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Key Documents

UC213

Sigma-Aldrich

(R)-(+)-Warfarin

≥97% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C19H16O4
Numero CAS:
Peso molecolare:
308.33
Numero CE:
Numero MDL:
Codice UNSPSC:
12161501
ID PubChem:

Saggio

≥97% (HPLC)

Forma fisica

solid

Colore

white to pale yellow

Punto di fusione

≥170 °C

Solubilità

DMF: soluble
DMSO: soluble
ethanol: soluble

Temperatura di conservazione

2-8°C

Stringa SMILE

[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-/m1/s1
PJVWKTKQMONHTI-OAHLLOKOSA-N

Informazioni sul gene

human ... CYP2C9(1559)

Descrizione generale

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.

Applicazioni

(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

Azioni biochim/fisiol

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.
CYP1A2/3A4 substrate; anticoagulant.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Nota sulla preparazione

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

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

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

Organi bersaglio

Blood

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (COA)

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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)
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
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.
Konstantin Doronin et al.
Human gene therapy, 20(9), 975-988 (2009-05-28)
Oncolytic adenoviruses are anticancer agents that replicate within tumors and spread to uninfected tumor cells, amplifying the anticancer effect of initial transduction. We tested whether coating the viral particle with polyethylene glycol (PEG) could reduce transduction of hepatocytes and hepatotoxicity

Protocolli

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

application for HPLCapplication for HPLCapplication for HPLCapplication for HPLCMostra di più

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