2396. Clopidogrel

Nomenclature

CAS number: 113665-84-2
(αS)-α-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid methyl ester; methyl (+)-(S)-α-(o-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetate; (+)-methyl-α-5-[4,5,6,7-tetrahydro[3,2-c]thienopyridyl]-(2-chlorophenyl)acetate; SR-25990.
C16H16ClNO2S; mol wt 321.82.
C 59.71%, H 5.01%, Cl 11.02%, N 4.35%, O 9.94%, S 9.96%.

Description and 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).

Chemical structure

Properties

Colorless oil. [α]D20 +51.52° (c = 1.61 in methanol).

Derivative

Hydrogen sulfate.

Nomenclature

CAS number: 135046-48-9
SR-25990C; Plavix (Sanofi).
C16H16ClNO2S.H2SO4; mol wt 419.90.
C 45.77%, H 4.32%, Cl 8.44%, N 3.34%, O 22.86%, S 15.27%.

Properties

White crystals, mp 184°. [α]D20 +55.10° (c = 1.891 in methanol). Sol in water, methanol.

Therapeutic Category

Antithrombotic.

Keywords

Antithrombotic