(s)warfarin

(S)-Warfarin is a more effective enantiomer of Warfarin. It is used as a vitamin K antagonist, with anticoagulant.

(S)-Warfarin-d5 is a deuterated compound of (S)-Warfarin.

Acenocoumarol is a short-lived oral anti-coagulant, which, like warfarin, functions by inhibiting vitamin K epoxide reductase. It has higher intrinsic anticoagulant potency than warfarin and phenprocoumon, when evaluated in vitro. Acenocoumarol has a single chiral center that gives rise to two different enantiomeric forms. (S)-Acenocoumarol has a shorter plasma elimination half-life (1.8 hours) and faster plasma clearance (28.5 L/hour), compared to the (R)-enantiomer (6.6 hours, 1.9 L/hour). The S-enantiomer undergoes extensive first-pass metabolism during absorption from the gastrointestinal tract, whereas (R)-acenocoumarol is rapidly absorbed and provides essentially complete oral bioavailability. Perhaps related to these pharmacokinetic characteristics, (S)-acenocoumarol is less potent in vivo as an anti-coagulant than the (R)-enantiomer. As the clearance of acenocoumarol is ~20-fold faster than that for warfarin, the plasma concentrations of acenocoumarol are substantially lower than those for warfarin in patients receiving long-term treatment.

10-hydroxy Warfarin is a metabolite of (R)-warfarin .1It is formed from (R)-warfarin by the cytochrome P450 (CYP) isoform CYP3A4. 10-hydroxy Warfarin is an inhibitor of CYP2C9 (IC50= 1.6 μM), the enzyme that converts (S)-warfarin to its 6-hydroxy warfarin and 7-hydroxy warfarin metabolites.2 1.Kaminsky, L.S., and Zhang, Z.-Y.Human P450 metabolism of warfarinPharmacol. Ther.73(1)67-74(1997) 2.Jones, D.R., Kim, S.-Y., Guderyon, M., et al.Hydroxywarfarin metabolites potently inhibit CYP2C9 metabolism of S-warfarinChem. Res. Toxicol.23(5)939-945(2010)