Biotransformation of flumequine by the fungus Cunninghamella elegans |
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Authors: | Williams Anna J Deck Joanna Freeman James P Paul Chiarelli M Adjei Michael D Heinze Thomas M Sutherland John B |
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Institution: | Division of Microbiology, National Center for Toxicological Research, Food and Drug Administration, Jefferson, AR 72079, USA. |
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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. |
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