Flubendazole

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Structural formula
Structural formula of flubendazole
General
Non-proprietary name Flubendazole
other names

Methyl- (5- (4-fluorobenzoyl) -1 H -benzimidazol-2-yl) carbamate ( IUPAC )

Molecular formula C 16 H 12 FN 3 O 3
External identifiers / databases
CAS number 31430-15-6
EC number 250-624-4
ECHA InfoCard 100.046.007
PubChem 35802
ChemSpider 32932
DrugBank DB08974
Wikidata Q241992
Drug information
ATC code

Q P52AC12

Drug class

Anthelmintic

Mechanism of action

Microtubule inhibitor

properties
Molar mass 313.28 g · mol -1
Physical state

firmly

Melting point

260 ° C

solubility

almost insoluble in alcohol, inorganic acids and 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
07 - Warning 08 - Dangerous to health

danger

H and P phrases H: 361-302
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Flubendazole is a drug from the group of benzimidazoles . It is a p-fluorinated analogue of mebendazole . Flubendazole is used as an agent against endoparasites ( anthelmintic ).

Mechanism of action

Flubendazole 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 parasite must be guaranteed. The remedy is therefore less effective in animals with rapid intestinal transit ( carnivores ).

Like all benzimidazoles, flubendazole binds to tubulin , a protein subunit of the microtubules , the parasite cell (microtubule inhibitor). This leads to damage to the cytoskeleton , as a result of which intracellular transport and synthesis processes are disrupted (especially glucose transport, 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).

Flubendazole is hardly absorbed in the intestine.

Spectrum of activity

In the case of oral administration, flubendazole is administered over two to three days for domestic dogs and house cats . The agent is effective against hookworms ( Ancylostoma caninum , Uncinaria stenocephalum ), dwarf threadworms ( Strongyloides ssp.), Roundworms ( Toxocara canis , Toxascaris leonina , Toxocara cati ), whipworms ( Trichuris ssp.) And real tapeworms of the genus Taenia . In dogs infected with heartworms ( Dirofilaria immitis ), the active ingredient is administered subcutaneously over 5 days .

Flubendazole can also be used against planarians (Dugesia tigrina) and hydra (Cnidaria) in the aquarium. It is mixed into the water and left to work for 7 days (no water change). The application should be repeated after 3–4 weeks. When using it in the aquarium, it should be noted that the active ingredient is toxic to snails even in low concentrations. Even months after use, many species of snails can still die from residues despite repeated water changes. This has a negative effect on the biological balance in the aquarium. It can also affect the fertility of shrimp.

Contraindications and side effects

The agent is very well tolerated, even strong overdosing have no consequences. The oral LD 50 for mice is over 2560 mg kg −1 .

Trade names

Cananthel, Flimabend, Flimabo, Flubendavet, Flubenol, Fluvermal, Frommex, Solubenol, Vermicat

See also

Individual evidence

  1. ↑ a b Entry on flubendazole at Vetpharm, accessed on August 4, 2012.
  2. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of flubendazole in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on January 13, 2020, is reproduced from a self-classification by the distributor .

Web links