UC213

(R)-(+)-Warfarin

≥97% (HPLC)

• Synonyme(s) : R-(+)-3-Acetonybenzyl)-4-hydroxycoumarin, R-(+)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one
• Formule empirique (notation de Hill) : C₁₉H₁₆O₄
• CAS Number: 5543-58-8
• Poids moléculaire : 308.33
• Numéro CE : 226-908-9
• Numéro MDL: MFCD00272376
• Code UNSPSC : 12161501
• ID de substance PubChem : 24724649

Propriétés

• Essai: ≥97% (HPLC)
• Forme: solid
• Couleur: white to pale yellow
• Pf: ≥170 °C
• Solubilité: DMF: soluble; DMSO: soluble; ethanol: soluble
• Température de stockage: 2-8°C
• Chaîne SMILES: [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
• Clé InChI: PJVWKTKQMONHTI-OAHLLOKOSA-N
• Informations sur le gène: human ... CYP2C9(1559)

Description

Description générale

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.

Application

(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

Actions biochimiques/physiologiques

CYP1A2/3A4 substrate; anticoagulant.

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Notes préparatoires

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

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H300 + H310 + H330,H360D,H372,H411
• Conseils de prudence: P202 - P264 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Classification des risques: Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Aquatic Chronic 2 - Repr. 1A - STOT RE 1
• Organes cibles: Blood
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable