Fenbendazole
Systematic (IUPAC) name | |
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methyl N-(6-phenylsulfanyl-1H-benzoimidazol-
2-yl)carbamate |
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Clinical data | |
AHFS/Drugs.com | International Drug Names |
Identifiers | |
CAS Number | 43210-67-9 |
ATC code | P02CA06 (WHO) QP52AC13 (WHO) |
PubChem | CID: 3334 |
ChemSpider | 3217 |
UNII | 621BVT9M36 |
KEGG | D04140 |
ChEBI | CHEBI:77092 |
ChEMBL | CHEMBL37161 |
Chemical data | |
Formula | C15H13N3O2S |
Molecular mass | 299.349 g/mol |
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Fenbendazole (Hoechst brand names Panacur and Safe-Guard, Intervet Panacur and Panacur Rabbit) is a broad spectrum benzimidazole anthelmintic used against gastrointestinal parasites including: giardia, roundworms, hookworms, whipworms, the Taenia genus of tapeworms (but not effective against Dipylidium caninum, a common dog tapeworm), pinworms, aelurostrongylus, paragonimiasis, strongyles and strongyloides and can be administered to sheep, cattle, horses, fish, dogs, cats, rabbits and seals. Drug interactions may occur if salicylanilides like dibromsalan and niclosamide are co-administered. Abortions in cattle and death in sheep have been reported.[1]
Toxicity
Despite being widely used as a dewormer in many species, toxicity has been reported. Birds (storks, pink pelicans, vultures, pigeons and doves) and reptiles (vipers, turtles and tortoises) have shown toxicity associated with bone marrow suppression, intestinal crypt cell necrosis and distal villi sloughing.[citation needed] Abortions in domestic ruminants have been associated with concurrent use of anti-trematode therapeutic agents.[citation needed]
Fenbendazole is poorly absorbed from the gastrointestinal tract in most species. The LD50 in laboratory animals exceeds 10 g/kg when administered orally.[1]
Synthesis
Metabolism
It gets metabolized in the liver to oxfendazole, which is anthelmintic too; oxfendazole partially gets reduced back to fenbendazole in the liver and rumen.[4][5] Also, fenbendazole itself is an active metabolite of another anthelmintic drug, febantel.[6]
See also
References
- ↑ 1.0 1.1 Plumb's Veterinary Drug Handbook, Fifth Edition, 2005.
- ↑ H. Loewe et al., DE 2164690; eidem, U.S. Patent 3,954,791 (1973, 1976 both to Hoechst)
- ↑ C. Baeder et al., Experientia 30, 753 (1974).
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External links
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- Chemical articles having calculated molecular weight overwritten
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- Articles with unsourced statements from July 2010
- Anthelmintics
- Thioethers
- Benzimidazoles
- Carbamates
- Antiinfective agent stubs