Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

Bioorg Med Chem. 2004 Oct 1;12(19):5213-24. doi: 10.1016/j.bmc.2004.06.027.

Abstract

A series of novel corticosteroid derivatives featuring C-17 furoate ester functionality have been synthesised. Profiling in vitro and in vivo has resulted in the identification of a compound with a longer duration of action and a lower oral side effect profile in rodents compared to budesonide.

MeSH terms

  • Androstenes / chemical synthesis*
  • Androstenes / pharmacokinetics
  • Androstenes / pharmacology
  • Animals
  • Biological Availability
  • Cell Line
  • Eosinophilia / drug therapy
  • Esters / chemical synthesis*
  • Esters / pharmacokinetics
  • Esters / pharmacology
  • Glucocorticoids / chemical synthesis*
  • Glucocorticoids / pharmacokinetics
  • Glucocorticoids / pharmacology
  • Humans
  • Macrophages / cytology
  • Organ Size / drug effects
  • Protein Binding
  • Rats
  • Receptors, Glucocorticoid / agonists*
  • Structure-Activity Relationship
  • Thymus Gland / drug effects
  • Tumor Necrosis Factor-alpha / analysis
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors

Substances

  • Androstenes
  • Esters
  • Glucocorticoids
  • Receptors, Glucocorticoid
  • Tumor Necrosis Factor-alpha