Novel inhibitors of fatty acid amide hydrolase

Bioorg Med Chem Lett. 2007 Jun 15;17(12):3287-91. doi: 10.1016/j.bmcl.2007.04.009. Epub 2007 Apr 10.

Abstract

A class of bisarylimidazole derivatives are identified as potent inhibitors of the enzyme fatty acid amide hydrolase (FAAH). Compound 17 (IC(50)=2 nM) dose-dependently (0.1-10mg/kg, iv) potentiates the effects of exogenous anandamide (1 mg/kg, iv) in a rat thermal escape test (Hargreaves test), and shows robust antinociceptive activity in animal models of persistent (formalin test) and neuropathic (Chung model) pain. Compound 17 (20 mg/kg, iv) demonstrates activity in the formalin test that is comparable to morphine (3mg/kg, iv), and is dose-dependently inhibited by the CB1 antagonist SR141716A. In the Chung model, compound 17 shows antineuropathic effects similar to high-dose (100 mg/kg) gabapentin. FAAH inhibition shows potential utility for the clinical treatment of persistent and neuropathic pain.

Publication types

  • Comparative Study

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Amines / pharmacology
  • Analgesics / administration & dosage
  • Analgesics / pharmacology*
  • Animals
  • Cyclohexanecarboxylic Acids / pharmacology
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / administration & dosage
  • Enzyme Inhibitors / pharmacology*
  • Gabapentin
  • Humans
  • Imidazoles / chemistry
  • Imidazoles / pharmacology*
  • Mice
  • Mice, Knockout
  • Morphine / pharmacology
  • Pain Measurement / drug effects*
  • Pain Measurement / methods
  • Piperidines / antagonists & inhibitors
  • Piperidines / metabolism
  • Pyrazoles / antagonists & inhibitors
  • Pyrazoles / metabolism
  • Rats
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB1 / metabolism
  • Rimonabant
  • gamma-Aminobutyric Acid / pharmacology

Substances

  • Amines
  • Analgesics
  • Cyclohexanecarboxylic Acids
  • Enzyme Inhibitors
  • Imidazoles
  • Piperidines
  • Pyrazoles
  • Receptor, Cannabinoid, CB1
  • gamma-Aminobutyric Acid
  • Gabapentin
  • Morphine
  • Amidohydrolases
  • fatty-acid amide hydrolase
  • Rimonabant