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UC213

Sigma-Aldrich

(R)-(+)-Warfarin

≥97% (HPLC)

Synonym(e):

R-(+)-3-Acetonybenzyl)-4-hydroxycoumarin, R-(+)-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:
5543-58-8
Molekulargewicht:
308.33
EG-Nummer:
226-908-9
MDL-Nummer:
MFCD00272376
UNSPSC-Code:
12161501
PubChem Substanz-ID:
24724649

Assay

≥97% (HPLC)

Form

solid

Farbe

white to pale yellow

mp (Schmelzpunkt)

≥170 °C

Löslichkeit

DMF: soluble
DMSO: soluble
ethanol: soluble

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-/m1/s1

InChIKey

PJVWKTKQMONHTI-OAHLLOKOSA-N

Angaben zum Gen

human ... CYP2C9(1559)

Allgemeine Beschreibung

The chiral carbon at position 9 produces two enantiomers, R- and S-warfarin. Commercially available warfarin (Coumadin or Jantoven) is a racemic mixture of S- and R-enantiomers.

Anwendung

(R)-(+)-warfarin has been used to investigate whether enantiomers of warfarin stereoselectively interact with pregnane X nuclear receptor (PXR) to upregulate main drug/xenobiotic-metabolizing enzymes cytochrome P450 3A4 (CYP3A4) and cytochrome P450 2C9 (CYP2C9). It has also been used in HepG2 cells to study protein profiles

Biochem./physiol. Wirkung

Warfarin acts as a vitamin K antagonist. It is widely used to treat thromboembolic disorders. (R)-warfarin interacts with pregnane X receptor (PXR) and induces cytochrome P450 3A4 (CYP3A4) and CYP2C9 mRNAs expression in primary human hepatocyte cultures.
CYP1A2/3A4 substrate; anticoagulant.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Angaben zur Herstellung

(+)-Warfarin is soluble in DMF, DMSO and ethanol.

Anwendung

Produkt-Nr.
Beschreibung
Preisangaben

G004472

HPLC Analysis of Warfarin Enantiomers on Astec® CHIROBIOTIC® V (Method 1), application for HPLC

G004475

HPLC Analysis of Warfarin Enantiomers on Astec® CHIROBIOTIC® V2, application for HPLC

G004649

HPLC Analysis of Warfarin Enantiomers on Astec® CHIROBIOTIC® V (Method 2), application for HPLC

G005007

HPLC Analysis of Warfarin Enantiomers on Astec® Cellulose DMP, application for HPLC

G005008

HPLC Analysis of Warfarin Enantiomers on Astec® CYCLOBOND I 2000 (UV at 278 nm), application for HPLC

G005170

SFC Analysis of Warfarin Enantiomers on Astec® Cellulose DMP, Methanol Additive, application for SFC

G005171

SFC Analysis of Warfarin Enantiomers on Astec® Cellulose DMP, Ethanol Additive, application for SFC

G005174

SFC Analysis of Warfarin Enantiomers on Astec® Cellulose DMP, Methanol Gradient, application for SFC

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

Zulassungslistungen

Zulassungslistungen werden hauptsächlich für chemische Produkte erstellt. Für nicht-chemische Produkte können hier nur begrenzte Angaben gemacht werden. Kein Eintrag bedeutet, dass keine der Komponenten gelistet ist. Es liegt in der Verantwortung des Benutzers, die sichere und legale Verwendung des Produkts zu gewährleisten.

EU REACH Annex XVII (Restriction List)

CAS No.

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
483-136-2V
483-136-2
053M3903V
053M3903
065K3259-1

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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)
Jing Bai et al.
Metabolomics : Official journal of the Metabolomic Society, 7(3), 353-362 (2011-09-29)
Warfarin is a commonly prescribed oral anticoagulant with narrow therapeutic index. It achieves anti-coagulating effects by interfering with the vitamin K cycle. Warfarin has two enantiomers, S(-) and R(+) and undergoes stereoselective metabolism, with the S(-) enantiomer being more effective.
Konstantin Doronin et al.
Human gene therapy, 20(9), 975-988 (2009-05-28)
Oncolytic adenoviruses are anticancer agents that replicate within tumors and spread to uninfected tumor cells, amplifying the anticancer effect of initial transduction. We tested whether coating the viral particle with polyethylene glycol (PEG) could reduce transduction of hepatocytes and hepatotoxicity
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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