1615-53-8

Basic information

• Product Name: sulfonidazole
• Synonyms: sulfonidazole;1-methyl-2-methylsulphonyl-5-nitro-imidazole;1-methyl-2-(methylsulfonyl)-5-nitro-1H-imidazole
• CAS NO: 1615-53-8
• Molecular Formula: C₅H₇N₃O₄S
• Molecular Weight: 205.19178
• Mol File: 1615-53-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 91.0-92.5 °C
• Boiling Point: 424.8°Cat760mmHg
• Flash Point: 210.7°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 2E-07mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.92±0.25(Predicted)
• CAS DataBase Reference: sulfonidazole(CAS DataBase Reference)
• NIST Chemistry Reference: sulfonidazole(1615-53-8)
• EPA Substance Registry System: sulfonidazole(1615-53-8)

Safety Data

• Hazardous Substances Data: 1615-53-8(Hazardous Substances Data)

Usage

General Description

Sulfonidazole is a synthetic antibacterial and antiprotozoal agent that belongs to the class of sulfonamide drugs. It works by interfering with the synthesis of tetrahydrofolic acid, which is essential for the growth and reproduction of bacteria and protozoa. Sulfonidazole is commonly used to treat various infections caused by susceptible organisms, including acute gastrointestinal infections, certain types of sexually transmitted diseases, and some parasitic infections. It is available in oral and topical formulations and is often used in combination with other antibiotics for a broader spectrum of activity. Sulfonidazole is generally well-tolerated, but common side effects may include nausea, vomiting, diarrhea, and rashes. It is important to use sulfonidazole only as prescribed by a healthcare professional and to complete the full course of treatment to ensure the best possible outcome.

InChI:InChI=1/C5H7N3O4S/c1-7-4(8(9)10)3-6-5(7)13(2,11)12/h3H,1-2H3

Upstream product

• 1615-41-4 1-methyl-2-(methylsulfanyl)-5-nitro-1H-imidazole 
• 14486-52-3 2-methylmercapto-3-methylimidazole 

Downstream Products

• 86151-49-7 (1-Methyl-5-nitro-1H-imidazol-2-yl)-(4-nitro-phenyl)-amine 
• 56302-13-7 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one 
• 86008-57-3 bisimidazopyridine 
• 86008-54-0 C₁₃H₁₆N₄O₄S₃ 
• 86008-51-7 N-(2-Methanesulfonyl-3-methyl-3H-imidazol-4-yl)-3,4,5-trimethoxy-benzamide 
• 86008-49-3 N-(2-Methanesulfonyl-3-methyl-3H-imidazol-4-yl)-4-nitro-benzamide 
• 86008-50-6 4-Chloro-N-(2-methanesulfonyl-3-methyl-3H-imidazol-4-yl)-benzamide 
• 1615-42-5 1-methyl-5-nitro-1H-imidazole-2-carbonitrile 
• 92478-10-9 2-benzyloxy-1-methyl-5-nitroimidazole 
• 85694-37-7 1-(1-Methyl-5-nitro-1H-imidazol-2-yl)-4-(3,4,5-trimethoxy-phenyl)-[1,2,4]triazolidine-3,5-dione 
• 85694-40-2 1-(1-Methyl-5-nitro-1H-imidazol-2-yl)-4-(2-phenyl-cyclopropyl)-[1,2,4]triazolidine-3,5-dione 
• 85694-39-9 1-(1-Methyl-5-nitro-1H-imidazol-2-yl)-4-phenethyl-[1,2,4]triazolidine-3,5-dione 
• 85694-38-8 1-(1-Methyl-5-nitro-1H-imidazol-2-yl)-4-((E)-styryl)-[1,2,4]triazolidine-3,5-dione 
• 86072-08-4 4-Chloro-N-(1-methyl-5-nitro-1H-imidazol-2-yl)-benzamide 

Relevant articles and documents

Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead

As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.