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	ChemicalBook:CB8729604, eMolecules:480375, ZINC000000388188

Download	Molfile XML SDF

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Wikipedia	License
Metronidazole, sold under the brand name Flagyl among others, is an antibiotic and antiprotozoal medication. It is used either alone or with other antibiotics to treat pelvic inflammatory disease, endocarditis, and bacterial vaginosis. It is effective for dracunculiasis, giardiasis, trichomoniasis, and amebiasis. It is an option for a first episode of mild-to-moderate Clostridioides difficile colitis if vancomycin or fidaxomicin is unavailable. Metronidazole is available orally (by mouth), as a cream or gel, and by slow intravenous infusion (injection into a vein). Common side effects include nausea, a metallic taste, loss of appetite, and headaches. Occasionally seizures or allergies to the medication may occur. Some state that metronidazole should not be used in early pregnancy, while others state doses for trichomoniasis are safe. Metronidazole is generally considered compatible with breastfeeding. Metronidazole began to be commercially used in 1960 in France. It is on the World Health Organization's List of Essential Medicines. It is available in most areas of the world. In 2022, it was the 133rd most commonly prescribed medication in the United States, with more than 4 million prescriptions.
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Formula

C6H9N3O3

Net Charge

Average Mass

171.15400

Monoisotopic Mass

171.06439

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. antiamoebic agent An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae.

ChEBI Ontology
Outgoing	metronidazole (CHEBI:6909) has role antiamoebic agent (CHEBI:171664) 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

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

Citations

Last Modified

28 April 2021

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag