2-OXO-CLOPIDOGREL

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19122335

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

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19122335	Inhibitor 8297		0.995 µM [IC50]
Cytochrome P450 2B6 19 Target ID: CHEMBL4729 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19122335	Inhibitor 8297		1.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
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	19812348
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	22103858

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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 GMT 2023` Edited by `admin` on `Sat Dec 16 07:14:19 GMT 2023`
Record UNII	0IX303KU54
Record Status	`Validated (UNII)`
Record Version

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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