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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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)
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
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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Protocols

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

his 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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