Topiramate, 托吡酯, 妥泰

2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate

Topiramate is a sugar sulfamate with anticonvulsant activity. It inhibits carbonic anhydrase in intact human erythrocytes (Ki = ~200 μM), as well as blocks sodium and calcium channels and kainate-induced currents in vitro. It also increases GABAA receptor-mediated chloride ion flux. Topiramate inhibits hind-limb tonic-extensor seizures in the maximal electroshock seizure test in mice (ED50 = 39 mg/kg, p.o.). Formulations containing topiramate have been used in the treatment of epilepsy and prophylaxis of migraine headaches.

Topiramate, a sulfamate-substituted derivative of the monosaccharide D-fructose, is a medication, which is widely used for the treatment of epilepsy.

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.