The Stereochemical Basis of Anticonvulsant Drug Action. V. The Crystal and Molecular Structure of Sulthiame

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Abstract
The crystal and molecular structure of sulthiame, (N-[4′-sulfamylphenyl]-l,4-butansultam), one of a series of carbonic anhydrase inhibitors that have gained wide use as antiepileptic agents, has been determined in order to compare the stereochemistry of this compound to that of other antiepileptics. Crystals of sulthiame are orthorhombic, space group Pca21; with cell dimensions a = 8.267, b = 17.750, c = 8.651 Å. The structure was determined by Patterson and Fourier methods and refined to a final R value of 0.039.Sulthiame molecular conformation differs markedly from that of diphenylhydantoin and other anticonvulsant drugs, suggesting a different mechanism of action for this compound. If the sulfonamide group is removed from sulthiame, however, the resulting molecule, although no longer a carbonic anhydrase inhibitor, does retain weak antiepileptic activity and does bear a weak conformational resemblance to the other noncarbonic anhydrase inhibitor anticonvulsant drugs.

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