Fenbendazole

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Structural formula
Structural formula of fenbendazole
General
Non-proprietary name Fenbendazole
other names

Methyl [5- (phenylsulfanyl) -1H-benzimidazol-2-yl] carbamate ( IUPAC )

Molecular formula C 15 H 13 N 3 O 2 S
External identifiers / databases
CAS number 43210-67-9
EC number 256-145-7
ECHA InfoCard 100.051.024
PubChem 3334
ChemSpider 3217
Wikidata Q908013
Drug information
ATC code

Q P52AC13

Drug class

Anthelmintic

Mechanism of action

Microtubule inhibitor

properties
Molar mass 299.35 g mol −1
Physical state

firmly

Melting point

233 ° C

solubility

bad in water

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 1000 mg kg −1 ( LD 50ratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fenbendazole is a broad spectrum anthelmintic from the benzimidazole group . It is used in veterinary medicine as an agent against endoparasites . Combination preparations with praziquantel are also available.

Mechanism of action

Fenbendazole has a broad spectrum of activity against roundworms (nematodes) and tapeworms (cestodes). It works relatively slowly, so that a sufficiently long contact time with the worm must be guaranteed. The remedy is therefore less effective in animals with rapid intestinal transit ( carnivores ).

Like all benzimidazoles, fenbendazole binds to tubulin , a protein subunit of the microtubules , the parasite cell (microtubule inhibitor). This causes damage to the cytoskeleton , which disrupts intracellular transport and synthesis processes (especially glucose transport and ATP synthesis). The parasite starves and dies and is excreted with the feces. By inhibiting the development of the spindle apparatus and disrupting the metabolism during embryogenesis, the agent also acts against the egg cells of worms (ovozid).

Tapeworms damage the suction structures, so that the parasites detach themselves from the intestinal wall after four to eight hours and are finally excreted in the feces.

Fenbendazole is hardly absorbed in the intestine.

The agent works against all relevant nematodes. In addition, it is also effective against some species of the real tapeworms ( genera Taenia and Monezia ), liver fluke , trichinae and giardia as well as against Encephalitozoon cuniculi .

Contraindications and side effects

Pregnant animals should not be treated with fenbendazole, especially its use in early pregnancy is contraindicated. In birds it should not be used during the change of feathers ( moulting ).

The agent is very well tolerated, even a tenfold overdose usually remains symptom-free. In domestic dogs and cats , vomiting can rarely occur as a side effect. In domestic pigeons , feathering damage can occur when used in the Mauser.

Trade names

  • Monopreparations : Ascapilla +, Coglazol, Fenbendatat, Feligel (except for trade), Fenbenol, Gallifen, Meranox, Orystor, Panacur, Pigfen, Verminth (except for trade)
  • Combination preparations with Praziquantel : aniprazol KH, Bihelminth mv, Caniquantel, Fenprasel, Fenquantel, Optivermin-Kombi, Prazifen-Kombi, Vermis-Ex, Worm Stop

See also

Individual evidence

  1. a b Entry on fenbendazole at Vetpharm, accessed on November 21, 2011.
  2. a b c Datasheet Fenbendazole from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).