Discovery of (2R)-2-(3-{3-[(4-Methoxyphenyl)carbonyl]-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl}phenoxy)butanoic acid (MK-0533): a novel selective peroxisome proliferator-activated receptor gamma modulator for the treatment of type 2 diabetes mellitus with a reduced potential to increase plasma and extracellular fluid volume

J Med Chem. 2009 Jul 9;52(13):3846-54. doi: 10.1021/jm900097m.

Abstract

Peroxisome proliferator-activated receptor gamma (PPARgamma) agonists are used to treat type 2 diabetes mellitus (T2DM). Widespread use of PPARgamma agonists has been prevented due to adverse effects including weight gain, edema, and increased risk of congestive heart failure. Selective PPARgamma modulators (SPPARgammaMs) have been identified that have antidiabetic efficacy and reduced toxicity in preclinical species. In comparison with PPARgamma full agonists, SPPARgammaM 6 (MK0533) displayed diminished maximal activity (partial agonism) in cell-based transcription activation assays and attenuated gene signatures in adipose tissue. Compound 6 exhibited comparable efficacy to rosiglitazone and pioglitazone in vivo. However, with regard to the induction of untoward events, 6 displayed no cardiac hypertrophy, attenuated increases in brown adipose tissue, minimal increases in plasma volume, and no increases in extracellular fluid volume in vivo. Further investigation of 6 is warranted to determine if the improvement in mechanism-based side effects observed in preclinical species will be recapitulated in humans.

MeSH terms

  • Animals
  • Blood Volume / drug effects
  • Body Fluids / drug effects
  • Diabetes Mellitus, Type 2 / drug therapy*
  • Dogs
  • Haplorhini
  • Humans
  • Hypoglycemic Agents / adverse effects
  • Hypoglycemic Agents / pharmacokinetics*
  • Hypoglycemic Agents / therapeutic use
  • Indoles / adverse effects
  • Indoles / pharmacokinetics*
  • Indoles / therapeutic use
  • PPAR gamma / agonists*
  • Pioglitazone
  • Rats
  • Rosiglitazone
  • Structure-Activity Relationship
  • Thiazolidinediones

Substances

  • Hypoglycemic Agents
  • Indoles
  • PPAR gamma
  • Thiazolidinediones
  • Rosiglitazone
  • Pioglitazone