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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

(R)-(+)-Acenocoumarol

Cayman Chemical Item Number 9000336

(R)-(+)-Nicoumalone; (R)-(+)-Acenocoumarin (CAS 66556-77-2)

(R)-(+)-Acenocoumarol (CAS 66556-77-2)

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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. (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).1 The R-enantiomer is rapidly absorbed from the gastrointestinal tract with essentially complete oral bioavailability, whereas (S)-(−)-acenocoumarol undergoes extensive first-pass metabolism.1 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.

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

Synonyms
  • (R)-(+)-Nicoumalone
  • (R)-(+)-Acenocoumarin
Formal Name 4-​hydroxy-​3-​[1-​(4-​nitrophenyl)-​3-​oxobutyl]-​2H-​1-​benzopyran-​2-​one
CAS Number 66556-77-2
Molecular Formula C19H15NO6
Formula Weight 353.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C1C([C@@]​(CC(C)​=O)​([H]​)​C2=CC=C([N+]​([O-]​)​=O)​C=C2)​=C(O)​C3=CC=CC=C3O1

Background Reading

Ufer, M. Comparative pharmacokinetics of vitamin K antagonists warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet 44(12) 1227-1246 (2005).
Size Price Quantity Subtotal
1 mg $135.00 $0.00
5 mg $608.00 $0.00
10 mg $1,080.00 $0.00
25 mg $2,363.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Related Products

Acenocoumarol
(S)-(−)-Acenocoumarol
(−)-Warfarin
(+)-Warfarin
(±)-Warfarin
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