Discovery of novel, potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 (11beta-HSD1) exhibiting oral activity in an enzyme inhibition ex vivo model

J Med Chem. 2008 Jul 10;51(13):3953-60. doi: 10.1021/jm800310g. Epub 2008 Jun 14.

Abstract

We report the discovery of potent benzamide inhibitors of 11beta-hydroxysteroid dehydrogenase (11beta-HSD1). The optimization and correlation of in vitro and in vivo metabolic stability will be described. Through modifications to our initial lead 2, we discovered pyridyl compound 13. This compound has a favorable pharmacokinetic profile across three species and showed a dose-dependent decrease in adipose 11beta-HSD1 activity in a monkey ex vivo pharmacodynamic model.

MeSH terms

  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / antagonists & inhibitors*
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / chemistry
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1 / metabolism
  • Administration, Oral
  • Animals
  • Benzamides / administration & dosage*
  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Benzamides / metabolism
  • Cell Line
  • Crystallography, X-Ray
  • Dogs
  • Enzyme Inhibitors / administration & dosage*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Humans
  • Macaca fascicularis
  • Models, Animal
  • Models, Molecular
  • Molecular Structure
  • Rats
  • Structure-Activity Relationship

Substances

  • Benzamides
  • Enzyme Inhibitors
  • benzamide
  • 11-beta-Hydroxysteroid Dehydrogenase Type 1

Associated data

  • PDB/3D3E
  • PDB/3D4N