The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines

scientific article

The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines is …
instance of (P31):
review articleQ7318358
scholarly articleQ13442814

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P356DOI10.1080/03602530600569919
P698PubMed publication ID16684653

P2093author name stringDavid E Williams
Sharon K Krueger
Ronald N Hines
Jonathan E Vandyke
P2860cites workThe flavin-containing monooxygenase 2 gene (FMO2) of humans, but not of other primates, encodes a truncated, nonfunctional proteinQ22004271
Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolismQ22251223
Human flavin-containing monooxygenase form 2 S-oxygenation: sulfenic acid formation from thioureas and oxidation of glutathioneQ24293146
Haplotype and functional analysis of four flavin-containing monooxygenase isoform 2 (FMO2) polymorphisms in HispanicsQ24539077
Genetic variability at the human FMO1 locus: significance of a basal promoter yin yang 1 element polymorphism (FMO1*6)Q28182512
Identification of novel variants of the flavin-containing monooxygenase gene family in African AmericansQ28203039
Human hepatic flavin-containing monooxygenases 1 (FMO1) and 3 (FMO3) developmental expressionQ28216584
Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1'-oxideQ28250108
The mammalian flavin-containing monooxygenases: molecular characterization and regulation of expressionQ28250605
The molecular biology of the flavin-containing monooxygenases of manQ28300051
Phenotypes of flavin-containing monooxygenase activity determined by ranitidine N-oxidation are positively correlated with genotypes of linked FM03 gene mutations in a Korean populationQ28374623
Formation of tamoxifen-DNA adducts via O-sulfonation, not O-acetylation, of alpha-hydroxytamoxifen in rat and human liversQ28573539
Alpha-hydroxylation of tamoxifen and toremifene by human and rat cytochrome P450 3A subfamily enzymesQ28576392
Identification of human CYP forms involved in the activation of tamoxifen and irreversible binding to DNA.Q33389761
The tamoxifen dilemmaQ33671066
Trimethylaminuria and a human FMO3 mutation databaseQ34225073
Study on the organoleptic intensity scale for measuring oral malodor.Q34285698
Structural and catalytic properties of the mammalian flavin-containing monooxygenaseQ34311922
Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6.Q34322613
The ontogeny of human drug-metabolizing enzymes: phase I oxidative enzymesQ34502898
Human flavin-containing monooxygenase (form 3): polymorphisms and variations in chemical metabolismQ34673357
An overview of the mechanism, substrate specificities, and structure of FMOsQ34818980
Genetic polymorphisms of flavin-containing monooxygenase (FMO).Q34819029
Interindividual differences of human flavin-containing monooxygenase 3: genetic polymorphisms and functional variationQ34849013
Flavin-containing monooxygenases: catalytic mechanism and substrate specificitiesQ39654203
Endoxifen (4-hydroxy-N-desmethyl-tamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxy-tamoxifen.Q40463031
CYP2D6-mediated catalysis of tamoxifen aromatic hydroxylation with an NIH shift: similar hydroxylation mechanism in chicken, rat and human liver microsomesQ44353593
Evaluation of xenobiotic N- and S-oxidation by variant flavin-containing monooxygenase 1 (FMO1) enzymesQ44771795
Tamoxifen and metabolite concentrations in serum and breast cancer tissue during three dose regimens in a randomized preoperative trial.Q44836596
Flavin-containing monooxygenase isoform specificity for the N-oxidation of tamoxifen determined by product measurement and NADPH oxidationQ44872457
Differences in FMO2*1 allelic frequency between Hispanics of Puerto Rican and Mexican descentQ45050361
Genetic polymorphisms of human flavin monooxygenase 3 in sulindac-mediated primary chemoprevention of familial adenomatous polyposisQ45205080
Organ specificity of DNA adduct formation by tamoxifen and alpha-hydroxytamoxifen in the rat: implications for understanding the mechanism(s) of tamoxifen carcinogenicity and for human risk assessmentQ46520781
Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobinQ46575106
Involvement of cytochrome P4503A in catalysis of tamoxifen activation and covalent binding to rat and human liver microsomes.Q53468349
A comparative study of tamoxifen metabolism in female rat, mouse and human liver microsomes.Q53473144
Hepatic microsomal mixed-function amine oxidaseQ67358280
Microsomal oxidase. IV. Properties of a mixed-function amine oxidase isolated from pig liver microsomesQ70378536
Tamoxifen metabolism by microsomal cytochrome P450 and flavin-containing monooxygenaseQ71497736
Isoform specificity of trimethylamine N-oxygenation by human flavin-containing monooxygenase (FMO) and P450 enzymes: selective catalysis by FMO3Q77425114
P433issue1-2
P407language of work or nameEnglishQ1860
P921main subjecttamoxifenQ412178
P304page(s)139-147
P577publication date2006-01-01
P1433published inDrug Metabolism ReviewsQ5308857
P1476titleThe role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines
P478volume38

Reverse relations

cites work (P2860)
Q92229907Ancestral-sequence reconstruction unveils the structural basis of function in mammalian FMOs
Q45218281Development of a CD-MEKC method for investigating the metabolism of tamoxifen by flavin-containing monooxygenases and the inhibitory effects of methimazole, nicotine and DMXAA.
Q51770720Dietary trans 10, cis 12-conjugated linoleic acid reduces the expression of fatty acid oxidation and drug detoxification enzymes in mouse liver.
Q45050255Differential gene expression in ERα-positive and ERα-negative breast cancer cells upon leptin stimulation
Q37008890Flavin-containing monooxygenase 3 and human disease
Q55359029In silico prediction of potential chemical reactions mediated by human enzymes.
Q34038020Partial inhibition of estrogen-induced mammary carcinogenesis in rats by tamoxifen: balance between oxidant stress and estrogen responsiveness
Q90525391Production of drug metabolites by human FMO3 in Escherichia coli
Q46639348Role of the Red Ginseng in Defense against the Environmental Heat Stress in Sprague Dawley Rats.
Q36140832SLC15A2 genomic variation is associated with the extraordinary response of sorafenib treatment: whole-genome analysis in patients with hepatocellular carcinoma
Q37772507The potential of knockout mouse lines in defining the role of flavin-containing monooxygenases in drug metabolism
Q36107130Tissue distribution of 4-hydroxy-N-desmethyltamoxifen and tamoxifen-N-oxide
Q47155427Variations in plasma concentrations of tamoxifen metabolites and the effects of genetic polymorphisms on tamoxifen metabolism in Korean patients with breast cancer

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