has role radiosensitizing agent primary alcohol antiamoebic agent imidazoles xenobiotic C-nitro compound antibacterial drug prodrug antitrichomonal drug metronidazole(1+) metronidazole VAOCPAMSLUNLGC-UHFFFAOYSA-N PMID:11906111 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole C6H9N3O3 LINCS:LSM-5628 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole chebi_ontology Beilstein:611683 PMID:16901452 KEGG:D00409 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole CAS:443-48-1 InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol PMID:16304169 CHEBI:63636 PMID:15739364 PMID:18397330 CHEBI:39845 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole PMID:14702395 0 PDBeChem:2MN metronidazol PMID:22252819 Wikipedia:Metronidazole CHEBI:6909 VSDB:1826 PMID:19485831 Reaxys:611683 Cc1ncc(n1CCO)[N+]([O-])=O 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole metronidazole Patent:US2944061 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole PMID:22226009 171.06439 2-methyl-5-nitroimidazole-1-ethanol 171.15400 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. Drug_Central:1790 DrugBank:DB00916 HMDB:HMDB0015052 metronidazolum environmental contaminant