Home Imidazoles 3034-38-6
3034-38-6,MFCD00005196
Catalog No.:AA002ZQO

3034-38-6 | 4-Nitroimidazole

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5g
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002ZQO
Chemical Name:
4-Nitroimidazole
CAS Number:
3034-38-6
Molecular Formula:
C3H3N3O2
Molecular Weight:
113.0748
MDL Number:
MFCD00005196
SMILES:
[O-][N+](=O)c1cnc[nH]1
NSC Number:
50359
Properties
Properties
 
BP:
404.8°C at 760 mmHg  
Form:
Solid  
MP:
303 °C (dec.);(lit.);  
Refractive Index:
1.4264 (estimate)  
Solubility:
0.40g/l  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
99.2  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  

Literature

Title: Disrupted intracellular redox balance of the diplomonad fish parasite Spironucleus vortens by 5-nitroimidazoles and garlic-derived compounds.

Journal: Veterinary parasitology 20121123

Title: Simultaneous determination of morinidazole, its N-oxide, sulfate, and diastereoisomeric N(+)-glucuronides in human plasma by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20121101

Title: Genotoxicity profile of fexinidazole--a drug candidate in clinical development for human African trypanomiasis (sleeping sickness).

Journal: Mutagenesis 20120901

Title: Validation of a modified fluorimetric assay for the screening of trichomonacidal drugs.

Journal: Memorias do Instituto Oswaldo Cruz 20120801

Title: Development of metronidazole-resistant lines of Blastocystis sp.

Journal: Parasitology research 20120701

Title: Synthesis, in vitro and in vivo characterization of novel 99mTc-'4+1'-labeled 5-nitroimidazole derivatives as potential agents for imaging hypoxia.

Journal: Nuclear medicine and biology 20120701

Title: Influence of ligand denticity on the properties of novel ⁹⁹mTc(I)-carbonyl complexes. Application to the development of radiopharmaceuticals for imaging hypoxic tissue.

Journal: Bioorganic & medicinal chemistry 20120701

Title: First report of anti-Trichomonas vaginalis activity of the medicinal plant Polygala decumbens from the Brazilian semi-arid region, Caatinga.

Journal: Parasitology research 20120601

Title: Anti-Trichomonas vaginalis activity of saponins from Quillaja, Passiflora, and Ilex species.

Journal: Parasitology research 20120601

Title: Down-regulation of flavin reductase and alcohol dehydrogenase-1 (ADH1) in metronidazole-resistant isolates of Trichomonas vaginalis.

Journal: Molecular and biochemical parasitology 20120601

Title: Trichomonas vaginalis antimicrobial drug resistance in 6 US cities, STD Surveillance Network, 2009-2010.

Journal: Emerging infectious diseases 20120601

Title: [Far-IR and THz absorption spectra studies of metronidazole, tinidazole and ornidazole].

Journal: Guang pu xue yu guang pu fen xi = Guang pu 20120401

Title: Mucosal fixed drug eruption in a patient treated with ornidazole.

Journal: Journal of dermatological case reports 20120327

Title: Metabolism and pharmacokinetics of morinidazole in humans: identification of diastereoisomeric morpholine N+-glucuronides catalyzed by UDP glucuronosyltransferase 1A9.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120301

Title: Extensive genetic diversity, unique population structure and evidence of genetic exchange in the sexually transmitted parasite Trichomonas vaginalis.

Journal: PLoS neglected tropical diseases 20120301

Title: The anti-trypanosome drug fexinidazole shows potential for treating visceral leishmaniasis.

Journal: Science translational medicine 20120201

Title: Evolutionary, ecological and biotechnological perspectives on plasmids resident in the human gut mobile metagenome.

Journal: Bioengineered bugs 20120101

Title: Effect of a second nitroimidazole redox centre on the accumulation of a hypoxia marker: synthesis and in vitro evaluation of 99mTc-labeled bisnitroimidazole propylene amine oxime complexes.

Journal: Bioorganic & medicinal chemistry letters 20120101

Title: Virtual screening, identification and in vitro testing of novel inhibitors of O-acetyl-L-serine sulfhydrylase of Entamoeba histolytica.

Journal: PloS one 20120101

Title: Simultaneous determination of some antiprotozoal drugs in different combined dosage forms by mean centering of ratio spectra and multivariate calibration with model updating methods.

Journal: Chemistry Central journal 20120101

Title: A comparative study of oral single dose of metronidazole, tinidazole, secnidazole and ornidazole in bacterial vaginosis.

Journal: Indian journal of pharmacology 20120101

Title: Application of 2-trichloromethylbenzimidazole in analytical chemistry: a highly selective chromogenic reagent for thin-layer chromatography and some other analytical uses.

Journal: Journal of analytical methods in chemistry 20120101

Title: Computational study of proton and methyl cation affinities of imidazole-based highly energetic ionic liquids.

Journal: Journal of molecular modeling 20111001

Title: New approaches to the treatment of giardiasis.

Journal: Current opinion in infectious diseases 20111001

Title: High functionalization of 5-nitro-1H-imidazole derivatives: the TDAE approach.

Journal: Molecules (Basel, Switzerland) 20110812

Title: Pyruvate:ferredoxin oxidoreductase and thioredoxin reductase are involved in 5-nitroimidazole activation while flavin metabolism is linked to 5-nitroimidazole resistance in Giardia lamblia.

Journal: The Journal of antimicrobial chemotherapy 20110801

Title: The progress made in determining the Mycobacterium tuberculosis structural proteome.

Journal: Proteomics 20110801

Title: Genetically different clonal isolates of Trichomonas gallinae, obtained from the same bird, can vary in their drug susceptibility, an in vitro evidence.

Journal: Parasitology international 20110601

Title: Metronidazole-induced encephalopathy in a patient with liver cirrhosis.

Journal: The Korean journal of hepatology 20110601

Title: Antimicrobial resistance and prevalence of resistance genes in intestinal Bacteroidales strains.

Journal: Clinics (Sao Paulo, Brazil) 20110401

Title: 5-Nitroimidazole-based 1,3,4-thiadiazoles: heterocyclic analogs of metronidazole as anti-Helicobacter pylori agents.

Journal: Archiv der Pharmazie 20110301

Title: 2-Chloro-N-[(4-chloro-phen-yl)(phen-yl)meth-yl]-N-[2-(4-nitro-1H-imidazol-1-yl)eth-yl]ethanamine.

Journal: Acta crystallographica. Section E, Structure reports online 20110201

Title: Synthesis and biological characterisation of novel dithiocarbamate containing 5-nitroimidazole (99m)Tc-complexes as potential agents for targeting hypoxia.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: The genome of Akkermansia muciniphila, a dedicated intestinal mucin degrader, and its use in exploring intestinal metagenomes.

Journal: PloS one 20110101

Title: [Development and use of test systems for the evaluation of sensitivity of Trichomonas vaginalisto preparations of the 5-nitroimidazole and 5-nitrofuran groups].

Journal: Zhurnal mikrobiologii, epidemiologii, i immunobiologii 20110101

Title: [Short - term combined 5-nitroimidazole treatment in vaginal dysbacteriosis with dominant anaerobic species].

Journal: Akusherstvo i ginekologiia 20110101

Title: Molecularly imprinted polymers: present and future prospective.

Journal: International journal of molecular sciences 20110101

Title: Clinical, neuroimaging and pathological features of 5-nitroimidazole-induced encephalo-neuropathy in two patients: Insights into possible pathogenesis.

Journal: Neurology India 20110101

Title: Mebendazole compared with secnidazole in the treatment of adult giardiasis: a randomised, no-inferiority, open clinical trial.

Journal: Journal of parasitology research 20110101

Title: Fexinidazole--a new oral nitroimidazole drug candidate entering clinical development for the treatment of sleeping sickness.

Journal: PLoS neglected tropical diseases 20101201

Title: Study on ITS1 Gene of Iranian Trichomonas vaginalis by Molecular Methods.

Journal: Iranian journal of parasitology 20101201

Title: Susceptibility in vitro of clinically metronidazole-resistant Trichomonas vaginalis to nitazoxanide, toyocamycin, and 2-fluoro-2'-deoxyadenosine.

Journal: Parasitology research 20100901

Title: Giardiasis in the post genomic era: treatment, drug resistance and novel therapeutic perspectives.

Journal: Infectious disorders drug targets 20100801

Title: A new-generation 5-nitroimidazole can induce highly metronidazole-resistant Giardia lamblia in vitro.

Journal: International journal of antimicrobial agents 20100701

Title: 2-Chloro-4-nitro-1H-imidazole.

Journal: Acta crystallographica. Section E, Structure reports online 20100701

Title: Cationic nucleoside lipids derived from universal bases: A rational approach for siRNA transfection.

Journal: Bioconjugate chemistry 20100616

Title: Bacteroides fragilis RecA protein overexpression causes resistance to metronidazole.

Journal: Research in microbiology 20100601

Title: The flavin inhibitor diphenyleneiodonium renders Trichomonas vaginalis resistant to metronidazole, inhibits thioredoxin reductase and flavin reductase, and shuts off hydrogenosomal enzymatic pathways.

Journal: Molecular and biochemical parasitology 20100501

Title: Biophysical characterization and mutational analysis of the antibiotic resistance protein NimA from Deinococcus radiodurans.

Journal: Biochimica et biophysica acta 20100401

Title: Selectivity of Enzymatic Conversion of Oligonucleotide Probes during Nucleotide Polymorphism Analysis of DNA.

Journal: Acta naturae 20100401

Title: Ronidazole toxicosis in 3 society finches (Lonchura striata).

Journal: Veterinary pathology 20100301

Title: [Tetracyclines, sulfonamides, and metronidazole].

Journal: Enfermedades infecciosas y microbiologia clinica 20100201

Title: The tropical brown alga Lobophora variegata: a source of antiprotozoal compounds.

Journal: Marine drugs 20100101

Title: Documentation of in vivo and in vitro aerobic resistance of feline Tritrichomonas foetus isolates to ronidazole.

Journal: Journal of veterinary internal medicine 20100101

Title: Treatment of bacterial vaginosis: a multicenter, double-blind, double-dummy, randomised phase III study comparing secnidazole and metronidazole.

Journal: Infectious diseases in obstetrics and gynecology 20100101

Title: New 4-thiazolidinones of nicotinic acid with 2-Amino-6-methylbenzothiazole and their biological activity.

Journal: Scientia pharmaceutica 20100101

Title: Simultaneous Determination of Ofloxacin and Ornidazole in Solid Dosage Form by RP-HPLC and HPTLC Techniques.

Journal: Indian journal of pharmaceutical sciences 20100101

Title: Synthesis and cloxacillin antimicrobial enhancement of 2-methylsulfonylimidazolyl-1,4-dihydropyridine derivatives.

Journal: Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences 20100101

Title: In vitro resistance to 5-nitroimidazoles and benzimidazoles in Giardia duodenalis: variability and variation in gene expression.

Journal: Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases 20091201

Title: Overexpression of the rhamnose catabolism regulatory protein, RhaR: a novel mechanism for metronidazole resistance in Bacteroides thetaiotaomicron.

Journal: The Journal of antimicrobial chemotherapy 20090801

Title: New synthesis and antiparasitic activity of model 5-aryl-1-methyl-4-nitroimidazoles.

Journal: Molecules (Basel, Switzerland) 20090727

Title: Synthesis and electrochemistry of 2-ethenyl and 2-ethanyl derivatives of 5-nitroimidazole and antimicrobial activity against Giardia lamblia.

Journal: Journal of medicinal chemistry 20090709

Title: [Tinidazole: a classical anaerobical drug with multiple potential uses nowadays].

Journal: Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia 20090601

Title: Diffuse alveolar haemorrhage due to 5-nitroimidazole treatment.

Journal: Respirology (Carlton, Vic.) 20090501

Title: Trichomonas vaginalis: metronidazole and other nitroimidazole drugs are reduced by the flavin enzyme thioredoxin reductase and disrupt the cellular redox system. Implications for nitroimidazole toxicity and resistance.

Journal: Molecular microbiology 20090401

Title: Structure-activity relationships of antitubercular nitroimidazoles. 1. Structural features associated with aerobic and anaerobic activities of 4- and 5-nitroimidazoles.

Journal: Journal of medicinal chemistry 20090312

Title: Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

Journal: Journal of medicinal chemistry 20090212

Title: Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents.

Journal: European journal of medicinal chemistry 20090201

Title: Validation of a liquid chromatography-tandem mass spectrometry method for the identification and quantification of 5-nitroimidazole drugs and their corresponding hydroxy metabolites in lyophilised pork meat.

Journal: Journal of chromatography. A 20090109

Title: Guidelines for the treatment of bacterial vaginosis: focus on tinidazole.

Journal: Therapeutics and clinical risk management 20090101

Title: The old and new therapeutic approaches to the treatment of giardiasis: where are we?

Journal: Biologics : targets & therapy 20090101

Title: In vitro activity of Arbutus unedo leaf extracts against Trichomonas vaginalis trophozoites.

Journal: Turkiye parazitolojii dergisi 20090101

Title: Genotoxicity revaluation of three commercial nitroheterocyclic drugs: nifurtimox, benznidazole, and metronidazole.

Journal: Journal of parasitology research 20090101

Title: On the isolation and evaluation of a novel unsubstituted 5-nitroimidazole derivative as an agent to target tumor hypoxia.

Journal: Bioorganic & medicinal chemistry letters 20081001

Title: Toxicology.

Journal: Indian journal of pharmacology 20081001

Title: [Efficacy of 5-nitroimidazole derivatives in treatment of bacterial vaginosis].

Journal: Zhonghua yi xue za zhi 20080812

Title: Genotoxicity and cell death induced by tinidazole (TNZ).

Journal: Toxicology letters 20080730

Title: Intermediates in the reduction of the antituberculosis drug PA-824, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine, in aqueous solution.

Journal: Organic & biomolecular chemistry 20080607

Title: A comparison of metronidazole and single-dose ornidazole for the treatment of dientamoebiasis.

Journal: Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20080601

Title: High-resolution structure of the antibiotic resistance protein NimA from Deinococcus radiodurans.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20080601

Title: Use of molecularly imprinted solid-phase extraction sorbent for the determination of four 5-nitroimidazoles and three of their metabolites from egg-based samples before tandem LC-ESIMS/MS analysis.

Journal: Journal of agricultural and food chemistry 20080528

Title: The treatment of giardiasis in children: single-dose tinidazole compared with 3 days of nitazoxanide.

Journal: Annals of tropical medicine and parasitology 20080401

Title: NLNQ-1, a 2-[3-(2-nitro-1-imidazolyl) propylamino]-3-chloro-1,4-naphthoquinone, as a hypoxia-selective cytotoxin and radiosensitizer.

Journal: In vivo (Athens, Greece) 20080101

Title: Characterization of a Giardia lamblia WB C6 clone resistant to the isoflavone formononetin.

Journal: Microbiology (Reading, England) 20071201

Title: Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2H)-benzofuranone derivatives.

Journal: Bioorganic & medicinal chemistry letters 20071115

Title: Sequential regimens for Helicobacter pylori eradication.

Journal: Lancet (London, England) 20070922

Title: Crystal packing of two 5-substituted 2-methyl-4-nitro-1H-imidazoles.

Journal: Acta crystallographica. Section C, Crystal structure communications 20070801

Title: Two different modes of halogen bonding in two 4-nitroimidazole derivatives.

Journal: Acta crystallographica. Section C, Crystal structure communications 20070801

Title: Nitroimidazole action in Entamoeba histolytica: a central role for thioredoxin reductase.

Journal: PLoS biology 20070801

Title: A randomized, controlled, open-label trial of a single day of mebendazole versus a single dose of tinidazole in the treatment of giardiasis in children.

Journal: Current medical research and opinion 20061101

Title: Dissolution and vaginal absorption characteristics of metronidazole and ornidazole.

Journal: Die Pharmazie 20061001

Title: High throughput screening identified a substituted imidazole as a novel RANK pathway-selective osteoclastogenesis inhibitor.

Journal: Assay and drug development technologies 20060801

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Nitroimidazoles, part 2: Synthesis, antiviral and antitumor activity of new 4-nitroimidazoles.

Journal: Chemistry & biodiversity 20060501

Title: Analysis of four 5-nitroimidazoles and their corresponding hydroxylated metabolites in egg, processed egg, and chicken meat by isotope dilution liquid chromatography tandem mass spectrometry.

Journal: Journal of agricultural and food chemistry 20060322

Title: In vitro activities of tinidazole and metronidazole against Clostridium difficile, Prevotella bivia and Bacteroides fragilis.

Journal: Anaerobe 20051201

Title: Radiosynthesis and evaluation of two novel 123I-labeled 2-methyl-4-nitroimidazole derivatives as potential infection imaging agents.

Journal: Nuclear medicine and biology 20050501

Title: [Two cases of metronidazole-induced encephalopathy].

Journal: The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20050301

Title: Probing NMR parameters, structure and dynamics of 5-nitroimidazole derivatives. Density functional study of prototypical radiosensitizers.

Journal: Magnetic resonance in chemistry : MRC 20050201

Title: Structural basis of 5-nitroimidazole antibiotic resistance: the crystal structure of NimA from Deinococcus radiodurans.

Journal: The Journal of biological chemistry 20041231

Title: Variability and variation in drug susceptibility among Giardia duodenalis isolates and clones exposed to 5-nitroimidazoles and benzimidazoles in vitro.

Journal: The Journal of antimicrobial chemotherapy 20041001

Title: Synthesis and anti-tuberculosis activity of N-aryl-C-nitroazoles.

Journal: European journal of medicinal chemistry 20041001

Title: Stereoselective synthesis of cis-1,3-disubstituted cyclobutyl kinase inhibitors.

Journal: Organic letters 20040527

Title: Inhibition of adenosine deaminase by novel 5:7 fused heterocycles containing the imidazo[4,5-e][1,2,4]triazepine ring system: a structure-activity relationship study.

Journal: Journal of medicinal chemistry 20040212

Title: Synthesis and biological results of the technetium-99m-labeled 4-nitroimidazole for imaging tumor hypoxia.

Journal: Bioorganic & medicinal chemistry letters 20040209

Title: In vitro activity of antiamoebic drugs against clinical isolates of Entamoeba histolytica and Entamoeba dispar.

Journal: Annals of clinical microbiology and antimicrobials 20040101

Title: [Tetracyclines, sulfonamides and metronidazole].

Journal: Enfermedades infecciosas y microbiologia clinica 20031101

Title: Drug resistance in the sexually transmitted protozoan Trichomonas vaginalis.

Journal: Cell research 20030801

Title: Two stability-indicating UV spectrophotometric methods for the analysis of hydrolyzed tinidazole.

Journal: Journal of pharmaceutical and biomedical analysis 20030310

Title: [Therapeutic aspects of trichomoniasis].

Journal: Srpski arhiv za celokupno lekarstvo 20030101

Title: Pathways of reductive fragmentation of heterocyclic nitroarylmethyl quaternary ammonium prodrugs of mechlorethamine.

Journal: Radiation research 20021201

Title: 'In vitro' study of chemotherapeutic activity of sulphimidazole on some sensitive and metronidazole-resistant Trichomonas vaginalis strains.

Journal: Pharmacological research 20021101

Title: [Prospects for development of new antituberculous drugs].

Journal: Kekkaku : [Tuberculosis] 20020801

Title: New findings in beta-lactam and metronidazole resistant Bacteroides fragilis group.

Journal: International journal of antimicrobial agents 20020501

Title: Current trends in research into the waterborne parasite Giardia.

Journal: Critical reviews in microbiology 20020101

Title: Synthesis and calcium channel antagonist activity of 1,4-dihydropyridine derivatives containing 4-nitroimidazolyl substituents.

Journal: Arzneimittel-Forschung 20020101

Title: Effect of metronidazole on spermatogenesis and FSH, LH and testosterone levels of pre-pubertal rats.

Journal: Indian journal of experimental biology 20011101

Title: Investigation of 5-nitrofuran derivatives: synthesis, antibacterial activity, and quantitative structure-activity relationships.

Journal: Journal of medicinal chemistry 20011025

Title: Prevalence of 5-nitroimidazole-resistant trichomonas vaginalis in Oviedo, Spain.

Journal: Sexually transmitted diseases 20010201

Title: Prevalence and characteristics of nim genes encoding 5-nitroimidazole resistance among Bacteroides strains isolated in Morocco.

Journal: Microbial drug resistance (Larchmont, N.Y.) 20010101

Title: 5-Nitroimidazole derivatives as possible antibacterial and antifungal agents.

Journal: Farmaco (Societa chimica italiana : 1989) 19990101

Title: Antituberculosis activity of certain antifungal and antihelmintic drugs.

Journal: Tubercle and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease 19990101

Title: In-vitro studies of two 5-nitroimidazole derivatives.

Journal: The Journal of antimicrobial chemotherapy 19970701

Title: Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.

Journal: Annals of tropical medicine and parasitology 19961201

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Tags:3034-38-6 Molecular Formula|3034-38-6 MDL|3034-38-6 SMILES|3034-38-6 4-Nitroimidazole |Organic_Building_Blocks