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 |
|---|---|---|
| Hypoxia in human intraperitoneal and extremity sarcomas. | 2001 Feb 1 |
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| Imaging hypoxia in tumors. | 2001 Oct |
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| Pharmacokinetics of EF5 [2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide] in human patients: implications for hypoxia measurements in vivo by 2-nitroimidazoles. | 2001 Sep |
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| Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170. | 2002 Jan |
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| Effect of a hypoxic cell sensitizer doranidazole on the radiation-induced apoptosis of mouse L5178Y lymphoma cells. | 2002 Jun |
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| The synthesis and radiolabeling of 2-nitroimidazole derivatives of cyclam and their preclinical evaluation as positive markers of tumor hypoxia. | 2002 Jun |
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| Monitoring the synthetic reaction of a polyamide/peptide conjugate using electrospray ionization mass spectrometry. | 2003 |
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| Non-invasive PET and SPECT imaging of tissue hypoxia using isotopically labeled 2-nitroimidazoles. | 2003 |
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| In vivo colocalization of 2-nitroimidazole EF5 fluorescence intensity and electron paramagnetic resonance oximetry in mouse tumors. | 2003 Apr |
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| 99mTcO(BAT-NI), a novel nitroimidazole tracer: in vivo uptake studies in ischaemic myocardium. | 2003 Apr |
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| Professor Tom Connors and the development of novel cancer therapies by the Phase I/II Clinical Trials Committee of Cancer Research UK. | 2003 Aug 4 |
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| The farnesyltransferase inhibitor R115777 reduces hypoxia and matrix metalloproteinase 2 expression in human glioma xenograft. | 2003 Dec 1 |
|
| Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5. | 2003 Feb |
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| A novel hypoxia-dependent 2-nitroimidazole KIN-841 inhibits tumour-specific angiogenesis by blocking production of angiogenic factors. | 2003 Jan 27 |
|
| Pimonidazole binding in C6 rat brain glioma: relation with lipid droplet detection. | 2003 May 6 |
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| Hypoxia is important in the biology and aggression of human glial brain tumors. | 2004 Dec 15 |
|
| Reaction of azole heterocycles with tris(dimethylamino)borane, a new method for the construction of tripodal borate-centred ligands. | 2006 Jul 5 |
|
| Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis. | 2006 Jun 9 |
|
| Review article: recurrence of Crohn's disease after surgery - the need for treatment of new lesions. | 2006 Oct |
|
| Azanonaboranes containing imidazole derivatives for boron neutron capture therapy: synthesis, characterization, and in vitro toxicity evaluation. | 2006 Oct 25 |
|
| Imaging oxygenation of human tumours. | 2007 Apr |
|
| In situ oxygen utilization in the rat intervertebral disc. | 2007 Mar |
|
| Determination of tumour hypoxia with the PET tracer [18F]EF3: improvement of the tumour-to-background ratio in a mouse tumour model. | 2007 Sep |
|
| Potent and highly selective hypoxia-activated achiral phosphoramidate mustards as anticancer drugs. | 2008 Apr 24 |
|
| Design, synthesis, and radiosensitizing activities of sugar-hybrid hypoxic cell radiosensitizers. | 2008 Jan 15 |
|
| 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 Jul |
|
| Design of antiangiogenic hypoxic cell radiosensitizers: 2-nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety. | 2008 Jun 1 |
|
| Regulation of cell survival and death signals induced by oxidative stress. | 2008 Sep |
|
| Ultra performance liquid chromatography tandem mass spectrometry performance evaluation for analysis of antibiotics in natural waters. | 2009 Mar |
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
Fri Dec 15 16:40:09 GMT 2023
by
admin
on
Fri Dec 15 16:40:09 GMT 2023
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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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m2184
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