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
No information available.
Summary of Clinical Use
Clopidogrel is used for its anti-clotting action in patients with conditions such as acute coronary syndrome, myocardial infarction, peripheral vascular diseases and stroke.
Mechanism Of Action and Pharmacodynamic Effects
Clopidogrel prevents adenosine diphosphate (ADP) from binding to platelet membrane P2Y12 receptors (P2RY12). This receptor plays a role in platelet aggregation and thrombus formation [1], thus its inhibition reduces the risk of thrombus formation.
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