2409. Clorsulon

Nomenclature

CAS number: 60200-06-8
4-Amino-6-(trichloroethenyl)-1,3-benzenedisulfonamide; 4-amino-6-(trichlorovinyl)-m-benzenedisulfonamide; MK-401; Curatrem (Merial).
C8H8Cl3N3O4S2; mol wt 380.66.
C 25.24%, H 2.12%, Cl 27.94%, N 11.04%, O 16.81%, S 16.85%.

Description and references

Benzenedisulfonamide deriv with fasciolicidal activity. Prepn: H. H. Mrozik, DE 2556122 (1976 to Merck & Co.), C.A. 85, 94100n (1976); H. Mrozik et al., J. Med. Chem. 20, 1225 (1977). GLC determn in biological fluids: W. J. A. Vanden Heuvel et al., J. Agric. Food Chem. 25, 389 (1977). Efficacy against liver fluke, Fasciola hepatica: D. A. Ostlind et al., Br. Vet. J. 133, 211 (1977); M. D. Schulman et al., J. Parasitol. 65, 555 (1979). In vitro inhibition of glycolysis: M. D. Schulman, D. Valentino, Exp. Parasitol. 49, 206 (1980). Mechanism of action: M. D. Schulman et al., Mol. Biochem. Parasitol. 5, 133 (1982). Pharmacokinetics: eidem, J. Parasitol. 68, 603 (1982).

Chemical structure

Properties

Crystals from ether, mp 194-203°. Another crystal form from water, mp 203-205°. uv max (CH3OH): 325, 267, 227 nm (ε 4530, 17395, 36310). LD50 in mice (mg/kg): 761 i.p.; >10,000 orally (Ostlind).

Therapeutic Category (Veterinary)

Anthelmintic (Trematodes).