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Merck

UC214

Sigma-Aldrich

(S)-(−)-Warfarin

≥97% (HPLC)

Synonym(e):

S-(−)-3-Acetonybenzyl)-4-hydroxycoumarin, S-(−)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one

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About This Item

Empirische Formel (Hill-System):
C19H16O4
CAS-Nummer:
Molekulargewicht:
308.33
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12161501
PubChem Substanz-ID:
NACRES:
NA.77

Assay

≥97% (HPLC)

Form

solid

Farbe

white to pale yellow

mp (Schmelzpunkt)

≥170 °C

Lagertemp.

2-8°C

SMILES String

[H][C@](CC(C)=O)(c1ccccc1)C2=C(O)c3ccccc3OC2=O

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

InChIKey

PJVWKTKQMONHTI-HNNXBMFYSA-N

Angaben zum Gen

human ... CYP2C9(1559)

Allgemeine Beschreibung

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

Anwendung

(S)-(−)-Warfarin has been used in cell cultures.
Studies using (R)-(+)-warfarin have reported that it can upregulate hepatic CYP3A4 and CYP2C. It has also been used in HepG2 cells to study protein profiles.

Biochem./physiol. Wirkung

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.
CYP2C9 substrate; anticoagulant.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Chronic 2 - Repr. 1A - STOT RE 1

Zielorgane

Blood

Lagerklassenschlüssel

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Kunden haben sich ebenfalls angesehen

Metabolic profiling of HepG2 cells incubated with S (-) and R (+) enantiomers of anti-coagulating drug warfarin
Bai J, et al.
Metabolomics, 7(3), 353-362 (2011)
Jeng-Jong Shieh et al.
Journal of pharmaceutical sciences, 109(2), 1191-1198 (2019-11-13)
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Pharmacogenetics
Cardiovascular Therapeutics: A Companion to Braunwald's Heart Disease (2013)
Jing Bai et al.
Proteomics. Clinical applications, 4(10-11), 808-815 (2010-12-08)
warfarin is a commonly prescribed oral anticoagulant with narrow therapeutic index. It interferes with the vitamin K cycle to achieve anti-coagulating effects. Warfarin has two enantiomers, S(-) and R(+) and undergoes stereoselective metabolism, with the S(-) enantiomer being more effective.
A Rulcova et al.
Journal of thrombosis and haemostasis : JTH, 8(12), 2708-2717 (2010-08-26)
Warfarin, an antagonist of vitamin K, is an oral coumarin anticoagulant widely used to control and prevent thromboembolic disorders. Warfarin is clinically available as a racemic mixture of R- and S-warfarin. The S-enantiomer has three to five times greater anticoagulation

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