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Research Article

The Role of Flavin-Containing Monooxygenase (FMO) in the Metabolism of Tamoxifen and Other Tertiary Amines

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Pages 139-147 | Published online: 09 Oct 2008

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A.B. Sanchez-Spitman, J.J. Swen, V.O. Dezentje, D.J.A.R. Moes, H. Gelderblom & H.J. Guchelaar. (2019) Clinical pharmacokinetics and pharmacogenetics of tamoxifen and endoxifen. Expert Review of Clinical Pharmacology 12:6, pages 523-536.
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Jing Luo, Bowei Zhang, Likun Cui, Tong Liu & Yi Gu. (2019) Fmo1 Gene Expression Independently Predicts Favorable Recurrence-Free Survival of Classical Papillary Thyroid Cancer. Future Oncology 15:12, pages 1303-1311.
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Barbara Fedejko-Kap, Magdalena Niemira, Anna Radominska-Pandya & Zofia Mazerska. (2011) Flavin monooxygenases, FMO1 and FMO3, not cytochrome P450 isoenzymes, contribute to metabolism of anti-tumour triazoloacridinone, C-1305, in liver microsomes and HepG2 cells. Xenobiotica 41:12, pages 1044-1055.
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Elizabeth A Shephard & Ian R Phillips. (2010) The potential of knockout mouse lines in defining the role of flavin-containing monooxygenases in drug metabolism. Expert Opinion on Drug Metabolism & Toxicology 6:9, pages 1083-1094.
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Meike S Motika, Jun Zhang & John R Cashman. (2007) Flavin-containing monooxygenase 3 and human disease. Expert Opinion on Drug Metabolism & Toxicology 3:6, pages 831-845.
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Marta Gawryś-Kopczyńska, Mateusz Szudzik, Emilia Samborowska, Marek Konop, Dawid Chabowski, Maksymilian Onyszkiewicz & Marcin Ufnal. (2024) Spontaneously hypertensive rats exhibit increased liver flavin monooxygenase expression and elevated plasma TMAO levels compared to normotensive and Ang II-dependent hypertensive rats. Frontiers in Physiology 15.
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Sandy Che-Eun S. Lee, Andrea Hye An Pyo & Marianne Koritzinsky. (2023) Longitudinal dynamics of the tumor hypoxia response: From enzyme activity to biological phenotype. Science Advances 9:47.
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Longfei Wang, Hongchu Zha, Jing Huang & Lang Shi. (2023) Flavin containing monooxygenase 2 regulates renal tubular cell fibrosis and paracrine secretion via SMURF2 in AKI‑CKD transformation. International Journal of Molecular Medicine 52:5.
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Shiqi Zhang, Dong Yi, Guang-xun Li, Yun Deng, Xin Cui, Yin Tian & Zhuo Tang. (2023) Biomimetic Dynamic Kinetic Asymmetric N -Oxidation with H 2 O 2 and O 2 . ACS Catalysis 13:18, pages 11954-11962.
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Xumeng Gong, Dong Hou, Shengning Zhou, Jianan Tan, Guangyu Zhong, Bing Yang, Lang Xie, Fanghai Han & Lin Zhong. (2023) FMO family may serve as novel marker and potential therapeutic target for the peritoneal metastasis in gastric cancer. Frontiers in Oncology 13.
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Slobodan P. Rendić, Rachel D. Crouch & F. Peter Guengerich. (2022) Roles of selected non-P450 human oxidoreductase enzymes in protective and toxic effects of chemicals: review and compilation of reactions. Archives of Toxicology 96:8, pages 2145-2246.
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Hanna Cheropkina, Gianluca Catucci, Arianna Marucco, Ivana Fenoglio, Gianfranco Gilardi & Sheila J. Sadeghi. (2021) Human flavin-containing monooxygenase 1 and its long-sought hydroperoxyflavin intermediate. Biochemical Pharmacology 193, pages 114763.
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David E. Williams. (2021) Indoles Derived From Glucobrassicin: Cancer Chemoprevention by Indole-3-Carbinol and 3,3'-Diindolylmethane. Frontiers in Nutrition 8.
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Kong-Xiang Zhu, Pei-Yuan Song, He-Li, Mu-Peng Li, Yin-xiao Du, Qi-lin Ma, Li-Ming Peng & Xiao-Ping Chen. (2020) Association of FMO3 rs1736557 polymorphism with clopidogrel response in Chinese patients with coronary artery disease. European Journal of Clinical Pharmacology 77:3, pages 359-368.
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Stefania Bortolussi, Gianluca Catucci, Gianfranco Gilardi & Sheila J. Sadeghi. (2021) N- and S-oxygenation activity of truncated human flavin-containing monooxygenase 3 and its common polymorphic variants. Archives of Biochemistry and Biophysics 697, pages 108663.
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Gianluca Catucci, Gianfranco Gilardi & Sheila J. Sadeghi. (2020) Production of drug metabolites by human FMO3 in Escherichia coli. Microbial Cell Factories 19:1.
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G. Catucci, D. Aramini, S.J. Sadeghi & G. Gilardi. (2020) Ligand stabilization and effect on unfolding by polymorphism in human flavin-containing monooxygenase 3. International Journal of Biological Macromolecules 162, pages 1484-1493.
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Callum R. Nicoll, Gautier Bailleul, Filippo Fiorentini, María Laura Mascotti, Marco W. Fraaije & Andrea Mattevi. (2019) Ancestral-sequence reconstruction unveils the structural basis of function in mammalian FMOs. Nature Structural & Molecular Biology 27:1, pages 14-24.
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Gianluca Catucci, Stefania Bortolussi, Giulia Rampolla, Debora Cusumano, Gianfranco Gilardi & Sheila J. Sadeghi. (2018) Flavin‐Containing Monooxygenase 3 Polymorphic Variants Significantly Affect Clearance of Tamoxifen and Clomiphene. Basic & Clinical Pharmacology & Toxicology 123:6, pages 687-691.
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Barry C. Jones, Abhishek Srivastava, Nicola Colclough, Joanne Wilson, Venkatesh Pilla Reddy, Sara Amberntsson & Danxi Li. (2017) An Investigation into the Prediction of In Vivo Clearance for a Range of Flavin-containing Monooxygenase Substrates. Drug Metabolism and Disposition 45:10, pages 1060-1067.
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Kui-Jin Kim, Kye-Yoon Yoon, Hee-Do Hong & Boo-Yong Lee. (2015) Role of the Red Ginseng in Defense against the Environmental Heat Stress in Sprague Dawley Rats. Molecules 20:11, pages 20240-20253.
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Silvia Castrignanò, Gianfranco Gilardi & Sheila J. Sadeghi. (2015) Human Flavin-Containing Monooxygenase 3 on Graphene Oxide for Drug Metabolism Screening. Analytical Chemistry 87:5, pages 2974-2980.
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Nadine A. Binai, Gert Carra, Johannes Löwer, Roswitha Löwer & Silja Wessler. (2013) Differential gene expression in ERα-positive and ERα-negative breast cancer cells upon leptin stimulation. Endocrine 44:2, pages 496-503.
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Duygu Yeniceli, Xiaolan Deng, Erwin Adams, Dilek Dogrukol‐Ak & Ann Van Schepdael. (2012) Development of a CD‐MEKC method for investigating the metabolism of tamoxifen by flavin‐containing monooxygenases and the inhibitory effects of methimazole, nicotine and DMXAA. ELECTROPHORESIS 34:3, pages 463-470.
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Jennifer Gjerde, Sara Gandini, Aliana Guerrieri-Gonzaga, Line L. Haugan Moi, Valentina Aristarco, Gunnar Mellgren, Andrea DeCensi & Ernst A. Lien. (2012) Tissue distribution of 4-hydroxy-N-desmethyltamoxifen and tamoxifen-N-oxide. Breast Cancer Research and Treatment 134:2, pages 693-700.
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Hui Lin, Jing-Yuan Liu, Hai-Bo Wang, Abeer Ahmed Qaed Ahmed & Zhong-Liu Wu. (2011) Biocatalysis as an alternative for the production of chiral epoxides: A comparative review. Journal of Molecular Catalysis B: Enzymatic 72:3-4, pages 77-89.
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Bhupendra Singh, Nimee K. Bhat & Hari K. Bhat. (2011) Partial Inhibition of Estrogen-Induced Mammary Carcinogenesis in Rats by Tamoxifen: Balance between Oxidant Stress and Estrogen Responsiveness. PLoS ONE 6:9, pages e25125.
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Agnieszka Potega, Emilia Dabrowska, Magdalena Niemira, Agata Kot-Wasik, Sebastien Ronseaux, Colin J. Henderson, C. Roland Wolf & Zofia Mazerska. (2011) The Imidazoacridinone Antitumor Drug, C-1311, Is Metabolized by Flavin Monooxygenases but Not by Cytochrome P450s. Drug Metabolism and Disposition 39:8, pages 1423-1432.
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S.F. Teunissen, H. Rosing, M. Dominguez Seoane, L. Brunsveld, J.H.M. Schellens, A.H. Schinkel & J.H. Beijnen. (2011) Investigational study of tamoxifen phase I metabolites using chromatographic and spectroscopic analytical techniques. Journal of Pharmaceutical and Biomedical Analysis 55:3, pages 518-526.
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Annica Tevell Åberg, Helena Löfgren, Ulf Bondesson & Mikael Hedeland. (2010) Structural elucidation of N ‐oxidized clemastine metabolites by liquid chromatography/tandem mass spectrometry and the use of Cunninghamella elegans to facilitate drug metabolite identification . Rapid Communications in Mass Spectrometry 24:10, pages 1447-1456.
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Sheila J. SadeghiRita MeirinhosGianluca CatucciVikash R. DodhiaGiovanna Di NardoGianfranco Gilardi. (2009) Direct Electrochemistry of Drug Metabolizing Human Flavin-Containing Monooxygenase: Electrochemical Turnover of Benzydamine and Tamoxifen. Journal of the American Chemical Society 132:2, pages 458-459.
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