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Merck
CN
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安全信息

UC213

Sigma-Aldrich

(R)-(+)-Warfarin

≥97% (HPLC)

别名:

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

经验公式（希尔记法）:
C19H16O4
CAS号:
5543-58-8
分子量:
308.33
EC 号:
226-908-9
MDL编号:
MFCD00272376
UNSPSC代码:
12161501
PubChem化学物质编号:
24724649

方案

≥97% (HPLC)

表单

solid

颜色

white to pale yellow

mp

≥170 °C

溶解性

DMF: soluble
DMSO: soluble
ethanol: soluble

储存温度

2-8°C

SMILES字符串

[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

InChI key

PJVWKTKQMONHTI-OAHLLOKOSA-N

基因信息

human ... CYP2C9(1559)

一般描述

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.

应用

(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

生化/生理作用

CYP1A2/3A4 substrate; anticoagulant.
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.

包装

Bottomless glass bottle. Contents are inside inserted fused cone.

制备说明

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

应用

产品编号
说明
价格

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

警示用语：

Danger

危险分类

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

靶器官

Blood

储存分类代码

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

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

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

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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.
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)
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
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
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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实验方案

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

This 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 SFCapplication for SFC展开

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