title: Gas chromatographic-mass spectrometric studies on the metabolic fate of ethotoin in man.
abstract: Unchanged ethotoin and 11 metabolic products of ethotoin were detected in the urine of subjects (2 men and 1 woman) receiving ethotoin. Nine of these products were identified by comparison of their retention times and mass spectra with those of authentic synthetic samples. Hydroxylation of the hydantoin ring at the 5-position produced 5-hydroxyethotoin and 5-hydroxy-5-phenylhydantoin. Aryl hydroxylation resulted in the formation of p-hydroxyethotoin, o-hydroxyethotoin, m-hydroxyethotoin, 3-methoxy-4-hydroxyethotoin, and 3,4-dihydroxyethotoin. Most of these were excreted as the glucuronide conjugate. A dihydrodiol of ethotoin and 3-ethyl-5-hydroxy-5-(4-hydroxyphenyl)hydantoin were isolated along with unchanged ethotoin and 5-phenylhydantoin. 2-Phenylhydantoic acid was also isolated and was shown to have the (R)(-)-configuration.
mesh_terms: D001711:Biotransformation; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006827:Hydantoins / Q000378:metabolism* / Q000652:urine; D006868:Hydrolysis
chemical_list: D006827:Hydantoins