Discuss This Drug

Metronidazole

CHEBI:CHEBI_6909

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.

Chemical Information

Molecular Formula
C6H9N3O3
Molecular Mass
171.15400
Charge
0
SMILES
Cc1ncc(n1CCO)[N+]([O-])=O
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

Alternative Names

  • 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
  • 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
  • metronidazol
  • metronidazole
  • metronidazolum

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
6922
oboInOwl#hasDbXref
Wikipedia:Metronidazole
core#notation
CHEBI:6909

Additional References

Wikipedia:Metronidazole

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

has_treatment
http://purl.obolibrary.org/obo/DOID_3767
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
6922
oboInOwl#hasDbXref
Wikipedia:Metronidazole
oboInOwl#hasAlternativeId
CHEBI:63636
oboInOwl#id
CHEBI:6909
core#notation
CHEBI:6909
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_50266
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
chebi#is_conjugate_base_of
http://purl.obolibrary.org/obo/CHEBI_64682
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect31217
chebi#is_conjugate_acid_of
http://purl.obolibrary.org/obo/CHEBI_64682
owl#someValuesFrom
t3009527
owl#annotatedSource
t276775