Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C3H3N3O2 |
| Molecular Weight | 113.0748 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+](=O)C1=NC=CN1
InChI
InChIKey=YZEUHQHUFTYLPH-UHFFFAOYSA-N
InChI=1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)
| Molecular Formula | C3H3N3O2 |
| Molecular Weight | 113.0748 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Azomycin (2-Nitroimidazole) is a natural antimicrobial antibiotic produced by a strain of Nocardia mesenterica, that have been used to combat anaerobic bacterial and parasitic infections. Azomycin and other 2’-nitroimidazoles show anti-ischemic and anti-inflammatory pharmacological properties. Azomycin is cytotoxic and change drug-metabolizing cytochrome P450, NADPH dependent reductase enzymes and cause depletion of tissue oxygen pressure. Azomycin is a prodrug. Unionized Azomycin is selective for anaerobic bacteria due to their ability to intracellularly reduce Azomycin to its active form. This reduced Azomycin then covalently binds to DNA, disrupt its helical structure, inhibiting bacterial nucleic acid synthesis and resulting in bacterial cell death.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Downregulation of matrix metalloprotease-9 and urokinase plasminogen activator by TX-1877 results in decreased tumor growth and metastasis on xenograft model of rectal cancer. | 2009-10 |
|
| Nitroimidazole-based bioreductive compounds bearing a quinazoline or a naphthyridine chromophore. | 2009-07 |
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| Control of pore size and functionality in isoreticular zeolitic imidazolate frameworks and their carbon dioxide selective capture properties. | 2009-03-25 |
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| Synthesis and hypoxia selective radiosensitization potential of beta-2-FAZA and beta-3-FAZL: fluorinated azomycin beta-nucleosides. | 2009-03 |
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| Ultra performance liquid chromatography tandem mass spectrometry performance evaluation for analysis of antibiotics in natural waters. | 2009-03 |
|
| The novel hypoxic cell radiosensitizer, TX-1877 has antitumor activity through suppression of angiogenesis and inhibits liver metastasis on xenograft model of pancreatic cancer. | 2008-12-18 |
|
| Imaging and analytical methods as applied to the evaluation of vasculature and hypoxia in human brain tumors. | 2008-12 |
|
| Comparative pharmacokinetics, biodistribution, metabolism and hypoxia-dependent uptake of [18F]-EF3 and [18F]-MISO in rodent tumor models. | 2008-12 |
|
| On the isolation and evaluation of a novel unsubstituted 5-nitroimidazole derivative as an agent to target tumor hypoxia. | 2008-10-01 |
|
| Regulation of cell survival and death signals induced by oxidative stress. | 2008-09 |
|
| FDG uptake, a surrogate of tumour hypoxia? | 2008-08 |
|
| NLNQ-1, a 2-[3-(2-nitro-1-imidazolyl) propylamino]-3-chloro-1,4-naphthoquinone, as a hypoxia-selective cytotoxin and radiosensitizer. | 2008-07-10 |
|
| Reactions of NO(2)Cl with imidazole: a model study for the corresponding reactions of guanine. | 2008-07-03 |
|
| Bactericidal activity of 2-nitroimidazole against the active replicating stage of Mycobacterium bovis BCG and Mycobacterium tuberculosis with intracellular efficacy in THP-1 macrophages. | 2008-07 |
|
| Determination of tumour hypoxia with [18F]EF3 in patients with head and neck tumours: a phase I study to assess the tracer pharmacokinetics, biodistribution and metabolism. | 2008-07 |
|
| Design of antiangiogenic hypoxic cell radiosensitizers: 2-nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety. | 2008-06-01 |
|
| Potent and highly selective hypoxia-activated achiral phosphoramidate mustards as anticancer drugs. | 2008-04-24 |
|
| Novel nitroheterocyclic hypoxic markers for solid tumor: synthesis and biological evaluation. | 2008-03-15 |
|
| Design, synthesis, and radiosensitizing activities of sugar-hybrid hypoxic cell radiosensitizers. | 2008-01-15 |
|
| Role of hypoxia-inducible factor 1 alpha in the integrity of articular cartilage in murine knee joints. | 2008 |
|
| Hypoxia inducible factor (HIF)-1 coordinates induction of Toll-like receptors TLR2 and TLR6 during hypoxia. | 2007-12-26 |
|
| Patterns and levels of hypoxia in head and neck squamous cell carcinomas and their relationship to patient outcome. | 2007-11-15 |
|
| The radiosensitizing effect of doranidazole on human colorectal cancer cells exposed to high doses of irradiation. | 2007-10-06 |
|
| Determination of tumour hypoxia with the PET tracer [18F]EF3: improvement of the tumour-to-background ratio in a mouse tumour model. | 2007-09 |
|
| Imaging oxygenation of human tumours. | 2007-04 |
|
| From "Hellstrom Paradox" to anti-adenosinergic cancer immunotherapy. | 2007-03 |
|
| In situ oxygen utilization in the rat intervertebral disc. | 2007-03 |
|
| Initial evaluation of dynamic human imaging using 18F-FRP170 as a new PET tracer for imaging hypoxia. | 2007-02 |
|
| Tacrolimus (FK506) limits accumulation of granulocytes and platelets and protects against brain damage after transient focal cerebral ischemia in rat. | 2007-02 |
|
| In vivo evaluation of the nitroimidazole-based thioflavin-T derivatives as cerebral ischemia markers. | 2007 |
|
| Imaging of tumor hypoxia with [124I]IAZA in comparison with [18F]FMISO and [18F]FAZA--first small animal PET results. | 2007 |
|
| Ruthenium(III) maltolato-nitroimidazole complexes: synthesis and biological activity. | 2006-12 |
|
| Oxygen levels in normal and previously irradiated human skin as assessed by EF5 binding. | 2006-12 |
|
| Azanonaboranes containing imidazole derivatives for boron neutron capture therapy: synthesis, characterization, and in vitro toxicity evaluation. | 2006-10-25 |
|
| Treatment with Imatinib in NSCLC is associated with decrease of phosphorylated PDGFR-beta and VEGF expression, decrease in interstitial fluid pressure and improvement of oxygenation. | 2006-10-23 |
|
| Review article: recurrence of Crohn's disease after surgery - the need for treatment of new lesions. | 2006-10 |
|
| Temporal and topographic profiles of tissue hypoxia following transient focal cerebral ischemia in rats. | 2006-08 |
|
| Reaction of azole heterocycles with tris(dimethylamino)borane, a new method for the construction of tripodal borate-centred ligands. | 2006-07-05 |
|
| Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis. | 2006-06-09 |
|
| Novel fluorescent markers for hypoxic cells of naphthalimides with two heterocyclic side chains for bioreductive binding. | 2006-05-01 |
|
| Synthesis and evaluation of novel 8-oxo-8H-cyclopenta[a]acenaphthylene-7-carbonitriles as long-wavelength fluorescent markers for hypoxic cells in solid tumor. | 2006-03-15 |
|
| Establishment and characterization of multicellular spheroids from a human glioma cell line; Implications for tumor therapy. | 2006-03-02 |
|
| EF5 binding and clinical outcome in human soft tissue sarcomas. | 2006-03-01 |
|
| Characterization of the tuberculous granuloma in murine and human lungs: cellular composition and relative tissue oxygen tension. | 2006-02 |
|
| Reevaluation of the radiosensitizing effects of sanazole and nimorazole in vitro and in vivo. | 2005-12 |
|
| TX-1877, a bifunctional hypoxic cell radiosensitizer, enhances anticancer host response: immune cell migration and nitric oxide production. | 2005-09-10 |
|
| Modulation of intratumoral hypoxia by the epidermal growth factor receptor inhibitor gefitinib detected using small animal PET imaging. | 2005-09 |
|
| HEGPOL: randomized, placebo controlled, multicenter, double-blind clinical trial to investigate hepatoprotective effects of glycine in the postoperative phase of liver transplantation [ISRCTN69350312]. | 2005-08-17 |
|
| Synthesis, in vitro-antimycobacterial activity and cytotoxicity of some alkyl alpha-(5-aryl-1, 3, 4-thiadiazole-2-ylthio)acetates. | 2005-03 |
|
| A one-pot synthesis of 1-alpha- and 1-beta-D-arabinofuranosyl-2-nitroimidazoles: synthons to the markers of tumor hypoxia. | 2005 |
Sample Use Guides
In Vivo Use Guide
Sources: https://goo.gl/q8xwJ2
150-200mg/kg
Route of Administration:
Oral
HT-1080, LoVo and V79-379A cell lines were used for activity evaluation. Cells were incubated in radiosensitizer (Azomycin, 2mmol/dm^3) solution for 80 min before irradiation with 250 kVp 15 mA X-rays (1.46 mm Cu HVL) at a dose rate of 2.7 Gy/min. After 7 days incubation in fresh growth medium, V79-379A colonies were stained with methylene blue in 70 per cent v/v ethanol/water. HT-1080 colonies were stained with crystal violet in 70 per cent v/v ethanol/water after 9-10 days incubation . LoVo colonies were stained with aqueous crystal violet after 12-14 days incubation.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:34:09 GMT 2025
by
admin
on
Mon Mar 31 18:34:09 GMT 2025
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| Record UNII |
K8E96XL55D
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| Record Status |
Validated (UNII)
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| Record Version |
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208-425-5
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DTXSID7060178
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NITROIMIDAZOLE
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