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Information on EC 1.14.13.8 - flavin-containing monooxygenase
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1.14.13.8 flavin-containing monooxygenaseIUBMB Comments
A flavoprotein. A broad spectrum monooxygenase that accepts substrates as diverse as hydrazines, phosphines, boron-containing compounds, sulfides, selenides, iodide, as well as primary, secondary and tertiary amines [3,4]. This enzyme is distinct from other monooxygenases in that the enzyme forms a relatively stable hydroperoxy flavin intermediate [4,5]. This microsomal enzyme generally converts nucleophilic heteroatom-containing chemicals and drugs into harmless, readily excreted metabolites. For example, N-oxygenation is largely responsible for the detoxification of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) [2,6]
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Word Map
- 1.14.13.8
- methimazole
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orbit
- trimethylamine
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fenna-matthews-olson
- sulfoxide
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n-oxygenation
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s-oxidation
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excitonic
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initio
- n-octylamine
- thioureas
- cyp3a4
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n-demethylation
- tepidum
- bacteriochlorophyll
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antenna
- phenobarbital
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cdna-expressed
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drug-metabolizing
- imipramine
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light-harvesting
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frontier
- cyp2d6
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pigment-protein
- metyrapone
- chlorobium
- cyp2c19
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n-hydroxylation
- aestuarii
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p-450-dependent
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baeyer-villiger
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yucca
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monooxygenation
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hartree-fock
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hamiltonians
- trimethylamine-n-oxide
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butoxide
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pyrrolizidine
- albendazole
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prochiral
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diels-alder
- 1-aminobenzotriazole
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piperonyl
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sulfenic
- drug development
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
fmo, flavin monooxygenase, flavin-containing monooxygenase 3, flavin-dependent monooxygenase, fad-containing monooxygenase, flavoprotein monooxygenase, hfmo3, flavin-containing mono-oxygenase, flavin-containing monooxygenase 1, mixed-function amine oxidase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
dechlorinating flavin-dependent monooxygenase
dimethylaniline monooxygenase (N-oxide-forming)
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dimethylaniline N-oxidase
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dimethylaniline oxidase
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dimethylsulfone monooxygenase
DMA oxidase
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FAD-containing monooxygenase
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FAD-containing monooxygenase 3
flavin mono-oxygenase
flavin monooxygenase
flavin-containing monooxygenase
flavin-containing monooxygenase 1
flavin-containing monooxygenase 3
flavin-containing monooxygenase 5
flavin-containing monooxygenase-3
flavin-dependent monooxygenase
FMO
FMO 1A1
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FMO 1B1
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FMO 1C1
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FMO 1D1
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FMO 1E1
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FMO-I
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FMO-II
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FMO1
FMO2
FMO3
FMO4
FMO5
HadA
mFMO
mixed-function amine oxidase
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N,N-dimethylaniline monooxygenase
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oxygenase, dimethylaniline mono- (N-oxide-forming)
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oxygenase, methylphenyltetrahydropyridine N-mono-
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sfnG
additional information
flavin monooxygenase
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flavin-containing monooxygenase
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FMO
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FMO
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FMO1
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FMO2
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FMO3
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FMO3
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FMO5
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additional information
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the enzyme belongs to the human FMO functional gene family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
ordered ter-bi mechanism with an irreversible step between the second and third substrate, NADPH is added first, followed by O2 and the oxidizable organic substrate last
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
reaction mechanism of S-oxygenation of N-substituted thioureas
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
reaction mechanism of S-oxygenation of N-substituted thioureas
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic reaction mechanism, structure-function relationship, FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, the first step for FMO is reduction of the FAD by NADPH, the next step is formation of a C4a-hydroperoxy flavin by addition of molecular oxygen to the reduced FAD, when the substrate is accepted by FMO the enzyme is already in an active form, the protein environment of FMO apparently protects the hydroperoxy flavin from decomposing, conserving NADPH, and affording an effcient two-electron oxygenating agent for nucleophiles with the appropriate size and shape
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle and catalytic reaction mechanism, structure-function relationship, FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, utilizing the reducing equivalents of NADPH to reduce 1 atom of molecular oxygen to water, while the other atom is used to oxidize the substrate, FMO does not require a reductase to transfer electrons from NADPH, substrate binding has no effect on velocity, formation of a peroxyflavin intermediate
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic reaction mechanism via 4alpha-hydroperoxyflavin transient intermediate
N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism via C4a-hydroperoxyflavin intermediate and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism and structure-function relationship, overview; catalytic cycle, reaction mechanism and structure-function relationship, overview; catalytic cycle, reaction mechanism and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
catalytic cycle, reaction mechanism via C4a-hydroperoxyflavin intermediate and structure-function relationship, overview
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N,N-dimethylaniline + NADPH + H+ + O2 = N,N-dimethylaniline N-oxide + NADP+ + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
N,N-dimethylaniline,NADPH:oxygen oxidoreductase (N-oxide-forming)
A flavoprotein. A broad spectrum monooxygenase that accepts substrates as diverse as hydrazines, phosphines, boron-containing compounds, sulfides, selenides, iodide, as well as primary, secondary and tertiary amines [3,4]. This enzyme is distinct from other monooxygenases in that the enzyme forms a relatively stable hydroperoxy flavin intermediate [4,5]. This microsomal enzyme generally converts nucleophilic heteroatom-containing chemicals and drugs into harmless, readily excreted metabolites. For example, N-oxygenation is largely responsible for the detoxification of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) [2,6]
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CAS REGISTRY NUMBER
COMMENTARY
117910-56-2
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148848-55-9
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37256-73-8
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-metamphetamine + NADPH + H+ + O2
(R)-metamphetamine N-oxide + NADP+ + H2O
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substrate of isoform FMO1
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?
(S)-metamphetamine + NADPH + H+ + O2
(S)-metamphetamine N-oxide + NADP+ + H2O
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substrate of isoforms FMO1 and FMO3
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-
?
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
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(S)-nicotine N-1'-oxygenation
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-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
10-([N,N-dimethylaminopentyl]-2-trifluoromethyl)phenothiazine + NADPH + O2
?
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?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine + NADPH + H+ + O2
10-[(N,N-dimethylaminooctyl)-2-(trifluoromethyl)]phenothiazine N-oxide + NADP+ + H2O
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?
10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine + NADPH + O2
?
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i.e. 5-DPT or diethylenetriaminepentaacetic acid
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?
2 bicyclo[4.2.0]octan-7-one + 2 NADH + 2 H+ + 2 O2
(3aS,7aS)-hexahydro-1-benzofuran-2(3H)-one + (3aR,7aS)-hexahydro-2-benzofuran-1(3H)-one + 2 NAD+ + 2 H2O
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-
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
2-acetylsulfanylmethyl-4-(4-methoxyphenyl)-4-oxobutyric acid + NADPH + H+ + O2
?
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?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
2-[(methylsulfanyl)methyl]furan + NADPH + H+ + O2
2-[(methylsulfanyl)methyl]furan S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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?
2-[2-(4-methoxyphenyl)-2-oxoethyl]-acrylic acid + NADPH + H+ + O2
?
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a synthetic 10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl)phenothiazine analogue
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?
3-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-3-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 15% R-enantiomer as product
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?
4-(4-methoxyphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
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FMO1, poor activity with FMO3 and FMO5
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?
4-(4-methylphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
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FMO1 and FMO5, no activity with FMO3
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?
4-(methylsulfanyl)benzonitrile + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)benzonitrile S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 22% S-enantiomer as product
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?
4-(methylsulfanyl)phenol + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)phenol S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 81% S-enantiomer as product
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?
4-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-4-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 95% S-enantiomer as product
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?
5,6-dimethylxanthenone-4-acetic acid + NADPH + H+ + O2
?
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substrate of isoform FMO3, methyl hydroxylation
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?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
9-hydroxy-5,6-dimethyl-N-(2-(dimethylamino)ethyl)-6H-pyrido(4,3-B)-carbazole-1-carboxamide + NADPH + H+ + O2
2-(9-hydroxy-5,6-dimethyl-6H-pyrido[4,3-b]carbazole-1-carboxamido)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
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substrate of isoform FMO3
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?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
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substrate of isoform FMO3
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?
almotriptan + NADPH + H+ + O2
almotriptan N-oxide + NADP+ + H2O
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substrate of isoform FMO3
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?
amphetamine + NADPH + H+ + O2
amphetamine N-oxide + NADP+ + H2O
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substrate of isoform FMO3
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?
benzydamine + NADPH + H+ + O2
?
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i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
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?
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
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?
butyl ethyl sulfide + NADPH + H+ + O2
butyl ethyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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?
butyl methyl sulfide + NADPH + H+ + O2
butyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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?
clomiphene + NADPH + H+ + O2
?
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i.e. 2-[4-[2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
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?
contezolid + NADPH + H+ + O2
contezolid N-oxide + NADP+ + H2O
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substrate of isoform FMO5
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-
?
cyclohexyl methyl sulfide + NADPH + H+ + O2
cyclohexyl methyl sulfide S-oxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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-
?
danusertib + NADPH + H+ + O2
danusertib N-oxide + NADP+ + H2O
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substrate of isoform FMO3
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-
?
dasatinib + NADPH + H+ + O2
4-(6-((5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-yl)amino)-2-methylpyrimidin-4-yl)-1-(2-hydroxyethyl)piperazine 1-oxide + NADP+ + H2O
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substrate of isoform FMO3
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-
?
deprenyl + NADPH + H+ + O2
deprenyl N-oxide + NADP+ + H2O
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substrate of isoforms FMO1 and FMO3
-
-
?
E-7016 + NADPH + H+ + O2
?
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substrate of isoform FMO5, Bayer Villiger oxidation
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-
?
esonarimod + NADPH + H+ + O2
S-methyl esonarimod + NADP+ + H2O
a antirheumatic drug, is converted to the S-oxide
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-
?
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl sulfoxide + NADP+ + H2O
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sulfoxidation by recombinant PTDH-mFMO fusion protein
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-
?
etionamide + NADPH + H+ + O2
etionamide S-oxide + NADP+ + H2O
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substrate of FMO1, FMO3, and FMO2.1
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-
?
GSK5182 + NADPH + H+ + O2
(Z)-2-(4-(5-hydroxy-1-(4-hydroxyphenyl)-2-phenylpent-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
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-
?
L-775,606 + NADPH + H+ + O2
4-(3-(5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl)-1-(3-fluorophenethyl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
L-methionine + NADPH + H+ + O2
methionine S-oxide + NADP+ + H2O
stereochemistry, overview
formation of 80% D-isomer
-
?
L-Phe-Met + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
lorcaserin + NADPH + H+ + O2
lorcaserin N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
loxapine + NADPH + H+ + O2
4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-1-methylpiperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
mercaptoimidazole + NADPH + H+ + O2
?
-
FMO1 and FMO3, no activity with FMO5
-
-
?
mercaptoimidazole + NADPH + O2
mercaptoimidazole S-oxide + NADP+ + H2O
-
-
-
-
?
methamphetamine + NADPH + H+ + O2
methamphetamine N-oxide + NADP+ + H2O
a psychostimulant, is converted to the hydroxylamine
-
-
?
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
methyl 2-phenylethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
methyl 4-(methylsulfanyl)phenyl ether + NADPH + H+ + O2
(R,S)-methyl 4-(methylsulfanyl)phenyl ether S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 70% S-enantiomer as product
-
-
?
methyl 4-methylphenyl sulfide + NADPH + H+ + O2
(R,S)-methyl 4-methylphenyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 92% S-enantiomer as product
-
-
?
methyl 4-nitrophenyl sulfide + NADPH + H+ + O2
(R,S)-methyl 4-nitrophenyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 37% S-enantiomer as product
-
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R,S)-methyl phenyl sulfoxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 35% S-enantiomer as product
-
-
?
methylthioalkyl glucosinolate + NADPH + H+ + O2
methylsulfinylalkyl glucosinolate S-oxide + NADP+ + H2O
-
-
-
-
?
MK-0457 + NADPH + H+ + O2
MK-0457 N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
moclobemide + NADPH + H+ + O2
moclobemide N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N,N,N-trimethylamine + NADPH + H+ + O2
N,N,N-trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-diallyltryptamine + NADPH + H+ + O2
N,N-diallyltryptamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N,N-dimethyl-3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propan-1-amine + NADPH + H+ + O2
?
-
3-DPT, a phenothiazine analogue, N-oxygenation by FMO1 and FMO3, no activity with FMO5
-
-
?
N,N-dimethyl-5-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]pentan-1-amine + NADPH + H+ + O2
?
-
5-DPT, a phenothiazine analogue, N-oxygenation by FMO1, FMO3, and FMO5
-
-
?
N,N-dimethyl-8-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]octan-1-amine + NADPH + H+ + O2
?
-
8-DPT, a phenothiazine analogue, N-oxygenation by FMO1, FMO3, and FMO5
-
-
?
N,N-dimethylamphetamine + NADPH + H+ + O2
N,N-dimethylamphetamine N-oxide + NADP+ + H2O
-
N-oxygenation mainly by isozyme FMO1, low activity with isozyme FMO3
-
-
?
N,N-dimethylaniline + NADH + H+ + O2
N,N-dimethylaniline N-oxide + NAD+ + H2O
-
-
-
-
?
N-(3R)-1-azabicyclo[2.2.2]oct-3-ylfuro[2,3-c]pyridine-5-carboxamide + NADPH + H+ + O2
(R)-3-(furo[2,3-c]pyridine-5-carboxamido)quinuclidine 1-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
?
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyloxoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
N-methyl-tamoxifen + NADPH + O2
N-methyl-tamoxifen N-oxide + NADP+ + H2O
-
recombinant isozymes FMO1 and FMO3
-
-
?
nicotine + NADPH + H+ + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
NSC645809 + NADPH + H+ + O2
N,N-diethyl-2-((8-hydroxy-6-oxo-6H-imidazo[4,5,1-de]acridin-5-yl)amino)ethan-1-amine oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
olanzapine + NADPH + H+ + O2
1-methyl-4-(2-methyl-10H-benzo[b]thieno[2,3-e][1,4]diazepin-4-yl)piperazine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
orphenadrine + NADPH + H+ + O2
orphenadrine N-oxide + NADP+ + H2O
an anticholinergic drug
-
-
?
pargyline + NADPH + H+ + O2
pargyline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
phenethylamine + NADPH + O2
phenethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
-
-
?
phenyl propyl sulfide + NADPH + H+ + O2
phenyl propyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
phorate + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
phospho-sulindac + NADPH + H+ + O2
?
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
quazepam + NADPH + H+ + O2
7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
?
-
-
-
?
S-allyl-L-cysteine + NADPH + H+ + O2
? + NADP+ + H2O
stereochemmistry, overview
-
-
?
S-benzyl-L-cysteine + NADPH + O2
S-benzyl-L-cysteine S-oxide + NADP+ + H2O
-
isozyme FMO1
-
-
?
S-farnesylcysteine + NADPH + O2
S-farnesylcysteine S-oxide + NADP+ + H2O
-
-
-
-
?
S-farnesylcysteine methyl ester + NADPH + O2
S-farnesylcysteine S-oxide methyl ester + NADP+ + H2O
-
-
-
-
?
S-methyl N,N-diethyldithiocarbamate + NADPH + H+ + O2
(diethylnitroryl)(methylsulfanyl)methanethione + NADP+ + H2O
-
substrate of isoform FMO1 and FMO3
-
-
?
S16020 + NADPH + H+ + O2
S16020 N-oxide + NADP+ + H2O
a topoisomerase II inhibitor and antitumor drug, is converted to the N-oxide
-
-
?
secondary amine + NADPH + O2
secondary nitrone + NADP+ + H2O
-
-
first oxidation to the N-hydroxy amine and then to the corresponding nitrone
?
selegiline + NADPH + H+ + O2
?
-
i.e. (2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
-
-
?
seleno-L-methionine + NADPH + H+ + O2
seleno-L-methionine Se-oxide + NADP+ + H2O
-
-
-
?
selenomethionine + NADPH + H+ + O2
seleno-L-methionine Se-oxideoxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
SNI-2011 + NADPH + H+ + O2
?
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
SNI-2011 + NADPH + H+ + O2
SNI-2011 N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
sulindac sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
tazarotenic acid + NADPH + H+ + O2
?
a retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
TG100435 + NADPH + H+ + O2
1-(2-(4-((7-(2,6-dichlorophenyl)-5-methylbenzo[e][1,2,4]triazin-3-yl)amino)phenoxy)ethyl)pyrrolidine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
-
bioactivation by EtaA
-
-
?
thiobenzamide + NADPH + H+ + O2
thiobenzamide N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
trifluoroperazine + NADPH + H+ + O2
2,3,4-trifluoropyridine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADPH + H+ + O2
-
substrate of isoform FMO3
-
-
?
[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine + NADPH + H+ + O2
[7-(2,6-dichlorophenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-(4-[2-(1-oxy-pyrrolidin-1-yl)-ethoxy]-phenyl)-amine + NADP+ + H2O
-
i.e. TG100435, a multitargeted Src family kinase inhibitor with anticancer activity, FMO3 is the primary enzyme responsible for TG100855 formation, enzyme-mediated retroreduction of TG100855 back to TG100435 is observed catalyzed by a cytochrome P450 reductase, overview
i.e. TG100855, the N-oxide product is also a multitargeted Src family kinase inhibitor with anticancer activity
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
reaction in microsomal detoxification pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, a neurotoxin to nigrostriatal dopaminergic neurons
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + H+ + O2
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide + NADP+ + H2O
-
one of the predominant enzmyes responsible for the oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 21% R-enantiomer as product
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 21% R-enantiomer as product
-
-
?
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
-
with the alkyl side chain varying in length from 5 to 7 carbons, no activity with shorter side chains by isozyme FMO2
-
-
?
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
-
with the alkyl side chain varying in length from 2 to 7 carbons, liver isozyme FMO1
-
-
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
?
10-(N,N-dimethylaminooctyl)2-(trifluoromethyl)phenothiazene + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
?
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
-
-
-
?
10-(N,N-dimethylaminopentyl)-2-(trifluoromethyl)phenothiazine + NADPH + O2
?
-
isozyme FMO3
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
-
-
-
?
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine + NADPH + O2
10-N-(n-octylamino)-2-(trifluoromethyl) phenothiazine N-oxide + NADP+ + H2O
-
formation of the cis-oxime
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
-
72% conversion
-
-
?
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
-
72% conversion
-
-
?
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
-
100% conversion
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)pyridine + NADPH + H+ + O2
2-(methylsulfanyl)pyridine S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-(methylsulfanyl)thiophene + NADPH + H+ + O2
2-(methylsulfanyl)thiophene S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 75% R-enantiomer as product
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 75% R-enantiomer as product
-
-
?
4-chlorphenol + O2
hydroquinone + H2O + Cl-
-
100% conversion
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-hydroxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
-
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1299
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
i.e. C-1305
-
-
?
5-[[3-(dimethylamino)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADPH + H+ + O2
5-[[3-(dimethylnitroryl)propyl]amino]-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one + NADP+ + H2O
-
i.e. C-1299
-
-
?
amphetamine + NADPH + H+ + O2
?
an antipsychotic agent, is converted to the hydroxylamine
-
-
?
amphetamine + NADPH + H+ + O2
?
-
an antipsychotic agent, is converted to the hydroxylamine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
a nonsteroidal antiinflammatory drug, is converted to the N-oxide
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
highest activity of all isoforms tested
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
a dopemaine D2 antagonist
-
-
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
-
a dopemaine D2 antagonist
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
-
S-oxygenation of cimetidine, i.e. CIM, a histamine H2-receptor antagonist of therapeutic utility in the treatment of peptic ulcer disease and gastric hypersecretory syndromes. Development of in-line screening and an off-line chiral CE method for determination of the stereoselectivity of flavin-containing monooxygenase isoforms FMO1, FMO3, and FMO5 using chiral specific selectors, overview
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
an antipsychotic agent, is converted to the N-oxide
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
an antipsychotic agent, is converted to the N-oxide
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
dapsone + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
-
i.e. O,O-diethyl O-2-ethylthioethyl phosphorothioate, isozymes FMO1 and FMO3, higher activity by FMO1
-
-
?
deprenyl + NADPH + H+ + O2
?
a monoamine oxidase type B inhibitor, is converted to the hydroxylamine
-
-
?
deprenyl + NADPH + H+ + O2
?
-
a monoamine oxidase type B inhibitor, is converted to the hydroxylamine
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
-
i.e. alpha-ethylthio-o-tolyl methylcarbamate, isozymes FMO1 and FMO3, higher activity by FMO1
-
-
?
ethionamide + NADPH + H+ + O2
?
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
i.e. ETA, S-oxygenation by isozymes FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
-
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide is a pro-drug requiring bioactivation to exert toxicity
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
i.e. ETA, S-oxygenation by isozymes FMO1, FMO2, and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by isozymes FMO1 and FMO3
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
a thioamide-containing second line antitubercular prodrug
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
bioactivation by EtaA
-
-
?
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
-
a thioamide-containing second line antitubercular prodrug
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
-
more than 95% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
-
i.e. O,O-dimethyl O-4-methylthio-m-tolyl phosphorothioate, isozymes FMO1 and FMO3, stereospecifc product formation, overview
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
an antidepressant, is converted to the N-oxide
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
an antidepressant, is converted to the N-oxide
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
Q83XK4
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
Q83XK4
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
a dopamine D2 receptor antagonist, is converted to the N-oxide
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
a dopamine D2 receptor antagonist, is converted to the N-oxide
-
-
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
a cysteine protease inhibitor against Trypanosoma cruzi, is converted to the N-oxide
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
isozymes FMO1-FMO4
-
-
?
L-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
-
isozymes FMO1-FMO4, low activity by isozyme FMO1
-
-
?
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
-
liver microsomes
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
-
free and N-terminally peptide-bound L-methionine, no activity with modified peptide-bound methionine and with N-acetyl-L-methionine, isozymes FMO1-FMO4
stereospecificity for formation of the D-isomer, especially by isozyme FMO3
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
-
purified liver isozymes FMO1 and FMO3
-
-
?
methamphetamine + NADPH + H+ + O2
?
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + H+ + O2
?
-
a psychostimulant, is converted to the hydroxylamine
-
-
?
methimazole + NADPH + H+ + O2
?
a thyroperoxidase inhibitor
-
-
?
methimazole + NADPH + H+ + O2
?
a thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
?
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
an thyroperoxidase inhibitor, is converted to the S-oxide
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
about 25% of the activityy with substrate benzydamine
-
-
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
low activity with FMO2.1, moderate activity with FMO3, high activity with FMO1
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
i.e. N-methyl-2-mercaptoimidazole
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
FMO3 5000 times more efficient than FMO5
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
-
-
-
-
?
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
-
i.e. 4-methylthio-3,5-xylyl methylcarbamate, isozyme FMO1 acts stereospecifically, no activity by isozyme FMO3
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl p-tolyl sulfide + NADPH + H+ + O2
?
-
FMO1, FMO2, but poor substrate of FMO3
-
-
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
-
-
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
stereochemistry: product 49% R-enantiomer
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
-
-
26% R
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
a peroxisome proliferator receptor activator, is converted to the S-oxide
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + H+ + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
-
-
?
N,N-dimethylaniline + NADPH + O2
N,N-dimethylaniline N-oxide + NADP+ + H2O
-
-
348485, 348486, 348487, 348488, 348490, 348491, 348492, 348494, 348497, 348498, 348499, 348505, 676315
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
recombinant protein expressed in E. coli
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
-
lung enzyme active, liver enzyme not
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
a stimulant, is converted to the trans-N-oxide
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
-
-
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
an antihistamininc drug, is converted to the N-oxide
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
-
an antihistamininc drug, is converted to the N-oxide
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
-
S-oxidase activity
-
-
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
-
S-oxidase activity
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
an antitumor drug, is converted to the N-oxide
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
ranitidine + NADPH + H+ + O2
?
an antihistamininc drug, is converted to the N-oxide and/or S-oxide
-
-
?
ranitidine + NADPH + H+ + O2
?
-
substrate of isoforms FMO3 and FMO5, S-oxygenation and N-oxygenation
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
a cytokine production inhbitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
an cytokine production inhbitor, is converted to the S-oxide
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
sulfamethoxazole + NADPH + O2
?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
S-oxidation, low activity
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
a nonsteroidal antiinflammatory drug, is converted to the S-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
?
-
i.e. (Z)-2-[4-(1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
an estrogen receptor modulator, is converted to the N-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
an estrogen receptor modulator, is converted to the N-oxide
-
-
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen metabolism pathways involving FMOs and CYP450s, tamoxifen N-oxide is reconverted into tamoxifen by reduced hemoglobin and NADPH-P450 oxidoreductase, a metabolic cycle in vivo, overview
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, low level of tamoxifen N-oxide production in human liver microsomes may be explained by the kinetics of FMO1 versus FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. (Z)-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene), a drug used in breast cancer therapy, isozymes FMO1 and FMO3
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway, high activity by isozyme FMO1
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. Z-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
tamoxifen N-oxygenation represents a detoxication pathway
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
-
i.e. (Z)-(1-[4-(2-dimethyl-aminoethoxy)phenyl]-1,2-diphenyl-1-butene)
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
an retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by isozymes FMO1 and FMO3, two-step process
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
a thiourea-containing second line antitubercular prodrug
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
bioactivation by EtaA
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
-
a thiourea-containing second line antitubercular prodrug
-
-
?
thiacetazone + NADPH + H+ + O2
?
a anti-tubercular drug, high activity
-
-
?
thiacetazone + NADPH + H+ + O2
?
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
?
-
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
-
an antibiotic agent, is converted to the sulfinic acid/carbodiimide
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
-
low activity with FMO1 and FMO3, high activity with FMO2.1
-
-
?
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
-
substrate of isoforms FMO1, FMO2, and FMO3
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
detoxification, the organism is resistant against the antibiotic
-
-
?
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
-
a glycylcycline derivative containing a 9-tert-butylglycylamido group belonging to the tetracyline antibiotic compounds
product identification by LC-MS
-
?
tozasertib + NADPH + H+ + O2
?
-
i.e. N-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin2yl]sulfanylphenyl]cyclopropane carboxamide
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
mutations of FMO3 are involved in trimethylaminuria, primary trimethylaminuria is multifactorial in origin in that enzyme dysfunction can result from kinetic incompetencies as well as impaired assembly of holoprotein, overview
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
KC734478, KC734481, KC734482, KC734486
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
isozyme FMO3
-
-
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
-
preferred substrate of isozyme FMO3
-
-
?
voriconazole + NADPH + H+ + O2
?
-
liver microsomes, a potent second-generation triazole antifungal agent with broad-spectrum activity against clinically important fungi
-
-
?
voriconazole + NADPH + H+ + O2
?
-
recombinant FMO1 and FMO3, no activity with FMO5, N-oxidation of the fluoropyrimidine ring, its hydroxylation, and hydroxylation of the adjacent methyl group
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
a muscarinic receptor antagonist, is converted to the N-oxide
-
-
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
additional information
?
-
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
-
additional information
?
-
enhanced disease susceptibility1, EDS1, controls defense activation and programmed cell death conditioned by intracellular Toll-related immune receptors that recognize specific pathogen effectors in Arabidopsis thaliana, EDS1 is also needed for basal resistance to invasive pathogens by restricting the progression of disease, EDS1 with phytoalexin-deficient 4, PAD4, regulates accumulation of the phenolic defense molecule salicylic acid, EDS1 is regulated by FMO and the Nudix hydrolase NUDT7
-
-
-
additional information
?
-
-
isozyme FMO1 is an essential component of biologically induced systemic acquired resistance, e.g. versus the bacterial pathogen Pseudomonas syringae pv maculicola, resistance is accompanied by accumulation of salicylic acid, overview
-
-
-
additional information
?
-
-
the enzyme is important for pathogen defense and resistance participating in the detoxification of virulence factors produced by pathogens, overview
-
-
-
additional information
?
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tigecycline displays a broad spectrum of antibacterial activity and circumvents the efflux and ribosomal protection resistance mechanisms, Mg2+-complexing is required for ribosome binding, 11a-hydroxytigecycline forms a weaker complex with magnesium than tigecycline, structure, overview
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additional information
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benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
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the enzyme does not oxidize glutathione or cysteine
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the enzyme does not oxidize glutathione or cysteine
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modulation of activity by site directed mutagenesis
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overview on substrate specifities and requirements of FMO1, FMO3
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arylamine compounds, such as sulfamethoxazole and dapsone, are metabolized in epidermal keratinocytes to arylhydroxylamine metabolites that autooxidize to arylnitroso derivatives, which in turn bind to cellular proteins and can act as antigens/immunogens, methimazole and 4-aminobenzoic acid hydrazide attenuate the protein haptenation, overview
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additional information
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effects of genetic variants of isozyme FMO3 on N- and S-oxygenation activities, FMO3 polymorphisms are responsible for the genetic disorder trimethylaminuria, or fish-like odor syndrome, overview
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, isozymes FMO1-FMO3 are involved in detoxication and drug metabolism, FMO3 deficiency causes the disease trimethylaminuria
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FMOs are, together with cytochrome P450 monooxygenases, the major oxidative enzymes in phase I metabolism, extrahepatic metabolism of carbamate and organophosphate thioether compounds, isozyme FMO1 shows higher turnover numbers than isozyme FMO3 for all pesticides studies, overview
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FMOs catalyze NADPH-dependent monooxygenation of soft-nucleophilic nitrogen, sulfur, and phosphorous atoms contained within various drugs, pesticides, and xenobiotics, isozyme FMO3 is responsible for the majority of FMO-mediated xenobiotic metabolism in the adult human liver, FMO3 mutations causing defects in trimethylamine N-oxygenation, result in the disorder known as trimethylaminuria, TMAU, or fish-odour syndrome, overview, interindividual variability in the expression of FMO3 affect drug and exogenous chemical metabolism in the liver and other tissues
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, FMO is not induced by xenobiotics, isozyme FMO3 mutant alleles contribute to the disease known as trimethylaminuria, the enzyme is involved in detoxification and drug metabolism, overview, expression of FMO5 is markedly down-regulated in the liver of humans with type II diabetes, patients diagnosed with atrial fibrillation document a significant increase in the expression of FMO1, FMO may be associated with sideroblastic anemia, FMO3 mutations lead to trimethylaminuria, detailed overview
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the enzyme catalyzes the NADPH-dependent N-and S-oxidation of a variety of therapeutics, environmental toxicants, carcinogens, and nutrients
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carbophenothion, i.e. S-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate, and fonofos, i.e. O-ethyl S-phenyl (RS)-ethylphosphonodithioate, are poor substrates
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FMO oxygenates drugs and xenobiotics containing a soft nucleophile, usually nitrogen or sulfur, isozyme substrate specificity, detailed overview, no activity with 1,3-diphenylthiourea
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FMO oxygenates soft nucleophiles, and converts lipophilic compounds into more hydrophilic metabolites, potential adverse drug-drug interactions are minimized for drugs prominently metabolized by FMO, substrate specificities of isozmes, overview
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stereoselectivity of male and female liver microsomes, and of recombinant isozymes FMO1, FMO3, and FMO4, overview
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drug metabolism, overview, enzyme mutations are involved in development of trimethylaminuria or fish-odor-syndrome, overview
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drug metabolism, overview, most humans are homozygous for a nonsense mutation that inactivates FMO2. But a substantial proportion of sub-Saharan Africans express functional FMO2 and, thus, are predicted to respond differently to drugs and other foreign chemicals
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drug metabolism, overview, the FMO1 gene is downregulated in the spinal cord of patients with the neurodegenerative disease amyotrophic lateral sclerosis, but is upregulated in the myocardial tissue of patients with atrial fibrillation
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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FMO2 catalyzes the S-oxygenation of organophosphates representing a detoxification pathway
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additional information
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human FMO3 regulatory elements, overview
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the enzyme is regulated by hormones, e.g. testosterone
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FMO1 mediates the formation of a reactive intermediate of 4-fluoro-N-methylaniline. FMO1 catalyzes a carbon oxidation reaction coupled with defluorination that leads to the formation of 4-N-methylaminophenol, mechanism, overview. A labile 1-fluoro-4-(methylimino)cyclohexa-2,5-dienol intermediate is formed leading to an electrophilic quinoneimine intermediate
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isoform FMO5 exhibits a low catalytic activity only for sulfoxidation of methyl 4-tolyl sulfide
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S-oxygenation of N-substituted thioureas
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substrate specificity, the ability to stabilize the hydroperoxyflavin intermediate in substrate oxygenation is crucial involving NADP(H), overview
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substrate specificity, the ability to stabilize the hydroperoxyflavin intermediate in substrate oxygenation is crucial involving NADP(H), overview
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substrate specificity of the recombinant PTDH-mFMO fusion enzyme, overview
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substrate specificity of the recombinant PTDH-mFMO fusion enzyme, overview
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FMO oxygenates a number of drugs and xenobiotics containing a soft-nucleophile heteroatom, mostly sulfur- and nitrogen-containing xenobiotics, and is involved in detoxication
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additional information
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview, hepatic total FMO activity is enhanced in mouse models of type I and type II diabetes
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the enzyme is involved in fatty acid oxidation in the liver, as well as in drug detoxification
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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flavin-containing monooxygenases catalyze the addition of oxygen to many sulfur-, nitrogen-, phosphorus-, and selenium-containing compounds including pesticides, therapeutics, and dietary substances
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additional information
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regulation of the enzyme expression by hypersaline conditions and the osmoregulatory hormonecortisol, overview
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additional information
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nitrogen- and sulfur-containing endogenous substrates and physiologic functions, the enzyme is involved in detoxification and drug metabolism, overview
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additional information
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the enzyme is involved in oxidative metabolism of drugs and other chemicals
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additional information
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stereoselectivity of recombinant isozymes FMO1, FMO2, and FMO3
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additional information
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the lung isozyme is distinct from the liver isozyme in having high activity toward primary alkyl amines, restricted substrate specificity related to steric properties, resistance to detergent inhibition and enhanced thermal stability, and restricted substrate access, no activity of the lung isozyme with 1,3-diphenylthiourea, chlorpromazine and imipramine by isozyme FMO2, isozyme substrate specificity, detailed overview
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additional information
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benzydamine is a weak base and an indazole derivative with analgesic and antipyretic properties used in human and veterinary medicine, it is metabolized to a wide range of metabolites. One of the main metabolites, benzydamine N-oxide is produced in the liver and brain by flavin-containing monooxygenases
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additional information
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the enzyme is involved in detoxification, generally, metabolites produced by FMO-catalysed reactions are more hydrophilic and less toxic, and are easily excreted from the body
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