Oxibendazole: Difference between revisions

{{Short description|Chemical compound}}

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| verifiedrevid = 447186723

| IUPAC_name = Methyl ''N''-(6-propoxy-1''H''-benzimidazol-2-yl)carbamate

| image = Oxibendazole.svg

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| legal_status = Veterinary use only

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| ChemSpiderID = 4461

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| C=12 | H=15 | N=3 | O=3

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C12H15N3O3/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = RAOCRURYZCVHMG-UHFFFAOYSA-N

'''Oxibendazole''' is a [[benzimidazole]] drug that is used to protect against [[roundworm]]s, [[strongyle (worm)|strongyles]], [[Strongyloides stercoralis|threadworms]], [[pinworm]]s and [[lungworm]] infestations in horses and some domestic pets.<ref name="Theodorides_1973">{{cite journal | vauthors = Theodorides VJ, Chang J, DiCuollo CJ, Grass GM, Parish RC, Scott GC | title = Oxibendazole, a new broad spectrum anthelmintic effective against gastrointestinal nematodes of domestic animals | journal = The British Veterinary Journal | volume = 129 | issue = 6 | pages = xcontdvii–scvi | date = December 1973 | pmid = 4779247 | doi = 10.1016/s0007-1935(17)36351-0 }}</ref><ref>{{cite book | vauthors = Bowman DD |page = 280 | chapter = Chapter 6: Anti-parasitic Drugs | chapter-url = https://books.google.com/books?id=g_tBWVBevM0C&pg=PA280 |title=Georgis' parasitology for veterinarians. |date=2009 |publisher=Saunders/Elsevier |location=St. Louis, Mo. |isbn=978-1-4160-4412-3 |edition=9th}}</ref> It is usually white to yellowish in appearance, and may take the form of a powder, tablet or paste.

==Synthesis==

[[File:Oxibendazole synthesis.svg|thumb|upright=3|center|Oxibendazole synthesis:<ref>{{Cite patent|country=GB|number=1123317|title=Anthelmintic compositions containing benzimidazole derivatives|pubdate=1968-08-14|assign1 = Smith Kline French Labs}}; {{cite patent | country = US | number = 3574845 | inventor = Actor PP, Pagano JF | assign1 = Smith Kline and French Laboratories Ltd | title = Anthelmintic compositions and methods employing esters of benzimidazolyl carbamic acids and their thio analogs | gdate = 13 April 1971 }}</ref>]]{{clear left}}

4‑Hydroxyacetamide ('''1''') is alkylated with [[1-bromopropane|''n''-propyl bromide]] in the presence of [[potassium hydroxide]] to give the [[ether]] ('''2'''). Nitration of this product with [[nitric acid|nitric]] and [[sulfuric acid]]s proceeds at the position [[Arene substitution pattern|''ortho'']] to the [[amide]] group ('''3'''), which is then reduced with [[tin(II) chloride|SnCl₂]] to yield the [[phenylenediamine]] derivative ('''4'''). Reaction of that intermediate with [[thiourea|''S''-methyl isothiourea]] proceeds first by [[aromatization|aromatic cyclisation]] to the [[guanidine]] derivative followed by [[elimination reaction|elimination]] of [[methyl mercaptan]] to yield the 2-aminobenzimidazole system ('''5'''). Acylation with [[methyl chloroformate]] results in the formation of a [[carbamate|urethane]] on the amino group to produce oxibendazole ('''6''').

{{Anthelmintics}}

[[Category:Veterinary drugs]]

{{antiinfective-drug-stub}}

{{veterinary-med-stub}}