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Biological and Environmental Research Ontology
| Preferred Name | metronidazole | |
| Synonyms |
2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole metronidazol metronidazole 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole metronidazolum 2-methyl-5-nitroimidazole-1-ethanol 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol |
|
| 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 |
|
| alternative term |
2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole metronidazol metronidazole 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole metronidazolum 2-methyl-5-nitroimidazole-1-ethanol 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
|
|
| bearer of |
http://purl.obolibrary.org/obo/CHEBI_50685 http://purl.obolibrary.org/obo/CHEBI_35703 http://purl.obolibrary.org/obo/CHEBI_36047 http://purl.obolibrary.org/obo/CHEBI_132992 http://purl.obolibrary.org/obo/CHEBI_171664 |
|
| charge |
0
|
|
| database_cross_reference |
PMID:15739364 Wikipedia:Metronidazole PMID:22252819 KEGG:D00409 Beilstein:611683 PMID:11906111 PMID:14702395 HMDB:HMDB0015052 PMID:19485831 PMID:18397330 Drug_Central:1790 PDBeChem:2MN PMID:16901452 DrugBank:DB00916 PMID:22226009 LINCS:LSM-5628 Reaxys:611683 Patent:US2944061 PMID:16304169 CAS:443-48-1 VSDB:1826
|
|
| 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_alternative_id |
CHEBI:63636 CHEBI:39845
|
|
| has_exact_synonym |
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
|
|
| has_obo_namespace |
chebi_ontology
|
|
| has_related_synonym |
2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole metronidazol metronidazole 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole metronidazolum 2-methyl-5-nitroimidazole-1-ethanol 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole
|
|
| id |
CHEBI:6909
|
|
| in_subset | ||
| 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 | ||
| label |
metronidazole
|
|
| mass |
171.15400
|
|
| monoisotopicmass |
171.06439
|
|
| notation |
CHEBI:6909
|
|
| prefLabel |
metronidazole
|
|
| RO_0000087 |
http://purl.obolibrary.org/obo/CHEBI_50685 http://purl.obolibrary.org/obo/CHEBI_35703 http://purl.obolibrary.org/obo/CHEBI_36047 http://purl.obolibrary.org/obo/CHEBI_132992 http://purl.obolibrary.org/obo/CHEBI_171664 |
|
| smiles |
Cc1ncc(n1CCO)[N+]([O-])=O
|
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_24780 |
| Delete | Subject | Author | Type | Created |
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