Preclinical pharmacokinetics and in vitro metabolism of brivanib (BMS-540215), a potent VEGFR2 inhibitor and its alanine ester prodrug brivanib alaninate

Cancer Chemother Pharmacol. 2009 Dec;65(1):55-66. doi: 10.1007/s00280-009-1002-0. Epub 2009 Apr 26.

Abstract

Purpose: Brivanib alaninate is a prodrug of brivanib (BMS-540215), a potent oral VEGFR-2 inhibitor and is currently in development for the treatment of hepatocellular and colon carcinomas. In vitro and in vivo studies were conducted to characterize the preclinical pharmacokinetics and disposition of brivanib and brivanib alaninate, and antitumor efficacy in mice bearing human xenografts.

Methods: In vitro studies were conducted in liver and intestinal fractions, plasma and Caco-2 cells to assess the metabolic stability. Pharmacokinetics of brivanib were determined in preclinical species after administration of single intravenous or oral doses of both brivanib and brivanib alaninate. The antitumor efficacy was assessed at equimolar doses in nude mice bearing human tumor xenografts. Human efficacious dose was predicted based on projected human pharmacokinetic parameters and exposure at efficacious doses in the mouse efficacy models.

Results: In vitro and in vivo studies indicated that brivanib alaninate was efficiently converted to brivanib. Brivanib showed good brain penetration in rats consistent with its high intrinsic permeability and lack of active efflux in Caco-2 cells. The oral bioavailability of brivanib varied among species (22-88%) and showed dissolution rate-limited absorption even when combined with organic co-solvents. Administration of brivanib as brivanib alaninate allowed completely aqueous vehicles, and an improvement in the oral bioavailability (55-97%) was observed. The clearance of brivanib in humans is anticipated to be low to intermediate (hepatic extraction ratio < 0.7), while its volume of distribution is expected to be high. The minimum efficacious dose of brivanib alaninate was determined to be 60 mg/kg per day.

Conclusions: Brivanib alaninate is rapidly and efficiently converted to the parent, brivanib, as demonstrated both in vitro and in vivo and offers an excellent mode to deliver brivanib orally.

MeSH terms

  • Administration, Oral
  • Alanine / analogs & derivatives*
  • Alanine / pharmacokinetics
  • Alanine / pharmacology
  • Animals
  • Antineoplastic Agents / pharmacokinetics*
  • Antineoplastic Agents / pharmacology
  • Biological Availability
  • Brain / metabolism
  • Caco-2 Cells
  • Dogs
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Female
  • Humans
  • Injections, Intravenous
  • Macaca fascicularis
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Mice, Nude
  • Prodrugs
  • Pyrroles / pharmacokinetics*
  • Pyrroles / pharmacology
  • Rats
  • Solubility
  • Tissue Distribution
  • Triazines / pharmacokinetics*
  • Triazines / pharmacology
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Prodrugs
  • Pyrroles
  • Triazines
  • brivanib
  • Vascular Endothelial Growth Factor Receptor-2
  • Alanine