Oxfendazole

Oxfendazole Basic information
Description References
Product Name:Oxfendazole
Synonyms:[5-(phenylsulfinyl)-1h-benzimidazol-2-yl]carbamic acid methyl ester;LODITAC;(5-(phenylsulfinyl)-1h-benzimidazol-2-yl)-carbamicacimethylester;5-(phenylsulfinyl)-2-benzimidazolecarbamicacidmethylester;5-(phenylsulfinyl)-2-benzimidazolecarbamicacimethylester;5-phenylsulfinyl-2-carbomethoxyaminobenzimidazole;OXFENDAZOLE;Oxfendazole BPV98
CAS:53716-50-0
MF:C15H13N3O3S
MW:315.35
EINECS:258-714-5
Product Categories:Amines, Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds;TICLID;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Sulfur & Selenium Compounds;Pharmaceutical intermediate;Metabolites;Veterinaries;53716-50-0
Mol File:53716-50-0.mol
Oxfendazole Structure
Oxfendazole Chemical Properties
Melting point 298-300?C
density 1.3229 (rough estimate)
refractive index 1.6740 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMF: slightly soluble; DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:4): 0.20 mg/ml
form neat
pka10.27±0.10(Predicted)
color Crystals from chloroform-methanol
Merck 14,6935
InChIKeyBEZZFPOZAYTVHN-UHFFFAOYSA-N
CAS DataBase Reference53716-50-0(CAS DataBase Reference)
Safety Information
Risk Statements 36
Safety Statements 26
WGK Germany 3
RTECS FD0835000
HS Code 29339900
ToxicityLD50 in dogs, rats, mice: >1600, >6400, >6400 mg/kg (Averkin)
MSDS Information
ProviderLanguage
SigmaAldrich English
Oxfendazole Usage And Synthesis
DescriptionOxfendazole 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.
Referenceshttps://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

Chemical PropertiesOf-White Solid
OriginatorAutoworm,Coopers
UsesA metabolite of Fenbendazole (F246750).
UsesPAF inhibitor
DefinitionChEBI: A member of the class of benzimidazoles that is fenbendazole in which the sulfur has been oxidised to the corresponding sulfoxide.
Manufacturing Process5.0 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 nameSynanthic Veterinary (Syntex).
Therapeutic FunctionAnthelmintic
Safety ProfileExperimental reproductive effects. Human mutation data reported. Whenheated to decomposition it emits toxic fumes of SOx and NOx.
Veterinary Drugs and TreatmentsOxfendazole (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.

Oxfendazole-D3(Fenbendazole sulfoxide-D3) oxfendazole sulfone Tablellae Oxfendazole Carbamic acid, 1H-benzimidazol-2-yl- (9CI) Methyl OXFENDAZOLE IMPURITY B FENBENDAZOLE SULPHOXIDE (OXFENDAZOLE) Methyl carbamate OXFENDAZOLE IMP. B (EP): METHYL [5-(PHENYLSULPHONYL)-1H-BENZIMIDAZOL-2-YL]CARBAMATE OXFENDAZOLE WITH IMPURITY D Granular Oxfendazole Oxfendazole Impurity C 1-n-butylcarbamoyl oxfendazole OXFENDAZOLE SULFOXIDE Omeprazole sodium sterile METHYL THIOPHENE-2-CARBOXYLATE OXFENDAZOLE FOR VETERINARY USE

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