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Fenbendazole

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Fenbendazole
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • Methyl N-(6-phenylsulfanyl-1H-benzoimidazol-2-yl)carbamate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.051.024 Edit this at Wikidata
Chemical and physical data
FormulaC15H13N3O2S
Molar mass299.349 g/mol g·mol−1
3D model (JSmol)
  • COC(=O)Nc3nc2ccc(Sc1ccccc1)cc2[nH]3
  • InChI=1S/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) checkY
  • Key:HDDSHPAODJUKPD-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Fenbendazole is a broad spectrum benzimidazole anthelmintic used against gastrointestinal parasites including: giardia, roundworms, hookworms, whipworms, the tapeworm genus Taenia (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 after using these medications together.[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]

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.[2][3] Also, fenbendazole itself is an active metabolite of another anthelmintic drug, febantel.[4]

See also

References

  1. ^ a b Plumb's Veterinary Drug Handbook, Fifth Edition, 2005.
  2. ^ Junquera, P. (2015-07-26). "FENBENDAZOLE, anthelmintic for veterinary use on CATTLE, SHEEP, GOATS, PIG, POULTRY, HORSES, DOGS and CATS against roundworms and tapeworms". PARASITIPEDIA. Retrieved 2015-09-08.
  3. ^ Junquera, P. (2015-07-26). "OXFENDAZOLE, anthelmintic for veterinary use on CATTLE, SHEEP, GOATS, HORSES, DOGS and CATS against roundworms and tapeworms". PARASITIPEDIA. Retrieved 2015-09-08.
  4. ^ Junquera, P. (2015-07-26). "FEBANTEL for veterinary use on DOGS, CATS, CATTLE, SHEEP, GOATS, PIG and POULTRY against roundworms and tapeworms". PARASITIPEDIA. Retrieved 2015-09-08.