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UC213

Sigma-Aldrich

(R)-(+)-Warfarin

≥97% (HPLC)

Sinônimo(s):

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

Fórmula empírica (Notação de Hill):
C19H16O4
Número CAS:
5543-58-8
Peso molecular:
308.33
Número CE:
226-908-9
Número MDL:
MFCD00272376
Código UNSPSC:
12161501
ID de substância PubChem:
24724649

Ensaio

≥97% (HPLC)

forma

solid

cor

white to pale yellow

pf

≥170 °C

solubilidade

DMF: soluble
DMSO: soluble
ethanol: soluble

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

[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

chave InChI

PJVWKTKQMONHTI-OAHLLOKOSA-N

Informações sobre genes

human ... CYP2C9(1559)

Descrição geral

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.

Aplicação

(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

Ações bioquímicas/fisiológicas

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.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Nota de preparo

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

Aplicação

Nº do produto
Descrição
Preços

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

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Blood

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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)
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
Michelle J Yoo et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 877(11-12), 1149-1154 (2009-03-31)
Binding by the drug imipramine to the protein human serum albumin (HSA) was studied by using high-performance affinity chromatography. The association equilibrium constants and number of binding sites for imipramine with HSA were first estimated by utilizing frontal analysis. Imipramine
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.
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
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Protocolos

Chiral and Achiral LC-MS Analysis of Warfarin™ in Plasma Samples

his study demonstrates the analysis of Warfarin in plasma samples utilizing chiral and achiral (reversed-phase) LC-MS and effective sample prep to remove endogenous phospholipids

Chromatograms

application for HPLCapplication for HPLCapplication for HPLCapplication for HPLCMostrar mais

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