Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0355)
Drug Name
Clopidogrel bisulfate
Synonyms
Clopidogrel (Plavix); Clopidogrel (hydrogen sulfate); Clopidogrel Bisulfate [USAN]; Clopidogrel bisulphate; Clopidogrel hemisulfate; Clopidogrel hydrogen sulfate; Clopidogrel sulphate; Iscover; MFCD05865229; Myogrel; PM-103; SR 25990C; UNII-08I79HTP27; Clopidogrel hydrogen sulphate; Clopidogrel; Clopidogrel (TN); Clopidogrel Acino; Clopidogrel BMS; Clopidogrel Hexal; Clopidogrel [INN:BAN]; Clopidogrelum; GKTWGGQPFAXNFI-HNNXBMFYSA-N; HSDB 7430; Plavix (TN); Thrombo; UNII-A74586SNO7; Zyllt; clopidogrel; methyl (2S)-(2-chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)ethanoate; (+)-(S)-Clopidogrel; (+)-Clopidogrel; (S)-Clopidogrel; 113665-84-2; A74586SNO7; CHEBI:37941; CPD000550475; (S)-(+)-Clopidogrel Sulfate; (S)-methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate; 08I79HTP27; 120202-66-6; 135046-48-9
Indication Acute coronary syndrome [ICD11: BA4Z] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 419.9 Topological Polar Surface Area 141
Heavy Atom Count 26 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
115366
ChEBI ID
CHEBI:3759
CAS Number
120202-66-6
TTD Drug ID
D0N0TZ
Formula
C16H18ClNO6S2
Canonical SMILES
COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O
InChI
1S/C16H16ClNO2S.H2O4S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;1-5(2,3)4/h2-5,7,9,15H,6,8,10H2,1H3;(H2,1,2,3,4)/t15-;/m0./s1
InChIKey
FDEODCTUSIWGLK-RSAXXLAASA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-Oxoclopidogrel DM006123
56848893
Oxidation - Oxidationn 1 [2]
Clopidogrel carboxylic acid derivative DM006125
9861403
Unclear 1 [2]
Active Metabolite of Clopidogrel DM006124
165361851
spontaneous - spontaneous 2 [2]
Clopidogrel acyl glucuronide DM006126
96359892
Conjugation - Glucuronidation 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006591 Clopidogrel bisulfate 2-Oxoclopidogrel Oxidation - Oxidationn CYP2C19 ... [2]
MR006593 Clopidogrel bisulfate Clopidogrel carboxylic acid derivative Unclear CES1 ... [2]
MR006592 2-Oxoclopidogrel Active Metabolite of Clopidogrel spontaneous - spontaneous CYP2B6 ... [2]
MR006594 Clopidogrel carboxylic acid derivative Clopidogrel acyl glucuronide Conjugation - Glucuronidation UGT2B7 [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Carboxylesterase 2 (CES2) DME0057 Homo sapiens
EST2_HUMAN
3.1.1.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[7]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [8]
⏷ Show the Full List of 26  DME(s)
References
1 Clopidogrel Bisulfate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
3 Clinical pharmacokinetics and pharmacodynamics of clopidogrel. Clin Pharmacokinet. 2015 Feb;54(2):147-66.
4 Clopidogrel pathway. Pharmacogenet Genomics. 2010 Jul;20(7):463-5.
5 Cytochrome P450 3A inhibition by ketoconazole affects prasugrel and clopidogrel pharmacokinetics and pharmacodynamics differently. Clin Pharmacol Ther. 2007 May;81(5):735-41.
6 Impact of the CYP2C19 gene polymorphism on clopidogrel personalized drug regimen and the clinical outcomes. Clin Lab. 2016 Sep 1;62(9):1773-1780.
7 Physiologically Based Pharmacokinetic (PBPK) Modeling of Clopidogrel and Its Four Relevant Metabolites for CYP2B6, CYP2C8, CYP2C19, and CYP3A4 Drug-Drug-Gene Interaction Predictions
8 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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