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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Topiramate

Cayman Chemical Item Number 13623

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

Topiramate (CAS 97240-79-4)

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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
  • McN 4853
  • Epitomax
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
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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

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).

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).

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Size Price Quantity Subtotal
50 mg $50.00 $0.00
100 mg $95.00 $0.00
500 mg $400.00 $0.00
1 g $700.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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