topiramate   Click here for help

GtoPdb Ligand ID: 6849

Synonyms: epitomax | Eprontia® (liquid formulation) | MCN-4853 | RWJ-17021 | Topamax®
Approved drug PDB Ligand
topiramate is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: A multifunctional compound: inhibits carbonic anhydrases II and IV, positively modulates GABA-A receptor anion channels, blocks sodium channel alpha subunits and behaves as an antagonist at the ionotropic glutamate receptors (AMPA and kainate).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 123.92
Molecular weight 339.1
XLogP -1.2
No. Lipinski's rules broken 0
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Canonical SMILES NS(=O)(=O)OCC12OCC3C(C2OC(O1)(C)C)OC(O3)(C)C
Isomeric SMILES NS(=O)(=O)OC[C@]12OC[C@@H]3[C@H]([C@@H]2OC(O1)(C)C)OC(O3)(C)C
InChI 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
No information available.
Summary of Clinical Use Click here for help
Used to treat epilepsy in adults and children (including treatment of Lennox-Gastaut syndrome). Also used to prevent migraine. A combination product containing phentermine + extended-release topiramate may be used for the management of obesity (n.b. the EMA refused approval of this combination for this indication in May 2013).

Two small randomized, placebo-controlled pilot studies suggested that the GABA potentiating action of topiramate may be harnessed as a treatment to help reduce alcohol intake in problem drinkers [1], and as a smoking cessation aid [3].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
An anticonvulsant drug; enhances GABA-activated chloride channels and inhibits excitatory neurotransmission, through actions on kainate and AMPA receptors.
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