Different in vitro metabolism of paclitaxel and docetaxel in humans, rats, pigs, and minipigs

Drug Metab Dispos. 2004 Jun;32(6):666-74. doi: 10.1124/dmd.32.6.666.

Abstract

We investigated cytochrome P450 (P450)-catalyzed metabolism of the important cancer drugs paclitaxel and docetaxel in rat, pig, minipig, and human liver microsomes and cDNA-expressed P450 enzymes. In rat microsomes, paclitaxel was metabolized mainly to C3'-hydroxypaclitaxel (C3'-OHP) and to a lesser extent to C2-hydroxypaclitaxel (C2-OHP), di-hydroxypaclitaxel (di-OHP), and another unknown monohydroxylated paclitaxel. In pig and minipig microsomes, this unknown hydroxypaclitaxel was the main metabolite, whereas C3'-OHP was a minor product. In minipigs, C2-OHP was the next minor product. In human liver microsomes, 6 alpha-hydroxypaclitaxel (6 alpha-OHP) was the main metabolite, followed by C3'-OHP and C2-OHP. Among different cDNA-expressed human P450 enzymes (CYP1A2, 1B1, 2A6, 2C9, 2E1, and 3A4), only CYP3A4 enzyme formed C3'-OHP and C2-OHP. Docetaxel was metabolized in pig, minipig, rat, and human liver microsomes mainly to hydroxydocetaxel (OHDTX), whereas CYP3A-induced rat microsomes produced primarily diastereomeric hydroxyoxazolidinones. Human liver microsomes from 10 different individuals formed OHDTX at different rates correlated with CYP3A4 content. Troleandomycin as a selective inhibitor of CYP3A inhibited the formation of C3'-OHP, C2-OHP, and di-OHP, as well as the unknown OHP produced in rat, minipig, and pig microsomes. In human liver microsomes, troleandomycin inhibited C3'-OHP and C2-OHP formation, and a suitable inhibitor of human CYP2C8, fisetin, strongly inhibited the formation of 6 alpha-OHP, known to be catalyzed by human CYP2C8. In conclusion, the metabolism of docetaxel is the same in all four species, but metabolism of paclitaxel is different, and 6 alpha-OHP remains a uniquely human metabolite. Pigs and minipigs compared with each other formed the same metabolites of paclitaxel.

Publication types

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

MeSH terms

  • Adolescent
  • Adult
  • Animals
  • Antineoplastic Agents, Phytogenic / metabolism*
  • Cytochrome P-450 Enzyme System / metabolism*
  • Docetaxel
  • Enzyme Inhibitors / pharmacology
  • Flavonoids / pharmacology
  • Flavonols
  • Humans
  • In Vitro Techniques
  • Isoenzymes / metabolism
  • Kinetics
  • Male
  • Microsomes, Liver / enzymology*
  • Paclitaxel / antagonists & inhibitors
  • Paclitaxel / metabolism*
  • Rats
  • Rats, Wistar
  • Species Specificity
  • Swine
  • Swine, Miniature
  • Taxoids / metabolism*
  • Troleandomycin / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Enzyme Inhibitors
  • Flavonoids
  • Flavonols
  • Isoenzymes
  • Taxoids
  • Docetaxel
  • Cytochrome P-450 Enzyme System
  • Troleandomycin
  • fisetin
  • Paclitaxel