Identification of 1-furan-2-yl-3-pyridin-2-yl-propenone, an antiinflammatory agent, and its metabolites in rat liver subcellular fractions

Arch Pharm Res. 2006 Nov;29(11):984-9. doi: 10.1007/BF02969282.

Abstract

1-Furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) has been characterized to have an anti-inflammatory activity through the inhibition of the production of nitric oxide and tumor necrosis factor-alpha. In the present studies, the phase 1 metabolism of FPP-3 was investigated in rat liver microsomes and cytosols. When FPP-3 was incubated with rat liver microsomes and cytosols in the presence of NADPH, 2 major peaks were detected on a liquid chromatography/electrospray ionization-mass spectrometry. Two metabolites (i.e., M1 and M2) were characterized as reduced forms on propenone: M1 (1-furan-2-yl-3-pyridin-2-yl-propan-1-one) was the initial metabolite and M2 (1-furan-2-yl-3-pyridin-2-yl-propan-l-ol) was a secondary alcohol believed to be formed from M1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / pharmacokinetics*
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Cytosol / metabolism
  • Furans / pharmacokinetics*
  • In Vitro Techniques
  • Liver / metabolism*
  • Magnetic Resonance Spectroscopy
  • Male
  • Microsomes, Liver / metabolism
  • Oxidation-Reduction
  • Propane / analogs & derivatives*
  • Propane / pharmacokinetics
  • Pyridines / pharmacokinetics*
  • Rats
  • Rats, Sprague-Dawley
  • Spectrometry, Mass, Electrospray Ionization
  • Subcellular Fractions / metabolism*

Substances

  • 1-furan-2-yl-3-pyridin-2-yl-propenone
  • Anti-Inflammatory Agents
  • Furans
  • Pyridines
  • Propane