clopidogrel   

GtoPdb Ligand ID: 7150

Synonyms: Iscover® | Plavix® | SR-25990C
clopidogrel is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: Clopidogrel is a prodrug converted by liver CYP450 via 2-oxo-clopidogrel to an active metabolite, listed in GtoPdb as clopidogrel (active metabolite) [2]. Marketed formulations may contain clopidogrel bisulfate (PubChem CID 115366).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 57.78
Molecular weight 321.06
XLogP 2.73
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C(c1ccccc1Cl)N1CCc2c(C1)ccs2
Isomeric SMILES COC(=O)[C@H](c1ccccc1Cl)N1CCc2c(C1)ccs2
InChI InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
InChI Key GKTWGGQPFAXNFI-HNNXBMFYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1997), EMA (1998))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Is prodrug? Yes
Active form clopidogrel (active metabolite)
IUPAC Name
methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
International Nonproprietary Names
INN number INN
5908 clopidogrel
Synonyms
Iscover® | Plavix® | SR-25990C
Database Links
CAS Registry No. 113665-84-2
ChEBI CHEBI:37941
ChEMBL Ligand CHEMBL1771
DrugBank Ligand DB00758
DrugCentral Ligand 708
GtoPdb PubChem SID 178103725
PubChem CID 60606
RCSB PDB Ligand CGE
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Wikipedia clopidogrel