(S)-Acenocoumarol

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.Formal Name: 4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one. CAS Number: 66556-78-3. Synonyms: (S)-Acenocoumarin, (S)-Nicoumalone. Molecular Formula: C19H15NO6. Formula Weight: 353.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMF:PBS (pH 7.2)(1:3): 0.25 mg/ml, DMSO: 10 mg/ml, Ethanol: 0.2 mg/ml. lambdamax: 291 nm. SMILES: O=C1C([C@](CC(C)=O)([H])C2=CC=C([N+]([O-])=O)C=C2)=C(O)C3=CC=CC=C3O1. InChi Code: 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-/m0/s1. InChi Key: VABCILAOYCMVPS-HNNXBMFYSA-N.