Page last updated: 2024-07-31 16:13:07

dezocine

Description

dezocine: potent analgesic; RN given refers to ((5R-(5alpha,11alpha,13S*)))-isomer (dezocin); structure [MeSH]

dezocine : (7S,8S)-7-Amino-8-methyl-5,6,7,8-tetrahydronaphthalen-2-ol in which the hydrogen at position 8 and one of the hydrogens at position 6 are substituted by each end of a tetramethylene bridge. A synthetic opioid analgesic, it has mixed opiod agonist and antagonist properties. Although it is used for pain management, it can produce opioid withdrawal syndrome in patients already dependent on other opioids, and its clinical application is limited by side effects such as dizziness. [CHeBI]

Cross-References

ID Source	ID
PubMed CID	3033053
CHEMBL ID	1685
SCHEMBL ID	3072
CHEBI ID	4474
MeSH ID	M0056650

Synonyms (52)

Synonym
dalgan
wy-16225
dezocina [inn-spanish]
wy-16,225
13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecenol
5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5alpha,11alpha,13s*)-, (-)-
dezocine [usan:inn]
dezocinum [inn-latin]
wy 16225
wy 16,225
dezocine
53648-55-8
C08010
(-)-13beta-amino-5,6,7,8,9,10,11alpha,12-octahydro-5alpha-methyl-5,11-methanobenzocyclodecen-3-ol
DB01209
dezocine (usan)
D00838
dalgan (tn)
CHEBI:4474 ,
(5r,11s,13s)-13-amino-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzocyclodecen-3-ol
dezocinum
dezocina
bdbm50276568
dozocine
CHEMBL1685 ,
docozine
AKOS016014025
unii-vhx8k5sv4x
vhx8k5sv4x ,
dezocine [who-dd]
dezocine [mi]
dezocine [usan]
dezocine [orange book]
dezocine [vandf]
(-)-13.beta.-amino-5,6,7,8,9,10,11.alpha.,12-octahydro-5.alpha.-methyl-5,11-methanobenzocyclodecen-3-ol
dezocine [inn]
5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5.alpha.,11.alpha.,13s*)
dezocine [mart.]
SCHEMBL3072
DTXSID2022911 ,
(1r,9s,15s)-15-amino-1-methyltricyclo[7.5.1.0^{2,7}]pentadeca-2,4,6-trien-4-ol
(1r,9s,15s)-15-amino-1-methyltricyclo[7.5.1.02,7]pentadeca-2(7),3,5-trien-4-ol
Q1109018
EN300-27032797
(1r,9s,15s)-15-amino-1-methyltricyclo[7.5.1.0,2,7]pentadeca-2,4,6-trien-4-ol
dtxcid702911
5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5alpha,11alpha,13s*)
5,11-methanobenzocyclodecen-3-ol, 5,6,7,8,9,10,11,12-octahydro-13-amino-5-methyl-
n02ax03
dezocinum (inn-latin)
dezocina (inn-spanish)
dezocine (mart.)

Roles (1)

Role	Description
opioid analgesic	A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.

Drug Classes (2)

Class	Description
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
primary amino compound	A compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.

Pathways (1)

dezocine is involved in 1 pathway(s), involving a total of 31 unique proteins and 11 unique compounds

Pathway	Proteins	Compounds
Dezocine Action Pathway	31	11

Protein Targets (1)

Activation Measurements

Protein	Taxonomy	Measurement	Average (mM)	Bioassay(s)
Mu-type opioid receptor	Homo sapiens (human)	EC50	0.0380	AID392933

Bioassays (8)

Assay ID	Title	Year	Journal	Article
AID588218	FDA HLAED, lactate dehydrogenase (LDH) increase	2004	Current drug discovery technologies, Dec, Volume: 1, Issue:4 ISSN: 1570-1638	Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588214	FDA HLAED, liver enzyme composite activity	2004	Current drug discovery technologies, Dec, Volume: 1, Issue:4 ISSN: 1570-1638	Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588219	FDA HLAED, gamma-glutamyl transferase (GGT) increase	2004	Current drug discovery technologies, Dec, Volume: 1, Issue:4 ISSN: 1570-1638	Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588215	FDA HLAED, alkaline phosphatase increase	2004	Current drug discovery technologies, Dec, Volume: 1, Issue:4 ISSN: 1570-1638	Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588216	FDA HLAED, serum glutamic oxaloacetic transaminase (SGOT) increase	2004	Current drug discovery technologies, Dec, Volume: 1, Issue:4 ISSN: 1570-1638	Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588217	FDA HLAED, serum glutamic pyruvic transaminase (SGPT) increase	2004	Current drug discovery technologies, Dec, Volume: 1, Issue:4 ISSN: 1570-1638	Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID392934	Intrinsic activity at human cloned mu opioid receptor at 100 uM by [35S]GTPgammaS binding assay relative to DAMGO	2009	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 19, Issue:4 ISSN: 1464-3405	Discovery of mu-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions.
AID392933	Agonist activity at human cloned mu opioid receptor by [35S]GTPgammaS binding assay	2009	Bioorganic & medicinal chemistry letters, Feb-15, Volume: 19, Issue:4 ISSN: 1464-3405	Discovery of mu-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions.

Research

Studies (135)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	29 (21.48)	18.7374
1990's	14 (10.37)	18.2507
2000's	7 (5.19)	29.6817
2010's	42 (31.11)	24.3611
2020's	43 (31.85)	2.80

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	56 (39.44%)	5.53%
Reviews	11 (7.75%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	1 (0.70%)	0.25%
Other	74 (52.11%)	84.16%

Substance	Classes	Roles	Relationship Strength
3-hydroxybenzyl alcohol	hydroxybenzyl alcohol; phenols	metabolite	low
4-hydroxybenzyl alcohol	benzyl alcohols; phenols	plant metabolite	low
4-hydroxyphenylacetic acid	monocarboxylic acid; phenols	fungal metabolite; human metabolite; mouse metabolite; plant metabolite	low
4-hydroxymandelic acid	2-hydroxy carboxylic acid; phenols	metabolite	low
4-vinylguaiacol	phenols	flavouring agent; pheromone; plant metabolite	low
4-hydroxyphenylglyoxylic acid	phenols		low
melilotic acid	monocarboxylic acid; phenols	bacterial xenobiotic metabolite; fungal xenobiotic metabolite; human xenobiotic metabolite; plant metabolite	low
n-acetylserotonin	acetamides; N-acylserotonin; phenols	antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist	low
4-hydroxyphenylpyruvic acid	2-oxo monocarboxylic acid; phenols	human metabolite	low
phenol	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite	low
vanillin	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite	low
8-hydroxy-2-(di-n-propylamino)tetralin	phenols; tertiary amino compound; tetralins	serotonergic antagonist	low
vanilmandelic acid	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite	low
3-hydroxybenzylhydrazine	phenols		low
3-methoxytyramine	monomethoxybenzene; phenols; phenylethylamine; primary amino compound	biomarker; human blood serum metabolite; human urinary metabolite	low
4-hydroxybenzoic acid hydrazide	carbohydrazide; phenols		low
3-hydroxy-4-methoxyphenethylamine	monomethoxybenzene; phenols; phenylethylamine; primary amino compound	human metabolite; rat metabolite	low
4-nonylphenol	phenols	environmental contaminant	low
acetaminophen	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	low
albuterol	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic	low
amodiaquine	aminoquinoline; organochlorine compound; phenols; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; drug allergen; EC 2.1.1.8 (histamine N-methyltransferase) inhibitor; non-steroidal anti-inflammatory drug; prodrug	low
capsaicin	methoxybenzenes; phenols		low
chloroxylenol	monochlorobenzenes; phenols	antiseptic drug; disinfectant; molluscicide	low
nonivamide	capsaicinoid; phenols	lachrymator	low
dienestrol	olefinic compound; phenols	xenoestrogen	low
edrophonium	phenols; quaternary ammonium ion	antidote; diagnostic agent; EC 3.1.1.8 (cholinesterase) inhibitor	low
etilefrine	phenols		low
fluorescite	benzoic acids; cyclic ketone; hydroxy monocarboxylic acid; organic heterotricyclic compound; phenols; xanthene dye	fluorescent dye; radioopaque medium	low
formoterol fumarate	formamides; phenols; phenylethanolamines; secondary alcohol; secondary amino compound		low
labetalol	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound		low
ly 171883	acetophenones; aromatic ether; phenols; tetrazoles	anti-asthmatic drug; leukotriene antagonist	low
mesalamine	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug	low
norfenefrine	phenols		low
ns 1619	(trifluoromethyl)benzenes; benzimidazoles; phenols	potassium channel opener	low
oxymetazoline	carboxamidine; imidazolines; phenols	alpha-adrenergic agonist; nasal decongestant; sympathomimetic agent; vasoconstrictor agent	low
oxyphenbutazone	phenols; pyrazolidines	antimicrobial agent; antineoplastic agent; antipyretic; drug metabolite; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic metabolite	low
aminosalicylic acid	aminobenzoic acid; phenols	antitubercular agent	low
phenolphthalein	phenols		low
phenolsulfonphthalein	2,1-benzoxathiole; arenesulfonate ester; phenols; sultone	acid-base indicator; diagnostic agent; two-colour indicator	low
Phenyliodoundecynoate	benzoate ester; phenols		low
propofol	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative	low
psilocin	hydroxyindoles; phenols; tertiary amino compound; tryptamine alkaloid	drug metabolite; fungal metabolite; hallucinogen; human xenobiotic metabolite; serotonergic agonist	low
raloxifene	1-benzothiophenes; aromatic ketone; N-oxyethylpiperidine; phenols	bone density conservation agent; estrogen antagonist; estrogen receptor modulator	low
resorcinol monoacetate	phenols; phenyl acetates	antibacterial agent; dermatologic drug	low
salicylamide	phenols; salicylamides	antirheumatic drug; non-narcotic analgesic	low
salmeterol xinafoate	ether; phenols; primary alcohol; secondary alcohol; secondary amino compound		low
salicylsalicylic acid	benzoate ester; benzoic acids; phenols; salicylates	antineoplastic agent; antirheumatic drug; EC 3.5.2.6 (beta-lactamase) inhibitor; hypoglycemic agent; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug	low
sb 202190	imidazoles; organofluorine compound; phenols; pyridines	apoptosis inducer; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor	low
sulfobromophthalein	2-benzofurans; organobromine compound; organosulfonic acid; phenols	dye	low
triclosan	aromatic ether; dichlorobenzene; monochlorobenzenes; phenols	antibacterial agent; antimalarial; drug allergen; EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; fungicide; persistent organic pollutant; xenobiotic	low
phentolamine	imidazoles; phenols; substituted aniline; tertiary amino compound	alpha-adrenergic antagonist; vasodilator agent	low
estrone	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite	low
17-desoxyestradiol	3-hydroxy steroid; phenolic steroid; phenols	estrogen	low
n-methyl-4-aminophenol	phenols	allergen	low
phenylephrine	phenols; phenylethanolamines; secondary amino compound	alpha-adrenergic agonist; cardiotonic drug; mydriatic agent; nasal decongestant; protective agent; sympathomimetic agent; vasoconstrictor agent	low
isoamyl salicylate	benzoate ester; phenols		low
glycol salicylate	phenols; primary alcohol; salicylates		low
2-tert-butyl-4-hydroxyanisole	aromatic ether; phenols		low
2-isopropylphenol	phenols		low
2-sec-butylphenol	phenols		low
thymol	monoterpenoid; phenols	volatile oil component	low
2-ethylphenol	phenols		low
pyrogallol 1,3-dimethyl ether	dimethoxybenzene; phenols	plant metabolite	low
acetyleugenol	benzoate ester; phenols		low
creosol	methoxybenzenes; phenols		low
synephrine	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite	low
propylparaben	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent	low
3,4-dimethylphenol	phenols		low
2,5-xylenol	phenols	animal metabolite; volatile oil component	low
2,4-di-tert-butylphenol	alkylbenzene; phenols	antioxidant; bacterial metabolite; marine metabolite	low
sulfosalicylic acid	arenesulfonic acid; benzoic acids; phenols	metabolite	low
butylphen	phenols	allergen	low
4-isopropylphenol	phenols	flavouring agent	low
2,4-dimethylphenol	aromatic fungicide; phenols	disinfectant; volatile oil component	low
3,5-xylenol	phenols	xenobiotic metabolite	low
oxyphenisatin acetate	benzoate ester; phenols		low
bromphenol blue	2,1-benzoxathiole; arenesulfonate ester; organobromine compound; phenols; sultone	acid-base indicator; dye; two-colour indicator	low
phenyl salicylate	benzoate ester; phenols; salicylates	ultraviolet filter	low
homosalate	benzoate ester; phenols		low
benzyl salicylate	benzoate ester; phenols		low
2-ethylhexyl salicylate	benzoate ester; phenols		low
2'-hydroxyacetophenone	monohydroxyacetophenone; phenols	flavouring agent	low
3-tert-butyl-4-hydroxyanisole	aromatic ether; phenols	antioxidant; human xenobiotic metabolite	low
ethyl vanillin	aromatic ether; benzaldehydes; phenols	antioxidant; flavouring agent	low
p-cresyl acetate	benzoate ester; phenols		low
3-hydroxyanisole	monomethoxybenzene; phenols		low
mequinol	methoxybenzenes; phenols	metabolite	low
ethamivan	methoxybenzenes; phenols		low
4-hydroxyphenyllactic acid	2-hydroxy carboxylic acid; phenols	bacterial metabolite; human metabolite	low
plumbagin	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite	low
topanol 354	methoxybenzenes; phenols		low
carvacrol	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component	low
phloroglucinol dimethyl ether	methoxybenzenes; phenols		low
4-hydroxyphenylethanol	phenols	anti-arrhythmia drug; antioxidant; cardiovascular drug; fungal metabolite; geroprotector; plant metabolite; protective agent	low
syringic acid	benzoic acids; dimethoxybenzene; phenols	plant metabolite	low
methoxyhydroxyphenylglycol	methoxybenzenes; phenols		low
paeonol	methoxybenzenes; phenols	metabolite	low
2-hydroxyphenylacetic acid	hydroxy monocarboxylic acid; phenols	human metabolite; mouse metabolite	low
2-hydroxyacetanilide	acetamides; phenols	anti-inflammatory agent; antineoplastic agent; antirheumatic drug; apoptosis inducer; platelet aggregation inhibitor; xenobiotic metabolite	low
3-ethylphenol	phenols		low
3-hydroxybenzeneacetic acid	monocarboxylic acid; phenols	human xenobiotic metabolite	low
3-hydroxyacetanilide	acetamides; phenols	non-narcotic analgesic	low
isovanillin	benzaldehydes; monomethoxybenzene; phenols	animal metabolite; antidiarrhoeal drug; antifungal agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; HIV protease inhibitor; plant metabolite	low
4-Ethoxyphenol	aromatic ether; phenols		low
bulbocapnine	aporphine alkaloid; aromatic ether; oxacycle; phenols	EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor; EC 1.4.3.22 (diamine oxidase) inhibitor; plant metabolite	low
2-propylphenol	phenols	flavouring agent; plant metabolite	low
4-cyanophenol	phenols	EC 1.4.3.4 (monoamine oxidase) inhibitor	low
2-(2'-hydroxyphenyl)benzoxazole	1,3-benzoxazoles; phenols	geroprotector	low
ethyl n-alpha-acetyl-tyrosinate	acetamides; ethyl ester; L-tyrosine derivative; phenols		low
fenadiazole	1,3,4-oxadiazoles; biaryl; phenols	sedative	low
amylmetacresol	phenols	antiseptic drug	low
4-chloro-2-cresol	monochlorobenzenes; phenols		low
antimycin a	benzamides; formamides; macrodiolide; phenols	antifungal agent; mitochondrial respiratory-chain inhibitor; piscicide	low
isobarbaloin	anthracenes; C-glycosyl compound; cyclic ketone; phenols	laxative; metabolite	low
dinoterb	C-nitro compound; phenols		low
4-n-Butylphenol	phenols		low
bromoxynil	dibromobenzene; hydroxynitrile; phenols	environmental contaminant; herbicide; xenobiotic	low
2-allylphenol	phenols	antifungal agrochemical	low
4-octylphenol	phenols	metabolite; surfactant; xenoestrogen	low
3-methoxy-4-hydroxyphenylethanol	methoxybenzenes; phenols		low
acetosyringone	acetophenones; dimethoxybenzene; phenols	anti-asthmatic drug; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug; plant metabolite	low
bis(4-oxyphenyl)sulfide	phenols		low
hydroxyphenytoin	imidazolidine-2,4-dione; phenols	metabolite	low
2-(2-hydroxyphenyl)benzothiazole	benzothiazoles; phenols	geroprotector	low
cue-lure	benzoate ester; phenols		low
methyl vanillate	aromatic ether; benzoate ester; phenols	antioxidant; plant metabolite	low
2-isopropoxyphenol	aromatic ether; phenols		low
raspberry ketone	methyl ketone; phenols	androgen antagonist; cosmetic; flavouring agent; fragrance; hepatoprotective agent; metabolite	low
laurolitsine	aporphine alkaloid; aromatic ether; phenols	HIV-1 integrase inhibitor; metabolite	low
4-n-Pentylphenol	phenols		low
zingerone	methyl ketone; monomethoxybenzene; phenols	anti-inflammatory agent; antiemetic; antioxidant; flavouring agent; fragrance; plant metabolite; radiation protective agent	low
4-ethylphenol	phenols	fungal xenobiotic metabolite	low
butylated hydroxytoluene	phenols	antioxidant; ferroptosis inhibitor; food additive; geroprotector	low
2,6-di-tert-butylphenol	alkylbenzene; phenols	antioxidant	low
dimethophrine	methoxybenzenes; phenols		low
4-vinyl-2,6-dimethoxyphenol	methoxybenzenes; phenols		low
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor	low
closantel	aromatic amide; monocarboxylic acid amide; monochlorobenzenes; nitrile; organoiodine compound; phenols		low
fomesafen	aromatic ether; C-nitro compound; monochlorobenzenes; N-sulfonylcarboxamide; organofluorine compound; phenols	agrochemical; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
naxagolide	organic heterotricyclic compound; phenols; tertiary amino compound	anticonvulsant; antiparkinson drug; dopamine agonist	low
4-vinylphenol	phenols	human urinary metabolite; human xenobiotic metabolite	low
4-ethylguaiacol	methoxybenzenes; phenols		low
nelfinavir	aryl sulfide; benzamides; organic heterobicyclic compound; phenols; secondary alcohol; tertiary amino compound	antineoplastic agent; HIV protease inhibitor	low
salicylhydroxamic acid	hydroxamic acid; phenols	antibacterial drug; EC 1.11.2.2 (myeloperoxidase) inhibitor; EC 3.5.1.5 (urease) inhibitor; trypanocidal drug	low
guaethol	aromatic ether; phenols; volatile organic compound	flavouring agent	low
cresatin	benzoate ester; phenols		low
4-trifluoromethylphenol	(trifluoromethyl)benzenes; phenols	drug metabolite; marine xenobiotic metabolite	low
3-pentadecylphenol	phenols		low
chavicol	phenols; phenylpropanoid		low
ibopamine	benzoate ester; phenols		low
4-methoxyestradiol	17beta-hydroxy steroid; 3-hydroxy steroid; aromatic ether; phenols	estrogen; human metabolite; rat metabolite	low
2-hydroxy-4-methoxybenzaldehyde	methoxybenzenes; phenols		low
methyl syringate	benzoate ester; dimethoxybenzene; phenols	plant metabolite	low
vanitiolide	methoxybenzenes; phenols		low
tubulosine	beta-carbolines; isoquinoline alkaloid; isoquinolines; phenols; secondary amino compound; tertiary amino compound		low
rubrofusarin	aromatic ether; benzochromenone; phenols; polyketide	biological pigment; EC 1.14.18.1 (tyrosinase) inhibitor; fungal metabolite	low
dauricine	aromatic ether; bisbenzylisoquinoline alkaloid; isoquinolines; phenols; tertiary amino compound	plant metabolite	low
2,5-di-tert-butyl-4-hydroxyanisole	methoxybenzenes; phenols		low
methyl gentisate	benzoate ester; phenols		low
4-hydroxyindole	hydroxyindoles; phenols		low
benzoyltyrosine ethyl ester	benzamides; ethyl ester; L-tyrosine derivative; phenols	chromogenic compound	low
methyl 3-(4-hydroxyphenyl)propionate	methyl ester; phenols	nitrification inhibitor; plant growth regulator	low
4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene	phenols		low
acetaminophen mercapturate	acetamides; organic sulfide; phenols; S-substituted N-acetyl-L-cysteine	drug metabolite; human urinary metabolite; rat metabolite	low
adriamycinol	aminoglycoside; anthracycline antibiotic; aromatic ether; deoxy hexoside; p-quinones; phenols; polyol; tetracenequinones	cardiotoxic agent; drug metabolite	low
3-hydroxymandelic acid	2-hydroxy monocarboxylic acid; phenols	human metabolite	low
n-acetyltyrosine, (dl)-isomer	N-acetyl-amino acid; phenols; tyrosine derivative	human urinary metabolite	low
2-tyrosine	non-proteinogenic alpha-amino acid; phenols; phenylalanine derivative		low
2-amino-5-chlorophenol	monochlorobenzenes; phenols; primary amino compound		low
beta-peltatin	furonaphthodioxole; gamma-lactone; lignan; organic heterotetracyclic compound; phenols	antineoplastic agent; plant metabolite	low
alpha-peltatin	furonaphthodioxole; gamma-lactone; lignan; organic heterotetracyclic compound; phenols	antineoplastic agent; metabolite	low
laudanine	aromatic ether; benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; phenols; racemate		low
tyrphostin 8	phenols		low
4-hydroxymexiletine	aromatic ether; phenols		low
sugiol	abietane diterpenoid; carbotricyclic compound; cyclic terpene ketone; meroterpenoid; phenols	antineoplastic agent; antioxidant; antiviral agent; plant metabolite; radical scavenger	low
gamma-glutamyltyrosine	dicarboxylic acid; dipeptide; phenols; primary amino compound; secondary carboxamide	human metabolite	low
6-paradol	ketone; monomethoxybenzene; phenols		low
2-hydroxy-5-methoxybenzaldehyde	benzaldehydes; monomethoxybenzene; phenols		low
4-(4-hydroxyphenyl)-2-butanol	phenols		low
tetrangulol	p-quinones; phenols; tetraphenes	bacterial metabolite	low
terphenyllin	dimethoxybenzene; para-terphenyl; phenols	Aspergillus metabolite; mycotoxin	low
2,3-bis(4-hydroxyphenyl)-propionitrile	nitrile; phenols	estrogen receptor agonist	low
3-(3-hydroxyphenyl)-3-hydroxypropanoic acid	dihydroxy monocarboxylic acid; phenols	human urinary metabolite	low
sn 38	delta-lactone; phenols; pyranoindolizinoquinoline; tertiary alcohol	antineoplastic agent; apoptosis inducer; drug metabolite; EC 5.99.1.2 (DNA topoisomerase) inhibitor	low
ly 117018	1-benzothiophenes; aromatic ketone; N-alkylpyrrolidine; phenols	bone density conservation agent; estrogen receptor antagonist; estrogen receptor modulator	low
5-hydroxypropafenone	phenols		low
4'-hydroxydiclofenac	dichlorobenzene; monocarboxylic acid; phenols; secondary amino compound	allergen; drug metabolite	low
3-chloro-4-hydroxyphenylacetic acid	hydroxy monocarboxylic acid; monochlorobenzenes; phenols	mammalian metabolite	low
eseroline	phenols; pyrroloindole	human xenobiotic metabolite; opioid analgesic	low
hydrangenol	dihydroisocoumarins; phenols	anti-allergic agent; plant metabolite	low
maculosin	dipeptide; homodetic cyclic peptide; phenols; pyrrolopyrazine	metabolite	low
2-o-methylpyrogallol	methoxybenzenes; phenols		low
dopamine 3-o-sulfate	aryl sulfate; phenols; primary amino compound; zwitterion	human blood serum metabolite; human urinary metabolite	low
estriol-16 alpha-glucuronide	17beta-hydroxy steroid; 3-hydroxy steroid; beta-D-glucosiduronic acid; phenols; steroid glucosiduronic acid	human urinary metabolite	low
emodin anthrone	anthracenone; phenols	fungal metabolite	low
4'-demethylpodophyllotoxin	furonaphthodioxole; organic heterotetracyclic compound; phenols	metabolite	low
4'-demethylepipodophyllotoxin	furonaphthodioxole; organic heterotetracyclic compound; phenols	antineoplastic agent	low
dopamine 4-o-sulfate	aryl sulfate; phenols; primary amino compound; zwitterion	human blood serum metabolite; human urinary metabolite	low
rubimaillin	benzochromene; methyl ester; phenols	acyl-CoA:cholesterol acyltransferase 2 inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; neuroprotective agent; NF-kappaB inhibitor; plant metabolite	low
desvenlafaxine	cyclohexanols; phenols; tertiary amino compound	antidepressant; drug metabolite; marine xenobiotic metabolite	low
ay 25545	acetate ester; aromatic ether; C-glycosyl compound; naphthoisochromene; olefinic compound; phenols; tertiary amine	antimicrobial agent; antineoplastic agent; bacterial metabolite	low
tilivalline	indole alkaloid; indoles; phenols; pyrrolobenzodiazepine	bacterial metabolite; microtubule-stabilising agent; toxin	low
4-acetamidophenyl-2-thiophenecarboxylate	benzoate ester; phenols		low
yakuchinone-a	ketone; monomethoxybenzene; phenols	antineoplastic agent; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; EC 1.14.13.39 (nitric oxide synthase) inhibitor; metabolite	low
cd 437	adamantanes; monocarboxylic acid; naphthoic acid; phenols	apoptosis inducer; retinoic acid receptor gamma agonist	low
aclacinomycin	aminoglycoside; anthracycline; deoxy hexoside; methyl ester; monosaccharide derivative; phenols; polyketide; tertiary alcohol; tetracenequinones; zwitterion	antimicrobial agent; antineoplastic agent; metabolite	low
n-methylserotonin	phenols; tryptamines	human metabolite; plant metabolite	low
endocrocin	monocarboxylic acid; phenols; trihydroxyanthraquinone	metabolite	low
actinodaphine	aporphine alkaloid; aromatic ether; organic heteropentacyclic compound; phenols; secondary amino compound	antibacterial agent; antifungal agent; antineoplastic agent; apoptosis inducer; plant metabolite; platelet aggregation inhibitor; topoisomerase inhibitor	low
sulochrin	benzophenones; carboxylic ester; phenols	metabolite	low
isohomovanillic acid	aromatic ether; phenols; phenylacetic acids	metabolite	low
3,5-diiodothyropropionic acid	aromatic ether; monocarboxylic acid; organoiodine compound; phenols		low
4-hydroxybenzyl isothiocyanate	phenols		low
4'-demethyldesoxypodophyllotoxin	furonaphthodioxole; gamma-lactone; lignan; methoxybenzenes; phenols	antineoplastic agent; antioxidant; immunosuppressive agent; plant metabolite	low
myricanone	aromatic ether; cyclic ketone; diarylheptanoid; methoxybenzenes; phenols	antineoplastic agent; plant metabolite	low
pannarin	aldehyde; aromatic ether; depsidones; organic heterotricyclic compound; organochlorine compound; phenols	antimicrobial agent; antineoplastic agent; apoptosis inducer; lichen metabolite	low
gingerdione	beta-diketone; monomethoxybenzene; phenols		low
etilefrine hydrochloride	phenols		low
8-gingerol	beta-hydroxy ketone; monomethoxybenzene; phenols		low
10-gingerol	beta-hydroxy ketone; monomethoxybenzene; phenols		low
pluviatolide	aromatic ether; benzodioxoles; butan-4-olide; lignan; phenols	plant metabolite	low
nordihydrocapsaicin	methoxybenzenes; phenols		low
erysodine	aromatic ether; diether; Erythrina alkaloid; organic heterotetracyclic compound; phenols	antiparasitic agent; nicotinic antagonist; phytogenic insecticide	low
isomhpg	methoxybenzenes; phenols		low
rubrofusarin B	aromatic ether; benzochromenone; naphtho-gamma-pyrone; phenols; polyketide	Aspergillus metabolite	low
top 53	furonaphthodioxole; gamma-lactone; organic heterotetracyclic compound; phenols; tertiary amino compound	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	low
2,5-dihydroxybenzyl alcohol	aromatic primary alcohol; phenols	antineoplastic agent; antioxidant; apoptosis inhibitor; fungal metabolite	low
n-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide	anilide fungicide; aromatic amide; dichlorobenzene; monocarboxylic acid amide; phenols	antifungal agrochemical; EC 1.14.13.72 (methylsterol monooxygenase) inhibitor; sterol biosynthesis inhibitor	low
deferasirox	benzoic acids; monocarboxylic acid; phenols; triazoles	iron chelator	low
succinobucol	benzoate ester; phenols		low
fonsecin	aromatic ether; cyclic hemiketal; heptaketide; naphtho-gamma-pyrone; phenols	Aspergillus metabolite; marine metabolite	low
4-allyl-2,6-dimethoxyphenol	dimethoxybenzene; phenols; phenylpropanoid		low
lariciresinol	aromatic ether; lignan; oxolanes; phenols; primary alcohol	antifungal agent; plant metabolite	low
4-(2-Amino-1,3-thiazol-4-yl)phenol	phenols		low
3-(2-Methylpropanoyloxy)-8-(2-methylbutanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene	benzoate ester; phenols		low
maackiain	phenols; pterocarpans		low
2-methoxyestrone	17-oxo steroid; 3-hydroxy steroid; alicyclic ketone; aromatic ether; phenolic steroid; phenols	human metabolite; mouse metabolite	low
metoprolol tartrate	alcohol; phenols		low
ferruginol	abietane diterpenoid; carbotricyclic compound; meroterpenoid; phenols	antibacterial agent; antineoplastic agent; plant metabolite; protective agent	low
abyssinone i	monohydroxyflavanone; phenols	apoptosis inhibitor; plant metabolite	low
abyssinone v	4'-hydroxyflavanones; phenols; trihydroxyflavanone	metabolite	low
oxyacanthine	bisbenzylisoquinoline alkaloid; isoquinolines; macrocycle; phenols; tertiary amino compound		low
agnuside	benzoate ester; beta-D-glucoside; cyclopentapyran; iridoid monoterpenoid; monosaccharide derivative; phenols; terpene glycoside	anti-inflammatory agent; cyclooxygenase 2 inhibitor; plant metabolite; pro-angiogenic agent	low
cleomiscosin a	aromatic ether; delta-lactone; organic heterotricyclic compound; phenols; primary alcohol	anti-inflammatory agent; metabolite	low
pyochelin	monocarboxylic acid; phenols; thiazolidines	metabolite; siderophore	low
yersiniabactin	monocarboxylic acid; phenols; secondary alcohol; thiazolidines	bacterial metabolite; siderophore	low
sr 12813	organic phosphonate; phenols	pregnane X receptor agonist	low
mycophenolic acid	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic	low
stigmatellin	aromatic ether; chromones; olefinic compound; phenols	bacterial metabolite; quinol oxidation site inhibitor	low
afimoxifene	phenols; tertiary amino compound	antineoplastic agent; estrogen receptor antagonist; metabolite	low
3-hydroxyhippuric acid	N-acylglycine; phenols	metabolite	low
aclarubicin	aminoglycoside; anthracycline; methyl ester; phenols; polyketide; tetracenequinones; trisaccharide derivative; zwitterion	antimicrobial agent; antineoplastic agent; apoptosis inducer; bacterial metabolite; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	low
teniposide	aromatic ether; beta-D-glucoside; cyclic acetal; furonaphthodioxole; gamma-lactone; monosaccharide derivative; phenols; thiophenes	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	low
chavibetol	methoxybenzenes; phenols		low
piperlactam s	alkaloid; aromatic ether; gamma-lactam; organic heterotetracyclic compound; phenols	anti-inflammatory agent; antioxidant; plant metabolite	low
2-hydroxycinnamic acid	2-coumaric acid; phenols	antioxidant; metabolite	low
2'-hydroxychalcone	chalcones; phenols	anti-inflammatory agent	low
6-(hexylthio)-4-(4-hydroxyphenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile	phenols		low
5-(4-bromophenyl)-4-(4-hydroxy-3-methoxyphenyl)-3-methyl-2,4-dihydropyrrolo[3,4-c]pyrazol-6-one	methoxybenzenes; phenols		low
2-methoxy-6-[[(1-propyl-5-benzimidazolyl)amino]methyl]phenol	methoxybenzenes; phenols		low
2-methoxy-6-[[(1-methyl-2-benzimidazolyl)amino]methyl]phenol	methoxybenzenes; phenols		low
acetic acid [4-[oxo-(2-phenylethylamino)methyl]phenyl] ester	benzoate ester; phenols		low
acetic acid [2-(4-acetamido-6-phenyl-1,3,5-triazin-2-yl)phenyl] ester	benzoate ester; phenols		low
zucapsaicin	methoxybenzenes; phenols		low
2-hydroxybenzoic acid [2-[[(1-methyl-2-pyrrolyl)-oxomethyl]amino]-2-oxoethyl] ester	benzoate ester; phenols		low
2-[2-nitro-4-(trifluoromethyl)phenyl]sulfinylacetic acid (4-chlorophenyl) ester	benzoate ester; phenols		low
acetic acid [4-[(1-oxo-2-phenylethyl)amino]phenyl] ester	benzoate ester; phenols		low
2-hydroxy-4-methylbenzoic acid [2-(2-chloroanilino)-2-oxoethyl] ester	benzoate ester; phenols		low
2-[[2-[(2-hydroxyphenyl)-oxomethoxy]-1-oxoethyl]amino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid methyl ester	benzoate ester; phenols		low
3-hydroxybenzoic acid [2-(1H-indol-3-yl)-2-oxoethyl] ester	benzoate ester; phenols		low
4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylic acid (3-methylcyclohexyl) ester	methoxybenzenes; phenols		low
4-(4-hydroxy-3-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylic acid (4-methoxyphenyl)methyl ester	methoxybenzenes; phenols		low
2-(3,5-diphenyl-3,4-dihydropyrazol-2-yl)-2-(4-hydroxy-3-methoxyphenyl)acetonitrile	methoxybenzenes; phenols		low
2-[[3-(methylthio)-1,2,4-thiadiazol-5-yl]thio]acetic acid (4-acetamidophenyl) ester	benzoate ester; phenols		low
monastrol	enoate ester; ethyl ester; phenols; racemate; thioureas	antileishmanial agent; antimitotic; antineoplastic agent; EC 3.5.1.5 (urease) inhibitor	low
3-methoxy-4-hydroxyphenylglycol sulfate	alcohol; phenols		low
5-hydroxydiclofenac	dichlorobenzene; monocarboxylic acid; phenols; secondary amino compound	allergen; drug metabolite	low
4-hydroxyphenethylene glycol	phenols		low
5-hydroxybenzimidazole	benzimidazoles; phenols	bacterial metabolite; human metabolite; rat metabolite	low
5-(diethylsulfamoyl)-2-hydroxybenzoic acid [2-oxo-2-[4-(trifluoromethoxy)anilino]ethyl] ester	benzoate ester; phenols		low
n,o-didesmethylvenlafaxine	cyclohexanols; phenols; secondary amino compound	drug metabolite; marine xenobiotic metabolite	low
2-hydroxybenzoic acid [2-(2-ethoxyanilino)-2-oxo-1-phenylethyl] ester	benzoate ester; phenols		low
sb 415286	C-nitro compound; maleimides; monochlorobenzenes; phenols; secondary amino compound; substituted aniline	antioxidant; apoptosis inducer; EC 2.7.11.26 (tau-protein kinase) inhibitor; neuroprotective agent	low
acetic acid [2-[2-acetyl-3-(4-methoxyphenyl)-3,4-dihydropyrazol-5-yl]phenyl] ester	benzoate ester; phenols		low
2-hydroxy-5-[(4-methoxyphenyl)sulfamoyl]benzoic acid [2-[1-(3-bicyclo[2.2.1]heptanyl)ethylamino]-2-oxoethyl] ester	benzoate ester; phenols		low
3,5-dimethyl-4-oxo-6-thieno[2,3-d]pyrimidinecarboxylic acid (4-methylphenyl) ester	benzoate ester; phenols		low
1,3,5-tris(4-hydroxyphenyl)-4-propyl-1h-pyrazole	phenols; pyrazoles	estrogen receptor agonist	low
6-iodonordihydrocapsaicin	methoxybenzenes; phenols		low
3-(4-hydroxyphenyl)-1-propane	4-hydroxycinnamyl alcohol; phenols; phenylpropanoid	monolignol	low
sinapaldehyde	cinnamaldehydes; dimethoxybenzene; phenols	antifungal agent; plant metabolite	low
mycophenolate mofetil	carboxylic ester; ether; gamma-lactone; phenols; tertiary amino compound	anticoronaviral agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; immunosuppressive agent; prodrug	low
isobutrin	beta-D-glucoside; chalcones; monosaccharide derivative; phenols	anti-inflammatory agent; hepatoprotective agent; plant metabolite	low
euxanthone	phenols; xanthones	metabolite; plant metabolite	low
mangostin	aromatic ether; phenols; xanthones	antimicrobial agent; antineoplastic agent; antioxidant; plant metabolite	low
swerchirin	aromatic ether; phenols; xanthones	hypoglycemic agent; metabolite	low
shogaol	enone; monomethoxybenzene; phenols		low
4-hydroxychalcone	chalcones; phenols	antihypertensive agent; plant metabolite	low
4'-hydroxychalcone	chalcones; phenols	anti-inflammatory agent; antineoplastic agent	low
olvanil	methoxybenzenes; phenols		low
n-cinnamoyltyramine	cinnamamides; phenols; secondary carboxamide	allelochemical; antimicrobial agent; phytoalexin; platelet aggregation inhibitor	low
methyl brevifolincarboxylate	cyclic ketone; delta-lactone; organic heterotricyclic compound; phenols	EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; metabolite; platelet aggregation inhibitor; radical scavenger; vasodilator agent	low
3-deoxysappanchalcone	chalcones; monomethoxybenzene; phenols	metabolite	low
rhamnazin	aromatic ether; dimethoxyflavone; phenols; trihydroxyflavone	antineoplastic agent; plant metabolite	low
alpha-cyano-4-hydroxycinnamic acid	monohydroxycinnamic acid; nitrile; phenols	MALDI matrix material	low
macluraxanthone b	phenols; xanthones	anti-HIV agent; antineoplastic agent; metabolite	low
flavokawain b	chalcones; dimethoxybenzene; phenols	anti-inflammatory agent; antileishmanial agent; antineoplastic agent; apoptosis inducer; metabolite	low
lichexanthone	aromatic ether; phenols; xanthones	plant metabolite	low
alternariol	benzochromenone; phenols	EC 3.1.1.8 (cholinesterase) inhibitor; metabolite; mycotoxin	low
sorbicillin	phenols		low
decussatin	aromatic ether; phenols; xanthones	plant metabolite	low
gamma-mangostin	phenols; xanthones	antineoplastic agent; plant metabolite; protein kinase inhibitor	low
1,7-dihydroxy-4-methoxyxanthone	aromatic ether; phenols; xanthones	metabolite; plant metabolite	low
resiniferatoxin	carboxylic ester; diterpenoid; enone; monomethoxybenzene; organic heteropentacyclic compound; ortho ester; phenols; tertiary alpha-hydroxy ketone	analgesic; neurotoxin; plant metabolite; TRPV1 agonist	low
flavasperone	aromatic ether; naphtho-gamma-pyrone; phenols	acyl-CoA:cholesterol acyltransferase 2 inhibitor; antiviral agent; Aspergillus metabolite; marine metabolite	low
su 1498	enamide; monocarboxylic acid amide; nitrile; phenols; secondary carboxamide	vascular endothelial growth factor receptor antagonist	low
n-feruloylserotonin	aromatic ether; cinnamamides; hydroxyindoles; phenols; secondary carboxamide	plant metabolite	low
tyrphostin ag825	aromatic ether; benzothiazoles; enamide; nitrile; organic sulfide; phenols; primary carboxamide	epidermal growth factor receptor antagonist	low
eupomatenoid 6	benzofurans; phenols	anti-inflammatory agent; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; NF-kappaB inhibitor; plant metabolite	low
7-hydroxy-2-(n-n-propyl-n-(3-iodo-2'-propenyl)-amino)tetralin	organoiodine compound; phenols; tertiary amino compound; tetralins	dopamine agonist	low
monorden	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor	low
cefatrizine	amino acid amide; carboxylic acid; cephalosporin; phenols; semisynthetic derivative; triazoles	antibacterial drug; EC 2.7.11.20 (elongation factor 2 kinase) inhibitor	low
sibiromycin	aminoglycoside antibiotic; hemiaminal; phenols; pyrrolobenzodiazepine	antineoplastic agent; bacterial metabolite	low
(8)-shogaol	enone; monomethoxybenzene; phenols		low
(10)-shogaol	enone; monomethoxybenzene; phenols		low
arvanil	methoxybenzenes; phenols		low
ro 25-6981	benzenes; phenols; piperidines; secondary alcohol; tertiary amino compound	anticonvulsant; antidepressant; neuroprotective agent; NMDA receptor antagonist	low
3-tyrosine	hydroxyphenylalanine; L-alpha-amino acid zwitterion; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; phenols	plant metabolite	low
camostat	aromatic ether; phenols		low
jasplakinolide	cyclodepsipeptide; phenols	actin polymerisation inducer; animal metabolite; antifungal agent; antineoplastic agent; apoptosis inducer; marine metabolite; neuroprotective agent	low
capsiate	carboxylic ester; monomethoxybenzene; phenols	angiogenesis inhibitor; anti-allergic agent; anti-inflammatory agent; antioxidant; capsaicin receptor agonist; hypoglycemic agent; plant metabolite	low
fr 148083	aromatic ether; macrolide; phenols; secondary alcohol; secondary alpha-hydroxy ketone	antibacterial agent; antineoplastic agent; metabolite; NF-kappaB inhibitor	low
tmc-95a	indoles; lactam; macrocycle; phenols; secondary alcohol; tertiary alcohol	antimicrobial agent; antineoplastic agent; bacterial metabolite; fungal metabolite; proteasome inhibitor	low
topopyrone c	naphthochromene; p-quinones; phenols	antimicrobial agent; antineoplastic agent; antiviral agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; Penicillium metabolite	low
pi103	aromatic amine; morpholines; organic heterotricyclic compound; phenols; tertiary amino compound	antineoplastic agent; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; mTOR inhibitor	low
estin	1-benzofurans; ether; methyl ester; organochlorine compound; oxaspiro compound; phenols	Aspergillus metabolite; Penicillium metabolite	low
mdl 105725	methoxybenzenes; phenols		low
ustiloxin b	aromatic ether; heterodetic cyclic peptide; macrocycle; phenols; secondary alcohol; secondary carboxamide; sulfoxide	Aspergillus metabolite; microtubule-destabilising agent; mycotoxin	low
nidulalin a	methyl ester; phenols; xanthones	antimicrobial agent; antineoplastic agent; Penicillium metabolite	low
hypothemycin	aromatic ether; diol; enone; epoxide; macrolide; phenols; polyketide; secondary alpha-hydroxy ketone	antifungal agent; antineoplastic agent; EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor; fungal metabolite	low
vernakalant	alcohol; phenols		low
elloramycin	alpha-L-rhamnoside; carboxylic ester; enol ether; enone; methyl ester; monosaccharide derivative; phenols; tertiary alpha-hydroxy ketone; tetracenomycin	antimicrobial agent; bacterial metabolite	low
arachidonoylserotonin	N-acylserotonin; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; capsaicin receptor antagonist; EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor; human metabolite; signalling molecule	low
avenanthramide b	amidobenzoic acid; cinnamamides; monohydroxybenzoic acid; monomethoxybenzene; phenols; secondary carboxamide	antineoplastic agent; apoptosis inducer; phytoalexin	low
vilanterol	benzyl alcohols; dichlorobenzene; ether; phenols; secondary amino compound	beta-adrenergic agonist; bronchodilator agent	low
lactonamycin	gamma-lactone; organic heterohexacyclic compound; phenols; trideoxyhexose derivative	antibacterial agent; antimicrobial agent; metabolite	low
nigerloxin	aromatic ether; benzamides; benzoic acids; phenols; styrenes	antioxidant; Aspergillus metabolite; EC 1.1.1.21 (aldehyde reductase) inhibitor; lipoxygenase inhibitor; radical scavenger	low
1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one	diarylheptanoid; enone; phenols	plant metabolite	low
tmc-95b	indoles; lactam; macrocycle; phenols; secondary alcohol; tertiary alcohol	antimicrobial agent; antineoplastic agent; fungal metabolite; proteasome inhibitor	low
1,7-bis(4-hydroxyphenyl)hepta-4E-6E-dien-3-one	diarylheptanoid; enone; phenols	plant metabolite	low
cardanol	phenols		low
glyceryl ferulate	1-monoglyceride; aromatic ether; enoate ester; phenols	antioxidant; plant metabolite; ultraviolet filter	low
laurinterol	organobromine compound; phenols; sesquiterpenoid	antibacterial agent; apoptosis inducer; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; metabolite	low
10-isobutyryloxy-8,9-epoxythymol isobutyrate	benzoate ester; phenols		low
olodaterol	aromatic ether; benzoxazine; phenols; secondary alcohol; secondary amino compound	beta-adrenergic agonist; bronchodilator agent	low
diversonol	phenols; tertiary alcohol	antibacterial agent; metabolite	low
alloin	anthracenes; C-glycosyl compound; cyclic ketone; phenols	laxative; metabolite	low
sarpagine	indole alkaloid; phenols; primary alcohol; secondary amino compound; tertiary amino compound		low
1-O-feruloyl-beta-D-glucose	aromatic ether; beta-D-glucoside; cinnamate ester; phenols	antioxidant; plant metabolite	low
ligstroside	beta-D-glucoside; diester; methyl ester; phenols; pyrans; secoiridoid glycoside	antineoplastic agent; plant metabolite	low
shamixanthone	cyclic ketone; phenols; pyranoxanthene	metabolite	low
siphonazole	methoxybenzenes; phenols		low
vx-770	aromatic amide; monocarboxylic acid amide; phenols; quinolone	CFTR potentiator; orphan drug	low
4-[[(4S)-3-[2-(1-adamantyl)ethyl]-2-amino-4,5-dihydroimidazol-4-yl]methyl]phenol	phenols		low
3-(1,3-benzodioxol-5-yl)-3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(3-methyl-1-piperidinyl)-1-propanone	methoxybenzenes; phenols		low
respirantin	benzamides; cyclodepsipeptide; formamides; phenols	antimicrobial agent; antineoplastic agent; metabolite	low
3,4-dihydroxyphenylethanol-elenolic acid dialdehyde	alcohol; phenols		low
avilamycin a	benzoate ester; cyclic acetal; dichlorobenzene; oligosaccharide derivative; ortho ester; oxaspiro compound; phenols; tertiary alpha-hydroxy ketone	antimicrobial agent; bacterial metabolite	low
cathestatin b	dicarboxylic acid monoamide; epoxide; monocarboxylic acid; phenols; primary amino compound	antimicrobial agent; cysteine protease inhibitor; Penicillium metabolite	low
bromophycolide a	diterpenoid; macrolide; organobromine compound; phenols; tertiary alcohol	anti-HIV agent; antibacterial agent; antifungal agent; antimalarial; antineoplastic agent; metabolite	low
diorcinol	aromatic ether; phenols	fungal metabolite; marine metabolite; metabolite	low
n-trans-feruloyloctopamine	methoxybenzenes; phenols		low
marinopyrrole a	aromatic ketone; organochlorine compound; phenols; pyrroles	antibacterial agent; antimicrobial agent; antineoplastic agent; bacterial metabolite; marine metabolite	low
chondramide c	chondramide; indoles; phenols	antineoplastic agent; bacterial metabolite	low
debromoaplysiatoxin	aplysiatoxins; cyclic hemiketal; ether; organic heterotricyclic compound; phenols; secondary alcohol; spiroketal	algal metabolite; carcinogenic agent; cyanotoxin; marine metabolite; protein kinase C agonist	low
(E)-5-hydroxy-6-(3-methylbut-2-enyl)-2-(pent-1-enyl)benzofuran-4-carbaldehyde	1-benzofurans; aldehyde; phenols	Aspergillus metabolite; Chaetomium metabolite; radical scavenger	low
1-(4-hydroxyphenyl)-7-phenyl-(6E)-hept-6-en-3-one	diarylheptanoid; ketone; phenols	plant metabolite	low
hordatine a	aromatic ether; benzofurans; dicarboxylic acid diamide; guanidines; phenols	adrenergic antagonist; metabolite	low
chondramide a	chondramide; indoles; phenols	antineoplastic agent; bacterial metabolite	low
quinolobactin	aromatic ether; monohydroxyquinoline; phenols; quinolinemonocarboxylic acid	bacterial metabolite; siderophore	low
novobiocin	carbamate ester; ether; hexoside; hydroxycoumarin; monocarboxylic acid amide; monosaccharide derivative; phenols	antibacterial agent; antimicrobial agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; Escherichia coli metabolite; hepatoprotective agent	low
ilicicolin h	aromatic ketone; carbobicyclic compound; ilicicolin; monohydroxypyridine; octahydronaphthalenes; phenols; pyridone	antimicrobial agent; mitochondrial respiratory-chain inhibitor	low
naloxegol	aromatic ether; organic heteropentacyclic compound; phenols; polyether; tertiary alcohol	cathartic; mu-opioid receptor antagonist	low
fertaric acid	aromatic ether; cinnamate ester; dicarboxylic acid; phenols; tetraric acid derivative		low
callipeltin a	cyclodepsipeptide; guanidines; lactone; oligopeptide; phenols	anti-HIV-1 agent; antifungal agent; metabolite	low
opt 80	carboxylic ester; glycoside; macrolide antibiotic; organochlorine compound; phenols	antibacterial drug; bacterial metabolite; EC 2.7.7.6 (RNA polymerase) inhibitor	low
brasilicardin a	benzoate ester; carbotricyclic compound; diterpenoid; N-acetyl-D-glucosaminide; non-proteinogenic alpha-amino acid; phenols	antimicrobial agent; antineoplastic agent; bacterial metabolite; immunosuppressive agent	low
ML355	benzothiazoles; monomethoxybenzene; phenols; secondary amino compound; substituted aniline; sulfonamide	EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor; platelet aggregation inhibitor	low
acarbose	chondramide; indoles; organochlorine compound; phenols	antineoplastic agent; bacterial metabolite	low
pf-06687252	azabicycloalkane; enone; phenols; pyridines		low
chondramide d	chondramide; indoles; phenols	antineoplastic agent; bacterial metabolite	low
biliatresone	aromatic ether; aromatic ketone; benzodioxoles; enone; phenols	plant metabolite; toxin	low
can 508	aromatic amine; monoazo compound; phenols; pyrazoles	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor	low
nu 1025	phenols; quinazolines	EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor	low
quininib	phenols; styrylquinoline	angiogenesis inhibitor	low
pp242	aromatic amine; biaryl; hydroxyindoles; phenols; primary amino compound; pyrazolopyrimidine	antineoplastic agent; mTOR inhibitor	low
dehydroluciferin	1,3-thiazolemonocarboxylic acid; benzothiazoles; biaryl; phenols	animal metabolite; luciferin	low
sotorasib	acrylamides; methylpyridines; monofluorobenzenes; N-acylpiperazine; phenols; pyridopyrimidine; tertiary amino compound; tertiary carboxamide	antineoplastic agent	low
tilimycin	phenols; pyrrolobenzodiazepine	alkylating agent; apoptosis inducer; bacterial metabolite; toxin	low
agmatine	guanidines; primary amino compound	Escherichia coli metabolite; mouse metabolite	low
aminoethylphosphonic acid	phosphonic acids; primary amino compound; zwitterion	human metabolite; metabolite; mouse metabolite	low
4-amino-1,2-oxazolidin-3-one	hydroxamic acid ester; oxazolidines; primary amino compound; serine derivative		low
phosphorylethanolamine	phosphoethanolamine; primary amino compound	algal metabolite; human metabolite; mouse metabolite	low
n-(3-(aminomethyl)benzyl)acetamidine	aralkylamine; carboxamidine; primary amino compound	angiogenesis inhibitor; EC 1.14.13.39 (nitric oxide synthase) inhibitor; geroprotector	low
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine	imidazopyridine; primary amino compound	carcinogenic agent; mutagen	low
2-aminoethoxydiphenyl borate	organoboron compound; primary amino compound	calcium channel blocker; IP3 receptor antagonist; potassium channel opener	low
5-(nonyloxy)tryptamine	aromatic ether; primary amino compound; tryptamines	serotonergic agonist	low
5-methoxytryptamine	aromatic ether; primary amino compound; tryptamines	5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist	low
alendronate	1,1-bis(phosphonic acid); primary amino compound	bone density conservation agent; EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor	low
amfenac	amino acid; benzophenones; oxo monocarboxylic acid; primary amino compound; substituted aniline	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug	low
ampyrone	primary amino compound; pyrazolone	antipyretic; antirheumatic drug; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; marine xenobiotic metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug	low
2-aminothiazole	1,3-thiazoles; primary amino compound		low
amlodipine	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent	low
baclofen	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant	low
benserazide	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor	low
butamben	amino acid ester; benzoate ester; primary amino compound; substituted aniline	local anaesthetic	low
cgs 15943	aromatic amine; biaryl; furans; organochlorine compound; primary amino compound; quinazolines; triazoloquinazoline	adenosine A1 receptor antagonist; adenosine A2A receptor antagonist; antineoplastic agent; central nervous system stimulant	low
cystamine	organic disulfide; primary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor	low
fipronil	(trifluoromethyl)benzenes; dichlorobenzene; nitrile; primary amino compound; pyrazoles; sulfoxide		low
tele-methylhistamine	imidazoles; primary amino compound	human metabolite; mouse metabolite	low
mescaline	methoxybenzenes; phenethylamine alkaloid; primary amino compound	hallucinogen	low
mexiletine	aromatic ether; primary amino compound	anti-arrhythmia drug	low
monodansylcadaverine	aminonaphthalene; primary amino compound; sulfonamide; tertiary amino compound	EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor; fluorochrome; protective agent	low
entinostat	benzamides; carbamate ester; primary amino compound; pyridines; substituted aniline	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor	low
muscimol	alkaloid; isoxazoles; primary amino compound	fungal metabolite; GABA agonist; oneirogen; psychotropic drug	low
n-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamide	naphthalenes; organochlorine compound; primary amino compound; sulfonamide		low
oxidopamine	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin	low
o-methyltyramine	primary amino compound		low
2-aminopropanol	amino alcohol; primary alcohol; primary amino compound		low
sulfaphenazole	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor	low
terazosin	furans; piperazines; primary amino compound; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; antineoplastic agent	low
tosufloxacin	1,8-naphthyridine derivative; amino acid; aminopyrrolidine; monocarboxylic acid; organofluorine compound; primary amino compound; quinolone antibiotic; tertiary amino compound		low
tyramine	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter	low
tromethamine	primary amino compound; triol	buffer	low
2-anisidine	monomethoxybenzene; primary amino compound; substituted aniline	genotoxin; reagent	low
aminacrine	aminoacridines; primary amino compound	acid-base indicator; antiinfective agent; antiseptic drug; fluorescent dye; MALDI matrix material; mutagen	low
4-anisidine	methoxybenzenes; primary amino compound; substituted aniline	genotoxin; reagent	low
betazole	primary amino compound; pyrazoles	diagnostic agent; gastrointestinal drug; histamine agonist	low
phenetidine	aromatic ether; primary amino compound; substituted aniline	drug metabolite	low
6-aminonicotinamide	aminopyridine; monocarboxylic acid amide; primary amino compound	antimetabolite; EC 1.1.1.44 (NADP(+)-dependent decarboxylating phosphogluconate dehydrogenase) inhibitor; teratogenic agent	low
kynuramine	kynurenamines; primary amino compound	metabolite	low
neutral red base	aromatic amine; phenazines; primary amino compound; tertiary amino compound	acid-base indicator; dye; two-colour indicator	low
3-tyramine	primary amino compound; tyramines	human urinary metabolite; neurotransmitter	low
2,6-diaminotoluene	diamine; primary amino compound	mutagen	low
pyrazon	benzenes; organochlorine compound; primary amino compound; pyridazinone	environmental contaminant; herbicide; xenobiotic	low
2-aminothiazoline	1,3-thiazoles; primary amino compound		low
3-phenylpropylamine	benzenes; phenylalkylamine; primary amino compound		low
4-aminobutyric acid methyl ester	amino acid ester; methyl ester; primary amino compound		low
asulam	carbamate ester; primary amino compound; substituted aniline; sulfonamide	agrochemical; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; herbicide; xenobiotic	low
galactosamine	D-galactosamine; primary amino compound	toxin	low
didesethylflurazepam	1,4-benzodiazepinone; monofluorobenzenes; organochlorine compound; primary amino compound	anticonvulsant; anxiolytic drug; drug metabolite; GABAA receptor agonist; sedative	low
mecysteine	L-cysteinyl ester; primary amino compound; thiol	mucolytic	low
2,6-diaminopurine	2,6-diaminopurines; primary amino compound	antineoplastic agent	low
st 1059	aromatic ether; primary amino compound; secondary alcohol	alpha-adrenergic agonist; sympathomimetic agent; vasoconstrictor agent	low
3-morpholinopropylamine	morpholines; primary amino compound		low
oseltamivir	acetamides; amino acid ester; cyclohexenecarboxylate ester; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; environmental contaminant; prodrug; xenobiotic	low
4-methoxybenzylamine	aralkylamino compound; aromatic ether; primary amino compound		low
5-aminofluorescein	primary amino compound		low
3-methylthiopropylamine	organic sulfide; primary amino compound		low
4-phenylbutylamine	benzenes; phenylalkylamine; primary amino compound		low
caldopentamine	polyazaalkane; primary amino compound; secondary amino compound	marine metabolite	low
aclonifen	aromatic ether; C-nitro compound; monochlorobenzenes; primary amino compound; substituted aniline	agrochemical; carotenoid biosynthesis inhibitor; EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor; herbicide	low
3-aminopropylphosphonic acid	phosphonic acids; primary amino compound; zwitterion	GABAB receptor agonist	low
1-amino-1-phenylmethyl phosphonic acid	benzenes; phosphonic acids; primary amino compound		low
fingolimod	aminodiol; primary amino compound	antineoplastic agent; CB1 receptor antagonist; immunosuppressive agent; prodrug; sphingosine-1-phosphate receptor agonist	low
tafenoquine	(trifluoromethyl)benzenes; aminoquinoline; aromatic ether; primary amino compound; secondary amino compound		low
chrysobactin	catechols; dipeptide; monocarboxylic acid; primary alcohol; primary amino compound	bacterial metabolite; siderophore	low
cki 7	isoquinolines; organochlorine compound; primary amino compound; sulfonamide	EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
7-aminocholesterol	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; cholestanoid; primary amino compound	antibacterial agent	low
tyramine o-sulfate	aryl sulfate; primary amino compound; zwitterion	human urinary metabolite; human xenobiotic metabolite	low
thiobenzyl benzyloxycarbonyl-l-lysinate	benzyl ester; carbamate ester; L-lysine derivative; primary amino compound; thiocarboxylic ester		low
tipifarnib	imidazoles; monochlorobenzenes; primary amino compound; quinolone	antineoplastic agent; apoptosis inducer; EC 2.5.1.58 (protein farnesyltransferase) inhibitor	low
o 129	primary amino compound; pteridines	antifolate; vibriostatic agent	low
dopamine quinone	1,2-benzoquinones; primary amino compound	metabolite	low
n(beta)-alanyldopamine	catechols; primary amino compound; secondary carboxamide		low
5-hydroxykynuramine	hydroxykynurenamine; primary amino compound	mouse metabolite	low
s-adenosyl-3-thiopropylamine	organic sulfide; primary amino compound; thioadenosine		low
aspartimide	dicarboximide; primary amino compound; pyrrolidinone	Maillard reaction product	low
monoacetylcadaverine	acetamides; N-substituted cadaverine; primary amino compound; secondary carboxamide	human metabolite	low
8-amino-8-demethylriboflavin	aromatic amine; benzopteridine; primary amino compound; tetrol		low
nsc 23766	aminopyrimidine; aminoquinoline; primary amino compound; secondary amino compound; tertiary amino compound	antiviral agent; apoptosis inducer; EC 3.6.5.2 (small monomeric GTPase) inhibitor; muscarinic antagonist	low
paromamine	aminoglycoside; primary amino compound; triamine		low
phenylalaninol	amino alcohol; amphetamines; primary alcohol; primary amino compound		low
n(1)-guanyl-1,7-diaminoheptane	guanidines; primary amino compound	antineoplastic agent; EC 2.5.1.46 (deoxyhypusine synthase) inhibitor	low
gs 4071	acetate ester; amino acid; cyclohexenecarboxylic acid; primary amino compound	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; marine xenobiotic metabolite	low
iFSP1	aromatic amine; nitrile; primary amino compound; pyridobenzimidazole; toluenes	antineoplastic agent; ferroptosis inducer; ferroptosis suppressor protein 1 inhibitor	low
huperzine a	organic heterotricyclic compound; primary amino compound; pyridone; sesquiterpene alkaloid	EC 3.1.1.7 (acetylcholinesterase) inhibitor; neuroprotective agent; nootropic agent; plant metabolite	low
alpha-acetyllysine methyl ester	acetamides; alpha-amino acid ester; L-lysine derivative; methyl ester; primary amino compound		low
fumonisin b1	diester; fumonisin; primary amino compound; triol	carcinogenic agent; metabolite	low
fumonisin b2	diester; diol; fumonisin; primary amino compound	Aspergillus metabolite; carcinogenic agent	low
amrubicin	anthracycline antibiotic; methyl ketone; primary amino compound; quinone; tetracenes	antineoplastic agent; prodrug; topoisomerase II inhibitor	low
2-nitro-4-phenylenediamine	C-nitro compound; primary amino compound		low
1,2-diamino-4-nitrobenzene	C-nitro compound; primary amino compound		low
ro 60-0175	indoles; organochlorine compound; organofluorine compound; primary amino compound		low
pibutidine	aromatic ether; cyclobutenones; olefinic compound; piperidines; primary amino compound; pyridines; secondary amino compound	anti-ulcer drug; H2-receptor antagonist	low
fortimicin a	amino cyclitol glycoside; aminoglycoside antibiotic; diol; monocarboxylic acid amide; primary amino compound	antibacterial agent; metabolite	low
a 77636	adamantanes; catechols; isochromenes; primary amino compound	antiparkinson drug; dopamine agonist	low
b 43	aromatic amine; aromatic ether; cyclopentanes; primary amino compound; pyrrolopyrimidine	EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; geroprotector	low
nepicastat	1,3-dihydroimidazole-2-thiones; organofluorine compound; primary amino compound; tetralins	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor	low
l 779976	benzimidazoles; indoles; piperidinecarboxamide; primary amino compound; secondary carboxamide	neuroprotective agent; somatostatin receptor agonist	low
fty 720p	monoalkyl phosphate; primary alcohol; primary amino compound	antineoplastic agent; immunosuppressive agent; sphingosine-1-phosphate receptor agonist	low
pateamine a	1,3-thiazoles; macrodiolide; olefinic compound; primary amino compound; tertiary amino compound	antineoplastic agent; antiviral agent; eukaryotic initiation factor 4F inhibitor; marine metabolite	low
er-086526	cyclic ketal; cyclic ketone; macrocycle; polycyclic ether; polyether; primary amino compound	antineoplastic agent; microtubule-destabilising agent	low
alogliptin	nitrile; piperidines; primary amino compound; pyrimidines	EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; hypoglycemic agent	low
5-(5-nitrothiazol-2-ylthio)-1,3,4-thiadiazol-2-amine	1,3-thiazoles; C-nitro compound; organic sulfide; primary amino compound; thiadiazoles	antibacterial agent; c-Jun N-terminal kinase inhibitor	low
gsk690693	1,2,5-oxadiazole; acetylenic compound; aromatic amine; aromatic ether; imidazopyridine; piperidines; primary amino compound; tertiary alcohol	antineoplastic agent; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor	low
SL-327	(trifluoromethyl)benzenes; enamine; nitrile; organic sulfide; primary amino compound; substituted aniline	EC 2.7.12.2 (mitogen-activated protein kinase kinase) inhibitor; neuroprotective agent	low
lucitanib	aromatic ether; cyclopropanes; naphthalenecarboxamide; primary amino compound; quinolines	antineoplastic agent; fibroblast growth factor receptor antagonist; vascular endothelial growth factor receptor antagonist	low
fumonisin b4	diester; fumonisin; primary amino compound; secondary alcohol	Aspergillus metabolite	low
ML240	aromatic amine; aromatic ether; benzimidazoles; primary amino compound; quinazolines; secondary amino compound	antineoplastic agent	low
torin 2	aminopyridine; organofluorine compound; primary amino compound; pyridoquinoline	antineoplastic agent; mTOR inhibitor	low
crambescidin 800	alkaloid; carboxylic ester; guanidines; monocarboxylic acid amide; organic heteropentacyclic compound; primary amino compound; secondary alcohol; spiro compound	anti-HIV-1 agent; anti-HSV-1 agent; antimalarial; marine metabolite	low
as 1842856	organofluorine compound; primary amino compound; quinolinemonocarboxylic acid; quinolone; secondary amino compound; tertiary amino compound	anti-obesity agent; antineoplastic agent; apoptosis inducer; autophagy inhibitor; forkhead box protein O1 inhibitor; hypoglycemic agent	low

Substance	Classes	Roles	Relationship Strength
fentanyl	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic	low
meperidine	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	low
proglumide	benzamides; dicarboxylic acid monoamide; glutamine derivative; racemate	anti-ulcer drug; cholecystokinin antagonist; cholinergic antagonist; delta-opioid receptor agonist; drug metabolite; gastrointestinal drug; opioid analgesic; xenobiotic metabolite	low
meperidine hydrochloride	hydrochloride	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	low
anileridine	ethyl ester; piperidinecarboxylate ester; substituted aniline	opioid analgesic; opioid receptor agonist	low
dextropropoxyphene	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic	low
noramidopyrine	pyrazoles; secondary amino compound	antipyretic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; opioid analgesic; peripheral nervous system drug	low
fentanyl citrate	citrate salt	mu-opioid receptor agonist; opioid analgesic	low
levomethadone	6-(dimethylamino)-4,4-diphenylheptan-3-one	antitussive; mu-opioid receptor agonist; NMDA receptor antagonist; opioid analgesic	low
tramadol	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor	low
sufentanil	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic	low
alfentanil	monocarboxylic acid amide; piperidines	central nervous system depressant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; peripheral nervous system drug	low
remifentanil	alpha-amino acid ester; anilide; monocarboxylic acid amide; piperidinecarboxylate ester	intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; sedative	low
3-methylfentanyl	monocarboxylic acid amide; piperidines	mu-opioid receptor agonist; opioid analgesic; sedative	low
carfentanil	methyl ester; piperidines; tertiary amino compound; tertiary carboxamide	mu-opioid receptor agonist; opioid analgesic; tranquilizing drug	low
tramadol hydrochloride	hydrochloride	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor	low
dextromoramide	morpholines; N-acylpyrrolidine	opioid analgesic	low
ecgonine methyl ester	methyl ester; tertiary amino compound; tropane alkaloid	analgesic; central nervous system depressant; metabolite; mouse metabolite; opioid analgesic; peripheral nervous system drug	low
eseroline	phenols; pyrroloindole	human xenobiotic metabolite; opioid analgesic	low
lofentanil	methyl ester; piperidines; tertiary amino compound; tertiary carboxamide	mu-opioid receptor agonist; opioid analgesic	low
norfentanyl	anilide; monocarboxylic acid amide; piperidines	drug metabolite; opioid analgesic	low
dextromethadone	6-(dimethylamino)-4,4-diphenylheptan-3-one	NMDA receptor antagonist; opioid analgesic	low
buprenorphine	morphinane alkaloid	delta-opioid receptor antagonist; kappa-opioid receptor antagonist; mu-opioid receptor agonist; opioid analgesic	low
etorphine	alcohol; morphinane alkaloid	opioid analgesic; opioid receptor agonist; sedative	low
codeine	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic	low
hydrocodone	morphinane-like compound; organic heteropentacyclic compound	antitussive; mu-opioid receptor agonist; opioid analgesic	low
hydromorphone	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic	low
oxycodone	organic heteropentacyclic compound; semisynthetic derivative	antitussive; mu-opioid receptor agonist; opioid analgesic	low
morphine	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic	low
nalbuphine	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic	low
pholcodine	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; mu-opioid receptor agonist; opioid analgesic	low
butorphanol	morphinane alkaloid	antitussive; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	low
oripavine	ether; morphinane alkaloid; organic heteropentacyclic compound; organic hydroxy compound; tertiary amino compound	bacterial xenobiotic metabolite; opioid analgesic	low
heroin	morphinane alkaloid	mu-opioid receptor agonist; opioid analgesic; prodrug	low
jwh-133	benzochromene; dibenzopyran; organic heterotricyclic compound	analgesic; anti-inflammatory agent; antineoplastic agent; apoptosis inhibitor; CB2 receptor agonist; opioid analgesic; vasodilator agent	low

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
eseroline	0	phenols; pyrroloindole	human xenobiotic metabolite; opioid analgesic	0	0		low	0	0	0	0	0	0

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	2000's
bupropion	1	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
aminocaproic acid	1	amino acid zwitterion; epsilon-amino acid; omega-amino fatty acid	antifibrinolytic drug; hematologic agent; metabolite	2004	2004	20.0	low	1
phenytoin	1	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent	2004	2004	20.0	low	1
tacrine	1	acridines; aromatic amine	EC 3.1.1.7 (acetylcholinesterase) inhibitor	2004	2004	20.0	low	1
acebutolol	1	aromatic amide; ethanolamines; ether; monocarboxylic acid amide; propanolamine; secondary amino compound	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympathomimetic agent	2004	2004	20.0	low	1
acetaminophen	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	2004	2004	20.0	low	1
acetohydroxamic acid	1	acetohydroxamic acids; carbohydroximic acid	algal metabolite; EC 3.5.1.5 (urease) inhibitor	2004	2004	20.0	low	1
albuterol	1	phenols; phenylethanolamines; secondary amino compound	beta-adrenergic agonist; bronchodilator agent; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
alendronate	1	1,1-bis(phosphonic acid); primary amino compound	bone density conservation agent; EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor	2004	2004	20.0	low	1
alprazolam	1	organochlorine compound; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA agonist; muscle relaxant; sedative; xenobiotic	2004	2004	20.0	low	1
altretamine	1	triamino-1,3,5-triazine		2004	2004	20.0	low	1
amantadine	1	adamantanes; primary aliphatic amine	analgesic; antiparkinson drug; antiviral drug; dopaminergic agent; NMDA receptor antagonist; non-narcotic analgesic	2004	2004	20.0	low	1
amifostine anhydrous	1	diamine; organic thiophosphate	antioxidant; prodrug; radiation protective agent	2004	2004	20.0	low	1
aminoglutethimide	1	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor	2004	2004	20.0	low	1
theophylline	1	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent	2004	2004	20.0	low	1
amiodarone	1	1-benzofurans; aromatic ketone; organoiodine compound; tertiary amino compound	cardiovascular drug	2004	2004	20.0	low	1
amitriptyline	1	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic	2004	2004	20.0	low	1
amlexanox	1	monocarboxylic acid; pyridochromene	anti-allergic agent; anti-ulcer drug; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
amlodipine	1	dihydropyridine; ethyl ester; methyl ester; monochlorobenzenes; primary amino compound	antihypertensive agent; calcium channel blocker; vasodilator agent	2004	2004	20.0	low	1
amoxapine	1	dibenzooxazepine	adrenergic uptake inhibitor; antidepressant; dopaminergic antagonist; geroprotector; serotonin uptake inhibitor	2004	2004	20.0	low	1
anastrozole	1	nitrile; triazoles	antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor	2004	2004	20.0	low	1
apraclonidine	1	dichlorobenzene; guanidines; imidazolines	alpha-adrenergic agonist; antiglaucoma drug; beta-adrenergic agonist; diagnostic agent; ophthalmology drug	2004	2004	20.0	low	1
aspirin	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent	2004	2004	20.0	low	1
astemizole	1	benzimidazoles; piperidines	anti-allergic agent; anticoronaviral agent; H1-receptor antagonist	2004	2004	20.0	low	1
atenolol	1	ethanolamines; monocarboxylic acid amide; propanolamine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; sympatholytic agent; xenobiotic	2004	2004	20.0	low	1
azathioprine	1	aryl sulfide; C-nitro compound; imidazoles; thiopurine	antimetabolite; antineoplastic agent; carcinogenic agent; DNA synthesis inhibitor; hepatotoxic agent; immunosuppressive agent; prodrug	2004	2004	20.0	low	1
azelaic acid	1	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	antibacterial agent; antineoplastic agent; dermatologic drug; plant metabolite	2004	2004	20.0	low	1
azelastine	1	monochlorobenzenes; phthalazines; tertiary amino compound	anti-allergic agent; anti-asthmatic drug; bronchodilator agent; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; H1-receptor antagonist; platelet aggregation inhibitor	2004	2004	20.0	low	1
baclofen	1	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant	2004	2004	20.0	low	1
bepridil	1	pyrrolidines; tertiary amine	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent	2004	2004	20.0	low	1
betaxolol	1	propanolamine	antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent	2004	2004	20.0	low	1
bicalutamide	1	(trifluoromethyl)benzenes; monocarboxylic acid amide; monofluorobenzenes; nitrile; sulfone; tertiary alcohol		2004	2004	20.0	low	1
bisoprolol	1	secondary alcohol; secondary amine	anti-arrhythmia drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent	2004	2004	20.0	low	1
brimonidine	1	imidazoles; quinoxaline derivative; secondary amine	adrenergic agonist; alpha-adrenergic agonist; antihypertensive agent	2004	2004	20.0	low	1
bumetanide	1	amino acid; benzoic acids; sulfonamide	diuretic; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor	2004	2004	20.0	low	1
buspirone	1	azaspiro compound; N-alkylpiperazine; N-arylpiperazine; organic heteropolycyclic compound; piperidones; pyrimidines	anxiolytic drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; sedative; serotonergic agonist	2004	2004	20.0	low	1
busulfan	1	methanesulfonate ester	alkylating agent; antineoplastic agent; carcinogenic agent; insect sterilant; teratogenic agent	2004	2004	20.0	low	1
butenafine	1	naphthalenes; tertiary amine	antifungal drug; EC 1.14.13.132 (squalene monooxygenase) inhibitor	2004	2004	20.0	low	1
verapamil	1	aromatic ether; nitrile; polyether; tertiary amino compound		2004	2004	20.0	low	1
carbamazepine	1	dibenzoazepine; ureas	analgesic; anticonvulsant; antimanic drug; drug allergen; EC 3.5.1.98 (histone deacetylase) inhibitor; environmental contaminant; glutamate transporter activator; mitogen; non-narcotic analgesic; sodium channel blocker; xenobiotic	2004	2004	20.0	low	1
carmustine	1	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent	2004	2004	20.0	low	1
carteolol	1	quinolone; secondary alcohol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; sympatholytic agent	2004	2004	20.0	low	1
carvedilol	1	carbazoles; secondary alcohol; secondary amino compound	alpha-adrenergic antagonist; antihypertensive agent; beta-adrenergic antagonist; cardiovascular drug; vasodilator agent	2004	2004	20.0	low	1
cetirizine	1	ether; monocarboxylic acid; monochlorobenzenes; piperazines	anti-allergic agent; environmental contaminant; H1-receptor antagonist; xenobiotic	2004	2004	20.0	low	1
chlormezanone	1	1,3-thiazine; lactam; monochlorobenzenes; sulfone	antipsychotic agent; anxiolytic drug; muscle relaxant	2004	2004	20.0	low	1
ciclopirox	1	cyclic hydroxamic acid; hydroxypyridone antifungal drug; pyridone	antibacterial agent; antiseborrheic	2004	2004	20.0	low	1
cinoxacin	1	cinnolines; oxacycle; oxo carboxylic acid	antibacterial drug; antiinfective agent	2004	2004	20.0	low	1
ciprofloxacin	1	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic	2004	2004	20.0	low	1
cisapride	1	benzamides		2004	2004	20.0	low	1
clofazimine	1	monochlorobenzenes; phenazines	dye; leprostatic drug; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
clomipramine	1	dibenzoazepine	anticoronaviral agent; antidepressant; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; serotonergic antagonist; serotonergic drug; serotonin uptake inhibitor	2004	2004	20.0	low	1
clonidine	1	clonidine; imidazoline		2004	2004	20.0	low	1
chlorazepate	1	1,4-benzodiazepinone	anticonvulsant; anxiolytic drug; GABA modulator; prodrug	2004	2004	20.0	medium	1
cyclobenzaprine	1	carbotricyclic compound	antidepressant; muscle relaxant; tranquilizing drug	2004	2004	20.0	low	1
diazepam	1	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic	2004	2004	20.0	low	1
diclofenac	1	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic	2004	2004	20.0	low	1
diflunisal	1	monohydroxybenzoic acid; organofluorine compound	non-narcotic analgesic; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
dipivefrin	1	ethanolamines; pivalate ester	adrenergic agonist; antiglaucoma drug; ophthalmology drug; prodrug; sympathomimetic agent	2004	2004	20.0	low	1
disopyramide	1	monocarboxylic acid amide; pyridines; tertiary amino compound	anti-arrhythmia drug	2004	2004	20.0	low	1
disulfiram	1	organic disulfide; organosulfur acaricide	angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor	2004	2004	20.0	low	1
valproic acid	1	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent	2004	2004	20.0	low	1
doxazosin	1	aromatic amine; benzodioxine; monocarboxylic acid amide; N-acylpiperazine; N-arylpiperazine; quinazolines	alpha-adrenergic antagonist; antihyperplasia drug; antihypertensive agent; antineoplastic agent; vasodilator agent	2004	2004	20.0	low	1
doxepin	1	dibenzooxepine; tertiary amino compound	antidepressant	2004	2004	20.0	low	1
droperidol	1	aromatic ketone; benzimidazoles; organofluorine compound	anaesthesia adjuvant; antiemetic; dopaminergic antagonist; first generation antipsychotic	2004	2004	20.0	low	1
econazole	1	dichlorobenzene; ether; imidazoles; monochlorobenzenes		2004	2004	20.0	low	1
enflurane	1	ether; organochlorine compound; organofluorine compound	anaesthetic	2004	2004	20.0	low	1
enoxacin	1	1,8-naphthyridine derivative; amino acid; fluoroquinolone antibiotic; monocarboxylic acid; N-arylpiperazine; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor	2004	2004	20.0	low	1
estazolam	1	triazoles; triazolobenzodiazepine	anticonvulsant; anxiolytic drug; GABA modulator	2004	2004	20.0	low	1
etidronate	1	1,1-bis(phosphonic acid)	antineoplastic agent; bone density conservation agent; chelator	2004	2004	20.0	low	1
etodolac	1	monocarboxylic acid; organic heterotricyclic compound	antipyretic; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
brl 42810	1	2-aminopurines; acetate ester	antiviral drug; prodrug	2004	2004	20.0	low	1
felbamate	1	carbamate ester	anticonvulsant; neuroprotective agent	2004	2004	20.0	low	1
felodipine	1	dichlorobenzene; dihydropyridine; ethyl ester; methyl ester	anti-arrhythmia drug; antihypertensive agent; calcium channel blocker; vasodilator agent	2004	2004	20.0	low	1
fenfluramine	1	(trifluoromethyl)benzenes; secondary amino compound	appetite depressant; serotonergic agonist; serotonin uptake inhibitor	2004	2004	20.0	low	1
fentanyl	1	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic	2004	2004	20.0	low	1
fexofenadine	1	piperidines; tertiary amine	anti-allergic agent; H1-receptor antagonist	2004	2004	20.0	low	1
flecainide	1	aromatic ether; monocarboxylic acid amide; organofluorine compound; piperidines	anti-arrhythmia drug	2004	2004	20.0	low	1
fluconazole	1	conazole antifungal drug; difluorobenzene; tertiary alcohol; triazole antifungal drug	environmental contaminant; P450 inhibitor; xenobiotic	2004	2004	20.0	low	1
flucytosine	1	aminopyrimidine; nucleoside analogue; organofluorine compound; pyrimidine antifungal drug; pyrimidone	prodrug	2004	2004	20.0	low	1
fluphenazine	1	N-alkylpiperazine; organofluorine compound; phenothiazines	anticoronaviral agent; dopaminergic antagonist; phenothiazine antipsychotic drug	2004	2004	20.0	low	1
flumazenil	1	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist	2004	2004	20.0	low	1
fluorouracil	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic	2004	2004	20.0	low	1
fluoxetine	1	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound		2004	2004	20.0	low	1
fluphenazine depot	1	decanoate ester; N-alkylpiperazine; organofluorine compound; phenothiazines	dopaminergic antagonist; phenothiazine antipsychotic drug; prodrug	2004	2004	20.0	low	1
fluphenazine enanthate	1	phenothiazines		2004	2004	20.0	low	1
flurbiprofen	1	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
flutamide	1	(trifluoromethyl)benzenes; monocarboxylic acid amide	androgen antagonist; antineoplastic agent	2004	2004	20.0	low	1
foscarnet	1	carboxylic acid; one-carbon compound; phosphonic acids	antiviral drug; geroprotector; HIV-1 reverse transcriptase inhibitor; sodium-dependent Pi-transporter inhibitor	2004	2004	20.0	low	1
furosemide	1	chlorobenzoic acid; furans; sulfonamide	environmental contaminant; loop diuretic; xenobiotic	2004	2004	20.0	low	1
gabapentin	1	gamma-amino acid	anticonvulsant; calcium channel blocker; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
gemfibrozil	1	aromatic ether	antilipemic drug	2004	2004	20.0	low	1
glimepiride	1	sulfonamide		2004	2004	20.0	low	1
glipizide	1	aromatic amide; monocarboxylic acid amide; N-sulfonylurea; pyrazines	EC 2.7.1.33 (pantothenate kinase) inhibitor; hypoglycemic agent; insulin secretagogue	2004	2004	20.0	low	1
glyburide	1	monochlorobenzenes; N-sulfonylurea	anti-arrhythmia drug; EC 2.7.1.33 (pantothenate kinase) inhibitor; EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor; hypoglycemic agent	2004	2004	20.0	low	1
granisetron	1	aromatic amide; indazoles		2004	2004	20.0	low	1
guanfacine	1	acetamides		2004	2004	20.0	low	1
haloperidol	1	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist	2004	2004	20.0	low	1
halothane	1	haloalkane; organobromine compound; organochlorine compound; organofluorine compound	inhalation anaesthetic	2004	2004	20.0	low	1
hydrochlorothiazide	1	benzothiadiazine; organochlorine compound; sulfonamide	antihypertensive agent; diuretic; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
hydroxyurea	1	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent	2004	2004	20.0	low	1
hydroxyzine	1	hydroxyether; monochlorobenzenes; N-alkylpiperazine	anticoronaviral agent; antipruritic drug; anxiolytic drug; dermatologic drug; H1-receptor antagonist	2004	2004	20.0	low	1
ibuprofen	1	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic	2004	2004	20.0	low	1
phenelzine	1	primary amine		2004	2004	20.0	low	1
ifosfamide	1	ifosfamides	alkylating agent; antineoplastic agent; environmental contaminant; immunosuppressive agent; xenobiotic	2004	2004	20.0	low	1
amrinone	1	bipyridines	EC 3.1.4.* (phosphoric diester hydrolase) inhibitor	2004	2004	20.0	low	1
indapamide	1	indoles; organochlorine compound; sulfonamide	antihypertensive agent; diuretic	2004	2004	20.0	low	1
indomethacin	1	aromatic ether; indole-3-acetic acids; monochlorobenzenes; N-acylindole	analgesic; drug metabolite; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; gout suppressant; non-steroidal anti-inflammatory drug; xenobiotic metabolite; xenobiotic	2004	2004	20.0	low	1
iodixanol	1	organoiodine compound	radioopaque medium	2004	2004	20.0	low	1
iohexol	1	benzenedicarboxamide; organoiodine compound	environmental contaminant; radioopaque medium; xenobiotic	2004	2004	20.0	low	1
iopromide	1	dicarboxylic acid diamide; organoiodine compound	environmental contaminant; nephrotoxic agent; radioopaque medium; xenobiotic	2004	2004	20.0	low	1
ioversol	1	amidobenzoic acid		2004	2004	20.0	low	1
isoflurane	1	organofluorine compound	inhalation anaesthetic	2004	2004	20.0	low	1
isoniazid	1	carbohydrazide	antitubercular agent; drug allergen	2004	2004	20.0	low	1
isradipine	1	benzoxadiazole; dihydropyridine; isopropyl ester; methyl ester		2004	2004	20.0	low	1
itraconazole	1	piperazines		2004	2004	20.0	low	1
ketoconazole	1	dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine		2004	2004	20.0	low	1
ketoprofen	1	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic	2004	2004	20.0	low	1
ketorolac	1	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
labetalol	1	benzamides; benzenes; phenols; primary carboxamide; salicylamides; secondary alcohol; secondary amino compound		2004	2004	20.0	low	1
lamotrigine	1	1,2,4-triazines; dichlorobenzene; primary arylamine	anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic	2004	2004	20.0	low	1
lansoprazole	1	benzimidazoles; pyridines; sulfoxide	anti-ulcer drug; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor	2004	2004	20.0	low	1
lomefloxacin	1	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antimicrobial agent; antitubercular agent; photosensitizing agent	2004	2004	20.0	low	1
loratadine	1	benzocycloheptapyridine; ethyl ester; N-acylpiperidine; organochlorine compound; tertiary carboxamide	anti-allergic agent; cholinergic antagonist; geroprotector; H1-receptor antagonist	2004	2004	20.0	low	1
losartan	1	biphenylyltetrazole; imidazoles	angiotensin receptor antagonist; anti-arrhythmia drug; antihypertensive agent; endothelin receptor antagonist	2004	2004	20.0	low	1
loxapine	1	dibenzooxazepine	antipsychotic agent; dopaminergic antagonist	2004	2004	20.0	low	1
maprotiline	1	anthracenes		2004	2004	20.0	low	1
mebendazole	1	aromatic ketone; benzimidazoles; carbamate ester	antinematodal drug; microtubule-destabilising agent; tubulin modulator	2004	2004	20.0	low	1
meclofenamic acid	1	aminobenzoic acid; organochlorine compound; secondary amino compound	analgesic; anticonvulsant; antineoplastic agent; antipyretic; antirheumatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
mefenamic acid	1	aminobenzoic acid; secondary amino compound	analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic	2004	2004	20.0	low	1
mefloquine hydrochloride	1	organofluorine compound; piperidines; quinolines; secondary alcohol		2004	2004	20.0	low	1
meperidine	1	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	2009	2009	15.0	low	1
mesalamine	1	amino acid; aromatic amine; monocarboxylic acid; monohydroxybenzoic acid; phenols	non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
metformin	1	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic	2004	2004	20.0	low	1
metoclopramide	1	benzamides; monochlorobenzenes; substituted aniline; tertiary amino compound	antiemetic; dopaminergic antagonist; environmental contaminant; gastrointestinal drug; xenobiotic	2004	2004	20.0	low	1
metoprolol	1	aromatic ether; propanolamine; secondary alcohol; secondary amino compound	antihypertensive agent; beta-adrenergic antagonist; environmental contaminant; geroprotector; xenobiotic	2004	2004	20.0	low	1
metronidazole	1	C-nitro compound; imidazoles; primary alcohol	antiamoebic agent; antibacterial drug; antimicrobial agent; antiparasitic agent; antitrichomonal drug; environmental contaminant; prodrug; radiosensitizing agent; xenobiotic	2004	2004	20.0	low	1
mexiletine	1	aromatic ether; primary amino compound	anti-arrhythmia drug	2004	2004	20.0	low	1
midazolam	1	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative	2004	2004	20.0	low	1
midodrine	1	amino acid amide; aromatic ether; secondary alcohol	alpha-adrenergic agonist; prodrug; sympathomimetic agent; vasoconstrictor agent	2004	2004	20.0	low	1
minoxidil	1	dialkylarylamine; tertiary amino compound		2004	2004	20.0	low	1
mirtazapine	1	benzazepine; tetracyclic antidepressant	alpha-adrenergic antagonist; anxiolytic drug; H1-receptor antagonist; histamine antagonist; oneirogen; serotonergic antagonist	2004	2004	20.0	low	1
mitoxantrone	1	dihydroxyanthraquinone	analgesic; antineoplastic agent	2004	2004	20.0	low	1
nabumetone	1	methoxynaphthalene; methyl ketone	cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug	2004	2004	20.0	low	1
nefazodone	1	aromatic ether; monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazoles	alpha-adrenergic antagonist; analgesic; antidepressant; serotonergic antagonist; serotonin uptake inhibitor	2004	2004	20.0	low	1
nevirapine	1	cyclopropanes; dipyridodiazepine	antiviral drug; HIV-1 reverse transcriptase inhibitor	2004	2004	20.0	low	1
nicardipine	1	benzenes; C-nitro compound; diester; dihydropyridine; methyl ester; tertiary amino compound		2004	2004	20.0	low	1
nifedipine	1	C-nitro compound; dihydropyridine; methyl ester	calcium channel blocker; human metabolite; tocolytic agent; vasodilator agent	2004	2004	20.0	low	1
nilutamide	1	(trifluoromethyl)benzenes; C-nitro compound; imidazolidinone	androgen antagonist; antineoplastic agent	2004	2004	20.0	low	1
nimodipine	1	2-methoxyethyl ester; C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; isopropyl ester	antihypertensive agent; calcium channel blocker; cardiovascular drug; vasodilator agent	2004	2004	20.0	low	1
nisoldipine	1	C-nitro compound; dicarboxylic acids and O-substituted derivatives; diester; dihydropyridine; methyl ester		2004	2004	20.0	low	1
nizatidine	1	1,3-thiazoles; C-nitro compound; carboxamidine; organic sulfide; tertiary amino compound	anti-ulcer drug; cholinergic drug; H2-receptor antagonist	2004	2004	20.0	low	1
masoprocol	1	catechols; lignan; tetrol	antioxidant; ferroptosis inhibitor; geroprotector; plant metabolite	2004	2004	20.0	low	1
norfloxacin	1	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone	antibacterial drug; DNA synthesis inhibitor; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
nortriptyline	1	organic tricyclic compound; secondary amine	adrenergic uptake inhibitor; analgesic; antidepressant; antineoplastic agent; apoptosis inducer; drug metabolite	2004	2004	20.0	low	1
ofloxacin	1	3-oxo monocarboxylic acid; N-arylpiperazine; N-methylpiperazine; organofluorine compound; oxazinoquinoline		2004	2004	20.0	low	1
omeprazole	1	aromatic ether; benzimidazoles; pyridines; sulfoxide		2004	2004	20.0	low	1
ondansetron	1	carbazoles		2004	2004	20.0	low	1
oxaprozin	1	1,3-oxazoles; monocarboxylic acid	analgesic; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
pamidronate	1	phosphonoacetic acid		2004	2004	20.0	low	1
pemoline	1	1,3-oxazoles	central nervous system stimulant	2004	2004	20.0	low	1
pentamidine	1	aromatic ether; carboxamidine; diether	anti-inflammatory agent; antifungal agent; calmodulin antagonist; chemokine receptor 5 antagonist; EC 2.3.1.48 (histone acetyltransferase) inhibitor; NMDA receptor antagonist; S100 calcium-binding protein B inhibitor; trypanocidal drug; xenobiotic	2004	2004	20.0	low	1
pentoxifylline	1	oxopurine		2004	2004	20.0	low	1
perphenazine	1	N-(2-hydroxyethyl)piperazine; N-alkylpiperazine; organochlorine compound; phenothiazines	antiemetic; dopaminergic antagonist; phenothiazine antipsychotic drug	2004	2004	20.0	low	1
pindolol	1	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent	2004	2004	20.0	low	1
pirbuterol	1	pyridines		2004	2004	20.0	low	1
prazepam	1	benzodiazepine		2004	2004	20.0	low	1
praziquantel	1	isoquinolines		2004	2004	20.0	low	1
prazosin	1	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor	2004	2004	20.0	low	1
primidone	1	pyrimidone	anticonvulsant; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
probenecid	1	benzoic acids; sulfonamide	uricosuric drug	2004	2004	20.0	low	1
procainamide	1	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker	2004	2004	20.0	low	1
procarbazine	1	benzamides; hydrazines	antineoplastic agent	2004	2004	20.0	low	1
propafenone	1	aromatic ketone; secondary alcohol; secondary amino compound	anti-arrhythmia drug	2004	2004	20.0	low	1
propofol	1	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative	2004	2004	20.0	low	1
sch 16134	1	benzodiazepine		2004	2004	20.0	low	1
ranitidine	1	aralkylamine		2004	2004	20.0	low	1
riluzole	1	benzothiazoles		2004	2004	20.0	low	1
rimantadine	1	alkylamine		2004	2004	20.0	low	1
risperidone	1	1,2-benzoxazoles; heteroarylpiperidine; organofluorine compound; pyridopyrimidine	alpha-adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; H1-receptor antagonist; psychotropic drug; second generation antipsychotic; serotonergic antagonist	2004	2004	20.0	low	1
salmeterol xinafoate	1	ether; phenols; primary alcohol; secondary alcohol; secondary amino compound		2004	2004	20.0	low	1
sevoflurane	1	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor	2004	2004	20.0	low	1
sulfadiazine	1	pyrimidines; substituted aniline; sulfonamide antibiotic; sulfonamide	antiinfective agent; antimicrobial agent; antiprotozoal drug; coccidiostat; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
sotalol	1	ethanolamines; secondary alcohol; secondary amino compound; sulfonamide	anti-arrhythmia drug; beta-adrenergic antagonist; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
sulconazole	1	dichlorobenzene; imidazoles; monochlorobenzenes; organic sulfide		2004	2004	20.0	low	1
sulfasalazine	1			2004	2004	20.0	low	1
sumatriptan	1	sulfonamide; tryptamines	serotonergic agonist; vasoconstrictor agent	2004	2004	20.0	low	1
suprofen	1	aromatic ketone; monocarboxylic acid; thiophenes	antirheumatic drug; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; peripheral nervous system drug	2004	2004	20.0	low	1
tazarotene	1	acetylenic compound; ethyl ester; pyridines; retinoid; thiochromane	keratolytic drug; prodrug; teratogenic agent	2004	2004	20.0	low	1
temazepam	1	benzodiazepine		2004	2004	20.0	low	1
terazosin	1	furans; piperazines; primary amino compound; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; antineoplastic agent	2004	2004	20.0	low	1
terfenadine	1	diarylmethane		2004	2004	20.0	low	1
thioridazine	1	phenothiazines; piperidines	alpha-adrenergic antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist	2004	2004	20.0	low	1
thiotepa	1	aziridines		2004	2004	20.0	low	1
ticlopidine	1	monochlorobenzenes; thienopyridine	anticoagulant; fibrin modulating drug; hematologic agent; P2Y12 receptor antagonist; platelet aggregation inhibitor	2004	2004	20.0	low	1
tioconazole	1	dichlorobenzene; ether; imidazoles; thiophenes		2004	2004	20.0	low	1
tiopronin	1	N-acyl-amino acid		2004	2004	20.0	low	1
tizanidine	1	benzothiadiazole; imidazoles	alpha-adrenergic agonist; muscle relaxant	2004	2004	20.0	low	1
ultram	1	aromatic ether; tertiary alcohol; tertiary amino compound		2004	2004	20.0	low	1
trazodone	1	monochlorobenzenes; N-alkylpiperazine; N-arylpiperazine; triazolopyridine	adrenergic antagonist; antidepressant; anxiolytic drug; H1-receptor antagonist; sedative; serotonin uptake inhibitor	2004	2004	20.0	low	1
triazolam	1	triazolobenzodiazepine	sedative	2004	2004	20.0	low	1
trientine	1	polyazaalkane; tetramine	copper chelator	2004	2004	20.0	low	1
trifluoperazine	1	N-alkylpiperazine; N-methylpiperazine; organofluorine compound; phenothiazines	antiemetic; calmodulin antagonist; dopaminergic antagonist; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor; phenothiazine antipsychotic drug	2004	2004	20.0	low	1
trimethadione	1	oxazolidinone	anticonvulsant; geroprotector	2004	2004	20.0	low	1
trimetrexate	1			2004	2004	20.0	low	1
trimipramine	1	dibenzoazepine; tertiary amino compound	antidepressant; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
venlafaxine	1	cyclohexanols; monomethoxybenzene; tertiary alcohol; tertiary amino compound	adrenergic uptake inhibitor; analgesic; antidepressant; dopamine uptake inhibitor; environmental contaminant; serotonin uptake inhibitor; xenobiotic	2004	2004	20.0	low	1
ici 204,219	1	carbamate ester; indoles; N-sulfonylcarboxamide	anti-asthmatic agent; leukotriene antagonist	2004	2004	20.0	low	1
zolpidem	1	imidazopyridine	central nervous system depressant; GABA agonist; sedative	2004	2004	20.0	low	1
zomepirac	1	aromatic ketone; monocarboxylic acid; monochlorobenzenes; pyrroles	cardiovascular drug; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
floxuridine	1	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent	2004	2004	20.0	low	1
spironolactone	1	3-oxo-Delta(4) steroid; oxaspiro compound; steroid lactone; thioester	aldosterone antagonist; antihypertensive agent; diuretic; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
penicillamine	1	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen	2004	2004	20.0	low	1
prednisone	1	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug	2004	2004	20.0	low	1
pilocarpine	1	pilocarpine	antiglaucoma drug	2004	2004	20.0	low	1
vincristine	1	acetate ester; formamides; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent; drug; microtubule-destabilising agent; plant metabolite; tubulin modulator	2004	2004	20.0	low	1
testosterone propionate	1	steroid ester		2004	2004	20.0	low	1
bretylium tosylate	1	organosulfonate salt; quaternary ammonium salt	adrenergic antagonist; anti-arrhythmia drug; antihypertensive agent	2004	2004	20.0	low	1
cytarabine	1	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent	2004	2004	20.0	low	1
trifluridine	1	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; EC 2.1.1.45 (thymidylate synthase) inhibitor	2004	2004	20.0	low	1
medroxyprogesterone acetate	1	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; corticosteroid; steroid ester	adjuvant; androgen; antineoplastic agent; antioxidant; female contraceptive drug; inhibitor; progestin; synthetic oral contraceptive	2004	2004	20.0	low	1
mestranol	1	17beta-hydroxy steroid; aromatic ether; terminal acetylenic compound	prodrug; xenoestrogen	2004	2004	20.0	low	1
methylprednisolone	1	6-methylprednisolone; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antiemetic; environmental contaminant; neuroprotective agent; xenobiotic	2004	2004	20.0	low	1
estradiol dipropionate	1	steroid ester		2004	2004	20.0	low	1
nafcillin	1	penicillin allergen; penicillin	antibacterial drug	2004	2004	20.0	low	1
methohexital	1	acetylenic compound; barbiturates	drug allergen; intravenous anaesthetic	2004	2004	20.0	low	1
estradiol 17 beta-cypionate	1	steroid ester		2004	2004	20.0	low	1
testosterone enanthate	1	heptanoate ester; sterol ester	androgen	2004	2004	20.0	low	1
betamethasone	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic agent; anti-inflammatory drug; immunosuppressive agent	2004	2004	20.0	low	1
chenodeoxycholic acid	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite	2004	2004	20.0	low	1
podophyllotoxin	1	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator	2004	2004	20.0	low	1
levocarnitine	1	carnitine	antilipemic drug; nootropic agent; nutraceutical; Saccharomyces cerevisiae metabolite; water-soluble vitamin (role)	2004	2004	20.0	low	1
megestrol acetate	1	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; steroid ester	antineoplastic agent; appetite enhancer; contraceptive drug; progestin; synthetic oral contraceptive	2004	2004	20.0	low	1
acetylcysteine	1	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	2004	2004	20.0	low	1
erythromycin	1	cyclic ketone; erythromycin		2004	2004	20.0	low	1
levonorgestrel	1	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin; synthetic oral contraceptive	2004	2004	20.0	low	1
estradiol valerate	1	steroid ester		2004	2004	20.0	low	1
ethambutol	1	ethanolamines; ethylenediamine derivative	antitubercular agent; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
dronabinol	1	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic	2004	2004	20.0	low	1
pimozide	1	benzimidazoles; heteroarylpiperidine; organofluorine compound	antidyskinesia agent; dopaminergic antagonist; first generation antipsychotic; H1-receptor antagonist; serotonergic antagonist	2004	2004	20.0	low	1
betamethasone valerate	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; primary alpha-hydroxy ketone; steroid ester	anti-inflammatory drug	2004	2004	20.0	low	1
methylprednisolone hemisuccinate	1	corticosteroid hormone; hemisuccinate		2004	2004	20.0	low	1
stavudine	1	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor	2004	2004	20.0	low	1
cyclacillin	1	penicillin	antibacterial drug	2004	2004	20.0	low	1
tranylcypromine	1	2-phenylcyclopropan-1-amine		2004	2004	20.0	low	1
cladribine	1	organochlorine compound; purine 2'-deoxyribonucleoside	antineoplastic agent; immunosuppressive agent	2004	2004	20.0	low	1
beclomethasone	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; corticosteroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	anti-asthmatic drug; anti-inflammatory drug	2004	2004	20.0	low	1
estradiol enanthate	1	steroid ester		2004	2004	20.0	low	1
betamethasone-17,21-dipropionate	1	11beta-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; fluorinated steroid; propanoate ester; steroid ester	antipsoriatic	2004	2004	20.0	low	1
olsalazine	1	azobenzenes; dicarboxylic acid	non-steroidal anti-inflammatory drug; prodrug	2004	2004	20.0	low	1
zalcitabine	1	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor	2004	2004	20.0	low	1
selegiline	1	selegiline; terminal acetylenic compound	geroprotector	2004	2004	20.0	low	1
levamisole	1	6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole	antinematodal drug; antirheumatic drug; EC 3.1.3.1 (alkaline phosphatase) inhibitor; immunological adjuvant; immunomodulator	2004	2004	20.0	low	1
cephalexin	1	beta-lactam antibiotic allergen; cephalosporin; semisynthetic derivative	antibacterial drug	2004	2004	20.0	low	1
isosorbide-5-mononitrate	1	glucitol derivative; nitrate ester	nitric oxide donor; vasodilator agent	2004	2004	20.0	low	1
danazol	1	17beta-hydroxy steroid; terminal acetylenic compound	anti-estrogen; estrogen antagonist; geroprotector	2004	2004	20.0	low	1
daunorubicin	1	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite	2004	2004	20.0	low	1
cephapirin	1	cephalosporin	antibacterial drug	2004	2004	20.0	low	1
bromocriptine	1	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist	2004	2004	20.0	low	1
ursodeoxycholic acid	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human metabolite; mouse metabolite	2004	2004	20.0	low	1
metipranolol	1	acetate ester; aromatic ether; propanolamine; secondary amino compound	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist	2004	2004	20.0	low	1
halazepam	1	organic molecular entity		2004	2004	20.0	low	1
du-21220	1	benzyl alcohols; polyphenol; secondary alcohol; secondary amino compound		2004	2004	20.0	low	1
cefazolin	1	beta-lactam antibiotic allergen; cephalosporin; tetrazoles; thiadiazoles	antibacterial drug	2004	2004	20.0	low	1
amoxicillin	1	penicillin allergen; penicillin	antibacterial drug	2004	2004	20.0	low	1
timolol	1	timolol	anti-arrhythmia drug; antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist	2004	2004	20.0	low	1
moricizine	1	carbamate ester; morpholines; phenothiazines	anti-arrhythmia drug	2004	2004	20.0	low	1
bitolterol	1	carboxylic ester; diester; ethanolamines; secondary alcohol; secondary amino compound	anti-asthmatic drug; beta-adrenergic agonist; bronchodilator agent; prodrug	2004	2004	20.0	low	1
zidovudine	1	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor	2004	2004	20.0	low	1
tobramycin	1	amino cyclitol glycoside	antibacterial agent; antimicrobial agent; toxin	2004	2004	20.0	low	1
paclitaxel	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent	2004	2004	20.0	low	1
etoposide	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor	2004	2004	20.0	low	1
dobutamine	1	catecholamine; secondary amine	beta-adrenergic agonist; cardiotonic drug; sympathomimetic agent	2004	2004	20.0	low	1
penbutolol	1	ethanolamines		2004	2004	20.0	low	1
ribavirin	1	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor	2004	2004	20.0	low	1
guanadrel	1	guanidines; spiroketal	adrenergic antagonist; antihypertensive agent	2004	2004	20.0	low	1
methyldopa	1	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	alpha-adrenergic agonist; antihypertensive agent; hapten; peripheral nervous system drug; sympatholytic agent	2004	2004	20.0	low	1
tocainide	1	monocarboxylic acid amide	anti-arrhythmia drug; local anaesthetic; sodium channel blocker	2004	2004	20.0	low	1
sq-11725	1			2004	2004	20.0	low	1
diltiazem	1	5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate	antihypertensive agent; calcium channel blocker; vasodilator agent	2004	2004	20.0	low	1
levobunolol	1	aromatic ether; cyclic ketone; propanolamine	antiglaucoma drug; beta-adrenergic antagonist	2004	2004	20.0	low	1
vecuronium bromide	1	organic bromide salt; quaternary ammonium salt	muscle relaxant; neuromuscular agent; nicotinic antagonist	2004	2004	20.0	low	1
permethrin	1	cyclopropanecarboxylate ester; cyclopropanes	agrochemical; ectoparasiticide; pyrethroid ester acaricide; pyrethroid ester insecticide; scabicide	2004	2004	20.0	low	1
sufentanil	1	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic	2004	2004	20.0	low	1
torsemide	1	aminopyridine; N-sulfonylurea; secondary amino compound	antihypertensive agent; loop diuretic	2004	2004	20.0	low	1
cefmetazole	1	cephalosporin	antibacterial drug	2004	2004	20.0	low	1
desflurane	1	organofluorine compound	inhalation anaesthetic	2004	2004	20.0	low	1
idarubicin	1	anthracycline antibiotic; deoxy hexoside; monosaccharide derivative		2004	2004	20.0	low	1
cefonicid	1	cephalosporin	antibacterial drug	2004	2004	20.0	low	1
piperacillin	1	penicillin allergen; penicillin	antibacterial drug	2004	2004	20.0	low	1
paroxetine	1	aromatic ether; benzodioxoles; organofluorine compound; piperidines	antidepressant; anxiolytic drug; hepatotoxic agent; P450 inhibitor; serotonin uptake inhibitor	2004	2004	20.0	low	1
captopril	1	alkanethiol; L-proline derivative; N-acylpyrrolidine; pyrrolidinemonocarboxylic acid	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor	2004	2004	20.0	low	1
cefoperazone	1	cephalosporin	antibacterial drug	2004	2004	20.0	low	1
lodoxamide	1	organonitrogen compound; organooxygen compound		2004	2004	20.0	low	1
atracurium	1	diester; quaternary ammonium ion	muscle relaxant; nicotinic antagonist	2004	2004	20.0	low	1
butoconazole	1	aryl sulfide; conazole antifungal drug; dichlorobenzene; imidazole antifungal drug; imidazoles; monochlorobenzenes		2004	2004	20.0	low	1
naftifine	1	allylamine antifungal drug; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; sterol biosynthesis inhibitor	2004	2004	20.0	low	1
pergolide	1	diamine; methyl sulfide; organic heterotetracyclic compound	antiparkinson drug; dopamine agonist	2004	2004	20.0	low	1
cefadroxil anhydrous	1	cephalosporin	antibacterial drug	2004	2004	20.0	low	1
encainide	1	benzamides; piperidines	anti-arrhythmia drug; sodium channel blocker	2004	2004	20.0	low	1
nedocromil	1	dicarboxylic acid; organic heterotricyclic compound	anti-allergic agent; anti-asthmatic drug; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
cefaclor anhydrous	1	cephalosporin	antibacterial drug; drug allergen	2004	2004	20.0	low	1
alfentanil	1	monocarboxylic acid amide; piperidines	central nervous system depressant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; peripheral nervous system drug	2004	2004	20.0	low	1
cefotetan	1			2004	2004	20.0	low	1
lovastatin	1	delta-lactone; fatty acid ester; hexahydronaphthalenes; polyketide; statin (naturally occurring)	anticholesteremic drug; antineoplastic agent; Aspergillus metabolite; prodrug	2004	2004	20.0	low	1
levocabastine	1	piperidines		2004	2004	20.0	low	1
simvastatin	1	delta-lactone; fatty acid ester; hexahydronaphthalenes; statin (semi-synthetic)	EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor; EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor; ferroptosis inducer; geroprotector; prodrug	2004	2004	20.0	low	1
pravastatin	1	3-hydroxy carboxylic acid; carbobicyclic compound; carboxylic ester; hydroxy monocarboxylic acid; secondary alcohol; statin (semi-synthetic)	anticholesteremic drug; environmental contaminant; metabolite; xenobiotic	2004	2004	20.0	low	1
cabergoline	1	N-acylurea	antineoplastic agent; antiparkinson drug; dopamine agonist	2004	2004	20.0	low	1
quinapril	1	dicarboxylic acid monoester; ethyl ester; isoquinolines; tertiary carboxamide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug	2004	2004	20.0	low	1
fosphenytoin	1	imidazolidine-2,4-dione		2004	2004	20.0	low	1
finasteride	1	3-oxo steroid; aza-steroid; delta-lactam	androgen antagonist; antihyperplasia drug; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor	2004	2004	20.0	low	1
esmolol	1	aromatic ether; ethanolamines; methyl ester; secondary alcohol; secondary amino compound		2004	2004	20.0	low	1
adapalene	1	adamantanes; monocarboxylic acid; naphthoic acid	dermatologic drug; EC 2.7.11.22 (cyclin-dependent kinase) inhibitor; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
sparfloxacin	1	fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone		2004	2004	20.0	low	1
zileuton	1	1-benzothiophenes; ureas	anti-asthmatic drug; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; ferroptosis inhibitor; leukotriene antagonist; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
cidofovir anhydrous	1	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent	2004	2004	20.0	low	1
topotecan	1	pyranoindolizinoquinoline	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor	2004	2004	20.0	low	1
gemcitabine	1	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic	2004	2004	20.0	low	1
ibutilide	1	benzenes; organic amino compound		2004	2004	20.0	low	1
remifentanil	1	alpha-amino acid ester; anilide; monocarboxylic acid amide; piperidinecarboxylate ester	intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; sedative	2004	2004	20.0	low	1
atorvastatin	1	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic	2004	2004	20.0	low	1
lamivudine	1	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug	2004	2004	20.0	low	1
irinotecan	1	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	2004	2004	20.0	low	1
valsartan	1	biphenylyltetrazole; monocarboxylic acid amide; monocarboxylic acid	angiotensin receptor antagonist; antihypertensive agent; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
adenosine	1	adenosines; purines D-ribonucleoside	analgesic; anti-arrhythmia drug; fundamental metabolite; human metabolite; vasodilator agent	2004	2004	20.0	low	1
cefprozil	1	cephalosporin; semisynthetic derivative	antibacterial drug	2004	2004	20.0	medium	1
methylprednisolone aceponate	1	corticosteroid hormone		2004	2004	20.0	low	1
dexamethasone 17-valerate	1	21-hydroxy steroid		2004	2004	20.0	low	1
dexamethasone dipropionate	1	corticosteroid hormone		2004	2004	20.0	low	1
iopamidol	1	benzenedicarboxamide; organoiodine compound; pentol	environmental contaminant; radioopaque medium; xenobiotic	2004	2004	20.0	low	1
dexfenfluramine	1	fenfluramine	appetite depressant; serotonergic agonist; serotonin uptake inhibitor	2004	2004	20.0	low	1
sertraline	1	dichlorobenzene; secondary amino compound; tetralins	antidepressant; serotonin uptake inhibitor	2004	2004	20.0	low	1
erythromycin propionate	1	erythromycin derivative		2004	2004	20.0	low	1
dexrazoxane	1	razoxane	antineoplastic agent; cardiovascular drug; chelator; immunosuppressive agent	2004	2004	20.0	low	1
antebate	1	corticosteroid hormone		2004	2004	20.0	low	1
atovaquone	1	hydroxy-1,2-naphthoquinone		2004	2004	20.0	low	1
flunisolide	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic ketal; fluorinated steroid; primary alpha-hydroxy ketone	anti-asthmatic drug; anti-inflammatory drug; immunosuppressive agent	2004	2004	20.0	low	1
clarithromycin	1	macrolide antibiotic	antibacterial drug; environmental contaminant; protein synthesis inhibitor; xenobiotic	2004	2004	20.0	low	1
nicotine	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic	2004	2004	20.0	low	1
moexipril	1	peptide		2004	2004	20.0	low	1
methotrexate	1	dicarboxylic acid; monocarboxylic acid amide; pteridines	abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent	2004	2004	20.0	low	1
docetaxel	1	hydrate; secondary alpha-hydroxy ketone	antineoplastic agent	2004	2004	20.0	low	1
levofloxacin	1	9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid; fluoroquinolone antibiotic; quinolone antibiotic	antibacterial drug; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; topoisomerase IV inhibitor	2004	2004	20.0	low	1
naproxen	1	methoxynaphthalene; monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic	2004	2004	20.0	low	1
ropivacaine	1	piperidinecarboxamide; ropivacaine	local anaesthetic	2004	2004	20.0	low	1
estradiol 3-benzoate	1	17beta-hydroxy steroid; benzoate ester	estrogen receptor agonist; xenoestrogen	2004	2004	20.0	low	1
estramustine	1	17beta-hydroxy steroid; carbamate ester; organochlorine compound	alkylating agent; antineoplastic agent; radiation protective agent	2004	2004	20.0	low	1
ritonavir	1	1,3-thiazoles; carbamate ester; carboxamide; L-valine derivative; ureas	antiviral drug; environmental contaminant; HIV protease inhibitor; xenobiotic	2004	2004	20.0	low	1
pentostatin	1	coformycins	antimetabolite; antineoplastic agent; Aspergillus metabolite; bacterial metabolite; EC 3.5.4.4 (adenosine deaminase) inhibitor	2004	2004	20.0	low	1
quinidine	1	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker	2004	2004	20.0	low	1
meropenem	1	alpha,beta-unsaturated monocarboxylic acid; carbapenemcarboxylic acid; organic sulfide; pyrrolidinecarboxamide	antibacterial agent; antibacterial drug; drug allergen	2004	2004	20.0	low	1
griseofulvin	1	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite	2004	2004	20.0	low	1
cefoxitin	1	beta-lactam antibiotic allergen; cephalosporin; cephamycin; semisynthetic derivative	antibacterial drug	2004	2004	20.0	low	1
saquinavir	1	L-asparagine derivative; quinolines	antiviral drug; HIV protease inhibitor	2004	2004	20.0	low	1
netilmicin	1			2004	2004	20.0	low	1
metyrosine	1	L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	antihypertensive agent; EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor	2004	2004	20.0	low	1
rocuronium bromide	1	organic bromide salt; quaternary ammonium salt	muscle relaxant; neuromuscular agent	2004	2004	20.0	high	1
terconazole	1	1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine		2004	2004	20.0	low	1
bacampicillin	1	penicillanic acid ester	prodrug	2004	2004	20.0	low	1
erythromycin ethylsuccinate	1	cyclic ketone; erythromycin derivative; ethyl ester; succinate ester		2004	2004	20.0	low	1
amcinonide	1	11beta-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; acetate ester; corticosteroid; fluorinated steroid; spiroketal	anti-inflammatory drug	2004	2004	20.0	low	1
betamethasone acetate	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; acetate ester; fluorinated steroid; steroid ester; tertiary alpha-hydroxy ketone		2004	2004	20.0	low	1
acarbose	1	amino cyclitol; glycoside		2004	2004	20.0	low	1
tretinoin	1	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule	2004	2004	20.0	low	1
mycophenolic acid	1	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic	2004	2004	20.0	low	1
mupirocin	1	alpha,beta-unsaturated carboxylic ester; epoxide; monocarboxylic acid; oxanes; secondary alcohol; triol	antibacterial drug; bacterial metabolite; protein synthesis inhibitor	2004	2004	20.0	low	1
fosfomycin	1	epoxide; phosphonic acids	antimicrobial agent; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor	2004	2004	20.0	low	1
zithromax	1	macrolide antibiotic	antibacterial drug; environmental contaminant; xenobiotic	2004	2004	20.0	low	1
teniposide	1	aromatic ether; beta-D-glucoside; cyclic acetal; furonaphthodioxole; gamma-lactone; monosaccharide derivative; phenols; thiophenes	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor	2004	2004	20.0	low	1
cefamandole	1	cephalosporin; semisynthetic derivative	antibacterial drug	2004	2004	20.0	low	1
dactinomycin	1	actinomycin	mutagen	2004	2004	20.0	low	1
melphalan	1	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent	2004	2004	20.0	low	1
sch 22219	1	11beta-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; glucocorticoid; propanoate ester; steroid ester	anti-inflammatory drug	2004	2004	20.0	low	1
mezlocillin	1	penicillin allergen; penicillin	antibacterial drug	2004	2004	20.0	low	1
cholinophyllin	1			2004	2004	20.0	low	1
fludarabine	1	purine nucleoside		2004	2004	20.0	low	1
propylthiouracil	1	pyrimidinethione	antidote to paracetamol poisoning; antimetabolite; antioxidant; antithyroid drug; carcinogenic agent; EC 1.14.13.39 (nitric oxide synthase) inhibitor; hormone antagonist	2004	2004	20.0	low	1
ipratropium bromide anhydrous	1			2004	2004	20.0	low	1
etomidate	1	ethyl ester; imidazoles	intravenous anaesthetic; sedative	2004	2004	20.0	low	1
mercaptopurine	1	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent	2004	2004	20.0	low	1
thiothixene	1	N-methylpiperazine	anticoronaviral agent	2004	2004	20.0	low	1
benztropine	1	diarylmethane		2004	2004	20.0	low	1
sulindac	1	monocarboxylic acid; organofluorine compound; sulfoxide	analgesic; antineoplastic agent; antipyretic; apoptosis inducer; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug; prodrug; tocolytic agent	2004	2004	20.0	low	1
enclomiphene	1			2004	2004	20.0	low	1
terbinafine	1	acetylenic compound; allylamine antifungal drug; enyne; naphthalenes; tertiary amine	EC 1.14.13.132 (squalene monooxygenase) inhibitor; P450 inhibitor; sterol biosynthesis inhibitor	2004	2004	20.0	low	1
thioguanine anhydrous	1	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent	2004	2004	20.0	low	1
succimer	1	dicarboxylic acid; dithiol; sulfur-containing carboxylic acid	chelator	2004	2004	20.0	low	1
streptozocin	1			2004	2004	20.0	low	1
tamoxifen	1	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator	2004	2004	20.0	low	1
ethionamide	1	pyridines; thiocarboxamide	antilipemic drug; antitubercular agent; fatty acid synthesis inhibitor; leprostatic drug; prodrug	2004	2004	20.0	low	1
dapiprazole	1	N-alkylpiperazine; N-arylpiperazine; pyridines	alpha-adrenergic antagonist; antipsychotic agent; miotic; ophthalmology drug	2004	2004	20.0	low	1
flosequinan	1	quinolines		2004	2004	20.0	low	1
calcitriol	1	D3 vitamins; hydroxycalciol; triol	antineoplastic agent; antipsoriatic; bone density conservation agent; calcium channel agonist; calcium channel modulator; hormone; human metabolite; immunomodulator; metabolite; mouse metabolite; nutraceutical	2004	2004	20.0	low	1
alprostadil	1	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent	2004	2004	20.0	low	1
amphotericin b	1	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite	2004	2004	20.0	low	1
pulmicort	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic acetal; glucocorticoid; primary alpha-hydroxy ketone	anti-inflammatory drug; bronchodilator agent; drug allergen	2004	2004	20.0	low	1
olopatadine	1			2004	2004	20.0	medium	1
bw b1090u	1	isoquinolines		2004	2004	20.0	high	1
7432 s	1	cephalosporin; dicarboxylic acid	antibacterial drug	2004	2004	20.0	low	1
etretinate	1	enoate ester; ethyl ester; retinoid	keratolytic drug	2004	2004	20.0	low	1
isotretinoin	1	retinoic acid	antineoplastic agent; keratolytic drug; teratogenic agent	2004	2004	20.0	low	1
misoprostol	1			2004	2004	20.0	low	1
epoprostenol	1	prostaglandins I	mouse metabolite	2004	2004	20.0	low	1
betamethasone benzoate	1	21-hydroxy steroid		2004	2004	20.0	medium	1
dorzolamide	1	sulfonamide; thiophenes	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor	2004	2004	20.0	low	1
hydromorphone	1	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic	2004	2004	20.0	low	1
ly 163892	1	carbacephem; zwitterion	antibacterial drug; antimicrobial agent	2004	2004	20.0	low	1
nalmefene	1	morphinane alkaloid		2004	2004	20.0	low	1
topiramate	1	cyclic ketal; ketohexose derivative; sulfamate ester	anticonvulsant; sodium channel blocker	2004	2004	20.0	low	1
calcipotriene	1	cyclopropanes; hydroxy seco-steroid; seco-cholestane; secondary alcohol; triol	antipsoriatic; drug allergen	2004	2004	20.0	medium	1
clobetasol	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; chlorinated steroid; fluorinated steroid; glucocorticoid; tertiary alpha-hydroxy ketone	anti-inflammatory drug; SMO receptor agonist	2004	2004	20.0	low	1
fluticasone	1	11beta-hydroxy steroid; 17alpha-hydroxy steroid; 3-oxo-Delta(4) steroid; corticosteroid; fluorinated steroid; thioester	anti-allergic agent; anti-asthmatic drug	2004	2004	20.0	low	1
halobetasol	1	corticosteroid hormone		2004	2004	20.0	low	1
latanoprost	1	isopropyl ester; prostaglandins Falpha; triol	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor; prodrug	2004	2004	20.0	low	1
nalbuphine	1	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic	2004	2004	20.0	low	1
rimexolone	1	20-oxo steroid		2004	2004	20.0	low	1
vinorelbine	1	acetate ester; methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; ring assembly; vinca alkaloid	antineoplastic agent; photosensitizing agent	2004	2004	20.0	low	1
fluvoxamine	1	(trifluoromethyl)benzenes; 5-methoxyvalerophenone O-(2-aminoethyl)oxime	antidepressant; anxiolytic drug; serotonin uptake inhibitor	2004	2004	20.0	low	1
(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid	1	dihydroxy monocarboxylic acid; indoles; organofluorine compound		2004	2004	20.0	low	1
oxiconazole	1	conazole antifungal drug; dichlorobenzene; imidazole antifungal drug; imidazoles; oxime O-ether	antiinfective agent	2004	2004	20.0	low	1
naltrexone	1	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic	2004	2004	20.0	low	1
butorphanol	1	morphinane alkaloid	antitussive; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	2004	2004	20.0	low	1
cefixime	1	cephalosporin	antibacterial drug; drug allergen	2004	2004	20.0	low	1
lisinopril	1	dipeptide	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor	2004	2004	20.0	low	1
benazepril	1	benzazepine; dicarboxylic acid monoester; ethyl ester; lactam	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug	2004	2004	20.0	low	1
ramipril	1	azabicycloalkane; cyclopentapyrrole; dicarboxylic acid monoester; dipeptide; ethyl ester	bradykinin receptor B2 agonist; cardioprotective agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; matrix metalloproteinase inhibitor; prodrug	2004	2004	20.0	low	1
indinavir sulfate	1	dicarboxylic acid diamide; N-(2-hydroxyethyl)piperazine; piperazinecarboxamide	HIV protease inhibitor	2004	2004	20.0	low	1
enalapril	1	dicarboxylic acid monoester; dipeptide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; geroprotector; prodrug	2004	2004	20.0	low	1
cefuroxime	1	3-(carbamoyloxymethyl)cephalosporin; furans; oxime O-ether	drug allergen	2004	2004	20.0	low	1
ceftriaxone	1	1,2,4-triazines; 1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen; EC 3.5.2.6 (beta-lactamase) inhibitor	2004	2004	20.0	low	1
cefepime	1	cephalosporin; oxime O-ether	antibacterial drug	2004	2004	20.0	low	1
ceftazidime	1	cephalosporin; oxime O-ether	antibacterial drug; drug allergen; EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor	2004	2004	20.0	low	1
trandolapril	1	dicarboxylic acid monoester; dipeptide; ethyl ester; organic heterobicyclic compound; secondary amino compound; tertiary carboxamide	antihypertensive agent; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; prodrug	2004	2004	20.0	low	1
guanabenz	1	dichlorobenzene		2004	2004	20.0	low	1
famotidine	1	1,3-thiazoles; guanidines; sulfonamide	anti-ulcer drug; H2-receptor antagonist; P450 inhibitor	2004	2004	20.0	low	1
cefotaxime	1	1,3-thiazoles; cephalosporin; oxime O-ether	antibacterial drug; drug allergen	2004	2004	20.0	low	1
aztreonam	1	beta-lactam antibiotic allergen; monobactam	antibacterial drug; drug allergen; EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor	2004	2004	20.0	low	1
cci 15641	1	cephalosporin		2004	2004	20.0	medium	1
cefpodoxime	1	carboxylic acid; cephalosporin	antibacterial drug	2004	2004	20.0	low	1
dirithromycin	1	macrolide antibiotic	prodrug	2004	2004	20.0	low	1
cefpodoxime proxetil	1	carboxylic acid; carboxylic ester; cephalosporin	antibacterial drug; prodrug	2004	2004	20.0	low	1
ceftizoxime	1	cephalosporin	antibacterial drug	2004	2004	20.0	low	1
nitrofurantoin	1	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent	2004	2004	20.0	low	1
dantrolene	1			2004	2004	20.0	low	1
fosinopril	1			2004	2004	20.0	medium	1
nystatin a1	1	nystatins		2004	2004	20.0	low	1
mesna	1	organosulfonic acid		2004	2004	20.0	low	1
cefamandole nafate	1	organic sodium salt	antibacterial drug; prodrug	2004	2004	20.0	medium	1
tetracycline	1			2004	2004	20.0	low	1
minocycline	1			2004	2004	20.0	low	1
piroxicam	1	benzothiazine; monocarboxylic acid amide; pyridines	analgesic; antirheumatic drug; cyclooxygenase 1 inhibitor; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug	2004	2004	20.0	low	1
meclocycline	1			2004	2004	20.0	low	1
warfarin	1	benzenes; hydroxycoumarin; methyl ketone		2004	2004	20.0	low	1
acyclovir	1	2-aminopurines; oxopurine	antimetabolite; antiviral drug	2004	2004	20.0	low	1
rifampin	1	cyclic ketal; hydrazone; N-iminopiperazine; N-methylpiperazine; rifamycins; semisynthetic derivative; zwitterion	angiogenesis inhibitor; antiamoebic agent; antineoplastic agent; antitubercular agent; DNA synthesis inhibitor; EC 2.7.7.6 (RNA polymerase) inhibitor; Escherichia coli metabolite; geroprotector; leprostatic drug; neuroprotective agent; pregnane X receptor agonist; protein synthesis inhibitor	2004	2004	20.0	low	1
clozapine	1	benzodiazepine; N-arylpiperazine; N-methylpiperazine; organochlorine compound	adrenergic antagonist; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; GABA antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; xenobiotic	2004	2004	20.0	low	1
didanosine	1	purine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor; geroprotector; HIV-1 reverse transcriptase inhibitor	2004	2004	20.0	low	1
ganciclovir	1	2-aminopurines; oxopurine	antiinfective agent; antiviral drug	2004	2004	20.0	low	1
valacyclovir	1	L-valyl ester	antiviral drug	2004	2004	20.0	low	1
olanzapine	1	benzodiazepine; N-arylpiperazine; N-methylpiperazine	antiemetic; dopaminergic antagonist; histamine antagonist; muscarinic antagonist; second generation antipsychotic; serotonergic antagonist; serotonin uptake inhibitor	2004	2004	20.0	low	1
penciclovir	1	2-aminopurines; propane-1,3-diols	antiviral drug	2004	2004	20.0	low	1
allopurinol	1	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger	2004	2004	20.0	low	1
rifabutin	1			2004	2004	20.0	low	1

Substance	Studies	Classes	Roles	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
histamine	1	aralkylamino compound; imidazoles	human metabolite; mouse metabolite; neurotransmitter	1981	1981	43.0	low	0	1	0	0	0	0
7-hydroxy-2-n,n-dipropylaminotetralin	1	tetralins		1999	1999	25.0	low	0	0	1	0	0	0
sk&f-38393	1	benzazepine; catechols; secondary amino compound		1999	1999	25.0	low	0	0	1	0	0	0
aspirin	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent	2019	2019	5.0	low	0	0	0	0	1	0
celecoxib	1	organofluorine compound; pyrazoles; sulfonamide; toluenes	cyclooxygenase 2 inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug	2021	2021	3.0	low	0	0	0	0	0	1
diclofenac	1	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic	2019	2019	5.0	low	0	0	0	0	1	0
enflurane	1	ether; organochlorine compound; organofluorine compound	anaesthetic	1987	1987	37.0	low	0	1	0	0	0	0
fentanyl	10	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic	1992	2021	16.9	low	7	0	4	0	5	1
flurbiprofen	2	fluorobiphenyl; monocarboxylic acid	antipyretic; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug	2014	2021	6.5	low	2	0	0	0	1	1
fp 83	2	organic molecular entity		2014	2021	6.5	low	2	0	0	0	1	1
lidocaine	3	benzenes; monocarboxylic acid amide; tertiary amino compound	anti-arrhythmia drug; drug allergen; environmental contaminant; local anaesthetic; xenobiotic	2019	2023	2.7	low	1	0	0	0	1	2
ketamine	1	cyclohexanones; monochlorobenzenes; secondary amino compound	analgesic; environmental contaminant; intravenous anaesthetic; neurotoxin; NMDA receptor antagonist; xenobiotic	2022	2022	2.0	low	1	0	0	0	0	1
ketorolac	4	amino acid; aromatic ketone; monocarboxylic acid; pyrrolizines; racemate	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; non-steroidal anti-inflammatory drug	1992	2022	23.5	low	3	0	3	0	0	1
meperidine	2	ethyl ester; piperidinecarboxylate ester; tertiary amino compound	antispasmodic drug; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	1979	2001	34.0	low	1	1	0	1	0	0
midazolam	3	imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative	2015	2020	7.0	low	1	0	0	0	3	0
propofol	8	phenols	anticonvulsant; antiemetic; intravenous anaesthetic; radical scavenger; sedative	1995	2023	7.5	low	5	0	1	0	3	4
sevoflurane	3	ether; organofluorine compound	central nervous system depressant; inhalation anaesthetic; platelet aggregation inhibitor	2015	2017	7.7	low	2	0	0	0	3	0
spiperone	1	aromatic ketone; azaspiro compound; organofluorine compound; piperidines; tertiary amino compound	alpha-adrenergic antagonist; antipsychotic agent; dopaminergic antagonist; psychotropic drug; serotonergic antagonist	1999	1999	25.0	low	0	0	1	0	0	0
tolmetin	3	aromatic ketone; monocarboxylic acid; pyrroles	EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; non-steroidal anti-inflammatory drug	1992	1995	30.7	low	2	0	3	0	0	0
cyclopropane	1	cycloalkane; cyclopropanes	inhalation anaesthetic	1983	1983	41.0	low	0	1	0	0	0	0
cyclohexanol	1	cyclohexanols; secondary alcohol	solvent	1981	1981	43.0	low	0	1	0	0	0	0
diphenhydramine hydrochloride	1	hydrochloride; organoammonium salt	anti-allergic agent; antiemetic; antiparkinson drug; antipruritic drug; H1-receptor antagonist; local anaesthetic; muscarinic antagonist; sedative	2017	2017	7.0	low	1	0	0	0	1	0
dextropropoxyphene	1	1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate	mu-opioid receptor agonist; opioid analgesic	2001	2001	23.0	low	0	0	0	1	0	0
propiram	1	pyridines		1984	1984	40.0	medium	0	1	0	0	0	0
etorphine	2			2000	2000	24.0	low	0	0	2	0	0	0
tramadol	1	2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol	adrenergic uptake inhibitor; antitussive; capsaicin receptor antagonist; delta-opioid receptor agonist; kappa-opioid receptor agonist; metabolite; mu-opioid receptor agonist; muscarinic antagonist; nicotinic antagonist; NMDA receptor antagonist; opioid analgesic; serotonergic antagonist; serotonin uptake inhibitor	2018	2018	6.0	low	0	0	0	0	1	0
substance p	1	peptide	neurokinin-1 receptor agonist; neurotransmitter; vasodilator agent	1989	1989	35.0	low	0	1	0	0	0	0
sufentanil	11	anilide; ether; piperidines; thiophenes	anaesthesia adjuvant; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic	2015	2022	5.1	low	8	0	0	0	7	4
enkephalin, methionine	1			1989	1989	35.0	low	0	1	0	0	0	0
ciramadol	4	cyclohexanols		1981	1989	38.8	medium	1	4	0	0	0	0
quinpirole	1	pyrazoloquinoline	dopamine agonist	1999	1999	25.0	low	0	0	1	0	0	0
remifentanil	5	alpha-amino acid ester; anilide; monocarboxylic acid amide; piperidinecarboxylate ester	intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic; sedative	2017	2022	4.4	low	3	0	0	0	4	1
ketorolac tromethamine	1	organoammonium salt	analgesic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor	2022	2022	2.0	low	1	0	0	0	0	1
1-hydroxymethylmidazolam	1	aromatic primary alcohol; imidazobenzodiazepine; monofluorobenzenes; organochlorine compound	drug metabolite; human blood serum metabolite; human urinary metabolite	2020	2020	4.0	low	0	0	0	0	1	0
ramosetron	2	indoles		2018	2022	4.0	low	1	0	0	0	1	1
ly 274614	2			2000	2008	20.0	low	0	0	1	1	0	0
ropivacaine	3	piperidinecarboxamide; ropivacaine	local anaesthetic	2020	2022	3.3	low	2	0	0	0	2	1
esketamine	1	ketamine	analgesic; intravenous anaesthetic; NMDA receptor antagonist	2022	2022	2.0	low	1	0	0	0	0	1
pentazocine	2	benzazocine		1981	2021	23.0	low	0	1	0	0	0	1
cocaine	1	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic	2001	2001	23.0	low	0	0	0	1	0	0
flavin-adenine dinucleotide	1	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group	2021	2021	3.0	low	1	0	0	0	0	1
buprenorphine	7	morphinane alkaloid	delta-opioid receptor antagonist; kappa-opioid receptor antagonist; mu-opioid receptor agonist; opioid analgesic	1984	2019	24.0	low	0	2	2	2	1	0
tropisetron	1	indolyl carboxylic acid		2018	2018	6.0	low	0	0	0	0	1	0
etomidate	3	ethyl ester; imidazoles	intravenous anaesthetic; sedative	2014	2017	8.7	low	2	0	0	0	3	0
capsaicin	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker	2003	2003	21.0	low	0	0	0	1	0	0
nadp	1			2022	2022	2.0	low	0	0	0	0	0	1
u-50488	1	dichlorobenzene; monocarboxylic acid amide; N-alkylpyrrolidine	analgesic; antitussive; calcium channel blocker; diuretic; kappa-opioid receptor agonist	2021	2021	3.0	low	0	0	0	0	0	1
codeine	1	morphinane alkaloid; organic heteropentacyclic compound	antitussive; drug allergen; environmental contaminant; opioid analgesic; opioid receptor agonist; prodrug; xenobiotic	2019	2019	5.0	low	0	0	0	0	1	0
hydromorphone	2	morphinane alkaloid; organic heteropentacyclic compound	mu-opioid receptor agonist; opioid analgesic	1996	2018	17.0	low	2	0	1	0	1	0
naloxone	4	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist	1981	1997	34.5	low	1	2	2	0	0	0
oxycodone	2	organic heteropentacyclic compound; semisynthetic derivative	antitussive; mu-opioid receptor agonist; opioid analgesic	2016	2023	4.5	low	0	0	0	0	1	1
morphine	32	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic	1981	2021	26.5	low	10	15	6	2	8	1
beta-funaltrexamine	2	morphinane alkaloid		1997	2021	15.0	low	0	0	1	0	0	1
dexmedetomidine	9	medetomidine	alpha-adrenergic agonist; analgesic; non-narcotic analgesic; sedative	2014	2023	4.1	low	5	0	0	0	4	5
nalbuphine	8	organic heteropentacyclic compound	mu-opioid receptor antagonist; opioid analgesic	1984	2020	29.0	low	1	3	4	0	1	0
levorphanol	2	morphinane alkaloid		1999	2000	24.5	low	0	0	2	0	0	0
levallorphan	1	morphinane alkaloid		1984	1984	40.0	low	0	1	0	0	0	0
naltrexone	3	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic	1997	2021	12.0	low	0	0	1	0	1	1
oxilorphan	1			1984	1984	40.0	low	0	1	0	0	0	0
butorphanol	11	morphinane alkaloid	antitussive; kappa-opioid receptor agonist; mu-opioid receptor agonist; opioid analgesic	1984	2018	29.5	low	4	6	3	0	2	0
norbinaltorphimine	1	isoquinolines		2018	2018	6.0	low	0	0	0	0	1	0
enkephalin, ala(2)-mephe(4)-gly(5)-	1			2018	2018	6.0	low	0	0	0	0	1	0
pregabalin	1	gamma-amino acid	anticonvulsant; calcium channel blocker	2019	2019	5.0	low	0	0	0	0	1	0
morphinans	6	isoquinoline alkaloid fundamental parent; morphinane alkaloid		1984	1987	38.3	low	4	6	0	0	0	0
tapentadol	2	alkylbenzene		2020	2021	3.5	low	0	0	0	0	1	1
dynorphins	2			1989	1989	35.0	low	0	2	0	0	0	0
ziconotide	1			2019	2019	5.0	low	0	0	0	0	1	0
piperidines	1			2017	2017	7.0	low	0	0	0	0	1	0

Condition	Indicated	Studies	First Year	Last Year	Average Age	Relationship Strength	Trials	pre-1990	1990's	2000's	2010's	post-2020
Abdominal Cramps	0	2	1980	1985	41.5	low	1	2	0	0	0	0
Ache	0	15	1980	2022	16.5	low	7	3	3	0	5	4
Acute Disease	0	3	1985	1995	35.3	low	3	2	1	0	0	0
Acute Post-operative Pain	0	33	1979	2023	15.4	medium	24	9	1	0	15	8
Addiction, Opioid	0	1	1996	1996	28.0	low	1	0	1	0	0	0
Adverse Drug Event	0	1	2004	2004	20.0	low	0	0	0	1	0	0
Agitated Emergence	0	1	2017	2017	7.0	low	0	0	0	0	1	0
Agitation, Psychomotor	0	1	2017	2017	7.0	low	0	0	0	0	1	0
Allodynia	0	5	2003	2022	6.8	low	0	0	0	1	2	2
Anesthesia	0	3	1981	2017	19.3	low	2	1	0	0	2	0
Anterior Choroidal Artery Infarction	0	1	2023	2023	1.0	low	0	0	0	0	0	1
Benign Neoplasms	0	5	1980	2022	19.0	low	2	2	0	0	2	1
Blood Pressure, Low	0	1	2017	2017	7.0	low	0	0	0	0	1	0
Body Weight	0	1	1992	1992	32.0	low	0	0	1	0	0	0
Bone Cancer	0	2	2020	2021	3.5	low	0	0	0	0	1	1
Bone Neoplasms	0	2	2020	2021	3.5	low	0	0	0	0	1	1
Brain Ischemia	0	1	2023	2023	1.0	low	0	0	0	0	0	1
Breast Cancer	0	1	2021	2021	3.0	low	0	0	0	0	0	1
Breast Neoplasms	0	1	2021	2021	3.0	low	0	0	0	0	0	1
Burns	0	1	2015	2015	9.0	low	1	0	0	0	1	0
Cancer of Cervix	0	1	2016	2016	8.0	low	0	0	0	0	1	0
Cancer of Gastrointestinal Tract	0	1	2023	2023	1.0	low	1	0	0	0	0	1
Cancer of Liver	0	1	2019	2019	5.0	low	1	0	0	0	1	0
Cancer of Lung	0	4	2019	2022	2.8	low	1	0	0	0	1	3
Cancer of Stomach	0	1	2016	2016	8.0	low	0	0	0	0	1	0
Cancer Pain	0	4	2019	2022	3.5	low	0	0	0	0	2	2
Cancer-Associated Pain	0	4	2019	2022	3.5	low	0	0	0	0	2	2
Carcinoma, Hepatocellular	0	1	2019	2019	5.0	low	1	0	0	0	1	0
Cerebral Infarction	0	1	2023	2023	1.0	low	0	0	0	0	0	1
Cerebral Ischemia	0	1	2023	2023	1.0	low	0	0	0	0	0	1
Chemical Dependence	0	3	1985	1992	35.0	low	2	1	2	0	0	0
Chronic Disease	0	2	1987	1995	33.0	low	2	1	1	0	0	0
Chronic Illness	0	2	1987	1995	33.0	low	2	1	1	0	0	0
Chronic Pain	0	1	2019	2019	5.0	low	0	0	0	0	1	0
Colorectal Cancer	0	1	2020	2020	4.0	low	1	0	0	0	1	0
Colorectal Neoplasms	0	1	2020	2020	4.0	low	1	0	0	0	1	0
Complication, Intraoperative	0	1	2015	2015	9.0	low	1	0	0	0	1	0
Complication, Postoperative	0	6	2015	2020	6.3	low	3	0	0	0	6	0
Concomitant Strabismus	0	1	2014	2014	10.0	low	1	0	0	0	1	0
Cough	0	7	2011	2022	6.1	low	4	0	0	0	6	1
Degenerative Disc Disease	0	1	2022	2022	2.0	low	0	0	0	0	0	1
Depression	0	1	2020	2020	4.0	low	1	0	0	0	1	0
Disease Models, Animal	0	3	2003	2021	9.3	low	0	0	0	1	1	1
Disease, Pulmonary	0	1	2018	2018	6.0	low	1	0	0	0	1	0
Dizziness	0	1	1980	1980	44.0	low	0	1	0	0	0	0
Dizzyness	0	1	1980	1980	44.0	low	0	1	0	0	0	0
Drug-Related Side Effects and Adverse Reactions	0	1	2004	2004	20.0	low	0	0	0	1	0	0
Dyskinesia, Drug-Induced	0	1	2015	2015	9.0	low	1	0	0	0	1	0
Dyskinesia, Medication-Induced	0	1	2015	2015	9.0	low	1	0	0	0	1	0
Emesis	0	1	1986	1986	38.0	low	1	1	0	0	0	0
Emesis, Postoperative	0	2	2018	2018	6.0	low	0	0	0	0	2	0
Experimental Mammary Neoplasms	0	1	2020	2020	4.0	low	0	0	0	0	1	0
Gagging	0	1	2017	2017	7.0	low	1	0	0	0	1	0
Heart Disease, Ischemic	0	1	2020	2020	4.0	low	0	0	0	0	1	0
Hepatocellular Carcinoma	0	1	2019	2019	5.0	low	1	0	0	0	1	0
Hernia, Inguinal	0	2	2018	2022	4.0	low	2	0	0	0	1	1
Hypotension	0	1	2017	2017	7.0	low	0	0	0	0	1	0
Inflammation	0	1	1992	1992	32.0	low	0	0	1	0	0	0
Inguinal Hernia	0	2	2018	2022	4.0	low	2	0	0	0	1	1
Innate Inflammatory Response	0	1	1992	1992	32.0	low	0	0	1	0	0	0
Intervertebral Disc Degeneration	0	1	2022	2022	2.0	low	0	0	0	0	0	1
Itching	0	1	2018	2018	6.0	low	0	0	0	0	1	0
Kidney Diseases	0	2	1980	1985	41.5	low	1	2	0	0	0	0
Liver Neoplasms	0	1	2019	2019	5.0	low	1	0	0	0	1	0
Lung Diseases	0	1	2018	2018	6.0	low	1	0	0	0	1	0
Lung Neoplasms	0	4	2019	2022	2.8	low	1	0	0	0	1	3
Morphine Abuse	0	1	2019	2019	5.0	low	0	0	0	0	1	0
Morphine Dependence	0	1	2019	2019	5.0	low	0	0	0	0	1	0
Muscle Contraction	0	2	1989	2015	22.0	low	0	1	0	0	1	0
Myelopathy	0	1	1992	1992	32.0	low	0	0	1	0	0	0
Myocardial Ischemia	0	1	2020	2020	4.0	low	0	0	0	0	1	0
Myoclonic Jerk	0	3	2014	2017	8.7	low	2	0	0	0	3	0
Nausea	0	1	1986	1986	38.0	low	1	1	0	0	0	0
Neoplasms	0	5	1980	2022	19.0	low	2	2	0	0	2	1
Nerve Pain	0	2	2020	2023	2.5	low	0	0	0	0	1	1
Neuralgia	0	2	2020	2023	2.5	low	0	0	0	0	1	1
Nociceptive Pain	0	1	2021	2021	3.0	low	0	0	0	0	0	1
Opioid-Related Disorders	0	1	1996	1996	28.0	low	1	0	1	0	0	0
Pain	1	15	1980	2022	16.5	low	7	3	3	0	5	4
Pain, Chronic	0	1	2019	2019	5.0	low	0	0	0	0	1	0
Pain, Postoperative	0	33	1979	2023	15.4	medium	24	9	1	0	15	8
Peripheral Nerve Injuries	0	1	2020	2020	4.0	low	0	0	0	0	1	0
Peripheral Nerve Injury	0	1	2020	2020	4.0	low	0	0	0	0	1	0
Pharyngitis	0	1	2014	2014	10.0	low	1	0	0	0	1	0
Postoperative Complications	0	6	2015	2020	6.3	low	3	0	0	0	6	0
Postoperative Nausea and Vomiting	0	2	2018	2018	6.0	low	0	0	0	0	2	0
Pregnancy	0	2	1981	2018	24.5	low	1	1	0	0	1	0
Pruritus	0	1	2018	2018	6.0	low	0	0	0	0	1	0
Psychomotor Agitation	0	1	2017	2017	7.0	low	0	0	0	0	1	0
Recrudescence	0	1	2020	2020	4.0	low	0	0	0	0	1	0
Respiration Disorders	0	1	1984	1984	40.0	low	0	1	0	0	0	0
Retinal Diseases	0	1	2016	2016	8.0	low	1	0	0	0	1	0
Sore Throat	0	1	2014	2014	10.0	low	1	0	0	0	1	0
Spinal Cord Diseases	0	1	1992	1992	32.0	low	0	0	1	0	0	0
Stomach Neoplasms	0	1	2016	2016	8.0	low	0	0	0	0	1	0
Strabismus	0	1	2014	2014	10.0	low	1	0	0	0	1	0
Substance-Related Disorders	0	3	1985	1992	35.0	low	2	1	2	0	0	0
Ureteral Diseases	0	1	1985	1985	39.0	low	1	1	0	0	0	0
Urinary Calculi	0	1	1985	1985	39.0	low	1	1	0	0	0	0
Uterine Cervical Neoplasms	0	1	2016	2016	8.0	low	0	0	0	0	1	0
Vomiting	0	1	1986	1986	38.0	low	1	1	0	0	0	0

Safety/Toxicity (7)

Article	Year
To evaluate the efficacy and safety of dezocine combined with lidocaine in local anesthesia for percutaneous testicular sperm aspiration. Pakistan journal of pharmaceutical sciences, , Volume: 36, Issue:5	2023
[Application value and safety of prostate peripheral nerve block combined with dezocine in transrectal prostate biopsy]. Zhonghua nan ke xue = National journal of andrology, , Volume: 28, Issue:6	2022
Is dezocine effective and safe in preventing opioids-induced cough during general anaesthesia induction? A protocol for systematic review and meta-analysis. BMJ open, , 06-17, Volume: 10, Issue:6	2020
Efficacy and safety of different doses of dezocine for preemptive analgesia in gynecological laparoscopic surgeries: A prospective, double blind and randomized controlled clinical trial. International journal of surgery (London, England), , Volume: 37 Suppl 1
Comparison of the efficacy and safety between dezocine injection and morphine injection for persistence of pain in Chinese cancer patients: a meta-analysis. Bioscience reports, , Jun-30, Volume: 37, Issue:3	2017
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling. Current drug discovery technologies, , Volume: 1, Issue:4	2004
Toxicity of chronic spinal analgesia in a canine model: neuropathologic observations with dezocine lactate. Regional anesthesia, , Volume: 15, Issue:2

Pharmacokinetics (6)

Article	Year
Simultaneous Determination of Celecoxib, Dezocine and Dexmedetomidine in Beagle Plasma Using UPLC-MS/MS Method and the Application in Pharmacokinetics. Drug design, development and therapy, , Volume: 15	2021
Effects of Dexmedetomidine on the Pharmacokinetics of Dezocine, Midazolam and Its Metabolite 1-Hydroxymidazolam in Beagles by UPLC-MS/MS. Drug design, development and therapy, , Volume: 14	2020
Single- and multiple-dose pharmacokinetics of dezocine in patients with acute or chronic pain. Journal of clinical pharmacology, , Volume: 35, Issue:4	1995
Pharmacokinetics of parenteral dezocine in rhesus monkeys and dogs. Drug metabolism and disposition: the biological fate of chemicals, , Volume: 10, Issue:4
Pharmacokinetics of dezocine, a new analgesic: effect of dose and route of administration. European journal of clinical pharmacology, , Volume: 30, Issue:1	1986
Dezocine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs, , Volume: 38, Issue:2	1989

Bioavailability (1)

Article	Year
Pharmacokinetics of dezocine, a new analgesic: effect of dose and route of administration. European journal of clinical pharmacology, , Volume: 30, Issue:1	1986

Dosage (12)

Article	Year
The analgesic effects of dezocine in rats with chronic constriction injuries. Experimental animals, , Nov-09, Volume: 72, Issue:4	2023
Effect of ketorolac tromethamine combined with dezocine prior administration on hemodynamics and postoperative analgesia in patients undergoing laparoscopic hernia repair. Medicine, , May-20, Volume: 101, Issue:20	2022
The effectiveness of esketamine and propofol versus dezocine and propofol sedation during gastroscopy: A randomized controlled study. Journal of clinical pharmacy and therapeutics, , Volume: 47, Issue:9	2022
Effect of dezocine combined with propofol on painless gastroscopy in patients with suspect gastric carcinoma. Journal of cancer research and therapeutics, , Volume: 12, Issue:Supplement	2016
[Application of dezoxine plus dexmedetomidine in strabismus surgery]. Zhonghua yi xue za zhi, , May-20, Volume: 94, Issue:19	2014
Sex-related differences in the antinociceptive effects of opioids: importance of rat genotype, nociceptive stimulus intensity, and efficacy at the mu opioid receptor. Psychopharmacology, , Volume: 150, Issue:4	2000
Use of analgesics during propofol sedation: a comparison of ketorolac, dezocine, and fentanyl. Journal of clinical anesthesia, , Volume: 7, Issue:6	1995
Preliminary clinical experience with dezocine, a new potent analgesic. Current medical research and opinion, , Volume: 6, Issue:7	1980
Anesthetic potency of dezocine and its interaction with morphine in rats. Anesthesia and analgesia, , Volume: 62, Issue:10	1983
Reassessment of verbal and visual analog ratings in analgesic studies. Clinical pharmacology and therapeutics, , Volume: 38, Issue:1	1985
Hemodynamic and respiratory effects of dezocine, ciramadol, and morphine. Clinical pharmacology and therapeutics, , Volume: 38, Issue:1	1985
Dezocine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs, , Volume: 38, Issue:2	1989

Interactions (12)

Article	Year
Effects of dexmedetomidine combined with dezocine on T lymphocytes, NK cells and cognitive function in elderly patients with gastrointestinal cancer after radical surgery. Cellular and molecular biology (Noisy-le-Grand, France), , Oct-31, Volume: 69, Issue:10	2023
[Application value and safety of prostate peripheral nerve block combined with dezocine in transrectal prostate biopsy]. Zhonghua nan ke xue = National journal of andrology, , Volume: 28, Issue:6	2022
Effects of dezocine combined with dexmedetomidine on adverse reactions and inflammatory factors in patients undergoing HIPEC after intestinal surgery and its protective effect on the heart in the perioperative period. European review for medical and pharmacological sciences, , Volume: 26, Issue:10	2022
Effect of ketorolac tromethamine combined with dezocine prior administration on hemodynamics and postoperative analgesia in patients undergoing laparoscopic hernia repair. Medicine, , May-20, Volume: 101, Issue:20	2022
Dexmedetomidine combined with sufentanil and dezocine-based patient-controlled intravenous analgesia increases female patients' global satisfaction degree after thoracoscopic surgery. Journal of cardiothoracic surgery, , Apr-21, Volume: 16, Issue:1	2021
Analgesic Effect of Dizocine Combined with Ropivacaine on Recurrent Neuropathic Pain in Peripheral Nerve Compression Rats. Pharmacology, , Volume: 105, Issue:9-10	2020
The application of dexmedetomidine combined with dezocine in thoracoscopic radical resection of lung cancer and its effect on awakening quality of patients. European review for medical and pharmacological sciences, , Volume: 23, Issue:17	2019
Effect of propofol combined with opioids on cough reflex suppression in gastroscopy: study protocol for a double-blind randomized controlled trial. BMJ open, , Sep-01, Volume: 7, Issue:9	2017
Effect of dezocine combined with propofol on painless gastroscopy in patients with suspect gastric carcinoma. Journal of cancer research and therapeutics, , Volume: 12, Issue:Supplement	2016
Clinical study of anesthetization by dezocine combined with propofol for indolent colonoscopy. World journal of gastroenterology, , Jun-28, Volume: 22, Issue:24	2016
[Application of patient-controlled intravenous analgesia of dezocine combined with sufentanil in burn patients after surgery]. Zhonghua shao shang za zhi = Zhonghua shaoshang zazhi = Chinese journal of burns, , Volume: 31, Issue:1	2015
Low Concentration of Dezocine in Combination With Morphine Enhance the Postoperative Analgesia for Thoracotomy. Journal of cardiothoracic and vascular anesthesia, , Volume: 29, Issue:4	2015