UC213

(R)-(+)-Warfarin

Name: (R)-(+)-Warfarin
Brand: SIGMA

≥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 Number:

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

主要文件

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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.