31876-69-4

Basic information

• Product Name: 1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-one
• Synonyms: 1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-one;Ornidazole Related CoMpound;1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-one;Ornidazole Related Compound 2;Ornidazole Impurity A
• CAS NO: 31876-69-4
• Molecular Formula: C₇H₉N₃O₃
• Molecular Weight: 183.1647
• Mol File: 31876-69-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 378.4°Cat760mmHg
• Flash Point: 182.7°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 6.29E-06mmHg at 25°C
• Refractive Index: 1.597
• PKA: 2.09±0.34(Predicted)
• CAS DataBase Reference: 1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-one(31876-69-4)
• EPA Substance Registry System: 1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-one(31876-69-4)

Safety Data

• Hazardous Substances Data: 31876-69-4(Hazardous Substances Data)

Usage

Description

1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-one, commonly known as misonidazole, is a nitroimidazole derivative with potential medical applications. It is recognized for its ability to sensitize hypoxic cancer cells to radiation therapy, thereby enhancing the effectiveness of cancer treatment.

Uses

Used in Cancer Treatment:
Misonidazole is used as a radiosensitizer in cancer treatment to increase the susceptibility of hypoxic cancer cells to radiation. It selectively targets and damages the DNA of these cells, leading to improved outcomes in radiotherapy for cancer patients.
Used in Combination Therapy:
Misonidazole is also being explored for its potential as a radiosensitizer in combination with other cancer treatments. This approach aims to enhance the overall effectiveness of cancer therapy by leveraging the synergistic effects of misonidazole with conventional treatments.
Used in Research and Development:
As a compound with potential applications in cancer treatment, misonidazole is used in the research and development of new therapeutic strategies. Further investigation is necessary to fully understand its mechanisms of action, side effects, and limitations in clinical use, which will inform the development of more effective and safer cancer treatments.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, misonidazole is utilized for the development of drugs that target hypoxic cancer cells. Its unique properties make it a valuable compound for creating new medications that can improve the success rate of radiation therapy and potentially reduce side effects associated with cancer treatment.
Used in Medical Imaging:
Misonidazole's ability to target hypoxic cells also makes it a candidate for use in medical imaging techniques. It could potentially be employed as a contrast agent to help visualize hypoxic regions within tumors, aiding in the diagnosis and treatment planning for cancer patients.

InChI:InChI=1/C7H9N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3H,4H2,1-2H3

Upstream product

• 3366-95-8 secnidazole 
• 696-23-1 2-methyl-5-nitro-1H-imidazole 
• 78-95-5 chloroacetone 

Relevant articles and documents

5-Nitroimidazole-derived Schiff bases and their copper(II) complexes exhibit potent antimicrobial activity against pathogenic anaerobic bacteria

In the present work a family of novel secnidazole-derived Schiff base compounds and their copper(II) complexes were synthesized. The antimicrobial activities of the compounds were evaluated against clinically important anaerobic bacterial strains. The compounds exhibited in vitro antibacterial activity against Bacteroides fragilis, Bacteroides thetaiotaomicron, Bacteroides vulgatus, Bacteroides ovatus, Parabacteroides distasonis and Fusubacterium nucleatum pathogenic anaerobic bacteria. Upon coordination to copper(II) the antibacterial activity significantly increased in several cases. Some derivatives were even more active than the antimicrobial drugs secnidazole and metronidazole. Therefore, the compounds under study are suitable for in vivo evaluation and the microorganisms should be classified as susceptible to them. Electrochemical studies on the reduction of the nitro group revealed that the compounds show comparable reduction potentials, which are in the same range of the bio-reducible drugs secnidazole and benznidazole. The nitro group reduction potential is more favorable for the copper(II) complexes than for the starting ligands. Hence, the antimicrobial activities of the compounds under study might in part be related to intracellular bio-reduction activation. Considering the increasing resistance rates of anaerobic bacteria against a wide range of antimicrobial drugs, the present work constitutes an important contribution to the development of new antibacterial drug candidates.

Discovery of novel nitroimidazole enols as Pseudomonas aeruginosa DNA cleavage agents

A series of nitroimidazole enols as new bacterial DNA-targeting agents were for the first time designed, synthesized and characterized by NMR, IR and HRMS spectra. The antimicrobial screening revealed that 2-methoxyphenyl nitroimidazole enol 3i possessed stronger anti-P. aeruginosa efficacy (MIC = 0.10 μmol/mL) than reference drugs Norfloxacin and Metronidazole. Time-kill kinetic assay manifested that the active molecule 3i could rapidly kill the tested strains. Molecular docking indicated that the interactions between compound 3i and topoisomerase II were driven by hydrogen bonds. Quantum chemical study was also performed on 3i to understand the structural features essential for activity. Further research found that compound 3i was not able to effectively intercalate into bacterial DNA but could cleave DNA isolated from the standard P. aeruginosa strain, which might block DNA replication to exert the efficient bioactivities, and this active molecule was also able to be stored and carried by human serum albumin via hydrophobic interactions and hydrogen bonds.