Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

UC214

Sigma-Aldrich

(S)-(−)-Warfarin

≥97% (HPLC)

Synonym(s):

S-(−)-3-Acetonybenzyl)-4-hydroxycoumarin, S-(−)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C19H16O4
CAS Number:
5543-57-7
Molecular Weight:
308.33
EC Number:
226-907-3
MDL number:
MFCD00272381
UNSPSC Code:
12161501
PubChem Substance ID:
24724650
NACRES:
NA.77

Assay

≥97% (HPLC)

form

solid

color

white to pale yellow

mp

≥170 °C

storage temp.

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-/m0/s1

InChI key

PJVWKTKQMONHTI-HNNXBMFYSA-N

Gene Information

human ... CYP2C9(1559)

General description

Warfarin is an antagonist of vitamin K. It is an oral coumarin anticoagulant.

Application

(S)-(−)-Warfarin has been used in cell cultures.
Studies using (R)-(+)-warfarin have reported that it can upregulate hepatic CYP3A4 and CYP2C. It has also been used in HepG2 cells to study protein profiles.

Biochem/physiol Actions

Warfarin is used to regulate and inhibit thromboembolic disorders. The CYP2C9 (cytochrome P450 family 2 subfamily C member 9) protein plays a major role in the inactivation of potent S-warfarin.
CYP2C9 substrate; anticoagulant.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Signal Word

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

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Jeng-Jong Shieh et al.
Journal of pharmaceutical sciences, 109(2), 1191-1198 (2019-11-13)
MB-102 is a fluorescent tracer agent designed for measurement of point-of-care glomerular filtration rate (GFR) and is currently in clinical studies. MB-102 possesses a strong UV absorbance at 266 nm and 435 nm, and broad fluorescent emission at ~560 nm
Pharmacogenetics
Cardiovascular Therapeutics: A Companion to Braunwald's Heart Disease (2013)
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
View All Related Papers

Protocols

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

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

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

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 SFCapplication for SFCapplication for HPLCapplication for HPLCShow More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service