CHARACTERIZATION OF MEPHENYTOIN METABOLITES IN HUMAN-URINE BY GAS-CHROMATOGRAPHY AND MASS-SPECTROMETRY

  • 1 January 1979
    • journal article
    • research article
    • Vol. 7  (3) , 138-144
Abstract
Metabolities of [the anticonvulsant drug] mephenytoin (5-ethyl-3-methyl-5-phenylhydantoin) were characterized in human urine after chromatography on XAD-2 resin, permethylation and combined gas chromatography and mass spectrometry. Glucuronide metabolites(4) previously unidentified in man were characterized as their permethylated derivatives by chemical-ionization and electron-impact mass spectrometry. The metabolities included 5-ethyl-5-(hydroxyphenyl)-3-methylhydantoin O-glucuronide, 5-hydroxyethyl-3-methyl-5-phenylhydantoin O-glucuronide, 5-ethyl-5-(hydroxymethoxyphenyl)-3-methylhydantoin O-glucuronide and a metabolite tentatively identified as 5-ethyl-5-phenylhydantoin N3-glucuronide in which both N-demethylation and glucuronide conjugation of the hydantoin ring have occurred. Mephenytoin, N-demethylmephenytoin, 5-ethyl-5-(hydroxyphenyl)-3-methylhydantoin and 5-ethyl-5-(hydroxymethoxyphenyl)-3-methylhydantoin were characterized in extracts of enzymatically hydrolyzed urine.