Isolation of a major metabolite (i-OHAP) of aprindine and its identification as N-[3-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol

Biol Pharm Bull. 1998 May;21(5):530-4. doi: 10.1248/bpb.21.530.

Abstract

i-OHAP, a major metabolite of aprindine (AP), was isolated by TLC from rat feces and identified as N-13-(N,N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol, based on 1H-NMR, the H-H correlation spectroscopy (COSY) spectrum, MS and LC-MS. Its structure was also confirmed by comparison with the synthesized compound. The hydroxy group of i-OHAP was located at the 5-position of the indan ring. AP is a prochiral compound, and the metabolism of AP to i-OHAP was stereoselective. The ratio of (+)/(-)-i-OHAP in rat feces and in human urine was about 5 and 15, respectively.

Publication types

  • Clinical Trial

MeSH terms

  • Adult
  • Animals
  • Anti-Arrhythmia Agents / pharmacokinetics*
  • Aprindine / analogs & derivatives*
  • Aprindine / metabolism
  • Aprindine / pharmacokinetics*
  • Aprindine / urine
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Feces / chemistry
  • Female
  • Humans
  • Magnetic Resonance Spectroscopy
  • Male
  • Rats
  • Rats, Wistar
  • Stereoisomerism

Substances

  • Anti-Arrhythmia Agents
  • N-(3-(N,N-diethylamino)propyl)-N-phenyl-2-aminoindan-5-ol
  • Aprindine