Human cytochromes mediating gepirone biotransformation at low substrate concentrations

Biopharm Drug Dispos. 2003 Mar;24(2):87-94. doi: 10.1002/bdd.340.

Abstract

Biotransformation of gepirone to 1-(2-pyrimidinyl)-piperazine (1-PP) and 3'-OH-gepirone, as well as two other hydroxylated metabolites, was studied in vitro using a human liver microsomal preparation and heterologously expressed human CYP3A4 and CYP2D6. The focus was on a low range of gepirone concentrations (1000 nM and below). Liver microsomes formed 1-PP and 3'-OH-gepirone with similar reaction velocities. Two other hydroxylated metabolites (2-OH- and 5-OH-gepirone) were also formed, but pure reference standards were not available for purposes of quantitative analysis. The CYP3A inhibitor ketoconazole completely eliminated 1-PP formation, reduced 3'-OH-gepirone formation to less than 20% of control, and reduced 2-OH-gepirone formation to 7% of control. All metabolites were formed by expressed CYP3A4; however, CYP2D6 formed 3'-OH- and 5-OH-gepirone, but not 1-PP or 2-OH-gepirone. Based on estimated relative abundances of the two isoforms in human liver, CYP3A4 was predicted to account for more than 95% of net clearance of gepirone in vivo at low concentrations approaching the therapeutic range. CYP2D6 would account for less than 5% of net clearance. The findings are consistent with previous in vitro studies of gepirone using higher substrate concentrations.

Publication types

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

MeSH terms

  • Biotransformation
  • Buspirone / analogs & derivatives*
  • Buspirone / metabolism
  • Cytochrome P-450 CYP2D6 / metabolism*
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 Enzyme System / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • In Vitro Techniques
  • Microsomes, Liver / metabolism
  • Piperidones / metabolism
  • Pyrimidines / metabolism
  • Pyrimidines / pharmacokinetics*
  • Serotonin Receptor Agonists / metabolism
  • Serotonin Receptor Agonists / pharmacokinetics*

Substances

  • 2-hydroxygepirone
  • 3'-hydroxygepirone
  • 5-hydroxygepirone
  • Piperidones
  • Pyrimidines
  • Serotonin Receptor Agonists
  • Cytochrome P-450 Enzyme System
  • CYP3A protein, human
  • Cytochrome P-450 CYP2D6
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • 1-(2-pyrimidinyl)piperazine
  • gepirone
  • Buspirone