10192. Zonisamide

Nomenclature

CAS number: 68291-97-4
1,2-Benzisoxazole-3-methanesulfonamide; 3-(sulfamoylmethyl)-1,2-benzisoxazole; AD-810; CI-912; Excegran (Dainippon); Zonegran (Dainippon).
C8H8N2O3S; mol wt 212.23.
C 45.27%, H 3.80%, N 13.20%, O 22.62%, S 15.11%.

Description and references

Sulfonamide antiseizure agent; blocks repetitive firing of voltage-sensitive sodium channels and reduces voltage-sensitive T-type calcium currents. Prepn: H. Uno et al., JP Kokai 78 77057; eidem, US 4172896 (1978, 1979 both to Dainippon); eidem, J. Med. Chem. 22, 180 (1979). Pharmacology and toxicity: Y. Masuda et al., Arzneim.-Forsch. 30, 477 (1980). Mode of action study: T. Ito et al., ibid. 603. HPLC determn in serum: U. Juergens, J. Chromatogr. 385 233 (1987). Clinical trial in epilepsy: D. Schmidt et al., Epilepsy Res. 15, 67 (1993); in Parkinson's Disease: M. Murata et al., Neurology 68, 45 (2007). Review of neuropharmacology: E. J. Hammond et al., Gen. Pharmacol. 18, 303 (1987); of pharmacokinetics and therapeutic potential: D. H. Peters, E. M. Sorkin, Drugs 45, 760-787 (1993); of pharmacokinetics and mechanism of action: I. E. Leppik, Seizure 13S, S5-S9 (2004).

Chemical structure

Properties

White needles from ethyl acetate, mp 160-163° (Uno); also reported as mp 162-166° (Masuda, 1980). pKa 10.2. Soly (mg/ml): water 0.80; 0.1 N HCl 0.50. Sparingly sol in chloroform, n-hexane. Sol in methanol, ethanol, ethyl acetate, and acetic acid. LD50 in mice, rats (mg/kg): 1892, 2001 orally; 1273, 2569 s.c.; 699, 733 i.p.; 604, 748 i.v. (Masuda, 1980).

Therapeutic Category

Anticonvulsant.

Therapeutic Category (Veterinary)

Anticonvulsant.

Keywords

Anticonvulsant