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Chemical Entities of Biological Interest Ontology
| Preferred Name | metronidazole | |
| Synonyms |
2-methyl-5-nitroimidazole-1-ethanol 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole metronidazole 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole metronidazol 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole metronidazolum 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 |
|
| charge |
0
|
|
| database_cross_reference |
PMID:11906111 HMDB:HMDB0015052 PMID:14702395 Drug_Central:1790 PMID:16304169 VSDB:1826 DrugBank:DB00916 LINCS:LSM-5628 PMID:15739364 CAS:443-48-1 PMID:16901452 PMID:18397330 PMID:22226009 PMID:19485831 Wikipedia:Metronidazole KEGG:D00409 PMID:22252819 PDBeChem:2MN Patent:US2944061 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_50685 http://purl.obolibrary.org/obo/CHEBI_35703 http://purl.obolibrary.org/obo/CHEBI_33281 http://purl.obolibrary.org/obo/CHEBI_36047 http://purl.obolibrary.org/obo/CHEBI_132992 http://purl.obolibrary.org/obo/CHEBI_171664 http://purl.obolibrary.org/obo/CHEBI_35442 |
|
| 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 |
2-methyl-5-nitroimidazole-1-ethanol 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole metronidazole 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole metronidazol 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole metronidazolum
|
|
| 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
|
|
| smiles |
Cc1ncc(n1CCO)[N+]([O-])=O
|
|
| treeView |
http://purl.obolibrary.org/obo/CHEBI_24780 |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_24780 |
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