title: Identification of several human urinary metabolites of 6-benzoyl benzoxazolinone by gas chromatography/mass spectrometry.
abstract: The biotransformation of 6-benzoyl benzoxazolinone (6-BB), a non-narcotic peripheral analgesic, was studied in eight healthy volunteers after oral administration of a single dose of 1 g. Urinary metabolites were extracted either with ethyl acetate at different pH values or by percolating at pH 5 through Amberlite XAD 2 ion-exchange resin. Eluates were concentrated under vacuum, purified by thin-layer chromatography and analysed by gas chromatography/mass spectrometry or direct insertion probe mass spectrometry. Metabolites were identified with reference to the mass spectra of various synthesized compounds assumed to be metabolites of 6-BB, as N-methylated or monohydroxylated compounds. Another metabolic pathway was cleavage of the benzoxazolinone heterocycle giving 2-amino-5-benzoyl phenol after hydrolysis and decarboxylation. N-methyl, N-acetyl and hydroxylated metabolites having an amino-5-benzoyl phenol structure were also found.
authors.affiliation: Groupe de recherches en biodynamique du médicament, Faculté de pharmacie de Clermont-Ferrand, France.
authors.forename: M
authors.initials: M
authors.lastname: Bastide
authors.forename: J L
authors.initials: JL
authors.lastname: Chabard
authors.forename: C
authors.initials: C
authors.lastname: Lartigue
authors.forename: H
authors.initials: H
authors.lastname: Bargnoux
authors.forename: J
authors.initials: J
authors.lastname: Petit
authors.forename: J A
authors.initials: JA
authors.lastname: Berger
authors.forename: H A
authors.initials: HA
authors.lastname: Mansour
authors.forename: D
authors.initials: D
authors.lastname: Lesieur
authors.forename: N
authors.initials: N
authors.lastname: Buch
mesh_terms: D000328:Adult; D000700:Analgesics / Q000652:urine*; D001583:Benzoxazoles; D001711:Biotransformation; D002852:Chromatography, Ion Exchange; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D010080:Oxazoles / Q000652:urine*; D023303:Oxazolidinones
chemical_list: D000700:Analgesics; D001583:Benzoxazoles; D010080:Oxazoles; D023303:Oxazolidinones; C043851:6-benzoyl benzoxazolinone