An internal standard for the quantification of topiramate
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Unlabeled Version(s)
13623Topiramate
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Topiramate-d12

Item No. 26443

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3:4,5-bis-O-[1-(methyl-d3)ethylidene-2,2,2-d3]-β-D-fructopyranose, 1-sulfamate
CAS Number
1279037-95-4
Synonyms
  • TPM-d12
Molecular Formula
C12H9D12NO8S
Formula Weight
351.4
Purity
≥99% deuterated forms (d1-d12)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 15 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 0.1 mg/ml
SMILES
NS(OC[C@]12[C@@H](OC(C([2H])([2H])[2H])(C([2H])([2H])[2H])O2)[C@H]3[C@H](OC(C([2H])([2H])[2H])(C([2H])([2H])[2H])O3)CO1)(=O)=O
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/i1D3,2D3,3D3,4D3
InChi Key
KJADKKWYZYXHBB-RFYKXYJISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

    $129

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    5 mg

    $535

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    10 mg

    $868

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    Product Description

    Topiramate-d12 is intended for use as an internal standard for the quantification of topiramate (Item No. 13623) by GC- or LC-MS. 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).