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CHEBI:6909 - metronidazole

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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 C6H9N3O3
Net Charge 0
Average Mass 171.15400
Monoisotopic Mass 171.064
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
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): antitrichomonal drug
A drug used to treat trichomonas infections.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antiparasitic agent
A substance used to treat or prevent parasitic infections.
radiosensitizing agent
A drug that makes increases the sensitivity of tumour cells to radiation therapy.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing metronidazole (CHEBI:6909) has role antibacterial drug (CHEBI:36047)
metronidazole (CHEBI:6909) has role antimicrobial agent (CHEBI:33281)
metronidazole (CHEBI:6909) has role antiparasitic agent (CHEBI:35442)
metronidazole (CHEBI:6909) has role antitrichomonal drug (CHEBI:50685)
metronidazole (CHEBI:6909) has role environmental contaminant (CHEBI:78298)
metronidazole (CHEBI:6909) has role prodrug (CHEBI:50266)
metronidazole (CHEBI:6909) has role radiosensitizing agent (CHEBI:132992)
metronidazole (CHEBI:6909) has role xenobiotic (CHEBI:35703)
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
LSM-5628 LINCS
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 Beilstein Registry Number Beilstein
611683 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11906111 PubMed citation Europe PMC
14702395 PubMed citation Europe PMC
15739364 PubMed citation Europe PMC
16304169 PubMed citation Europe PMC
16901452 PubMed citation Europe PMC
18397330 PubMed citation Europe PMC
19485831 PubMed citation Europe PMC
22226009 PubMed citation Europe PMC
22252819 PubMed citation Europe PMC
Last Modified
11 August 2016