has role primary alcohol imidazoles antimicrobial agent C-nitro compound metronidazole 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole 171.064 171.15400 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole 2-methyl-5-nitroimidazole-1-ethanol 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. Beilstein:611683 C6H9N3O3 CAS:443-48-1 CHEBI:39845 CHEBI:63636 CHEBI:6909 Cc1ncc(n1CCO)[N+]([O-])=O DrugBank:DB00916 Drug_Central:1790 HMDB:HMDB0015052 InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 KEGG:D00409 LINCS:LSM-5628 PDBeChem:2MN PMID:11906111 PMID:14702395 PMID:15739364 PMID:16304169 PMID:16901452 PMID:18397330 PMID:19485831 PMID:22226009 PMID:22252819 Patent:US2944061 Reaxys:611683 VAOCPAMSLUNLGC-UHFFFAOYSA-N Wikipedia:Metronidazole chebi_ontology metronidazol metronidazole metronidazolum