5543-57-7

(–)-Warfarin is a component of (±)-warfarin (Item No. 13566). It is an anticoagulant that interferes with interconversion of vitamin K and vitamin K epoxide and the role of vitamin K in carboxylation of several clotting cascade proteins, inhibiting the initiation of clotting. In vivo, (–)-warfarin slows formation of the prothrombin complex and exhibits 6.6-fold more potent anticoagulant activity than (+)-warfarin (Item No. 13526) in rats. (–)-Warfarin is primarily metabolized by the cytochrome P450 (CYP) isoform CYP2C9 and genetic polymorphisms in this enyzme, as well as other compounds metabolized by CYP2C9, increase the potential for catastrophic bleeding complications. Formulations containing warfarin have been used to treat and prevent blood clots in atrial fibrillation, heart valve replacement, venous thrombosis, and pulmonary embolism.

White Solid

The S-(-)-form of Warfarin (W498500). Coumarin anticoagulant.

ChEBI: (S)-warfarin is a 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one that has (S)-configuration (the racemate is warfarin, an anticoagulant drug and rodenticide). It is a conjugate acid of a (S)-warfarin(1-). It is an enantiomer of a (R)-warfarin.

Warfarin is used to regulate and inhibit thromboembolic disorders. The CYP2C9 (cytochrome P450 family 2 subfamily C member 9)?protein plays a major role in the inactivation of potent S-warfarin.

[1] A. BRECKENRIDGE  M. L O. The plasma half lives and the pharmacological effect of the enantiomers of warfarin in rats[J]. Life sciences, 1972, 11 7: Pages 337-345. DOI: 10.1016/0024-3205(72)90073-2
[2] AYAKA SHIOZAWA . Effects of acid and lactone forms of statins on S-warfarin 7-hydroxylation catalyzed by human liver microsomes and recombinant CYP2C9 variants (CYP2C9.1 and CYP2C9.3)[J]. Drug Metabolism and Pharmacokinetics, 2021, 36: Article 100364. DOI: 10.1016/j.dmpk.2020.10.003