Discovery of potent, orally-active, and muscle-selective androgen receptor modulators based on an N-aryl-hydroxybicyclohydantoin scaffold

J Med Chem. 2006 Dec 28;49(26):7596-9. doi: 10.1021/jm061101w.

Abstract

A novel, N-aryl-bicyclohydantoin selective androgen receptor modulator scaffold was discovered through structure-guided modifications of androgen receptor antagonists. A prototype compound (7R,7aS)-10b from this series is a potent and highly tissue-selective agonist of the androgen receptor. After oral dosing in a rat atrophied levator ani muscle model, (7R,7aS)-10b demonstrated efficacy at restoring levator ani muscle mass to that of intact controls and exhibited >50-fold selectivity for muscle over prostate.

MeSH terms

  • Administration, Oral
  • Animals
  • Breast Neoplasms / drug therapy
  • Bridged-Ring Compounds / chemical synthesis
  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / pharmacology*
  • Cells, Cultured
  • Dihydrotestosterone / pharmacology
  • Humans
  • Hydantoins / administration & dosage
  • Hydantoins / chemical synthesis
  • Hydantoins / chemistry
  • Hydantoins / pharmacology*
  • Luciferases / metabolism
  • Male
  • Mice
  • Muscle, Skeletal / drug effects*
  • Muscle, Skeletal / growth & development
  • Muscular Atrophy / drug therapy*
  • Myoblasts / drug effects
  • Rats
  • Receptors, Androgen / metabolism*
  • Transcriptional Activation

Substances

  • Bridged-Ring Compounds
  • Hydantoins
  • Receptors, Androgen
  • Dihydrotestosterone
  • Luciferases

Associated data

  • PDB/2IHQ