Preferred Name

metronidazole

Synonyms

1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole

1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole

2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol

1-(beta-oxyethyl)-2-methyl-5-nitroimidazole

2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole

metronidazol

2-methyl-5-nitroimidazole-1-ethanol

metronidazole

2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole

1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole

1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole

metronidazolum

Definitions

A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.

ID

http://purl.obolibrary.org/obo/CHEBI_6909

charge

0

database_cross_reference

PMID:19485831

PMID:18397330

VSDB:1826

PDBeChem:2MN

HMDB:HMDB0015052

Wikipedia:Metronidazole

PMID:16304169

PMID:22252819

PMID:16901452

PMID:22226009

DrugBank:DB00916

Patent:US2944061

Beilstein:611683

LINCS:LSM-5628

Drug_Central:1790

PMID:15739364

PMID:11906111

KEGG:D00409

PMID:14702395

CAS:443-48-1

Reaxys:611683

definition

A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.

formula

C6H9N3O3

has role

http://purl.obolibrary.org/obo/CHEBI_33281

http://purl.obolibrary.org/obo/CHEBI_35703

http://purl.obolibrary.org/obo/CHEBI_36047

http://purl.obolibrary.org/obo/CHEBI_50266

http://purl.obolibrary.org/obo/CHEBI_50685

http://purl.obolibrary.org/obo/CHEBI_132992

http://purl.obolibrary.org/obo/CHEBI_35442

http://purl.obolibrary.org/obo/CHEBI_78298

has_alternative_id

CHEBI:39845

CHEBI:63636

has_exact_synonym

2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol

has_obo_namespace

chebi_ontology

has_related_synonym

1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole

1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole

1-(beta-oxyethyl)-2-methyl-5-nitroimidazole

2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole

metronidazol

2-methyl-5-nitroimidazole-1-ethanol

metronidazole

2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole

1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole

1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole

metronidazolum

id

CHEBI:6909

in_subset

http://purl.obolibrary.org/obo/chebi#3_STAR

inchi

InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

inchikey

VAOCPAMSLUNLGC-UHFFFAOYSA-N

is conjugate base of

http://purl.obolibrary.org/obo/CHEBI_64682

label

metronidazole

mass

171.15400

monoisotopicmass

171.06439

notation

CHEBI:6909

prefLabel

metronidazole

smiles

Cc1ncc(n1CCO)[N+]([O-])=O

treeView

http://purl.obolibrary.org/obo/CHEBI_35716

http://purl.obolibrary.org/obo/CHEBI_24780

http://purl.obolibrary.org/obo/CHEBI_15734

subClassOf

http://purl.obolibrary.org/obo/CHEBI_35716

http://purl.obolibrary.org/obo/CHEBI_24780

http://purl.obolibrary.org/obo/CHEBI_15734

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http://purl.bioontology.org/ontology/RXNORM/6922 RXNORM LOOM
http://purl.obolibrary.org/obo/ARO_3000689 ARO LOOM
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http://purl.obolibrary.org/obo/CHEBI_6909 DINTO LOOM
http://purl.obolibrary.org/obo/CHEBI_6909 DINTO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_6909 DRON LOOM
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http://purl.obolibrary.org/obo/CHEBI_6909 GENEPIO LOOM
http://purl.obolibrary.org/obo/CHEBI_6909 GENEPIO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_6909 NIFSTD LOOM
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http://ncicb.nci.nih.gov/xml/owl/EVS/Thesaurus.owl#C651 NCIT LOOM
http://www.co-ode.org/ontologies/galen#Metronidazole GALEN LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#D008795 RH-MESH LOOM
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http://purl.bioontology.org/ontology/UATC/D06BX01 ATC LOOM
http://sbmi.uth.tmc.edu/ontology/ochv#8073 OCHV LOOM
http://purl.bioontology.org/ontology/CSP/1549-4919 CRISP LOOM
http://purl.bioontology.org/ontology/SNMI/C-52040 SNMI LOOM
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http://purl.jp/bio/4/id/200906013134576937 IOBC LOOM
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http://purl.bioontology.org/ontology/UATC/J01XD01 ATC LOOM
http://purl.bioontology.org/ontology/MESH/D008795 MESH LOOM