UC213

(R)-(+)-Warfarin

≥97% (HPLC)

• Synonym(s): R-(+)-3-Acetonybenzyl)-4-hydroxycoumarin, R-(+)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one
• Empirical Formula (Hill Notation): C₁₉H₁₆O₄
• CAS Number: 5543-58-8
• Molecular Weight: 308.33
• EC Number: 226-908-9
• MDL number: MFCD00272376
• UNSPSC Code: 12161501
• PubChem Substance ID: 24724649

Properties

• Assay: ≥97% (HPLC)
• form: solid
• color: white to pale yellow
• mp: ≥170 °C
• solubility: DMF: soluble; DMSO: soluble; ethanol: soluble
• 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-/m1/s1
• InChI key: PJVWKTKQMONHTI-OAHLLOKOSA-N
• Gene Information: human ... CYP2C9(1559)

Description

General description

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

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

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

Safety Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H300 + H310 + H330,H360D,H372,H411
• Precautionary Statements: P202 - P264 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• 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