(S)-(-)-WARFARIN Chemical Properties

Melting point:

≥170 °C

storage temp. 

2-8°C

solubility 

DMF: 25 mg/ml; DMSO: 25 mg/ml; Ethanol: 5 mg/ml

form 

A crystalline solid

color 

white to pale yellow

CAS DataBase Reference

5543-57-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

61-48/25-52/53

Safety Statements 

53-45-61

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

MSDS

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(S)-(-)-WARFARIN Usage And Synthesis

Description

(–)-Warfarin is a component of (±)-warfarin . 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. In vivo, (–)-warfarin slows formation of the prothrombin complex and exhibits 6.6-fold more potent anticoagulant activity than (+)-warfarin in rats. (–)-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.

Chemical Properties

White Solid

Uses

The S-(-)-form of Warfarin (W498500). Coumarin anticoagulant.

Uses

(S)-(?)-Warfarin has been used in cell cultures.

Definition

ChEBI: (S)-warfarin is a 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one that has (S)-configuration (the racemate is warfarin, an anticoagulant drug and rodenticide). It is a conjugate acid of a (S)-warfarin(1-). It is an enantiomer of a (R)-warfarin.

General Description

Warfarin is an antagonist of vitamin K. It is an oral coumarin anticoagulant.

Biochem/physiol Actions

Warfarin is used to regulate and inhibit thromboembolic disorders. The CYP2C9 (cytochrome P450 family 2 subfamily C member 9)?protein plays a major role in the inactivation of potent S-warfarin.

References

[1] A. BRECKENRIDGE  M. L O. The plasma half lives and the pharmacological effect of the enantiomers of warfarin in rats[J]. Life sciences, 1972, 11 7: Pages 337-345. DOI: 10.1016/0024-3205(72)90073-2
[2] AYAKA SHIOZAWA . 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)[J]. Drug Metabolism and Pharmacokinetics, 2021, 36: Article 100364. DOI: 10.1016/j.dmpk.2020.10.003

(S)-(-)-WARFARIN(5543-57-7)Related Product Information

• Warfarin
• 4-Hydroxycoumarin
• 4,4'-(Disulfanediyl)bis(2,6-di-tert-butylphenol)
• (S)-8-Hydroxy Warfarin
• 6-HYDROXYWARFARIN
• (R)-6-Hydroxy Warfarin
• 3-(o-Hydroxyphenyl)-5-phenyl-2-cyclohexen-1-one
• Benzalacetone
• 3-[α-(2-Hydroxypropyl)benzyl]-4-hydroxycouMarin
• (R)-7-Hydroxy Warfarin
• 7-HYDROXYWARFARIN
• (S)-6-Hydroxy Warfarin
• Warfarin Impurity 1
• 8-HYDROXYWARFARIN
• 2,6-Di-tert-butyl-4-mercaptophenol
• 7-HYDROXYWARFARIN
• (R)-(+)-WARFARIN,(R)-WARFARIN
• (R)-8-HYDROXY WARFARIN