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Information on EC 1.14.13.32 - albendazole monooxygenase
for references in articles please use BRENDA:EC1.14.13.32
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
1.14.13.32 albendazole monooxygenase
IUBMB Comments
A microsomal flavin-containing monooxygenase. A similar conversion is also carried out by some microsomal cytochrome P-450 enzymes [EC 1.14.14.73, albendazole monooxygenase (sulfoxide-forming)]. It is estimated that cytochrome P-450s are responsible for 70% of the activity.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
showSynonyms
albendazole sulfoxidase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
albendazole oxidase
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-
-
-
albendazole sulfoxidase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
albendazole + NADPH + H+ + O2 = albendazole S-oxide + NADP+ + H2O
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
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 microsomal flavin-containing monooxygenase. A similar conversion is also carried out by some microsomal cytochrome P-450 enzymes [EC 1.14.14.73, albendazole monooxygenase (sulfoxide-forming)]. It is estimated that cytochrome P-450s are responsible for 70% of the activity.
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CAS REGISTRY NUMBER
COMMENTARY
101299-59-6
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 albendazole + 2 NADPH + 2 H+ + 2 O2
(+)-albendazole s-oxide + (-)-albendazole s-oxide + 2 NADP+ + 2 H2O
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
albendazole S-oxide + NADP+ + H2O
albendazole + NADPH + H+ + O2
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Substrates: -
Products: -
Products: -
r
additional information
?
-
-
Substrates: intestinal bioconversion of the anthelmintic drug albendazole into albendazole sulfoxide by two enzymatic systems, cytochrome P4503A and flavin-containing monooxygenases, overview
Products: -
Products: -
?
2 albendazole + 2 NADPH + 2 H+ + 2 O2
(+)-albendazole s-oxide + (-)-albendazole s-oxide + 2 NADP+ + 2 H2O
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Substrates: -
Products: -
Products: -
?
2 albendazole + 2 NADPH + 2 H+ + 2 O2
(+)-albendazole s-oxide + (-)-albendazole s-oxide + 2 NADP+ + 2 H2O
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Substrates: in vitro, 0.1 M sodium phosphate buffer, pH 7.4, 37°C, ex vivo, cultivation (48 h) of animals in phosphate buffered saline, pH 7.4, 38°C
Products: -
Products: -
?
albendazole + NADPH + O2
(+)-albendazole S-oxide + NADP+
-
Substrates: -
Products: 100% enantioselective towards the (+)-albendazole S-oxide
Products: 100% enantioselective towards the (+)-albendazole S-oxide
?
albendazole + NADPH + O2
(+)-albendazole S-oxide + NADP+
-
Substrates: -
Products: 100% enantioselective towards the (+)-albendazole S-oxide
Products: 100% enantioselective towards the (+)-albendazole S-oxide
?
albendazole + NADPH + O2
albendazole S-oxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
albendazole + NADPH + O2
albendazole S-oxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 albendazole + 2 NADPH + 2 H+ + 2 O2
(+)-albendazole s-oxide + (-)-albendazole s-oxide + 2 NADP+ + 2 H2O
-
Substrates: -
Products: -
Products: -
?
albendazole + NADPH + H+ + O2
albendazole S-oxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: intestinal bioconversion of the anthelmintic drug albendazole into albendazole sulfoxide by two enzymatic systems, cytochrome P4503A and flavin-containing monooxygenases, overview
Products: -
Products: -
?
albendazole + NADPH + O2
albendazole S-oxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
albendazole + NADPH + O2
albendazole S-oxide + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Methimazole
-
competitive inhibitor, thermal treatment of the microsomes inhibited the methimazole oxidation
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0015
albendazole S-oxide
-
mitochondrial fraction in vitro, pH 7.4, 37°C
additional information
albendazole S-oxide
-
no formation of albendazole sulfone in the microsomal fraction in vitro, pH 7.4, 37°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
lancet fluke, isolated from naturally infected mouflon ewes (Ovis musimon)
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-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
-
in situ enzyme assays, histochemic analysis, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
2 min. 50°C in assay buffer in the absence of NADPH inactivates the enzyme
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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
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
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Fargetton, X.; Galtier, P.; Delatour, P.
Sulfoxidation of albendazole by a cytochrome P450-independent monooxygenase from rat liver microsomes
Vet. Res. Commun.
10
317-324
1986
Rattus norvegicus, Sus scrofa
brenda
Moroni, P.; Buronfosse, T.; Longin-Sauvageon, C.; Delatour, P.; Benoit, E.
Chiral sulfoxidation of albendazole by the flavin adenine dinucleotide-containing and cytochrome P450-dependent monooxygenases from rat liver microsomes
Drug Metab. Dispos.
23
160-165
1995
Rattus norvegicus
brenda
Virkel, G.; Lifschitz, A.; Sallovitz, J.; Pis, A.; Lanusse, C.
Comparative hepatic and extrahepatic enantioselective sulfoxidation of albendazole and fenbendazole in sheep and cattle
Drug Metab. Dispos.
32
536-544
2004
Bos taurus, Ovis aries
brenda
Molina, A.J.; Merino, G.; Prieto, J.G.; Real, R.; Mendoza, G.; Alvarez, A.I.
Absorption and metabolism of albendazole after intestinal ischemia/reperfusion
Eur. J. Pharm. Sci.
31
16-24
2007
Rattus norvegicus
brenda
Cvilink, V.; Szotakova, B.; Krizova, V.; Lamka, J.; Skalova, L.
Phase I biotransformation of albendazole in lancet fluke (Dicrocoelium dendriticum)
Res. Vet. Sci.
86
49-55
2009
Dicrocoelium dendriticum
brenda
EXTERNAL LINKS (specific for EC-Number 1.14.13.32)
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Release 2023.1 (January 2023)
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