Pre-systemic elimination of tilidine: localization and consequences for the formation of the active metabolite nortilidine

Basic Clin Pharmacol Toxicol. 2015 Feb;116(2):129-33. doi: 10.1111/bcpt.12328. Epub 2014 Oct 7.

Abstract

The therapeutic activity of tilidine, an opioid analgesic, is mainly related to its active metabolite nortilidine. Nortilidine formation mainly occurs during the high intestinal first-pass metabolism of tilidine by N-demethylation. Elimination of the active nortilidine to the inactive bisnortilidine is also mediated by N-demethylation and is supposed to take place in the liver, probably at a smaller rate. The aim of this study was the investigation of the pre-systemic elimination of tilidine using grapefruit juice (GFJ) as an intestinal CYP3A4 inhibitor and efavirenz (EFV) as a CYP3A4 activator. A randomized, open, placebo-controlled, cross-over study was conducted in 12 healthy volunteers using 100 mg tilidine solution p.o., regular strength GFJ 250 mL (3 times at 12-hr intervals) and EFV 400 mg (12 hr before tilidine administration). Tilidine, nortilidine and bisnortilidine in plasma and urine were quantified by a validated LC/MS/MS analysis. GFJ did not change any pharmacokinetic parameter of tilidine and its metabolites, which suggests that intestinal CYP3A4 does not contribute to the first-pass metabolism of tilidine. No effect of EFV on the pharmacokinetics of the active nortilidine was observed except a significant reduction of the terminal elimination half-life by 15%. Overall elimination (renal and metabolic clearances) was unaffected by every treatment. CYP3A4 does not seem to play a major role in tilidine first-pass and overall metabolism. Other unknown metabolites and their enzymes responsible for their formation have to be investigated as they account for the majority of renally excreted metabolites.

Publication types

  • Randomized Controlled Trial

MeSH terms

  • Adult
  • Alkynes
  • Analgesics, Opioid / pharmacokinetics*
  • Benzoxazines / pharmacology
  • Beverages
  • Chromatography, Liquid / methods
  • Citrus paradisi
  • Cross-Over Studies
  • Cyclopropanes
  • Cytochrome P-450 CYP3A / metabolism*
  • Female
  • Half-Life
  • Humans
  • Male
  • Middle Aged
  • Tandem Mass Spectrometry / methods
  • Tilidine / analogs & derivatives*
  • Tilidine / pharmacokinetics
  • Young Adult

Substances

  • Alkynes
  • Analgesics, Opioid
  • Benzoxazines
  • Cyclopropanes
  • bisnortilidine
  • nortilidine
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Tilidine
  • efavirenz