A new warfarin metabolite: structure and function

J Med Chem. 1978 Oct;21(10):1054-9. doi: 10.1021/jm00208a009.

Abstract

The metabolism of the clinically utilized, anticoagulant warfarin [4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one] by rat liver microsomes has been investigated. The structure of a new warfarin metabolite [4-hydroxy-3-(3-oxo-1-phenyl-1-butenyl)-2H-1-benzopyran-2-one] (dehydrowarfarin) has been determined by mass spectral comparison with the chemically synthesized compound. The formation of dehydrowarfarin is catalyzed by cytochrome P-450 and is unusual in that the final product is effectively dehydrogenated warfarin.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Blood Coagulation / drug effects
  • Chemical Phenomena
  • Chemistry
  • Cytochrome P-450 Enzyme System / metabolism
  • Enzyme Induction / drug effects
  • In Vitro Techniques
  • Microsomes, Liver / metabolism
  • Mutagens
  • Rats
  • Salmonella / drug effects
  • Salmonella / genetics
  • Stereoisomerism
  • Vitamin K 1 / antagonists & inhibitors
  • Warfarin / chemical synthesis
  • Warfarin / metabolism*
  • Warfarin / pharmacology

Substances

  • Mutagens
  • Warfarin
  • Vitamin K 1
  • Cytochrome P-450 Enzyme System