Topiramate
Title: Topiramate
CAS Registry Number: 97240-79-4
CAS Name: 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate
Additional Names: 2,3:4,5-di-O-isopropylidene-b-D-fructopyranose sulfamate
Manufacturers' Codes: McN-4853; RWJ-17021-000
Trademarks: Topamax (J & J)
Molecular Formula: C12H21NO8S
Molecular Weight: 339.36
Percent Composition: C 42.47%, H 6.24%, N 4.13%, O 37.72%, S 9.45%
Literature References: Sulfamate substituted monosaccharide; structurally distinct antiepileptic agent. Prepn: B. E. Maryanoff, J. F. Gardocki, US 4513006 (1985 to McNeil); and anticonvulsant activity: B. E. Maryanoff et al., J. Med. Chem. 30, 880 (1987). GC determn in plasma: M. L. Holland et al., J. Chromatogr. 433, 276 (1988). Comparative pharmacokinetics: M. Bialer, Clin. Pharmacokinet. 24, 441 (1993). Series of articles on pharmacology and clinical experience in epilepsy: Epilepsia 38, Suppl. 1, 1-62 (1997). Review of clinical trials in migraine prevention: G. Bussone et al., Int. J. Clin. Pract. 59, 961-968 (2005); of pharmacology and clinical experience: S. D. Silberstein et al., Clin. Ther. 27, 154-165 (2005).
Properties: Crystals from ethyl acetate + hexane, mp 125-126°. [a]D23 -34.0° (c = 0.4 in methanol).
Melting point: mp 125-126°
Optical Rotation: [a]D23 -34.0° (c = 0.4 in methanol)
Therap-Cat: Anticonvulsant; antimigraine.
Keywords: Anticonvulsant; Antimigraine.

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