Topiramate

Topiramate

Cayman Chemical Item Number 13623

TPM; Topamax^®; RWJ 17021; Epitomax; McN 4853 (CAS 97240-79-4)

Topiramate (CAS 97240-79-4)

Description

Topiramate is a sugar sulfamate that exhibits potent anticonvulsant activity. It completely blocks seizures (ED₅₀ = 39 mg/kg when given orally) in mice in the maximal electroshock seizure test.^1,2 This effect is sustained for over eight hours.^1,2 In the rotoreel test of neurotoxicity, topiramate has a peak neurotoxic dose ED₅₀ value of 407 mg/kg in mice at one hour.¹ It is virtually inactive against seizures caused by pentylenetetrazol, bicuculline, picrotoxin, and strychnine. It does not bind to norepinephrine, serotonin, γ-amino butyric acid, muscarinic, or dopamine receptors.^1,2 The drug form of Topiramate, Topamax^®, is used alone or with other medications to treat seizures associated with epilepsy and to prevent migraine headaches.^3,4

1 Maryanoff, B.E., Nortey, S.O., Gardocki, J.F., et al. Anticonvulsant O-alkyl sulfamates. 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate and related compounds. J Med Chem 30 880-887 (1987).

2 Shank, R.P., Gardocki, J.F., Vaught, J.L., et al. Topiramate: Preclinical evaluation of a structurally novel anticonvulsant. Epilepsia 35(2) 450-460 (1994).

3 Ben-Menachem, E., Sander, J.W., Stefan, H., et al. Topiramate monotherapy in the treatment of newly or recently diagnosed epilepsy. Clin Ther 30(7) 1180-1195 (2008).

4 Ruiz, L., and Ferrandi, D. Topiramate in migraine progression. J Headache Pain 10 419-422 (2009).

Synonyms

TPM
Topamax®
RWJ 17021
Epitomax
McN 4853

Formal Name

2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose 1-sulfamate

CAS Number

97240-79-4

Molecular Formula

C₁₂H₂₁NO₈S

Formula Weight

339.4

Formulation

A crystalline solid

Purity

≥98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

CC1(C)O[C@H]2[C@H]3[C@H](OC(C)(C)O3)CO[C@@]2(COS(N)(=O)=O)O1

Background Reading

Ruiz, L., and Ferrandi, D. Topiramate in migraine progression. J Headache Pain 10 419-422 (2009).

Ben-Menachem, E., Sander, J.W., Stefan, H., et al. Topiramate monotherapy in the treatment of newly or recently diagnosed epilepsy. Clin Ther 30(7) 1180-1195 (2008).

Maryanoff, B.E., Nortey, S.O., Gardocki, J.F., et al. Anticonvulsant O-alkyl sulfamates. 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate and related compounds. J Med Chem 30 880-887 (1987).

Shank, R.P., Gardocki, J.F., Vaught, J.L., et al. Topiramate: Preclinical evaluation of a structurally novel anticonvulsant. Epilepsia 35(2) 450-460 (1994).

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Topiramate (CAS 97240-79-4)

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Topiramate

Topiramate (CAS 97240-79-4)

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