1-(1-acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea (AR9281) as a potent, selective, and orally available soluble epoxide hydrolase inhibitor with efficacy in rodent models of hypertension and dysglycemia

Bioorg Med Chem Lett. 2011 Feb 1;21(3):983-8. doi: 10.1016/j.bmcl.2010.12.042. Epub 2010 Dec 13.

Abstract

1-(1-Acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea 14a (AR9281), a potent and selective soluble epoxide hydrolase inhibitor, was recently tested in a phase 2a clinical setting for its effectiveness in reducing blood pressure and improving insulin resistance in pre-diabetic patients. In a mouse model of diet induced obesity, AR9281 attenuated the enhanced glucose excursion following an intraperitoneal glucose tolerance test. AR9281 also attenuated the increase in blood pressure in angiotensin-II-induced hypertension in rats. These effects were dose-dependent and well correlated with inhibition of the sEH activity in whole blood, consistent with a role of sEH in the observed pharmacology in rodents.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adamantane / analogs & derivatives*
  • Adamantane / chemistry
  • Adamantane / pharmacokinetics
  • Adamantane / therapeutic use
  • Administration, Oral
  • Angiotensin II / pharmacology
  • Animals
  • Antihypertensive Agents / chemistry*
  • Antihypertensive Agents / pharmacokinetics
  • Antihypertensive Agents / therapeutic use
  • Blood Glucose / analysis
  • Disease Models, Animal
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / therapeutic use
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Epoxide Hydrolases / metabolism
  • Hypertension / chemically induced
  • Hypertension / drug therapy*
  • Insulin Resistance*
  • Mice
  • Obesity / drug therapy
  • Rats
  • Urea / analogs & derivatives*
  • Urea / chemistry
  • Urea / pharmacokinetics
  • Urea / therapeutic use

Substances

  • 1-(1-acetyl-piperidine-4-yl)-3-adamantan-1-yl-urea
  • Antihypertensive Agents
  • Blood Glucose
  • Enzyme Inhibitors
  • Angiotensin II
  • Urea
  • Epoxide Hydrolases
  • Adamantane