Synthesis of the metabolites of a free radical scavenger edaravone (MCI-186, Radicut)

Redox Rep. 2003;8(3):157-61. doi: 10.1179/135100003225001539.

Abstract

Two metabolites of a free radical scavenger, edaravone, were synthesized. Edaravone glucuronate was synthesized by glycosylation of a glucuronic acid precursor using silver (I) trifluoromethane-sulfonate with edaravone. Edaravone sulfate was synthesized by sulfonylation of edaravone using a sulfur trioxide-pyridine complex. The two synthesized metabolites were identical to isolated metabolites. X-ray analysis identified edaravone glucuronate as beta-O-glucuronate, although there were three possible edaravone glucuronate tautomers.

MeSH terms

  • Antipyrine / analogs & derivatives*
  • Antipyrine / chemical synthesis*
  • Antipyrine / metabolism
  • Edaravone
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / metabolism
  • Glucuronates / chemical synthesis*
  • Molecular Structure
  • Sulfates / chemical synthesis*

Substances

  • Free Radical Scavengers
  • Glucuronates
  • Sulfates
  • Edaravone
  • Antipyrine