Flubendazole

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Flubendazole
Flubendazole.svg
Clinical data
AHFS/Drugs.com International Drug Names
License data
ATC code
Identifiers
  • Methyl N-[6-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
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ChEBI
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ECHA InfoCard 100.046.007 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H12FN3O3
Molar mass 313.288 g·mol−1
3D model (JSmol)
Melting point 243 [1]  °C (469 °F)
Solubility in water 10.0 ± 0.4 × 10−6 μg/mL (pH 1.6); 0.29 ± 0.06 × 10−6 μg/mL (pH 6.5) [1]  mg/mL (20 °C)
  • COC(=O)Nc1[nH]c2ccc(cc2n1)C(=O)c3ccc(cc3)F
  • InChI=1S/C16H12FN3O3/c1-23-16(22)20-15-18-12-7-4-10(8-13(12)19-15)14(21)9-2-5-11(17)6-3-9/h2-8H,1H3,(H2,18,19,20,22) X mark.svgN
  • Key:CPEUVMUXAHMANV-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Flubendazole is an anthelmintic, used both in humans and for veterinarian purposes. It is very close chemically to mebendazole, the only difference being an added fluorine group. [2]

Contents

Human use

It is available for human use to treat worm infections. In certain countries such as France, it is inexpensive and available OTC (without prescription) [3] under the brand name Fluvermal as an alternative to mebendazole which is not currently sold there. [4]

Veterinarian use

Under veterinary use, its brand name is Flutelmium which is a paste manufactured by Janssen Pharmaceutica N.V. used by veterinarians for protection against internal parasites and worms in dogs and cats. Other brand names are Flubenol, Biovermin, and Flumoxal. [5]

Since 2000, Flubendazole-treated grit has increasingly been laid out on a landscape-scale across many UK grouse-shooting moors by gamekeepers in an attempt to reduce the impact on bird numbers from strongyle worm. Evidence of high worm burden is required before a veterinarian can dispense and sell the product, known as 'medicated grit'. [6] However, there has been increasing concern about contaminants entering the ground waters running off from moorlands, as well as from its use in farming environments and its presence in manure. Researchers are starting to gather research evidence in order to inform policy development on the presence of this and other veterinary medicines in the wider environment. [7] [8]

Related Research Articles

<i>Trichuris trichiura</i> Parasitic roundworm that causes intestinal infection

Trichuris trichiura, Trichocephalus trichiuris or whipworm, is a parasitic roundworm that causes trichuriasis when it infects a human large intestine. It is commonly known as the whipworm which refers to the shape of the worm; it looks like a whip with wider "handles" at the posterior end.

<span class="mw-page-title-main">Trichuriasis</span> Infection by Trichuris trichiura (whipworm)

Trichuriasis, also known as whipworm infection, is an infection by the parasitic worm Trichuris trichiura (whipworm). If infection is only with a few worms, there are often no symptoms. In those who are infected with many worms, there may be abdominal pain, fatigue and diarrhea. The diarrhea sometimes contains blood. Infections in children may cause poor intellectual and physical development. Low red blood cell levels may occur due to loss of blood.

<span class="mw-page-title-main">Ascariasis</span> Disease caused by the parasitic roundworm Ascaris lumbricoides

Ascariasis is a disease caused by the parasitic roundworm Ascaris lumbricoides. Infections have no symptoms in more than 85% of cases, especially if the number of worms is small. Symptoms increase with the number of worms present and may include shortness of breath and fever in the beginning of the disease. These may be followed by symptoms of abdominal swelling, abdominal pain, and diarrhea. Children are most commonly affected, and in this age group the infection may also cause poor weight gain, malnutrition, and learning problems.

<span class="mw-page-title-main">Praziquantel</span> Medication

Praziquantel (PZQ), sold under the brandname Biltricide among others, is a medication used to treat a number of types of parasitic worm infections in mammals, birds, amphibians, reptiles, and fish. In humans specifically, it is used to treat schistosomiasis, clonorchiasis, opisthorchiasis, tapeworm infections, cysticercosis, echinococcosis, paragonimiasis, fasciolopsiasis, and fasciolosis. It should not be used for worm infections of the eye. It is taken by mouth.

<span class="mw-page-title-main">Abamectin</span> Insecticide and anti-parasitic worm chemical

Abamectin (also called avermectin B1) is a widely used insecticide and anthelmintic. Abamectin, is a member of the avermectin family and is a natural fermentation product of soil dwelling actinomycete Streptomyces avermitilis. Abamectin differs from ivermectin, the popular member of the avermectin family, by a double bond between carbons 22 and 25. Fermentation of Streptomyces avermitilis yields eight closely related avermectin homologs, with the B1a and B1b forms comprising the majority of the fermentation. The non-proprietary name, abamectin, refers to a mixture of B1a (~80%) and B1b (~20%). Out of all the avermectins, abamectin is the only one that is used both in agriculture and pharmaceuticals.

<span class="mw-page-title-main">Hookworm infection</span> Disease caused by intestinal parasites

Hookworm infection is an infection by a type of intestinal parasite known as a hookworm. Initially, itching and a rash may occur at the site of infection. Those only affected by a few worms may show no symptoms. Those infected by many worms may experience abdominal pain, diarrhea, weight loss, and tiredness. The mental and physical development of children may be affected. Anemia may result.

<span class="mw-page-title-main">Ivermectin</span> Medication for parasite infestations

Ivermectin is an antiparasitic drug. After its discovery in 1975, its first uses were in veterinary medicine to prevent and treat heartworm and acariasis. Approved for human use in 1987, it is used to treat infestations including head lice, scabies, river blindness (onchocerciasis), strongyloidiasis, trichuriasis, ascariasis and lymphatic filariasis. It works through many mechanisms to kill the targeted parasites, and can be taken by mouth, or applied to the skin for external infestations. It belongs to the avermectin family of medications.

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

Tiabendazole, also known as thiabendazole or TBZ and the trade names Mintezol, Tresaderm, and Arbotect, is a preservative, an antifungal agent, and an antiparasitic agent.

<span class="mw-page-title-main">Mebendazole</span> Medication for parasitic worm infestations

Mebendazole (MBZ), sold under the brand name Vermox among others, is a medication used to treat a number of parasitic worm infestations. This includes ascariasis, pinworm infection, hookworm infections, guinea worm infections, hydatid disease, and giardia, among others. It is taken by mouth.

Uncinaria stenocephala is a nematode that parasitizes dogs, cats, and foxes as well as humans. It is rare to find in cats in the United States. Uncinaria stenocephala is the most common canine hookworm in cooler regions, such as Canada and the northern regions of the US, where it can be found primarily in foxes (40%). U. stenocephala is also one of the most common hookworms in the UK, called the northern hookworm, however it has a rather low prevalence. U. stenocephala is also considered to be zoonotic hookworms because they live in animals but can be transmitted to humans.

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

Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections. It is taken by mouth.

A veterinary pharmacist is a specially trained pharmacist who dispenses veterinary drugs and supplies or products and advice to owners of companion animals and livestock. In addition, they advise the regulatory bodies and are involved in the formulation of veterinary drugs. Veterinary pharmacy is a field of pharmacy practice, in which veterinary pharmacists may compound medications, fill prescriptions, and manage drug therapies for animals. Veterinary pharmacists are licensed pharmacists who specialize in the distribution of medications for animals.

Necatoriasis is the condition of infection by Necator hookworms, such as Necator americanus. This hookworm infection is a type of helminthiasis (infection) which is a type of neglected tropical disease.

<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.

<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.

<span class="mw-page-title-main">Pinworm infection</span> Medical condition

Pinworm infection, also known as enterobiasis, is a human parasitic disease caused by the pinworm, Enterobius vermicularis. The most common symptom is itching in the anal area. The period of time from swallowing eggs to the appearance of new eggs around the anus is 4 to 8 weeks. Some people who are infected do not have symptoms.

<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">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.

Children Without Worms (CWW) is a program of the Task Force for Global Health and envisions a world in which all at-risk people, specifically targeting children, are healthy and free of worm infections (helminthiases) so they can develop to their full potential. To accomplish the vision of a worm-free world, CWW works closely with the World Health Organization, national Ministries of Health, nongovernmental organizations and private-public coalitions such as Uniting to Combat NTDs. It acts as an intermediary for the pharmaceutical company Johnson and Johnson in distributing the latter's mebendazole for mass deworming of children to reduce or end soil-transmitted helminthiasis.

<span class="mw-page-title-main">Mass deworming</span> Treating large numbers of people for helminthiasis and schistosomiasis

Mass deworming, is one of the preventive chemotherapy tools, used to treat large numbers of people, particularly children, for worm infections notably soil-transmitted helminthiasis, and schistosomiasis in areas with a high prevalence of these conditions. It involves treating everyone – often all children who attend schools, using existing infrastructure to save money – rather than testing first and then only treating selectively. Serious side effects have not been reported when administering the medication to those without worms, and testing for the infection is many times more expensive than treating it. Therefore, for the same amount of money, mass deworming can treat more people more cost-effectively than selective deworming. Mass deworming is one example of mass drug administration.

References

  1. 1 2 Vasilev NA, Voronin AP, Surov AO, Perlovich GL (March 2023). "Influence of Co-amorphization on the Physical Stability and Dissolution Performance of an Anthelmintic Drug Flubendazole". Molecular Pharmaceutics. 20 (3): 1657–1669. doi:10.1021/acs.molpharmaceut.2c00873. PMID   36732935. S2CID   256546280.
  2. Heyer F, Tourte-Schaeffer C, Ancelle T, Faurant C, Lapierre J (1 February 1982). "Le flubendazole : un progrès dans le traitement des helminthiases intestinales. A propos de 471 observations". Médecine et Maladies Infectieuses (in French). 12 (2): 57–61. doi:10.1016/S0399-077X(82)80047-4. ISSN   0399-077X.
  3. "FLUVERMAL". VIDAL (in French). Retrieved 31 January 2023.
  4. "VERMOX". VIDAL (in French).
  5. US 5824336,Jozef EM, Gilis JP,"Chewable flubendazole tablets for companion animals",issued 20 October 1998, assigned to Jannsen Pharmaceuticals
  6. "Best practice use of medicated grit". Game and Wildlife Conservation Trust. Retrieved 27 September 2016.
  7. Kay P. "Analysis, occurrence and effects of flubendazole in moorland river catchments". www.nercdtp.leeds.ac.uk. Leeds York NERC Doctoral Training Partnership (DTP). Retrieved 11 January 2017.
  8. Kreuzig R, Blümlein K, Höltge S (November 2007). "Fate of the Benzimidazole Antiparasitics Flubendazole and Fenbendazole in Manure and Manured Soils". CLEAN – Soil, Air, Water. 35 (5): 488–494. Bibcode:2007CSAW...35..488K. doi:10.1002/clen.200720023 . Retrieved 11 January 2017.