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 Y
PubChem CID	4622
ChemSpider	4461 N
UNII	022N12KJ0X
KEGG	D05293 Y
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) N Key:RAOCRURYZCVHMG-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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

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

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.