793. Arsenamide

Nomenclature

CAS number: 531-72-6
2,2′-[[[4-(Aminocarbonyl)phenyl]arsinidene]bis(thio)]bisacetic acid; [[(p-carbamoylphenyl)arsylene]dithio]diacetic acid; bis[carboxymethylmercapto](p-carbamylphenyl)-arsine; p-[bis(carboxymethylmercapto)arsino]benzamide; dithioglycolyl p-arsenobenzamide; 4-carbamylphenyl bis[carboxymethylthio]arsenite; thioarsenite; thiacetarsamide; Caparsolate (Abbott); Caparside.
C11H12AsNO5S2; mol wt 377.27.
C 35.02%, H 3.21%, As 19.86%, N 3.71%, O 21.20%, S 17.00%.

Description and references

Prepd by the condensation of p-arsenosobenzamide and thioglycolic acid: Gough, King J. Chem. Soc. 1930, 669; Maren, J. Am. Chem. Soc. 68, 1864 (1946).

Chemical structure

Properties

White crystalline powder. Sparingly sol in cold water; appreciably sol in water above 90°. Sparingly sol in cold methanol, ethanol; very sol in these solvents when they are warm. Insol in warm isopropyl ether. pKa = 4. The disodium salt is stoichiometrically formed in aq soln at pH 7-8.

Therapeutic Category (Veterinary)

Anthelmintic for heartworm infection in dogs, especially the adult worm.