Shorter-lived enantiomer of the anticoagulant acenocoumarol
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(S)-Acenocoumarol

Item No. 9000336

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2)(1:3): 0.25 mg/mlDMSO: 10 mg/mlEthanol: 0.2 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    Product Description

    (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).1 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.1 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ufer, M. Comparative pharmacokinetics of vitamin K antagonists warfarin, phenprocoumon and acenocoumarol. Clin. Pharmacokinet. 44(12), 1227-1246 (2005).