Alkoxycarbonyloxyethyl ester prodrugs of FR900098 with improved in vivo antimalarial activity

Arch Pharm (Weinheim). 2005 Jul;338(7):305-14. doi: 10.1002/ardp.200500976.

Abstract

FR900098 represents a derivative of the new antimalarial drug fosmidomycin with enhanced activity. The mechanism of action is the inhibition of the 1-desoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase, an essential enzyme of the mevalonate independent pathway of isoprenoid biosynthesis. Prodrugs with increased oral activity in mice infected with the rodent malaria parasite Plasmodium vinckei were obtained by masking the phosphonate moiety of FR900098 as alkoxycarbonyloxyethyl esters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Aldose-Ketose Isomerases / antagonists & inhibitors
  • Aldose-Ketose Isomerases / metabolism
  • Animals
  • Antimalarials / chemical synthesis
  • Antimalarials / pharmacokinetics
  • Antimalarials / therapeutic use*
  • Biological Availability
  • Dose-Response Relationship, Drug
  • Fosfomycin / analogs & derivatives*
  • Fosfomycin / blood
  • Fosfomycin / chemical synthesis
  • Fosfomycin / pharmacokinetics
  • Fosfomycin / therapeutic use
  • Malaria / parasitology
  • Malaria / prevention & control*
  • Mice
  • Mice, Inbred BALB C
  • Multienzyme Complexes / antagonists & inhibitors
  • Multienzyme Complexes / metabolism
  • Oxidoreductases / antagonists & inhibitors
  • Oxidoreductases / metabolism
  • Plasmodium / drug effects
  • Prodrugs / chemical synthesis
  • Prodrugs / pharmacokinetics
  • Prodrugs / therapeutic use*
  • Quantitative Structure-Activity Relationship

Substances

  • Antimalarials
  • Multienzyme Complexes
  • Prodrugs
  • Fosfomycin
  • fosmidomycin
  • 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid
  • Oxidoreductases
  • 1-deoxy-D-xylulose 5-phosphate reductoisomerase
  • Aldose-Ketose Isomerases