| Identification | Back Directory | [Name]
(S)-(-)-Nicoumalone | [CAS]
66556-78-3 | [Synonyms]
(S)-(-)-Nicoumalone
Acenocoumarol Impurity 2（Acenocoumarol (S)-Isomer)
2H-1-Benzopyran-2-one, 4-hydroxy-3-[(1S)-1-(4-nitrophenyl)-3-oxobutyl]- | [Molecular Formula]
C19H15NO6 | [MDL Number]
MFCD00869569 | [MOL File]
66556-78-3.mol | [Molecular Weight]
353.328 |
| Chemical Properties | Back Directory | [Boiling point ]
592.7±50.0 °C(Predicted) | [density ]
1.427±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [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 | [form ]
A crystalline solid | [pka]
4.50±1.00(Predicted) |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
N/A | [Uses]
S-Enantiomer of | [Definition]
ChEBI: The (R)-enantiomer of acenocoumarol. | [storage]
Store at -20°C |
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