Fenbendazole

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Fenbendazole
Fenbendazole.svg
Systematic (IUPAC) name
methyl N-(6-phenylsulfanyl-1H-benzoimidazol-
2-yl)carbamate
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 43210-67-9 YesY
ATC code P02CA06 QP52AC13
PubChem CID 3334
ChemSpider 3217 YesY
UNII 621BVT9M36 YesY
KEGG D04140 YesY
ChEBI CHEBI:77092 N
ChEMBL CHEMBL37161 YesY
Chemical data
Formula C15H13N3O2S
Molar mass 299.349 g/mol
 NYesY (what is this?)  (verify)

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[edit]

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[edit]

Fenbendazole synthesis[2][3]

Metabolism[edit]

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[edit]

References[edit]

  1. ^ a b Plumb's Veterinary Drug Handbook, Fifth Edition, 2005.
  2. ^ H. Loewe et al., DE 2164690 ; eidem, U.S. Patent 3,954,791 (1973, 1976 both to Hoechst)
  3. ^ C. Baeder et al., Experientia 30, 753 (1974).
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 

External links[edit]