Identification of a Selective, Non-Prostanoid EP2 Receptor Agonist for the Treatment of Glaucoma: Omidenepag and its Prodrug Omidenepag Isopropyl

J Med Chem. 2018 Aug 9;61(15):6869-6891. doi: 10.1021/acs.jmedchem.8b00808. Epub 2018 Jul 30.

Abstract

EP2 receptor agonists are expected to be effective ocular hypotensive agents; however, it has been suggested that agonism to other EP receptor subtypes may lead to undesirable effects. Through medicinal chemistry efforts, we identified a scaffold bearing a (pyridin-2-ylamino)acetic acid moiety as a promising EP2-selective receptor agonist. (6-((4-(Pyrazol-1-yl)benzyl)(pyridin-3-ylsulfonyl)aminomethyl)pyridin-2-ylamino)acetic acid 13ax (omidenepag, OMD) exerted potent and selective activity toward the human EP2 receptor (h-EP2). Low doses of omidenepag isopropyl (OMDI), a prodrug of 13ax, lowered intraocular pressure (IOP) in ocular normotensive monkeys. OMDI was selected as a clinical candidate for the treatment of glaucoma.

MeSH terms

  • Acetates / chemistry
  • Acetates / metabolism*
  • Acetates / pharmacology*
  • Acetates / therapeutic use
  • Animals
  • Drug Discovery
  • Glaucoma / drug therapy*
  • Macaca fascicularis
  • Prodrugs / metabolism*
  • Pyridines / chemistry
  • Pyridines / metabolism*
  • Pyridines / pharmacology*
  • Pyridines / therapeutic use
  • Receptors, Prostaglandin E, EP2 Subtype / agonists*
  • Structure-Activity Relationship

Substances

  • Acetates
  • Prodrugs
  • Pyridines
  • Receptors, Prostaglandin E, EP2 Subtype