Clopidogrel

Title: Clopidogrel
CAS Registry Number: 113665-84-2
CAS Name: (aS)-a-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid methyl ester
Additional Names: methyl (+)-(S)-a-(o-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetate; (+)-methyl-a-5-[4,5,6,7-tetrahydro[3,2-c]thienopyridyl]-(2-chlorophenyl)acetate
Manufacturers' Codes: SR-25990
Molecular Formula: C16H16ClNO2S
Molecular Weight: 321.82
Percent Composition: C 59.71%, H 5.01%, Cl 11.02%, N 4.35%, O 9.94%, S 9.96%
Literature References: Analog of ticlopidine, q.v.; inhibits ADP-induced platelet aggregation. Prepn (unspec. stereochem.): D. Aubert et al., EP 99802; eidem, US 4529596 (1984, 1985 both to Sanofi). Prepn of (+)-form: A. Badorc, D. Fréhel, EP 281459; eidem, US 4847265 (1988, 1989 both to Sanofi). Clinical pharmacology and mechanism of action: D. C. B. Mills et al., Arterioscler. Thromb. 12, 430 (1992). Clinical trial vs aspirin for prevention of atherothrombotic events: CAPRIE Steering Committee, Lancet 348, 1329 (1996). Review of pharmacology and therapeutic potential: G. Feuerstein et al., Expert Opin. Invest. Drugs 4, 425-430 (1995); of use in secondary prevention in stroke: H.-C. Diener et al., Expert Opin. Pharmacother. 6, 755-764 (2005).
Properties: Colorless oil. [a]D20 +51.52° (c = 1.61 in methanol).
Optical Rotation: [a]D20 +51.52° (c = 1.61 in methanol)
Derivative Type: Hydrogen sulfate
CAS Registry Number: 135046-48-9
Manufacturers' Codes: SR-25990C
Trademarks: Plavix (Sanofi)
Molecular Formula: C16H16ClNO2S.H2SO4
Molecular Weight: 419.90
Percent Composition: C 45.77%, H 4.32%, Cl 8.44%, N 3.34%, O 22.86%, S 15.27%
Properties: White crystals, mp 184°. [a]D20 +55.10° (c = 1.891 in methanol). Sol in water, methanol.
Melting point: mp 184°
Optical Rotation: [a]D20 +55.10° (c = 1.891 in methanol)
Therap-Cat: Antithrombotic.
Keywords: Antithrombotic.
Clopidol Clopirac Cloprednol Cloprostenol Clopyralid

Clopidogrel
S-Clopidogrel structure.svg
Clopidogrel 3D.png
Systematic (IUPAC) name
(+)-(S)-methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate
Clinical data
Trade names Plavix
AHFS/Drugs.com monograph
MedlinePlus a601040
Licence data US FDA:link
Pregnancy cat. B1 (AU) B (US)
Legal status Prescription Only (S4) (AU) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability >50%
Protein binding 94–98%
Metabolism Hepatic
Half-life 7–8 hours (inactive metabolite)
Excretion 50% renal
46% biliary
Identifiers
CAS number 113665-84-2 YesY
ATC code B01AC04
PubChem CID 60606
DrugBank DB00758
ChemSpider 54632 YesY
UNII A74586SNO7 YesY
KEGG D07729 YesY
ChEBI CHEBI:37941 YesY
ChEMBL CHEMBL1771 YesY
Chemical data
Formula C16H16ClNO2S 
Mol. mass 321.82 g/mol
 YesY (what is this?)  (verify)

Clopidogrel (INN) is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease. It is marketed by Bristol-Myers Squibb and Sanofi under the trade name Plavix. The drug works by irreversibly inhibiting a receptor called P2Y12, an adenosine diphosphate (ADP) chemoreceptor on platelet cell membranes. Adverse effects include hemorrhage, severe neutropenia, and thrombotic thrombocytopenic purpura (TTP).