An anticoagulant
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(−)-Warfarin

Item No. 13531

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-3-[(1S)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one
CAS Number
5543-57-7
Synonyms
  • (S)-Warfarin
Molecular Formula
C19H16O4
Formula Weight
308.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 5 mg/ml
λmax
206, 272, 283, 306 nm
SMILES
CC(=O)C[C@@H](c1ccccc1)c1c(=O)oc2ccccc2c1O
InChi Code
InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3/t15-/m0/s1
InChi Key
PJVWKTKQMONHTI-HNNXBMFYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $82

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    5 mg

    $266

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    10 mg

    $489

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    25 mg

    $1,018

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    Product Description

    (–)-Warfarin is a component of (±)-warfarin (Item No. 13566). It is an anticoagulant that interferes with interconversion of vitamin K and vitamin K epoxide and the role of vitamin K in carboxylation of several clotting cascade proteins, inhibiting the initiation of clotting.1 In vivo, (–)-warfarin slows formation of the prothrombin complex and exhibits 6.6-fold more potent anticoagulant activity than (+)-warfarin (Item No. 13526) in rats.2 (–)-Warfarin is primarily metabolized by the cytochrome P450 (CYP) isoform CYP2C9 and genetic polymorphisms in this enyzme, as well as other compounds metabolized by CYP2C9, increase the potential for catastrophic bleeding complications. Formulations containing warfarin have been used to treat and prevent blood clots in atrial fibrillation, heart valve replacement, venous thrombosis, and pulmonary embolism.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hirsh, J., Fuster, V., Ansell, J., et al. American heart association/american college of cardiology foundation guide to warfarin therapy. J. Am. Coll. Cardiol. 41(9), 1633-1652 (2003).

    2. Breckenridge, A., and Orme, M.L. The plasma half lives and the pharmacological effect of the enantiomers of warfarin in rats. Life Sci. II 11(7), 337-345 (1972).

    Product Citations

    Shiozawa, A., Yamaori, S., Kamijo, S., et al. Effects of acid and lactone forms of statins on S-warfarin 7-hydroxylation catalyzed by human liver microsomes and recombinant CYP2C9 variants (CYP2C9.1 and CYP2C9.3). Drug Metab. Pharmacokinet. 36, 100364 (2021).