(3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(1-methyl-1h-1,2,4-triazol-5-yl)amino)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoic acid (BMS-644950): a rationally designed orally efficacious 3-hydroxy-3-methylglutaryl coenzyme-a reductase inhibitor with reduced myotoxicity potential

J Med Chem. 2008 May 8;51(9):2722-33. doi: 10.1021/jm800001n. Epub 2008 Apr 15.

Abstract

3-hydroxy-3-methylglutaryl coenzyme-A reductase (HMGR) inhibitors, more commonly known as statins, represent the gold standard in treating hypercholesterolemia. Although statins are regarded as generally safe, they are known to cause myopathy and, in rare cases, rhabdomyolysis. Statin-dependent effects on plasma lipids are mediated through the inhibition of HMGR in the hepatocyte, whereas evidence suggests that myotoxicity is due to inhibition of HMGR within the myocyte. Thus, an inhibitor with increased selectivity for hepatocytes could potentially result in an improved therapeutic window. Implementation of a strategy that focused on in vitro potency, compound polarity, cell selectivity, and oral absorption, followed by extensive efficacy and safety modeling in guinea pig and rat, resulted in the identification of compound 1b (BMS-644950). Using this discovery pathway, we compared 1b to other marketed statins to demonstrate its outstanding efficacy and safety profile. With the potential to generate an excellent therapeutic window, 1b was advanced into clinical development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Chemical and Drug Induced Liver Injury / etiology
  • Cholesterol / biosynthesis
  • Cholesterol / blood
  • Crystallography, X-Ray
  • Dogs
  • Female
  • Guinea Pigs
  • Haplorhini
  • Humans
  • Hydroxymethylglutaryl CoA Reductases / chemistry
  • Hydroxymethylglutaryl CoA Reductases / metabolism*
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / chemical synthesis*
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / pharmacology
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / toxicity
  • In Vitro Techniques
  • Liver / drug effects
  • Liver / metabolism
  • Models, Molecular
  • Muscle Cells / cytology
  • Muscle Cells / drug effects
  • Muscle Cells / metabolism
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology
  • Pyrimidines / toxicity
  • Rats
  • Rats, Sprague-Dawley
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology
  • Triazoles / toxicity

Substances

  • 7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(1-methyl-1H-1,2,4-triazol-5-yl)amino)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoic acid
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • Pyrimidines
  • Triazoles
  • Cholesterol
  • Hydroxymethylglutaryl CoA Reductases