Characterization of the cytochrome P450 enzymes involved in the in vitro metabolism of rosiglitazone

Br J Clin Pharmacol. 1999 Sep;48(3):424-32. doi: 10.1046/j.1365-2125.1999.00030.x.

Abstract

To identify the human cytochrome P450 enzyme(s) involved in the in vitro metabolism of rosiglitazone, a potential oral antidiabetic agent for the treatment of type 2 diabetes-mellitus. Method The specific P450 enzymes involved in the metabolism of rosiglitazone were determined by a combination of three approaches; multiple regression analysis of the rates of metabolism of rosiglitazone in human liver microsomes against selective P450 substrates, the effect of selective chemical inhibitors on rosiglitazone metabolism and the capability of expressed P450 enzymes to mediate the major metabolic routes of rosiglitazone metabolism. Result The major products of metabolism following incubation of rosiglitazone with human liver microsomes were para-hydroxy and N-desmethyl rosiglitazone. The rate of formation varied over 38-fold in the 47 human livers investigated and correlated with paclitaxel 6alpha-hydroxylation (P<0.001). Formation of these metabolites was inhibited significantly (>50%) by 13-cis retinoic acid, a CYP2C8 inhibitor, but not by furafylline, quinidine or ketoconazole. In addition, both metabolites were produced by microsomes derived from a cell line transfected with human CYP2C8 cDNA. There was some evidence for CYP2C9 playing a minor role in the metabolism of rosiglitazone. Sulphaphenazole caused limited inhibition (<30%) of both pathways in human liver microsomes and microsomes from cells transfected with CYP2C9 cDNA were able to mediate the metabolism of rosiglitazone, in particular the N-demethylation pathway, albeit at a much slower rate than CYP2C8. Rosiglitazone caused moderate inhibition of paclitaxel 6alpha-hydroxylase activity (CYP2C8; IC50=18 microm ), weak inhibition of tolbutamide hydroxylase activity (CYP2C9; IC50=50 microm ), but caused no marked inhibition of the other cytochrome P450 activities investigated (CYP1A2, 2A6, 2C9, 2C19, 2D6, 2E1, 3A and 4A). Conclusion CYP2C8 is primarily responsible for the hydroxylation and N-demethylation of rosiglitazone in human liver; with minor contributions from CYP2C9.

MeSH terms

  • Aryl Hydrocarbon Hydroxylases*
  • Cytochrome P-450 CYP1A2
  • Cytochrome P-450 CYP2C8
  • Cytochrome P-450 CYP2C9
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism*
  • DNA, Complementary / genetics
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Hypoglycemic Agents / metabolism
  • Kinetics
  • Microsomes, Liver / enzymology
  • Microsomes, Liver / metabolism*
  • Rosiglitazone
  • Steroid 16-alpha-Hydroxylase*
  • Steroid Hydroxylases / genetics
  • Steroid Hydroxylases / metabolism
  • Thiazoles / metabolism*
  • Thiazolidinediones*
  • Transfection
  • Tumor Cells, Cultured

Substances

  • DNA, Complementary
  • Enzyme Inhibitors
  • Hypoglycemic Agents
  • Thiazoles
  • Thiazolidinediones
  • Rosiglitazone
  • Cytochrome P-450 Enzyme System
  • Steroid Hydroxylases
  • CYP2C9 protein, human
  • Cytochrome P-450 CYP2C9
  • Aryl Hydrocarbon Hydroxylases
  • CYP1A2 protein, human
  • CYP2C8 protein, human
  • Cytochrome P-450 CYP1A2
  • Cytochrome P-450 CYP2C8
  • Steroid 16-alpha-Hydroxylase