Information on EC 1.14.14.73 - albendazole monooxygenase (sulfoxide-forming)

for references in articles please use BRENDA:EC1.14.14.73
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.14.73
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RECOMMENDED NAME
GeneOntology No.
albendazole monooxygenase (sulfoxide-forming)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
albendazole + [reduced NADPH-hemoprotein reductase] + O2 = albendazole S-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1)
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fenbendazole + [reduced NADPH-hemoprotein reductase] + O2 = fenbendazole S-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(2)
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SYSTEMATIC NAME
IUBMB Comments
albendazole,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (sulfoxide-forming)
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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metabolism of albendazole to albendazole-sulfoxide by pig liver microsomes is dependent on both microsomal cytochrome P-450 and FAD-containing mono-oxygenase enzymes. the relative contributions of the two systems depend on the concentration of albendazole
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
albendazole + [reduced NADPH-hemoprotein reductase] + O2
albendazole S-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
amiodarone + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
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?
astemizole + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
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?
cyclosporine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
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?
danazol + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
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?
fenbendazole + [reduced NADPH-hemoprotein reductase] + O2
fenbendazole S-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
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?
mesoridazine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
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?
thioridazine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
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?
additional information
?
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enzyme is able to modify antihistamine drugs such as albendazole, amiodarone, astemizole, thioridazine, mesoridazine, and danazol. The substrates vary in size and overall topology from relatively rigid structures (amiodarone) to larger complex structures (cyclosporine). CYP2J2 metabolism is more restrictive than that of YP3A4 and limited, in general, to a single site for large compounds
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
albendazole + [reduced NADPH-hemoprotein reductase] + O2
albendazole S-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
P51589
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?
fenbendazole + [reduced NADPH-hemoprotein reductase] + O2
fenbendazole S-oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
P51589
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
clotrimazole
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ketoconazole
0.5-1 microM, 32% inhibition
ritonavir
0.5-1 microM, 34% inhibition
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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in bile of albendazole-treated animals, only albendazole S-oxide, but not the sulfone, is present
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
homology modeling of structure
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
cytochrome P-450c is induced potently in vivo by albendazole
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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enzyme is able to modify antihistamine drugs such as albendazole, amiodarone, astemizole, thioridazine, mesoridazine, and danazol with in vitro intrinsic clearance values ranging from 0.06 to 3.98 microl/min/pmol CYP2J2. Whereas isoform CYP3A4 commonly metabolizes compounds at multiple sites, CYP2J2 metabolism is more restrictive and limited, in general, to a single site for large compounds