Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

Bioorg Med Chem. 2005 Jun 2;13(12):4022-36. doi: 10.1016/j.bmc.2005.03.052. Epub 2005 Apr 25.

Abstract

Ca(2+) overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium-hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca(2+) overload, because NCX inhibitors can directly inhibit the influx of Ca(2+) into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reperfusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23 h) with an IC(50) value of 0.12 microM against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23 h are discussed.

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Calcium / metabolism
  • Calcium Channel Blockers / chemical synthesis*
  • Calcium Channel Blockers / pharmacology
  • Cytochrome P-450 Enzyme System / drug effects
  • Disease Models, Animal
  • Heart Failure / drug therapy
  • Humans
  • Inhibitory Concentration 50
  • Male
  • Myocardial Reperfusion Injury / drug therapy
  • Niacinamide / analogs & derivatives*
  • Niacinamide / chemical synthesis
  • Niacinamide / pharmacology
  • Pharmacokinetics
  • Rats
  • Rats, Inbred Strains
  • Sodium-Calcium Exchanger / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Calcium Channel Blockers
  • Sodium-Calcium Exchanger
  • Niacinamide
  • Cytochrome P-450 Enzyme System
  • Calcium