Fenbendazole

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Fenbendazole
Fenbendazole.svg
Clinical data
AHFS/Drugs.com International Drug Names
License data
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 InfoCard 100.051.024 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H13N3O2S
Molar mass 299.35 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) Yes check.svgY
  • Key:HDDSHPAODJUKPD-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Fenbendazole (also known as Fenben) 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 that can be administered to sheep, cattle, horses, fish, dogs, cats, rabbits, most reptiles, freshwater shrimp tanks as planaria and hydra treatments, as well as seals. [1]

Contents

Drug interactions

Drug interactions may occur if salicylanilides such as dibromsalan and niclosamide are co-administered. Abortions in cattle and death in sheep have been reported after using these medications together. [2] Abortions in domestic ruminants have been associated with concurrent use of anti-trematode therapeutic agents. [3]

Toxicity

Fenbendazole is poorly absorbed from the gastrointestinal tract in most species. The LD50 in laboratory animals exceeds 10 g/kg when administered orally. [2] Given its low toxicity and high tolerability among different species, the possibility of repurposing it as a drug to treat cancer in humans has been proposed. [4]

Metabolism

Fenbendazole is metabolized in the liver to oxfendazole, which is anthelmintic too; oxfendazole partially gets reduced back to fenbendazole in the liver and rumen. [5] [6] Also, fenbendazole itself is an active metabolite of another anthelmintic drug, febantel. [7]

See also

Related Research Articles

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<i>Haemonchus contortus</i> Species of roundworm

Haemonchus contortus, also known as the barber's pole worm, is a very common parasite and one of the most pathogenic nematodes of ruminants. Adult worms attach to abomasal mucosa and feed on the blood. This parasite is responsible for anemia, oedema, and death of infected sheep and goats, mainly during summer in warm, humid climates.

<span class="mw-page-title-main">Tiabendazole</span> Chemical compound

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<i>Toxocara canis</i> Species of roundworm

Toxocara canis is a worldwide-distributed helminth parasite that primarily infects dogs and other canids, but can also infect other animals including humans. The name is derived from the Greek word "toxon," meaning bow or quiver, and the Latin word "caro," meaning flesh. T. canis live in the small intestine of the definitive host. This parasite is very common in puppies and somewhat less common in adult dogs. In adult dogs, infection is usually asymptomatic but may be characterized by diarrhea. By contrast, untreated infection with Toxocara canis can be fatal in puppies, causing diarrhea, vomiting, pneumonia, enlarged abdomen, flatulence, poor growth rate, and other complications.

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<i>Toxocara cati</i> Species of worm

Toxocara cati, also known as the feline roundworm, is a parasite of cats and other felids. It is one of the most common nematodes of cats, infecting both wild and domestic felids worldwide. Adult worms are localised in the gut of the host. In adult cats, the infection – which is called toxocariasis – is usually asymptomatic. However, massive infection in juvenile cats can be fatal.

<span class="mw-page-title-main">Listeriosis in animals</span>

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<span class="mw-page-title-main">Deworming</span> Use of anthelmintic drugs

Deworming is the giving of an anthelmintic drug to a human or animals to rid them of helminths parasites, such as roundworm, flukes and tapeworm. Purge dewormers for use in livestock can be formulated as a feed supplement that is eaten, a paste or gel that is deposited at the back of the animal's mouth, a liquid drench given orally, an injectable, or as a pour-on which can be applied to the animal's topline. In dogs and cats, purge dewormers come in many forms including a granular form to be added to food, pill form, chew tablets, and liquid suspensions.

ATCvet code QP52Anthelmintics is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System for veterinary medicinal products, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products for veterinary use. Subgroup QP52 is part of the anatomical group QP Antiparasitic products, insecticides and repellents.

<span class="mw-page-title-main">Anthelmintic</span> Antiparasitic drugs that expel parasitic worms (helminths) from the body

Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may also be called vermifuges or vermicides. Anthelmintics are used to treat people who are infected by helminths, a condition called helminthiasis. These drugs are also used to treat infected animals.

<span class="mw-page-title-main">Nitroscanate</span> Chemical compound

Nitroscanate is an anthelmintic drug used in veterinary medicine to treat Toxocara canis, Toxascaris leonina, Ancylostoma caninum, Uncinaria stenocephala, Taenia, and Dipylidium caninum.

Moniezia expansa is commonly known as sheep tapeworm or double-pored ruminant tapeworm. It is a large tapeworm inhabiting the small intestines of ruminants such as sheep, goats and cattle. It has been reported from Peru that pigs are also infected. There is an unusual report of human infection in an Egyptian. It is characterized by unarmed scolex, presence of two sets of reproductive systems in each proglottid, and each proglottid being very short but very broad.

<span class="mw-page-title-main">Oxfendazole</span> Chemical compound

Oxfendazole is a broad spectrum benzimidazole anthelmintic. Its main use is for protecting livestock against roundworm, strongyles and pinworms. Oxfendazole is the sulfoxide metabolite of fenbendazole.

<i>Cooperia oncophora</i> Species of roundworm

Cooperia oncophora is one of the most common intestinal parasitic nematodes in cattle in temperate regions. Infections with C. oncophora may result in mild clinical symptoms, but can lead to weight loss and damage of the small intestine, especially when co-infections with other nematodes such as O. ostertagi occur. Infections are usually treated with broad-spectrum anthelmintics such as benzimidazole, but resistance to these drugs has developed in the last decades and is now very common. C. oncophora has a direct life cycle. Infective larvae are ingested by the host. The larvae grow to adults, which reproduce in the small intestines. Eggs are shed onto the pasture with the faeces, which leads to new infections. Co-infections with other gastro-intestinal nematodes such as O. ostertagi and H. contortus are common.

<span class="mw-page-title-main">Nitroxinil</span> Chemical compound

Nitroxinil is an anthelmintic, a veterinary medicine against parasitic worms in sheep and cattle. The substance is active against the liver fluke the Fasciola hepatica and to a lesser extent against thread worms in the gastrointestinal tract. Brand names include Fluconix, Dovenix and Trodax. Nitroxynil is also used against strains of the red gum worm that have become resistant to benzimidazoles.

References

  1. "Fenbendazole: From MD Anderson to Joe Tippens". Institute of Integrative BioOncology. Retrieved 2023-10-19.
  2. 1 2 Plumb DC (2005). Plumb's veterinary drug handbook (Fifth ed.). Stockholm, Wis.: PhrmaVet. ISBN   978-0-8138-0518-4.
  3. Sarangi LN, Tharani N, Polapally S, Rana SK, Thodangala N, Bahekar VS, et al. (March 2021). "Infectious bovine abortions: observations from an organized dairy herd". Brazilian Journal of Microbiology. 52 (1): 439–448. doi:10.1007/s42770-020-00414-x. PMC   7966683 . PMID   33415719.
  4. Dogra N, Kumar A, Mukhopadhyay T (August 2018). "Fenbendazole acts as a moderate microtubule destabilizing agent and causes cancer cell death by modulating multiple cellular pathways". Scientific Reports. 8 (1): 11926. Bibcode:2018NatSR...811926D. doi:10.1038/s41598-018-30158-6. PMC   6085345 . PMID   30093705. Fenbendazole is known to have a high safety margin and most species tolerate it very well. It has very low degree of toxicity and high degree of safety in experimental animals. In this study, we show that fenbendazole (FZ) exhibits a moderate microtubule depolymerizing activity towards human cancer cells, but possesses a potent antitumor effect as evident from in vitro and in vivo experiments.
  5. 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.
  6. 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.
  7. 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.