Synthesis and pharmacological activity of a potent inhibitor of the biosynthesis of the endocannabinoid 2-arachidonoylglycerol

ChemMedChem. 2009 Jun;4(6):946-50. doi: 10.1002/cmdc.200800442.

Abstract

Biosynthesis Inhibition: O-5596, a new inhibitor of the biosynthesis of the endocannabinoid, 2-arachidonoylglycerol, was synthesized and found to be potent (IC(50)=100 nM) and selective versus other proteins and enzymes of the endocannabinoid system in vitro and active in vivo at reducing food intake in mice.

Publication types

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

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Alkenes / pharmacology*
  • Animals
  • Arachidonic Acids / biosynthesis*
  • Arachidonic Acids / chemistry
  • Cell Line
  • Drug Stability
  • Eating / drug effects
  • Endocannabinoids
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glycerides / biosynthesis*
  • Glycerides / chemistry
  • Humans
  • Lipoprotein Lipase / antagonists & inhibitors
  • Lipoprotein Lipase / metabolism
  • Mice
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / pharmacology*
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB2 / metabolism

Substances

  • Alkenes
  • Arachidonic Acids
  • Endocannabinoids
  • Enzyme Inhibitors
  • Glycerides
  • O-5596
  • Organophosphorus Compounds
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
  • glyceryl 2-arachidonate
  • DAGLA protein, human
  • Lipoprotein Lipase