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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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250 REACTIONS
CN¥2,108.32
1250 REACTIONS
CN¥9,461.07

CN¥2,108.32

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250 REACTIONS
CN¥2,108.32
1250 REACTIONS
CN¥9,461.07

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

CN¥2,108.32

Please contact Customer Service for Availability
New, lower price on this item!
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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)

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form

liquid

form

liquid

form

liquid

form

liquid

usage

sufficient for 1250 reactions

usage

sufficient for 1250 reactions, sufficient for 250 reactions, sufficient for 5000 reactions

usage

sufficient for 1250 reactions, sufficient for 250 reactions, sufficient for 5000 reactions

usage

sufficient for 500 reactions

feature

dNTPs included

feature

dNTPs included, hotstart

feature

dNTPs included, hotstart

feature

dNTPs included, hotstart

storage condition

protect from light

storage condition

protect from light

storage condition

protect from light

storage condition

protect from light

color

light blue

color

light blue

color

light blue

color

light blue

General description

Warfarin is an antagonist of vitamin K. It is an oral coumarin anticoagulant.[1]

Application

(S)-(−)-Warfarin has been used in cell cultures.[2]
Studies using (R)-(+)-warfarin have reported that it can upregulate hepatic CYP3A4 and CYP2C[1]. It has also been used in HepG2 cells to study protein profiles[3].

Biochem/physiol Actions

CYP2C9 substrate; anticoagulant.
Warfarin is used to regulate and inhibit thromboembolic disorders.[1] The CYP2C9 (cytochrome P450 family 2 subfamily C member 9) protein plays a major role in the inactivation of potent S-warfarin.[4]

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

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000164876
    0000180445
    0000164876
    0000180445
    1385525V

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    Pharmacogenetics
    Cardiovascular Therapeutics: A Companion to Braunwald's Heart Disease (2013)
    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
    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)
    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
    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

    application for SFCapplication for SFCapplication for HPLCapplication for HPLCShow More

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