Discovery of an intravenous hepatoselective glucokinase activator for the treatment of inpatient hyperglycemia

Bioorg Med Chem Lett. 2013 Dec 15;23(24):6588-92. doi: 10.1016/j.bmcl.2013.10.057. Epub 2013 Nov 4.

Abstract

Glucokinase (hexokinase IV) continues to be a compelling target for the treatment of type 2 diabetes given the wealth of supporting human genetics data and numerous reports of robust clinical glucose lowering in patients treated with small molecule allosteric activators. Recent work has demonstrated the ability of hepatoselective activators to deliver glucose lowering efficacy with minimal risk of hypoglycemia. While orally administered agents require a considerable degree of passive permeability to promote suitable exposures, there is no such restriction on intravenously delivered drugs. Therefore, minimization of membrane diffusion in the context of an intravenously agent should ensure optimal hepatic targeting and therapeutic index. This work details the identification a hepatoselective GKA exhibiting the aforementioned properties.

Keywords: Allosteric; Diabetes; Glucokinase; Hepatoselective; OATP.

MeSH terms

  • Allosteric Regulation
  • Animals
  • Cells, Cultured
  • Diabetes Mellitus, Type 2 / drug therapy
  • Drug Evaluation, Preclinical
  • Enzyme Activators / chemistry*
  • Enzyme Activators / metabolism
  • Enzyme Activators / therapeutic use
  • Glucokinase / chemistry*
  • Glucokinase / metabolism
  • Hepatocytes / cytology
  • Hepatocytes / enzymology
  • Humans
  • Hypoglycemic Agents / chemistry*
  • Hypoglycemic Agents / metabolism
  • Hypoglycemic Agents / therapeutic use
  • Imidazoles / chemistry
  • Injections, Intravenous
  • Niacin / analogs & derivatives
  • Niacin / chemistry
  • Rats
  • Tissue Distribution

Substances

  • 6-(2-(4-(cyclobutanesulfonyl)-1H-imidazol-1-yl)-3-cyclopentylpropanamido)pyridine-3-carboxylic acid
  • Enzyme Activators
  • Hypoglycemic Agents
  • Imidazoles
  • Niacin
  • imidazole
  • Glucokinase