Absorption of TAK-491, a new angiotensin II receptor antagonist, in animals

Xenobiotica. 2013 Feb;43(2):182-92. doi: 10.3109/00498254.2012.708797. Epub 2012 Aug 7.

Abstract

The absorption process in animals of TAK-491, designed as ester-based prodrug with medoxomil moiety, was evaluated. In the plasma of rats and dogs, TAK-536, the pharmacologically active metabolite, was present as the main component with hardly detectable concentrations of TAK-491 after oral administration of TAK-491. In the rat portal plasma, TAK-536 was also present as the main component with hardly detectable concentrations of TAK-491 after jejunal loop injection of TAK-491, suggesting TAK-491 was absorbed from small intestine and hydrolyzed almost completely during absorption. Caco-2 study indicated the permeability of TAK-491 was improved by prodrug modification and the compound could be mainly transferred as TAK-491. This is well consistent with the facts that the AUC and T(max) of TAK-536 after oral administration of TAK-491 were higher and shorter than those after oral administration of TAK-536 in dogs Hydrolysis of TAK-491 is observed not only by the intestinal and hepatic S9 fraction, but also by plasma and human serum albumin. However, medoxomil alcohol wasn't detected during the hydrolysis of TAK-491. These metabolic features of TAK-491 were similar to olmesartan medoxomil, suggesting the hydrolytic pathway and enzymes for TAK-491 when catalyzing to TAK-536 would be the same as olmesartan medoxomil.

Publication types

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

MeSH terms

  • Administration, Oral
  • Angiotensin II Type 1 Receptor Blockers / administration & dosage
  • Angiotensin II Type 1 Receptor Blockers / metabolism
  • Angiotensin II Type 1 Receptor Blockers / pharmacokinetics*
  • Animals
  • Benzimidazoles / administration & dosage
  • Benzimidazoles / metabolism
  • Benzimidazoles / pharmacokinetics*
  • Caco-2 Cells
  • Carbon Radioisotopes / blood
  • Cell Membrane Permeability
  • Dogs
  • Humans
  • Hydrolysis
  • Intestinal Absorption
  • Intestinal Mucosa / metabolism
  • Liver / metabolism
  • Male
  • Oxadiazoles / administration & dosage
  • Oxadiazoles / metabolism
  • Oxadiazoles / pharmacokinetics*
  • Rats
  • Rats, Wistar
  • Serum Albumin

Substances

  • Angiotensin II Type 1 Receptor Blockers
  • Benzimidazoles
  • Carbon Radioisotopes
  • Oxadiazoles
  • Serum Albumin
  • azilsartan
  • azilsartan medoxomil