clopidogrel   Click here for help

GtoPdb Ligand ID: 7150

Synonyms: Iscover® | Plavix® | SR-25990C
Approved drug PDB Ligand
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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View more information in the IUPHAR Pharmacology Education Project: clopidogrel

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1997), EMA (1998))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Is prodrug? Yes
Active form clopidogrel (active metabolite)
IUPAC Name Click here for help
methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
International Nonproprietary Names Click here for help
INN number INN
5908 clopidogrel
Synonyms Click here for help
Iscover® | Plavix® | SR-25990C
Database Links Click here for help
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
Search Google for chemical match using the InChIKey GKTWGGQPFAXNFI-HNNXBMFYSA-N
Search Google for chemicals with the same backbone GKTWGGQPFAXNFI
Search PubMed clinical trials clopidogrel
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UniChem Compound Search for chemical match using the InChIKey GKTWGGQPFAXNFI-HNNXBMFYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GKTWGGQPFAXNFI-HNNXBMFYSA-N
Wikipedia clopidogrel