2-Chloro-4-[[(1R,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile: A Transdermal Selective Androgen Receptor Modulator (SARM) for Muscle Atrophy

J Med Chem. 2016 Jan 28;59(2):750-5. doi: 10.1021/acs.jmedchem.5b01168. Epub 2016 Jan 7.

Abstract

A transdermal SARM has a potential to have therapeutic benefit through anabolic activity in muscle while sparing undesired effects of benign prostate hyperplasia (BPH) and liver-mediated decrease in HDL-C. 2-Chloro-4-[(2-hydroxy-2-methyl-cyclopentyl)amino]-3-methyl-benzonitrile 6 showed the desired muscle and prostate effects in a preclinical ORX rat model. Compound 6 had minimal effect on HDL-C levels in cynomolgus monkeys and showed human cadaver skin permeability, thus making it an effective tool for proof-of-concept studies in a clinical setting.

Publication types

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

MeSH terms

  • Administration, Cutaneous
  • Anabolic Agents / administration & dosage
  • Anabolic Agents / chemical synthesis
  • Anabolic Agents / therapeutic use*
  • Androgen Antagonists / administration & dosage
  • Androgen Antagonists / chemical synthesis
  • Androgen Antagonists / therapeutic use*
  • Aniline Compounds / administration & dosage
  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / therapeutic use*
  • Animals
  • Cholesterol, HDL / metabolism
  • Humans
  • Hypercholesterolemia / chemically induced
  • In Vitro Techniques
  • Liver / drug effects
  • Liver / metabolism
  • Macaca fascicularis
  • Male
  • Models, Molecular
  • Muscular Atrophy / drug therapy*
  • Nitriles / administration & dosage
  • Nitriles / chemical synthesis
  • Nitriles / therapeutic use*
  • Orchiectomy
  • Prostatic Hyperplasia / chemically induced
  • Rats
  • Skin Absorption
  • Structure-Activity Relationship

Substances

  • 2-chloro-4-((2-hydroxy-2-methylcyclopentyl)amino)-3-methylbenzonitrile
  • Anabolic Agents
  • Androgen Antagonists
  • Aniline Compounds
  • Cholesterol, HDL
  • Nitriles