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	249.26 g/mol 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. It is usually white to yellowish in appearance, and may take the form of a powder or a tablet.

Synthesis

[[File:Oxibendazole synthesis.svg|thumb|center|700px|Oxibendazole synthesis:^[1] 4-Hydroxyacetamide is alkylated with n-propylbromide in the presence of KOH to give the ether (2). Nitration of the product with HNO3/H2SO4 proceeds at the position ortho to the amido group (3); saponification followed by reduction of the nitro group with SnCl₂gives the phenylenediamine (4). Then it is converted to the 2-aminobenzimidazole system by S-methylthiourea and subsequently acylated by methyl chloroformate to product 6.

References

^ GB 1123317 corresp to P. P. Actor, J. F. Pagano, U.S. patent 3,574,845 (1968, 1971 both to SKF).]]

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[1] GB 1123317 corresp to P. P. Actor, J. F. Pagano, U.S. patent 3,574,845 (1968, 1971 both to SKF).]]

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