(R)-Acenocoumarol

• CAT Number: R010224
• CAS Number: 66556-77-2
• Molecular Formula: C19H15NO6
• Molecular Weight: 353.33
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one
• InChI: InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3/t15-/m1/s1
• InChIKey: VABCILAOYCMVPS-OAHLLOKOSA-N
• SMILES: CC(=O)CC(C1=CC=C(C=C1)[N+](=O)[O-])C2=C(C3=CC=CC=C3OC2=O)O

Acenocoumarol is a short-<wbr></wbr>lived oral anti-<wbr></wbr>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. (R)-Acenocoumarol has a longer plasma elimination half-life (6.6 hours) and slower plasma clearance (1.9 L/hour), compared to the (S)-enantiomer (1.8 hours, 28.5 L/hour). The R-enantiomer is rapidly absorbed from the gastrointestinal tract with essentially complete oral bioavailability, whereas (S)-acenocoumarol undergoes extensive first-pass metabolism. Perhaps related to these pharmacokinetic characteristics, (R)-acenocoumarol is more potent in vivo as an anti-coagulant than the (S)-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.