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(R)-metamphetamine + NADPH + H+ + O2
(R)-metamphetamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO1
-
-
?
(S)-metamphetamine + NADPH + H+ + O2
(S)-metamphetamine N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
(S)-nicotine + NADPH + H+ + O2
?
-
-
-
-
?
(S)-nicotine + NADPH + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
(S)-nicotine N-1'-oxygenation
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
1,2-dimethylhydrazine + NADPH + O2
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
1-butanethiol + NADPH + O2
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
1-methyl-2-benzylhydrazine + NADPH + O2
?
1-methyl-2-thioimidazole + NADPH + O2
?
-
-
-
-
?
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 + O2
?
1-methyl-6,7-dihydroxytetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1-[4-(methylsulfanyl)phenyl]ethanone + NADPH + H+ + O2
(R,S)-1-[4-(methylsulfanyl)phenyl]ethanone S-oxide + NADP+ + H2O
10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl) phenothiazines + NADPH + O2
?
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
?
-
-
-
-
?
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
-
-
-
-
?
10-[(N,N-dimethylaminopentyl)-2-(trifluoromethyl)]phenothiazine + NADPH + O2
?
-
i.e. 5-DPT or diethylenetriaminepentaacetic acid
-
-
?
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
-
-
-
-
?
2,4,5-trichlorphenol + O2
2,5-dichlorohydroquinone + H2O + Cl-
2,4,6-trichlorphenol + O2
2,6-dichlorohydroquinone + H2O + Cl-
2,4-dichlorphenol + O2
chlorohydroquinone + H2O + Cl-
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
?
-
-
-
-
?
2-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-2-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
2-chlorphenol + O2
chlorohydroquinone + H2O
2-mercaptobenzimidazole + NADPH + O2
?
2-[(methylsulfanyl)methyl]furan + NADPH + H+ + O2
2-[(methylsulfanyl)methyl]furan S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
2-[2-(4-methoxyphenyl)-2-oxoethyl]-acrylic acid + NADPH + H+ + O2
?
-
a synthetic 10-(N,N-dimethylaminoalkyl)-2-(trifluoromethyl)phenothiazine analogue
-
-
?
3-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-3-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 15% R-enantiomer as product
-
-
?
4-(4-methoxyphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
-
FMO1, poor activity with FMO3 and FMO5
-
-
?
4-(4-methylphenyl)-2-methylsulfanylmethyl-4-oxobutyric acid + NADPH + H+ + O2
?
-
FMO1 and FMO5, no activity with FMO3
-
-
?
4-(methylsulfanyl)benzonitrile + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)benzonitrile S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 22% S-enantiomer as product
-
-
?
4-(methylsulfanyl)phenol + NADPH + H+ + O2
(R,S)-4-(methylsulfanyl)phenol S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 81% S-enantiomer as product
-
-
?
4-aminobenzoic acid hydrazide + NADPH + O2
?
-
-
-
?
4-chlorophenyl methyl sulfide + NADPH + H+ + O2
(R,S)-4-chlorophenyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation of the thioanisole derivative by recombinant PTDH-mFMO fusion protein. Enantiomeric reaction with 95% S-enantiomer as product
-
-
?
4-chlorphenol + O2
hydroquinone + H2O + Cl-
5,6-dimethylxanthenone-4-acetic acid + NADPH + H+ + O2
?
-
substrate of isoform FMO3, methyl hydroxylation
-
-
?
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
-
substrate of isoform FMO3
-
-
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
aldicarb + NADPH + O2
?
-
-
-
-
?
almotriptan + NADPH + H+ + O2
almotriptan N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
aminopyrine + NADPH + O2
?
ammonia + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
amphetamine + NADPH + H+ + O2
?
amphetamine + NADPH + H+ + O2
amphetamine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
amphetamine + NADPH + O2
amphetamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzydamine + NADPH + H+ + O2
?
-
i.e. 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine
-
-
?
benzydamine + NADPH + H+ + O2
benzydamine N-oxide + NADP+ + H2O
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
benzyl ethyl sulfide + NADPH + H+ + O2
benzyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzyl methyl sulfide + NADPH + H+ + O2
benzyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
benzylamine + [reduced NADPH-hemoprotein reductase] + O2
benzylamine N-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
beta-ethylphenylhydrazine + NADPH + O2
?
bicyclo[3.2.0]hept-2-en-6-one + NADH + H+ + O2
?
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
-
-
-
-
?
bupivacaine + NADPH + O2
bupivacaine-oxide + NADP+
-
-
-
-
?
butyl ethyl sulfide + NADPH + H+ + O2
butyl ethyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butyl methyl sulfide + NADPH + H+ + O2
butyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
butylhydrazine + NADPH + O2
?
chlorpromazine + NADPH + H+ + O2
chlorpromazine N-oxide + NADP+ + H2O
chlorpromazine + NADPH + H+ + O2
chlorpromazine oxide + NADP+ + H2O
-
-
-
-
?
chlorpromazine + NADPH + O2
?
chlorpromazine + NADPH + O2
chlorpromazine N-oxide + NADP+ + H2O
-
-
-
-
?
cimetidine + NADPH + H+ + O2
cimetidine S-oxide + NADP+ + H2O
cimetidine + NADPH + O2
cimetidine S-oxide + NADP+ + H2O
-
-
-
-
?
clomiphene + NADPH + H+ + O2
?
-
i.e. 2-[4-[2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine
-
-
?
clozapine + NADPH + H+ + O2
?
-
-
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
clozapine + NADPH + O2
?
-
-
-
-
?
contezolid + NADPH + H+ + O2
contezolid N-oxide + NADP+ + H2O
-
substrate of isoform FMO5
-
-
?
cyclobutanone + NADH + H+ + O2
gamma-butyrolactone + NAD+ + H2O
-
-
-
-
?
cyclohexyl methyl sulfide + NADPH + H+ + O2
cyclohexyl methyl sulfide S-oxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
cysteamine + NADPH + H+ + O2
?
cysteamine + NADPH + O2
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
danusertib + NADPH + H+ + O2
danusertib N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
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
-
substrate of isoform FMO3
-
-
?
demeton-O + NADPH + O2
demeton-O sulfoxide + NADP+ + H2O
deprenyl + NADPH + H+ + O2
?
deprenyl + NADPH + H+ + O2
deprenyl N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
dibenzylamine + NADPH + O2
?
dihydrolipoic acid + NADPH + O2
?
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
disulfoton + NADPH + H+ + O2
?
E-7016 + NADPH + H+ + O2
?
-
substrate of isoform FMO5, Bayer Villiger oxidation
-
-
?
esonarimod + NADPH + H+ + O2
S-methyl esonarimod + NADP+ + H2O
a antirheumatic drug, is converted to the S-oxide
-
-
?
ethiofencarb + NADPH + O2
ethiofencarb sulfoxide + NADP+ + H2O
ethionamide + NADPH + H+ + O2
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
ethionamide + NADPH + H+ + O2
ethionamide S-oxide + NADP+ + H2O
ethionamide + NADPH + O2 + H+
2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O
ethyl phenyl sulfide + NADPH + H+ + O2
ethyl phenyl sulfoxide + NADP+ + H2O
-
sulfoxidation by recombinant PTDH-mFMO fusion protein
-
-
?
ethylene sulfide + NADPH + O2
?
ethylene thiourea + NADPH + H+ + O2
?
-
-
-
-
?
ethylenethiourea + NADPH + O2
ethylenethiourea S-oxide + NADP+ + H2O
-
-
-
-
?
ethylenthiourea + NADPH + O2
?
-
-
-
-
?
etionamide + NADPH + H+ + O2
etionamide S-oxide + NADP+ + H2O
-
substrate of FMO1, FMO3, and FMO2.1
-
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+
-
-
74% (+)-sulfoxide
-
?
fenthion + NADPH + O2
fenthion sulfoxide + NADP+ + H2O
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
-
-
?
imipramine + NADPH + H+ + O2
imipramine N-oxide + NADP+ + H2O
imipramine + NADPH + H+ + O2
imipramine oxide + NADP+ + H2O
-
-
-
-
?
imipramine + NADPH + O2
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
isopropylhydrazine + NADPH + O2
?
itopride + NADPH + H+ + O2
itopride N-oxide + NADP+ + H2O
itopride + NADPH + O2
?
-
-
-
-
?
K11777 + NADPH + H+ + O2
K11777 N-oxide + NADP+ + H2O
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-Met-Phe + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
L-Met-Val + NADPH + O2
(L-Met-S-oxide)-Val + NADP+ + H2O
L-methionine + NADPH + H+ + O2
?
-
-
-
?
L-methionine + NADPH + H+ + O2
L-methionine S-oxide + NADP+ + H2O
-
-
-
-
?
L-methionine + NADPH + H+ + O2
methionine S-oxide + NADP+ + H2O
stereochemistry, overview
formation of 80% D-isomer
-
?
L-methionine + NADPH + O2
L-methionine S-oxide + NADP+ + H2O
L-Phe-Met + NADPH + O2
(L-Met-S-oxide)-Phe + NADP+ + H2O
-
liver microsomes
-
-
?
L-seleno-methionine + NADPH + O2
L-methionine seleno-oxide + NADP+ + H2O
lidocaine + NADPH + O2
lidocaine-oxide + NADP+
-
-
-
-
?
lipoic acid + NADPH + O2
?
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 + NADPH + H+ + O2
methamphetamine N-oxide + NADP+ + H2O
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2
?
methimazole + NADPH + H+ + O2
?
methimazole + NADPH + H+ + O2
methimazole N-oxide + NADP+ + H2O
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADP+ + H2O
methimazole + NADPH + H+ + O2
methimazole S-oxide + NADPH + H+ + O2
-
-
-
-
?
methimazole + NADPH + O2
?
methimazole + NADPH + O2
N-methylmethimidazole-2-sulfinic acid + NADP+ + H2O
methiocarb + NADPH + O2
methiocarb sulfoxide + NADP+ + H2O
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 4-tolyl sulfide + NADPH + O2
methyl 4-tolyl sulfoxide + NADP+ + H2O
methyl p-tolyl sulfide + NADPH + H+ + O2
?
methyl p-tolyl sulfide + NADPH + O2
methyl p-tolyl sulfoxide + NADP+ + H2O
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
-
-
?
methyl-4-tolyl sulfide + NADPH + H+ + O2
?
-
-
-
-
?
methylmercaptan + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
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
-
-
?
MK-0767 methyl sulfide + NADPH + H+ + O2
?
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,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-(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-aminohomopiperidine + NADPH + O2
?
N-aminomorpholine + NADPH + O2
?
N-aminopiperidine + NADPH + O2
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
N-aminopyrrolidone + NADPH + O2
?
N-deacetyl ketoconazole + NADPH + H+ + O2
?
an antifungal agent, is converted to the N-hydroxyl
-
-
?
N-deacetyl ketoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
N-deacetyloxoconazole + NADPH + H+ + O2
N-deacetyl ketoconazole N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
n-decylamine + NADPH + O2
1-nitrosodecane + NADP+ + H2O
N-methyl-1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
N-methyl-tamoxifen + NADPH + O2
N-methyl-tamoxifen N-oxide + NADP+ + H2O
-
recombinant isozymes FMO1 and FMO3
-
-
?
n-octylamine + NADPH + O2
1-nitrosooctane + NADP+ + H2O
naphthylthiourea + NADPH + O2
naphthylthiourea S-oxide + NADP+ + H2O
nicotine + NADPH + H+ + O2
(S)-nicotine N1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
nicotine + NADPH + H+ + O2
nicotine N-oxide + NADP+ + H2O
nomifensine + NADPH + H+ + O2
?
-
substrate of isoforms FMO3 and FMO5
-
-
?
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
-
-
?
olopatadine + NADPH + H+ + O2
olopatadine N-oxide + NADP+ + H2O
orphenadrine + NADPH + H+ + O2
orphenadrine N-oxide + NADP+ + H2O
an anticholinergic drug
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
p-tolyl sulfide + NADPH + O2
p-tolyl sulfoxide + NADP+ + H2O
pargyline + NADPH + H+ + O2
pargyline N-oxide + NADP+ + H2O
-
substrate of isoforms FMO1 and FMO3
-
-
?
pargyline + NADPH + O2
?
-
inhibitor of monoaminoxidase B
-
-
?
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
-
-
?
phenylhydrazine + NADPH + O2
?
phenylthiourea + NADPH + O2
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
phorate + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
phospho-sulindac + NADPH + H+ + O2
?
-
substrate of isoforms FMO1, FMO3, and FMO5
-
-
?
primaquine + NADPH + H+ + O2
?
-
substrate of isoform FMO3
-
-
?
procarbazine + NADPH + O2
?
propranolol + NADPH + O2
propranolol-hydroxylamine + NADP+
-
-
-
-
?
pyrazolacridine + NADPH + H+ + O2
pyrazolacridine N-oxide + NADP+ + H2O
pyrazoloacridine + NADPH + O2
pyrazoloacridine N-oxide + NADP+ + H2O
-
-
-
-
?
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
-
-
?
R(-)-deprenyl + NADPH + O2
?
-
inhibitor of monoaminoxidase B
-
-
?
ranitidine + NADPH + H+ + O2
?
ranitidine + NADPH + O2
?
-
-
-
-
?
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 methyl ester + NADPH + O2
S-farnesylcysteine S-oxide methyl ester + NADP+ + H2O
-
-
-
-
?
S-methyl esonarimod + NADPH + H+ + O2
?
S-methyl esonarimod + NADPH + H+ + O2
S-methyl esonarimod S-oxide + 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
-
-
?
selegiline + NADPH + O2
selegiline N-oxide + NADP+
-
-
-
-
?
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
-
-
?
sulfamethoxazole + NADPH + O2
?
sulindac sulfide + NADPH + H+ + O2
?
-
substrate of isoforms FMO1 and FMO3
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
sulindac sulfide + NADPH + O2
(S,R)-sulindac + NADP+ + H2O
-
-
-
-
?
sulindac sulfide + NADPH + O2
sulindac + NADP+ + H2O
-
-
-
-
?
tamoxifen + NADPH + H+ + O2
?
tamoxifen + NADPH + H+ + O2
tamoxifen N-oxide + NADP+ + H2O
tamoxifen + NADPH + O2
?
-
-
-
-
?
tamoxifen + NADPH + O2
tamoxifen N-oxide + NADP+ + H2O
tazarotenic acid + NADPH + H+ + O2
?
a retinoic acid receptor modulator, is converted to the S-oxide
-
-
?
tazarotenic acid + NADPH + H+ + O2
tazarotenate N-oxide + NADP+ + H2O
tertiary amine + NADPH + O2
tertiary N-oxide + NADP+ + H2O
-
-
-
-
?
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
-
-
?
TG100435 + NADPH + H+ + O2
?
-
substrate of isoform FMO1
-
-
?
thiacetazone + 2 NADPH + 2 H+ + 2 O2
thiacetazone carbodiimide + 2 NADP+ + 2 H2O
thiacetazone + 2 NADPH + 2 O2
(E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O
-
bioactivation by EtaA
-
-
?
thiacetazone + NADPH + H+ + O2
?
thiacetazone + NADPH + H+ + O2
thiacetazone N-oxide + NADP+ + H2O
thiacetazone + NADPH + H+ + O2
thiacetazone S-oxide + NADP+ + H2O
thioacetamide + NADPH + O2
?
thiobenzamide + NADPH + H+ + O2
thiobenzamide N-oxide + NADP+ + H2O
-
N-oxidation
-
-
?
thiobenzamide + NADPH + O2
?
thiocarbanilide + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
tigecycline + NADPH + O2
11a-hydroxytigecycline + NADP+ + H2O
tozasertib + NADPH + H+ + O2
?
triethylamine + NADPH + H+ + O2
triethylamine N-oxide + NADP+ + H2O
-
-
-
-
?
trifluoperazine + NADPH + O2
?
-
-
-
-
?
trifluoroperazine + NADPH + H+ + O2
2,3,4-trifluoropyridine 1-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
trifluoroperazine + NADPH + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADP+ + H2O
trimethylamine + NADPH + H+ + O2
trimethylamine N-oxide + NADPH + H+ + O2
-
substrate of isoform FMO3
-
-
?
trimethylamine + NADPH + O2
?
trimethylamine + NADPH + O2
trimethylamine N-oxide + NADP+ + H2O
tyramine + NADPH + O2
tyramine N-oxide + NADP+ + H2O
-
-
-
-
?
voriconazole + NADPH + H+ + O2
?
xanomeline + NADPH + H+ + O2
xanomeline N-oxide + NADP+ + H2O
[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
-
?
additional information
?
-
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+
-
-
-
?
1,1-dimethylhydrazine + NADPH + O2
formaldehyde + CH3N2H3 + NADP+
-
possibly, and other 1,1-disubstituted hydrazines
-
?
1,2,3,4-tetrahydroisoquinoline + NADPH + O2

?
-
-
-
-
?
1,2,3,4-tetrahydroisoquinoline + NADPH + O2
?
-
-
-
-
?
1,2-dimethylhydrazine + NADPH + O2

?
-
-
-
-
?
1,2-dimethylhydrazine + NADPH + O2
?
-
-
-
-
?
1,2-dimethylphenylhydrazine + NADPH + O2

?
-
-
-
-
?
1,2-dimethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2

?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-butanethiol + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2

?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-1-phenylhydrazine + NADPH + O2
?
-
-
-
-
?
1-methyl-2-benzylhydrazine + NADPH + O2

?
-
-
-
-
?
1-methyl-2-benzylhydrazine + NADPH + O2
?
-
-
-
-
?
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-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2

?
-
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + NADPH + O2
?
-
-
-
-
?
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
-
-
?
2-chlorphenol + O2

chlorohydroquinone + H2O
-
-
-
-
?
2-chlorphenol + O2
chlorohydroquinone + H2O
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2

?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
2-mercaptobenzimidazole + NADPH + O2
?
-
-
-
-
?
4-chlorphenol + O2

hydroquinone + H2O + Cl-
-
100% conversion
-
-
?
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
-
-
?
alpha-naphthylthiourea + NADPH + O2

?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
alpha-naphthylthiourea + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2

?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
aminopyrine + NADPH + O2
?
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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 + H+ + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
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
-
-
?
benzydamine + NADPH + O2
benzydamine N-oxide + NADP+ + H2O
-
-
-
-
?
benzylhydrazine + NADPH + O2

?
-
-
-
-
?
benzylhydrazine + NADPH + O2
?
-
-
-
-
?
beta-ethylphenylhydrazine + NADPH + O2

?
-
-
-
-
?
beta-ethylphenylhydrazine + NADPH + O2
?
-
-
-
-
?
butylhydrazine + NADPH + O2

?
-
-
-
-
?
butylhydrazine + NADPH + O2
?
-
-
-
-
?
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
-
-
?
chlorpromazine + NADPH + O2

?
-
-
-
-
?
chlorpromazine + NADPH + O2
?
-
liver microsomes
-
-
?
chlorpromazine + NADPH + O2
?
-
liver isozyme FMO1
-
-
?
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
-
N-oxidation
-
-
?
clozapine + NADPH + H+ + O2
clozapine N-oxide + NADP+ + H2O
-
substrate of isoform FMO3
-
-
?
cysteamine + NADPH + H+ + O2

?
-
-
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + H+ + O2
?
-
-
-
-
?
cysteamine + NADPH + O2

?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2
?
-
-
-
-
?
cysteamine + NADPH + O2

cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
cysteamine + NADPH + O2
cysteamine N-oxide + NADP+ + H2O
-
-
-
-
?
dapsone + NADPH + O2

?
bioactivation by isozyme FMO3, not FMO1, results in covalent adduct formation
-
-
?
dapsone + NADPH + O2
?
isozyme FMO3, not FMO1
-
-
?
demeton-O + NADPH + O2

demeton-O sulfoxide + NADP+ + H2O
-
-
-
-
?
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
-
-
?
deprenyl + NADPH + H+ + O2
?
-
-
-
-
-
dibenzylamine + NADPH + O2

?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dibenzylamine + NADPH + O2
?
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2

methanesulfinate + NAD+ + H2O
-
-
-
-
?
dimethylsulfone + NADH + H+ + O2
methanesulfinate + NAD+ + H2O
-
-
-
-
?
disulfoton + NADPH + H+ + O2

?
-
-
-
-
?
disulfoton + NADPH + H+ + O2
?
a thioether-containing organophosphate insecticide
-
-
?
ephedrine + NADPH + O2

?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ephedrine + NADPH + O2
?
-
-
-
-
?
ethiofencarb + NADPH + O2

ethiofencarb sulfoxide + NADP+ + H2O
-
-
-
-
?
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
?
-
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2

ethionamide N-oxide + NADP+ + H2O
an antibiotic agent
-
-
?
ethionamide + NADPH + H+ + O2
ethionamide N-oxide + NADP+ + H2O
-
-
-
?
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 + 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
-
-
?
ethylene sulfide + NADPH + O2

?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
ethylene sulfide + NADPH + O2
?
-
-
-
-
?
fenthion + NADPH + O2

fenthion sulfoxide + NADP+ + H2O
-
-
-
-
?
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
-
-
?
imipramine + NADPH + O2

?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
liver microsomes
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
-
-
-
?
imipramine + NADPH + O2
?
-
liver isozyme FMO1
-
-
?
imipramine + NADPH + O2

imipramine N-oxide + NADP+ + H2O
-
-
-
-
?
imipramine + NADPH + O2
imipramine N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2

indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indole N-oxide + NADP+ + H2O
-
-
-
?
indole + NADPH + H+ + O2

indoxyl + NADP+ + H2O
-
-
-
-
?
indole + NADPH + H+ + O2
indoxyl + NADP+ + H2O
-
-
-
-
?
isopropylhydrazine + NADPH + O2

?
-
-
-
-
?
isopropylhydrazine + NADPH + O2
?
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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-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
-
-
?
lipoic acid + NADPH + O2

?
-
-
-
-
?
lipoic acid + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + H+ + O2

?
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + H+ + O2
?
-
a psychostimulant, is converted to the hydroxylamine
-
-
?
methamphetamine + NADPH + O2

?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
methamphetamine + NADPH + O2
?
-
-
-
-
?
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 + NADPH + H+ + O2
?
-
-
-
-
?
methimazole + NADPH + H+ + O2
?
-
FMO1, FMO2, and FMO3
-
-
?
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 N-oxide + NADP+ + H2O
-
-
-
-
?
methimazole + NADPH + H+ + O2

methimazole S-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

?
-
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
methimazole + NADPH + O2
?
-
-
-
-
?
methimazole + NADPH + O2
?
-
isozyme FMO3
-
-
?
methimazole + NADPH + O2
?
-
liver microsomes
-
-
?
methimazole + NADPH + O2
?
-
-
-
?
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
-
-
-
-
?
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

?
-
-
-
?
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
-
?
methylphenylsulfide + NADPH + O2

?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
methylphenylsulfide + NADPH + O2
?
-
-
-
-
?
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-aminohomopiperidine + NADPH + O2

?
-
-
-
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminohomopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminomorpholine + NADPH + O2

?
-
-
-
-
?
N-aminomorpholine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2

?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
?
-
-
-
-
?
N-aminopiperidine + NADPH + O2

tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
?
N-aminopiperidine + NADPH + O2
tetrazene + NADP+ + H2O + ?
-
-
-
-
?
N-aminopyrrolidone + NADPH + O2

?
-
-
-
-
?
N-aminopyrrolidone + NADPH + O2
?
-
-
-
-
?
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-chloro-N-methylaniline + NADPH + O2

?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
p-chloro-N-methylaniline + NADPH + O2
?
-
-
-
-
?
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
-
-
?
phenylhydrazine + NADPH + O2

?
-
-
-
-
?
phenylhydrazine + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2

?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2
?
-
-
-
-
?
phenylthiourea + NADPH + O2

phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
phenylthiourea + NADPH + O2
phenylthiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
procarbazine + NADPH + O2

?
-
-
-
-
?
procarbazine + NADPH + O2
?
-
-
-
-
?
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 + 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
-
-
?
sulfamethoxazole + NADPH + O2
?
isozyme FMO3, not FMO1
-
-
?
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
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
S-oxidation
-
-
?
sulindac sulfide + NADPH + H+ + O2
sulindac + NADP+ + H2O
-
-
-
?
tamoxifen + NADPH + H+ + O2

?
-
-
-
-
?
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

?
-
-
-
-
?
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
-
-
?
thioacetamide + NADPH + O2

?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thioacetamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2

?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiobenzamide + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2

?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + H+ + O2
?
-
-
-
-
?
thiourea + NADPH + O2

?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2
?
-
-
-
-
?
thiourea + NADPH + O2

thiourea S-oxide + NADP+ + H2O
-
isozyme FMO2
-
-
?
thiourea + NADPH + O2
thiourea S-oxide + NADP+ + H2O
-
-
-
-
?
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

?
-
-
-
-
?
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 + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
FMO1, no activity with FMO3 and FMO5
-
-
?
trimethylamine + NADPH + H+ + O2
?
-
-
-
-
?
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