13182-89-3

Usage

Uses

Used in Diabetes Treatment:
Benzoylmetronildazole is used as an antiglycation agent for the treatment of diabetes mellitus. It helps in managing the complications associated with diabetes by inhibiting the formation of advanced glycation end-products (AGEs), which contribute to the progression of the disease.
Used in Anti-infective Applications:
Benzoylmetronildazole is used as an anti-infective agent, leveraging its properties as a derivative of Metronidazole. It is effective in treating various bacterial infections, including rosacea, a skin condition characterized by redness and inflammation.
Used in Pharmaceutical Industry:
Benzoylmetronildazole is used as an active pharmaceutical ingredient in various branded products, such as Flagyl (Searle), Metrogel (Galderma), Metrogel (3M Pharmaceuticals), Noritate (Sanofi Aventis), and Vandazole (Teva). These products are formulated to target specific conditions, such as bacterial infections and diabetes mellitus, and are widely used in the pharmaceutical industry to improve patient outcomes.

InChI:InChI=1/C7H6O2.C6H9N3O3/c8-7(9)6-4-2-1-3-5-6;1-5-7-4-6(9(11)12)8(5)2-3-10/h1-5H,(H,8,9);4,10H,2-3H2,1H3

Upstream product

• 443-48-1 metronidazole 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 30575-42-9 toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester 

Downstream Products

• 443-48-1 metronidazole 
• 65-85-0 benzoic acid 
• 1149334-67-7 C₁₃H₁₂N₄O₆ 
• 306281-22-1 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-bromobenzoate 
• 102274-42-0 C₁₃H₁₂BrN₃O₄ 
• 1392515-27-3 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-bromobenzoate 
• 1403815-82-6 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylbenzoate 
• 303797-32-2 C₁₁H₁₁N₃O₅ 
• 13182-93-9 C₁₆H₁₉N₃O₇ 
• 1403815-81-5 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-methylbenzoate 
• 1403815-93-9 C₁₆H₁₉N₃O₄ 
• 1403815-92-8 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-chloro-4,5-difluorobenzoate 

Relevant academic research and scientific papers

Multifunctional derivatives of metronidazole

The design and synthesis of a series of multifunctional metronidazole derivatives are described. The main series are multi-esters having two or more metronidazole groups linked together by aryl or alkyl systems. A second system is two nitro-2-methylimidazole groups joined by a dimethylene link. The third is polymeric 2-(2-methyl-5-nitroimidazol-1-yl)ethyl acrylate. The triester, metronidazole trimesate, is exceptionally active as an antibacterial compound, which appears to be associated with a rigid, three-point attachment.

Synthesis method of benzoyl metronidazole

The invention provides a synthesis method of benzoyl metronidazole, which comprises the following steps: by using metronidazole and benzoyl chloride as raw materials, dropwisely adding ammonia water in the presence of an esterification catalyst and a phase transfer catalyst to carry out esterification reaction. The raw materials adopted in the method are non-toxic, green, environment-friendly andsafe; meanwhile, the reaction activity is improved by adding a catalyst, and the reaction temperature can be effectively reduced, so that the hydrolysis of benzoyl chloride is avoided, and the solventdehydration operation is omitted; in addition, ammonia water is adopted to replace pyridine and other organic bases to serve as an acid-binding agent, so that extraction separation can be directly conducted after reaction, and operation is simplified.

Metronidazole aryloxy, carboxy and azole derivatives: Synthesis, anti-tumor activity, QSAR, molecular docking and dynamics studies

A series of novel metronidazole aryloxy, carboxy and azole derivatives has been synthesized and their cytotoxic activities on three cancer cell lines were evaluated by MTT assay. Compounds 4m, 4l and 4d showed the most potent cytotoxic activity (IC50s less than 100 μg/mL). Apoptosis was also detected for these compounds by flow cytometry. Docking studies were performed in order to propose the probable target protein. In the next step, molecular dynamics simulation was carried out on the proposed target protein, focal adhesion kinase (FAK, PDB code: 2ETM), bound to compound 4m. As, 4m showed a potent cytotoxic activity and an acceptable apoptotic effect, it can be a potential anticancer candidate that may work through inhibition of FAK.

Evaluation of lipophilicity, antimicrobial activity and mutagenicity of some novel ester prodrugs of metronidazole

Various novel aliphatic and aromatic esters of metronidazole have been synthesized to improve the physicochemical properties (Rm values, lipophilicity) using prodrug approach. The alcoholic functional group of metronidazole is readily esterified, thus several novel ester prodrugs of metronidazole have been synthesized and evaluated for their anaerobic antibacterial activity and mutagenicity. These compounds have been characterized by UV, IR, 1H NMR, mass spectra and elemental analysis. The partition coefficient of esters is determined by n-octanol/water system, RP-TLC and computed in silico. Anaerobic-activity against C. perfringens. determined in terms of MIC (μg/ml) show the esters, particularly SDS-18 and SDS-19, to be more potent in comparison to metronidazole. The Ames test is used to compare the mutagenic potential of the synthesized 5-nitroimidazoles.

Prodrugs - Part 2. Acylbenzoate esters of metronidazole

The design and synthesis of a series of chain and cyclic acylbenzoate esters of metronidazole are described. The esters are designed to be both lipophilic and reactive in their hydrolysis reactions. The alkaline hydrolyses of the chain 2-acylbenzoates are relatively rapid, employing an intramolecular catalytic route, while the reactions of the 4-formylbenzoate and cyclic 2-formylbenzoate are also relatively rapid using the normal pathway. The anti-bacterial activity of the esters are comparable to that of metronidazole.