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metronidazole

Go to external page http://purl.obolibrary.org/obo/CHEBI_6909

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.

Term info

Label

metronidazole

Synonyms
  • 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
database cross reference
Subsets

3_STAR

IUPAC NAME
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol [ IUPAC ]

INN
metronidazole [ WHO_MedNet ]

INN
metronidazole [ KEGG_DRUG ]

INN
metronidazol [ WHO_MedNet ]

INN
metronidazolum [ WHO_MedNet ]

charge

0

formula

C6H9N3O3

has alternative id

CHEBI:63636, CHEBI:39845

has obo namespace

chebi_ontology

has related synonym

2-methyl-5-nitroimidazole-1-ethanol, 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole, 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole, 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole, 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole, 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole, metronidazole, 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole, metronidazol, metronidazolum, 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole

id

CHEBI:6909

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

mass

171.15400

monoisotopicmass

171.06439

smiles

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