholinesterase inhibitors	2.03	1	0
7-methoxytacrine [no description available]	7.21	1	0
tenax tenax: porous polymer based on 2,6-diphenyl-p-phenylene oxide; used for trapping volatile organic compounds	2.11	1	0
azaprophen azaprophen: RN & structure given in first source; RN given refers to parent cpd	1.98	1	0
sodium percarbonate sodium percarbonate: RN given refers to unspecified Na salt	7.6	1	0
2-nitrophenyl octyl ether [no description available]	2.11	1	0
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.	6.58	37	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.76	10	0	divalent inorganic anion; phosphite ion
methylphosphonothiolate [no description available]	7	1	0	organothiophosphorus compound
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.	1.97	1	0	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.4	2	0	cyclodextrin
alpha-cyclodextrin alpha-cyclodextrin : A cycloamylose composed of six alpha-(1->4) linked D-glucopyranose units.	1.97	1	0	cyclodextrin
ethyl methylphosphonic acid ethyl methylphosphonic acid: urinary sarin metabolite	3.01	4	0
potassium fluoride potassium fluoride : A fluoride salt having K+ as the counterion.	2.05	1	0	fluoride salt; potassium salt	NMR chemical shift reference compound; poison
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	2.57	2	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
methylatropine methylatropine: RN given refers to endo-(+-)-isomer; structure in Negwer, 5th ed, #3766	2.03	1	0
n(6)-cyclopentyladenosine [no description available]	2.01	1	0
sesquiterpenes [no description available]	1.99	1	0
benztropine Benztropine: A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.. benzatropine : Tropane in which a hydrogen at position 3 is substituted by a diphenylmethoxy group (endo-isomer). An acetylcholine receptor antagonist, it is used (particularly as its methanesulphonate salt) in the treatment of Parkinson's disease, and to reduce parkinsonism and akathisia side effects of antipsychotic treatments.	1.97	1	0	diarylmethane
ferric ferrocyanide ferric ferrocyanide: antidote to thallium poisoning; RN given refers to Fe(+3)[3:4] salt; structure	2.03	1	0
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	7.31	1	0	alkali metal atom
4-aminophenylphosphonic acid methyl-1,2,2-trimethylpropyl diester [no description available]	1.97	1	0
chloramine-t chloramine-T: RN given refers to unlabeled parent cpd. chloramine T : An organic sodium salt derivative of toluene-4-sulfonamide with a chloro substituent in place of an amino hydrogen.	7.41	1	0	organic sodium salt	allergen; antifouling biocide; disinfectant
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.	2.03	1	0
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.	2.07	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.	2.07	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
zeaxanthin Zeaxanthins: Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA.	2.6	1	0	carotenol	antioxidant; bacterial metabolite; cofactor
hydrocodone Hydrocodone: Narcotic analgesic related to CODEINE, but more potent and more addicting by weight. It is used also as cough suppressant.. hydrocodone : A morphinane-like compound that is a semi-synthetic opioid synthesized from codeine.	3.99	1	1	morphinane-like compound; organic heteropentacyclic compound	antitussive; mu-opioid receptor agonist; opioid analgesic
levetiracetam Levetiracetam: A pyrrolidinone and acetamide derivative that is used primarily for the treatment of SEIZURES and some movement disorders, and as a nootropic agent.. levetiracetam : A pyrrolidinone and carboxamide that is N-methylpyrrolidin-2-one in which one of the methyl hydrogens is replaced by an aminocarbonyl group, while another is replaced by an ethyl group (the S enantiomer). An anticonvulsant, it is used for the treatment of epilepsy in both human and veterinary medicine.	2.57	2	0	pyrrolidin-2-ones	anticonvulsant; environmental contaminant; xenobiotic
gamma-cyclodextrin gamma-cyclodextrin : A cycloamylose composed of eight alpha-(1->4) linked D-glucopyranose units.	1.97	1	0	cyclodextrin
acetaldehyde oxime acetaldehyde oxime: structure. (E)-acetaldehyde oxime : The (E)-stereoisomer of acetaldehyde oxime.. acetaldehyde oxime : An aldoxime derived from acetaldehyde.	2.25	1	0	acetaldehyde oxime
mevinphos Mevinphos: An organophosphate cholinesterase inhibitor that is used as an insecticide.	1.99	1	0
aluminum Aluminum: A metallic element that has the atomic number 13, atomic symbol Al, and atomic weight 26.98.	2.13	1	0	boron group element atom; elemental aluminium; metal atom
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	3.11	1	0	metalloid atom; pnictogen	micronutrient
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.53	2	0	chalcogen; nonmetal atom	macronutrient
lewisite lewisite: RN given refers to cpd without isomeric designation	3.11	1	0
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	3.04	4	0	cysteinium	fundamental metabolite
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.	2.77	3	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient
huperzine b huperzine B: Chinese drug isolated from Huperzia serrata; structure given in first source; also isolated from Phlegmariurus fordii	2.04	1	0	phenanthrol
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.68	3	0	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
germanium Germanium: A rare metal element with a blue-gray appearance and atomic symbol Ge, atomic number 32, and atomic weight 72.63.	2.07	1	0	carbon group element atom; metalloid atom; nonmetal atom
clinoptilolite clinoptilolite: clinoptilolite was SY to zeolite (NM); use zeolites (NM) to search through 1993; RN is for cpd with unknown MF	2.4	2	0
diacetylmonoxime diacetylmonoxime: used diagnostically for determining urea in blood; structure; myosin ATPase antagonist. diacetylmonoxime : A ketoxime obtained via formal condensation of butane-2,3-dione with hydroxylamine. It is a reversible myosin ATPase inhibitor.	2.71	3	0
bis(7)-tacrine [no description available]	2.04	1	0	secondary amino compound	apoptosis inhibitor; EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; neuroprotective agent
aldicarb Aldicarb: Carbamate derivative used as an insecticide, acaricide, and nematocide.. aldicarb : The oxime carbamate resulting from the addition of 2-methyl-2-(methylsulfanyl)propanaldoxime to methyl isocyanate. A member of the class of oxime carbamate insecticides, aldicarb is a mixture of E and Z isomers; it is not known which isomer is more active.	2.03	1	0
1-methyl-1,6-dihydropyridine-2-carbaldoxime 1-methyl-1,6-dihydropyridine-2-carbaldoxime: structure	2.06	1	0	dihydropyridine
oxamyl oxamyl: RN given refers to parent cpd; structure	2.03	1	0
ganstigmine ganstigmine: structure in first source	2.04	1	0
zeolites [no description available]	2.68	3	0
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.05	1	0
vx 765 belnacasan: a NSAID	2.6	1	0	dipeptide
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	1.98	1	0
scopolamine hydrobromide [no description available]	4.25	5	0
cobrotoxin Cobra Neurotoxin Proteins: Toxins, contained in cobra (Naja) venom that block cholinergic receptors; two specific proteins have been described, the small (short, Type I) and the large (long, Type II) which also exist in other Elapid venoms.	1.96	1	0
vx-770 ivacaftor: a CFTR potentiator; structure in first source. ivacaftor : An aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis.	3.82	2	0	aromatic amide; monocarboxylic acid amide; phenols; quinolone	CFTR potentiator; orphan drug
lumacaftor lumacaftor: a corrector of CF transmembrane conductance regulator (CTFR); structure in first source. lumacaftor : An aromatic amide obtained by formal condensation of the carboxy group of 1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid with the aromatic amino group of 3-(6-amino-3-methylpyridin-2-yl)benzoic acid. Used for the treatment of cystic fibrosis.	3.7	1	0	aromatic amide; benzodioxoles; benzoic acids; cyclopropanes; organofluorine compound; pyridines	CFTR potentiator; orphan drug
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2.5	2	0	inorganic sodium salt	bleaching agent; disinfectant
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene [no description available]	2.1	1	0	BODIPY compound
ve 821 3-amino-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide: an antineoplastic agent; structure in first source	3.01	1	0	aromatic amide
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	2.6	1	0
clay Clay: A naturally-occurring rock or soil constituent characterized by particles with a diameter of less than 0.005 mm. It is composed primarily of hydrous aluminum silicates, trace amounts of metal OXIDES, and organic matter.	1.98	1	0
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.78	3	0
t-2 toxin T-2 Toxin: A potent mycotoxin produced in feedstuffs by several species of the genus FUSARIUM. It elicits a severe inflammatory reaction in animals and has teratogenic effects.. T-2 toxin : A trichothecene mycotoxin produced by fungi of the genus Fusarium. It is a common contaminant in food and feedstuffs of cereal origin and is known to cause a range of toxic effects in humans and animals.	2	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.	2.07	1	0
pralidoxime pralidoxime: RN given refers to parent cpd; chloride was minor descriptor (75-80); on-line & Index Medicus search PRALIDOXIME COMPOUNDS (66-80). pralidoxime : A pyridinium ion that is 1-methylpyridinium substituted by a (hydroxyimino)methyl group at position 2.	11.39	21	0	pyridinium ion	antidote to organophosphate poisoning; antidote to sarin poisoning; cholinergic drug; cholinesterase reactivator
hlo 7 HLo 7: structure given in first source	7.94	4	0	organic molecular entity
asoxime chloride [no description available]	4.56	24	0
pyridine-4-aldoxime pyridine-4-aldoxime: RN given for cpd without isomeric designation	2.5	2	0
n,n'-monomethylenebis(pyridiniumaldoxime) N,N'-monomethylenebis(pyridiniumaldoxime): RN given refers to parent cpd	2.47	2	0
hs 6 HS 6: structure	2.41	2	0
trimedoxime bromide Trimedoxime: Cholinesterase reactivator used as an antidote in alkyl phosphate poisoning.	4.25	5	0
obidoxime chloride [no description available]	2.04	1	0

Condition	Relationship Strength	Studies	Trials
Ache [description not available]	3.8	1	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	3.8	1	1
Hepatocellular Carcinoma [description not available]	2.6	1	0
Cancer of Liver [description not available]	2.6	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.	2.6	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.6	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.6	1	0
Encephalopathy, Toxic [description not available]	4.48	8	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)	2.6	1	0
Mouth Diseases Diseases involving the MOUTH.	2.6	1	0
Xanthoma [description not available]	2.6	1	0
Parakeratosis Persistence of the nuclei of the keratinocytes into the stratum corneum of the skin. This is a normal state only in the epithelium of true mucous membranes in the mouth and vagina. (Dorland, 27th ed)	2.6	1	0
Acute Post-operative Pain [description not available]	3.99	1	1
Pain, Postoperative Pain during the period after surgery.	3.99	1	1
Acute Pain Intensely discomforting, distressful, or agonizing sensation associated with trauma or disease, with well-defined location, character, and timing.	3.99	1	1
Cystic Fibrosis of Pancreas [description not available]	3.64	2	0
Breathlessness [description not available]	3.52	1	0
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	3.64	2	0
Dyspnea Difficult or labored breathing.	3.52	1	0
Constricted Pupil [description not available]	2.8	3	0
Miosis Pupillary constriction. This may result from congenital absence of the dilatator pupillary muscle, defective sympathetic innervation, or irritation of the CONJUNCTIVA or CORNEA.	2.8	3	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.	5.06	16	0
Organophosphorus Poisoning [description not available]	6.94	26	0
Organophosphate Poisoning Poisoning due to exposure to ORGANOPHOSPHORUS COMPOUNDS, such as ORGANOPHOSPHATES; ORGANOTHIOPHOSPHATES; and ORGANOTHIOPHOSPHONATES.	6.94	26	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.7	10	0
Absence Status [description not available]	2.63	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)	2.63	2	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	5.5	15	1
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.	2.96	4	0
Left Ventricular Dysfunction [description not available]	2.15	1	0
Arteriosclerosis, Coronary [description not available]	2.15	1	0
Coronary Artery Disease Pathological processes of CORONARY ARTERIES that may derive from a congenital abnormality, atherosclerotic, or non-atherosclerotic cause.	2.15	1	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.	2.15	1	0
Wounds, Penetrating Wounds caused by objects penetrating the skin.	2.17	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.16	5	0
Absence Seizure [description not available]	4.97	14	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.	4.97	14	0
Eye Disorders [description not available]	2.21	1	0
Eye Diseases Diseases affecting the eye.	2.21	1	0
Respiratory Tract Diseases Diseases involving the RESPIRATORY SYSTEM.	2.21	1	0
Nervous System Disorders [description not available]	4.51	5	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.93	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.	4.51	5	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.45	2	0
Experimental Lung Inflammation Inflammation of any part, segment or lobe, of the lung parenchyma.	2.1	1	0
Edema, Pulmonary [description not available]	2.71	3	0
Weight Reduction [description not available]	2.46	2	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.71	3	0
Pneumonia Infection of the lung often accompanied by inflammation.	2.1	1	0
Pulmonary Edema Excessive accumulation of extravascular fluid in the lung, an indication of a serious underlying disease or disorder. Pulmonary edema prevents efficient PULMONARY GAS EXCHANGE in the PULMONARY ALVEOLI, and can be life-threatening.	2.71	3	0
Ulcer A lesion on the surface of the skin or a mucous surface, produced by the sloughing of inflammatory necrotic tissue.	2.1	1	0
Weight Loss Decrease in existing BODY WEIGHT.	2.46	2	0
Injuries Used with anatomic headings, animals, and sports for wounds and injuries. Excludes cell damage, for which pathology is used.	2.52	2	0
Wounds and Injuries Damage inflicted on the body as the direct or indirect result of an external force, with or without disruption of structural continuity.	2.52	2	0
ANS (Autonomic Nervous System) Diseases [description not available]	2.13	1	0
Carcinoma, Epidermoid [description not available]	2.51	2	0
Innate Inflammatory Response [description not available]	2.47	2	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)	2.51	2	0
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.	2.47	2	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.43	2	0
Extravascular Hemolysis [description not available]	2.04	1	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.04	1	0
Palsy [description not available]	2.05	1	0
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	2.05	1	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.44	2	0
Cancer of the Tongue [description not available]	2.08	1	0
Tongue Neoplasms Tumors or cancer of the TONGUE.	2.08	1	0
Gas Poisoning Poisoning that results from exposure to gases such as CARBON MONOXIDE; NOBLE GASES; OXYGEN; or NATURAL GAS.	2.69	3	0
Bone Cancer [description not available]	1.93	1	0
Carcinoma, Anaplastic [description not available]	1.93	1	0
Benign Neoplasms [description not available]	2.34	2	0
Experimental Neoplasms [description not available]	2.34	2	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	1.93	1	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.	6.93	1	0
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.	2.34	2	0
Milk-Alkali Syndrome [description not available]	1.94	1	0
Hypercalcemia Abnormally high level of calcium in the blood.	1.94	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.	1.94	1	0
Chronic Lung Injury [description not available]	2.93	1	0
Disease, Pulmonary [description not available]	3.35	2	0
Lung Diseases Pathological processes involving any part of the LUNG.	3.35	2	0
Bacillus anthracis Infection [description not available]	2.93	1	0
Alastrim [description not available]	2.93	1	0
Anthrax An acute infection caused by the spore-forming bacteria BACILLUS ANTHRACIS. It commonly affects hoofed animals such as sheep and goats. Infection in humans often involves the skin (cutaneous anthrax), the lungs (inhalation anthrax), or the gastrointestinal tract. Anthrax is not contagious and can be treated with antibiotics.	2.93	1	0
Smallpox An acute, highly contagious, often fatal infectious disease caused by an orthopoxvirus characterized by a biphasic febrile course and distinctive progressive skin eruptions. Vaccination has succeeded in eradicating smallpox worldwide. (Dorland, 28th ed)	2.93	1	0
Asthma, Bronchial [description not available]	3.4	1	1
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).	3.4	1	1
Bronchial Hyperreactivity Tendency of the smooth muscle of the tracheobronchial tree to contract more intensely in response to a given stimulus than it does in the response seen in normal individuals. This condition is present in virtually all symptomatic patients with asthma. The most prominent manifestation of this smooth muscle contraction is a decrease in airway caliber that can be readily measured in the pulmonary function laboratory.	3.4	1	1
Apnea A transient absence of spontaneous respiration.	2.02	1	0
Acute Disease Disease having a short and relatively severe course.	2.69	3	0
Adverse Drug Event [description not available]	2.95	1	0
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.95	1	0
Hypothermia, Accidental [description not available]	2.03	1	0
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.03	1	0
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	2.03	1	0
Chronic Illness [description not available]	2.42	2	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.42	2	0
Diseases, Occupational [description not available]	2.4	2	0
Disease Exacerbation [description not available]	2	1	0
Bladder Cancer [description not available]	2	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2	1	0
Carcinoma, Transitional Cell A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.	2	1	0
Action Tremor [description not available]	2	1	0
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	2	1	0
Malignant Melanoma [description not available]	2.01	1	0
Nevi, Melanocytic [description not available]	2.01	1	0
Cancer of Skin [description not available]	2.01	1	0
Lichen Sclerosis [description not available]	2.01	1	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)	2.01	1	0
Nevus, Pigmented A nevus containing melanin. The term is usually restricted to nevocytic nevi (round or oval collections of melanin-containing nevus cells occurring at the dermoepidermal junction of the skin or in the dermis proper) or moles, but may be applied to other pigmented nevi.	2.01	1	0
Skin Neoplasms Tumors or cancer of the SKIN.	2.01	1	0
Lichen Sclerosus et Atrophicus A chronic inflammatory mucocutaneous disease usually affecting the female genitalia (VULVAR LICHEN SCLEROSUS) and BALANITIS XEROTICA OBLITERANS in males. It is also called white spot disease and Csillag's disease.	2.01	1	0
Muscle Disorders [description not available]	1.98	1	0
Muscular Diseases Acquired, familial, and congenital disorders of SKELETAL MUSCLE and SMOOTH MUSCLE.	1.98	1	0
Ovine Diseases [description not available]	1.97	1	0
Acute Hypercapnic Respiratory Failure [description not available]	1.96	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)	1.96	1	0

vx

Description

Cross-References

Synonyms (58)

Research Excerpts

Overview

Actions

Treatment

Toxicity

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (2)

Bioassays (2)

Research

Studies (449)

Market Indicators

Research Demand Index: 87.69

Study Types

vx

Description

Cross-References

Synonyms (58)

Research Excerpts

Overview

Actions

Treatment

Toxicity

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (2)

Bioassays (2)

Research

Studies (449)

Market Indicators

Research Demand Index: 87.69

Study Types

Related Drugs (215)

Related Conditions (117)