Synthesis, biological evaluation, and pharmacokinetic study of novel liguzinediol prodrugs

Molecules. 2013 Apr 18;18(4):4561-72. doi: 10.3390/molecules18044561.

Abstract

Liguzinediol (LZDO) ester prodrugs 3-5 were synthesized and evaluated in vitro and in vivo for their potential use in prolonging the half-life of the parent drug LZDO (1a) in vivo. Prodrugs 3-5 were found to display a potent positive inotropic effect on the myocardium, without the risk of arrhythmia. Prodrugs 3-5 rapidly underwent enzymatic hydrolysis to release the parent compound LZDO in 1-3 h in rat liver microsomes and rat plasma. The half-life of the parent compound was prolonged after intragastric administration of prodrug 3, which was found to be a superior prodrug candidate for increasing myocardial contractility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Blood Pressure / drug effects
  • Drug Stability
  • Heart / drug effects
  • Male
  • Microsomes, Liver / metabolism
  • Myocardial Contraction / drug effects
  • Myocardium / metabolism
  • Prodrugs / chemistry*
  • Prodrugs / metabolism
  • Prodrugs / pharmacokinetics*
  • Pyrazines / chemistry*
  • Pyrazines / metabolism
  • Pyrazines / pharmacokinetics*
  • Rats

Substances

  • 2,5-dihydroxymethyl-3,6-dimethylpyrazine
  • Prodrugs
  • Pyrazines