Preclinical pharmacokinetics of a novel HIV-1 attachment inhibitor BMS-378806 and prediction of its human pharmacokinetics

Biopharm Drug Dispos. 2005 Dec;26(9):387-402. doi: 10.1002/bdd.471.

Abstract

BMS-378806 is a prototype of novel HIV attachment inhibitors that block the gp120 and CD4 interaction, the first step of HIV-1 entry into cells. The present work investigated the pharmacokinetics of BMS-378806 in rats, dogs and monkeys and assessed its in vitro permeability and metabolism. BMS-378806 exhibited species-dependent oral bioavailability which was 19%-24% in rats and monkeys and 77% in dogs. In rats and monkeys, absorption was prolonged, with an apparent terminal half-life of 2.1 and 6.5 h, respectively. In rats, linear pharmacokinetics was observed between i.v. doses of 1 and 5 mg/kg and between p.o. doses of 5 and 25 mg/kg. The total body clearance was intermediate in rats and low in dogs and monkeys. The steady-state volume of distribution was moderate (0.4-0.6 l/kg), contributing to a short half-life (0.3-1.2 h) after i.v. dosing. Studies in bile-duct cannulated rats together with intraportal infusion studies revealed that the renal and hepatic clearance each accounted for 30% and 70% of the total elimination in rats, with the hepatic clearance largely being oxidative metabolism. In vitro, BMS-378806 was not highly protein bound (44%-73%). The Caco-2 permeability was modest (51 nm/s) and confounded by P-glycoprotein mediated efflux transport. Both of these may contribute to the low brain penetration observed in rats (brain/plasma AUC ratio=0.06). In human liver microsomes BMS-378806 was equally metabolized by cytochrome P450 1A2, 2D6 and 3A4 and did not inhibit major drug-metabolizing enzymes to a significant extent. Based on in vitro and animal data, a mechanistic approach that factors in absorption and first-pass metabolism was employed to predict the human oral bioavailability of BMS-378806 (ca 20%). This, together with the complex Dedrick plot method, was used to simulate human oral profiles and to project an efficacious dose. These study results offer a comprehensive assessment of the developability of BMS-378806 and provide important guidance to improving absorption and half-life of future compounds in the series. The current studies also demonstrate the value and approaches of understanding pharmacokinetic properties in the early stage of drug discovery.

MeSH terms

  • Animals
  • Anti-HIV Agents / administration & dosage
  • Anti-HIV Agents / pharmacokinetics*
  • Biological Availability
  • Caco-2 Cells
  • Cell Membrane Permeability / drug effects
  • Cytochrome P-450 Enzyme System / metabolism
  • Dogs
  • Drug Evaluation, Preclinical
  • Drug Stability
  • HIV Envelope Protein gp120 / metabolism
  • HIV-1 / drug effects*
  • HIV-1 / metabolism
  • Humans
  • Macaca fascicularis
  • Male
  • Metabolic Clearance Rate
  • Microsomes, Liver / metabolism
  • Piperazines / administration & dosage
  • Piperazines / pharmacokinetics*
  • Predictive Value of Tests
  • Protein Binding
  • Rats
  • Rats, Sprague-Dawley
  • Species Specificity

Substances

  • Anti-HIV Agents
  • BMS-378806
  • HIV Envelope Protein gp120
  • Piperazines
  • Cytochrome P-450 Enzyme System