The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: in vitro studies using human liver microsomes

Br J Clin Pharmacol. 1994 Sep;38(3):243-8. doi: 10.1111/j.1365-2125.1994.tb04348.x.

Abstract

1. The enzyme kinetics of dextromethorphan O-demethylation in liver microsomes from three extensive metabolisers (EM) with respect to CYP2D6 indicated high (Km1 2.2-9.4 microM) and low (Km2 55.5-307.3 microM) affinity sites whereas microsomes from two poor metabolisers (PM) indicated a single site (Km 560 and 157 microM). Similar differences were shown for 3-methoxymorphinan O-demethylation to 3-hydroxymorphinan (Km 6.9-9.6 microM in EM subjects; Km 307 and 213 microM in PM subjects). 2. Dextromethorphan O-demethylation was inhibited competitively by quinidine (Ki 0.1 microM), rac-perhexiline (Ki 0.4 microM), dextropropoxyphene (Ki 6 microM), rac-methadone (Ki 8 microM), and 3-methoxymorphinan (Ki 15 microM). These compounds were also potent inhibitors of 3-methoxymorphinan O-demethylation with IC50 values ranging from 0.02-12 microM. Anti-LKM1 serum inhibited both dextromethorphan and 3-methoxymorphinan O-demethylations in a titre-dependent manner. 3. The Michaelis-Menten constant for dextromethorphan N-demethylation to 3-methoxymorphinan (Km 632-977 microM) and dextrorphan N-demethylation to 3-hydroxymorphinan (Km 1571-4286 microM) did not differ between EM and PM microsomes. These N-demethylation reactions were not inhibited by quinidine and rac-methadone or LKM1 antibodies. 4. Dextromethorphan and 3-methoxymorphinan are metabolised by the same P450 isoform, CYP2D6, whereas the N-demethylation reactions are not carried out by CYP2D6.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Autoantibodies / immunology
  • Binding, Competitive
  • Cytochrome P-450 CYP2D6
  • Cytochrome P-450 Enzyme System / metabolism*
  • Dextromethorphan / analogs & derivatives
  • Dextromethorphan / chemistry
  • Dextromethorphan / metabolism*
  • Dextromethorphan / pharmacology
  • Dextropropoxyphene / pharmacology
  • Dextrorphan / metabolism
  • Humans
  • In Vitro Techniques
  • Methadone / pharmacology
  • Methylation / drug effects
  • Microsomes, Liver / drug effects*
  • Microsomes, Liver / enzymology
  • Mixed Function Oxygenases / metabolism*
  • Oxidation-Reduction
  • Perhexiline / pharmacology
  • Phenotype
  • Quinidine / pharmacology

Substances

  • Autoantibodies
  • anti-liver kidney microsome antibody
  • Dextrorphan
  • 3-methoxymorphinan
  • Dextromethorphan
  • Cytochrome P-450 Enzyme System
  • Mixed Function Oxygenases
  • Cytochrome P-450 CYP2D6
  • norlevorphanol
  • Quinidine
  • Perhexiline
  • Dextropropoxyphene
  • Methadone