Information on EC 1.14.13.32 - albendazole monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.32
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RECOMMENDED NAME
GeneOntology No.
albendazole monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
albendazole + NADPH + H+ + O2 = albendazole S-oxide + NADP+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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sulfoxidation
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SYSTEMATIC NAME
IUBMB Comments
albendazole,NADPH:oxygen oxidoreductase (sulfoxide-forming)
A flavoprotein (FAD).
CAS REGISTRY NUMBER
COMMENTARY hide
101299-59-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
lancet fluke, isolated from naturally infected mouflon ewes (Ovis musimon)
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 albendazole + 2 NADPH + 2 H+ + 2 O2
(+)-albendazole s-oxide + (-)-albendazole s-oxide + 2 NADP+ + 2 H2O
show the reaction diagram
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
show the reaction diagram
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-
-
-
?
albendazole + NADPH + O2
(+)-albendazole S-oxide + NADP+
show the reaction diagram
albendazole + NADPH + O2
albendazole S-oxide + NADP+ + H2O
show the reaction diagram
additional information
?
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intestinal bioconversion of the anthelmintic drug albendazole into albendazole sulfoxide by two enzymatic systems, cytochrome P4503A and flavin-containing monooxygenases, overview
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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
2 albendazole + 2 NADPH + 2 H+ + 2 O2
(+)-albendazole s-oxide + (-)-albendazole s-oxide + 2 NADP+ + 2 H2O
show the reaction diagram
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-
-
-
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
albendazole + NADPH + O2
albendazole S-oxide + NADP+ + H2O
show the reaction diagram
additional information
?
-
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intestinal bioconversion of the anthelmintic drug albendazole into albendazole sulfoxide by two enzymatic systems, cytochrome P4503A and flavin-containing monooxygenases, overview
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
NADPH
additional information
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no metabolites are formed with NADH
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Methimazole
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competitive inhibitor, thermal treatment of the microsomes inhibited the methimazole oxidation
thiobenzamide
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Tranylcypromine
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competitive inhibitor
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0047 - 0.0536
Albendazole
0.0015
albendazole S-oxide
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mitochondrial fraction in vitro, pH 7.4, 37C
additional information
albendazole S-oxide
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no formation of albendazole sulfone in the microsomal fraction in vitro, pH 7.4, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000237
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microsomal fraction in vitro, pH 7.4, 37C
0.000052
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mitochondrial fraction in vitro, pH 7.4, 37C
additional information
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in situ activity in the intestine
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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assay conditions
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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in situ enzyme assays, histochemic analysis, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
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no reaction in cytosol fraction
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
59000
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SDS-PAGE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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2 min. 50C in assay buffer in the absence of NADPH inactivates the enzyme
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Dicrocoelium dendriticum adults are washed and homogenized in 0.1 M sodium phosphate buffer, pH 7.4, with Potter-Elvehjem homogenizer and sonicator, ultracentrifugation separates mitochondrial fraction (resuspended in 0.1 M sodium phosphate buffer, pH 7.4) from microsome fraction (resuspended in the same buffer containing 20% glycerol), and cytosol fraction
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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albendazole as an anthelmintic drug is an important tool for the control of lancet fluke infections in small ruminants