U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H9N3O3
Molecular Weight 171.154
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METRONIDAZOLE

SMILES

CC1=NC=C(N1CCO)[N+]([O-])=O

InChI

InChIKey=VAOCPAMSLUNLGC-UHFFFAOYSA-N
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

HIDE SMILES / InChI

Description

Metronidazole was synthesized by France's Rhone-Poulenc laboratories and introduced in the mid-1950s under the brand name Flagel in the US, while Sanofi-Aventis markets metronidazole globally under the same trade name, Flagyl, and also by various generic manufacturers. Metronidazole is one of the rare examples of a drug developed as ant parasitic, which has since gained broad use as an antibacterial agent. Metronidazole, a nitroimidazole, exerts antibacterial effects in an anaerobic environment against most obligate anaerobes. Metronidazole is indicated for the treatment of the following infections due to susceptible strains of sensitive organisms: Trichomoniasis: symptomatic, asymptomatic, asymptomatic consorts; Amebiasis: acute intestinal amebiasis (amebic dysentery) and amebic liver abscess; Anaerobic bacterial infections; Intra-abdominal infections, including peritonitis, intra-abdominal abscess, and liver abscess; Skin and skin structure infections; Gynecologic infections, including endometritis, endomyometritis, tubo-ovarian abscess, and postsurgical vaginal cuff infection; Bacterial septicemia; Bone and joint infections, as adjunctive therapy; Central Nervous System infections, including meningitis and brain abscess; Lower Respiratory Tract infections, including pneumonia, empyema, and lung abscess; Endocarditis. Metronidazole is NOT effective for infections caused by aerobic bacteria that can survive in the presence of oxygen. Metronidazole is only effective against anaerobic bacterial infections because the presence of oxygen will inhibit the nitrogen-reduction process that is crucial to the drug's mechanism of action. Once metronidazole enters the organism by passive diffusion and activated in the cytoplasm of susceptible anaerobic bacteria, it is reduced; this process includes intracellular electron transport proteins such as ferredoxin, transfer of an electron to the nitro group of the metronidazole, and formation of a short-lived nitroso free radical. Because of this alteration of the metronidazole molecule, a concentration gradient is created and maintained which promotes the drug’s intracellular transport. The reduced form of metronidazole and free radicals can interact with DNA leading to inhibition of DNA synthesis and DNA degradation leading to death of the bacteria. The precise mechanism of action of metronidazole is unknown. Metronidazole has a limited spectrum of activity that encompasses various protozoans and most Gram-negative and Gram-positive anaerobic bacteria. Metronidazole has activity against protozoans like Entamoeba histolytica, Giardia lamblia and Trichomonas vaginalis, for which the drug was first approved as an effective treatment.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants.
1992
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Metronidazole induced acute confusional agitated state.
2000 Feb
A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis.
2000 Jun 22
Concordance between genetic relatedness and phenotypic similarities of Trichomonas vaginalis strains.
2001
[Pneumatosis cystoides intestinalis: the first case in Congo].
2001 Apr-Jun
Technology evaluation: CEA-TRICOM, Therion Biologics Corp.
2001 Aug
[Diagnostic, therapeutic and prognostic aspects of intestinal typhoid perforations in children of Abidjan, Côte d'Ivoire].
2001 Dec
Enhanced activation of rhesus T cells by vectors encoding a triad of costimulatory molecules (B7-1, ICAM-1, LFA-3).
2001 Dec 12
Clinical onset of the Crohn's disease after eradication therapy of Helicobacter pylori infection. Does Helicobacter pylori infection interact with natural history of inflammatory bowel diseases?
2001 Jan-Feb
Enhancing the potency of peptide-pulsed antigen presenting cells by vector-driven hyperexpression of a triad of costimulatory molecules.
2001 May 14
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Metronidazole-induced encephalopathy in a uremic patient: a case report.
2001 Sep
Validation of a method for the detection and confirmation of nitroimidazoles and corresponding hydroxy metabolites in turkey and swine muscle by means of gas chromatography-negative ion chemical ionization mass spectrometry.
2001 Sep 15
[Treatment of bacterial vaginosis with high dosage metronidazole and lactic acid].
2002
Vaccine-based therapy directed against carcinoembryonic antigen demonstrates antitumor activity on spontaneous intestinal tumors in the absence of autoimmunity.
2002 Dec 1
[Comparative study of combined local treatment (sulfadimidine, metronidazole and nystatin) and the standard monotherapy in uncomplicated bacterial vaginosis].
2002 Dec 22
Allergic contact dermatitis from 2-bromo-2-nitropropane-1,3-diol in Metrogel.
2002 Jan
Reversible metronidazole-induced lesions of the cerebellar dentate nuclei.
2002 Jan 3
Metronidazol as a probable cause of severe liver injury.
2002 Jan-Feb
[Antibiotic prophylaxys in pediatric surgery of genito-urinary abnormalities].
2002 Jun
Lack of disulfiram-like reaction with metronidazole and ethanol.
2002 Jun
Effectiveness of metronidazole gel on cyclosporine-induced gingival overgrowth in heart transplant patients.
2002 Mar
[Antiamebic effect of metronidazole proved in a study conducted in Cienfuegos province].
2002 May-Aug
[Microbiologic characteristics of wound infectious process in use of ion-exchange sorbents].
2003
[Anaerobic bacteria in bronchoalveolar lavage fluid (BAL) after thoracic surgery].
2003
Metronidazole and mental confusion.
2003 Apr
Antitumor immunity after vaccination with B lymphoma cells overexpressing a triad of costimulatory molecules.
2003 Apr 2
Renal papillary necrosis induced by naproxen.
2003 Aug
Metronidazole-induced encephalopathy and inferior olivary hypertrophy: lesion analysis with diffusion-weighted imaging and apparent diffusion coefficient maps.
2003 Dec
Solvent effects in permeation assessed in vivo by skin surface biopsy.
2003 Dec 18
Role of bacteria and inducible nitric oxide synthase activity in the systemic inflammatory microvascular response provoked by indomethacin in the rat.
2003 Feb 7
Penetration of capecitabine and its metabolites into malignant and healthy tissues of patients with advanced breast cancer.
2003 Mar 10
Diazepam as a treatment for metronidazole toxicosis in dogs: a retrospective study of 21 cases.
2003 May-Jun
A comparison of 15% azelaic acid gel and 0.75% metronidazole gel in the topical treatment of papulopustular rosacea: results of a randomized trial.
2003 Nov
Modified vaccinia virus ankara recombinants are as potent as vaccinia recombinants in diversified prime and boost vaccine regimens to elicit therapeutic antitumor responses.
2003 Nov 15
Ruthenium(II) sulfoxide-maltolato and -nitroimidazole complexes: synthesis and MTT assay.
2003 Nov 17
Cardiac diphtheria in a previously immunized individual.
2003 Sep
Crohn's disease--when to operate?
2004
[Clinical analysis of unsuccessful Helicobacter pylori eradication].
2004
[Efficacy of two Helicobacter pylori eradication treatments in children with recurrent abdominal pain].
2004 Apr-Jun
Nitazoxanide: a new broad spectrum antiparasitic agent.
2004 Feb
A case of clarithromycin-induced manic episode (antibiomania).
2004 Mar
Metronidazole-induced encephalopathy.
2004 Sep 15
Phase I study of sequential vaccinations with fowlpox-CEA(6D)-TRICOM alone and sequentially with vaccinia-CEA(6D)-TRICOM, with and without granulocyte-macrophage colony-stimulating factor, in patients with carcinoembryonic antigen-expressing carcinomas.
2005 Feb 1
Analyses of recombinant vaccinia and fowlpox vaccine vectors expressing transgenes for two human tumor antigens and three human costimulatory molecules.
2005 Feb 15
Is operative management effective in treatment of perforated typhoid?
2005 Mar
[Two cases of metronidazole-induced encephalopathy].
2005 Mar
Abnormal enhancing lesion of dentate nuclei causing neurologic symptoms induced by metronidazole toxicity.
2005 Mar
Can antibiotics prevent preterm birth--the pro and con debate.
2005 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Trichomoniasis: In the Female: One-day treatment − two grams of FLAGYL, given ither as a single dose or in two divided doses of one gram each, given in the same day. Anaerobic Bacterial Infections: In the treatment of most serious anaerobic infections, intravenous metronidazole is usually administered initially. The usual adult oral dosage is 7.5 mg/kg every six hours (approx. 500 mg for a 70-kg adult). A maximum of 4 g should not be exceeded during a 24-hour period. Amebiasis: Adults: For acute intestinal amebiasis (acute amebic dysentery): 750 mg orally three times daily for 5 to 10 days. For amebic liver abscess: 500 mg or 750 mg orally three times daily for 5 to 10 days. Pediatric patients: 35 to 50 mg/kg/24 hours, divided into three doses, orally for 10 days.
Route of Administration: oral, intravenous
In Vitro Use Guide
Cells incubated with lethal drug (Metronidazole (MTZ)) concentration exhibit unchanged DNA profile, only about 50% of cells are positive for γH2A and lose an ability to attach to a surface after few hours of incubation. It is likely that the early reaction of cells to lethal concentration of MTZ is not primarily initiated by the reaction to DNA damage but rather by the immediate interaction of MTZ with biomolecules where activated MTZ is generated.
Name Type Language
METRONIDAZOLE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
METRONIDAZOLE COMPONENT OF HELIDAC
Common Name English
METRONIDAZOLE [WHO-IP]
Common Name English
VANDAZOLE
Brand Name English
METROMIDOL
Brand Name English
FLAGYL
Brand Name English
1H-IMIDAZOLE-1-ETHANOL, 2-METHYL-5-NITRO-
Systematic Name English
NSC-50364
Code English
METRONIDAZOLE COMPONENT OF PYLERA
Common Name English
BAYER 5360
Code English
METRONIDAZOLE [IARC]
Common Name English
METRONIDAZOLE [USAN]
Common Name English
PYLERA COMPONENT METRONIDAZOLE
Common Name English
METROGEL
Brand Name English
METRONIDAZOLE [MI]
Common Name English
DEFLAMON
Common Name English
METRONIDAZOLE [HSDB]
Common Name English
SATRIC
Brand Name English
2-METHYL-5-NITROIMIDAZOLE-1-ETHANOL
Systematic Name English
HELIDAC COMPONENT METRONIDAZOLE
Common Name English
METRONIDAZOLE [INN]
Common Name English
RP 8823
Code English
METRONIDAZOLE [VANDF]
Common Name English
METRONIDAZOLE [USP]
Common Name English
RP-8823
Code English
METRONIDAZOLE [USP-RS]
Common Name English
METRO I.V.
Brand Name English
BAYER-5360
Code English
PROTOSTAT
Brand Name English
METRONIDAZOLE [ORANGE BOOK]
Common Name English
METRONIDAZOLE [JAN]
Common Name English
ORVAGIL
Common Name English
NORITATE
Brand Name English
METROLOTION
Brand Name English
METROCREAM
Brand Name English
METROGEL-VAGINAL
Brand Name English
GINEFLAVIR
Common Name English
METRONIDAZOLE [WHO-DD]
Common Name English
ZADSTAT
Common Name English
METRONIDAZOLE [MART.]
Common Name English
NSC-69587
Code English
METRONIDAZOLUM [WHO-IP LATIN]
Common Name English
METRONIDAZOLE [EP]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 6.5.1
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QA02BD02
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
NDF-RT N0000175435
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC P01AB01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QG01AF01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC J01XD01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC A02BD01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC J01RA10
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC G01AF01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC A02BD03
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC D06BX01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC A02BD11
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC J01RA04
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
LIVERTOX 632
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
CFR 21 CFR 530.41
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 17486
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QP51AA01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QA02BD03
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
NCI_THESAURUS C279
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
EU-Orphan Drug EU/3/11/875
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 267008
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
EPA PESTICIDE CODE 120401
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC P01AB51
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC A02BD02
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 339111
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC J01RA03
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC A02BD08
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QD06BX01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 247907
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 21687
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QJ01XD01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 514715
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
NDF-RT N0000007663
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QA01AB17
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
FDA ORPHAN DRUG 61891
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QA02BD08
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
NDF-RT N0000007663
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-VATC QA02BD01
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
WHO-ATC A01AB17
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
207-136-1
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
PUBCHEM
4173
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
INN
1032
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
CAS
443-48-1
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
NCI_THESAURUS
C651
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
EPA CompTox
443-48-1
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
MESH
D008795
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METRONIDAZOLE
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY Description: A white or pale yellow, crystalline powder; odourless or almost odourless.Solubility: Sparingly soluble in water; slightly soluble in ethanol (~750 g/l) TS and ether R.Category: Antitrichomonal; antiamoebic. Storage: Metronidazole should be kept in a well-closed container, protected from light. Additional information: Metronidazole is stable in air, but darkens on exposure to light. Definition: Metronidazole contains not less than 99.0% and not more than 101.0% of C6H9N3O3, calculated with reference to the dried substance.
EVMPD
SUB08922MIG
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
ChEMBL
CHEMBL137
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
RXCUI
6922
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY RxNorm
LactMed
443-48-1
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
HSDB
443-48-1
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
MERCK INDEX
M7506
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
METRONIDAZOLE
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY
DRUG BANK
DB00916
Created by admin on Mon Oct 21 19:48:13 UTC 2019 , Edited by admin on Mon Oct 21 19:48:13 UTC 2019
PRIMARY