53716-50-0

Basic information

• Product Name: Oxfendazole
• Synonyms: [5-(phenylsulfinyl)-1h-benzimidazol-2-yl]carbamic acid methyl ester;LODITAC;OXFENDAZOLE;(5-(phenylsulfinyl)-1h-benzimidazol-2-yl)-carbamicacimethylester;5-(phenylsulfinyl)-2-benzimidazolecarbamicacidmethylester;5-(phenylsulfinyl)-2-benzimidazolecarbamicacimethylester;5-phenylsulfinyl-2-carbomethoxyaminobenzimidazole;hoe8105
• CAS NO: 53716-50-0
• Molecular Formula: C₁₅H₁₃N₃O₃S
• Molecular Weight: 315.35
• EINECS: 258-714-5
• Product Categories: Metabolites;Veterinaries;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds;Pharmaceutical intermediate;Amines, Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds;TICLID
• Mol File: 53716-50-0.mol

Chemical Properties

• Melting Point: 298-300?C
• Appearance: COA
• Density: 1.3229 (rough estimate)
• Refractive Index: 1.6740 (estimate)
• Storage Temp.: 2-8°C
• PKA: 10.27±0.10(Predicted)
• Merck: 14,6935
• CAS DataBase Reference: Oxfendazole(CAS DataBase Reference)
• NIST Chemistry Reference: Oxfendazole(53716-50-0)
• EPA Substance Registry System: Oxfendazole(53716-50-0)

Safety Data

• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• RTECS: FD0835000
• Hazardous Substances Data: 53716-50-0(Hazardous Substances Data)

Usage

Uses

Used in Veterinary Medicine:
Oxfendazole is used as an anthelmintic for the treatment and control of various parasitic infections in livestock and poultry, such as horses, goats, cattle, and sheep. It is effective against roundworms, tapeworms, strongyles, and pinworms, helping to maintain the health and productivity of these animals.
Used as a PAF Inhibitor:
Oxfendazole is also used as a platelet-activating factor (PAF) inhibitor, which can have potential applications in various medical and pharmaceutical contexts, such as treating inflammation and other conditions related to PAF activity.

References

https://en.wikipedia.org/wiki/Oxfendazole http://www.vetsfarma.com/poultry3.html http://parasitipedia.net/index.php? option=com_content&view=article&id=2517&Itemid=2790

Originator

Autoworm,Coopers

Manufacturing Process

5.0 g of 2-amino-4-chloro-1-nitrobenzene is added to a solution of sodium phenyl mercaptide, prepared under nitrogen from 2.53 g 57% sodium hydride and 6.2 ml thiophenol in 20 ml dimethylformamide, with a 10 ml dimethylformamide rinse. The mixture is stirred under nitrogen for 3 h at 20°30°C and then diluted with water. The crude product is washed with water and hexane, then recrystallized from methanol, yielding 2-amino-4-phenylthio-1nitrobenzene. 6.0 g of 2-amino-4-phenylthio-1-nitrobenzene is dissolved in 80 ml acetic anhydride and treated with a few drops of sulfuric acid. The mixture is left at 20°-30°C for 2 h then a little sodium acetate added and the solvent removed under vacuum. The residue is treated with water, filtered and recrystallized from methanol yielding 2-acetamido-4-phenylthio-1-nitrobenzene. 7.0 g of 2-acetamido-4-phenylthio-1-nitrobenzene is dissolved in 70 ml chloroform and treated, at -20°C to -15°C, with a solution of 5.0 g 40% peracetic acid in 10 ml methanol. The mixture is allowed to warm slowly to 20°C and stirred for 4 h. The reaction mixture is extracted with sodium bisulfite solution, then sodium bicarbonate solution, dried and evaporated. The residual gum of 2-acetamido-4-phenylsulfinyl-1-nitrobenzene is treated with 20 ml 5 N sodium hydroxide and 40 ml methanol at 20°-25°C for 1 h. Water is then added and essentially pure 2-amino-4-phenyl-sulfinyl-1-nitrobenzene filtered off. Recrystallization may be effected from benzene. 5.4 g of 2-amino-4-phenylsulfinyl-1-nitrobenzene is hydrogenated at 1 atmosphere pressure in 500 ml methanol in the presence of 5.0 g 5% palladized carbon, until the theoretical uptake of hydrogen has occurred. The catalyst is removed by filtration and the filtrate stripped under vacuum. The residue is recrystallized from methanol-benzene, yielding 1,2-diamino-4phenylsulfinylbenzene. A mixture of 5.5 g of 1,2-diamino-4-phenylsulfinylbenzene, 4.3 g of 1,3-bismethoxycarbonyl-S-methylisothiourea and 1.2 ml acetic acid in 100 ml ethanol and 100 ml water is refluxed for 4 h. The mixture is cooled and essentially pure 6-phenylsulfinyl-2-carbomethoxyaminobenzimidazole filtered off and washed with methanol. Recrystallization may be effected from methanol-chloroform (melting point 253°C, dec.).

Therapeutic Function

Anthelmintic

Safety Profile

Experimental reproductive effects. Human mutation data reported. Whenheated to decomposition it emits toxic fumes of SOx and NOx.

Veterinary Drugs and Treatments

Oxfendazole (Synanthic?) is indicated in cattle for the removal and control of lungworms, roundworms (including inhibited forms of Ostertagia ostertagi) and tapeworms. Oxfendazole as Benzelmin? was indicated (no longer marketed in the USA) for the removal of the following parasites in horses: large roundworms (Parascaris equorum), large strongyles (S. edentatus, S. equinus, S. vulgaris), small strongyles, and pinworms (Oxyuris equi). Oxfendazole has also been used extra-label in sheep, goats, and swine; see Dosage section for more information.

InChI:InChI=1/C15H13N3O3S/c1-21-15(19)18-14-16-12-8-7-11(9-13(12)17-14)22(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)

Upstream product

• 43210-67-9 Fenbendazole 

Downstream Products

• 104663-22-1 6-Benzenesulfinyl-2-methoxycarbonylamino-benzoimidazole-1-carboxylic acid methyl ester 
• 104663-01-6 1-carbomethoxy-2-carbomethoxyamino-5-phenylsulfinylbenzimidazole 
• 923672-38-2 C₁₆H₁₆N₃O₇PS 
• 923672-37-1 C₁₆H₁₆N₃O₇PS 

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