flubendazole
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 407194173
| IUPAC_name = Methyl N-[6-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate
| image = Flubendazole.svg
| width = 225
| tradename =
| Drugs.com = {{drugs.com|international|flubendazole}}
| DailyMedID = Flubendazole
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
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| routes_of_administration =
| bioavailability =
| protein_bound =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 31430-15-6
| ATC_prefix = P02
| ATC_suffix = CA05
| ATC_supplemental = {{ATCvet|P52|AC12}}
| PubChem = 35802
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB08974
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = R8M46911LR
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04200
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 77095
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 145946
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 32932
| C=16 | H=12 | F=1 | N=3 | O=3
| solubility = 10.0 ± 0.4 × 10−6 μg/mL (pH 1.6); 0.29 ± 0.06 × 10−6 μg/mL (pH 6.5)
| smiles = COC(=O)Nc1[nH]c2ccc(cc2n1)C(=O)c3ccc(cc3)F
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CPEUVMUXAHMANV-UHFFFAOYSA-N
}}
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 atom.{{cite journal | vauthors = Heyer F, Tourte-Schaeffer C, Ancelle T, Faurant C, Lapierre J |title=Le flubendazole : un progrès dans le traitement des helminthiases intestinales. A propos de 471 observations |journal=Médecine et Maladies Infectieuses |date=1 February 1982 |volume=12 |issue=2 |pages=57–61 |doi=10.1016/S0399-077X(82)80047-4 |url=https://www.sciencedirect.com/science/article/pii/S0399077X82800474 |language=fr |issn=0399-077X}}
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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){{cite web |title=FLUVERMAL |url=https://www.vidal.fr/medicaments/gammes/fluvermal-3835.html |website=VIDAL |access-date=31 January 2023 |language=fr}} under the brand name Fluvermal as an alternative to mebendazole which is not currently sold there.{{cite web |title=VERMOX |url=https://www.vidal.fr/medicaments/gammes/vermox-28317.html |website=VIDAL |language=fr}}
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.{{cite patent | country = US | number = 5824336 | title = Chewable flubendazole tablets for companion animals | inventor = Jozef EM, Gilis JP | assign1 = Jannsen Pharmaceuticals | gdate = 20 October 1998 }}
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'.{{cite web|title=Best practice use of medicated grit|url=http://www.gwct.org.uk/advisory/guides/medicated-grit-best-practice/|website=Game and Wildlife Conservation Trust|access-date=27 September 2016}} 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.{{cite web| vauthors = Kay P |title=Analysis, occurrence and effects of flubendazole in moorland river catchments|url=http://www.nercdtp.leeds.ac.uk/projects/index.php?id=527|website=www.nercdtp.leeds.ac.uk|publisher=Leeds York NERC Doctoral Training Partnership (DTP)|access-date=11 January 2017}}{{cite journal| vauthors = Kreuzig R, Blümlein K, Höltge S |title=Fate of the Benzimidazole Antiparasitics Flubendazole and Fenbendazole in Manure and Manured Soils|journal=CLEAN – Soil, Air, Water|date=November 2007|volume=35|issue=5|pages=488–494|doi=10.1002/clen.200720023|bibcode=2007CSAW...35..488K |url=https://www.researchgate.net/publication/227792944|access-date=11 January 2017}}