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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

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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’.

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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)
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.
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

Chromatograms

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