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metronidazole (CHEBI:6909)

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ChEBI Name metronidazole
ChEBI ID 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:39845, CHEBI:63636
Supplier Information
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Formula Source
C6H9N3O3 ChEBI
Net Charge 0
Average Mass 171.15400
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
SMILES
Cc1ncc(n1CCO)[N+]([O-])=O
Roles Classification
Biological Role(s): antitrichomonal drug
A drug used to treat trichomonas infections.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antibiotic
A substance that is biostatic or biocidal at low concentrations towards bacteria, yeasts, moulds, or other form of life, especially pathogenic or noxious organisms. Although the term was originally restricted to substances produced by microorganisms, its use was later expanded to include derivatives of such substances and it is now commonly used to include entirely synthetic compounds.
Application(s): antitrichomonal drug
A drug used to treat trichomonas infections.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antibiotic
A substance that is biostatic or biocidal at low concentrations towards bacteria, yeasts, moulds, or other form of life, especially pathogenic or noxious organisms. Although the term was originally restricted to substances produced by microorganisms, its use was later expanded to include derivatives of such substances and it is now commonly used to include entirely synthetic compounds.
antiparasitic agent
A substance used to treat or prevent parasitic infections.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing metronidazole (CHEBI:6909) has role antibacterial drug (CHEBI:36047)
metronidazole (CHEBI:6909) has role antibiotic (CHEBI:22582)
metronidazole (CHEBI:6909) has role antiparasitic agent (CHEBI:35442)
metronidazole (CHEBI:6909) has role antitrichomonal drug (CHEBI:50685)
metronidazole (CHEBI:6909) has role photosensitizing agent (CHEBI:47868)
metronidazole (CHEBI:6909) has role prodrug (CHEBI:50266)
metronidazole (CHEBI:6909) is a C-nitro compound (CHEBI:35716)
metronidazole (CHEBI:6909) is a imidazoles (CHEBI:24780)
metronidazole (CHEBI:6909) is a primary alcohol (CHEBI:15734)
metronidazole (CHEBI:6909) is conjugate base of metronidazole(1+) (CHEBI:64682)
Incoming metronidazole benzoate (CHEBI:50688) has functional parent metronidazole (CHEBI:6909)
metronidazole(1+) (CHEBI:64682) is conjugate acid of metronidazole (CHEBI:6909)
IUPAC Name
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
INNs Sources
metronidazol WHO MedNet
metronidazole KEGG DRUG
métronidazole WHO MedNet
metronidazolum WHO MedNet
Synonyms Sources
1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole ChemIDplus
1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole ChemIDplus
1-(β-ethylol)-2-methyl-5-nitro-3-azapyrrole NIST Chemistry WebBook
1-(β-hydroxyethyl)-2-methyl-5-nitroimidazole ChemIDplus
1-(β-oxyethyl)-2-methyl-5-nitroimidazole ChemIDplus
2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole ChemIDplus
2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole ChemIDplus
2-methyl-5-nitroimidazole-1-ethanol ChemIDplus
Database Links Databases
2MN PDBeChem
D00409 KEGG DRUG
DB00916 DrugBank
HMDB15052 HMDB
Metronidazole Wikipedia
Metronidazole Wikipedia
US2944061 Patent
View more database links
Registry Numbers Types Sources
443-48-1 CAS Registry Number ChemIDplus
443-48-1 CAS Registry Number NIST Chemistry WebBook
611683 Reaxys Registry Number Reaxys
611683 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11906111 PubMed citation CiteXplore
14702395 PubMed citation CiteXplore
15739364 PubMed citation CiteXplore
16304169 PubMed citation CiteXplore
16901452 PubMed citation CiteXplore
18397330 PubMed citation CiteXplore
19485831 PubMed citation CiteXplore
22226009 PubMed citation CiteXplore
22252819 PubMed citation CiteXplore
Last Modified
03 March 2014

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