Identification of cytochrome P450 enzymes involved in the metabolism of the new designer drug 4'-methyl-alpha-pyrrolidinobutyrophenone

Drug Metab Dispos. 2008 Jan;36(1):163-8. doi: 10.1124/dmd.107.017293. Epub 2007 Oct 25.

Abstract

The involvement of human hepatic cytochrome P450 (P450) isoenzymes in the metabolism of the new designer drug 4'-methyl-alpha-pyrrolidinobutyrophenone (MPBP) to 4'-(hydroxymethyl)-alpha-pyrrolidinobutyrophenone (HO-MPBP) was studied using insect cell microsomes with cDNA-expressed human P450s and human liver microsomes (HLM). Incubation samples were analyzed by liquid chromatography-mass spectrometry. Only CYP2D6, CYP2C19, and CYP1A2 were capable of catalyzing MPBP 4'-hydroxylation. According to the relative activity factor approach, these enzymes accounted for 54, 30, and 16% of net clearance. At 1 microM MPBP, the chemical inhibitors quinidine (CYP2D6), fluconazole (CYP2C19), and alpha-naphthoflavone (CYP1A2) reduced metabolite formation in pooled HLM by 83, 53, and 47%, respectively, and at 50 microM MPBP by 41, 47, and 45%, respectively. In experiments with HLM from CYP2D6 and CYP2C19 poor metabolizers, HO-MPBP formation was found to be 78 and 79% lower in comparison with pooled HLM, respectively. From these data, it can be concluded that polymorphically expressed CYP2D6 is mainly responsible for MPBP hydroxylation.

MeSH terms

  • Animals
  • Baculoviridae / genetics
  • Butyrophenones / metabolism*
  • Butyrophenones / pharmacokinetics
  • Chromatography, Liquid
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism*
  • Designer Drugs / metabolism*
  • Designer Drugs / pharmacokinetics
  • Enzyme Inhibitors / pharmacology
  • Genetic Vectors
  • Humans
  • Hydroxylation
  • Insecta / genetics
  • Isoenzymes
  • Mass Spectrometry
  • Microsomes, Liver / enzymology*
  • Pyrrolidines / metabolism*
  • Pyrrolidines / pharmacokinetics
  • Transfection

Substances

  • 4'-methyl-alpha-pyrrolidinobutyrophenone
  • Butyrophenones
  • Cytochrome P-450 Enzyme Inhibitors
  • Designer Drugs
  • Enzyme Inhibitors
  • Isoenzymes
  • Pyrrolidines
  • Cytochrome P-450 Enzyme System