Compounds > levorphanol
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levorphanol

Description

Levorphanol: A narcotic analgesic that may be habit-forming. It is nearly as effective orally as by injection. [MeSH]

Levorphanol : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID5359272
CHEMBL ID592
SCHEMBL ID24335
CHEBI ID6444
MeSH IDM0012437

Synonyms (108)

Synonym
morphinan-3-ol, 17-methyl-
(-)-n-methylmorphinan-3-ol
17-methylmorphinan-3-ol
einecs 206-048-0
racemorphanum [inn-latin]
2h-10, 4a-iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, dl-
1,3,4,9,10,10a-hexahydro-11-methyl-2h-10,4a-iminoethanophenanthren-6-ol, l-
(+-)-17-methylmorphinan-3-ol
levorfanolo [dcit]
levorphan
ro 1-6794
morphinan-3-ol, 17-methyl-, (+-)-
dea no. 9733
aromarone
racemic dromoran
nu 2206
methorfinan [czech]
orphan
morphinan, 3-hydroxy-n-methyl-, (+-)-
(-)-3-hydroxy-n-methylmorphinan
morphinan, 3-hydroxy-n-methyl, (+)-
morphinan-3-ol, 17-methyl-, (-)-
methorphinan
levorfanol [inn-spanish]
antalgin
racemorphan [inn:ban]
2h-10,4a-(iminoethano)phenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, (+)-
levorphanolum [inn-latin]
racemorfano [inn-spanish]
dl-3-hydroxy-n-methylmorphinan
ro 1-5431
dea no. 9220
racemorphane [inn-french]
einecs 201-002-6
2h-10,4a-iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-
morphinan, 3-hydroxy-17-methyl-
levodroman
n-methyl-3-hydroxymorphinan
cetarin
2h-10,4a-iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, l-
hsdb 3349
(+-)-3-hydroxy-n-methylmorphinan
dromoran
77-07-6
C08014
levorphanol
DB00854
levorphanol (inn)
D08123
chembl592 ,
bdbm50017233
racemorphanum
297-90-5
(+-)-n-methylmorphinan-3-ol
methorfinan
racemorfano
unii-v7r79hn3xd
v7r79hn3xd ,
racemorphane
ids-nl-007
chebi:6444 ,
bdbm82427
levorphanol-tartarate
cas_5985-38-6
bdbm50369518
levorphanal
levorphanol dl-form
unii-27618j1n2x
levorphanolum
levorphanol [inn:ban]
levorfanol
levorfanolo
27618j1n2x ,
levorphanol [hsdb]
levorphanol [inn]
levorphanol [mi]
levorphanol [who-dd]
levorphanol [vandf]
racemorphan [inn]
levorphanol dl-form [mi]
(+/-)-n-methyl-3-hydroxymorphinan
ids-nr-003
(+/-)-n-methylmorphinan-3-ol
(+/-)-3-hydroxy-n-methylmorphinan
morphinan-3-ol, 17-methyl-, (+/-)-
nu-2206
(-) 3-hydroxy-n-methylmorphinan
gtpl7595
SCHEMBL24335
9.alpha.,13.alpha.,14.alpha.-morphinan-3-ol, 17-methyl-
17-methylmorphinan-3-ol, (+)- #
d-form of levorphanol
DTXSID3023213 ,
(1r,9r,10r)-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol
bdbm224028
l-morphan
Q2579108
DTXSID301016136
(1r,9r,10r)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
(4br,8ar,9r)-11-methyl-6,7,8,8a,9,10-hexahydro-5h-9,4b-(epiminoethano)phenanthren-3-ol
77-07-6 (free)
(1r,9r,10r)-17-methyl-17-azatetracyclo[7.5.3.0?,??.0?,?]heptadeca-2,4,6-trien-4-ol
dtxcid203213
leuodromoran
2h-10,4a-iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11- methyl-, l-
levorphanolum (inn-latin)
levorfanol (inn-spanish)
1,3,4,9,10,10a-hexahydro-11-methyl-2h-10,4a-iminoethanophenanthren-6- ol, l-

Drug Classes (1)

ClassDescription
morphinane alkaloidAn isoquinoline alkaloid based on a morphinan skeleton and its substituted derivatives.

Pathways (1)

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

PathwayProteinsCompounds
Levorphanol Action Pathway3111

Protein Targets (26)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Solute carrier family 22 member 1 Homo sapiens (human)IC508.0000AID1526751
Glutamate receptor ionotropic, NMDA 2DHomo sapiens (human)IC502.6000AID143909; AID143911
AcetylcholinesteraseElectrophorus electricus (electric eel)Ki25.0000AID514203
Sigma non-opioid intracellular receptor 1Mus musculus (house mouse)Ki0.0019AID204010
Glutamate receptor ionotropic, NMDA 3BHomo sapiens (human)IC502.6000AID143909; AID143911
Kappa-type opioid receptorMus musculus (house mouse)Ki0.0100AID148126
Mu-type opioid receptorHomo sapiens (human)IC500.0001AID150822
Mu-type opioid receptorHomo sapiens (human)Ki0.0002AID148328; AID151001; AID259394; AID290256; AID362196; AID670110
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC504.4500AID144475; AID144477
Delta-type opioid receptorHomo sapiens (human)IC500.0040AID148090; AID149186
Delta-type opioid receptorHomo sapiens (human)Ki0.0042AID147944; AID148369; AID149778; AID259395; AID290258; AID362197; AID670113
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)Ki5.0026AID147944; AID149121; AID514203
Kappa-type opioid receptorHomo sapiens (human)IC500.0040AID147865
Kappa-type opioid receptorHomo sapiens (human)Ki0.0023AID148149; AID149978; AID259396; AID290257; AID362198; AID670111
Mu-type opioid receptorMus musculus (house mouse)Ki0.0003AID149172
Mu-type opioid receptorCavia porcellus (domestic guinea pig)IC500.0006AID148996
Mu-type opioid receptorCavia porcellus (domestic guinea pig)Ki0.0002AID147903
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC504.4500AID144475; AID144477
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC504.4500AID144475; AID144477
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC504.4500AID144475; AID144477
Glutamate receptor ionotropic, NMDA 1Homo sapiens (human)IC502.6000AID143909; AID143911
Glutamate receptor ionotropic, NMDA 2AHomo sapiens (human)IC502.6000AID143909; AID143911
Glutamate receptor ionotropic, NMDA 2BHomo sapiens (human)IC502.6000AID143909; AID143911
Glutamate receptor ionotropic, NMDA 2CHomo sapiens (human)IC502.6000AID143909; AID143911
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC504.4500AID144475; AID144477
Glutamate receptor ionotropic, NMDA 3AHomo sapiens (human)IC502.6000AID143909; AID143911
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC504.4500AID144475; AID144477
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC504.4500AID144475; AID144477

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Mas-related G-protein coupled receptor member X2Homo sapiens (human)EC5017.5000AID1802708; AID1802709

Other Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Delta-type opioid receptorMus musculus (house mouse)Ke0.0006AID148951

Bioassays (109)

Assay IDTitleYearJournalArticle
AID1346364Human mu receptor (Opioid receptors)2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
ISSN: 0022-2623		The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
AID1346601Human GluN2C (Ionotropic glutamate receptors)2007The Journal of physiology, May-15, Volume: 581, Issue:Pt 1
ISSN: 0022-3751		Subunit-specific mechanisms and proton sensitivity of NMDA receptor channel block.
AID148036Binding affinity towards Opioid receptor mu 1 in guinea pig brain membranes using [3H]DAMGO as radioligand2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
ISSN: 0960-894X		Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan.
AID1145608Drug absorption in anesthetized rat colon at pH 6.81977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
ISSN: 0022-2623		Use of distribution coefficients in quantitative structure-activity relationships.
AID1526732Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.1 uM incubated for 2 mins by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
ISSN: 1520-4804		Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
ISSN: 1878-5832		DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID184526Effect was expressed as mortality after injection of kainic acid (10 mg/kg) and the drug at the dose of 40 mg/Kg after 48 hr2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
ISSN: 0960-894X		Anticonvulsant effects of new morphinan derivatives.
AID148951Inhibition of naloxone activity in mouse vas deferens assay for Opioid receptor delta 11982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
ISSN: 0022-2623		Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogues: effect of conformational constraints on opiate receptor selectivity.
AID362197Displacement of [3H]Naltindole from human delta opioid receptor expressed in CHO cell membrane2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
ISSN: 1464-3405		Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.
AID148126Binding affinity for mouse opioid receptor kappa1989Journal of medicinal chemistry, Sep, Volume: 32, Issue:9
ISSN: 0022-2623		Benzofuro[2,3-c]pyridin-6-ols: synthesis, affinity for opioid-receptor subtypes, and antinociceptive activity.
AID148149Inhibitory activity against Opioid receptor kappa 1 in chinese Hamster Ovary (CHO) cell membranes was determined using [3H]U-69593 radioligand2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
ISSN: 0022-2623		Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.
AID149867Inhibitory potency against Opioid receptor mu 1 in the guinea pig ileum assay1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
ISSN: 0022-2623		Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogues: effect of conformational constraints on opiate receptor selectivity.
AID149121Binding affinity against opioid receptor kappa 1 using [3H]-U-69,593 as radioligand in guinea pig brain membranes.2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
ISSN: 0022-2623		10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
AID1526751Inhibition of human OCT1 expressed in HEK293 cells assessed as reduction in ASP+ substrate uptake by microplate reader based analysis2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
ISSN: 1520-4804		Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID112925Analgesic activity in mice after subcutaneous administration in tail-flicking assay; 1.13-1.311985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
ISSN: 0022-2623		Acylmorphinans. A novel class of potent analgesic agents.
AID151914Binding constant for the antagonist state was measured for its ability to displace [3H]naloxone from opioid mu 1 receptor buffered homogenate of rat brain membranes1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
ISSN: 0022-2623		Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.
AID670115Selectivity index, ratio of inhibition of human delta opioid receptor to inhibition of human mu opioid receptor2012Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8
ISSN: 1520-4804		Synthesis, binding affinity, and functional in vitro activity of 3-benzylaminomorphinan and 3-benzylaminomorphine ligands at opioid receptors.
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
ISSN: 1878-5832		DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID112915Analgesic activity in mice after oral administration in writhing assay; 0.70-2.801985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
ISSN: 0022-2623		Acylmorphinans. A novel class of potent analgesic agents.
AID624620Specific activity of expressed human recombinant UGT2B7H2000Annual review of pharmacology and toxicology, , Volume: 40ISSN: 0362-1642Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID290260Selectivity for kappa opioid receptor over delta opioid receptor2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
ISSN: 0960-894X		High-affinity carbamate analogues of morphinan at opioid receptors.
AID624621Specific activity of expressed human recombinant UGT2B7Y2000Annual review of pharmacology and toxicology, , Volume: 40ISSN: 0362-1642Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1135662Displacement of [3H]naloxone from opioid receptor (unknown origin) in brain homogenate measured after four washes1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
ISSN: 0022-2623		6beta-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist actitivty.
AID149272Binding affinity towards Opioid receptor kappa 1 in guinea pig brain membranes using [3H]U-69593 as radioligand2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
ISSN: 0960-894X		Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan.
AID1123188Displacement of [3H]-naloxone from opioid receptor in rat brain homogenate at 1x10'-8 M preincubated for 5 mins followed by washout measured after 15 mins by liquid scintillation counting analysis relative to control1979Journal of medicinal chemistry, Feb, Volume: 22, Issue:2
ISSN: 0022-2623		Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties.
AID290259Selectivity for kappa opioid receptor over mu opioid receptor expressed in CHO cells2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
ISSN: 0960-894X		High-affinity carbamate analogues of morphinan at opioid receptors.
AID149778Binding affinity against opioid receptor delta 1 using [3H]naltrindole as radioligand in guinea pig brain membranes.2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
ISSN: 0022-2623		10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
AID170083The compound was examined for circling behavior (marginal activity) using automated videotracking system 30 min after intraperitoneal injection at the dose of 40 mg/Kg in 12 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
ISSN: 0960-894X		Anticonvulsant effects of new morphinan derivatives.
AID233831Selective inhibitory activity was determined against kappa & mu opioid receptor in chinese Hamster Ovary (CHO) cell membranes2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
ISSN: 0022-2623		Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.
AID149868Inhibitory potency against Opioid receptor mu 1 in mouse vas deferens assay1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
ISSN: 0022-2623		Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogues: effect of conformational constraints on opiate receptor selectivity.
AID143909Inhibition of [3H]1 binding to dextromethorpin binding site of guinea pig microsomal pellet P3 N-methyl-D-aspartate glutamate receptor1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID144472Binding affinity against glycine binding site associated with N-methyl-D-aspartate glutamate receptor from rat synaptic plasma membrane(SPM) determined using [3H]glycine as radioligand.;NA = No effect1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID362198Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cell membrane2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
ISSN: 1464-3405		Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.
AID229388Relative affinity for delta and kappa opioid receptors2004Journal of medicinal chemistry, Apr-08, Volume: 47, Issue:8
ISSN: 0022-2623		2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.
AID362201Selectivity ratio of Ki for human mu opioid receptor to Ki for human kappa opioid receptor2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
ISSN: 1464-3405		Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.
AID235164Selectivity ratio expressed as Ki of delta opioid receptor to that of mu opioid receptor.2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
ISSN: 0022-2623		10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
AID235163Selectivity ratio expressed as Ki of delta opioid receptor to that of kappa opioid receptor.2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
ISSN: 0022-2623		10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
AID128507Analgesic activity was determined by writhing test after subcutaneous administration in mice1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
ISSN: 0022-2623		Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol.
AID188507Anticonvulsant activity in rat supramaximal electroshock (MES) test expressed as % rats protected at a dose of 2.5-10 mg/kg.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID170082The compound was examined for circling behavior (marginal activity) using automated videotracking system 30 min after intraperitoneal injection at the dose of 20 mg/Kg in 12 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
ISSN: 0960-894X		Anticonvulsant effects of new morphinan derivatives.
AID362196Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cell membrane2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
ISSN: 1464-3405		Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.
AID670116Selectivity index, ratio of inhibition of human kappa opioid receptor to inhibition of human mu opioid receptor2012Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8
ISSN: 1520-4804		Synthesis, binding affinity, and functional in vitro activity of 3-benzylaminomorphinan and 3-benzylaminomorphine ligands at opioid receptors.
AID670113Displacement of [3H]-naltrindole from human delta opioid receptor expressed in CHO cells after 3 hrs by scintillation counting2012Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8
ISSN: 1520-4804		Synthesis, binding affinity, and functional in vitro activity of 3-benzylaminomorphinan and 3-benzylaminomorphine ligands at opioid receptors.
AID204010Binding affinity for mouse sigma opioid receptor1989Journal of medicinal chemistry, Sep, Volume: 32, Issue:9
ISSN: 0022-2623		Benzofuro[2,3-c]pyridin-6-ols: synthesis, affinity for opioid-receptor subtypes, and antinociceptive activity.
AID147865In vitro binding affinity against cloned human Opioid receptor kappa 1 expressed in HEK 293S cells2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
ISSN: 0022-2623		The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
AID259395Displacement of [3H]naltrindole from human delta opioid receptor expressed in CHO cells2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
ISSN: 0022-2623		Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.
AID148369Inhibitory activity against Opioid receptor delta 1 in chinese Hamster Ovary (CHO) cell membranes was determined using [3H]naltrindole radioligand2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
ISSN: 0022-2623		Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.
AID178286Anticonvulsant activity in rat supramaximal electroshock (MES) test within a dose range of 15-60 mg/kg administered subcutaneously1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID144477Binding affinity against PCP binding site associated with N-methyl-D-aspartate glutamate receptor from rat synaptic plasma membrane(SPM) determined using [3H]TCP as radioligand.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID112912Analgesic activity in mice after oral administration in tail-flicking assay; 7.22-10.251985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
ISSN: 0022-2623		Acylmorphinans. A novel class of potent analgesic agents.
AID362199Selectivity ratio of Ki for human kappa opioid receptor to Ki for human delta opioid receptor2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
ISSN: 1464-3405		Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.
AID290257Displacement of [3H]U-69593 from human kappa opioid receptors expressed in CHO cell membrane2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
ISSN: 0960-894X		High-affinity carbamate analogues of morphinan at opioid receptors.
AID1145609Octanol-aqueous phase partition coefficient, log P of the compound at pH 7.101977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
ISSN: 0022-2623		Use of distribution coefficients in quantitative structure-activity relationships.
AID112932Analgesic activity in mice after subcutaneous administration in writhing assay; 0.06-0.221985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
ISSN: 0022-2623		Acylmorphinans. A novel class of potent analgesic agents.
AID23717Partition coefficient (logP)1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
ISSN: 0022-2623		Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.
AID235330Selectivity ratio of kappa opioid receptor to that of mu opioid receptor in guinea pig brain membranes2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
ISSN: 0960-894X		Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan.
AID149978Inhibition of [3H]U-69593 binding to Opioid receptor kappa 1 of Chinese hamster ovary membrane2004Journal of medicinal chemistry, Apr-08, Volume: 47, Issue:8
ISSN: 0022-2623		2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.
AID150244Concentration required to inhibit [3H]naltrexone binding to Opioid receptors1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
ISSN: 0022-2623		Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol.
AID1123189Displacement of [3H]-naloxone from opioid receptor in rat brain homogenate at 1x10'-8 M preincubated for 5 mins measured after second washout by liquid scintillation counting analysis relative to control1979Journal of medicinal chemistry, Feb, Volume: 22, Issue:2
ISSN: 0022-2623		Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties.
AID147893Sensitivity to naloxone against Opioid receptor mu 1 in the guinea pig ileum assay1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
ISSN: 0022-2623		Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogues: effect of conformational constraints on opiate receptor selectivity.
AID151001Inhibitory activity against Opioid receptor mu 1 in chinese Hamster Ovary (CHO) cells membranes was determined using [3H]-DAMGO radioligand2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
ISSN: 0022-2623		Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.
AID290258Displacement of [3H]naltrindole from human delta opioid receptors expressed in CHO cell membrane2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
ISSN: 0960-894X		High-affinity carbamate analogues of morphinan at opioid receptors.
AID1526731Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.05 uM incubated for 2 mins by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
ISSN: 1520-4804		Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID1150953Displacement of [3H]etorphine from opioid receptor in guinea pig brain homogenate by scintillation counting analysis1976Journal of medicinal chemistry, Jun, Volume: 19, Issue:6
ISSN: 0022-2623		Stereospecific interaction of the quaternized opiate, N-methyllevorphanol, with opiate receptors.
AID205268Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
ISSN: 0022-2623		[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID128490Analgesic activity 30 min after subcutaneous administration in mouse by using PQW test; NT=Not tested1989Journal of medicinal chemistry, Sep, Volume: 32, Issue:9
ISSN: 0022-2623		Benzofuro[2,3-c]pyridin-6-ols: synthesis, affinity for opioid-receptor subtypes, and antinociceptive activity.
AID148996Inhibitory activity against opioid receptor mu of guinea pig brain using [3H]DAGO radioligand1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
ISSN: 0022-2623		Synthesis, opioid receptor binding profile, and antinociceptive activity of 1-azaspiro[4.5]decan-10-yl amides.
AID205267Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
ISSN: 0022-2623		[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID149186Inhibitory activity against opioid receptor delta of guinea pig was determined by using [3H]DADLE radioligand1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
ISSN: 0022-2623		Synthesis, opioid receptor binding profile, and antinociceptive activity of 1-azaspiro[4.5]decan-10-yl amides.
AID259394Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
ISSN: 0022-2623		Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.
AID144475Binding affinity against dextromethorpin binding site of N-methyl-D-aspartate glutamate receptor from rat brain using [3H]11992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID149904Binding affinity towards Opioid receptor delta 1 in guinea pig brain membranes using [3H]naltrindole as radioligand2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
ISSN: 0960-894X		Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan.
AID1145607Octanol-aqueous phase distribution coefficient, log D of the compound1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
ISSN: 0022-2623		Use of distribution coefficients in quantitative structure-activity relationships.
AID290256Displacement of [3H]DAMGO from human mu opioid receptors expressed in CHO cell membrane2007Bioorganic & medicinal chemistry letters, Mar-15, Volume: 17, Issue:6
ISSN: 0960-894X		High-affinity carbamate analogues of morphinan at opioid receptors.
AID196182The compound was tested for anticonvulsive activity expressed as seizure score after 4 hr of injection of kainic acid (10 mg/kg) and the drug at the dose of 40 mg/Kg in 15 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
ISSN: 0960-894X		Anticonvulsant effects of new morphinan derivatives.
AID150822In vitro binding affinity against cloned human Opioid receptor mu 1 expressed in HEK 293S cells2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
ISSN: 0022-2623		The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
AID196181The compound was tested for anticonvulsive activity expressed as seizure score after 4 hr of injection of kainic acid (10 mg/kg) and the drug at the dose of 20 mg/Kg in 15 rats2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
ISSN: 0960-894X		Anticonvulsant effects of new morphinan derivatives.
AID235329Selectivity ratio of kappa opioid receptor to that of delta opioid receptor in guinea pig brain membranes2001Bioorganic & medicinal chemistry letters, Oct-22, Volume: 11, Issue:20
ISSN: 0960-894X		Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan.
AID1123191Displacement of [3H]-naloxone from opioid receptor in rat brain homogenate at 1x10'-8 M preincubated for 5 mins measured after fourth washout by liquid scintillation counting analysis relative to control1979Journal of medicinal chemistry, Feb, Volume: 22, Issue:2
ISSN: 0022-2623		Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties.
AID1123190Displacement of [3H]-naloxone from opioid receptor in rat brain homogenate at 1x10'-8 M preincubated for 5 mins measured after third washout by liquid scintillation counting analysis relative to control1979Journal of medicinal chemistry, Feb, Volume: 22, Issue:2
ISSN: 0022-2623		Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties.
AID259398Selectivity for human kappa opioid receptor over delta opioid receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
ISSN: 0022-2623		Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.
AID14593350% Inhibition of stereospecific [3H]-naltrexone (10e-9 M) binding towards opiate receptor in rat brain homogenate1985Journal of medicinal chemistry, Sep, Volume: 28, Issue:9
ISSN: 0022-2623		Acylmorphinans. A novel class of potent analgesic agents.
AID184524Effect was expressed as mortality after injection of kainic acid (10 mg/kg) and the drug at the dose of 20 mg/Kg after 48 hr out of 19 animals2001Bioorganic & medicinal chemistry letters, Jul-09, Volume: 11, Issue:13
ISSN: 0960-894X		Anticonvulsant effects of new morphinan derivatives.
AID229399Relative affinity for mu and kappa opioid receptors2004Journal of medicinal chemistry, Apr-08, Volume: 47, Issue:8
ISSN: 0022-2623		2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.
AID178287Anticonvulsant activity in rat supramaximal electroshock (MES) test within a dose range of 15-60 mg/kg.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID149172Binding affinity for mouse opioid receptor mu1989Journal of medicinal chemistry, Sep, Volume: 32, Issue:9
ISSN: 0022-2623		Benzofuro[2,3-c]pyridin-6-ols: synthesis, affinity for opioid-receptor subtypes, and antinociceptive activity.
AID670111Displacement of [3H]-U69,593 from human kappa opioid receptor expressed in CHO cells after 60 mins by scintillation counting2012Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8
ISSN: 1520-4804		Synthesis, binding affinity, and functional in vitro activity of 3-benzylaminomorphinan and 3-benzylaminomorphine ligands at opioid receptors.
AID362200Selectivity ratio of Ki for human mu opioid receptor to Ki for human delta opioid receptor2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
ISSN: 1464-3405		Synthesis and pharmacological evaluation of hydrophobic esters and ethers of butorphanol at opioid receptors.
AID1135664Displacement of [3H]naloxone from opioid receptor (unknown origin) in brain homogenate at 1 uM to 10 nM1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
ISSN: 0022-2623		6beta-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist actitivty.
AID259397Selectivity for human kappa opioid receptor over mu opioid receptor2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
ISSN: 0022-2623		Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.
AID149216IC50 ratio measured as inhibitory potencies in mouse vas deferens and guinea pig ileum assays1982Journal of medicinal chemistry, Dec, Volume: 25, Issue:12
ISSN: 0022-2623		Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogues: effect of conformational constraints on opiate receptor selectivity.
AID148090In vitro binding affinity against cloned human Opioid receptor delta 1 expressed in HEK 293S cells2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
ISSN: 0022-2623		The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
AID1526733Substrate activity at human OCT1 expressed in HEK293 cells assessed as increase in compound uptake at 0.5 uM incubated for 2 mins by LC-MS/MS analysis relative to control empty vector transfected cells2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
ISSN: 1520-4804		Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID147944Inhibition of [3H]naltrindole binding to opioid receptor delta 1 of Chinese hamster ovary membrane2004Journal of medicinal chemistry, Apr-08, Volume: 47, Issue:8
ISSN: 0022-2623		2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.
AID148328Inhibition of [3H]-DAMGO binding to Opioid receptor mu 1 of Chinese hamster ovary membrane2004Journal of medicinal chemistry, Apr-08, Volume: 47, Issue:8
ISSN: 0022-2623		2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.
AID514203Inhibition of electric eel AChE by Ellman's method2010Bioorganic & medicinal chemistry, Jul-15, Volume: 18, Issue:14
ISSN: 1464-3391		Morphinans and isoquinolines: acetylcholinesterase inhibition, pharmacophore modeling, and interaction with opioid receptors.
AID151584Binding constant for the agonist state was measured for its ability to displace [3H]naloxone from opioid mu 1 receptor buffered homogenate of rat brain membranes1988Journal of medicinal chemistry, Mar, Volume: 31, Issue:3
ISSN: 0022-2623		Structure-activity relationships for drugs binding to the agonist and antagonist states of the primary morphine receptor.
AID147903Binding affinity against opioid receptor mu 1 using [3H]DAMGO as radioligand in guinea pig brain membranes.2004Journal of medicinal chemistry, Jan-01, Volume: 47, Issue:1
ISSN: 0022-2623		10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
AID233830Selective inhibitory activity was determined against kappa & delta opioid receptor in chinese Hamster Ovary (CHO) cell membranes2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
ISSN: 0022-2623		Design and synthesis of novel dimeric morphinan ligands for kappa and micro opioid receptors.
AID128505Analgesic activity was determined by tail flick assay after subcutaneous administration in mice1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
ISSN: 0022-2623		Synthesis and pharmacology of metabolically stable tert-butyl ethers of morphine and levorphanol.
AID670110Displacement of [3H]-DAMGO from human mu opioid receptor expressed in CHO cells after 60 mins by scintillation counting2012Journal of medicinal chemistry, Apr-26, Volume: 55, Issue:8
ISSN: 1520-4804		Synthesis, binding affinity, and functional in vitro activity of 3-benzylaminomorphinan and 3-benzylaminomorphine ligands at opioid receptors.
AID1526752Passive membrane permeability by LC-MS/MS analysis based PAMPA2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
ISSN: 1520-4804		Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.
AID143911Binding affinity against dextromethorpin binding site associated with N-methyl-D-aspartate glutamate receptor from guinea pig mitochondriall pellet P2 determined using [3H]1 as radioligand.1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
ISSN: 0022-2623		Synthesis and evaluation of 3-substituted 17-methylmorphinan analogs as potential anticonvulsant agents.
AID259396Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cells2006Journal of medicinal chemistry, Jan-12, Volume: 49, Issue:1
ISSN: 0022-2623		Synthesis and preliminary in vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at mu, delta, and kappa opioid receptors.
AID151006Selectivity of mu IC50 to that of delta IC50 was calculated2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
ISSN: 0022-2623		The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
AID624616Specific activity of expressed human recombinant UGT2B152000Annual review of pharmacology and toxicology, , Volume: 40ISSN: 0362-1642Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID1145611Dissociation constant, pKa of the compound by titrimetric analysis1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
ISSN: 0022-2623		Use of distribution coefficients in quantitative structure-activity relationships.
AID1802708Intracellular Calcium Mobilization Assay from Article 10.1038/nchembio.2334: \\In silico design of novel probes for the atypical opioid receptor MRGPRX2.\\2017Nature chemical biology, 05, Volume: 13, Issue:5
ISSN: 1552-4469		In silico design of novel probes for the atypical opioid receptor MRGPRX2.
AID1802709PRESTO-Tango Assay from Article 10.1038/nchembio.2334: \\In silico design of novel probes for the atypical opioid receptor MRGPRX2.\\2017Nature chemical biology, 05, Volume: 13, Issue:5
ISSN: 1552-4469		In silico design of novel probes for the atypical opioid receptor MRGPRX2.

Research

Studies (617)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990498 (80.71)18.7374
1990's62 (10.05)18.2507
2000's37 (6.00)29.6817
2010's14 (2.27)24.3611
2020's6 (0.97)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials26 (4.10%)5.53%
Reviews20 (3.15%)6.00%
Case Studies12 (1.89%)4.05%
Observational0 (0.00%)0.25%
Other576 (90.85%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
racemethorphan
0
aromatic ether;
morphinane alkaloid;
morphinane-like compound;
organic heterotetracyclic compound		00low000000
LSM-1535
0
morphinane alkaloid00low000000
pseudomorphine
0
morphinane alkaloid00low000000
diprenorphine
6
morphinane alkaloid1981200731.7low032100
buprenorphine
10
morphinane alkaloiddelta-opioid receptor antagonist;
kappa-opioid receptor antagonist;
mu-opioid receptor agonist;
opioid analgesic		1988202122.2low015211
etorphine
0
alcohol;
morphinane alkaloid		opioid analgesic;
opioid receptor agonist;
sedative		00low000000
dimemorfan
0
morphinane alkaloid00low000000
codeine
48
morphinane alkaloid;
organic heteropentacyclic compound		antitussive;
drug allergen;
environmental contaminant;
opioid analgesic;
opioid receptor agonist;
prodrug;
xenobiotic		1962200047.4low5453000
dihydrocodeine
0
morphinane alkaloid00low000000
hydromorphone
22
morphinane alkaloid;
organic heteropentacyclic compound		mu-opioid receptor agonist;
opioid analgesic		1963202247.9low1200101
nalmefene
0
morphinane alkaloid00low000000
nalorphine
38
morphinane alkaloid1955198653.7low1380000
naloxone
135
morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist		1972200744.0low012110400
oxymorphone
7
morphinane alkaloid1969198648.1low070000
morphine
214
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		1955202345.5low418420802
beta-funaltrexamine
0
morphinane alkaloid00low000000
pholcodine
0
morphinane alkaloid;
organic heteropentacyclic compound		antitussive;
drug allergen;
mu-opioid receptor agonist;
opioid analgesic		00low000000
thebaine
3
morphinane alkaloid;
organic heteropentacyclic compound		1968197154.7low030000
ethylmorphine
0
morphinane alkaloid00low000000
metopon
0
morphinane alkaloid00low000000
levallorphan
37
morphinane alkaloid1954201053.9low0351100
dihydromorphine
4
morphinane alkaloid1981198938.2low040000
morphine-6-glucuronide
0
morphinane alkaloid00low000000
dextrorphan
129
morphinane alkaloid1953202440.1high211112312
butorphanol
4
morphinane alkaloidantitussive;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic		1984200527.0low012100
desomorphine
0
morphinane alkaloid00low000000
nicomorphine
0
morphinane alkaloid00low000000
salutaridine
0
morphinane alkaloidanti-HBV agent;
metabolite		00low000000
sinomenine
0
morphinane alkaloid00low000000
morphinone
0
morphinane alkaloid00low000000
oripavine
0
ether;
morphinane alkaloid;
organic heteropentacyclic compound;
organic hydroxy compound;
tertiary amino compound		bacterial xenobiotic metabolite;
opioid analgesic		00low000000
heroin
18
morphinane alkaloidmu-opioid receptor agonist;
opioid analgesic;
prodrug		1966198849.4low0180000
neopine
0
morphinane alkaloid;
organic heteropentacyclic compound		00low000000
6-o-monoacetylmorphine
0
morphinane alkaloid00low000000
normorphine
0
morphinane alkaloid00low000000
morphine-3-glucuronide
0
morphinane alkaloid00low000000
naltrindole benzofuran
0
morphinane alkaloid00low000000
codeine-6-glucuronide
0
morphinane alkaloid00low000000
morphinans
80
isoquinoline alkaloid fundamental parent;
morphinane alkaloid		1959199245.5low2764000
norcodeine
0
morphinane alkaloid00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
4-hydroxybenzoic acid
1
monohydroxybenzoic acidalgal metabolite;
plant metabolite		2000200024.0low001000
quinacrine
1
acridines;
aromatic ether;
organochlorine compound;
tertiary amino compound		antimalarial;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor		1985198539.0low010000
benzoic acid
2
benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite		1977200035.5low011000
benzyl alcohol
1
benzyl alcoholsantioxidant;
fragrance;
metabolite;
solvent		2000200024.0low001000
betaine
1
amino-acid betaine;
glycine derivative		fundamental metabolite201620168.0low000010
butyric acid
1
fatty acid 4:0;
straight-chain saturated fatty acid		human urinary metabolite;
Mycoplasma genitalium metabolite		2000200024.0low001000
salicylic acid
2
monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite		1977200035.5low011000
gallic acid
1
trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite		2000200024.0low001000
octanoic acid
1
medium-chain fatty acid;
straight-chain saturated fatty acid		antibacterial agent;
Escherichia coli metabolite;
human metabolite		2000200024.0low001000
4-aminophenol
1
aminophenolallergen;
metabolite		2000200024.0low001000
bupropion
1
aromatic ketone;
monochlorobenzenes;
secondary amino compound		antidepressant;
environmental contaminant;
xenobiotic		201620168.0low000010
3-chlorobenzoic acid
1
monochlorobenzoic aciddrug metabolite1977197747.0low010000
aminocaproic acid
1
amino acid zwitterion;
epsilon-amino acid;
omega-amino fatty acid		antifibrinolytic drug;
hematologic agent;
metabolite		201620168.0low000010
glycine
1
alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical		1992199232.0low001000
hydroquinone
1
benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent		2000200024.0low001000
methanol
1
alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite		2000200024.0low001000
acetanilide
1
acetamides;
anilide		analgesic1977197747.0low010000
niacin
1
pyridine alkaloid;
pyridinemonocarboxylic acid;
vitamin B3		antidote;
antilipemic drug;
EC 3.5.1.19 (nicotinamidase) inhibitor;
Escherichia coli metabolite;
human urinary metabolite;
metabolite;
mouse metabolite;
plant metabolite;
vasodilator agent		201620168.0low000010
n,n-dimethylaniline
1
dimethylaniline;
tertiary amine		2000200024.0low001000
4-nitrophenol
2
4-nitrophenolshuman xenobiotic metabolite;
mouse metabolite		1977200035.5low011000
phenol
2
phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite		1977200035.5low011000
pyrazinamide
1
monocarboxylic acid amide;
N-acylammonia;
pyrazines		antitubercular agent;
prodrug		201620168.0low000010
pyridoxine
1
hydroxymethylpyridine;
methylpyridines;
monohydroxypyridine;
vitamin B6		cofactor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		201620168.0low000010
pyrogallol
1
benzenetriol;
phenolic donor		plant metabolite2000200024.0low001000
thiamine
1
primary alcohol;
vitamin B1		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		201620168.0low000010
tryptophan
1
alpha-amino acid;
amino acid zwitterion;
aminoalkylindole;
aromatic amino acid;
polar amino acid		Daphnia magna metabolite2000200024.0medium001000
vanillin
1
benzaldehydes;
monomethoxybenzene;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
flavouring agent;
plant metabolite		2000200024.0low001000
catechin
1
hydroxyflavan2000200024.0low001000
gallopamil
1
benzenes;
organic amino compound		1985198539.0low010000
sk&f 10047
1
1988198836.0medium010000
menthol
1
p-menthane monoterpenoid;
secondary alcohol		volatile oil component2000200024.0low001000
beta-resorcylic acid
1
1977197747.0low010000
2-aminofluorene
1
2000200024.0low001000
3-methoxymorphinan
1
2001200123.0low000100
4-aminopyridine
1
aminopyridine;
aromatic amine		avicide;
orphan drug;
potassium channel blocker		1985198539.0low010000
homovanillic acid
1
guaiacols;
monocarboxylic acid		human metabolite;
mouse metabolite		2000200024.0low001000
phenytoin
2
imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent		1985201623.5low010010
6-hydroxymelatonin
1
acetamides;
tryptamines		metabolite;
mouse metabolite		2000200024.0low001000
8-(4-sulfophenyl)theophylline
1
1985198539.0low010000
8-phenyltheophylline
1
1985198539.0low010000
oxyquinoline
1
monohydroxyquinolineantibacterial agent;
antifungal agrochemical;
antiseptic drug;
iron chelator		2000200024.0low001000
acebutolol
1
aromatic amide;
ethanolamines;
ether;
monocarboxylic acid amide;
propanolamine;
secondary amino compound		anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
sympathomimetic agent		201620168.0low000010
acetaminophen
2
acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic		2000201616.0low001010
acetazolamide
1
monocarboxylic acid amide;
sulfonamide;
thiadiazoles		anticonvulsant;
diuretic;
EC 4.2.1.1 (carbonic anhydrase) inhibitor		201620168.0low000010
acetohydroxamic acid
1
acetohydroxamic acids;
carbohydroximic acid		algal metabolite;
EC 3.5.1.5 (urease) inhibitor		201620168.0low000010
alaproclate
1
alpha-amino acid ester201620168.0low000010
albendazole
1
aryl sulfide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		anthelminthic drug;
microtubule-destabilising agent;
tubulin modulator		201620168.0low000010
albuterol
1
phenols;
phenylethanolamines;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
environmental contaminant;
xenobiotic		201620168.0low000010
alendronate
1
1,1-bis(phosphonic acid);
primary amino compound		bone density conservation agent;
EC 2.5.1.1 (dimethylallyltranstransferase) inhibitor		201620168.0low000010
alfuzosin
1
monocarboxylic acid amide;
quinazolines;
tetrahydrofuranol		alpha-adrenergic antagonist;
antihypertensive agent;
antineoplastic agent		201620168.0low000010
alosetron
1
imidazoles;
pyridoindole		antiemetic;
gastrointestinal drug;
serotonergic antagonist		201620168.0low000010
alprazolam
1
organochlorine compound;
triazolobenzodiazepine		anticonvulsant;
anxiolytic drug;
GABA agonist;
muscle relaxant;
sedative;
xenobiotic		201620168.0low000010
altretamine
1
triamino-1,3,5-triazine201620168.0low000010
amantadine
2
adamantanes;
primary aliphatic amine		analgesic;
antiparkinson drug;
antiviral drug;
dopaminergic agent;
NMDA receptor antagonist;
non-narcotic analgesic		2007201612.5low000110
ambenonium
1
quaternary ammonium ionEC 3.1.1.8 (cholinesterase) inhibitor201620168.0medium000010
diatrizoic acid
1
acetamides;
benzoic acids;
organoiodine compound		environmental contaminant;
radioopaque medium;
xenobiotic		201620168.0low000010
amifostine anhydrous
1
diamine;
organic thiophosphate		antioxidant;
prodrug;
radiation protective agent		201620168.0low000010
p-aminohippuric acid
1
N-acylglycineDaphnia magna metabolite201620168.0low000010
theophylline
3
dimethylxanthineadenosine 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		1977201631.3low020010
amiodarone
1
1-benzofurans;
aromatic ketone;
organoiodine compound;
tertiary amino compound		cardiovascular drug201620168.0low000010
amitriptyline
3
carbotricyclic compound;
tertiary amine		adrenergic uptake inhibitor;
antidepressant;
environmental contaminant;
tropomyosin-related kinase B receptor agonist;
xenobiotic		1985201623.7low011010
amlodipine
1
dihydropyridine;
ethyl ester;
methyl ester;
monochlorobenzenes;
primary amino compound		antihypertensive agent;
calcium channel blocker;
vasodilator agent		201620168.0low000010
amoxapine
1
dibenzooxazepineadrenergic uptake inhibitor;
antidepressant;
dopaminergic antagonist;
geroprotector;
serotonin uptake inhibitor		201620168.0low000010
anastrozole
1
nitrile;
triazoles		antineoplastic agent;
EC 1.14.14.14 (aromatase) inhibitor		201620168.0low000010
anisindione
1
aromatic ketone;
beta-diketone		anticoagulant;
vitamin K antagonist		1985198539.0low010000
antipyrine
1
pyrazoloneantipyretic;
cyclooxygenase 3 inhibitor;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic		1977197747.0low010000
aspirin
2
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		2000201616.0low001010
atenolol
1
ethanolamines;
monocarboxylic acid amide;
propanolamine		anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
environmental contaminant;
sympatholytic agent;
xenobiotic		201620168.0low000010
azathioprine
1
aryl sulfide;
C-nitro compound;
imidazoles;
thiopurine		antimetabolite;
antineoplastic agent;
carcinogenic agent;
DNA synthesis inhibitor;
hepatotoxic agent;
immunosuppressive agent;
prodrug		201620168.0low000010
baclofen
2
amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid;
monochlorobenzenes;
primary amino compound		central nervous system depressant;
GABA agonist;
muscle relaxant		1985201623.5low010010
bendazac
1
indazoles;
monocarboxylic acid		non-steroidal anti-inflammatory drug;
radical scavenger		201620168.0low000010
bendroflumethiazide
1
benzothiadiazine;
sulfonamide		antihypertensive agent;
diuretic		201620168.0low000010
benzbromarone
1
1-benzofurans;
aromatic ketone		uricosuric drug201620168.0low000010
benzocaine
1
benzoate ester;
substituted aniline		allergen;
antipruritic drug;
sensitiser;
topical anaesthetic		1985198539.0low010000
bepridil
1
pyrrolidines;
tertiary amine		anti-arrhythmia drug;
antihypertensive agent;
calcium channel blocker;
vasodilator agent		1985198539.0low010000
beta-naphthoflavone
1
extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist2000200024.0low001000
betaxolol
1
propanolamineantihypertensive agent;
beta-adrenergic antagonist;
sympatholytic agent		201620168.0low000010
bethanechol
1
carbamate ester;
quaternary ammonium ion		muscarinic agonist201620168.0low000010
bicalutamide
1
(trifluoromethyl)benzenes;
monocarboxylic acid amide;
monofluorobenzenes;
nitrile;
sulfone;
tertiary alcohol		201620168.0low000010
biperiden
2
piperidines;
tertiary alcohol;
tertiary amino compound		antidote to sarin poisoning;
antidyskinesia agent;
antiparkinson drug;
muscarinic antagonist;
parasympatholytic		1985201623.5low010010
bisacodyl
1
diarylmethane201620168.0low000010
bisoprolol
1
secondary alcohol;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
sympatholytic agent		201620168.0low000010
bumetanide
2
amino acid;
benzoic acids;
sulfonamide		diuretic;
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor		2000201616.0low001010
bupivacaine
1
aromatic amide;
piperidinecarboxamide;
tertiary amino compound		1985198539.0low010000
buspirone
2
azaspiro compound;
N-alkylpiperazine;
N-arylpiperazine;
organic heteropolycyclic compound;
piperidones;
pyrimidines		anxiolytic drug;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
sedative;
serotonergic agonist		1985201623.5low010010
busulfan
1
methanesulfonate esteralkylating agent;
antineoplastic agent;
carcinogenic agent;
insect sterilant;
teratogenic agent		201620168.0low000010
secbutabarbital
1
barbiturates201620168.0low000010
butacaine
1
benzoate ester1985198539.0low010000
butamben
1
amino acid ester;
benzoate ester;
primary amino compound;
substituted aniline		local anaesthetic1985198539.0low010000
caffeine
2
purine alkaloid;
trimethylxanthine		adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic		1985201623.5low010010
verapamil
2
aromatic ether;
nitrile;
polyether;
tertiary amino compound		1985201623.5low010010
candesartan
1
benzimidazolecarboxylic acid;
biphenylyltetrazole		angiotensin receptor antagonist;
antihypertensive agent;
environmental contaminant;
xenobiotic		201620168.0low000010
carbamazepine
3
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		1985201623.7low011010
carbinoxamine
1
monochlorobenzenes;
pyridines;
tertiary amino compound		anti-allergic agent;
antiparkinson drug;
H1-receptor antagonist;
muscarinic antagonist		201620168.0low000010
carisoprodol
1
carbamate estermuscle relaxant201620168.0low000010
carvedilol
1
carbazoles;
secondary alcohol;
secondary amino compound		alpha-adrenergic antagonist;
antihypertensive agent;
beta-adrenergic antagonist;
cardiovascular drug;
vasodilator agent		201620168.0low000010
celecoxib
1
organofluorine compound;
pyrazoles;
sulfonamide;
toluenes		cyclooxygenase 2 inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
cetirizine
1
ether;
monocarboxylic acid;
monochlorobenzenes;
piperazines		anti-allergic agent;
environmental contaminant;
H1-receptor antagonist;
xenobiotic		201620168.0low000010
chlorambucil
2
aromatic amine;
monocarboxylic acid;
nitrogen mustard;
organochlorine compound;
tertiary amino compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent		1979201626.5low010010
chlorcyclizine
1
diarylmethane201620168.0low000010
chlordiazepoxide
2
benzodiazepine1985201623.5low010010
chlormezanone
1
1,3-thiazine;
lactam;
monochlorobenzenes;
sulfone		antipsychotic agent;
anxiolytic drug;
muscle relaxant		201620168.0low000010
chloroquine
1
aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug		201620168.0low000010
chlorothiazide
1
benzothiadiazineantihypertensive agent;
diuretic		201620168.0low000010
chlorpheniramine
3
monochlorobenzenes;
pyridines;
tertiary amino compound		anti-allergic agent;
antidepressant;
antipruritic drug;
H1-receptor antagonist;
histamine antagonist;
serotonin uptake inhibitor		1985201623.7low011010
chlorpromazine
4
organochlorine compound;
phenothiazines;
tertiary amine		anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug		1985201625.8low012010
chlorpropamide
1
monochlorobenzenes;
N-sulfonylurea		hypoglycemic agent;
insulin secretagogue		201620168.0low000010
chlorthalidone
1
isoindoles;
monochlorobenzenes;
sulfonamide		201620168.0low000010
chlorzoxazone
1
1,3-benzoxazoles;
heteroaryl hydroxy compound;
organochlorine compound		muscle relaxant;
sedative		201620168.0low000010
cilostazol
1
lactam;
tetrazoles		anticoagulant;
bronchodilator agent;
EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor;
fibrin modulating drug;
neuroprotective agent;
platelet aggregation inhibitor;
vasodilator agent		201620168.0low000010
cimetidine
2
aliphatic sulfide;
guanidines;
imidazoles;
nitrile		adjuvant;
analgesic;
anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor		1985201623.5low010010
ciprofibrate
1
cyclopropanes;
monocarboxylic acid;
organochlorine compound		antilipemic drug2000200024.0low001000
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		201620168.0low000010
citalopram
1
2-benzofurans;
cyclic ether;
nitrile;
organofluorine compound;
tertiary amino compound		201620168.0low000010
clofibrate
2
aromatic ether;
ethyl ester;
monochlorobenzenes		anticholesteremic drug;
antilipemic drug;
geroprotector;
PPARalpha agonist		2000201616.0low001010
clofibric acid
1
aromatic ether;
monocarboxylic acid;
monochlorobenzenes		anticholesteremic drug;
antilipemic drug;
antineoplastic agent;
herbicide;
marine xenobiotic metabolite;
PPARalpha agonist		2000200024.0low001000
clomiphene
1
tertiary amineestrogen antagonist;
estrogen receptor modulator		201620168.0low000010
clomipramine
2
dibenzoazepineanticoronaviral agent;
antidepressant;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
serotonergic antagonist;
serotonergic drug;
serotonin uptake inhibitor		1985201623.5low010010
clonazepam
1
1,4-benzodiazepinone;
monochlorobenzenes		anticonvulsant;
anxiolytic drug;
GABA modulator		201620168.0low000010
clonidine
1
clonidine;
imidazoline		201620168.0low000010
4-chloro-N-(2,6-dimethyl-1-piperidinyl)-3-sulfamoylbenzamide
1
sulfonamide2000200024.0low001000
chlorazepate
1
1,4-benzodiazepinoneanticonvulsant;
anxiolytic drug;
GABA modulator;
prodrug		201620168.0medium000010
clotrimazole
1
conazole antifungal drug;
imidazole antifungal drug;
imidazoles;
monochlorobenzenes		antiinfective agent;
environmental contaminant;
xenobiotic		201620168.0low000010
4-cresol
1
cresolEscherichia coli metabolite;
human metabolite;
uremic toxin		2000200024.0low001000
cyclobenzaprine
1
carbotricyclic compoundantidepressant;
muscle relaxant;
tranquilizing drug		201620168.0low000010
cyclofenil
1
organic molecular entity201620168.0low000010
cyproheptadine
3
piperidines;
tertiary amine		anti-allergic agent;
antipruritic drug;
gastrointestinal drug;
H1-receptor antagonist;
serotonergic antagonist		1985201623.7low011010
danthron
1
dihydroxyanthraquinoneapoptosis inducer;
plant metabolite		2000200024.0low001000
dapsone
2
substituted aniline;
sulfone		anti-inflammatory drug;
antiinfective agent;
antimalarial;
leprostatic drug		2000201616.0low001010
decanoic acid
1
medium-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
anti-inflammatory agent;
antibacterial agent;
human metabolite;
plant metabolite;
volatile oil component		2000200024.0low001000
deferoxamine
1
acyclic desferrioxaminebacterial metabolite;
ferroptosis inhibitor;
iron chelator;
siderophore		201620168.0low000010
desipramine
3
dibenzoazepine;
secondary amino compound		adrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
cholinergic antagonist;
drug allergen;
EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
serotonin uptake inhibitor		1985201623.7low011010
amphetamine
1
primary amine201620168.0low000010
racemethorphan
3
aromatic ether;
morphinane alkaloid;
morphinane-like compound;
organic heterotetracyclic compound		1982200132.3medium011100
diazepam
2
1,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic		1985201623.5low010010
diazoxide
2
benzothiadiazine;
organochlorine compound;
sulfone		antihypertensive agent;
beta-adrenergic agonist;
bronchodilator agent;
cardiotonic drug;
diuretic;
K-ATP channel agonist;
sodium channel blocker;
sympathomimetic agent;
vasodilator agent		1985201623.5low010010
dibucaine
1
aromatic ether;
monocarboxylic acid amide;
tertiary amino compound		topical anaesthetic1985198539.0low010000
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		201620168.0low000010
dichlorphenamide
1
dichlorobenzene;
sulfonamide		antiglaucoma drug;
EC 4.2.1.1 (carbonic anhydrase) inhibitor;
ophthalmology drug		201620168.0low000010
dicyclomine
2
carboxylic ester;
tertiary amine		antispasmodic drug;
muscarinic antagonist;
parasympatholytic		1985201623.5low010010
pentetic acid
1
pentacarboxylic acidcopper chelator201620168.0low000010
diphenidol
1
benzenes;
piperidines;
tertiary alcohol		antiemetic1985198539.0low010000
diflunisal
2
monohydroxybenzoic acid;
organofluorine compound		non-narcotic analgesic;
non-steroidal anti-inflammatory drug		2000201616.0low001010
dilazep
1
benzoate ester;
diazepane;
diester;
methoxybenzenes		cardioprotective agent;
platelet aggregation inhibitor;
vasodilator agent		1985198539.0low010000
dimercaprol
1
dithiol;
primary alcohol		chelator201620168.0low000010
diphenhydramine
3
ether;
tertiary amino compound		anti-allergic agent;
antidyskinesia agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
antitussive;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
oneirogen;
sedative		1985201623.7low011010
dipyridamole
2
piperidines;
pyrimidopyrimidine;
tertiary amino compound;
tetrol		adenosine phosphodiesterase inhibitor;
EC 3.5.4.4 (adenosine deaminase) inhibitor;
platelet aggregation inhibitor;
vasodilator agent		1985201623.5low010010
disopyramide
1
monocarboxylic acid amide;
pyridines;
tertiary amino compound		anti-arrhythmia drug201620168.0low000010
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		201620168.0low000010
valproic acid
2
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		2000201616.0low001010
donepezil
1
aromatic ether;
indanones;
piperidines;
racemate		EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nootropic agent		201620168.0low000010
doxapram
1
morpholines;
pyrrolidin-2-ones		central nervous system stimulant201620168.0low000010
doxazosin
1
aromatic amine;
benzodioxine;
monocarboxylic acid amide;
N-acylpiperazine;
N-arylpiperazine;
quinazolines		alpha-adrenergic antagonist;
antihyperplasia drug;
antihypertensive agent;
antineoplastic agent;
vasodilator agent		201620168.0low000010
doxepin
3
dibenzooxepine;
tertiary amino compound		antidepressant1985201623.7low011010
doxylamine
2
pyridines;
tertiary amine		anti-allergic agent;
antiemetic;
antitussive;
cholinergic antagonist;
H1-receptor antagonist;
histamine antagonist;
sedative		2000201616.0low001010
droperidol
2
aromatic ketone;
benzimidazoles;
organofluorine compound		anaesthesia adjuvant;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic		1985201623.5low010010
dyphylline
1
oxopurine;
propane-1,2-diols		bronchodilator agent;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
muscle relaxant;
vasodilator agent		201620168.0low000010
edrophonium
1
phenols;
quaternary ammonium ion		antidote;
diagnostic agent;
EC 3.1.1.8 (cholinesterase) inhibitor		201620168.0low000010
emodin
1
trihydroxyanthraquinoneantineoplastic agent;
laxative;
plant metabolite;
tyrosine kinase inhibitor		2000200024.0low001000
estazolam
1
triazoles;
triazolobenzodiazepine		anticonvulsant;
anxiolytic drug;
GABA modulator		201620168.0low000010
etazolate
1
ethyl ester;
hydrazone;
pyrazolopyridine		alpha-secretase activator;
antidepressant;
antipsychotic agent;
anxiolytic drug;
GABA agent;
neuroprotective agent;
phosphodiesterase IV inhibitor		1985198539.0low010000
ethacrynic acid
2
aromatic ether;
aromatic ketone;
dichlorobenzene;
monocarboxylic acid		EC 2.5.1.18 (glutathione transferase) inhibitor;
ion transport inhibitor;
loop diuretic		2000201616.0low001010
ethosuximide
1
dicarboximide;
pyrrolidinone		anticonvulsant;
geroprotector;
T-type calcium channel blocker		201620168.0low000010
ethotoin
1
imidazolidine-2,4-dioneanticonvulsant201620168.0low000010
etidronate
1
1,1-bis(phosphonic acid)antineoplastic agent;
bone density conservation agent;
chelator		201620168.0low000010
etodolac
1
monocarboxylic acid;
organic heterotricyclic compound		antipyretic;
cyclooxygenase 2 inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
brl 42810
1
2-aminopurines;
acetate ester		antiviral drug;
prodrug		201620168.0low000010
felbamate
1
carbamate esteranticonvulsant;
neuroprotective agent		201620168.0low000010
felodipine
2
dichlorobenzene;
dihydropyridine;
ethyl ester;
methyl ester		anti-arrhythmia drug;
antihypertensive agent;
calcium channel blocker;
vasodilator agent		1985201623.5low010010
fenofibrate
1
aromatic ether;
chlorobenzophenone;
isopropyl ester;
monochlorobenzenes		antilipemic drug;
environmental contaminant;
geroprotector;
xenobiotic		201620168.0low000010
fenoldopam
1
benzazepinealpha-adrenergic agonist;
antihypertensive agent;
dopamine agonist;
dopaminergic antagonist;
vasodilator agent		201620168.0low000010
fenoprofen
2
monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		2000201616.0low001010
berotek
2
resorcinols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
sympathomimetic agent;
tocolytic agent		2000201914.5low001010
fentanyl
1
anilide;
monocarboxylic acid amide;
piperidines		adjuvant;
anaesthesia adjuvant;
anaesthetic;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic		201920195.0low000010
fexofenadine
1
piperidines;
tertiary amine		anti-allergic agent;
H1-receptor antagonist		201620168.0low000010
fipexide
1
benzodioxoles201620168.0low000010
flavoxate
1
carboxylic ester;
flavones;
piperidines;
tertiary amino compound		antispasmodic drug;
muscarinic antagonist;
parasympatholytic		201620168.0low000010
flecainide
1
aromatic ether;
monocarboxylic acid amide;
organofluorine compound;
piperidines		anti-arrhythmia drug201620168.0low000010
fluconazole
1
conazole antifungal drug;
difluorobenzene;
tertiary alcohol;
triazole antifungal drug		environmental contaminant;
P450 inhibitor;
xenobiotic		201620168.0low000010
flucytosine
1
aminopyrimidine;
nucleoside analogue;
organofluorine compound;
pyrimidine antifungal drug;
pyrimidone		prodrug201620168.0low000010
flufenamic acid
1
aromatic amino acid;
organofluorine compound		antipyretic;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		1985198539.0low010000
fluphenazine
3
N-alkylpiperazine;
organofluorine compound;
phenothiazines		anticoronaviral agent;
dopaminergic antagonist;
phenothiazine antipsychotic drug		1985201623.7low011010
flumazenil
2
ethyl ester;
imidazobenzodiazepine;
organofluorine compound		antidote to benzodiazepine poisoning;
GABA antagonist		1985201623.5low010010
fluorescite
2
benzoic acids;
cyclic ketone;
hydroxy monocarboxylic acid;
organic heterotricyclic compound;
phenols;
xanthene dye		fluorescent dye;
radioopaque medium		2000201616.0low001010
fluorouracil
1
nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic		201620168.0low000010
fluoxetine
1
(trifluoromethyl)benzenes;
aromatic ether;
secondary amino compound		201620168.0low000010
flurazepam
1
1,4-benzodiazepinone;
monofluorobenzenes;
organochlorine compound;
tertiary amino compound		anticonvulsant;
anxiolytic drug;
GABAA receptor agonist;
sedative		201620168.0low000010
flurbiprofen
1
fluorobiphenyl;
monocarboxylic acid		antipyretic;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
flutamide
1
(trifluoromethyl)benzenes;
monocarboxylic acid amide		androgen antagonist;
antineoplastic agent		201620168.0low000010
fomepizole
1
pyrazolesantidote;
EC 1.1.1.1 (alcohol dehydrogenase) inhibitor;
protective agent		201620168.0low000010
foscarnet
1
carboxylic acid;
one-carbon compound;
phosphonic acids		antiviral drug;
geroprotector;
HIV-1 reverse transcriptase inhibitor;
sodium-dependent Pi-transporter inhibitor		201620168.0low000010
furosemide
2
chlorobenzoic acid;
furans;
sulfonamide		environmental contaminant;
loop diuretic;
xenobiotic		2000201616.0low001010
gabapentin
1
gamma-amino acidanticonvulsant;
calcium channel blocker;
environmental contaminant;
xenobiotic		201620168.0low000010
gemfibrozil
1
aromatic etherantilipemic drug201620168.0low000010
2,5-dihydroxybenzoic acid
1
dihydroxybenzoic acidEC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
fungal metabolite;
human metabolite;
MALDI matrix material;
mouse metabolite		1977197747.0low010000
glafenine
1
aminoquinoline;
carboxylic ester;
glycol;
organochlorine compound;
secondary amino compound		inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
glimepiride
1
sulfonamide201620168.0low000010
glipizide
1
aromatic amide;
monocarboxylic acid amide;
N-sulfonylurea;
pyrazines		EC 2.7.1.33 (pantothenate kinase) inhibitor;
hypoglycemic agent;
insulin secretagogue		201620168.0low000010
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		201620168.0low000010
2-cyclopentyl-2-hydroxy-2-phenylacetic acid (1,1-dimethyl-3-pyrrolidin-1-iumyl) ester
1
benzenes201620168.0medium000010
granisetron
1
aromatic amide;
indazoles		201620168.0low000010
guaifenesin
1
methoxybenzenes201620168.0low000010
guanethidine
1
azocanes;
guanidines		adrenergic antagonist;
antihypertensive agent;
sympatholytic agent		201620168.0low000010
guanfacine
1
acetamides201620168.0low000010
guanidine
1
carboxamidine;
guanidines;
one-carbon compound		201620168.0low000010
haloperidol
2
aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist		1985201623.5low010010
hydralazine
1
azaarene;
hydrazines;
ortho-fused heteroarene;
phthalazines		antihypertensive agent;
vasodilator agent		201620168.0low000010
hydrochlorothiazide
1
benzothiadiazine;
organochlorine compound;
sulfonamide		antihypertensive agent;
diuretic;
environmental contaminant;
xenobiotic		201620168.0low000010
hydroflumethiazide
1
benzothiadiazine;
thiazide		antihypertensive agent;
diuretic		201620168.0low000010
hydroxychloroquine
1
aminoquinoline;
organochlorine compound;
primary alcohol;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
dermatologic drug		201620168.0low000010
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		201620168.0low000010
hydroxyzine
2
hydroxyether;
monochlorobenzenes;
N-alkylpiperazine		anticoronaviral agent;
antipruritic drug;
anxiolytic drug;
dermatologic drug;
H1-receptor antagonist		1985201623.5low010010
ibuprofen
2
monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
environmental contaminant;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
radical scavenger;
xenobiotic		2000201616.0low001010
phenelzine
1
primary amine201620168.0low000010
lidocaine
2
benzenes;
monocarboxylic acid amide;
tertiary amino compound		anti-arrhythmia drug;
drug allergen;
environmental contaminant;
local anaesthetic;
xenobiotic		1985201623.5low010010
ici 118551
1
indanes1985198539.0low010000
ifosfamide
1
ifosfamidesalkylating agent;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
xenobiotic		201620168.0low000010
imipramine
3
dibenzoazepineadrenergic uptake inhibitor;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor		1985201623.7low011010
amrinone
1
bipyridinesEC 3.1.4.* (phosphoric diester hydrolase) inhibitor201620168.0low000010
indapamide
1
indoles;
organochlorine compound;
sulfonamide		antihypertensive agent;
diuretic		201620168.0low000010
indomethacin
3
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		1985201623.7low011010
ioversol
1
amidobenzoic acid201620168.0low000010
iproniazid
1
carbohydrazide;
pyridines		201620168.0low000010
avapro
1
azaspiro compound;
biphenylyltetrazole		angiotensin receptor antagonist;
antihypertensive agent;
environmental contaminant;
xenobiotic		201620168.0low000010
1-methyl-3-isobutylxanthine
1
3-isobutyl-1-methylxanthine1985198539.0low010000
isocarboxazid
1
benzenes201620168.0low000010
isoniazid
1
carbohydrazideantitubercular agent;
drug allergen		201620168.0low000010
isoproterenol
1
catechols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
cardiotonic drug;
sympathomimetic agent		201620168.0low000010
isoxsuprine
1
alkylbenzene201620168.0low000010
isradipine
1
benzoxadiazole;
dihydropyridine;
isopropyl ester;
methyl ester		201620168.0low000010
itraconazole
1
piperazines201620168.0low000010
ketamine
2
cyclohexanones;
monochlorobenzenes;
secondary amino compound		analgesic;
environmental contaminant;
intravenous anaesthetic;
neurotoxin;
NMDA receptor antagonist;
xenobiotic		2007201612.5low000110
ketoconazole
1
dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine		201620168.0low000010
ketoprofen
2
benzophenones;
oxo monocarboxylic acid		antipyretic;
drug allergen;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
non-steroidal anti-inflammatory drug;
xenobiotic		2000201616.0low001010
ketorolac
1
amino acid;
aromatic ketone;
monocarboxylic acid;
pyrrolizines;
racemate		analgesic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
non-steroidal anti-inflammatory drug		201620168.0low000010
ketotifen
1
cyclic ketone;
olefinic compound;
organic heterotricyclic compound;
organosulfur heterocyclic compound;
piperidines;
tertiary amino compound		anti-asthmatic drug;
H1-receptor antagonist		2000200024.0low001000
labetalol
2
benzamides;
benzenes;
phenols;
primary carboxamide;
salicylamides;
secondary alcohol;
secondary amino compound		2000201616.0low001010
lamotrigine
2
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		2000201616.0low001010
lansoprazole
1
benzimidazoles;
pyridines;
sulfoxide		anti-ulcer drug;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor		201620168.0low000010
lauric acid
1
medium-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
antibacterial agent;
plant metabolite		2000200024.0low001000
leflunomide
1
(trifluoromethyl)benzenes;
isoxazoles;
monocarboxylic acid amide		antineoplastic agent;
antiparasitic agent;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
hepatotoxic agent;
immunosuppressive agent;
non-steroidal anti-inflammatory drug;
prodrug;
pyrimidine synthesis inhibitor;
tyrosine kinase inhibitor		201620168.0low000010
letrozole
1
nitrile;
triazoles		antineoplastic agent;
EC 1.14.14.14 (aromatase) inhibitor		201620168.0low000010
levallorphan
1
1988198836.0medium010000
lomefloxacin
1
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antimicrobial agent;
antitubercular agent;
photosensitizing agent		201620168.0low000010
lomustine
1
N-nitrosoureas;
organochlorine compound		alkylating agent;
antineoplastic agent		201620168.0low000010
loperamide
2
monocarboxylic acid amide;
monochlorobenzenes;
piperidines;
tertiary alcohol		anticoronaviral agent;
antidiarrhoeal drug;
mu-opioid receptor agonist		1985201623.5low010010
loratadine
1
benzocycloheptapyridine;
ethyl ester;
N-acylpiperidine;
organochlorine compound;
tertiary carboxamide		anti-allergic agent;
cholinergic antagonist;
geroprotector;
H1-receptor antagonist		201620168.0low000010
lorazepam
2
benzodiazepine2000201616.0low001010
losartan
2
biphenylyltetrazole;
imidazoles		angiotensin receptor antagonist;
anti-arrhythmia drug;
antihypertensive agent;
endothelin receptor antagonist		2000201616.0low001010
loxapine
2
dibenzooxazepineantipsychotic agent;
dopaminergic antagonist		2000201616.0low001010
maprotiline
1
anthracenes201620168.0low000010
mebendazole
1
aromatic ketone;
benzimidazoles;
carbamate ester		antinematodal drug;
microtubule-destabilising agent;
tubulin modulator		201620168.0low000010
mecamylamine
1
primary aliphatic amine201620168.0low000010
mechlorethamine
1
nitrogen mustard;
organochlorine compound		alkylating agent201620168.0low000010
meclizine
1
diarylmethane201620168.0low000010
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		201620168.0low000010
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		201620168.0low000010
memantine
1
adamantanes;
primary aliphatic amine		antidepressant;
antiparkinson drug;
dopaminergic agent;
neuroprotective agent;
NMDA receptor antagonist		201620168.0low000010
mepenzolate
1
diarylmethane201620168.0low000010
meperidine
3
ethyl ester;
piperidinecarboxylate ester;
tertiary amino compound		antispasmodic drug;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic		2000201912.3low001020
mephenytoin
1
imidazolidine-2,4-dioneanticonvulsant201620168.0low000010
mepivacaine
2
piperidinecarboxamidedrug allergen;
local anaesthetic		1985201623.5low010010
meprobamate
1
organic molecular entity201620168.0low000010
benzoic acid [2-methyl-2-(propylamino)propyl] ester
1
benzoate ester1985198539.0medium010000
mesalamine
2
amino acid;
aromatic amine;
monocarboxylic acid;
monohydroxybenzoic acid;
phenols		non-steroidal anti-inflammatory drug2000201616.0low001010
mesoridazine
1
phenothiazines;
sulfoxide;
tertiary amino compound		dopaminergic antagonist;
first generation antipsychotic		201620168.0low000010
metaproterenol
1
aralkylamino compound;
phenylethanolamines;
resorcinols;
secondary alcohol;
secondary amino compound		201620168.0low000010
metformin
1
guanidinesenvironmental contaminant;
geroprotector;
hypoglycemic agent;
xenobiotic		201620168.0low000010
methadone
2
benzenes;
diarylmethane;
ketone;
tertiary amino compound		201620177.5low000020
methazolamide
1
sulfonamide;
thiadiazoles		201620168.0low000010
methocarbamol
1
aromatic ether;
carbamate ester;
secondary alcohol		201620168.0low000010
methoxsalen
1
aromatic ether;
psoralens		antineoplastic agent;
cross-linking reagent;
dermatologic drug;
photosensitizing agent;
plant metabolite		201620168.0low000010
methyclothiazide
1
benzothiadiazine201620168.0low000010
methylphenidate
1
beta-amino acid ester;
methyl ester;
piperidines		201620168.0low000010
metoclopramide
1
benzamides;
monochlorobenzenes;
substituted aniline;
tertiary amino compound		antiemetic;
dopaminergic antagonist;
environmental contaminant;
gastrointestinal drug;
xenobiotic		201620168.0low000010
metolazone
1
organochlorine compound;
quinazolines;
sulfonamide		antihypertensive agent;
diuretic;
ion transport inhibitor		201620168.0low000010
metoprolol
2
aromatic ether;
propanolamine;
secondary alcohol;
secondary amino compound		antihypertensive agent;
beta-adrenergic antagonist;
environmental contaminant;
geroprotector;
xenobiotic		1985201623.5low010010
metronidazole
1
C-nitro compound;
imidazoles;
primary alcohol		antiamoebic agent;
antibacterial drug;
antimicrobial agent;
antiparasitic agent;
antitrichomonal drug;
environmental contaminant;
prodrug;
radiosensitizing agent;
xenobiotic		201620168.0low000010
metyrapone
1
aromatic ketoneantimetabolite;
diagnostic agent;
EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor		201620168.0low000010
mexiletine
2
aromatic ether;
primary amino compound		anti-arrhythmia drug2000201616.0low001010
mianserin
1
dibenzoazepineadrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
H1-receptor antagonist;
histamine agonist;
sedative;
serotonergic antagonist		1985198539.0low010000
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		201620168.0low000010
midodrine
1
amino acid amide;
aromatic ether;
secondary alcohol		alpha-adrenergic agonist;
prodrug;
sympathomimetic agent;
vasoconstrictor agent		201620168.0low000010
milrinone
1
bipyridines;
nitrile;
pyridone		cardiotonic drug;
EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor;
platelet aggregation inhibitor;
vasodilator agent		201620168.0low000010
minoxidil
1
dialkylarylamine;
tertiary amino compound		201620168.0low000010
mirtazapine
1
benzazepine;
tetracyclic antidepressant		alpha-adrenergic antagonist;
anxiolytic drug;
H1-receptor antagonist;
histamine antagonist;
oneirogen;
serotonergic antagonist		201620168.0low000010
mitotane
1
diarylmethane201620168.0low000010
mitoxantrone
2
dihydroxyanthraquinoneanalgesic;
antineoplastic agent		2000201616.0low001010
modafinil
1
monocarboxylic acid amide;
sulfoxide		201620168.0low000010
moxisylyte
1
monoterpenoid201620168.0low000010
nabumetone
1
methoxynaphthalene;
methyl ketone		cyclooxygenase 2 inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
prodrug		201620168.0low000010
nadolol
1
tetralins201620168.0low000010
nalidixic acid
1
1,8-naphthyridine derivative;
monocarboxylic acid;
quinolone antibiotic		antibacterial drug;
antimicrobial agent;
DNA synthesis inhibitor		201620168.0low000010
naratriptan
1
heteroarylpiperidine;
sulfonamide;
tryptamines		serotonergic agonist;
vasoconstrictor agent		201620168.0low000010
nefazodone
1
aromatic ether;
monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
triazoles		alpha-adrenergic antagonist;
analgesic;
antidepressant;
serotonergic antagonist;
serotonin uptake inhibitor		201620168.0low000010
nevirapine
1
cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
nialamide
1
organonitrogen compound;
organooxygen compound		201620168.0low000010
nicardipine
1
benzenes;
C-nitro compound;
diester;
dihydropyridine;
methyl ester;
tertiary amino compound		201620168.0low000010
nifedipine
2
C-nitro compound;
dihydropyridine;
methyl ester		calcium channel blocker;
human metabolite;
tocolytic agent;
vasodilator agent		1985201623.5low010010
nilutamide
1
(trifluoromethyl)benzenes;
C-nitro compound;
imidazolidinone		androgen antagonist;
antineoplastic agent		201620168.0low000010
nimesulide
1
aromatic ether;
C-nitro compound;
sulfonamide		cyclooxygenase 2 inhibitor;
non-steroidal anti-inflammatory drug		201620168.0low000010
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		201620168.0low000010
nisoldipine
2
C-nitro compound;
dicarboxylic acids and O-substituted derivatives;
diester;
dihydropyridine;
methyl ester		1985201623.5low010010
nitrendipine
1
C-nitro compound;
dicarboxylic acids and O-substituted derivatives;
diester;
dihydropyridine;
ethyl ester;
methyl ester		antihypertensive agent;
calcium channel blocker;
geroprotector;
vasodilator agent		1985198539.0low010000
nitroglycerin
1
nitroglycerolexplosive;
muscle relaxant;
nitric oxide donor;
prodrug;
tocolytic agent;
vasodilator agent;
xenobiotic		201620168.0low000010
nizatidine
1
1,3-thiazoles;
C-nitro compound;
carboxamidine;
organic sulfide;
tertiary amino compound		anti-ulcer drug;
cholinergic drug;
H2-receptor antagonist		201620168.0low000010
nomifensine
1
isoquinolinesdopamine uptake inhibitor201620168.0low000010
norfloxacin
1
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug;
DNA synthesis inhibitor;
environmental contaminant;
xenobiotic		201620168.0low000010
nortriptyline
3
organic tricyclic compound;
secondary amine		adrenergic uptake inhibitor;
analgesic;
antidepressant;
antineoplastic agent;
apoptosis inducer;
drug metabolite		1985201623.7low011010
ofloxacin
1
3-oxo monocarboxylic acid;
N-arylpiperazine;
N-methylpiperazine;
organofluorine compound;
oxazinoquinoline		201620168.0low000010
omeprazole
1
aromatic ether;
benzimidazoles;
pyridines;
sulfoxide		201620168.0low000010
ondansetron
1
carbazoles201620168.0low000010
orphenadrine
1
ether;
tertiary amino compound		antidyskinesia agent;
antiparkinson drug;
H1-receptor antagonist;
muscarinic antagonist;
muscle relaxant;
NMDA receptor antagonist;
parasympatholytic		201620168.0low000010
oxaprozin
1
1,3-oxazoles;
monocarboxylic acid		analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
oxazepam
2
1,4-benzodiazepinone;
organochlorine compound		anxiolytic drug;
environmental contaminant;
xenobiotic		2000201616.0low001010
oxethazaine
1
amino acid amide1985198539.0low010000
benoxinate
1
amino acid ester;
benzoate ester;
substituted aniline;
tertiary amino compound		drug allergen;
local anaesthetic;
topical anaesthetic		1985198539.0low010000
oxybutynin
1
acetylenic compound;
carboxylic ester;
racemate;
tertiary alcohol;
tertiary amino compound		antispasmodic drug;
calcium channel blocker;
local anaesthetic;
muscarinic antagonist;
muscle relaxant;
parasympatholytic		201620168.0low000010
oxyphenbutazone
1
phenols;
pyrazolidines		antimicrobial agent;
antineoplastic agent;
antipyretic;
drug metabolite;
gout suppressant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite		2000200024.0low001000
aminosalicylic acid
2
aminobenzoic acid;
phenols		antitubercular agent2000201616.0low001010
pamidronate
1
phosphonoacetic acid201620168.0low000010
pantoprazole
1
aromatic ether;
benzimidazoles;
organofluorine compound;
pyridines;
sulfoxide		anti-ulcer drug;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
environmental contaminant;
xenobiotic		201620168.0low000010
papaverine
2
benzylisoquinoline alkaloid;
dimethoxybenzene;
isoquinolines		antispasmodic drug;
vasodilator agent		1985201623.5low010010
pemoline
1
1,3-oxazolescentral nervous system stimulant201620168.0low000010
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		201620168.0low000010
pentobarbital
2
barbituratesGABAA receptor agonist1985201623.5low010010
pentoxifylline
1
oxopurine201620168.0low000010
perhexiline
1
piperidinescardiovascular drug201620168.0low000010
perphenazine
1
N-(2-hydroxyethyl)piperazine;
N-alkylpiperazine;
organochlorine compound;
phenothiazines		antiemetic;
dopaminergic antagonist;
phenothiazine antipsychotic drug		201620168.0low000010
pheniramine
2
pyridines;
tertiary amino compound		1985200031.5low011000
phenobarbital
3
barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative		1985201623.7low011010
phenolphthalein
1
phenols2000200024.0low001000
phenolsulfonphthalein
1
2,1-benzoxathiole;
arenesulfonate ester;
phenols;
sultone		acid-base indicator;
diagnostic agent;
two-colour indicator		2000200024.0low001000
phenoxybenzamine
2
aromatic amine1985201623.5low010010
phentermine
1
primary amineadrenergic agent;
appetite depressant;
central nervous system drug;
central nervous system stimulant;
dopaminergic agent;
sympathomimetic agent		201620168.0low000010
4-phenylbutyric acid
1
monocarboxylic acidantineoplastic agent;
apoptosis inducer;
EC 3.5.1.98 (histone deacetylase) inhibitor;
prodrug		201620168.0low000010
phenylbutazone
2
pyrazolidinesantirheumatic drug;
EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor;
metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug		1977200035.5low011000
pindolol
1
indoles;
secondary amine		antiglaucoma drug;
antihypertensive agent;
beta-adrenergic antagonist;
serotonergic antagonist;
vasodilator agent		201620168.0low000010
pioglitazone
1
aromatic ether;
pyridines;
thiazolidinediones		antidepressant;
cardioprotective agent;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hypoglycemic agent;
insulin-sensitizing drug;
PPARgamma agonist;
xenobiotic		201620168.0low000010
polythiazide
1
benzothiadiazine201620168.0low000010
practolol
1
acetamides;
ethanolamines;
propanolamine;
secondary alcohol;
secondary amino compound		anti-arrhythmia drug;
beta-adrenergic antagonist		1985198539.0low010000
duodote
1
pyridinium ionantidote to organophosphate poisoning;
antidote to sarin poisoning;
cholinergic drug;
cholinesterase reactivator		201620168.0low000010
pramoxine
1
aromatic ether;
morpholines		local anaesthetic1985198539.0low010000
praziquantel
1
isoquinolines201620168.0low000010
prazosin
2
aromatic ether;
furans;
monocarboxylic acid amide;
piperazines;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor		1985201623.5low010010
prilocaine
1
amino acid amide;
monocarboxylic acid amide		anticonvulsant;
local anaesthetic		1985198539.0low010000
primaquine
1
aminoquinoline;
aromatic ether;
N-substituted diamine		antimalarial201620168.0low000010
primidone
1
pyrimidoneanticonvulsant;
environmental contaminant;
xenobiotic		201620168.0low000010
proadifen
1
diarylmethane1985198539.0low010000
probenecid
2
benzoic acids;
sulfonamide		uricosuric drug2000201616.0low001010
procainamide
2
benzamidesanti-arrhythmia drug;
platelet aggregation inhibitor;
sodium channel blocker		1985201623.5low010010
procaine
1
benzoate ester;
substituted aniline;
tertiary amino compound		central nervous system depressant;
drug allergen;
local anaesthetic;
peripheral nervous system drug		1985198539.0low010000
procarbazine
1
benzamides;
hydrazines		antineoplastic agent201620168.0low000010
prochlorperazine
1
N-alkylpiperazine;
N-methylpiperazine;
organochlorine compound;
phenothiazines		alpha-adrenergic antagonist;
antiemetic;
cholinergic antagonist;
dopamine receptor D2 antagonist;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
first generation antipsychotic		201620168.0low000010
procyclidine
1
pyrrolidines;
tertiary alcohol		antidyskinesia agent;
antiparkinson drug;
muscarinic antagonist		201620168.0low000010
promazine
1
phenothiazines;
tertiary amine		antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
muscarinic antagonist;
phenothiazine antipsychotic drug;
serotonergic antagonist		1985198539.0low010000
promethazine
3
phenothiazines;
tertiary amine		anti-allergic agent;
anticoronaviral agent;
antiemetic;
antipruritic drug;
H1-receptor antagonist;
local anaesthetic;
sedative		1985201623.7low011010
propafenone
1
aromatic ketone;
secondary alcohol;
secondary amino compound		anti-arrhythmia drug201620168.0low000010
propantheline
1
xanthenes201620168.0low000010
proxymetacaine
1
benzoate ester1985198539.0low010000
propofol
2
phenolsanticonvulsant;
antiemetic;
intravenous anaesthetic;
radical scavenger;
sedative		2000201616.0low001010
propranolol
2
naphthalenes;
propanolamine;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
anxiolytic drug;
beta-adrenergic antagonist;
environmental contaminant;
human blood serum metabolite;
vasodilator agent;
xenobiotic		2000201616.0low001010
propyl gallate
1
trihydroxybenzoic acid2000200024.0low001000
protriptyline
2
carbotricyclic compoundantidepressant1985201623.5low010010
pyridostigmine
1
pyridinium ion201620168.0low000010
pyrilamine
2
aromatic ether;
ethylenediamine derivative		H1-receptor antagonist1985200031.5low011000
pyrimethamine
1
aminopyrimidine;
monochlorobenzenes		antimalarial;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor		201620168.0low000010
sch 16134
1
benzodiazepine201620168.0low000010
quetiapine
1
dibenzothiazepine;
N-alkylpiperazine;
N-arylpiperazine		adrenergic antagonist;
dopaminergic antagonist;
histamine antagonist;
second generation antipsychotic;
serotonergic antagonist		201620168.0low000010
1,2,5,8-tetrahydroxy anthraquinone
1
tetrahydroxyanthraquinoneEC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor2000200024.0low001000
rabeprazole
1
benzimidazoles;
pyridines;
sulfoxide		anti-ulcer drug;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor		201620168.0low000010
raloxifene
1
1-benzothiophenes;
aromatic ketone;
N-oxyethylpiperidine;
phenols		bone density conservation agent;
estrogen antagonist;
estrogen receptor modulator		201620168.0low000010
riluzole
1
benzothiazoles201620168.0low000010
rimantadine
1
alkylamine201620168.0low000010
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		201620168.0low000010
rizatriptan
1
tryptaminesanti-inflammatory drug;
serotonergic agonist;
vasoconstrictor agent		201620168.0low000010
4-(3-butoxy-4-methoxybenzyl)-2-imidazolidinone
1
methoxybenzenes1985198539.0low010000
rolipram
1
pyrrolidin-2-onesantidepressant;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor		1985198539.0low010000
ropinirole
1
indolones;
tertiary amine		antidyskinesia agent;
antiparkinson drug;
central nervous system drug;
dopamine agonist		201620168.0low000010
salicylamide
1
phenols;
salicylamides		antirheumatic drug;
non-narcotic analgesic		2000200024.0low001000
salicylsalicylic acid
1
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		201620168.0low000010
secobarbital
2
barbituratesanaesthesia adjuvant;
GABA modulator;
sedative		1985201623.5low010010
sibutramine
1
organochlorine compound;
tertiary amino compound		anti-obesity agent;
serotonin uptake inhibitor		201620168.0low000010
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		201620168.0low000010
risedronic acid
1
pyridines201620168.0low000010
sotalol
2
ethanolamines;
secondary alcohol;
secondary amino compound;
sulfonamide		anti-arrhythmia drug;
beta-adrenergic antagonist;
environmental contaminant;
xenobiotic		1985201623.5low010010
spiperone
1
aromatic ketone;
azaspiro compound;
organofluorine compound;
piperidines;
tertiary amino compound		alpha-adrenergic antagonist;
antipsychotic agent;
dopaminergic antagonist;
psychotropic drug;
serotonergic antagonist		1985198539.0low010000
imatinib
1
aromatic amine;
benzamides;
N-methylpiperazine;
pyridines;
pyrimidines		antineoplastic agent;
apoptosis inducer;
tyrosine kinase inhibitor		201620168.0low000010
vorinostat
1
dicarboxylic acid diamide;
hydroxamic acid		antineoplastic agent;
apoptosis inducer;
EC 3.5.1.98 (histone deacetylase) inhibitor		201620168.0low000010
succinylcholine
1
quaternary ammonium ion;
succinate ester		drug allergen;
muscle relaxant;
neuromuscular agent		201620168.0low000010
sulfadimethoxine
1
aromatic ether;
pyrimidines;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antiinfective agent;
antimicrobial agent;
drug allergen;
environmental contaminant;
xenobiotic		2000200024.0low001000
sulfamethizole
1
sulfonamide antibiotic;
sulfonamide;
thiadiazoles		antiinfective agent;
antimicrobial agent;
drug allergen;
EC 2.5.1.15 (dihydropteroate synthase) inhibitor		201620168.0low000010
sulfasalazine
1
201620168.0low000010
sulfathiazole
2
1,3-thiazoles;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antiinfective agent;
drug allergen;
EC 2.5.1.15 (dihydropteroate synthase) inhibitor;
environmental contaminant;
xenobiotic		2000201616.0low001010
sulfinpyrazone
1
pyrazolidines;
sulfoxide		uricosuric drug2000200024.0low001000
2-(octylamino)-1-[4-(propan-2-ylthio)phenyl]-1-propanol
1
alkylbenzene201620168.0low000010
sumatriptan
2
sulfonamide;
tryptamines		serotonergic agonist;
vasoconstrictor agent		201620196.5low000020
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		2000200024.0low001000
temazepam
2
benzodiazepine2000201616.0low001010
temozolomide
1
imidazotetrazine;
monocarboxylic acid amide;
triazene derivative		alkylating agent;
antineoplastic agent;
prodrug		201620168.0low000010
terazosin
1
furans;
piperazines;
primary amino compound;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
antineoplastic agent		201620168.0low000010
terbutaline
1
phenylethanolamines;
resorcinols		anti-asthmatic drug;
beta-adrenergic agonist;
bronchodilator agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
hypoglycemic agent;
sympathomimetic agent;
tocolytic agent		201620168.0low000010
terfenadine
1
diarylmethane2000200024.0low001000
tetracaine
1
benzoate ester;
tertiary amino compound		local anaesthetic1985198539.0low010000
thalidomide
1
phthalimides;
piperidones		201620168.0low000010
thiabendazole
1
1,3-thiazoles;
benzimidazole fungicide;
benzimidazoles		antifungal agrochemical;
antinematodal drug		201620168.0low000010
thioridazine
2
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		1985201623.5low010010
thiotepa
1
aziridines201620168.0low000010
thonzylamine
1
methoxybenzenes2000200024.0low001000
tiaprofenic acid
1
aromatic ketone;
monocarboxylic acid;
thiophenes		drug allergen;
non-steroidal anti-inflammatory drug		2000200024.0low001000
ticlopidine
1
monochlorobenzenes;
thienopyridine		anticoagulant;
fibrin modulating drug;
hematologic agent;
P2Y12 receptor antagonist;
platelet aggregation inhibitor		201620168.0low000010
tinidazole
1
imidazolesantiamoebic agent;
antibacterial drug;
antiparasitic agent;
antiprotozoal drug		201620168.0low000010
tiopronin
1
N-acyl-amino acid201620168.0low000010
tizanidine
1
benzothiadiazole;
imidazoles		alpha-adrenergic agonist;
muscle relaxant		201620168.0low000010
tolazamide
1
N-sulfonylureahypoglycemic agent;
potassium channel blocker		201620168.0low000010
tolazoline
1
imidazolesalpha-adrenergic antagonist;
antihypertensive agent;
vasodilator agent		1977197747.0low010000
tolbutamide
1
N-sulfonylureahuman metabolite;
hypoglycemic agent;
insulin secretagogue;
potassium channel blocker		201620168.0low000010
tolmetin
1
aromatic ketone;
monocarboxylic acid;
pyrroles		EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-steroidal anti-inflammatory drug		201620168.0low000010
ultram
1
aromatic ether;
tertiary alcohol;
tertiary amino compound		201620168.0low000010
tranexamic acid
1
amino acid201620168.0low000010
trazodone
2
monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
triazolopyridine		adrenergic antagonist;
antidepressant;
anxiolytic drug;
H1-receptor antagonist;
sedative;
serotonin uptake inhibitor		1985201623.5low010010
trequinsin
1
pyridopyrimidine1985198539.0low010000
triamterene
1
pteridinesdiuretic;
sodium channel blocker		201620168.0low000010
triazolam
1
triazolobenzodiazepinesedative201620168.0low000010
trifluoperazine
3
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		1985201623.7low011010
triflupromazine
1
organofluorine compound;
phenothiazines;
tertiary amine		anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic		2000200024.0low001000
trihexyphenidyl
1
amine201620168.0low000010
trimethadione
1
oxazolidinoneanticonvulsant;
geroprotector		201620168.0low000010
trimethobenzamide
1
benzamides;
tertiary amino compound		antiemetic201620168.0low000010
trimethoprim
1
aminopyrimidine;
methoxybenzenes		antibacterial drug;
diuretic;
drug allergen;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
environmental contaminant;
xenobiotic		201620168.0low000010
trimetrexate
1
201620168.0low000010
trimipramine
1
dibenzoazepine;
tertiary amino compound		antidepressant;
environmental contaminant;
xenobiotic		201620168.0low000010
tripelennamine
1
aromatic amine2000200024.0low001000
troglitazone
1
chromanes;
thiazolidinone		anticoagulant;
anticonvulsant;
antineoplastic agent;
antioxidant;
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
hypoglycemic agent;
platelet aggregation inhibitor;
vasodilator agent		201620168.0low000010
tyramine
1
monoamine molecular messenger;
primary amino compound;
tyramines		EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter		201620168.0low000010
delavirdine
1
aminopyridine;
indolecarboxamide;
N-acylpiperazine;
sulfonamide		antiviral drug;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
venlafaxine
1
cyclohexanols;
monomethoxybenzene;
tertiary alcohol;
tertiary amino compound		adrenergic uptake inhibitor;
analgesic;
antidepressant;
dopamine uptake inhibitor;
environmental contaminant;
serotonin uptake inhibitor;
xenobiotic		201620168.0low000010
vigabatrin
1
gamma-amino acidanticonvulsant;
EC 2.6.1.19 (4-aminobutyrate--2-oxoglutarate transaminase) inhibitor		201620168.0low000010
ici 204,219
1
carbamate ester;
indoles;
N-sulfonylcarboxamide		anti-asthmatic agent;
leukotriene antagonist		201620168.0low000010
zaleplon
1
nitrile;
pyrazolopyrimidine		anticonvulsant;
anxiolytic drug;
central nervous system depressant;
sedative		201620168.0low000010
zolpidem
1
imidazopyridinecentral nervous system depressant;
GABA agonist;
sedative		201620168.0low000010
zomepirac
1
aromatic ketone;
monocarboxylic acid;
monochlorobenzenes;
pyrroles		cardiovascular drug;
non-steroidal anti-inflammatory drug		2000200024.0low001000
zonisamide
1
1,2-benzoxazoles;
sulfonamide		anticonvulsant;
antioxidant;
central nervous system drug;
protective agent;
T-type calcium channel blocker		201620168.0low000010
cortisone acetate
1
corticosteroid hormone201620168.0low000010
mitomycin
1
mitomycinalkylating agent;
antineoplastic agent		201620168.0low000010
corticosterone
1
11beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite		2000200024.0low001000
prednisolone
1
11beta-hydroxy steroid;
17alpha-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(1),Delta(4)-steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		adrenergic agent;
anti-inflammatory drug;
antineoplastic agent;
drug metabolite;
environmental contaminant;
immunosuppressive agent;
xenobiotic		201620168.0low000010
estriol
1
16alpha-hydroxy steroid;
17beta-hydroxy steroid;
3-hydroxy steroid		estrogen;
human metabolite;
human xenobiotic metabolite;
mouse metabolite		2000200024.0low001000
reserpine
2
alkaloid ester;
methyl ester;
yohimban alkaloid		adrenergic uptake inhibitor;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
environmental contaminant;
first generation antipsychotic;
plant metabolite;
xenobiotic		1985201623.5low010010
phentolamine
2
imidazoles;
phenols;
substituted aniline;
tertiary amino compound		alpha-adrenergic antagonist;
vasodilator agent		1985201623.5low010010
hexobendine
1
trihydroxybenzoic acid1985198539.0low010000
sorbitol
1
glucitolcathartic;
Escherichia coli metabolite;
food humectant;
human metabolite;
laxative;
metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite;
sweetening agent		201620168.0low000010
2-aminophenol
1
aminophenolbacterial metabolite2000200024.0low001000
dichloroisoproterenol
1
1985198539.0low010000
3,4-dichlorobenzoic acid
1
chlorobenzoic acid1977197747.0medium010000
thyroxine
2
2-halophenol;
iodophenol;
L-phenylalanine derivative;
non-proteinogenic L-alpha-amino acid;
thyroxine zwitterion;
thyroxine		antithyroid drug;
human metabolite;
mouse metabolite;
thyroid hormone		2000201616.0low001010
dextroamphetamine
1
1-phenylpropan-2-amineadrenergic agent;
adrenergic uptake inhibitor;
dopamine uptake inhibitor;
dopaminergic agent;
neurotoxin;
sympathomimetic agent		201620168.0low000010
spironolactone
1
3-oxo-Delta(4) steroid;
oxaspiro compound;
steroid lactone;
thioester		aldosterone antagonist;
antihypertensive agent;
diuretic;
environmental contaminant;
xenobiotic		201620168.0low000010
aldosterone
1
11beta-hydroxy steroid;
18-oxo steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid hormone;
mineralocorticoid;
primary alpha-hydroxy ketone;
steroid aldehyde		human metabolite;
mouse metabolite		2000200024.0low001000
penicillamine
1
non-proteinogenic alpha-amino acid;
penicillamine		antirheumatic drug;
chelator;
copper chelator;
drug allergen		201620168.0low000010
cysteine
1
cysteine zwitterion;
cysteine;
L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid		EC 4.3.1.3 (histidine ammonia-lyase) inhibitor;
flour treatment agent;
human metabolite		201620168.0low000010
tetrahydrocortisol
1
11beta-hydroxy steroid;
17alpha-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3alpha-hydroxy steroid;
glucocorticoid;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		2000200024.0low001000
prednisone
2
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		2000201616.0low001010
tetrahydrocortisone
1
21-hydroxy steroid2000200024.0low001000
estrone
2
17-oxo steroid;
3-hydroxy steroid;
phenolic steroid;
phenols		antineoplastic agent;
bone density conservation agent;
estrogen;
human metabolite;
mouse metabolite		2000201616.0low001010
oxandrolone
1
17beta-hydroxy steroid;
3-oxo steroid;
anabolic androgenic steroid;
oxa-steroid		anabolic agent;
androgen		201620168.0low000010
androsterone
1
17-oxo steroid;
3alpha-hydroxy steroid;
androstanoid;
C19-steroid		androgen;
anticonvulsant;
human blood serum metabolite;
human metabolite;
human urinary metabolite;
mouse metabolite;
pheromone		2000200024.0low001000
etiocholanolone
1
17-oxo steroid;
3alpha-hydroxy steroid;
androstanoid		human metabolite;
mouse metabolite		2000200024.0low001000
dehydroepiandrosterone
1
17-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
androstanoid		androgen;
human metabolite;
mouse metabolite		2000200024.0low001000
hydroxyacetylaminofluorene
1
2-acetamidofluorenes2000200024.0low001000
penicillin g
1
penicillin allergen;
penicillin		antibacterial drug;
drug allergen;
epitope		201620168.0low000010
pilocarpine
1
pilocarpineantiglaucoma drug201620168.0low000010
triiodothyronine
2
2-halophenol;
amino acid zwitterion;
iodophenol;
iodothyronine		human metabolite;
mouse metabolite;
thyroid hormone		2000201616.0low001010
tetraethylammonium chloride
1
organic chloride salt;
quaternary ammonium salt		potassium channel blocker1985198539.0low010000
benz(a)anthracene
1
ortho-fused polycyclic arene;
tetraphenes		2000200024.0low001000
chloramphenicol
2
C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor		2000201616.0low001010
glutamine
1
amino acid zwitterion;
glutamine family amino acid;
glutamine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite		201620168.0low000010
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		201620168.0low000010
physostigmine
1
carbamate ester;
indole alkaloid		antidote to curare poisoning;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		201620168.0low000010
ethinyl estradiol
1
17-hydroxy steroid;
3-hydroxy steroid;
terminal acetylenic compound		xenoestrogen2000200024.0low001000
apomorphine
1
aporphine alkaloidalpha-adrenergic drug;
antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
emetic;
serotonergic drug		201620168.0low000010
aminopyrine
1
pyrazolone;
tertiary amino compound		antipyretic;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic		1977197747.0low010000
methyltestosterone
1
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
enone		anabolic agent;
androgen;
antineoplastic agent		201620168.0low000010
tetrabenazine
2
benzoquinolizine;
cyclic ketone;
tertiary amino compound		1985201623.5low010010
kanamycin a
1
kanamycinsbacterial metabolite201620168.0low000010
piperoxan
1
1985198539.0low010000
edetic acid
1
ethylenediamine derivative;
polyamino carboxylic acid;
tetracarboxylic acid		anticoagulant;
antidote;
chelator;
copper chelator;
geroprotector		201620168.0low000010
cysteamine
1
amine;
thiol		geroprotector;
human metabolite;
mouse metabolite;
radiation protective agent		201620168.0low000010
acetylcholine chloride
1
quaternary ammonium salt201620168.0low000010
mepazine
1
phenothiazines201620168.0low000010
cloxacillin
1
penicillin allergen;
penicillin;
semisynthetic derivative		antibacterial agent;
antibacterial drug		201620168.0low000010
4-nitrobenzoic acid
1
nitrobenzoic acid1977197747.0low010000
aniline
2
anilines;
primary arylamine		1977200035.5low011000
calcium acetate
1
calcium saltchelator201620168.0low000010
methionine
1
aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical		201620168.0low000010
desoxycorticosterone
1
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
mineralocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite		2000200024.0low001000
colchicine
1
alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen		201620168.0low000010
mebanazine
1
benzenes201620168.0low000010
oxacillin
1
penicillinantibacterial agent;
antibacterial drug		201620168.0low000010
norethindrone
1
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
terminal acetylenic compound;
tertiary alcohol		progestin;
synthetic oral contraceptive		2000200024.0low001000
norethynodrel
1
oxo steroid2000200024.0low001000
cycloserine
1
4-amino-1,2-oxazolidin-3-one;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic;
zwitterion		antiinfective agent;
antimetabolite;
antitubercular agent;
metabolite;
NMDA receptor agonist		201620168.0low000010
benziodarone
1
aromatic ketone201620168.0low000010
17-alpha-hydroxyprogesterone
1
17alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
tertiary alpha-hydroxy ketone		human metabolite;
metabolite;
mouse metabolite;
progestin		2000200024.0low001000
ampicillin
2
beta-lactam antibiotic;
penicillin allergen;
penicillin		antibacterial drug2000201616.0low001010
mannitol
1
mannitolallergen;
antiglaucoma drug;
compatible osmolytes;
Escherichia coli metabolite;
food anticaking agent;
food bulking agent;
food humectant;
food stabiliser;
food thickening agent;
hapten;
metabolite;
osmotic diuretic;
sweetening agent		201620168.0low000010
cytarabine
1
beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent		201620168.0low000010
4-hydroxypropiophenone
1
acetophenones1977197747.0low010000
alizarin
1
dihydroxyanthraquinonechromophore;
dye;
plant metabolite		2000200024.0low001000
nifenalol
1
C-nitro compound1985198539.0low010000
4-chlorobenzoic acid
1
monochlorobenzoic acidbacterial xenobiotic metabolite1977197747.0low010000
arginine
1
arginine;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		biomarker;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical		201620168.0low000010
perflutren
1
fluoroalkane;
fluorocarbon		201620168.0low000010
fluoxymesterone
1
11beta-hydroxy steroid;
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
anabolic androgenic steroid;
fluorinated steroid		anabolic agent;
antineoplastic agent		201620168.0low000010
phencyclidine
3
benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug		1992200724.0low001200
methsuximide
1
organic molecular entity201620168.0low000010
tromethamine
1
primary amino compound;
triol		buffer201620168.0low000010
linalool
1
monoterpenoid;
tertiary alcohol		antimicrobial agent;
fragrance;
plant metabolite;
volatile oil component		2000200024.0low001000
1,4-dihydroxyanthraquinone
1
dihydroxyanthraquinonedye2000200024.0low001000
cyclizine
1
N-alkylpiperazineantiemetic;
central nervous system depressant;
cholinergic antagonist;
H1-receptor antagonist;
local anaesthetic		2000200024.0low001000
methylprednisolone
1
6-methylprednisolone;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		adrenergic agent;
anti-inflammatory drug;
antiemetic;
environmental contaminant;
neuroprotective agent;
xenobiotic		201620168.0low000010
2,6-dihydroxyanthraquinone
1
dihydroxyanthraquinoneantimutagen;
plant metabolite		2000200024.0low001000
9,10-anthraquinone
1
anthraquinone2000200024.0low001000
brompheniramine
2
organobromine compound;
pyridines		anti-allergic agent;
H1-receptor antagonist		1985201623.5low010010
propoxycaine
1
benzoate ester1985198539.0low010000
dimethisoquin
1
isoquinolines1985198539.0medium010000
penicillin v
1
penicillin allergen;
penicillin		201620168.0low000010
isosorbide dinitrate
1
glucitol derivative;
nitrate ester		nitric oxide donor;
vasodilator agent		201620168.0low000010
2-nitrophenol
1
2-nitrophenols1977197747.0low010000
thymol
1
monoterpenoid;
phenols		volatile oil component2000200024.0low001000
1-naphthol
1
naphtholgenotoxin;
human xenobiotic metabolite		2000200024.0low001000
2-aminodiphenyl
1
2000200024.0low001000
2-phenylphenol
1
hydroxybiphenylsantifungal agrochemical;
environmental food contaminant		2000200024.0low001000
pseudoephedrine
1
phenylethanolamines;
secondary alcohol;
secondary amino compound		anti-asthmatic drug;
bronchodilator agent;
central nervous system drug;
nasal decongestant;
plant metabolite;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic		201620168.0low000010
diethylpropion
1
aromatic ketone;
tertiary amine		appetite depressant201620168.0low000010
quinoline
1
azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinolines		2000200024.0low001000
2-naphthylamine
1
naphthylaminecarcinogenic agent2000200024.0low001000
4-biphenylamine
1
aminobiphenylcarcinogenic agent2000200024.0low001000
4-phenylphenol
1
hydroxybiphenyls2000200024.0low001000
benzidine
1
biphenyls;
substituted aniline		carcinogenic agent2000200024.0low001000
4,4'-dihydroxybiphenyl
1
hydroxybiphenyls2000200024.0low001000
propylparaben
1
benzoate ester;
paraben;
phenols		antifungal agent;
antimicrobial agent		2000200024.0low001000
parethoxycaine
1
benzoate ester1985198539.0low010000
5-nitrosalicylic acid
1
4-nitrophenols;
monohydroxybenzoic acid		1977197747.0medium010000
butylphen
1
phenolsallergen2000200024.0low001000
3-hydroxybenzoic acid
1
monohydroxybenzoic acidbacterial metabolite;
plant metabolite		1977197747.0low010000
3-nitroaniline
1
1977197747.0low010000
methylparaben
1
parabenantifungal agent;
antimicrobial food preservative;
neuroprotective agent;
plant metabolite		2000200024.0low001000
4-isopropylphenol
1
phenolsflavouring agent2000200024.0low001000
4-hydroxyacetophenone
1
monohydroxyacetophenonefungal metabolite;
mouse metabolite;
plant metabolite		2000200024.0low001000
4-toluic acid
1
methylbenzoic acid1977197747.0low010000
4-nitroaniline
1
nitroanilinebacterial xenobiotic metabolite1977197747.0low010000
4-benzylphenol
1
2000200024.0medium001000
benzonatate
1
benzoate ester;
secondary amino compound;
substituted aniline		anaesthetic;
antitussive		201620168.0low000010
2-ethylhexanol
1
primary alcoholplant metabolite;
volatile oil component		2000200024.0low001000
4-toluidine
1
aminotoluene1977197747.0low010000
methylergonovine
1
ergoline alkaloid201620168.0low000010
2,2,2-trichloroethanol
1
chloroethanolmouse metabolite2000200024.0low001000
anthrarufin
1
dihydroxyanthraquinone2000200024.0medium001000
2-toluic acid
1
methylbenzoic acidxenobiotic metabolite2000200024.0low001000
2-chlorobenzoic acid
1
2-halobenzoic acid;
monochlorobenzoic acid		plant hormone;
plant metabolite		1977197747.0low010000
5-iodosalicylic acid
1
1977197747.0medium010000
ethyl-p-hydroxybenzoate
1
ethyl ester;
paraben		antifungal agent;
antimicrobial food preservative;
phytoestrogen;
plant metabolite		2000200024.0low001000
3-tert-butyl-4-hydroxyanisole
1
aromatic ether;
phenols		antioxidant;
human xenobiotic metabolite		2000200024.0low001000
3-nitrobenzoic acid
1
1977197747.0low010000
cinchophen
1
quinolines201620168.0low000010
3,5-diiodosalicylic acid
1
1977197747.0low010000
1-naphthylamine
1
naphthylaminehuman xenobiotic metabolite2000200024.0low001000
2-naphthol
1
naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger		2000200024.0low001000
shikimic acid
1
alpha,beta-unsaturated monocarboxylic acid;
cyclohexenecarboxylic acid;
hydroxy monocarboxylic acid		Escherichia coli metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite		2000200024.0low001000
citronellol
1
monoterpenoidplant metabolite2000200024.0low001000
hexanoic acid
1
medium-chain fatty acid;
straight-chain saturated fatty acid		human metabolite;
plant metabolite		2000200024.0low001000
pregnenolone
1
20-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
C21-steroid		human metabolite;
mouse metabolite		2000200024.0low001000
yohimbine
1
methyl 17-hydroxy-20xi-yohimban-16-carboxylatealpha-adrenergic antagonist;
dopamine receptor D2 antagonist;
serotonergic antagonist		1985198539.0low010000
2-chloroadenosine
1
purine nucleoside1985198539.0low010000
nafcillin
1
penicillin allergen;
penicillin		antibacterial drug201620168.0low000010
ditiocarb
1
dithiocarbamic acidschelator;
copper chelator		2000200024.0low001000
mequinol
1
methoxybenzenes;
phenols		metabolite2000200024.0low001000
methohexital
1
acetylenic compound;
barbiturates		drug allergen;
intravenous anaesthetic		201620168.0low000010
catechin
1
catechinantioxidant;
plant metabolite		2000200024.0low001000
phenetidine
1
aromatic ether;
primary amino compound;
substituted aniline		drug metabolite2000200024.0low001000
ephedrine
2
phenethylamine alkaloid;
phenylethanolamines		bacterial metabolite;
environmental contaminant;
nasal decongestant;
plant metabolite;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic		1977201627.5low010010
gamma-resorcylic acid
1
dihydroxybenzoic acidmetabolite1977197747.0low010000
aminophylline
1
mixturebronchodilator agent;
cardiotonic drug		201620168.0low000010
azacitidine
1
N-glycosyl-1,3,5-triazine;
nucleoside analogue		antineoplastic agent201620168.0low000010
3,5-dichlorosalicylic acid
1
chlorobenzoic acid1977197747.0low010000
5-chlorosalicylic acid
1
chlorobenzoic acid;
monochlorobenzenes;
monohydroxybenzoic acid		1977197747.0low010000
galantamine
2
benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite		2010201611.0low000110
nandrolone decanoate
1
steroid ester201620168.0low000010
4-hydroxyphenobarbital
1
barbiturates2000200024.0low001000
prenylamine
1
diarylmethane1985198539.0low010000
lithocholic acid
1
bile acid;
C24-steroid;
monohydroxy-5beta-cholanic acid		geroprotector;
human metabolite;
mouse metabolite		2000200024.0low001000
dextropropoxyphene
2
1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoatemu-opioid receptor agonist;
opioid analgesic		201620177.5low000020
chenodeoxycholic acid
2
bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human metabolite;
mouse metabolite		2000201616.0low001010
epitestosterone
1
17alpha-hydroxy steroid;
3-oxo-Delta(4) steroid;
androstanoid		androgen antagonist;
human metabolite		2000200024.0low001000
chrysophanic acid
1
dihydroxyanthraquinoneanti-inflammatory agent;
antiviral agent;
plant metabolite		2000200024.0low001000
bicuculline
1
benzylisoquinoline alkaloid;
isoquinoline alkaloid;
isoquinolines		agrochemical;
central nervous system stimulant;
GABA-gated chloride channel antagonist;
GABAA receptor antagonist;
neurotoxin		1985198539.0low010000
kainic acid
1
dicarboxylic acid;
L-proline derivative;
non-proteinogenic L-alpha-amino acid;
pyrrolidinecarboxylic acid		antinematodal drug;
excitatory amino acid agonist		2001200123.0low000100
carvacrol
1
botanical anti-fungal agent;
p-menthane monoterpenoid;
phenols		agrochemical;
antimicrobial agent;
flavouring agent;
TRPA1 channel agonist;
volatile oil component		2000200024.0low001000
4-hydroxybutyric acid
1
4-hydroxy monocarboxylic acid;
hydroxybutyric acid		general anaesthetic;
GHB receptor agonist;
neurotoxin;
sedative		201620168.0low000010
dihydroergotamine
1
ergot alkaloid;
semisynthetic derivative		dopamine agonist;
non-narcotic analgesic;
serotonergic agonist;
sympatholytic agent;
vasoconstrictor agent		201620168.0low000010
medroxyprogesterone
1
17alpha-hydroxy steroid;
20-oxo steroid;
3-oxo-Delta(4) steroid;
tertiary alpha-hydroxy ketone		contraceptive drug;
progestin;
synthetic oral contraceptive		201620168.0low000010
androstenediol
1
17beta-hydroxy steroid;
3beta-hydroxy-Delta(5)-steroid		androgen;
human metabolite;
mouse metabolite;
radiation protective agent		2000200024.0low001000
dihydrotestosterone
1
17beta-hydroxy steroid;
17beta-hydroxyandrostan-3-one;
3-oxo-5alpha-steroid		androgen;
Daphnia magna metabolite;
human metabolite;
mouse metabolite		2000200024.0low001000
dimenhydrinate
1
diarylmethane201620168.0low000010
1,2,3,4-tetrahydro-1-naphthalenol
1
2000200024.0medium001000
hexylcaine
1
benzoate ester1985198539.0low010000
piperocaine
1
benzoate ester1985198539.0low010000
diperodon
1
carbamate ester1985198539.0low010000
methamphetamine
1
amphetamines;
secondary amine		central nervous system stimulant;
environmental contaminant;
neurotoxin;
psychotropic drug;
xenobiotic		201620168.0low000010
cyclomethycaine
1
benzoate ester1985198539.0low010000
4-iodophenol
1
iodophenol2000200024.0low001000
levocarnitine
1
carnitineantilipemic drug;
nootropic agent;
nutraceutical;
Saccharomyces cerevisiae metabolite;
water-soluble vitamin (role)		201620168.0low000010
myristic acid
1
long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite		2000200024.0low001000
sulfanilylurea
1
benzenes;
sulfonamide		201620168.0low000010
3-nitrophenol
1
3-nitrophenols1977197747.0low010000
4-methyl-1-(1-methylethyl)-3-cyclohexen-1-ol
1
terpineol;
tertiary alcohol		anti-inflammatory agent;
antibacterial agent;
antineoplastic agent;
antioxidant;
antiparasitic agent;
apoptosis inducer;
plant metabolite;
volatile oil component		2000200024.0low001000
2,6-dinitrophenol
1
dinitrophenol1977197747.0low010000
lactulose
1
glycosylfructosegastrointestinal drug;
laxative		201620168.0low000010
3-hydroxyflavone
1
flavonols;
monohydroxyflavone		2000200024.0low001000
6-hydroxyquinoline
1
monohydroxyquinoline2000200024.0low001000
3-hydroxybiphenyl
1
hydroxybiphenyls2000200024.0medium001000
4-bromobenzoic acid
1
bromobenzoic acid1977197747.0medium010000
diphenylamine
1
aromatic amine;
bridged diphenyl fungicide;
secondary amino compound		antifungal agrochemical;
antioxidant;
carotogenesis inhibitor;
EC 1.3.99.29 [phytoene desaturase (zeta-carotene-forming)] inhibitor;
ferroptosis inhibitor;
radical scavenger		2000200024.0low001000
alpha-naphthoflavone
1
extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist;
aryl hydrocarbon receptor antagonist;
EC 1.14.14.14 (aromatase) inhibitor		2000200024.0low001000
pamabrom
1
201620168.0low000010
3,5-dinitrosalicylic acid
1
C-nitro compound;
monohydroxybenzoic acid		hapten1977197747.0low010000
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		201620168.0low000010
3-iodobenzoate
1
iodobenzoic acid1977197747.0medium010000
erythromycin
1
cyclic ketone;
erythromycin		201620168.0low000010
4-propylphenol
1
alkylbenzene2000200024.0medium001000
levonorgestrel
1
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
terminal acetylenic compound		contraceptive drug;
female contraceptive drug;
progestin;
synthetic oral contraceptive		201620168.0low000010
diphenoxylate
1
ethyl ester;
nitrile;
piperidinecarboxylate ester;
tertiary amine		antidiarrhoeal drug201620168.0low000010
hexafluoroisopropanol
1
organofluorine compound;
secondary alcohol		drug metabolite2000200024.0low001000
carcainium chloride
1
1985198539.0low010000
ethambutol
1
ethanolamines;
ethylenediamine derivative		antitubercular agent;
environmental contaminant;
xenobiotic		201620168.0low000010
vancomycin
1
glycopeptideantibacterial drug;
antimicrobial agent;
bacterial metabolite		201620168.0low000010
d-alpha tocopherol
2
alpha-tocopherolalgal metabolite;
antiatherogenic agent;
anticoagulant;
antioxidant;
antiviral agent;
EC 2.7.11.13 (protein kinase C) inhibitor;
immunomodulator;
micronutrient;
nutraceutical;
plant metabolite		2000201616.0low001010
ibufenac
1
monocarboxylic acidEC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
hepatotoxic agent;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
fenchol
1
2000200024.0low001000
4-n-Butylphenol
1
phenols2000200024.0medium001000
metaxalone
1
aromatic ether201620168.0low000010
4-hydroxyazobenzene
1
2000200024.0low001000
spectinomycin
1
cyclic acetal;
cyclic hemiketal;
cyclic ketone;
pyranobenzodioxin;
secondary alcohol;
secondary amino compound		antibacterial drug;
antimicrobial agent;
bacterial metabolite		201620168.0low000010
azacyclonol
1
diarylmethane1985198539.0low010000
4-nitrothiophenolate
1
2000200024.0low001000
5 alpha-androstane-3 alpha,17 beta-diol
1
androstane-3alpha,17beta-diolDaphnia magna metabolite;
human metabolite		2000200024.0low001000
dronabinol
1
benzochromene;
diterpenoid;
phytocannabinoid;
polyketide		cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic		201620168.0low000010
amiloride
1
aromatic amine;
guanidines;
organochlorine compound;
pyrazines		diuretic;
sodium channel blocker		201620168.0low000010
pimozide
1
benzimidazoles;
heteroarylpiperidine;
organofluorine compound		antidyskinesia agent;
dopaminergic antagonist;
first generation antipsychotic;
H1-receptor antagonist;
serotonergic antagonist		201620168.0low000010
menthol
1
p-menthan-3-olantipruritic drug;
antispasmodic drug;
antitussive		2000200024.0low001000
dexbrompheniramine
1
brompheniramineanti-allergic agent;
H1-receptor antagonist		201620168.0low000010
hydroxyphenytoin
1
imidazolidine-2,4-dione;
phenols		metabolite2000200024.0low001000
butoxamine
1
1985198539.0medium010000
stavudine
1
dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor		201620168.0low000010
dicloxacillin
1
dichlorobenzene;
penicillin		antibacterial drug201620168.0low000010
3,5-dibromosalicylic acid
1
1977197747.0medium010000
megestrol
1
17alpha-hydroxy steroid;
20-oxo steroid;
3-oxo-Delta(4) steroid;
tertiary alpha-hydroxy ketone		antineoplastic agent;
appetite enhancer;
contraceptive drug;
progestin;
synthetic oral contraceptive		201620168.0low000010
streptomycin
1
antibiotic antifungal drug;
antibiotic fungicide;
streptomycins		antibacterial drug;
antifungal agrochemical;
antimicrobial agent;
antimicrobial drug;
bacterial metabolite;
protein synthesis inhibitor		201620168.0low000010
cladribine
1
organochlorine compound;
purine 2'-deoxyribonucleoside		antineoplastic agent;
immunosuppressive agent		201620168.0low000010
mono-(2-ethylhexyl)phthalate
1
phthalic acid monoester2000200024.0low001000
carbenicillin
1
penicillin allergen;
penicillin		antibacterial drug201620168.0low000010
1-naphthalenemethanol
1
naphthylmethanolmouse metabolite2000200024.0medium001000
dexpropranolol
2
propranolol1985200031.5low011000
clomacran
1
acridines201620168.0medium000010
iprindole
1
indoles1985198539.0low010000
methenamine hippurate
1
N-acylglycine201620168.0low000010
olsalazine
1
azobenzenes;
dicarboxylic acid		non-steroidal anti-inflammatory drug;
prodrug		201620168.0low000010
sodium thiosulfate
1
inorganic sodium saltantidote to cyanide poisoning;
antifungal drug;
nephroprotective agent		201620168.0low000010
butylated hydroxyanisole
1
2000200024.0low001000
3-hydroxybenzo(a)pyrene
1
ortho- and peri-fused polycyclic arene2000200024.0low001000
selegiline
1
selegiline;
terminal acetylenic compound		geroprotector201620168.0low000010
4-n-Pentylphenol
1
phenols2000200024.0medium001000
clemastine
1
monochlorobenzenes;
N-alkylpyrrolidine		anti-allergic agent;
antipruritic drug;
H1-receptor antagonist;
muscarinic antagonist		201620168.0low000010
cephalexin
1
beta-lactam antibiotic allergen;
cephalosporin;
semisynthetic derivative		antibacterial drug201620168.0low000010
danazol
1
17beta-hydroxy steroid;
terminal acetylenic compound		anti-estrogen;
estrogen antagonist;
geroprotector		201620168.0low000010
9-hydroxybenzo(a)pyrene
1
ortho- and peri-fused polycyclic arene2000200024.0low001000
fenclozic acid
1
201620168.0low000010
laxagetten 4,4'-diacetoxydiphenylpyridylemethane
1
201620168.0medium000010
daunorubicin
2
aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite		2000201616.0low001010
fludarabine phosphate
1
nucleoside analogue;
organofluorine compound;
purine arabinonucleoside monophosphate		antimetabolite;
antineoplastic agent;
antiviral agent;
DNA synthesis inhibitor;
immunosuppressive agent;
prodrug		201620168.0low000010
alclofenac
1
aromatic ether;
monocarboxylic acid;
monochlorobenzenes		drug allergen;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0medium000010
bromocriptine
1
indole alkaloidantidyskinesia agent;
antiparkinson drug;
dopamine agonist;
hormone antagonist		201620168.0low000010
n-phenylethanolamine
1
aralkylamine2000200024.0low001000
4-ethylphenol
1
phenolsfungal xenobiotic metabolite2000200024.0low001000
oxyphenisatin
1
indoles201620168.0low000010
fludrocortisone
1
11beta-hydroxy steroid;
17alpha-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
fluorinated steroid;
mineralocorticoid		adrenergic agent;
anti-inflammatory drug		201620168.0low000010
ursodeoxycholic acid
2
bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid		human metabolite;
mouse metabolite		2000201616.0low001010
pregnanolone
1
3-hydroxy-5beta-pregnan-20-one;
3alpha-hydroxy steroid		human metabolite;
intravenous anaesthetic;
sedative		2000200024.0low001000
butylated hydroxytoluene
1
phenolsantioxidant;
ferroptosis inhibitor;
food additive;
geroprotector		2000200024.0low001000
carticaine
1
thiophenecarboxylic acid1985198539.0low010000
dexchlorpheniramine
1
chlorphenamine201620168.0low000010
clometacin
1
N-acylindole201620168.0low000010
cefazolin
1
beta-lactam antibiotic allergen;
cephalosporin;
tetrazoles;
thiadiazoles		antibacterial drug201620168.0low000010
amoxicillin
1
penicillin allergen;
penicillin		antibacterial drug201620168.0low000010
timolol
2
timololanti-arrhythmia drug;
antiglaucoma drug;
antihypertensive agent;
beta-adrenergic antagonist		1985201623.5low010010
tramadol
1
2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanoladrenergic 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		201920195.0low000010
oxcarbazepine
1
cyclic ketone;
dibenzoazepine		anticonvulsant;
drug allergen		201620168.0low000010
carbidopa
1
catechols;
hydrazines;
monocarboxylic acid		antiparkinson drug;
dopaminergic agent;
EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor		201620168.0low000010
moricizine
1
carbamate ester;
morpholines;
phenothiazines		anti-arrhythmia drug201620168.0low000010
amineptin
1
amino acid;
carbocyclic fatty acid;
carbotricyclic compound;
secondary amino compound		antidepressant;
dopamine uptake inhibitor		201620168.0low000010
zidovudine
2
azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor		2000201616.0low001010
pirprofen
1
pyrroline201620168.0low000010
paclitaxel
1
taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent		201620168.0low000010
etoposide
1
beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor		201620168.0low000010
substance p
1
peptideneurokinin-1 receptor agonist;
neurotransmitter;
vasodilator agent		201720177.0low000010
6-hydroxybenzo(a)pyrene
1
ortho- and peri-fused polycyclic arene2000200024.0medium001000
dobutamine
1
catecholamine;
secondary amine		beta-adrenergic agonist;
cardiotonic drug;
sympathomimetic agent		201620168.0low000010
butaclamol
1
organic heteropentacyclic compound1985198539.0low010000
penbutolol
1
ethanolamines201620168.0low000010
etidocaine
1
amino acid amidelocal anaesthetic1985198539.0low010000
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		201620168.0low000010
amikacin
1
alpha-D-glucoside;
amino cyclitol glycoside;
aminoglycoside;
carboxamide		antibacterial drug;
antimicrobial agent;
nephrotoxin		201620168.0low000010
cephradine
1
beta-lactam antibiotic allergen;
cephalosporin		antibacterial drug201620168.0low000010
ticrynafen
1
aromatic ether;
aromatic ketone;
dichlorobenzene;
monocarboxylic acid;
thiophenes		antihypertensive agent;
hepatotoxic agent;
loop diuretic		201620168.0low000010
methyldopa
1
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		alpha-adrenergic agonist;
antihypertensive agent;
hapten;
peripheral nervous system drug;
sympatholytic agent		201620168.0low000010
diltiazem
2
5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetateantihypertensive agent;
calcium channel blocker;
vasodilator agent		1985201623.5low010010
vecuronium
1
acetate ester;
androstane;
quaternary ammonium ion		drug allergen;
muscle relaxant;
neuromuscular agent;
nicotinic antagonist		201620168.0medium000010
dexibuprofen
1
ibuprofennon-narcotic analgesic;
non-steroidal anti-inflammatory drug		2000200024.0low001000
benoxaprofen
2
1,3-benzoxazoles;
monocarboxylic acid;
monochlorobenzenes		antipsoriatic;
antipyretic;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
hepatotoxic agent;
nephrotoxin;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
protein kinase C agonist		2000201616.0low001010
exifone
1
benzophenones201620168.0low000010
mefloquine
1
[2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanolantimalarial201620168.0low000010
meptazinol
1
azepanes201920195.0low000010
nitazoxanide
1
benzamides;
carboxylic ester		201620168.0low000010
sufentanil
2
anilide;
ether;
piperidines;
thiophenes		anaesthesia adjuvant;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic		201620196.5low000020
acarbose
1
tetrasaccharide derivativeEC 3.2.1.1 (alpha-amylase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
geroprotector;
hypoglycemic agent		201620168.0low000010
torsemide
1
aminopyridine;
N-sulfonylurea;
secondary amino compound		antihypertensive agent;
loop diuretic		201620168.0low000010
epirubicin
1
aminoglycoside;
anthracycline antibiotic;
anthracycline;
deoxy hexoside;
monosaccharide derivative;
p-quinones;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		antimicrobial agent;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor		201620168.0low000010
2-hydroxybenzo(a)pyrene
1
ortho- and peri-fused polycyclic arene2000200024.0medium001000
idarubicin
1
anthracycline antibiotic;
deoxy hexoside;
monosaccharide derivative		201620168.0low000010
piperacillin
1
penicillin allergen;
penicillin		antibacterial drug201620168.0low000010
paroxetine
1
aromatic ether;
benzodioxoles;
organofluorine compound;
piperidines		antidepressant;
anxiolytic drug;
hepatotoxic agent;
P450 inhibitor;
serotonin uptake inhibitor		201620168.0low000010
captopril
1
alkanethiol;
L-proline derivative;
N-acylpyrrolidine;
pyrrolidinemonocarboxylic acid		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor		201620168.0low000010
cefoperazone
1
cephalosporinantibacterial drug201620168.0low000010
Arbaclofen
1
organonitrogen compound;
organooxygen compound		1985198539.0low010000
atracurium
1
diester;
quaternary ammonium ion		muscle relaxant;
nicotinic antagonist		201620168.0low000010
pergolide
1
diamine;
methyl sulfide;
organic heterotetracyclic compound		antiparkinson drug;
dopamine agonist		201620168.0low000010
colforsin
1
acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist		1985198539.0low010000
cefadroxil anhydrous
1
cephalosporinantibacterial drug201620168.0low000010
fialuridine
1
201620168.0low000010
cefaclor anhydrous
1
cephalosporinantibacterial drug;
drug allergen		201620168.0low000010
alfentanil
1
monocarboxylic acid amide;
piperidines		central nervous system depressant;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic;
peripheral nervous system drug		201620168.0low000010
miglustat
1
piperidines;
tertiary amino compound		anti-HIV agent;
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor		201620168.0low000010
haloperidol decanoate
1
organic molecular entity201620168.0low000010
cefotetan
1
201620168.0low000010
lovastatin
1
delta-lactone;
fatty acid ester;
hexahydronaphthalenes;
polyketide;
statin (naturally occurring)		anticholesteremic drug;
antineoplastic agent;
Aspergillus metabolite;
prodrug		201620168.0low000010
tolrestat
1
naphthalenesEC 1.1.1.21 (aldehyde reductase) inhibitor201620168.0low000010
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		201620168.0low000010
balsalazide
1
201620168.0low000010
pravastatin
1
3-hydroxy carboxylic acid;
carbobicyclic compound;
carboxylic ester;
hydroxy monocarboxylic acid;
secondary alcohol;
statin (semi-synthetic)		anticholesteremic drug;
environmental contaminant;
metabolite;
xenobiotic		201620168.0low000010
cabergoline
1
N-acylureaantineoplastic agent;
antiparkinson drug;
dopamine agonist		201620168.0low000010
atomoxetine
1
aromatic ether;
secondary amino compound;
toluenes		adrenergic uptake inhibitor;
antidepressant;
environmental contaminant;
xenobiotic		201620168.0low000010
quinapril
1
dicarboxylic acid monoester;
ethyl ester;
isoquinolines;
tertiary carboxamide		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug		201620168.0low000010
alpidem
1
imidazoles201620168.0low000010
mifepristone
1
3-oxo-Delta(4) steroid;
acetylenic compound;
tertiary amino compound		abortifacient;
contraceptive drug;
hormone antagonist;
synthetic oral contraceptive		201620168.0low000010
fosphenytoin
1
imidazolidine-2,4-dione201620168.0low000010
ranolazine
1
aromatic amide;
monocarboxylic acid amide;
monomethoxybenzene;
N-alkylpiperazine;
secondary alcohol		201620168.0low000010
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		201620168.0low000010
esmolol
1
aromatic ether;
ethanolamines;
methyl ester;
secondary alcohol;
secondary amino compound		201620168.0low000010
adefovir
1
6-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent		201620168.0low000010
aromasil
1
17-oxo steroid;
3-oxo-Delta(1),Delta(4)-steroid		antineoplastic agent;
EC 1.14.14.14 (aromatase) inhibitor;
environmental contaminant;
xenobiotic		201620168.0low000010
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		201620168.0low000010
clopidogrel
1
methyl ester;
monochlorobenzenes;
thienopyridine		anticoagulant;
P2Y12 receptor antagonist;
platelet aggregation inhibitor		201620168.0low000010
cidofovir anhydrous
1
phosphonic acids;
pyrimidone		anti-HIV agent;
antineoplastic agent;
antiviral drug;
photosensitizing agent		201620168.0low000010
tiagabine
1
beta-amino acid;
piperidinemonocarboxylic acid;
tertiary amino compound;
thiophenes		anticonvulsant;
GABA reuptake inhibitor		201620168.0low000010
topotecan
1
pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor		201620168.0low000010
bromfenac
1
aromatic amino acid;
benzophenones;
organobromine compound;
substituted aniline		non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
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		201620168.0low000010
ibutilide
1
benzenes;
organic amino compound		201620168.0low000010
enadoline
1
2003200321.0low000100
aripiprazole
1
aromatic ether;
delta-lactam;
dichlorobenzene;
N-alkylpiperazine;
N-arylpiperazine;
quinolone		drug metabolite;
H1-receptor antagonist;
second generation antipsychotic;
serotonergic agonist		201620168.0low000010
remifentanil
1
alpha-amino acid ester;
anilide;
monocarboxylic acid amide;
piperidinecarboxylate ester		intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic;
sedative		201620168.0low000010
atorvastatin
1
aromatic amide;
dihydroxy monocarboxylic acid;
monofluorobenzenes;
pyrroles;
statin (synthetic)		environmental contaminant;
xenobiotic		201620168.0low000010
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		201620168.0low000010
duloxetine
1
duloxetine201620168.0low000010
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		201620168.0low000010
valsartan
1
biphenylyltetrazole;
monocarboxylic acid amide;
monocarboxylic acid		angiotensin receptor antagonist;
antihypertensive agent;
environmental contaminant;
xenobiotic		201620168.0low000010
ibandronic acid
1
201620168.0low000010
ziprasidone
1
1,2-benzisothiazole;
indolones;
organochlorine compound;
piperazines		antipsychotic agent;
dopaminergic antagonist;
histamine antagonist;
muscarinic antagonist;
psychotropic drug;
serotonergic antagonist		201620168.0low000010
zolmitriptan
1
oxazolidinone;
tryptamines		anti-inflammatory drug;
serotonergic agonist;
vasoconstrictor agent		201620168.0low000010
emtricitabine
1
monothioacetal;
nucleoside analogue;
organofluorine compound;
pyrimidone		antiviral drug;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
tasosartan
1
biphenyls201620168.0low000010
tiludronic acid
1
organochlorine compound201620168.0low000010
tirofiban
1
L-tyrosine derivative;
piperidines;
sulfonamide		anticoagulant;
fibrin modulating drug;
platelet glycoprotein-IIb/IIIa receptor antagonist		201620168.0low000010
capecitabine
1
carbamate ester;
cytidines;
organofluorine compound		antimetabolite;
antineoplastic agent;
prodrug		201620168.0low000010
adenosine
1
adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent		201620168.0low000010
octyl gallate
1
gallate esterfood antioxidant;
hypoglycemic agent;
plant metabolite		2000200024.0low001000
trovafloxacin
1
201620168.0low000010
cefprozil
1
cephalosporin;
semisynthetic derivative		antibacterial drug201620168.0medium000010
4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
1
stilbenoid2000200024.0low001000
efavirenz
1
acetylenic compound;
benzoxazine;
cyclopropanes;
organochlorine compound;
organofluorine compound		antiviral drug;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
nelfinavir
1
aryl sulfide;
benzamides;
organic heterobicyclic compound;
phenols;
secondary alcohol;
tertiary amino compound		antineoplastic agent;
HIV protease inhibitor		201620168.0low000010
fenofibric acid
1
aromatic ketone;
chlorobenzophenone;
monocarboxylic acid		drug metabolite;
marine xenobiotic metabolite		201620168.0low000010
2',7'-dichlorofluorescein
1
2-benzofuransfluorochrome2000200024.0low001000
plerixafor
1
azacycloalkane;
azamacrocycle;
benzenes;
crown amine;
secondary amino compound;
tertiary amino compound		anti-HIV agent;
antineoplastic agent;
C-X-C chemokine receptor type 4 antagonist;
immunological adjuvant		201620168.0low000010
amprenavir
1
carbamate ester;
sulfonamide;
tetrahydrofuryl ester		antiviral drug;
HIV protease inhibitor		201620168.0low000010
oseltamivir
1
acetamides;
amino acid ester;
cyclohexenecarboxylate ester;
primary amino compound		antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
environmental contaminant;
prodrug;
xenobiotic		201620168.0low000010
histamine phosphate
1
phosphate salthistamine agonist201620168.0low000010
16-hydroxytestosterone
1
16alpha-hydroxy steroid;
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
androstanoid;
C19-steroid;
diol;
secondary alcohol		androgen2000200024.0medium001000
tilbroquinol
1
organohalogen compound;
quinolines		201620168.0medium000010
bendamustine
1
benzimidazoles201620168.0low000010
droxicam
1
organic heterotricyclic compound;
pyridines		cyclooxygenase 1 inhibitor;
hepatotoxic agent;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
platelet aggregation inhibitor;
prodrug		201620168.0low000010
ebrotidine
1
sulfonamide201620168.0low000010
repaglinide
1
piperidines201620168.0low000010
telmisartan
1
benzimidazoles;
biphenyls;
carboxybiphenyl		angiotensin receptor antagonist;
antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
environmental contaminant;
xenobiotic		201620168.0low000010
2-methoxyestradiol
1
17beta-hydroxy steroid;
3-hydroxy steroid		angiogenesis modulating agent;
antimitotic;
antineoplastic agent;
human metabolite;
metabolite;
mouse metabolite		2000200024.0low001000
5,6,7,8-tetrahydro-1-naphthol
1
tetralins2000200024.0medium001000
alfatradiol
1
17alpha-hydroxy steroid;
3-hydroxy steroid;
estradiol		estrogen;
geroprotector		2000200024.0medium001000
sertraline
1
dichlorobenzene;
secondary amino compound;
tetralins		antidepressant;
serotonin uptake inhibitor		201620168.0low000010
zoledronic acid
1
1,1-bis(phosphonic acid);
imidazoles		bone density conservation agent201620168.0low000010
4-hydroxyquinoline
1
monohydroxyquinoline;
quinolone		2000200024.0low001000
opromazine
1
phenothiazines1985198539.0low010000
acamprosate
1
acetamides;
organosulfonic acid		environmental contaminant;
neurotransmitter agent;
xenobiotic		201620168.0low000010
isaxonine
1
aminopyrimidine201620168.0low000010
nebivolol
1
chromanes;
diol;
organofluorine compound;
secondary alcohol;
secondary amino compound		201620168.0medium000010
uk 68798
1
aromatic ether;
sulfonamide;
tertiary amino compound		anti-arrhythmia drug;
potassium channel blocker		201620168.0low000010
hp 873
1
1,2-benzoxazoles;
aromatic ether;
aromatic ketone;
methyl ketone;
monoamine;
organofluorine compound;
piperidines;
tertiary amino compound		dopaminergic antagonist;
second generation antipsychotic;
serotonergic antagonist		201620168.0low000010
dexrazoxane
1
razoxaneantineoplastic agent;
cardiovascular drug;
chelator;
immunosuppressive agent		201620168.0low000010
fenoxypropazine
1
aromatic ether201620168.0low000010
voriconazole
1
conazole antifungal drug;
difluorobenzene;
pyrimidines;
tertiary alcohol;
triazole antifungal drug		P450 inhibitor201620168.0low000010
aceclofenac
1
amino acid;
carboxylic ester;
dichlorobenzene;
monocarboxylic acid;
secondary amino compound		EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
nitrefazole
1
imidazoles201620168.0low000010
doripenem
1
carbapenems201620168.0low000010
atovaquone
1
hydroxy-1,2-naphthoquinone201620168.0low000010
5-methoxysalicylic acid
1
methoxysalicylic acidbacterial metabolite;
human urinary metabolite		1977197747.0low010000
rivastigmine
1
carbamate ester;
tertiary amino compound		cholinergic drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
neuroprotective agent		201620168.0low000010
frovatriptan
1
carbazoles201620168.0low000010
eletriptan
1
indoles;
N-alkylpyrrolidine;
sulfone		non-steroidal anti-inflammatory drug;
serotonergic agonist;
vasoconstrictor agent		201620168.0low000010
rosiglitazone
1
aminopyridine;
thiazolidinediones		EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
insulin-sensitizing drug		201620168.0low000010
bexarotene
1
benzoic acids;
naphthalenes;
retinoid		antineoplastic agent201620168.0low000010
clarithromycin
1
macrolide antibioticantibacterial drug;
environmental contaminant;
protein synthesis inhibitor;
xenobiotic		201620168.0low000010
moexipril
1
peptide201620168.0low000010
17-alpha-hydroxypregnenolone
1
17alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
3beta-hydroxy-Delta(5)-steroid;
hydroxypregnenolone;
tertiary alpha-hydroxy ketone		human metabolite;
mouse metabolite		2000200024.0low001000
5-(3-hydroxyphenyl)-5-phenylhydantoin
1
2000200024.0low001000
7-amino-4-methylcoumarin
1
7-aminocoumarinsfluorochrome2000200024.0low001000
mci 9038
1
peptide201620168.0low000010
11-hydroxyprogesterone, (11alpha)-isomer
1
11alpha-hydroxy steroid;
20-oxo steroid;
3-oxo-Delta(4) steroid		2000200024.0low001000
corynanthine
1
yohimban alkaloid1985198539.0low010000
brexanolone
1
3-hydroxy-5alpha-pregnan-20-oneantidepressant;
GABA modulator;
human metabolite;
intravenous anaesthetic;
sedative		2000200024.0low001000
3,5-diiodothyronine, (l)-isomer
1
phenylalanine derivative2000200024.0medium001000
phenylisopropyladenosine
1
aromatic amine;
benzenes;
hydrocarbyladenosine;
purine nucleoside;
secondary amino compound		adenosine A1 receptor agonist;
neuroprotective agent		1985198539.0low010000
harmol hydrochloride
1
2000200024.0medium001000
diosgenin
1
3beta-sterol;
hexacyclic triterpenoid;
sapogenin;
spiroketal		antineoplastic agent;
antiviral agent;
apoptosis inducer;
metabolite		2000200024.0low001000
sarsasapogenin, (3beta,5alpha,25r)-isomer
1
sapogeningout suppressant;
plant metabolite		2000200024.0medium001000
3 alpha,17 alpha-dihydroxy-5 beta-pregnan-20-one
1
17alpha-hydroxy steroid;
20-oxo steroid;
3alpha-hydroxy steroid;
C21-steroid;
corticosteroid hormone		human urinary metabolite2000200024.0medium001000
2-methoxyestriol
1
2000200024.0low001000
fulvestrant
1
17beta-hydroxy steroid;
3-hydroxy steroid;
organofluorine compound;
sulfoxide		antineoplastic agent;
estrogen antagonist;
estrogen receptor antagonist		201620168.0low000010
bosentan anhydrous
1
primary alcohol;
pyrimidines;
sulfonamide		antihypertensive agent;
endothelin receptor antagonist		201620168.0low000010
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
1
hydroxylamine;
imidazopyridine		carcinogenic agent;
genotoxin;
human xenobiotic metabolite;
mouse metabolite;
mutagen;
neurotoxin;
rat metabolite		2000200024.0low001000
perindopril
1
alpha-amino acid ester;
dicarboxylic acid monoester;
ethyl ester;
organic heterobicyclic compound		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor		201620168.0low000010
ecopipam
1
benzazepine2000200024.0low001000
tadalafil
1
benzodioxoles;
pyrazinopyridoindole		EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent		201620168.0low000010
ibuprofen, (r)-isomer
1
ibuprofen2000200024.0medium001000
11-hydroxytestosterone
1
11beta-hydroxy steroid;
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
androstanoid;
C19-steroid		bacterial xenobiotic metabolite;
human xenobiotic metabolite;
marine metabolite		2000200024.0low001000
norbuprenorphine
1
phenanthrenes2000200024.0low001000
paliperidone
1
1,2-benzoxazoles;
heteroarylpiperidine;
organofluorine compound;
pyridopyrimidine;
secondary alcohol		201620168.0low000010
nitisinone
1
(trifluoromethyl)benzenes;
C-nitro compound;
cyclohexanones;
mesotrione		EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor201620168.0low000010
clofarabine
1
adenosines;
organofluorine compound		antimetabolite;
antineoplastic agent		201620168.0low000010
benzo(a)pyrene-3,6-quinol
1
2000200024.0medium001000
pramipexole
1
benzothiazoles;
diamine		antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
radical scavenger		201620168.0low000010
valdecoxib
1
isoxazoles;
sulfonamide		antipyretic;
antirheumatic drug;
cyclooxygenase 2 inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		201620168.0low000010
almotriptan
1
indoles;
sulfonamide;
tertiary amine		non-steroidal anti-inflammatory drug;
serotonergic agonist;
vasoconstrictor agent		201620168.0low000010
gefitinib
1
aromatic ether;
monochlorobenzenes;
monofluorobenzenes;
morpholines;
quinazolines;
secondary amino compound;
tertiary amino compound		antineoplastic agent;
epidermal growth factor receptor antagonist		201620168.0low000010
desloratadine
1
benzocycloheptapyridineanti-allergic agent;
cholinergic antagonist;
drug metabolite;
H1-receptor antagonist		201620168.0low000010
w 7
1
1985198539.0medium010000
desvenlafaxine
1
cyclohexanols;
phenols;
tertiary amino compound		antidepressant;
drug metabolite;
marine xenobiotic metabolite		201620168.0low000010
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		201620168.0low000010
2-n-butyl-3-(dimethylamino)-5,6-methylenedioxyindene
1
1985198539.0medium010000
tamsulosin
1
5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamidealpha-adrenergic antagonist;
antineoplastic agent		201620168.0low000010
rufinamide
1
aromatic amide;
heteroarene		201620168.0low000010
olmesartan medoxomil
1
biphenyls201620168.0low000010
dexpanthenol
1
amino alcohol;
monocarboxylic acid amide		cholinergic drug;
provitamin		201620168.0low000010
fosamprenavir
1
sulfonamideprodrug201620168.0low000010
febuxostat
1
1,3-thiazolemonocarboxylic acid;
aromatic ether;
nitrile		EC 1.17.3.2 (xanthine oxidase) inhibitor201620168.0low000010
escitalopram
1
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrileantidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor		201620168.0low000010
10-propargyl-10-deazaaminopterin
1
N-acyl-L-glutamic acid;
pteridines;
terminal acetylenic compound		antimetabolite;
antineoplastic agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor		201620168.0low000010
docetaxel anhydrous
1
secondary alpha-hydroxy ketone;
tetracyclic diterpenoid		antimalarial;
antineoplastic agent;
photosensitizing agent		201620168.0low000010
atazanavir
1
carbohydrazideantiviral drug;
HIV protease inhibitor		201620168.0low000010
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		201620168.0low000010
ezetimibe
1
azetidines;
beta-lactam;
organofluorine compound		anticholesteremic drug;
antilipemic drug;
antimetabolite		201620168.0low000010
ertapenem
1
carbapenemcarboxylic acid;
pyrrolidinecarboxamide		antibacterial drug201620168.0low000010
cox 189
1
amino acid;
monocarboxylic acid;
organochlorine compound;
organofluorine compound;
secondary amino compound		cyclooxygenase 2 inhibitor;
non-steroidal anti-inflammatory drug		201620168.0low000010
conivaptan
1
benzazepineaquaretic;
vasopressin receptor antagonist		201620168.0low000010
moxifloxacin
1
aromatic ether;
cyclopropanes;
fluoroquinolone antibiotic;
pyrrolidinopiperidine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug201620168.0low000010
pralnacasan
1
201620168.0low000010
clevidipine
1
dihydropyridine201620168.0low000010
solifenacin
1
isoquinolines201620168.0low000010
dexmethylphenidate
1
methyl phenyl(piperidin-2-yl)acetateadrenergic agent201620168.0medium000010
naproxen
2
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		2000201616.0low001010
cinacalcet
1
(trifluoromethyl)benzenes;
naphthalenes;
secondary amino compound		calcimimetic;
P450 inhibitor		201620168.0low000010
lubiprostone
1
201620168.0low000010
telbivudine
1
pyrimidine 2'-deoxyribonucleosideantiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor		201620168.0low000010
cortolone
1
21-hydroxy steroid2000200024.0low001000
paromomycin
1
amino cyclitol glycoside;
aminoglycoside antibiotic		anthelminthic drug;
antibacterial drug;
antiparasitic agent;
antiprotozoal drug		201620168.0low000010
anidulafungin
1
antibiotic antifungal drug;
azamacrocycle;
echinocandin;
heterodetic cyclic peptide;
semisynthetic derivative		201620168.0low000010
rac 109
1
1985198539.0medium010000
17 alpha-hydroxyprogesterone caproate
1
corticosteroid hormone201620168.0low000010
varenicline
1
201620168.0low000010
fiduxosin
1
201620168.0low000010
atropine
2
1985201623.5low010010
erlotinib
1
aromatic ether;
quinazolines;
secondary amino compound;
terminal acetylenic compound		antineoplastic agent;
epidermal growth factor receptor antagonist;
protein kinase inhibitor		201620168.0low000010
dizocilpine
1
secondary amino compound;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist		1992199232.0low001000
carbocysteine
1
L-cysteine thioether;
non-proteinogenic L-alpha-amino acid		mucolytic2000200024.0low001000
etravirine
1
aminopyrimidine;
aromatic ether;
dinitrile;
organobromine compound		antiviral agent;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
dronedarone
1
1-benzofurans;
aromatic ether;
aromatic ketone;
sulfonamide;
tertiary amino compound		anti-arrhythmia drug;
environmental contaminant;
xenobiotic		201620168.0low000010
ramelteon
1
indanes201620168.0low000010
lapatinib
1
furans;
organochlorine compound;
organofluorine compound;
quinazolines		antineoplastic agent;
tyrosine kinase inhibitor		201620168.0low000010
darunavir
1
carbamate ester;
furofuran;
sulfonamide		antiviral drug;
HIV protease inhibitor		201620168.0low000010
deferasirox
1
benzoic acids;
monocarboxylic acid;
phenols;
triazoles		iron chelator201620168.0low000010
tbc-11251
1
benzodioxoles201620168.0low000010
tolvaptan
1
benzazepine;
benzenedicarboxamide		aquaretic;
vasopressin receptor antagonist		201620168.0low000010
sorafenib
1
(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
phenylureas;
pyridinecarboxamide		angiogenesis inhibitor;
anticoronaviral agent;
antineoplastic agent;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
ferroptosis inducer;
tyrosine kinase inhibitor		201620168.0low000010
lenalidomide
1
aromatic amine;
dicarboximide;
isoindoles;
piperidones		angiogenesis inhibitor;
antineoplastic agent;
immunomodulator		201620168.0low000010
regadenoson
1
purine nucleoside201620168.0low000010
lacosamide
1
N-acyl-amino acid201620168.0low000010
cholic acid
1
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
bile acid;
C24-steroid;
trihydroxy-5beta-cholanic acid		human metabolite;
mouse metabolite		2000200024.0low001000
vincaleukoblastine
1
acetate ester;
indole alkaloid fundamental parent;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
immunosuppressive agent;
microtubule-destabilising agent;
plant metabolite		201620168.0low000010
5 alpha-androstane-3 beta,17 beta-diol
1
17beta-hydroxy steroid;
3beta-hydroxy steroid;
androstane-3,17-diol		Daphnia magna metabolite;
human metabolite		2000200024.0low001000
cortol
1
21-hydroxy steroid2000200024.0medium001000
21-hydroxypregnenolone
1
21-hydroxy steroid;
hydroxypregnenolone;
primary alpha-hydroxy ketone		mouse metabolite2000200024.0medium001000
2-hydroxyestradiol
1
17beta-hydroxy steroid;
2-hydroxy steroid		carcinogenic agent;
human metabolite;
metabolite;
mouse metabolite;
prodrug		2000200024.0low001000
epietiocholanolone
1
17-oxo steroid;
3beta-hydroxy steroid;
androstanoid		androgen;
animal metabolite;
human blood serum metabolite;
mouse metabolite;
rat metabolite		2000200024.0medium001000
benzarone
1
1-benzofurans201620168.0low000010
estramustine
1
17beta-hydroxy steroid;
carbamate ester;
organochlorine compound		alkylating agent;
antineoplastic agent;
radiation protective agent		201620168.0low000010
norfentanyl
1
anilide;
monocarboxylic acid amide;
piperidines		drug metabolite;
opioid analgesic		201920195.0low000010
bortezomib
1
amino acid amide;
L-phenylalanine derivative;
pyrazines		antineoplastic agent;
antiprotozoal drug;
protease inhibitor;
proteasome inhibitor		201620168.0low000010
ritonavir
1
1,3-thiazoles;
carbamate ester;
carboxamide;
L-valine derivative;
ureas		antiviral drug;
environmental contaminant;
HIV protease inhibitor;
xenobiotic		201620168.0low000010
mr 1452
1
1988198836.0low010000
naringenin
1
(2S)-flavan-4-one;
naringenin		expectorant;
plant metabolite		2000200024.0low001000
oxytocin
1
heterodetic cyclic peptide;
peptide hormone		oxytocic;
vasodilator agent		201620168.0low000010
pentostatin
1
coformycinsantimetabolite;
antineoplastic agent;
Aspergillus metabolite;
bacterial metabolite;
EC 3.5.4.4 (adenosine deaminase) inhibitor		201620168.0low000010
2-hydroxyestrone
1
2-hydroxy steroid;
catechols		human metabolite2000200024.0low001000
strychnine
1
monoterpenoid indole alkaloid;
organic heteroheptacyclic compound		avicide;
cholinergic antagonist;
glycine receptor antagonist;
neurotransmitter agent;
rodenticide		1985198539.0low010000
quinidine
2
cinchona alkaloidalpha-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		1985201623.5low010010
meropenem
1
alpha,beta-unsaturated monocarboxylic acid;
carbapenemcarboxylic acid;
organic sulfide;
pyrrolidinecarboxamide		antibacterial agent;
antibacterial drug;
drug allergen		201620168.0low000010
griseofulvin
1
1-benzofurans;
antibiotic antifungal drug;
benzofuran antifungal drug;
organochlorine compound;
oxaspiro compound		antibacterial agent;
Penicillium metabolite		201620168.0low000010
cefoxitin
1
beta-lactam antibiotic allergen;
cephalosporin;
cephamycin;
semisynthetic derivative		antibacterial drug201620168.0low000010
saquinavir
1
L-asparagine derivative;
quinolines		antiviral drug;
HIV protease inhibitor		201620168.0low000010
pancuronium
1
acetate ester;
steroid ester		cholinergic antagonist;
muscle relaxant;
nicotinic antagonist		201620168.0low000010
abacavir
1
2,6-diaminopurinesantiviral drug;
drug allergen;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
epiandrosterone
1
17-oxo steroid;
3beta-hydroxy steroid;
androstanoid		androgen;
human metabolite		2000200024.0low001000
miglitol
1
piperidines201620168.0low000010
metyrosine
1
L-tyrosine derivative;
non-proteinogenic L-alpha-amino acid		antihypertensive agent;
EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor		201620168.0low000010
linezolid
1
acetamides;
morpholines;
organofluorine compound;
oxazolidinone		antibacterial drug;
protein synthesis inhibitor		201620168.0low000010
naringin
1
(2S)-flavan-4-one;
4'-hydroxyflavanones;
dihydroxyflavanone;
disaccharide derivative;
neohesperidoside		anti-inflammatory agent;
antineoplastic agent;
metabolite		2000200024.0low001000
1-alpha-terpineol
1
alpha-terpineolplant metabolite2000200024.0medium001000
clindamycin phosphate
1
201620168.0low000010
metazocine
1
benzazocine201720177.0low000010
diprenorphine
1
morphinane alkaloid2000200024.0low001000
eplerenone
1
3-oxo-Delta(4) steroid;
epoxy steroid;
gamma-lactone;
methyl ester;
organic heteropentacyclic compound;
oxaspiro compound;
steroid acid ester		aldosterone antagonist;
antihypertensive agent		201620168.0low000010
tolterodine
1
tertiary amineantispasmodic drug;
muscarinic antagonist;
muscle relaxant		201620168.0low000010
darifenacin
1
1-benzofurans;
monocarboxylic acid amide;
pyrrolidines		antispasmodic drug;
muscarinic antagonist		201620168.0low000010
ergosterol
1
3beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
ergostanoid;
phytosterols		fungal metabolite;
Saccharomyces cerevisiae metabolite		2000200024.0low001000
tretinoin
2
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		2000201616.0low001010
retinol
2
retinol;
vitamin A		human metabolite;
mouse metabolite;
plant metabolite		2000201616.0low001010
tacrolimus
1
macrolide lactambacterial metabolite;
immunosuppressive agent		201620168.0low000010
ferulic acid
1
ferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite		2000200024.0low001000
rosuvastatin
1
dihydroxy monocarboxylic acid;
monofluorobenzenes;
pyrimidines;
statin (synthetic);
sulfonamide		anti-inflammatory agent;
antilipemic drug;
cardioprotective agent;
CETP inhibitor;
environmental contaminant;
xenobiotic		201620168.0low000010
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		1985198539.0low010000
mycophenolic acid
2
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		2000201616.0low001010
clindamycin
1
201620168.0low000010
fosfomycin
1
epoxide;
phosphonic acids		antimicrobial agent;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor		201620168.0low000010
zithromax
1
macrolide antibioticantibacterial drug;
environmental contaminant;
xenobiotic		201620168.0low000010
diethylstilbestrol
2
olefinic compound;
polyphenol		antifungal agent;
antineoplastic agent;
autophagy inducer;
calcium channel blocker;
carcinogenic agent;
EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
endocrine disruptor;
xenoestrogen		1985200031.5low011000
octreotide
1
201620168.0medium000010
eptifibatide
1
homodetic cyclic peptide;
macrocycle;
organic disulfide		anticoagulant;
platelet aggregation inhibitor		201620168.0low000010
decitabine
1
2'-deoxyribonucleoside201620168.0low000010
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		201620168.0low000010
dactinomycin
1
actinomycinmutagen201620168.0low000010
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		201620168.0low000010
enkephalin, leucine
1
pentapeptide;
peptide zwitterion		analgesic;
delta-opioid receptor agonist;
human metabolite;
mu-opioid receptor agonist;
neurotransmitter;
rat metabolite		1982198242.0low010000
tenofovir
1
nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
posaconazole
1
aromatic ether;
conazole antifungal drug;
N-arylpiperazine;
organofluorine compound;
oxolanes;
triazole antifungal drug;
triazoles		trypanocidal drug201620168.0low000010
micafungin
1
antibiotic antifungal drug;
echinocandin		antiinfective agent201620168.0low000010
riboflavin
1
flavin;
vitamin B2		anti-inflammatory agent;
antioxidant;
cofactor;
Escherichia coli metabolite;
food colouring;
fundamental metabolite;
human urinary metabolite;
mouse metabolite;
photosensitizing agent;
plant metabolite		201620168.0low000010
sodium bicarbonate
1
one-carbon compound;
organic sodium salt		antacid;
food anticaking agent		201620168.0low000010
arsenic trioxide
1
arsenic oxideantineoplastic agent;
insecticide		201620168.0medium000010
norlevorphanol
1
2001200123.0low000100
sr 90107
1
201620168.0medium000010
meglumine iodipamide
1
organoammonium saltradioopaque medium201620168.0low000010
geraniol
1
3,7-dimethylocta-2,6-dien-1-ol;
monoterpenoid;
primary alcohol		allergen;
fragrance;
plant metabolite;
volatile oil component		2000200024.0low001000
thyrotropin-releasing hormone
1
peptide hormone;
tripeptide		human metabolite201620168.0low000010
rauwolscine
1
methyl 17-hydroxy-20xi-yohimban-16-carboxylate1985198539.0low010000
arginine vasopressin
1
vasopressincardiovascular drug;
hematologic agent;
mitogen		201620168.0low000010
s 1033
1
(trifluoromethyl)benzenes;
imidazoles;
pyridines;
pyrimidines;
secondary amino compound;
secondary carboxamide		anticoronaviral agent;
antineoplastic agent;
tyrosine kinase inhibitor		201620168.0low000010
propylthiouracil
1
pyrimidinethioneantidote to paracetamol poisoning;
antimetabolite;
antioxidant;
antithyroid drug;
carcinogenic agent;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
hormone antagonist		201620168.0low000010
chlorprothixene
1
chlorprothixene1985198539.0low010000
dienestrol
1
2000200024.0low001000
etomidate
1
ethyl ester;
imidazoles		intravenous anaesthetic;
sedative		201620168.0low000010
mercaptopurine
1
aryl thiol;
purines;
thiocarbonyl compound		anticoronaviral agent;
antimetabolite;
antineoplastic agent		201620168.0low000010
captax
1
aryl thiol;
benzothiazoles		carcinogenic agent;
metabolite		2000200024.0low001000
pyrantel
1
1,4,5,6-tetrahydropyrimidines;
carboxamidine;
thiophenes		antinematodal drug201620168.0low000010
flunarizine
1
diarylmethane1985198539.0low010000
thiothixene
3
N-methylpiperazineanticoronaviral agent1985201623.7medium011010
eszopiclone
1
zopiclonecentral nervous system depressant;
sedative		201620168.0low000010
benztropine
1
diarylmethane201620168.0low000010
methimazole
1
1,3-dihydroimidazole-2-thionesantithyroid drug201620168.0low000010
cinnarizine
1
diarylmethane;
N-alkylpiperazine;
olefinic compound		anti-allergic agent;
antiemetic;
calcium channel blocker;
geroprotector;
H1-receptor antagonist;
histamine antagonist;
muscarinic antagonist		1985198539.0low010000
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		201620168.0low000010
terbinafine
1
acetylenic compound;
allylamine antifungal drug;
enyne;
naphthalenes;
tertiary amine		EC 1.14.13.132 (squalene monooxygenase) inhibitor;
P450 inhibitor;
sterol biosynthesis inhibitor		201620168.0low000010
chlorogenic acid
1
cinnamate ester;
tannin		food component;
plant metabolite		2000200024.0low001000
thioguanine anhydrous
1
2-aminopurinesanticoronaviral agent;
antimetabolite;
antineoplastic agent		201620168.0low000010
succimer
1
dicarboxylic acid;
dithiol;
sulfur-containing carboxylic acid		chelator201620168.0low000010
digoxin
1
cardenolide glycoside;
steroid saponin		anti-arrhythmia drug;
cardiotonic drug;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
epitope		201620168.0low000010
streptozocin
1
201620168.0low000010
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		201620168.0low000010
ethionamide
1
pyridines;
thiocarboxamide		antilipemic drug;
antitubercular agent;
fatty acid synthesis inhibitor;
leprostatic drug;
prodrug		201620168.0low000010
cancidas
1
201620168.0low000010
lincomycin
1
carbohydrate-containing antibiotic;
L-proline derivative;
monocarboxylic acid amide;
pyrrolidinecarboxamide;
S-glycosyl compound		antimicrobial agent;
bacterial metabolite		201620168.0low000010
thiopental
1
barbituratesanticonvulsant;
drug allergen;
environmental contaminant;
intravenous anaesthetic;
sedative;
xenobiotic		1977197747.0low010000
ranitidine
1
C-nitro compound;
furans;
organic sulfide;
tertiary amino compound		anti-ulcer drug;
drug allergen;
environmental contaminant;
H2-receptor antagonist;
xenobiotic		201620168.0low000010
aplaviroc
1
201620168.0low000010
hmr 3647
1
201620168.0low000010
maraviroc
1
tropane alkaloid201620168.0low000010
toremifene
1
aromatic ether;
organochlorine compound;
tertiary amine		antineoplastic agent;
bone density conservation agent;
estrogen antagonist;
estrogen receptor modulator		201620168.0low000010
nelarabine
1
beta-D-arabinoside;
monosaccharide derivative;
purine nucleoside		antineoplastic agent;
DNA synthesis inhibitor;
prodrug		201620168.0low000010
dermatan sulfate
1
amino disaccharide;
glycosylgalactose derivative;
iduronic acids;
oligosaccharide sulfate		201620168.0low000010
dolasetron
1
indolyl carboxylic acid201620168.0low000010
orlistat
1
beta-lactone;
carboxylic ester;
formamides;
L-leucine derivative		anti-obesity agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor		201620168.0low000010
quinine
3
cinchona alkaloidantimalarial;
muscle relaxant;
non-narcotic analgesic		1977201631.3low020010
u-50488
4
dichlorobenzene;
monocarboxylic acid amide;
N-alkylpyrrolidine		analgesic;
antitussive;
calcium channel blocker;
diuretic;
kappa-opioid receptor agonist		2001201218.2low000310
sch 23390
1
benzazepine2000200024.0low001000
metazocine
1
1988198836.0medium010000
fospropofol
1
alkylbenzene201620168.0low000010
rasagiline
1
indanes;
secondary amine;
terminal acetylenic compound		EC 1.4.3.4 (monoamine oxidase) inhibitor;
neuroprotective agent		201620168.0low000010
dasatinib
1
1,3-thiazoles;
aminopyrimidine;
monocarboxylic acid amide;
N-(2-hydroxyethyl)piperazine;
N-arylpiperazine;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antineoplastic agent;
tyrosine kinase inhibitor		201620168.0low000010
digitoxigenin
1
14beta-hydroxy steroid;
3beta-hydroxy steroid		2000200024.0low001000
sitagliptin
1
triazolopyrazine;
trifluorobenzene		EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
environmental contaminant;
hypoglycemic agent;
serine proteinase inhibitor;
xenobiotic		201620168.0low000010
tolcapone
1
2-nitrophenols;
benzophenones;
catechols		antiparkinson drug;
EC 2.1.1.6 (catechol O-methyltransferase) inhibitor		201620168.0low000010
quercetin
1
7-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger		2000200024.0low001000
bilirubin
1
biladienes;
dicarboxylic acid		antioxidant;
human metabolite;
mouse metabolite		2000200024.0low001000
apigenin
1
trihydroxyflavoneantineoplastic agent;
metabolite		2000200024.0low001000
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		201620168.0low000010
scopoletin
1
hydroxycoumarinplant growth regulator;
plant metabolite		2000200024.0low001000
hymecromone
1
hydroxycoumarinantineoplastic agent;
hyaluronic acid synthesis inhibitor		2000200024.0low001000
vitamin d 2
2
hydroxy seco-steroid;
seco-ergostane;
vitamin D		bone density conservation agent;
nutraceutical;
plant metabolite;
rodenticide		2000201616.0low001010
cholecalciferol
1
D3 vitamins;
hydroxy seco-steroid;
seco-cholestane;
secondary alcohol;
steroid hormone		geroprotector;
human metabolite		2000200024.0low001000
amphotericin b
1
antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite		201620168.0low000010
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		201620168.0low000010
oxymetholone
1
201620168.0low000010
eprosartan
1
dicarboxylic acid;
imidazoles;
thiophenes		angiotensin receptor antagonist;
antihypertensive agent;
environmental contaminant;
xenobiotic		201620168.0low000010
montelukast
1
aliphatic sulfide;
monocarboxylic acid;
quinolines		anti-arrhythmia drug;
anti-asthmatic drug;
leukotriene antagonist		201620168.0low000010
mivacurium
1
isoquinolines201620168.0low000010
hemabate
1
201620168.0low000010
mycophenolate mofetil
1
carboxylic ester;
ether;
gamma-lactone;
phenols;
tertiary amino compound		anticoronaviral agent;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
immunosuppressive agent;
prodrug		201620168.0low000010
entacapone
1
2-nitrophenols;
catechols;
monocarboxylic acid amide;
nitrile		antidyskinesia agent;
antiparkinson drug;
central nervous system drug;
EC 2.1.1.6 (catechol O-methyltransferase) inhibitor		201620168.0low000010
paricalcitol
1
hydroxy seco-steroid;
seco-cholestane		antiparathyroid drug201620168.0low000010
esculetin
1
hydroxycoumarinantioxidant;
plant metabolite;
ultraviolet filter		2000200024.0low001000
7-hydroxycoumarin
1
hydroxycoumarinfluorescent probe;
food component;
plant metabolite		2000200024.0low001000
baicalein
1
trihydroxyflavoneangiogenesis inhibitor;
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 4.1.1.17 (ornithine decarboxylase) inhibitor;
ferroptosis inhibitor;
geroprotector;
hormone antagonist;
plant metabolite;
prostaglandin antagonist;
radical scavenger		2000200024.0low001000
chrysin
1
7-hydroxyflavonol;
dihydroxyflavone		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
EC 2.7.11.18 (myosin-light-chain kinase) inhibitor;
hepatoprotective agent;
plant metabolite		2000200024.0low001000
fisetin
1
3'-hydroxyflavonoid;
7-hydroxyflavonol;
tetrahydroxyflavone		anti-inflammatory agent;
antioxidant;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
metabolite;
plant metabolite		2000200024.0low001000
galangin
1
7-hydroxyflavonol;
trihydroxyflavone		antimicrobial agent;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
plant metabolite		2000200024.0low001000
7432 s
1
cephalosporin;
dicarboxylic acid		antibacterial drug201620168.0low000010
4-hydroxyestradiol
1
4-hydroxy steroidmetabolite2000200024.0low001000
isotretinoin
2
retinoic acidantineoplastic agent;
keratolytic drug;
teratogenic agent		2000201616.0low001010
epoprostenol
1
prostaglandins Imouse metabolite201620168.0low000010
indocyanine green
1
1,1-diunsubstituted alkanesulfonate;
benzoindole;
cyanine dye		201620168.0medium000010
triprolidine
1
N-alkylpyrrolidine;
olefinic compound;
pyridines		H1-receptor antagonist201620168.0low000010
pitavastatin
1
cyclopropanes;
dihydroxy monocarboxylic acid;
monofluorobenzenes;
quinolines;
statin (synthetic)		antioxidant201620168.0low000010
ethamolin
1
long-chain fatty acid201620168.0low000010
alatrofloxacin mesylate
1
201620168.0medium000010
hyodeoxycholic acid
1
5beta-cholanic acids;
6alpha,20xi-murideoxycholic acid;
bile acid;
C24-steroid		human metabolite;
mouse metabolite		2000200024.0low001000
codeine
8
morphinane alkaloid;
organic heteropentacyclic compound		antitussive;
drug allergen;
environmental contaminant;
opioid analgesic;
opioid receptor agonist;
prodrug;
xenobiotic		1982201922.8low031130
cyclosporine
1
homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite		201620168.0low000010
acitretin
1
acitretin;
alpha,beta-unsaturated monocarboxylic acid;
retinoid		keratolytic drug201620168.0low000010
estropipate
1
piperazinium salt;
steroid sulfate		201620168.0low000010
hydrocodone
3
morphinane-like compound;
organic heteropentacyclic compound		antitussive;
mu-opioid receptor agonist;
opioid analgesic		201220198.0low000030
hydromorphone
3
morphinane alkaloid;
organic heteropentacyclic compound		mu-opioid receptor agonist;
opioid analgesic		2000201912.3low001020
levetiracetam
1
pyrrolidin-2-onesanticonvulsant;
environmental contaminant;
xenobiotic		201620168.0low000010
ly 163892
1
carbacephem;
zwitterion		antibacterial drug;
antimicrobial agent		201620168.0low000010
nabilone
1
201620168.0low000010
nalmefene
1
morphinane alkaloid2000200024.0low001000
nalorphine
1
morphinane alkaloid2000200024.0low001000
naloxone
3
morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist		1988201622.7low011010
oxycodone
4
organic heteropentacyclic compound;
semisynthetic derivative		antitussive;
mu-opioid receptor agonist;
opioid analgesic		2000201912.8low001120
oxymorphone
3
morphinane alkaloid2000201912.3low001020
vitamin k 1
1
phylloquinones;
vitamin K		cofactor;
human metabolite;
plant metabolite		201620168.0low000010
sirolimus
1
antibiotic antifungal drug;
cyclic acetal;
cyclic ketone;
ether;
macrolide lactam;
organic heterotricyclic compound;
secondary alcohol		antibacterial drug;
anticoronaviral agent;
antineoplastic agent;
bacterial metabolite;
geroprotector;
immunosuppressive agent;
mTOR inhibitor		201620168.0low000010
topiramate
1
cyclic ketal;
ketohexose derivative;
sulfamate ester		anticonvulsant;
sodium channel blocker		201620168.0low000010
trospium chloride
1
201620168.0low000010
6alpha-hydroxy-17beta-estradiol
1
6alpha-hydroxy steroid2000200024.0medium001000
morphine
13
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		1982201921.9low041440
alpha-neoendorphin
1
201720177.0low000010
benzphetamine
1
amphetamines;
tertiary amine		adrenergic uptake inhibitor;
appetite depressant;
dopamine uptake inhibitor;
sympathomimetic agent		201620168.0low000010
deamino arginine vasopressin
1
heterodetic cyclic peptidediagnostic agent;
renal agent;
vasopressin receptor agonist		201620168.0low000010
dexmedetomidine
1
medetomidinealpha-adrenergic agonist;
analgesic;
non-narcotic analgesic;
sedative		201620168.0low000010
goserelin
1
organic molecular entity201620168.0low000010
nalbuphine
2
organic heteropentacyclic compoundmu-opioid receptor antagonist;
opioid analgesic		2000201616.0low001010
nateglinide
1
phenylalanine derivative201620168.0low000010
vinorelbine
1
acetate ester;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
ring assembly;
vinca alkaloid		antineoplastic agent;
photosensitizing agent		201620168.0low000010
silodosin
1
indolecarboxamide201620168.0low000010
cinnamyl alcohol
1
cinnamyl alcoholplant metabolite2000200024.0low001000
thebaine
1
morphinane alkaloid;
organic heteropentacyclic compound		201720177.0low000010
fluvoxamine
1
(trifluoromethyl)benzenes;
5-methoxyvalerophenone O-(2-aminoethyl)oxime		antidepressant;
anxiolytic drug;
serotonin uptake inhibitor		201620168.0low000010
su 11248
1
monocarboxylic acid amide;
pyrroles		angiogenesis inhibitor;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
immunomodulator;
neuroprotective agent;
vascular endothelial growth factor receptor antagonist		201620168.0low000010
(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		201620168.0low000010
codeine phosphate
1
1985198539.0low010000
levallorphan
1
morphinane alkaloid2010201014.0low000100
cyclorphan
7
2001201218.7high000610
naltrexone
6
cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic		1978201927.3low031020
morphine-6-glucuronide
1
morphinane alkaloid201720177.0low000010
dextromethorphan
3
6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthreneantitussive;
environmental contaminant;
neurotoxin;
NMDA receptor antagonist;
oneirogen;
prodrug;
xenobiotic		2007201910.0low000120
dextrorphan
5
morphinane alkaloid1976201924.6low020210
butorphanol
2
morphinane alkaloidantitussive;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic		2008201612.0low000110
methylnaltrexone
1
phenanthrenes201920195.0low000010
cefixime
1
cephalosporinantibacterial drug;
drug allergen		201620168.0low000010
lisinopril
1
dipeptideEC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor201620168.0low000010
benazepril
1
benzazepine;
dicarboxylic acid monoester;
ethyl ester;
lactam		EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug		201620168.0low000010
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		201620168.0low000010
verteporfin
1
201620168.0low000010
indinavir sulfate
1
dicarboxylic acid diamide;
N-(2-hydroxyethyl)piperazine;
piperazinecarboxamide		HIV protease inhibitor201620168.0low000010
zimeldine
2
styrenes1985201623.5low010010
enalapril
1
dicarboxylic acid monoester;
dipeptide		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
geroprotector;
prodrug		201620168.0low000010
trientine hydrochloride
1
201620168.0medium000010
n-methylscopolamine bromide
1
201620168.0low000010
sinomenine
1
morphinane alkaloid201720177.0low000010
bleomycin
1
bleomycinantineoplastic agent;
metabolite		201620168.0low000010
enkephalin, ala(2)-mephe(4)-gly(5)-
3
peptide2006201215.7low000210
enalaprilat anhydrous
1
dicarboxylic acid;
dipeptide		antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor		201620168.0low000010
6-o-monoacetylmorphine
1
morphinane alkaloid201720177.0low000010
normorphine
1
morphinane alkaloid2000200024.0low001000
ximelagatran
1
amidoxime;
azetidines;
carboxamide;
ethyl ester;
hydroxylamines;
secondary amino compound;
secondary carboxamide;
tertiary carboxamide		anticoagulant;
EC 3.4.21.5 (thrombin) inhibitor;
prodrug;
serine protease inhibitor		201620168.0low000010
cefuroxime
1
3-(carbamoyloxymethyl)cephalosporin;
furans;
oxime O-ether		drug allergen201620168.0low000010
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		201620168.0low000010
cefepime
1
cephalosporin;
oxime O-ether		antibacterial drug201620168.0low000010
pafuramidine
1
201620168.0low000010
ceftazidime
1
cephalosporin;
oxime O-ether		antibacterial drug;
drug allergen;
EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor		201620168.0low000010
3-methoxymorphinan
1
201920195.0medium000010
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		201620168.0low000010
morphine-3-glucuronide
1
morphinane alkaloid201720177.0low000010
chlornaltrexamine
1
1979197945.0low010000
acetylcodeine
1
201720177.0low000010
naltrindole benzofuran
1
morphinane alkaloid2000200024.0low001000
pregabalin
1
gamma-amino acidanticonvulsant;
calcium channel blocker		201620168.0low000010
alvimopan anhydrous
1
peptide201620168.0low000010
codeine-6-glucuronide
1
morphinane alkaloid201720177.0low000010
noroxycodone
1
phenanthrenes201920195.0low000010
aliskiren
1
monocarboxylic acid amide;
monomethoxybenzene		antihypertensive agent201620168.0low000010
naltrindole
1
isoquinolines2000200024.0low001000
famotidine
1
1,3-thiazoles;
guanidines;
sulfonamide		anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor		201620168.0low000010
cefotaxime
1
1,3-thiazoles;
cephalosporin;
oxime O-ether		antibacterial drug;
drug allergen		201620168.0low000010
aztreonam
1
beta-lactam antibiotic allergen;
monobactam		antibacterial drug;
drug allergen;
EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor		201620168.0low000010
cefpodoxime
1
carboxylic acid;
cephalosporin		antibacterial drug201620168.0low000010
palonosetron
1
azabicycloalkane;
delta-lactam;
organic heterotricyclic compound		antiemetic;
serotonergic antagonist		201620168.0low000010
rifaximin
1
acetate ester;
cyclic ketal;
lactam;
macrocycle;
organic heterohexacyclic compound;
rifamycins;
semisynthetic derivative		antimicrobial agent;
gastrointestinal drug;
orphan drug		201620168.0low000010
everolimus
1
cyclic acetal;
cyclic ketone;
ether;
macrolide lactam;
primary alcohol;
secondary alcohol		anticoronaviral agent;
antineoplastic agent;
geroprotector;
immunosuppressive agent;
mTOR inhibitor		201620168.0low000010
ixabepilone
1
1,3-thiazoles;
beta-hydroxy ketone;
epoxide;
lactam;
macrocycle		antineoplastic agent;
microtubule-destabilising agent		201620168.0low000010
19-hydroxycholesterol
1
cholestanoid2000200024.0medium001000
ceftizoxime
1
cephalosporinantibacterial drug201620168.0low000010
1-methyl-d-lysergic acid butanolamide
2
ergot alkaloid;
monocarboxylic acid amide		serotonergic antagonist;
sympatholytic agent;
vasoconstrictor agent		1985201623.5low010010
borneol
1
borneol2000200024.0medium001000
nitrofurantoin
1
imidazolidine-2,4-dione;
nitrofuran antibiotic;
organonitrogen heterocyclic antibiotic;
organooxygen heterocyclic antibiotic		antibacterial drug;
antiinfective agent;
hepatotoxic agent		201620168.0low000010
3,4-dichloro-n-methyl-n-(2-(1-pyrrolidinyl)cyclohexyl)-benzeneacetamide, (trans)-(-)-isomer
1
acetamides2006200618.0low000100
dantrolene
1
201620168.0low000010
cefdinir
1
cephalosporin;
ketoxime		antibacterial drug201620168.0low000010
etonogestrel
1
17beta-hydroxy steroid;
3-oxo-Delta(4) steroid;
terminal acetylenic compound		contraceptive drug;
female contraceptive drug;
progestin		201620168.0low000010
temsirolimus
1
macrolide lactam201620168.0low000010
dutasteride
1
(trifluoromethyl)benzenes;
aza-steroid;
delta-lactam		antihyperplasia drug;
EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor		201620168.0low000010
lu 208075
1
diarylmethane201620168.0low000010
bibx 1382bs
1
substituted aniline201620168.0low000010
fesoterodine
1
diarylmethane201620168.0low000010
gemifloxacin
1
1,8-naphthyridine derivative;
fluoroquinolone antibiotic;
monocarboxylic acid;
quinolone antibiotic		antibacterial drug;
antimicrobial agent;
topoisomerase IV inhibitor		201620168.0low000010
dexlansoprazole
1
benzimidazoles;
sulfoxide		201620168.0low000010
fosinopril
1
201620168.0medium000010
armodafinil
1
2-[(diphenylmethyl)sulfinyl]acetamidecentral nervous system stimulant;
eugeroic		201620168.0medium000010
sodium selenate
8
2001201218.4high000710
sincalide
1
oligopeptide201620168.0low000010
tapentadol
2
alkylbenzene201620196.5low000020
pentagastrin
1
organic molecular entity201620168.0low000010
cefditoren
1
carboxylic acid;
cephalosporin		antibacterial drug201620168.0low000010
norcodeine
2
morphinane alkaloid2000201715.5low001010
tan 67
1
quinolines201720177.0low000010
4-hydroxyestrone
1
17-oxo steroid;
3-hydroxy steroid;
4-hydroxy steroid;
catechols;
phenolic steroid		carcinogenic agent;
estrogen;
human urinary metabolite		2000200024.0low001000
pazopanib
1
aminopyrimidine;
indazoles;
sulfonamide		angiogenesis modulating agent;
antineoplastic agent;
tyrosine kinase inhibitor;
vascular endothelial growth factor receptor antagonist		201620168.0low000010
prasugrel hydrochloride
1
201620168.0low000010
11 beta-hydroxyandrosterone
1
3-hydroxy steroidandrogen2000200024.0low001000
2-hydroxyestriol
1
2000200024.0low001000
baci-im
1
homodetic cyclic peptide;
polypeptide;
zwitterion		antibacterial agent;
antimicrobial agent		201620168.0low000010
bms 477118
1
adamantanes;
azabicycloalkane;
monocarboxylic acid amide;
nitrile;
tertiary alcohol		EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor;
hypoglycemic agent		201620168.0low000010
nystatin a1
1
nystatins201620168.0low000010
adl 5859
1
201720177.0low000010
milnacipran
1
acetamides201620168.0low000010
scopolamine hydrobromide
2
1985201623.5low010010
ent-dextilidine
1
ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate201920195.0low000010
14-o-methyloxymorphone
1
2010201014.0medium000100
dynorphins
1
201720177.0low000010
bivalirudin
1
polypeptideanticoagulant;
EC 3.4.21.5 (thrombin) inhibitor		201620168.0low000010
enfuvirtide
1
201620168.0low000010
ganirelix
1
polypeptide201620168.0low000010
teriparatide
1
polypeptide201620168.0medium000010
cortistatin 14
1
201720177.0low000010
salmon calcitonin
1
heterodetic cyclic peptide;
peptide hormone;
polypeptide		bone density conservation agent;
metabolite		201620168.0medium000010
ly-146032
1
heterodetic cyclic peptide;
lipopeptide antibiotic;
lipopeptide;
macrocycle;
macrolide		antibacterial drug;
bacterial metabolite;
calcium-dependent antibiotics		201620168.0low000010
acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ilys-prolyl-alaninamide
1
polypeptide201620168.0low000010
exenatide
1
201620168.0low000010
bam 22p
1
201720177.0medium000010
mesna
1
organosulfonic acid201620168.0low000010
sodium lactate
1
lactate salt;
organic sodium salt		food acidity regulator;
food preservative		201620168.0low000010
sodium iothalamate
1
201620168.0low000010
cetrorelix
1
oligopeptideantineoplastic agent;
GnRH antagonist		201620168.0low000010
dynorphins
1
201720177.0low000010
ascorbic acid
1
ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent		201620168.0low000010
raltegravir
1
1,2,4-oxadiazole;
dicarboxylic acid amide;
hydroxypyrimidine;
monofluorobenzenes;
pyrimidone;
secondary carboxamide		antiviral drug;
HIV-1 integrase inhibitor		201620168.0low000010
novobiocin
1
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		2000200024.0low001000
tetracycline
2
2000201616.0low001010
oxytetracycline, anhydrous
1
201620168.0low000010
minocycline
1
201620168.0low000010
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		201620168.0low000010
mobic
1
1,3-thiazoles;
benzothiazine;
monocarboxylic acid amide		analgesic;
antirheumatic drug;
cyclooxygenase 2 inhibitor;
non-steroidal anti-inflammatory drug		201620168.0low000010
warfarin
1
benzenes;
hydroxycoumarin;
methyl ketone		201620168.0low000010
demeclocycline
1
201620168.0low000010
tipranavir
1
sulfonamideantiviral drug;
HIV protease inhibitor		201620168.0low000010
4-hydroxycoumarin
1
hydroxycoumarin2000200024.0low001000
tigecycline
1
201620168.0low000010
fertinex
1
201620168.0medium000010
entecavir
1
2-aminopurines;
oxopurine;
primary alcohol;
secondary alcohol		antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor		201620168.0low000010
acyclovir
1
2-aminopurines;
oxopurine		antimetabolite;
antiviral drug		201620168.0low000010
folic acid
1
folic acids;
N-acyl-amino acid		human metabolite;
mouse metabolite;
nutrient		201620168.0low000010
rifampin
2
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		2000201616.0low001010
clozapine
2
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		2000201616.0low001010
dacarbazine
1
dacarbazine201620168.0low000010
didanosine
1
purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor		201620168.0low000010
ganciclovir
1
2-aminopurines;
oxopurine		antiinfective agent;
antiviral drug		201620168.0low000010
valacyclovir
1
L-valyl esterantiviral drug201620168.0low000010
sildenafil
1
piperazines;
pyrazolopyrimidine;
sulfonamide		EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor;
vasodilator agent		201620168.0low000010
olanzapine
1
benzodiazepine;
N-arylpiperazine;
N-methylpiperazine		antiemetic;
dopaminergic antagonist;
histamine antagonist;
muscarinic antagonist;
second generation antipsychotic;
serotonergic antagonist;
serotonin uptake inhibitor		201620168.0low000010
vardenafil
1
imidazotriazine;
N-alkylpiperazine;
N-sulfonylpiperazine		EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
vasodilator agent		201620168.0low000010
allopurinol
1
nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger		201620168.0low000010
citrovorum factor
1
tetrahydrofolic acid201620168.0medium000010
leucovorin
1
formyltetrahydrofolic acidEscherichia coli metabolite;
mouse metabolite		201620168.0low000010
rifapentine
1
N-alkylpiperazine;
N-iminopiperazine;
rifamycins		antitubercular agent;
leprostatic drug		201620168.0low000010
bl 4162a
1
imidazoquinazolineanticoagulant;
antifibrinolytic drug;
cardiovascular drug;
platelet aggregation inhibitor		201620168.0low000010
tegaserod
1
carboxamidine;
guanidines;
hydrazines;
indoles		gastrointestinal drug;
serotonergic agonist		201620168.0low000010
norclozapine
1
dibenzodiazepine;
organochlorine compound;
piperazines		delta-opioid receptor agonist;
metabolite;
serotonergic antagonist		2000200024.0low001000
pemetrexed
1
N-acyl-L-glutamic acid;
pyrrolopyrimidine		antimetabolite;
antineoplastic agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
EC 2.1.1.45 (thymidylate synthase) inhibitor;
EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor		201620168.0low000010
valganciclovir
1
L-valyl ester;
purines		antiviral drug;
prodrug		201620168.0low000010
aprepitant
1
(trifluoromethyl)benzenes;
cyclic acetal;
morpholines;
triazoles		antidepressant;
antiemetic;
neurokinin-1 receptor antagonist;
peripheral nervous system drug;
substance P receptor antagonist		201620168.0low000010
fosaprepitant
1
(trifluoromethyl)benzenes;
cyclic acetal;
morpholines;
phosphoramide;
triazoles		antiemetic;
neurokinin-1 receptor antagonist;
prodrug		201620168.0low000010
rifabutin
1
201620168.0low000010
levomefolate calcium
1
organic calcium saltantidepressant201620168.0medium000010
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
gamma-aminobutyric acid
3
amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule		1976198244.3low030000
5-hydroxytryptophan
3
hydroxytryptophanhuman metabolite;
neurotransmitter		1971200739.0low020100
benzoic acid
1
benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite		1988198836.0low010000
bromide
1
halide anion;
monoatomic bromine		1999199925.0low001000
choline
4
cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae metabolite		1971197451.0low040000
citric acid, anhydrous
1
tricarboxylic acidantimicrobial agent;
chelator;
food acidity regulator;
fundamental metabolite		1987198737.0low110000
chlorine
2
halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite		1973198545.0low020000
salicylic acid
1
monohydroxybenzoic acidalgal metabolite;
antifungal agent;
antiinfective agent;
EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor;
keratolytic drug;
plant hormone;
plant metabolite		1964196460.0low010000
glycine
5
alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical		1976198245.8low050000
glycerol
2
alditol;
triol		algal metabolite;
detergent;
Escherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
solvent		1970197153.5low020000
histamine
5
aralkylamino compound;
imidazoles		human metabolite;
mouse metabolite;
neurotransmitter		1966199145.6low041000
methanol
3
alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite		1974199941.7low021000
nitrous oxide
5
gas molecular entity;
nitrogen oxide		analgesic;
bacterial metabolite;
food packaging gas;
food propellant;
general anaesthetic;
greenhouse gas;
inhalation anaesthetic;
NMDA receptor antagonist;
raising agent;
refrigerant;
vasodilator agent		1955198951.4low150000
orotic acid
1
pyrimidinemonocarboxylic acidEscherichia coli metabolite;
metabolite;
mouse metabolite		1972197252.0low010000
1-propanol
1
propan-1-ols;
short-chain primary fatty alcohol		metabolite;
protic solvent		1974197450.0low010000
quinolinic acid
2
pyridinedicarboxylic acidEscherichia coli metabolite;
human metabolite;
mouse metabolite;
NMDA receptor agonist		1987198836.5low020000
spermine
1
polyazaalkane;
tetramine		antioxidant;
fundamental metabolite;
immunosuppressive agent		1970197054.0low010000
uracil
4
pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite		1964197056.8low040000
2-amino-5-phosphonovalerate
1
non-proteinogenic alpha-amino acidNMDA receptor antagonist1988198836.0low010000
3-methoxymorphinan
3
1980201828.0low011010
phenytoin
5
imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent		1986198936.4low050000
hydroxyindoleacetic acid
1
indole-3-acetic acidsdrug metabolite;
human metabolite;
mouse metabolite		1975197549.0low010000
acetaminophen
8
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		1978199838.5low171000
albuterol
3
phenols;
phenylethanolamines;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
environmental contaminant;
xenobiotic		1986199036.3low321000
theophylline
1
dimethylxanthineadenosine 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		1974197450.0low010000
amitriptyline
2
carbotricyclic compound;
tertiary amine		adrenergic uptake inhibitor;
antidepressant;
environmental contaminant;
tropomyosin-related kinase B receptor agonist;
xenobiotic		1967199841.5low011000
antipyrine
2
pyrazoloneantipyretic;
cyclooxygenase 3 inhibitor;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic		1969198845.5low020000
aspirin
9
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		1964199852.0low181000
bethanechol
1
carbamate ester;
quaternary ammonium ion		muscarinic agonist1987198737.0low010000
bromhexine
1
organobromine compound;
substituted aniline;
tertiary amino compound		mucolytic1975197549.0low010000
caffeine
3
purine alkaloid;
trimethylxanthine		adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic		1986198936.0low030000
carbetapentane
2
benzenes1986198737.5low020000
chloral hydrate
1
aldehyde hydrate;
ethanediol;
organochlorine compound		general anaesthetic;
mouse metabolite;
sedative;
xenobiotic		1979197945.0low010000
chlordiazepoxide
3
benzodiazepine1969198649.3low030000
chloroquine
1
aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug		1969196955.0low010000
chlorpheniramine
3
monochlorobenzenes;
pyridines;
tertiary amino compound		anti-allergic agent;
antidepressant;
antipruritic drug;
H1-receptor antagonist;
histamine antagonist;
serotonin uptake inhibitor		1984198937.0low030000
chlorpromazine
7
organochlorine compound;
phenothiazines;
tertiary amine		anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug		1966199051.0low161000
cimetidine
1
aliphatic sulfide;
guanidines;
imidazoles;
nitrile		adjuvant;
analgesic;
anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor		1989198935.0low010000
clonidine
3
clonidine;
imidazoline		1982198739.0low030000
cyproheptadine
1
piperidines;
tertiary amine		anti-allergic agent;
antipruritic drug;
gastrointestinal drug;
H1-receptor antagonist;
serotonergic antagonist		1984198440.0low110000
debrisoquin
8
carboxamidine;
isoquinolines		adrenergic agent;
antihypertensive agent;
human metabolite;
sympatholytic agent		1984198936.8low180000
desipramine
4
dibenzoazepine;
secondary amino compound		adrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
cholinergic antagonist;
drug allergen;
EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
serotonin uptake inhibitor		1969200735.8low020200
amphetamine
6
primary amine1964197454.7low060000
diazepam
4
1,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic		1970199044.5low131000
diphenhydramine
4
ether;
tertiary amino compound		anti-allergic agent;
antidyskinesia agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
antitussive;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
oneirogen;
sedative		1975198743.0low140000
thiorphan
1
N-acyl-amino acid2000200024.0low001000
doxylamine
4
pyridines;
tertiary amine		anti-allergic agent;
antiemetic;
antitussive;
cholinergic antagonist;
H1-receptor antagonist;
histamine antagonist;
sedative		1975198940.2low040000
ether
1
ether;
volatile organic compound		inhalation anaesthetic;
non-polar solvent;
refrigerant		1979197945.0low010000
fentanyl
16
anilide;
monocarboxylic acid amide;
piperidines		adjuvant;
anaesthesia adjuvant;
anaesthetic;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic		1968202242.9low2131101
guaifenesin
4
methoxybenzenes1979198840.5low040000
guanethidine
1
azocanes;
guanidines		adrenergic antagonist;
antihypertensive agent;
sympatholytic agent		1969196955.0low010000
haloperidol
5
aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist		1975199038.0low041000
halothane
2
haloalkane;
organobromine compound;
organochlorine compound;
organofluorine compound		inhalation anaesthetic1979198940.0low020000
hexobarbital
1
barbiturates1974197450.0low010000
lidocaine
3
benzenes;
monocarboxylic acid amide;
tertiary amino compound		anti-arrhythmia drug;
drug allergen;
environmental contaminant;
local anaesthetic;
xenobiotic		1974200040.7low021000
imipramine
1
dibenzoazepineadrenergic uptake inhibitor;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor		1969196955.0low010000
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		1969196955.0low010000
1-methyl-3-isobutylxanthine
1
3-isobutyl-1-methylxanthine1996199628.0low001000
isocarboxazid
1
benzenes1988198836.0low010000
isoproterenol
4
catechols;
secondary alcohol;
secondary amino compound		beta-adrenergic agonist;
bronchodilator agent;
cardiotonic drug;
sympathomimetic agent		1970199146.0low031000
ketamine
6
cyclohexanones;
monochlorobenzenes;
secondary amino compound		analgesic;
environmental contaminant;
intravenous anaesthetic;
neurotoxin;
NMDA receptor antagonist;
xenobiotic		1980199637.2low042000
ketorolac
1
amino acid;
aromatic ketone;
monocarboxylic acid;
pyrrolizines;
racemate		analgesic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
non-steroidal anti-inflammatory drug		1998199826.0low001000
ketotifen
1
cyclic ketone;
olefinic compound;
organic heterotricyclic compound;
organosulfur heterocyclic compound;
piperidines;
tertiary amino compound		anti-asthmatic drug;
H1-receptor antagonist		1989198935.0low010000
loperamide
3
monocarboxylic acid amide;
monochlorobenzenes;
piperidines;
tertiary alcohol		anticoronaviral agent;
antidiarrhoeal drug;
mu-opioid receptor agonist		1979198642.3low030000
mecamylamine
1
primary aliphatic amine1969196955.0low010000
meperidine
40
ethyl ester;
piperidinecarboxylate ester;
tertiary amino compound		antispasmodic drug;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic		1963199851.1low4391000
mephenesin
1
aromatic ether;
glycerol ether		1963196361.0low010000
mephenytoin
3
imidazolidine-2,4-dioneanticonvulsant1988199035.3low121000
meprobamate
1
organic molecular entity1963196361.0low010000
methadone
88
benzenes;
diarylmethane;
ketone;
tertiary amino compound		1953202045.2low3716920
methoxyphenamine
1
amphetaminesbeta-adrenergic agonist;
bronchodilator agent		1984198440.0low010000
mexiletine
1
aromatic ether;
primary amino compound		anti-arrhythmia drug1990199034.0low001000
ethylmaleimide
5
maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor		1973198846.0low050000
nefazodone
1
aromatic ether;
monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
triazoles		alpha-adrenergic antagonist;
analgesic;
antidepressant;
serotonergic antagonist;
serotonin uptake inhibitor		2007200717.0low000100
neostigmine
2
quaternary ammonium ionantidote to curare poisoning;
EC 3.1.1.7 (acetylcholinesterase) inhibitor		1969197452.5low020000
oxidopamine
2
benzenetriol;
catecholamine;
primary amino compound		drug metabolite;
human metabolite;
neurotoxin		1981198342.0low020000
oxyphenbutazone
1
phenols;
pyrazolidines		antimicrobial agent;
antineoplastic agent;
antipyretic;
drug metabolite;
gout suppressant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic metabolite		1964196460.0low010000
fenclonine
6
phenylalanine derivative1971198348.5low160000
papaverine
1
benzylisoquinoline alkaloid;
dimethoxybenzene;
isoquinolines		antispasmodic drug;
vasodilator agent		1970197054.0low010000
pargyline
2
aromatic amine1969197154.0low120000
pentobarbital
4
barbituratesGABAA receptor agonist1970198744.5low040000
phenacetin
1
acetamides;
aromatic ether		cyclooxygenase 3 inhibitor;
non-narcotic analgesic;
peripheral nervous system drug		1969196955.0low010000
phenobarbital
2
barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative		1963196958.0low020000
phenoxybenzamine
4
aromatic amine1966197455.0low040000
phenylbutazone
3
pyrazolidinesantirheumatic drug;
EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor;
metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug		1964196958.3low030000
potassium chloride
3
inorganic chloride;
inorganic potassium salt;
potassium salt		fertilizer1971198946.3low030000
proadifen
1
diarylmethane1985198539.0low010000
probenecid
2
benzoic acids;
sulfonamide		uricosuric drug1965196758.0low020000
procaine
3
benzoate ester;
substituted aniline;
tertiary amino compound		central nervous system depressant;
drug allergen;
local anaesthetic;
peripheral nervous system drug		1966197654.7low030000
promethazine
4
phenothiazines;
tertiary amine		anti-allergic agent;
anticoronaviral agent;
antiemetic;
antipruritic drug;
H1-receptor antagonist;
local anaesthetic;
sedative		1965198942.8low040000
propranolol
3
naphthalenes;
propanolamine;
secondary amine		anti-arrhythmia drug;
antihypertensive agent;
anxiolytic drug;
beta-adrenergic antagonist;
environmental contaminant;
human blood serum metabolite;
vasodilator agent;
xenobiotic		1974197549.7low030000
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		1969196955.0low010000
spiperone
2
aromatic ketone;
azaspiro compound;
organofluorine compound;
piperidines;
tertiary amino compound		alpha-adrenergic antagonist;
antipsychotic agent;
dopaminergic antagonist;
psychotropic drug;
serotonergic antagonist		1985198738.0low020000
tolmetin
1
aromatic ketone;
monocarboxylic acid;
pyrroles		EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-steroidal anti-inflammatory drug		1998199826.0low001000
tripelennamine
1
aromatic amine1969196955.0low010000
tyramine
1
monoamine molecular messenger;
primary amino compound;
tyramines		EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter		1976197648.0low010000
xylazine
1
1,3-thiazine;
methylbenzene;
secondary amino compound		alpha-adrenergic agonist;
analgesic;
emetic;
muscle relaxant;
sedative		1984198440.0low010000
corticosterone
3
11beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite		1979198243.7low030000
lysergic acid diethylamide
1
ergoline alkaloid;
monocarboxylic acid amide;
organic heterotetracyclic compound		dopamine agonist;
hallucinogen;
serotonergic agonist		1969196955.0low010000
reserpine
11
alkaloid ester;
methyl ester;
yohimban alkaloid		adrenergic uptake inhibitor;
antihypertensive agent;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
environmental contaminant;
first generation antipsychotic;
plant metabolite;
xenobiotic		1963200453.2low0100100
thymidine
2
pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite		1964197355.5low020000
dextroamphetamine
6
1-phenylpropan-2-amineadrenergic agent;
adrenergic uptake inhibitor;
dopamine uptake inhibitor;
dopaminergic agent;
neurotoxin;
sympathomimetic agent		1971197849.7low060000
carbachol
2
ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic		1979198940.0low020000
metaraminol
1
phenylethanolaminesalpha-adrenergic agonist;
sympathomimetic agent;
vasoconstrictor agent		1966196658.0low010000
pilocarpine
2
pilocarpineantiglaucoma drug1974197549.5low020000
dimethylphenylpiperazinium iodide
1
N-arylpiperazine;
organic iodide salt;
piperazinium salt;
quaternary ammonium salt		nicotinic acetylcholine receptor agonist1974197450.0low010000
serine
2
L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid;
serine zwitterion;
serine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		1976197847.0low020000
chloramphenicol
3
C-nitro compound;
carboxamide;
diol;
organochlorine compound		antibacterial drug;
antimicrobial agent;
Escherichia coli metabolite;
geroprotector;
Mycoplasma genitalium metabolite;
protein synthesis inhibitor		1964197056.3low030000
aspartic acid
8
aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter		1978198937.5low080000
lysine
1
aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite		1969196955.0low010000
cyanides
1
pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor1973197351.0low010000
physostigmine
6
carbamate ester;
indole alkaloid		antidote to curare poisoning;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		1969199049.3low151000
sucrose
4
glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent		1968198246.2low040000
tubocurarine
3
bisbenzylisoquinoline alkaloiddrug allergen;
muscle relaxant;
nicotinic antagonist		1969199246.7low121000
apomorphine
7
aporphine alkaloidalpha-adrenergic drug;
antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
emetic;
serotonergic drug		1967198743.7low070000
aminopyrine
4
pyrazolone;
tertiary amino compound		antipyretic;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic		1964197455.0low040000
uridine
3
uridinesdrug metabolite;
fundamental metabolite;
human metabolite		1969197353.0low030000
galactose
1
D-galactose;
galactopyranose		Escherichia coli metabolite;
mouse metabolite		1978197846.0low010000
phenylephrine
1
phenols;
phenylethanolamines;
secondary amino compound		alpha-adrenergic agonist;
cardiotonic drug;
mydriatic agent;
nasal decongestant;
protective agent;
sympathomimetic agent;
vasoconstrictor agent		1966196658.0low010000
edetic acid
1
ethylenediamine derivative;
polyamino carboxylic acid;
tetracarboxylic acid		anticoagulant;
antidote;
chelator;
copper chelator;
geroprotector		1974197450.0low010000
tyrosine
2
amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical		1969197253.5low020000
methylene blue
1
organic chloride saltacid-base indicator;
antidepressant;
antimalarial;
antimicrobial agent;
antioxidant;
cardioprotective agent;
EC 1.4.3.4 (monoamine oxidase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 4.6.1.2 (guanylate cyclase) inhibitor;
fluorochrome;
histological dye;
neuroprotective agent;
physical tracer		1974197450.0low010000
leucine
7
amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite		1964197454.9low070000
methionine
3
aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical		1964196958.3low030000
phenylalanine
4
amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite		1969197154.0low140000
desoxycorticosterone
1
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
mineralocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite		1969196955.0low010000
colchicine
1
alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen		1975197549.0low010000
cycloheximide
2
antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor		1975197549.0low020000
chloroform
2
chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant		1974197947.5low020000
histidine
2
amino acid zwitterion;
histidine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite		1969197054.5low020000
n-pentanol
5
pentanol;
short-chain primary fatty alcohol		human metabolite;
plant metabolite		1973197450.4low050000
valine
1
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite		1988198836.0low010000
tryptophan
2
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite		1977197946.0low020000
acetonitrile
1
aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent		1999199925.0low001000
phencyclidine
6
benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug		1982198937.7low060000
ethoheptazine
1
azepanes1964196460.0low010000
cyclizine
3
N-alkylpiperazineantiemetic;
central nervous system depressant;
cholinergic antagonist;
H1-receptor antagonist;
local anaesthetic		1968198948.0low230000
brompheniramine
1
organobromine compound;
pyridines		anti-allergic agent;
H1-receptor antagonist		1979197945.0low010000
pseudoephedrine
6
phenylethanolamines;
secondary alcohol;
secondary amino compound		anti-asthmatic drug;
bronchodilator agent;
central nervous system drug;
nasal decongestant;
plant metabolite;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic		1984198938.5low260000
tolonium chloride
1
1974197450.0low010000
diphenyl
1
aromatic fungicide;
benzenes;
biphenyls		antifungal agrochemical;
antimicrobial food preservative		1953195371.0low010000
phenothiazine
1
phenothiazineferroptosis inhibitor;
plant metabolite;
radical scavenger		1964196460.0low010000
1,3-ditolylguanidine
1
toluenes1989198935.0low010000
pyridostigmine bromide
1
pyridinium salt1990199034.0low001000
cyclohexanol
1
cyclohexanols;
secondary alcohol		solvent2004200420.0low000100
anileridine
4
ethyl ester;
piperidinecarboxylate ester;
substituted aniline		opioid analgesic;
opioid receptor agonist		1962199149.5low031000
diphenhydramine hydrochloride
25
hydrochloride;
organoammonium salt		anti-allergic agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
sedative		1966198940.1low5250000
cyclopentane
2
cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent1986198737.5low020000
thiazoles
1
1,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene		2007200717.0low000100
ephedrine
9
phenethylamine alkaloid;
phenylethanolamines		bacterial metabolite;
environmental contaminant;
nasal decongestant;
plant metabolite;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic		1979199938.0low181000
ethamivan
1
methoxybenzenes;
phenols		1991199133.0low001000
hemicholinium 3
2
1973197450.5low020000
methysergide
1
ergoline alkaloid1976197648.0low010000
hydantoins
3
imidazolidine-2,4-dione1988199035.3low121000
dextropropoxyphene
10
1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoatemu-opioid receptor agonist;
opioid analgesic		1964198052.1low0100000
kainic acid
1
dicarboxylic acid;
L-proline derivative;
non-proteinogenic L-alpha-amino acid;
pyrrolidinecarboxylic acid		antinematodal drug;
excitatory amino acid agonist		1987198737.0low010000
phenylpropanolamine
2
amphetamines;
phenethylamine alkaloid		plant metabolite1984198440.0low120000
indophenol
1
quinone iminedye2007200717.0low000100
methadyl acetate
4
diarylmethane1976198046.5low040000
echothiophate iodide
1
iodide salt;
quaternary ammonium salt		antiglaucoma drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
miotic		1992199232.0low001000
podophyllotoxin
1
furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator		1986198638.0low010000
methoxyhydroxyphenylglycol
1
methoxybenzenes;
phenols		1985198539.0low010000
methamphetamine
1
amphetamines;
secondary amine		central nervous system stimulant;
environmental contaminant;
neurotoxin;
psychotropic drug;
xenobiotic		1984198440.0low010000
phenoperidine
4
piperidines1967197454.2low240000
phenazocine
6
1966197454.8low060000
d-alpha tocopherol
1
alpha-tocopherolalgal metabolite;
antiatherogenic agent;
anticoagulant;
antioxidant;
antiviral agent;
EC 2.7.11.13 (protein kinase C) inhibitor;
immunomodulator;
micronutrient;
nutraceutical;
plant metabolite		2007200717.0low000100
pimozide
1
benzimidazoles;
heteroarylpiperidine;
organofluorine compound		antidyskinesia agent;
dopaminergic antagonist;
first generation antipsychotic;
H1-receptor antagonist;
serotonergic antagonist		1974197450.0low010000
benperidol
1
aromatic ketone1971197153.0low010000
glaucine
1
aporphine alkaloid;
organic heterotetracyclic compound;
polyether;
tertiary amino compound		antibacterial agent;
antineoplastic agent;
antitussive;
muscle relaxant;
NF-kappaB inhibitor;
plant metabolite;
platelet aggregation inhibitor;
rat metabolite		1984198440.0low110000
cyclazocine
20
1966198946.1low1200000
n-methylaspartate
8
amino dicarboxylic acid;
D-alpha-amino acid;
D-aspartic acid derivative;
secondary amino compound		neurotransmitter agent1985200933.6low070100
bromine
2
diatomic bromine1975199041.5low011000
ammonium bromide
1
ammonium salt;
bromide salt		NMR chemical shift reference compound1999199925.0low001000
ammonium chloride
1
ammonium salt;
inorganic chloride		ferroptosis inhibitor1999199925.0low001000
etorphine
18
1975200739.5low0142200
fluorides
3
halide anion;
monoatomic fluorine		1973197450.3low030000
clonixin
1
aminopyridine;
organochlorine compound;
pyridinemonocarboxylic acid		antipyretic;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
lipoxygenase inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
platelet aggregation inhibitor;
vasodilator agent		1984198440.0low010000
n-n-propylnorapomorphine
1
1985198539.0low010000
phenyl acetate
2
benzenes;
phenyl acetates		1970199939.5low011000
4-heptanone
1
dialkyl ketonebiomarker;
human urinary metabolite;
human xenobiotic metabolite;
rat metabolite		1953195371.0low010000
4-methoxyamphetamine
1
1970197054.0low010000
glutamic acid
3
glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical		1984198937.3low030000
torpedo
1
1992199232.0low001000
azides
1
pseudohalide anionmitochondrial respiratory-chain inhibitor1973197351.0low010000
adenosine diphosphate ribose
1
ADP-sugarEscherichia coli metabolite;
mouse metabolite		1993199331.0low001000
tramadol
5
2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanoladrenergic 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		1998202217.4low001301
almitrine
1
piperazines;
triamino-1,3,5-triazine		central nervous system stimulant1989198935.0low010000
substance p
2
peptideneurokinin-1 receptor agonist;
neurotransmitter;
vasodilator agent		1980198442.0low020000
flunixin meglumine
1
organoammonium saltantipyretic;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug		1984198440.0low010000
meptazinol
1
azepanes1986198638.0low010000
enkephalin, methionine
8
1981198939.6low080000
colforsin
5
acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist		1993200326.2low003200
alfentanil
1
monocarboxylic acid amide;
piperidines		central nervous system depressant;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic;
peripheral nervous system drug		1987198737.0low010000
fomesafen
3
aromatic ether;
C-nitro compound;
monochlorobenzenes;
N-sulfonylcarboxamide;
organofluorine compound;
phenols		agrochemical;
EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor;
herbicide		1966198249.0low030000
adenosine
1
adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent		1986198638.0low010000
tenocyclidine
1
piperidines;
tertiary amino compound;
thiophenes		central nervous system stimulant;
hallucinogen;
neuroprotective agent;
NMDA receptor antagonist		1989198935.0low010000
venlafaxine hydrochloride
1
hydrochloride2004200420.0low000100
triazoles
1
1,2,3-triazole2007200717.0low000100
bufuralol
1
benzofurans1989198935.0low010000
nicotine
3
3-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic		1967197551.7low030000
homocysteine
1
amino acid zwitterion;
homocysteine;
serine family amino acid		fundamental metabolite;
mouse metabolite		1978197846.0low010000
dextromoramide
10
morpholines;
N-acylpyrrolidine		opioid analgesic1964199952.1low191000
enkephalinamide-met, ala(2)-
5
1981198939.6low050000
enkephalin, d-penicillamine (2,5)-
2
heterodetic cyclic peptidedelta-opioid receptor agonist1994200723.5low001100
u 69593
3
monocarboxylic acid amide;
N-alkylpyrrolidine;
organic heterobicyclic compound;
oxaspiro compound		anti-inflammatory agent;
diuretic;
kappa-opioid receptor agonist		1989200327.7low011100
bremazocine
2
1988198935.5low020000
enkephalin, ser(2), leu(5), thr(6)-
1
oligopeptide1987198737.0low010000
deoxyglucose
1
1975197549.0low010000
quadazocine
2
1987199135.0low011000
tifluadom
1
benzodiazepine1988198836.0low010000
morphiceptin
1
oligopeptide1996199628.0low001000
4-hydroxymephenytoin
1
imidazolidine-2,4-dione1988198836.0low010000
alphaprodine
4
piperidines1965197254.5low040000
deltorphin ii, ala(2)-
1
2007200717.0low000100
mr 2034
1
1988198836.0low010000
ly 274614
1
2003200321.0low000100
ethylketocyclazocine
8
1982198937.2low080000
proline
1
amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite		1969196955.0low010000
norketobemidone
1
1975197549.0medium010000
atropine
11
1963199248.7low0101000
diazodiiodosulfanilic acid
1
1981198143.0medium010000
noscapine
4
aromatic ether;
benzylisoquinoline alkaloid;
cyclic acetal;
isobenzofuranone;
organic heterobicyclic compound;
organic heterotricyclic compound;
tertiary amino compound		antineoplastic agent;
antitussive;
apoptosis inducer;
plant metabolite		1979198938.0low240000
mr 1452
1
1986198638.0low010000
lithium chloride
1
inorganic chloride;
lithium salt		antimanic drug;
geroprotector		1985198539.0low010000
bradykinin
2
oligopeptidehuman blood serum metabolite;
vasodilator agent		1964196460.0low020000
ouabain
1
11alpha-hydroxy steroid;
14beta-hydroxy steroid;
5beta-hydroxy steroid;
alpha-L-rhamnoside;
cardenolide glycoside;
steroid hormone		anti-arrhythmia drug;
cardiotonic drug;
EC 2.3.3.1 [citrate (Si)-synthase] inhibitor;
EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor;
EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
ion transport inhibitor;
plant metabolite		1973197351.0low010000
puromycin
4
puromycinsantiinfective agent;
antimicrobial agent;
antineoplastic agent;
EC 3.4.11.14 (cytosol alanyl aminopeptidase) inhibitor;
EC 3.4.14.2 (dipeptidyl-peptidase II) inhibitor;
nucleoside antibiotic;
protein synthesis inhibitor		1967197553.8low040000
tartaric acid
7
tartaric acidEscherichia coli metabolite1953195968.7low070000
strychnine
1
monoterpenoid indole alkaloid;
organic heteroheptacyclic compound		avicide;
cholinergic antagonist;
glycine receptor antagonist;
neurotransmitter agent;
rodenticide		1981198143.0low010000
pentazocine
29
benzazocine1966200047.3low3272000
n-formylmethionine leucyl-phenylalanine
1
tripeptide1985198539.0low010000
diprenorphine
6
morphinane alkaloid1981200731.7low032100
betadex
1
cyclodextrin2007200717.0low000100
cocaine
10
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		1966197552.0low0100000
dactinomycin
2
actinomycinmutagen1966196757.5low020000
enkephalin, leucine
32
pentapeptide;
peptide zwitterion		analgesic;
delta-opioid receptor agonist;
human metabolite;
mu-opioid receptor agonist;
neurotransmitter;
rat metabolite		1977200638.1low0238100
potassium acetate
1
potassium saltfood acidity regulator1999199925.0low001000
sodium acetate, anhydrous
1
organic sodium saltNMR chemical shift reference compound1999199925.0low001000
ammonium acetate
1
acetate salt;
ammonium salt		buffer;
food acidity regulator		1999199925.0low001000
norlevorphanol
4
1987199035.2medium131000
buprenorphine
10
morphinane alkaloiddelta-opioid receptor antagonist;
kappa-opioid receptor antagonist;
mu-opioid receptor agonist;
opioid analgesic		1988202122.2low015211
arginine vasopressin
1
vasopressincardiovascular drug;
hematologic agent;
mitogen		1963196361.0low010000
chlorprothixene
1
chlorprothixene1969196955.0low010000
benztropine
1
diarylmethane1973197351.0low010000
thiopental
3
barbituratesanticonvulsant;
drug allergen;
environmental contaminant;
intravenous anaesthetic;
sedative;
xenobiotic		1969197951.0low130000
lithium
3
alkali metal atom1973198742.3low030000
dezocine
2
phenols;
primary amino compound		opioid analgesic1999200024.5low002000
quinine
2
cinchona alkaloidantimalarial;
muscle relaxant;
non-narcotic analgesic		1969197253.5low020000
mr 2266
1
1986198638.0low010000
ici 154129
4
1984199136.8low031000
3-methoxy-4-hydroxyphenylglycol sulfate
1
alcohol;
phenols		1985198539.0low010000
u-50488
9
dichlorobenzene;
monocarboxylic acid amide;
N-alkylpyrrolidine		analgesic;
antitussive;
calcium channel blocker;
diuretic;
kappa-opioid receptor agonist		1987201128.1low033210
dimemorfan
2
morphinane alkaloid1984198937.5low020000
ketazocine
1
1982198242.0low010000
alpha-chymotrypsin
1
1974197450.0low010000
naphthoquinones
2
1968196955.5low020000
dinoprostone
1
prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic		1982198242.0low010000
thromboxane a2
1
epoxy monocarboxylic acid;
thromboxanes A		mouse metabolite1996199628.0low001000
codeine
48
morphinane alkaloid;
organic heteropentacyclic compound		antitussive;
drug allergen;
environmental contaminant;
opioid analgesic;
opioid receptor agonist;
prodrug;
xenobiotic		1962200047.4low5453000
phenylephrine hydrochloride
1
hydrochloride1984198440.0low110000
dihydrocodeine
2
morphinane alkaloid1989200029.5low011000
hydrocodone
1
morphinane-like compound;
organic heteropentacyclic compound		antitussive;
mu-opioid receptor agonist;
opioid analgesic		202220222.0low000001
hydromorphone
22
morphinane alkaloid;
organic heteropentacyclic compound		mu-opioid receptor agonist;
opioid analgesic		1963202247.9low1200101
nalorphine
38
morphinane alkaloid1955198653.7low1380000
naloxone
135
morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist		1972200744.0low012110400
oxycodone
3
organic heteropentacyclic compound;
semisynthetic derivative		antitussive;
mu-opioid receptor agonist;
opioid analgesic		1986202225.3low020001
oxymorphone
7
morphinane alkaloid1969198648.1low070000
morphine
214
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		1955202345.5low418420802
alpha-neoendorphin
1
1986198638.0low010000
beta-funaltrexamine
1
morphinane alkaloid1990199034.0low001000
preclamol
4
1989199034.5low022000
lysophosphatidylcholines
1
1-O-acyl-sn-glycero-3-phosphocholine1971197153.0low010000
nalbuphine
4
organic heteropentacyclic compoundmu-opioid receptor antagonist;
opioid analgesic		1991200525.2low003100
thebaine
3
morphinane alkaloid;
organic heteropentacyclic compound		1968197154.7low030000
fluvoxamine
2
(trifluoromethyl)benzenes;
5-methoxyvalerophenone O-(2-aminoethyl)oxime		antidepressant;
anxiolytic drug;
serotonin uptake inhibitor		2004200718.5low000200
rubidium
1
alkali metal atom1989198935.0low010000
levallorphan
37
morphinane alkaloid1954201053.9low0351100
dihydromorphine
4
morphinane alkaloid1981198938.2low040000
naltrexone
21
cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic		1976201136.7low0127110
dextromethorphan
149
6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthreneantitussive;
environmental contaminant;
neurotoxin;
NMDA receptor antagonist;
oneirogen;
prodrug;
xenobiotic		1973202437.5low1612520112
dextrorphan
129
morphinane alkaloid1953202440.1high211112312
butorphanol
4
morphinane alkaloidantitussive;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic		1984200527.0low012100
phosphorus
1
monoatomic phosphorus;
nonmetal atom;
pnictogen		macronutrient1982198242.0low010000
heroin
18
morphinane alkaloidmu-opioid receptor agonist;
opioid analgesic;
prodrug		1966198849.4low0180000
6-o-monoacetylmorphine
1
morphinane alkaloid1984198440.0low010000
normorphine
1
morphinane alkaloid1990199034.0low001000
enkephalin, ala(2)-mephe(4)-gly(5)-
6
1984199731.3low015000
enkephalinamide-leu, ala(2)-
1
1984198440.0low010000
naltrindole
1
isoquinolines2000200024.0low001000
ammonium sulfate
1
ammonium salt;
inorganic sulfate salt		fertilizer1974197450.0low010000
dizocilpine maleate
3
maleate salt;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist		1988199633.3low021000
i(3)so3-galactosylceramide
3
galactosylceramide sulfate;
N-acyl-beta-D-galactosylsphingosine		1974197649.0low030000
morphinans
80
isoquinoline alkaloid fundamental parent;
morphinane alkaloid		1959199245.5low2764000
enkephalin, leucine-2-alanine
6
1984200034.8low042000
ropizine
5
1988199034.8high032000
naloxonazine
1
1996199628.0low001000
tapentadol
2
alkylbenzene202120222.5low000002
pentagastrin
1
organic molecular entity1975197549.0low010000
norcodeine
1
morphinane alkaloid1990199034.0low001000
g(m1) ganglioside
1
alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine;
sialotetraosylceramide		2007200717.0low000100
sepharose
1
1976197648.0low010000
pituitrin
3
1963198151.0low030000
cholecystokinin
1
1984198440.0low010000
dynorphins
5
1985200625.2low011300
beta-endorphin
4
1981199038.5low031000
phosphatidylcholines
2
1,2-diacyl-sn-glycero-3-phosphocholine1971197451.5low020000
bucladesine
2
3',5'-cyclic purine nucleotide1974197549.5low020000
dynorphins
1
1985198539.0low010000
glycolipids
1
1981198143.0low010000
piperidines
8
1970199041.4low162000
methylcellulose
1
1988198836.0low010000
vasoactive intestinal peptide
3
1979199637.7low021000
ascorbic acid
2
ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent		1984200728.5low110100
salicylates
3
monohydroxybenzoateplant metabolite1964196956.7low030000
cyclic gmp
2
3',5'-cyclic purine nucleotide;
guanyl ribonucleotide		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite		1975197947.0low020000
guanosine triphosphate
2
guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor		1989199333.0low011000
guanine
1
2-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite		1966196658.0low010000
guanosine 5'-o-(3-thiotriphosphate)
3
nucleoside triphosphate analogue1997200325.0low002100
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		1970197054.0low010000
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		2007200717.0low000100
guanylyl imidodiphosphate
4
nucleoside triphosphate analogue1987199534.2low031000
trypsinogen
1
1974197450.0low010000
phosphorus radioisotopes
1
1974197450.0low010000
preproenkephalin
1
1986198638.0low010000
phenanthrenes
2
1970197153.5low020000
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Absence Seizure0
8
1973198839.9low080000
Ache0
31
1954202340.5low3186511
Acroosteolysis, Giaccai Type0
1
1989198935.0low010000
Action Tremor0
1
1973197351.0low010000
Acute Disease0
1
1986198638.0low110000
Acute Hypercapnic Respiratory Failure0
3
1954199655.7low021000
Acute Liver Injury, Drug-Induced0
4
1985201629.2low030010
Acute Post-operative Pain0
4
1953198258.0low140000
Addiction, Opioid0
5
1980202033.0low040010
Adenocarcinoma0
1
1982198242.0low010000
Adenocarcinoma, Basal Cell0
1
1982198242.0low010000
Aggression0
1
1988198836.0low010000
Aging0
3
1975200140.0low020100
Akinetic-Rigid Variant of Huntington Disease0
1
1989198935.0low110000
Alcohol Abuse0
3
1982198938.7low030000
Alcohol Drinking0
2
1976197648.0low020000
Alcoholic Cirrhosis0
1
1989198935.0low010000
Alcoholic Intoxication0
1
1976197648.0low010000
Alcoholism0
3
1982198938.7low030000
Allergy, Drug0
2
1975198942.0low120000
Allodynia0
2
1982198739.5low020000
Anankastic Personality0
1
2007200717.0low000100
Anasarca0
1
1990199034.0low001000
Anesthesia0
9
1954198465.0low090000
Anochlesia0
1
1984198440.0low010000
Anoxemia0
3
1970198743.3low130000
Anterior Choroidal Artery Infarction0
1
1988198836.0low010000
Anterior Circulation Transient Ischemic Attack0
3
1988198935.3low030000
Antibody Deficiency Syndrome0
1
1979197945.0low010000
Arthritis, Degenerative0
1
1964196460.0low010000
Asphyxia0
1
1970197054.0low010000
Asymmetric Diabetic Proximal Motor Neuropathy0
1
1998199826.0low001000
Aura0
1
1989198935.0low010000
Autoimmune Disease0
1
1990199034.0low001000
Autoimmune Diseases0
1
1990199034.0low001000
Benign Neoplasms0
7
1964202329.3low231201
Benign Neoplasms, Brain0
1
1997199727.0low001000
Benign Psychomotor Epilepsy, Childhood0
1
1990199034.0low001000
Bilateral Headache0
1
1984198440.0low110000
Bilirubinemia0
1
2000200024.0low001000
Birth Weight0
1
1977197747.0low010000
Blepharoptosis0
1
2004200420.0low000100
Blood Pressure, Low0
1
1969196955.0low110000
Body Weight0
4
1968198446.2low040000
Brain Diseases0
1
1990199034.0low001000
Brain Disorders0
1
1990199034.0low001000
Brain Ischemia0
5
1982198837.4low050000
Brain Neoplasms0
1
1997199727.0low001000
Brain Vascular Disorders0
1
1982198242.0low010000
Breast Cancer0
1
201820186.0low000010
Breast Neoplasms0
1
201820186.0low000010
Breathlessness0
1
1986198638.0low110000
Bronchitis0
1
1984198440.0low110000
Cancer of Lung0
1
1990199034.0low001000
Cancer Pain0
1
201820186.0low000010
Cancer-Associated Pain0
1
201820186.0low000010
Carcinoma, Ehrlich Tumor0
1
1984198440.0low010000
Cardiac Death0
1
1970197054.0low010000
Cataract0
3
1966197055.3low030000
Cataract, Membranous0
3
1966197055.3low030000
Catarrh0
2
1984198440.0low220000
Catatonic Rigidity0
1
1984198440.0low010000
Central Nervous System Disease0
1
2003200321.0low100100
Central Nervous System Diseases0
1
2003200321.0low100100
Cerebral Infarction0
1
1988198836.0low010000
Cerebral Ischemia0
5
1982198837.4low050000
Cerebrovascular Disorders0
1
1982198242.0low010000
Chemical and Drug Induced Liver Injury0
4
1985201629.2low030010
Chemical Dependence0
18
1967199245.9low0162000
Chronic Disease0
7
1981200925.7low120500
Chronic Illness0
7
1981200925.7low120500
Chronic Motor and Vocal Tic Disorder0
1
2007200717.0low000100
Chronic Pain0
1
202020204.0low000010
Cocaine Abuse0
1
2001200123.0low000100
Cocaine-Related Disorders0
1
2001200123.0low000100
Colitis Gravis0
1
1967196757.0low010000
Colitis, Ulcerative0
1
1967196757.0low010000
Colonic Inertia0
2
1982199834.0low011000
Common Cold0
2
1984198440.0low220000
Complication, Postoperative0
5
1969198149.8low250000
Constipation0
2
1982199834.0low011000
Corneal Opacity0
1
1971197153.0low010000
Cough0
11
1978198939.7low6110000
Cranial Nerve Diseases0
1
1992199232.0low001000
Day Blindness0
1
1984198440.0low110000
Decerebrate Posturing0
1
1986198638.0low010000
Dehydration0
1
1970197054.0low010000
Delayed Effects, Prenatal Exposure0
1
1983198341.0low010000
Dermatitis Medicamentosa0
1
1990199034.0low001000
Diabetic Neuropathies0
1
1998199826.0low001000
Diathesis0
1
1990199034.0low001000
Disease Models, Animal0
4
1981200730.5low021100
Diseases, Metabolic0
1
1989198935.0low010000
Drug Hypersensitivity0
2
1975198942.0low120000
Drug Withdrawal Symptoms0
20
1964201143.7low2162110
Dyskinesia Syndromes0
1
1988198836.0low010000
Dyspnea0
1
1986198638.0low110000
Edema0
1
1990199034.0low001000
Electrolytes0
2
1981199934.0low011000
Emesis0
3
1968197055.0low230000
Epilepsy0
1
1989198935.0low010000
Epilepsy, Temporal Lobe0
1
1990199034.0low001000
Experimental Neoplasms0
2
1981198441.5low020000
Extravascular Hemolysis0
1
1969196955.0low010000
Eye Diseases0
2
1966196658.0low020000
Eye Disorders0
2
1966196658.0low020000
Fever0
1
1972197252.0low010000
Fistula0
1
1975197549.0low010000
Glial Cell Tumors0
2
1975198544.0low020000
Glioma0
2
1975198544.0low020000
Habit Chorea0
1
2007200717.0low000100
Headache0
1
1984198440.0low110000
Hemiplegia0
1
1982198242.0low010000
Hemiplegia, Crossed0
1
1982198242.0low010000
Hemolysis0
1
1969196955.0low010000
Hepatitis0
1
1990199034.0low001000
Hereditary Sensory and Autonomic Neuropathies0
1
1989198935.0low010000
Heroin Abuse0
2
1976199041.0low111000
Heroin Dependence0
2
1976199041.0low111000
Huntington Disease0
1
1989198935.0low110000
Hyperesthesia0
2
1982198739.5low020000
Hyperglycemia0
1
1955195569.0low010000
Hyperglycemia, Postprandial0
1
1955195569.0low010000
Hypotension0
1
1969196955.0low110000
Hypoxia0
3
1970198743.3low130000
Immunologic Deficiency Syndromes0
1
1979197945.0low010000
Infection0
1
1979197945.0low010000
Infection, Postoperative Wound0
1
1979197945.0low010000
Infections0
1
1979197945.0low010000
Inflammation0
1
1987198737.0low010000
Innate Inflammatory Response0
1
1987198737.0low010000
Intradural-Extramedullary Spinal Cord Neoplasms0
1
1982198242.0low010000
Ischemia0
1
1989198935.0low010000
Ischemic Attack, Transient0
3
1988198935.3low030000
Leukoma0
1
1971197153.0low010000
Liver Cirrhosis, Alcoholic0
1
1989198935.0low010000
Liver Diseases0
1
1989198935.0low010000
Liver Dysfunction0
1
1989198935.0low010000
Long Sleeper Syndrome0
1
1984198440.0low110000
Lung Diseases, Obstructive0
1
1985198539.0low110000
Lung Neoplasms0
1
1990199034.0low001000
Metabolic Diseases0
1
1989198935.0low010000
Morphine Abuse0
15
1968199847.1low1141000
Morphine Dependence0
15
1968199847.1low1141000
Movement Disorders0
1
1988198836.0low010000
Muscle Contraction0
14
1972201342.1low0112010
Muscle Rigidity0
1
1984198440.0low010000
Muscle Spasm0
2
1970197054.0low020000
Nausea0
2
1968196955.5low220000
Necrosis0
1
1989198935.0low010000
Neoplasms0
7
1964202329.3low231201
Nerve Pain0
5
1992202116.6low101211
Nervous System Diseases0
1
2003200321.0low000100
Nervous System Disorders0
1
2003200321.0low000100
Neuralgia0
5
1992202116.6low101211
Neuroblastoma0
9
1973199738.8low054000
Obsessive-Compulsive Disorder0
1
2007200717.0low000100
Obstructive Lung Diseases0
1
1985198539.0low110000
Odontalgia0
1
1965196559.0low010000
Opioid-Related Disorders0
5
1980202033.0low040010
Osteoarthritis0
1
1964196460.0low010000
Osteogenic Sarcoma0
1
201820186.0low000010
Osteosarcoma0
1
201820186.0low000010
Pain1
31
1954202340.5low3186511
Pain, Chronic0
1
202020204.0low000010
Pain, Intractable0
5
1982201828.2low030110
Pain, Postoperative0
4
1953198258.0low140000
Peripheral Nerve Diseases0
1
2003200321.0low100100
Peripheral Nervous System Diseases0
1
2003200321.0low100100
Poisoning0
2
1969197751.0low020000
Polydipsia0
1
1958195866.0low010000
Polyuria0
1
1958195866.0low010000
Postoperative Complications0
5
1969198149.8low250000
Pregnancy0
3
1976198345.3low030000
Ptosis, Eyelid0
1
2004200420.0low000100
Pyrexia0
1
1972197252.0low010000
Respiratory Insufficiency0
3
1954199655.7low021000
Retinal Diseases0
1
1989198935.0low010000
Sarcoma 1800
1
1984198440.0low010000
Seizures0
8
1973198839.9low080000
Sensitivity and Specificity0
2
1999200024.5low002000
Sleep Wake Disorders0
1
1984198440.0low110000
Spasm0
2
1970197054.0low020000
Spinal Cord Neoplasms0
1
1982198242.0low010000
Spinal Neoplasms0
1
201820186.0low000010
Substance Withdrawal Syndrome0
20
1964201143.7low2162110
Substance-Related Disorders0
18
1967199245.9low0162000
Suffocation0
1
1970197054.0low010000
Tachyarrhythmia0
1
1969196955.0low110000
Tachycardia0
1
1969196955.0low110000
Tics0
1
2007200717.0low000100
Toothache0
1
1965196559.0low010000
Tourette Syndrome0
1
2007200717.0low000100
Tremor0
1
1973197351.0low010000
Urination Disorders0
1
1958195866.0low010000
Visceral Pain0
2
1964196460.0low020000
Vomiting0
3
1968197055.0low230000

Safety/Toxicity (4)

ArticleYear
Levorphanol versus methadone use: safety considerations.
Annals of palliative medicine, , Volume: 9, Issue:2		2020
Dextrorphan and levorphanol selectively block N-methyl-D-aspartate receptor-mediated neurotoxicity on cortical neurons.
The Journal of pharmacology and experimental therapeutics, , Volume: 242, Issue:2		1987
Dextrorphan and dextromethorphan attenuate glutamate neurotoxicity.
Brain research, , Feb-17, Volume: 403, Issue:2		1987
Genetically determined oxidation polymorphism and drug hepatotoxicity. Study of 51 patients.
Journal of hepatology, , Volume: 8, Issue:2		1989

Long-term Use (6)

ArticleYear
Differential agonist regulation of the human kappa-opioid receptor.
Journal of neurochemistry, , Volume: 68, Issue:5		1997
Opiates and thermoregulation in mice. IV. Tolerance and cross-tolerance.
The Journal of pharmacology and experimental therapeutics, , Volume: 223, Issue:3		1982
Dextromethorphan pretreatment induces antipyrine clearance in the rat.
Pharmaceutical research, , Volume: 5, Issue:7		1988
Chronic use of opioid analgesics in non-malignant pain: report of 38 cases.
Pain, , Volume: 25, Issue:2		1986
Opioid receptor subtype-specific cross-tolerance to the effects of morphine on schedule-controlled behavior in mice.
Psychopharmacology, , Volume: 96, Issue:2		1988
The role of opiate receptors in the potentiation of pentobarbital sleeping time by the acute and chronic administration of opiates.
Neuropharmacology, , Volume: 26, Issue:11		1987

Pharmacokinetics (5)

ArticleYear
Levorphanol: pharmacokinetics and steady-state plasma concentrations in patients with pain.
Research communications in chemical pathology and pharmacology, , Volume: 41, Issue:1		1983
Pharmacokinetics of dextromethorphan and dextrorphan: a single dose comparison of three preparations in human volunteers.
International journal of clinical pharmacology, therapy, and toxicology, , Volume: 25, Issue:9		1987
Dextromethorphan pretreatment induces antipyrine clearance in the rat.
Pharmaceutical research, , Volume: 5, Issue:7		1988
Pharmacokinetic comparison of a dextromethorphan-salbutamol combination tablet and a plain dextromethorphan tablet.
International journal of clinical pharmacology, therapy, and toxicology, , Volume: 28, Issue:6		1990
Dextromethorphan: radioimmunoassay and pharmacokinetics in the dog.
Research communications in chemical pathology and pharmacology, , Volume: 22, Issue:2		1978

Bioavailability (5)

ArticleYear
Dextromethorphan and codeine: comparison of plasma kinetics and antitussive effects.
European journal of respiratory diseases, , Volume: 65, Issue:4		1984
Bioavailability evaluation of a controlled-release dextromethorphan liquid.
Journal of clinical pharmacology, , Volume: 27, Issue:2		1987
Sublingual absorption of selected opioid analgesics.
Clinical pharmacology and therapeutics, , Volume: 44, Issue:3		1988
Pharmacokinetic comparison of a dextromethorphan-salbutamol combination tablet and a plain dextromethorphan tablet.
International journal of clinical pharmacology, therapy, and toxicology, , Volume: 28, Issue:6		1990
Determination of dextrorphan in plasma and evaluation of bioavailability of dextromethorphan hydrobromide in humans.
Journal of pharmaceutical sciences, , Volume: 66, Issue:7		1977

Dosage (20)

ArticleYear
Development of an enantioselective high-performance liquid chromatography-tandem mass spectrometry method for the quantitative determination of methorphan and its O-demethylated metabolite in human blood and its application to post-mortem samples.
Journal of pharmaceutical and biomedical analysis, , Jun-15, Volume: 230		2023
Evolution of Analgesic Tolerance and Opioid-Induced Hyperalgesia Over 6 Months: Double-Blind Randomized Trial Incorporating Experimental Pain Models.
The journal of pain, , Volume: 21, Issue:9-10
Buprenorphine and opioid antagonism, tolerance, and naltrexone-precipitated withdrawal.
The Journal of pharmacology and experimental therapeutics, , Volume: 336, Issue:2		2011
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
Pharmacological characterization of opiate physical dependence in the isolated ileum of the guinea-pig.
British journal of pharmacology, , Volume: 73, Issue:4		1981
A double-blind controlled evaluation of the nasal decongestant effect of Day Nurse in the common cold.
The Journal of international medical research, , Volume: 12, Issue:2		1984
Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine.
Progress in neuro-psychopharmacology & biological psychiatry, , Volume: 8, Issue:4-6		1984
Dextromethorphan and codeine: comparison of plasma kinetics and antitussive effects.
European journal of respiratory diseases, , Volume: 65, Issue:4		1984
Quantitation of acetaminophen, chlorpheniramine maleate, dextromethorphan hydrobromide, and phenylpropanolamine hydrochloride in combination using high-performance liquid chromatography.
Journal of pharmaceutical sciences, , Volume: 73, Issue:11		1984
In vivo studies with ICI 154,129, a putative delta receptor antagonist.
Life sciences, , Volume: 31, Issue:20-21
Levorphanol: pharmacokinetics and steady-state plasma concentrations in patients with pain.
Research communications in chemical pathology and pharmacology, , Volume: 41, Issue:1		1983
Histamine release from isolated rat mast cells induced by opiates: effect of sterical configuration and calcium.
Agents and actions, , Volume: 12, Issue:4		1982
Bioavailability evaluation of a controlled-release dextromethorphan liquid.
Journal of clinical pharmacology, , Volume: 27, Issue:2		1987
Selective breeding for levorphanol-induced antinociception on the hot-plate assay: commonalities in mechanism of action with morphine, pentazocine, ethylketocyclazocine, U-50488H and clonidine in mice.
The Journal of pharmacology and experimental therapeutics, , Volume: 241, Issue:2		1987
Potentiation of disruptive effects of dextromethorphan by naloxone on fixed-interval performance in rats.
Psychopharmacology, , Volume: 90, Issue:3		1986
Dextrorphan: an antagonist for phencyclidine receptors.
Life sciences, , Jun-15, Volume: 40, Issue:24		1987
I.v. infusion of opioids for cancer pain: clinical review and guidelines for use.
Cancer treatment reports, , Volume: 70, Issue:5		1986
Discriminative stimulus effects of cyclorphan: selective antagonism with naltrexone.
Psychopharmacology, , Volume: 106, Issue:2		1992
Prenatal administration of morphine to the rat: tolerance to the analgesic effect of morphine in the offspring.
The Journal of pharmacology and experimental therapeutics, , Volume: 197, Issue:3		1976
Changes in plasma corticosterone levels as a measure of acute dependence upon levorphanol in rats.
The Journal of pharmacology and experimental therapeutics, , Volume: 211, Issue:2		1979

Interactions (1)

ArticleYear
[In vitro tests of hepatic oxidation in man, predictive of drug interactions].
Schweizerische medizinische Wochenschrift, , Dec-05, Volume: 117, Issue:49		1987