An evaluation of a C-glucuronide as a liver targeting group: conjugate of a glucocorticoid antagonist

Bioorg Med Chem Lett. 2003 Jul 21;13(14):2307-10. doi: 10.1016/s0960-894x(03)00431-1.

Abstract

A beta-C-glucuronide conjugate of the glucocorticoid receptor antagonist, Mifepristone 1, was prepared which maintained binding affinity, had modest in vitro activity, and was metabolically more stable than the parent. Pharmacokinetic studies suggest that the conjugate is recognized by the liver like O-glucuronides and may undergo a portion of the enterohepatic recirculation loop.

MeSH terms

  • Administration, Oral
  • Alkaline Phosphatase / antagonists & inhibitors
  • Animals
  • Binding, Competitive / drug effects
  • Dexamethasone / pharmacokinetics
  • Drug Delivery Systems*
  • Enterohepatic Circulation
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Glucocorticoids / pharmacokinetics
  • Glucuronides / metabolism*
  • Glucuronides / pharmacokinetics
  • Hormone Antagonists / administration & dosage*
  • Hormone Antagonists / pharmacokinetics
  • Hormone Antagonists / pharmacology*
  • Humans
  • In Vitro Techniques
  • Indicators and Reagents
  • Injections, Intravenous
  • Liver / drug effects*
  • Microsomes, Liver / metabolism
  • Mifepristone / administration & dosage*
  • Mifepristone / pharmacokinetics
  • Mifepristone / pharmacology*
  • Quaternary Ammonium Compounds
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Glucocorticoid / antagonists & inhibitors*
  • Tyrosine Transaminase / antagonists & inhibitors

Substances

  • Enzyme Inhibitors
  • Glucocorticoids
  • Glucuronides
  • Hormone Antagonists
  • Indicators and Reagents
  • Quaternary Ammonium Compounds
  • Receptors, Glucocorticoid
  • Mifepristone
  • Dexamethasone
  • tetrabutylammonium
  • Tyrosine Transaminase
  • Alkaline Phosphatase