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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16ClNO3S
Molecular Weight 337.821
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-OXO-CLOPIDOGREL

SMILES

COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C3=CC=CC=C3Cl

InChI

InChIKey=JBSAZVIMJUOBNB-WUJWULDRSA-N
InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13?,15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H16ClNO3S
Molecular Weight 337.821
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Clopidogrel is first activated to its thiolactone intermediate, 2-oxo-clopidogrel via CYP3A oxidation. 2-oxo-clopidogrel is a key intermediate metabolite from which the active metabolite is formed. 2-oxo-clopidogrel inhibited the activity of CYP2C19 and moderately activity of CYP2B6.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.995 µM [IC50]
1.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Identification of the human cytochrome P450 enzymes involved in the two oxidative steps in the bioactivation of clopidogrel to its pharmacologically active metabolite.
2010 Jan
Cytochromes P450 catalyze both steps of the major pathway of clopidogrel bioactivation, whereas paraoxonase catalyzes the formation of a minor thiol metabolite isomer.
2012 Feb 20
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
2-oxo-clopidogrel (SR121682) is the essential key intermediate metabolite from which the active metabolite is formed. This was approved using enzymatic assay with human liver microsomes. SR121682 was added at a final concentration of 0.1 mM, and the reaction was initiated with 1 mM NADPH
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:14:19 UTC 2023
Edited
by admin
on Sat Dec 16 07:14:19 UTC 2023
Record UNII
0IX303KU54
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-OXO-CLOPIDOGREL
Common Name English
2-OXOCLOPIDOGREL
Common Name English
SR-121683
Code English
(2S)-METHYL 2-(2-CHLOROPHENYL)-2-(2-OXO-7, 7A-DIHYDROTHIENO(3,2-C)PYRIDIN-5(2H,4H,6H)-YL)-ACETATE
Systematic Name English
(7S)-SR121683
Common Name English
(.ALPHA.S)-.ALPHA.-(2,4,5,6,7,7A-HEXAHYDRO-2-OXOTHIENO(3,2-C)PYRIDINE 5-YL)-2-CHLOROBENZENEACETIC ACID METHYL ESTER
Systematic Name English
J3.292.123J
Code English
METHYL (2S)-2-(2-CHLOROPHENYL)-2-(2-OXO-4,6,7,7A-TETRAHYDROTHIENO(3,2-C)PYRIDIN-5-YL)ACETATE
Systematic Name English
CLOPIDOGREL THIOLACTONE
Common Name English
THIENO(3,2-C)PYRIDINE-5(4H)-ACETIC ACID, .ALPHA.-(2-CHLOROPHENYL)-2,6,7,7A-TETRAHYDRO-2-OXO-, METHYL ESTER, (.ALPHA.S)-
Systematic Name English
METHYL (2S)-(2-CHLOROPHENYL)(2-OXO-2,6,7,7A-TETRAHYDROTHIENO(3,2-C)PYRIDIN-5(4H)-YL)ACETATE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID00718734
Created by admin on Sat Dec 16 07:14:19 UTC 2023 , Edited by admin on Sat Dec 16 07:14:19 UTC 2023
PRIMARY
PUBCHEM
56848893
Created by admin on Sat Dec 16 07:14:19 UTC 2023 , Edited by admin on Sat Dec 16 07:14:19 UTC 2023
PRIMARY
FDA UNII
0IX303KU54
Created by admin on Sat Dec 16 07:14:19 UTC 2023 , Edited by admin on Sat Dec 16 07:14:19 UTC 2023
PRIMARY
WIKIPEDIA
Draft:2-Oxo-clopidogrel
Created by admin on Sat Dec 16 07:14:19 UTC 2023 , Edited by admin on Sat Dec 16 07:14:19 UTC 2023
PRIMARY
CAS
1147350-75-1
Created by admin on Sat Dec 16 07:14:19 UTC 2023 , Edited by admin on Sat Dec 16 07:14:19 UTC 2023
PRIMARY
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