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
1. Kranzler HR, Covault J, Feinn R, Armeli S, Tennen H, Arias AJ, Gelernter J, Pond T, Oncken C, Kampman KM. (2014)
Topiramate treatment for heavy drinkers: moderation by a GRIK1 polymorphism.
Am J Psychiatry, 171 (4): 445-52. [PMID:24525690]
2. Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. (2005)
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.
Bioorg Med Chem Lett, 15 (17): 3828-33. [PMID:16039848]
3. Oncken C, Arias AJ, Feinn R, Litt M, Covault J, Sofuoglu M, Kranzler HR. (2014)
Topiramate for smoking cessation: a randomized, placebo-controlled pilot study.
Nicotine Tob Res, 16 (3): 288-96. [PMID:24057996]
4. Sethi KK, Vullo D, Verma SM, Tanç M, Carta F, Supuran CT. (2013)
Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety.
Bioorg Med Chem, 21 (19): 5973-82. [PMID:23965175]
5. Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastoreková S, Supuran CT. (2005)
Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs?.
Bioorg Med Chem Lett, 15 (4): 963-9. [PMID:15686894]