(S)-(-)-WARFARIN
(S)-(-)-WARFARIN Basic information
- Product Name:
- (S)-(-)-WARFARIN
- Synonyms:
-
- Coumarin, 3-(a-acetonylbenzyl)-4-hydroxy-, (S)-(-)- (8CI)
- 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-chromen-2-one
- S-(-)-3-Acetonybenzyl)-4-hydroxycoumarin, S-(-)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one
- (-)-3-[(S)-1-Phenyl-3-oxobutyl]-4-hydroxycoumarin
- (-)-3-[(S)-α-Acetonylbenzyl]-4-hydroxycoumarin
- (-)-4-Hydroxy-3-[(S)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one
- 2-hydroxy-3-(3-keto-1-phenyl-butyl)chromone
- 2-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-4-one
- CAS:
- 5543-57-7
- MF:
- C19H16O4
- MW:
- 308.33
- EINECS:
- 226-907-3
- Product Categories:
-
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Aromatics
- Chiral Reagents
- Heterocycles
- Mol File:
- 5543-57-7.mol
(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
- Language:English Provider:SigmaAldrich
(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.
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(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