Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy

J Med Chem. 2014 Aug 28;57(16):7016-30. doi: 10.1021/jm500694p. Epub 2014 Aug 11.

Abstract

Diabetes is affecting the life of millions of people. A large proportion of diabetic patients suffer from severe complications such as neuropathic pain, and current treatments for these complications have deleterious side effects. Thus, alternate therapeutic strategies are needed. Recently, the elevation of epoxy-fatty acids through inhibition of soluble epoxide hydrolase (sEH) was shown to reduce diabetic neuropathic pain in rodents. In this report, we describe a series of newly synthesized sEH inhibitors with at least 5-fold higher potency and doubled residence time inside both the human and rodent sEH enzyme than previously reported inhibitors. These inhibitors also have better physical properties and optimized pharmacokinetic profiles. The optimized inhibitor selected from this new series displayed improved efficacy of almost 10-fold in relieving pain perception in diabetic neuropathic rats as compared to the approved drug, gabapentin, and previously published sEH inhibitors. Therefore, these new sEH inhibitors could be an attractive alternative to treat diabetic neuropathy in humans.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Administration, Oral
  • Amines / pharmacology
  • Analgesics / pharmacology
  • Animals
  • Biological Availability
  • Chemistry Techniques, Synthetic
  • Crystallography, X-Ray
  • Cyclohexanecarboxylic Acids / pharmacology
  • Diabetes Mellitus, Type 1 / complications
  • Diabetic Neuropathies / drug therapy*
  • Diabetic Neuropathies / metabolism
  • Drug Design
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Gabapentin
  • Humans
  • Male
  • Mice
  • Molecular Targeted Therapy
  • Neuralgia / drug therapy
  • Rats, Sprague-Dawley
  • Solubility
  • Structure-Activity Relationship
  • Time Factors
  • gamma-Aminobutyric Acid / pharmacology

Substances

  • Amines
  • Analgesics
  • Cyclohexanecarboxylic Acids
  • Enzyme Inhibitors
  • gamma-Aminobutyric Acid
  • Gabapentin
  • Epoxide Hydrolases

Associated data

  • PDB/4OCZ
  • PDB/4OD0