CHEBI:6909 - metronidazole

ChEBI IDCHEBI:6909
ChEBI Namemetronidazole
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:39845, CHEBI:63636
Last Modified28 April 2021
DownloadsMolfile
FormulaC6H9N3O3
Net Charge0
Average Mass171.156
Monoisotopic Mass171.06439
SMILESCc1ncc([N+](=O)[O-])n1CCO
InChIInChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
InChIKeyVAOCPAMSLUNLGC-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Roles:
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
antibacterial drug  A drug used to treat or prevent bacterial infections.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antitrichomonal drug  A drug used to treat trichomonas infections.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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.
Applications:
antiparasitic agent  A substance used to treat or prevent parasitic infections.
antiamoebic agent  An antiparasitic agent which is effective against amoeba, a genus of single-celled amoeboids in the family Amoebidae.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
anti-ulcer drug  One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
antibacterial drug  A drug used to treat or prevent bacterial 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.
antitrichomonal drug  A drug used to treat trichomonas infections.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
radiosensitizing agent  A drug that makes increases the sensitivity of tumour cells to radiation therapy.
ChEBI Ontology
Outgoing Relation(s)
metronidazole (CHEBI:6909) has role analgesic (CHEBI:35480)
metronidazole (CHEBI:6909) has role anti-HIV agent (CHEBI:64946)
metronidazole (CHEBI:6909) has role anti-inflammatory agent (CHEBI:67079)
metronidazole (CHEBI:6909) has role anti-ulcer drug (CHEBI:49201)
metronidazole (CHEBI:6909) has role antiamoebic agent (CHEBI:171664)
metronidazole (CHEBI:6909) has role antibacterial agent (CHEBI:33282)
metronidazole (CHEBI:6909) has role antibacterial drug (CHEBI:36047)
metronidazole (CHEBI:6909) has role antifungal agent (CHEBI:35718)
metronidazole (CHEBI:6909) has role antifungal drug (CHEBI:86327)
metronidazole (CHEBI:6909) has role antiinfective agent (CHEBI:35441)
metronidazole (CHEBI:6909) has role antimicrobial agent (CHEBI:33281)
metronidazole (CHEBI:6909) has role antimicrobial agent (CHEBI:33281)
metronidazole (CHEBI:6909) has role antineoplastic agent (CHEBI:35610)
metronidazole (CHEBI:6909) has role antiparasitic agent (CHEBI:35442)
metronidazole (CHEBI:6909) has role antitrichomonal drug (CHEBI:50685)
metronidazole (CHEBI:6909) has role antitubercular agent (CHEBI:33231)
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 Relation(s)
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  Source
metronidazolWHO MedNet
metronidazoleKEGG DRUG
métronidazoleWHO MedNet
metronidazolumWHO MedNet
Synonyms  Source
1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazoleChemIDplus
1-(2-hydroxyethyl)-2-methyl-5-nitroimidazoleChemIDplus
1-(β-ethylol)-2-methyl-5-nitro-3-azapyrroleNIST Chemistry WebBook
1-(β-hydroxyethyl)-2-methyl-5-nitroimidazoleChemIDplus
1-(β-oxyethyl)-2-methyl-5-nitroimidazoleChemIDplus
2-methyl-1-(2-hydroxyethyl)-5-nitroimidazoleChemIDplus
Brand Names  Source
AnabactChEMBL
DrazifonChEMBL
Flagyl 375ChEMBL
Flagyl-400ChEMBL
Flagyl compakChEMBL
Flagyl erChEMBL
Manual XrefsDatabases
1790DrugCentral
1826VSDB
2MNPDBeChem
D00409KEGG DRUG
DB00916DrugBank
HMDB0015052HMDB
LSM-5628LINCS
MetronidazoleWikipedia
US2944061Patent
Registry NumbersSources
Reaxys:611683Reaxys
CAS:443-48-1ChemIDplus
CAS:443-48-1NIST Chemistry WebBook
Citations