An anticonvulsant
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Labeled Version(s)
26443Topiramate-d12
Metabolite(s)
350714,5-Desisopropylidene Topiramate
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Topiramate

Item No. 13623

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose, 1-sulfamate
CAS Number
97240-79-4
Synonyms
  • McN 4853
  • RWJ 17021
  • TPM
Molecular Formula
C12H21NO8S
Formula Weight
339.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 15 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 0.15 mg/ml
SMILES
CC1(C)O[C@H]2[C@H]3[C@H](OC(C)(C)O3)CO[C@@]2(COS(N)(=O)=O)O1
InChi Code
InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1
InChi Key
KJADKKWYZYXHBB-XBWDGYHZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    Topiramate is a sugar sulfamate with anticonvulsant activity.1 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.1,2,3 It also increases GABAA receptor-mediated chloride ion flux.3 Topiramate inhibits hind-limb tonic-extensor seizures in the maximal electroshock seizure test in mice (ED50 = 39 mg/kg, p.o.).1 Formulations containing topiramate have been used in the treatment of epilepsy and prophylaxis of migraine headaches.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(5), 880-887 (1987).

    2. Greenfield, L.J., Jr. Molecular mechanisms of antiseizure drug activity at GABAA receptors. Seizure 22(8), 589-600 (2013).

    3. Rosenfeld, W.E. Topiramate: A review of preclinical, pharmacokinetic, and clinical data. Clin. Ther. 19(6), 1294-1308 (1997).