Ligand metronidazole

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Basic Ligand Information

Molecular Structure
Picture of metronidazole (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H9N3O3
metronidazole
VAOCPAMSLUNLGC-UHFFFAOYSA-N
Synonyms:
nidazole, oxidized metranidazole, oxidized metronidazole

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
metronidazole + NADPH + H+ = ? + NADP+
show the reaction diagram
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H2 + ferredoxin + oxidized metronidazole = H+ + ferredoxin + reduced metronidazole
show the reaction diagram
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H2 + oxidized metranidazole = H+ + reduced metranidazol
show the reaction diagram
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oxalate + metronidazole = CO2 + reduced metronidazole
show the reaction diagram
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metronidazole + NADP+ = ? + NADPH
show the reaction diagram
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reduced coenzyme F420 + oxidized metronidazole = oxidized coenzyme F420 + reduced metronidazole
show the reaction diagram
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coenzyme B-coenzyme M disulfide + metronidazole + 2 H2 = coenzyme B + coenzyme M + reduced metronidazole2- + 2 H+
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Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
reduced metronidazole + CoB + CoM + H+ = H2 + oxidized metronidazole + CoM-S-S-CoB
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
68% enhancement of activity
-
4fold stimulation at a concentration of 0.032 mg/ml
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Inhibitor in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
noncompetitive
-
26% inhibition at a concentration of 0.032 mg/ml
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metronidazole-modified recombinant enzyme displays considerably reduced thioredoxin reductase activity. By reducing metronidazole, the enzyme renders itself and associated thiol-containing proteins vulnerable to adduct formation
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irreversible inactivation mechanism, the thiuram compounds can circumvent the resistance mechanism that renders metronidazole ineffectiveness in drug resistance cases of giardiasis
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.6
-
pH 7.5, 37C

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0224
-
pH 7.5, 37C

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.57
-
25C, pH 8.0
1.178
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25C, pH 8.5

IC50 Value (4 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.23
-
25C, pH 8.0
1.15
-
25C, pH 8.5
0.0019
-
at pH 7.5 and 25C
0.00072
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pH not specified in the publication, temperature not specified in the publication

References & Links

Links to other databases for metronidazole

ChEBI
PubChem
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PubChem