Investigational small-molecule drug selectively suppresses constitutive CYP2B6 activity at the gene transcription level: physiologically based pharmacokinetic model assessment of clinical drug interaction risk

Drug Metab Dispos. 2014 Jun;42(6):1008-15. doi: 10.1124/dmd.114.057018. Epub 2014 Mar 21.

Abstract

The glycogen synthase kinase-3 inhibitor LY2090314 specifically impaired CYP2B6 activity during in vitro evaluation of cytochrome P450 (P450) enzyme induction in human hepatocytes. CYP2B6 catalytic activity was significantly decreased following 3-day incubation with 0.1-10 μM LY2090314, on average by 64.3% ± 5.0% at 10 μM. These levels of LY2090314 exposure were not cytotoxic to hepatocytes and did not reduce CYP1A2 and CYP3A activities. LY2090314 was not a time-dependent CYP2B6 inhibitor, did not otherwise inhibit enzyme activity at concentrations ≤10 μM, and was not metabolized by CYP2B6. Thus, mechanism-based inactivation or other direct interaction with the enzyme could not explain the observed reduction in CYP2B6 activity. Instead, LY2090314 significantly reduced CYP2B6 mRNA levels (Imax = 61.9% ± 1.4%; IC50 = 0.049 ± 0.043 μM), which were significantly correlated with catalytic activity (r(2) = 0.87, slope = 0.77; Imax = 57.0% ± 10.8%, IC50 = 0.057 ± 0.027 μM). Direct inhibition of constitutive androstane receptor by LY2090314 is conceptually consistent with the observed CYP2B6 transcriptional suppression (Imax = 100.0% ± 10.8% and 57.1% ± 2.4%; IC50 = 2.5 ± 1.2 and 2.1 ± 0.4 μM for isoforms 1 and 3, respectively) and may be sufficiently extensive to overcome the weak but potent activation of pregnane X receptor by ≤10 μM LY2090314 (19.3% ± 2.2% of maximal rifampin response, apparent EC50 = 1.2 ± 1.1 nM). The clinical relevance of these findings was evaluated through physiologically based pharmacokinetic model simulations. CYP2B6 suppression by LY2090314 is not expected clinically, with a projected <1% decrease in hepatic enzyme activity and <1% decrease in hydroxybupropion exposure following bupropion coadministration. However, simulations showed that observed CYP2B6 suppression could be clinically relevant for a drug with different pharmacokinetic properties from LY2090314.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bupropion / pharmacology
  • Cell Line, Tumor
  • Cytochrome P-450 CYP2B6 / biosynthesis*
  • Cytochrome P-450 CYP2B6 / genetics*
  • Cytochrome P-450 CYP2D6 Inhibitors / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Interactions / physiology
  • Drugs, Investigational / chemistry
  • Drugs, Investigational / pharmacology*
  • Female
  • Hepatocytes / drug effects
  • Hepatocytes / enzymology
  • Heterocyclic Compounds, 3-Ring / pharmacology
  • Humans
  • Male
  • Maleimides / pharmacology
  • Transcription, Genetic / drug effects*
  • Transcription, Genetic / physiology*

Substances

  • 3-(9-fluoro-2-(piperidin-1-ylcarbonyl)-1,2,3,4-tetrahydro(1,4)diazepino(6,7,1-hi)indol-7-yl)-4-imidazo(1,2-a)pyridin-3-yl-1H-pyrrole-2,5-dione
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Drugs, Investigational
  • Heterocyclic Compounds, 3-Ring
  • Maleimides
  • Bupropion
  • Cytochrome P-450 CYP2B6