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
• Article Data: 5

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

Description

Oxfendazole is a broad spectrum benzimidazole anthelmintic approved for veterinary use. It is effective to protect livestock and poultry from most of the parasites such as roundworms, tapeworms, strongyles and pinworms. The drug is mainly applied in the form of pills, tables, drenches and bolus, etc. especially for horses, goats, cattle, sheep, etc. The drug functions on parasites by binding to tubulin, which is a structural protein of microtubules. In the parasites the blocking of microtubules interferes with the uptake of glucose, which ultimately empties the glycogen reserves. This blocks the whole energy management mechanism of the parasites and eventually leads to death.

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

Uses

Different sources of media describe the Uses of 53716-50-0 differently. You can refer to the following data:
1. A metabolite of Fenbendazole (F246750).
2. PAF inhibitor

Definition

ChEBI: A member of the class of benzimidazoles that is fenbendazole in which the sulfur has been oxidised to the corresponding sulfoxide.

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.).

Brand name

Synanthic Veterinary (Syntex).

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

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

Relevant articles and documents

Catalyst-free visible light-mediated selective oxidation of sulfides into sulfoxides under clean conditions

A facile and efficient visible-light-mediated method for directly converting sulfides into sulfoxides under clean conditions without using any photocatalysts is reported. This method exhibited favourable compatibility with functional groups and afforded a series of sulfoxides with high selectivity and yields. Moreover, in order to shed more light on such a transformation, detailed mechanism studies were carried out both experimentally and theoretically. The readily accessible, low-cost and eco-friendly nature of the developed method will endow it with attractive applications in chemical synthesis.

1,5-diphenyl-3-formazancarbonitril parasiticides

The present invention is directed to the use of 1,5-diaryl-3 -formazancarbonitrile compounds for the control of parasites in vertebrate animals.

Method of treating helminthiasis by parenteral administration of sulfoxide derivatives of benzimidazoles

A method is provided for treating or inhibiting helminthiasis by parenterally administering sulfoxide derivatives of benzimidazoles having the structure STR1 wherein R1 is lower alkyl or phenyl-lower alkyl, and R2 is hydrogen, lower alkyl, halogen, lower alkoxy or nitro. Pharmaceutical compositions for use in the above method are also provided.