Anticonvulsant O-Alkyl Sulfamates. 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose Sulfamate and Related Compounds.

Article abstract of DOI:10.1021/jm00388a023

Novel sugar sulfamate 1 (McN-4853, topiramate) has been found to exhibit potent anticonvulsant activity analogous to that of phenytoin.In the maximal electroshock seizure test, orally at 2 h in mice, 1 had an ED50 of 39 mg/kg.Orally, 1 had a duration of action in excess of 8 h.Other aspects of the pharmacology of 1, as well as neurochemistry and carbonic anhydrase inhibition, are discussed.The conformational behavior of 1 in solution and in the solid state are discussed.A series of analogues of 1 were synthesized and examined for anticonvulsant properties.