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Merck
CN

UC213

(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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关于此项目

经验公式（希尔记法）:
C19H16O4
化学文摘社编号:
5543-58-8
分子量:
308.33
UNSPSC Code:
12161501
PubChem Substance ID:
24724649
EC Number:
226-908-9
MDL number:
MFCD00272376

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产品名称

(R)-(+)-Warfarin, ≥97% (HPLC)

InChI key

PJVWKTKQMONHTI-OAHLLOKOSA-N

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

SMILES string

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

assay

≥97% (HPLC)

form

solid

color

white to pale yellow

mp

≥170 °C

solubility

DMF: soluble
DMSO: soluble
ethanol: soluble

storage temp.

2-8°C

Gene Information

human ... CYP2C9(1559)

Application

(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 Actions

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.

General description

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

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

signalword

Danger

Hazard Classifications

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

target_organs

Blood

存储类别

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(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.
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
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.
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
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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

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