title: Biotransformation of flumequine by the fungus Cunninghamella elegans.
abstract: The metabolism of the antibacterial fluoroquinolone drug flumequine by Cunninghamella elegans was investigated using cultures grown in Sabouraud dextrose broth with 308microM flumequine. The cultures were extracted with ethyl acetate; metabolites were separated by high-performance liquid chromatography and identified by mass spectrometry and proton nuclear magnetic resonance spectroscopy. Flumequine was transformed to two diastereomers of 7-hydroxyflumequine (23 and 43% of the total chromatographic peak area at 280nm) and 7-oxoflumequine (11% of the total peak area). This is the first time that the two 7-hydroxy diastereomers have been characterized structurally; the hydroxyflumequines are known to have less antimicrobial activity than flumequine.
authors.affiliation: Division of Microbiology, National Center for Toxicological Research, Food and Drug Administration, Jefferson, AR 72079, USA.
authors.forename: Anna J
authors.initials: AJ
authors.lastname: Williams
authors.forename: Joanna
authors.initials: J
authors.lastname: Deck
authors.forename: James P
authors.initials: JP
authors.lastname: Freeman
authors.forename: M
authors.initials: M
authors.lastname: Paul Chiarelli
authors.forename: Michael D
authors.initials: MD
authors.lastname: Adjei
authors.forename: Thomas M
authors.initials: TM
authors.lastname: Heinze
authors.forename: John B
authors.initials: JB
authors.lastname: Sutherland
mesh_terms: D001711:Biotransformation; D020093:Cunninghamella / Q000378:metabolism*; D024841:Fluoroquinolones / Q000378:metabolism*; D012988:Soil Microbiology
chemical_list: D024841:Fluoroquinolones; C012976:flumequine