Synthesis of the metabolites of a free radical scavenger edaravone (MCI-186, Radicut).
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.
Watanabe
Kazutoshi
K
Research and Development Division, Mitsubishi Pharma Corporation, Yokohama, Japan. Watanabe.Kazutoshi@mb.m-pharma.co.jp
Taniguchi
Masao
M
Shinoda
Masaki
M
D000983:Antipyrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D000077553:Edaravone; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000378:metabolism; D005965:Glucuronates / Q000138:chemical synthesis*; D015394:Molecular Structure; D013431:Sulfates / Q000138:chemical synthesis*
D016166:Free Radical Scavengers; D005965:Glucuronates; D013431:Sulfates; D000077553:Edaravone; D000983:Antipyrine