Oxibendazole

Oxibendazole
Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QP52AC07 (WHO) ;
Legal status
Legal status	Veterinary use only;
Identifiers
	IUPAC name Methyl N-(6-propoxy-1H-benzimidazol-2-yl)carbamate;
CAS Number	20559-55-1 ;
PubChem CID	4622;
ChemSpider	4461 ;
UNII	022N12KJ0X;
KEGG	D05293 ;
CompTox Dashboard (EPA)	DTXSID5045625 ;
ECHA InfoCard	100.039.873
Chemical and physical data
Formula	C12H15N3O3
Molar mass	249.270 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCOC1=CC2=C(C=C1)N=C(N2)NC(=O)OC;
	InChI InChI=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) ; Key:RAOCRURYZCVHMG-UHFFFAOYSA-N ;
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Oxibendazole is a benzimidazole drug that is used to protect against roundworms, strongyles, threadworms, pinworms and lungworm infestations in horses and some domestic pets.[1][2] It is usually white to yellowish in appearance, and may take the form of a powder, tablet or paste.

Synthesis

Oxibendazole synthesis:[3]

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

References

Theodorides VJ, Chang J, DiCuollo CJ, Grass GM, Parish RC, Scott GC (December 1973). "Oxibendazole, a new broad spectrum anthelmintic effective against gastrointestinal nematodes of domestic animals". The British Veterinary Journal. 129 (6): xcontdvii–scvi. doi:10.1016/s0007-1935(17)36351-0. PMID 4779247.
Bowman DD (2009). "Chapter 6: Anti-parasitic Drugs". Georgis' parasitology for veterinarians (9th ed.). St. Louis, Mo.: Saunders/Elsevier. p. 280. ISBN 978-1-4160-4412-3.
GB 1123317, "Anthelmintic compositions containing benzimidazole derivatives", published 1968-08-14, assigned to Smith Kline French Labs; US 3574845, Actor PP, Pagano JF, "Anthelmintic compositions and methods employing esters of benzimidazolyl carbamic acids and their thio analogs", issued 13 April 1971, assigned to Smith Kline and French Laboratories Ltd

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[Theodorides_1973-1] Theodorides VJ, Chang J, DiCuollo CJ, Grass GM, Parish RC, Scott GC (December 1973). "Oxibendazole, a new broad spectrum anthelmintic effective against gastrointestinal nematodes of domestic animals". The British Veterinary Journal. 129 (6): xcontdvii–scvi. doi:10.1016/s0007-1935(17)36351-0. PMID 4779247.

[2] Bowman DD (2009). "Chapter 6: Anti-parasitic Drugs". Georgis' parasitology for veterinarians (9th ed.). St. Louis, Mo.: Saunders/Elsevier. p. 280. ISBN 978-1-4160-4412-3.

[3] GB 1123317, "Anthelmintic compositions containing benzimidazole derivatives", published 1968-08-14, assigned to Smith Kline French Labs; US 3574845, Actor PP, Pagano JF, "Anthelmintic compositions and methods employing esters of benzimidazolyl carbamic acids and their thio analogs", issued 13 April 1971, assigned to Smith Kline and French Laboratories Ltd