13182-89-3

Basic information

• Product Name: Benzoylmetronildazole
• Synonyms: Benzoic acid [2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl] ester;2-(2-methyl-5-nitro-imidazol-1-yl)ethyl benzoate;2-(2-methyl-5-nitroimidazol-1-yl)ethyl benzoate;benzoic acid 2-(2-methyl-5-nitro-imidazol-1-yl)ethyl ester;1-(2-Benzoyloxyethyl)-5-Nitro-2-Methyl-Imidazole;Metronidazole Benzoate (100 mg);1H-IMidazole-1-ethanol,2-Methyl-5-nitro-, 1-benzoate;benzoylmetronidazole
• CAS NO: 13182-89-3
• Molecular Formula: C₁₃H₁₃N₃O₄
• Molecular Weight: 275.26
• EINECS: 236-131-7
• Product Categories: Pharmaceutical intermediate
• Mol File: 13182-89-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 100 °C
• Boiling Point: 487.7 °C at 760 mmHg
• Flash Point: 248.7 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 2.88E-14mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Practically insoluble in water, freely soluble in methylene chloride, soluble in acetone, slightly soluble in alcohol.
• PKA: 2.44±0.34(Predicted)
• CAS DataBase Reference: Benzoylmetronildazole(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoylmetronildazole(13182-89-3)
• EPA Substance Registry System: Benzoylmetronildazole(13182-89-3)

Safety Data

• Hazardous Substances Data: 13182-89-3(Hazardous Substances Data)

Usage

Chemical Properties

White or slightly yellowish, crystalline powder or flakes.

Uses

Different sources of media describe the Uses of 13182-89-3 differently. You can refer to the following data:
1. Benzoylmetronildazole is a new class of antiglycation agents used to treat diabetes mellitus. Benzoylmetronildazole is also a derivative of Metronidazole (M338880), an antibacterial in the treatment o f rosacea.
2. Anti-infective

Definition

ChEBI: A benzoate ester resulting from the formal condensation of benzoic acid with the hydroxy group of metronidazole.

Brand name

Flagyl (Searle); Metrogel (Galderma); Metrogel (3M Pharmaceuticals); Noritate(Sanofi Aventis); Vandazole (Teva).

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 
• 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 
• 65-85-0 benzoic acid 

Relevant articles and documents

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.

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.

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.