Pharmacokinetic characterization of 2-(3-benzoyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-2-yl-1-phenylethanone, a novel 11β-hydroxysteroid dehydrogenase type 1 inhibitor in rats

Arch Pharm Res. 2016 Apr;39(4):492-498. doi: 10.1007/s12272-015-0702-8. Epub 2016 Jan 18.

Abstract

11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) is associated with metabolic syndromes such as type 2 diabetes mellitus and obesity. A new 11β-HSD1 inhibitor known as 2-(3-benzoyl)-4-hydroxy-1, 1-dioxo-2H-1, 2-benzothiazine-2-yl-1-phenylethanone (KR-66344) is being developed as a therapeutic agent for these metabolic diseases. The purpose of this study was to characterize the pharmacokinetics of KR-66344 to support further preclinical development. KR-66344 showed high liver microsomal stability with T1/2 values >3 h and high permeability with apparent permeability coefficients of 15.2-24.2 × 10(-6) cm/s in Caco-2 cell monolayers. KR-66344 was also strongly bound to plasma proteins (>98%). After intravenous dosing, KR-66344 exhibited low systemic clearance (0.27-0.37 L/h/kg) and a low to moderate volume of distribution at steady state (0.79-0.8 L/kg). The bioavailability and terminal half-lives of KR-66344 following oral administration were 25% and 1.7-3.3 h, respectively. In addition, KR-66344 showed dose-independent pharmacokinetics at 0.5-10 mg/kg in intravenous and oral pharmacokinetic studies.

Keywords: 11β-hydroxysteroid dehydrogenase type 1; Caco-2 cell permeability; Metabolic stability; Pharmacokinetics; Plasma protein binding.

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • Administration, Oral
  • Animals
  • Biological Availability
  • Blood Proteins / metabolism
  • Caco-2 Cells
  • Cell Membrane Permeability
  • Cyclic S-Oxides / administration & dosage
  • Cyclic S-Oxides / chemistry
  • Cyclic S-Oxides / pharmacokinetics*
  • Cyclic S-Oxides / pharmacology
  • Dogs
  • Drug Evaluation, Preclinical
  • Enzyme Inhibitors / administration & dosage
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacokinetics*
  • Enzyme Inhibitors / pharmacology
  • Half-Life
  • Humans
  • Hypoglycemic Agents / administration & dosage
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacokinetics*
  • Hypoglycemic Agents / pharmacology
  • Injections, Intravenous
  • Male
  • Mice
  • Microsomes, Liver / metabolism*
  • Molecular Structure
  • Protein Binding
  • Rats, Sprague-Dawley
  • Solubility
  • Thiazines / administration & dosage
  • Thiazines / chemistry
  • Thiazines / pharmacokinetics*
  • Thiazines / pharmacology
  • Tissue Distribution

Substances

  • 2-(3-benzoyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-2-yl-1-phenylethanone
  • Blood Proteins
  • Cyclic S-Oxides
  • Enzyme Inhibitors
  • Hypoglycemic Agents
  • Thiazines
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1