PMID: 8950223Oct 21, 1996Paper

Formation of mammalian metabolites of cyclobenzaprine by the fungus, Cunninghamella elegans

Chemico-biological Interactions
D ZhangC E Cerniglia

Abstract

The fungus, Cunninghamella elegans, was used as a microbial model of mammalian drug metabolism to biotransform a tricyclic antidepressant, cyclobenzaprine. Seventy-five percent of this drug at a concentration of 1 mM was metabolized within 72 h by C. elegans grown on Sabouraud dextrose broth. Milligram amounts of fungal metabolites were isolated by reversed-phase high performance liquid chromatography (HPLC) and their structures were characterized by 1H NMR spectroscopy, mass spectrometry, and UV spectroscopy analyses. The major fungal metabolites of cyclobenzaprine were 2-hydroxycyclobenzaprine (59%), N-desmethylcyclobenzaprine (21%), cyclobenzaprine trans-10,11-dihydrodiol (5%), N-desmethyl-2-hydroxy-cyclobenzaprine (3%), 3-hydroxycyclobenzaprine (3%), and cyclobenzaprine N-oxide (1%). These fungal metabolites were used as standards to investigate the metabolism of cyclobenzaprine by rat liver microsomes. Rat liver microsomes also biotransformed cyclobenzaprine to produce similar metabolites as the fungus. The isotope labeling of 2-hydroxycyclobenzaprine by 18O2 and the trans-configuration of the dihydrodiol suggested that these reactions were catalyzed by cytochrome P-450 monooxygenases in C. elegans. These results also demo...Continue Reading

References

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Sep 1, 1991·Medicinal Research Reviews·A M Clark, C D Hufford
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Citations

Apr 17, 2008·Applied Microbiology and Biotechnology·Su-Il KangHor-Gil Hur
Nov 10, 2009·Applied Biochemistry and Biotechnology·Keshetty Srisailam, Ciddi Veeresham
Aug 5, 2000·Applied and Environmental Microbiology·J D MoodyC E Cerniglia
Aug 30, 2001·Applied and Environmental Microbiology·C J ChaC E Cerniglia
Sep 9, 2008·Biotechnology Advances·Sepuri Asha, Maravajhala Vidyavathi
Mar 18, 2015·Journal of Pharmaceutical and Biomedical Analysis·Nayara Cristina Perez de AlbuquerqueAnderson Rodrigo Moraes de Oliveira
Dec 2, 2008·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·I PieperM Bertau
Jul 29, 1998·The Annals of Pharmacotherapy·E L MichaletsE D Van Tassel
Aug 24, 1999·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·B T DuhartC E Cerniglia
Oct 19, 2002·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Joanna D MoodyCarl E Cerniglia
Nov 11, 2005·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Donglu ZhangW Griffith Humphreys
Oct 6, 2017·Frontiers in Microbiology·Darío R Olicón-HernándezElisabet Aranda

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