Identification of several human urinary metabolites of 6-benzoyl benzoxazolinone by gas chromatography/mass spectrometry.
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.
Bastide
M
M
Groupe de recherches en biodynamique du médicament, Faculté de pharmacie de Clermont-Ferrand, France.
Chabard
J L
JL
Lartigue
C
C
Bargnoux
H
H
Petit
J
J
Berger
J A
JA
Mansour
H A
HA
Lesieur
D
D
Buch
N
N
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
D000700:Analgesics; D001583:Benzoxazoles; D010080:Oxazoles; D023303:Oxazolidinones; C043851:6-benzoyl benzoxazolinone