20559-55-1 Usage
Description
Oxibendazole is a broad-spectrum anthelmintic agent belonging to the benzimidazole class of compounds. It is a crystalline solid with potent nematicidal and insecticidal properties, making it effective against various gastrointestinal parasites in animals and humans. Oxibendazole works by inhibiting the synthesis of tubulin, which disrupts the metabolism and growth of helminths, ultimately leading to their death.
Uses
Used in Veterinary Medicine:
Oxibendazole is used as an anthelmintic agent for the treatment and control of various gastrointestinal nematodes, lungworms, and arthropod parasites in livestock animals, such as cattle, sheep, and horses. It is effective against both adult and larval stages of parasites, providing comprehensive protection against infections.
Used in Human Medicine:
Oxibendazole is also used as an anthelmintic agent in human medicine, targeting a wide range of intestinal helminths, including roundworms, hookworms, and whipworms. It is particularly useful in treating infections caused by Trichuris trichiura, Ancylostoma duodenale, and Necator americanus.
Used as an Alcohol and Narcotic Antagonist:
In addition to its anthelmintic properties, Oxibendazole has been found to possess alcohol and narcotic antagonist activity. It has been used in the treatment of alcohol dependence, helping to reduce cravings and withdrawal symptoms. Furthermore, it has shown potential in the management of opioid dependence, aiding in the reduction of drug-seeking behavior and relapse prevention.
Chemical Properties:
Oxibendazole is a crystalline solid with a unique chemical structure that contributes to its anthelmintic and antagonistic properties. Its benzimidazole structure allows it to bind to and inhibit the enzyme tubulin, which is essential for the growth and reproduction of helminths.
Brand Names:
Some of the brand names under which Oxibendazole is marketed include Anthelcide EQ (SmithKline Beecham Animal Health) and Filaribits Plus (SmithKline Beecham Animal Health). These formulations are specifically designed for the treatment of parasitic infections in animals, ensuring effective and targeted therapy.
Biochem/physiol Actions
Anthelminthic
Veterinary Drugs and Treatments
Oxibendazole is indicated (labeled) for the removal of the following
parasites in horses: large roundworms (Parascaris equorum), large
strongyles (S. edentatus, S. equinus, S. vulgaris), small strongyles,
threadworms, and pinworms (Oxyuris equi).
Oxibendazole has also been used in cattle, sheep, and swine; see
Dosage section for more information.
Check Digit Verification of cas no
The CAS Registry Mumber 20559-55-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,5,5 and 9 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 20559-55:
(7*2)+(6*0)+(5*5)+(4*5)+(3*9)+(2*5)+(1*5)=101
101 % 10 = 1
So 20559-55-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
20559-55-1Relevant articles and documents
2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of polysubstituted o-phenylenediamines and their conversion into heterocycles, particularly 2-substituted benzimidazoles with known or potential anthelminthic activity
Hazelton,Iddon,Suschitzky,Woolley
, p. 10771 - 10794 (2007/10/02)
Polysubstituted o-phenylenediamines were synthesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio- and 2-trifluoro-methylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)-benzimidazole and 11-(pyridin-2-ylthio)dibenzo[a,c]phenazine were synthesized too. Attempts to oxidise 1,3-dihydro-2H-4,9-diazanaphth[2,3-d]imidazole, prepared by condensation of 2,3-diaminoquinoxaline with cyclohexanone, to an analogue of the title system failed.
SYNTHESIS AND REACTIONS OF 2H-BENZIMIDAZOLE-2-SPIROCYCLOHEXANES : AN APPLICATION OF "UMPOLING"
Iddon, Brian
, p. 673 - 701 (2007/10/02)
The title compounds are available through condensation of an o-phenylenediamine with cyclohexanone followed by oxidation of the resulting product with manganese dioxide.In this article we review their oxidation, reduction, and rearrangement reactions along with their reactions with nitrogen, oxygen, sulphur, and other nucleophiles.As well as the parent compound the reactions of the 5-chloro-, 5,6-dichloro-, 4,6-dibromo-, 5-phenylsulphonyl- and 5-methoxy-derivative are discussed in some detail.Some applications of the methodology developed, particularly to the synthesis of actual or potential benzimidazole anthelminthics, are given also.
