Flubendazole

Chemical Name Methyl-N-[5(6)-p-fluorobenzoyl-2-benzImidazolyl] carbamate Common Name — 

To a stirred and cooled (ice bath) suspension of 25 parts of aluminum chloride in 52 parts of fluorobenzene is added dropwise a solution of 27.5 parts of 4-chloro-3-nitrobenzoyl chloride in 52 parts of fluorobenzene. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto water and the product is extracted with methylene chloride. The extract is washed successively with sodium hydrogen carbonate solution and water, dried, filtered and evaporated in vacuo. The solid residue is crystallized from 2-propanol, yielding 4-chloro-4 -fluoro-3-nitrobenzophenone MP 975°C. 

A mixture of 24.5 parts of 4-chloro-4 -fluoro-3-nitrobenzophenone, 72 parts of methanol, 

13 parts of sulfolane and 3.12 parts of ammonia is heated in a sealed tube for 20 hours at 120°C. To the reaction mixture is added successively 50 parts of water and 25 parts of a diluted hydrochloric acid solution and the whole is stirred and refluxed for 5 minutes. The reaction mixture Is cooled and the precipitated product is filtered off. It is washed with 2-propanol and recrystallized from 640 parts of toluene, yielding4-amino-4 -fluoro-3-nitro-benzophenone MP 199°C. 

A mixture of 14.5 parts of 4-amino-4 -fluoro-3-nitroben2ophenone, 160 parts of methanol. 

6 parts of concentrated hydrochloric acid solution and 0.5 part of platinum oxide is hydrogenated at normal pressure and at room temperature. After the calculated amount of hydrogen is taken up, hydrogenation is stopped. The catalyst is filtered off and the filtrate is evaporated. The residue Is washed with 2-propanol and dried, yielding 3,4-diamino-4 -fluorobenzo-phenone hydrochloride MP 226°C to 230.5°C. 

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Ferroglycine sulfate Ferrous fumarate Fluoranthene Flora ntyrone Fluoroacetyl chloride Afloqualone p-Fluorobenzaldehyde Sulindac Fluorobenzene Flubendazole o-Fluorobenzoyl chloride Flunitrazepam... 

QH5F 462-06-6) see Bromperidol Flubendazole Haloperidol Suprofen 4-fluorobenzenesulfonyl chloride (CftH4ClF02S 349-88-2) see Ramatroban 4-fluorobenzonitrile... 

Flubendazole (70) belongs in this chemical class and is synthesized by similar methods but its bioactivity is expressed as an antiprotozoal agent. 

Albendazole Bromoxanide Bunamidine Cambedazole Clioxanide Cyclobendazole Flubendazole Lobendazole Antihistaminics Mebendazole Niclosamide Nitramisole Nitrodan Oxantel Oxfendazole Oxibendazole Thenium Closylate... 

Trichinosis Trichinella spiralis Steroids for severe symptoms plus Thiabendazole, Albendazole, Flubendazole-, or Mebendazole-... 

AntihBiminticS Flubendazole was launched as an antihelmintic. It seems to have a mode of action close to that of benzimidazole derivatives used as antihelmintics mebendazole, albendazole), which are reported to block the capture of glucose by the parasite (Figure 8.23). 

Flubendazole Fluvermal, Flicum, Flumoxal, Fluverval, Fluvermox... 

Flubendazole is used against gastrointestinal nematodes and lungworms in swine and poultry at dosages of 5 mg/kg bw or 30 ppm in the feed. This anthelminthic is poorly absorbed from the gut and, therefore, exhibits low toxicity. 

Unlike mebendazole, flubendazole which is its halogenated analogue, produces only one-tenth of the plasma levels attained with mebendazole. When swine or poultry are treated with flubendazole, the tissue with the highest residues concentration and the slowest depletion rate is the liver. Residues in swine liver are primarily composed of the (2-amino-lH-benzimidazol-5-yl)-4-fluorophenyl-methanone metabolite, which is generally found at a much higher concentration than die parent drug. 

Residue depletion studies in sows receiving 30 mg flubendazole/kg bw in die feed for 10 days showed that the mean concentrations of the unchanged flubendazole in liver, kidney, muscle, and fat were 59,67,13, and 33 ppb, respectively, 7 days after cessation of the treatment (4). 

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