43210-67-9 Usage
Benzimidazole anthelmintics
Fenbendazole is a benzimidazole anthelmintic with a broad spectrum,high efficiency and low toxicity ,in the structure,it has a strong affinity with the parasite tubulin ,by influencing cell transport and energy metabolism,it plays a role in preventing the polymerization of micro tubes, which ultimately destroys the integrity of parasite cells and energy transmission.
Fenbendazole is used to drive and to kill the animal gastrointestinal parasites, it not only has a highly anthelmintic activity on animal gastrointestinal roundworms, hookworms, whipworms, some tapeworms and nematodes , but also has a preferred effect on the part of the bronchial tree and lung parasites (Aelurostrongylus abstrutus and lung fluke) .
Aofendazuo
Aofendazuo is a benzimidazole anthelmintic, also known as the Austrian phenol metronidazole, oxfendazole, benzene etomidate sulfoxide, benzene sulfur oxygen imidazole ,it is the sulfoxide form of Fenbendazole , white or off-white powder at room temperature, slight special smell, it can damage the microtubules of the worms epithelial cells of the gastrointestinal tract, and inhibit the worms uptake of glucose from the intestine.
Aofendazuo is used for the treatment and control of gastrointestinal adults and larvae, it has a good effect on the treatment of in vivo roundworms and lung worms in pigs and sheep , including Oster nematodes (Ostertagia), Haemonchus , Trichostrongylus, Nematodirus , Cooper nematode (Cooperia), capillary nematodes (Capillaria), toothed Oesophagostomum (Oesophagostomum), Chabertia, Trichuris nematodes form (Trichuris) and dictyocaulasis ( Dictyocaulus) and so on.
The above information is edited by the lookchem of Tian Ye.
Chemical Properties
Different sources of media describe the Chemical Properties of 43210-67-9 differently. You can refer to the following data:
1. Gray light brown crystalline powder. Melting point 233 ℃ (decomposition). Soluble in dimethyl sulfoxide (DMSO), slightly soluble in common organic solvents, insoluble in water. Odorless, tasteless.
2. Off-White Solid
Uses
Different sources of media describe the Uses of 43210-67-9 differently. You can refer to the following data:
1. Anthelmintic. Broad-spectrum, high efficiency, low toxicity, antiparasitic. It has a strong killing effect on Roundworm, nematodes, tapeworms, cysticercosis , Fasciola and other parasites, not only killing worms, especially having a great effect on Transitional larvae ehich are hazardous to the liver, lungs and intestines .Fenbendazole is a benzimidazole anthelmintic, not only having a highly anthelmintic activity for gastrointestinal nematodes adults and larvae , but also having a good effect on dictyocaulasis, flukes and tapeworms, in addition,it has a strong killing eggs effect.
2. Fenbendazole is a benzimidazole anthelmintic that is metabolised in mammals to a series of other benzimidazoles including oxfendazole. It is used for the control of gastrointestinal roundworms, lung worms, Nematodes and tape worms. It is the only benzimidazole approved for use in organic livestock production.
Production method
5-chloro-2-nitroaniline reacts with benzene thiol, to thereby obtain 5-phenylthio-2-nitroaniline in 91% yield.Generate 3-phenylthio-o-phenylenediamine by ferrous sulfate-iron reduction in 90% yield. Finally, cyclize it with the S-methyl-melamine Methyl to obtain fenbendazole.
Description
Fenbendazole is a benzimidazole anthelmintic. It is active against Giardia in vitro (IC50 = 0.3 μM). Fenbendazole (20 mg/kg) prevents infiltration of parasites into the brain in a rabbit model of E. cuniculi infection. Fenbendazole also activates HIF-1α and prevents oxidative stress-induced death in primary neurons in vitro.
Originator
Panacur,Hoechst,W. Germany,1980
Definition
ChEBI: Fenbendazole is a member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections. It has a role as an antinematodal drug. It is a member of benzimidazoles, a carbamate ester and an aryl sulfide.
Manufacturing Process
20.9 g of S-methyl-thiourea were dissolved in 27 ml of water with 13.5 ml of
chloroformic acid methyl ester. Then, 45.7 ml of 25% sodium hydroxide
solution were added dropwise, while stirring, at a temperature of 5°C to 10°C.
After having stirred for 20 minutes, the reaction mixture was combined with 27 ml of glacial acetic acid, 100 ml of water and 29 g of 3,4-diaminodiphenyl-
thioether. Stirring was continued for 90 minutes at a temperature of
85°C, during which time methyl-mercaptan was separated. After having
allowed the whole to cool and stand overnight, the 5-phenylmercaptobenzimidazole-
2-methyl-carbamate that had formed was filtered off with
suction. After recrystallization from a mixture of glacial acetic acid and
methanol, 14 g of 4-phenylmercapto-benzimidazole-2-methyl-carbamate
melting at 233°C were obtained.
Brand name
Panacur (Hoechst-Roussel).
Therapeutic Function
Anthelmintic
General Description
Fenbendazole is a thio substituted benzimidazole, which belongs to the group of anthelmintics. It can be widely used in veterinary medicine particularly, in the treatment of helminth infections.
Veterinary Drugs and Treatments
Fenbendazole is indicated (labeled) for the removal of the following parasites in dogs: ascarids (Toxocara canis, T. leonina), Hookworms (Ancylostoma caninum, Uncinaria stenocephala), whipworms (Trichuris vulpis), and tapeworms (Taenia pisiformis). It is not effective against Dipylidium caninum. Fenbendazole has also been used clinically to treat Capillaria aerophilia, Filaroides hirthi, and Paragonimus kellicotti infections in dogs.Fenbendazole is indicated (labeled) for the removal of the following parasites in cattle: Adult forms of: Haemonchus contortus, Ostertagia ostertagi, Trichostrongylus axei, Bunostomum phlebotomum, Nematodirus helvetianus, Cooperia spp., Trichostrongylus colubriformis, Oesophagostomum radiatum, and Dictyocaulus vivaparus. It is also effective against most immature stages of the above listed parasites. Although not approved, it has good activity against Moniezia spp., and arrested 4th stage forms of Ostertagia ostertagi. Fenbendazole is indicated (labeled) for the removal of the following parasites in horses: large strongyles (S. edentatus, S. equinus, S. vulgaris), small strongyles (Cyathostomum spp., Cylicocylus spp., Cylicostephanus spp., Triodontophorus spp.), and pinworms (Oxyuris equi).Fenbendazole is indicated (labeled) for the removal of the following parasites in swine: large roundworms (Ascaris suum), lungworms (Metastrongylus pair), nodular worms (Oesphagostomum dentatum, O. quadrispinolatum), small stomach worms (Hyostrongylus rubidus), whipworms (Trichuris suis), and kidney worms (Stephanurus dentatus; both mature and immature).Although not approved, fenbendazole has been used in cats, sheep, goats, pet birds, and llamas.
Mode of action
Fenbendazole is a benzimidazole antiparasitic drug that works at the sub-cellular level preventing cell division. Benzimidazoles bind to the β-tubulin, inhibiting the cell’s microtubule assembly responsible for intracellular transport and required for mitotic cellular division. In effect, it starves the parasite by causing intestinal cell disruption.
Check Digit Verification of cas no
The CAS Registry Mumber 43210-67-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,3,2,1 and 0 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 43210-67:
(7*4)+(6*3)+(5*2)+(4*1)+(3*0)+(2*6)+(1*7)=79
79 % 10 = 9
So 43210-67-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)
43210-67-9Relevant articles and documents
Synthetic method of fenbendazole
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Paragraph 0035-0052, (2021/08/14)
A synthetic method of fenbendazole belongs to the technical field of insect repellents, and specifically comprises the following steps: carrying out condensation reaction on 5-chloro-2-nitroaniline and a sodium thiophenol aqueous solution in a mixed solution of n-propyl alcohol and water to obtain 5-thiophenyl-2-nitroaniline; carrying out reduction reaction on the 5-thiophenyl-2-nitroaniline in a high-pressure kettle under the catalysis of raney nickel to generate 4-thiophenyl o-phenylenediamine; and mixing the 4-thiophenyl o-phenylenediamine and N-(trichloromethyl) methyl carbamate for a cyclization reaction to obtain fenbendazole; the method has the advantages that conditions are mild, operation is easy and convenient, ammonium chloride can be prevented from being generated in the cyclization process, and the three-waste cost is low; the generation of amine salt is avoided, and the treatment cost of three wastes is greatly reduced; and the yield of the fenbendazole can reach 84.27% to 89.99%, and the purity of the fenbendazole can reach 96.39% to 99.71%.
A preparation method of a dog or CAT
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, (2019/03/29)
The invention discloses a dog or CAT a kind of preparation method. Characterized in that (1) in order to inter-bromobenzene as the starting material, nitric acid/sulfuric acid system through the nitration reaction, process for preparing the intermediate 1 (2, 4 - dibromo nitrobenzene); (2) using the intermediate 1 as raw materials, through the ammonia in methanol solution of ammoniation reaction, to prepare the intermediate 2 (5 - bromo - 2 - nitroaniline); (3) using the intermediate 2 and thiophenol sodium solution as raw materials, through the condensation reaction, process for preparing the intermediate 3 (4 - phenylthio - 2 - nitroaniline); (4) intermediate 3 through the palladium catalytic hydrogenation reduction, to produce intermediate 4 (4 - phenylthio - 1, 2 - phenylenediamine); (5) intermediate 4 and melamine-based methyl formate solution, through the cyclization reaction, the profuse benzene reaches zuo generating products. The method clean environment, the production cost is low, with a purity of 99.5% or more, the yield is not lower than 84.0%.
Efficient Synthesis in Three Steps and Spectral Determination of Methyl-5-[(o-, m-, and p-substituted-phenylthio]-2-Benzimidazolecarbamates
Cortes, Eduardo Cortes,Mendoza, Rafael Sosa,Gutierrez, Maximiliano Santibanez,De Cortes, Olivia Garcia-Mellado
, p. 273 - 276 (2007/10/03)
The preparation and spectral properties of ten novel methyl 5-[(o-, m-, and p-substituted)-phenylthio]-2-benzimidazolecarbamates with possible pharmacological activity as antihelmintics is described; by condensation and cyclization between 5-methylthioures sulfate chloroformic acid methyl ester and 3,4-diaminophenyl-substituted-phenylthio ether dissolved in ethanol. The structures of all final products were corroborated by ir; 1H-nmr, 13C-nmr and ms.
