topiramate   Click here for help

GtoPdb Ligand ID: 6849

Synonyms: epitomax | 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
SMILES / InChI / InChIKey
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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
InChI Key KJADKKWYZYXHBB-XBWDGYHZSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
IUPAC Name Click here for help
[(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate
International Nonproprietary Names Click here for help
INN number INN
6099 topiramate
Synonyms Click here for help
epitomax | MCN-4853 | RWJ-17021 | Topamax®
Database Links Click here for help
CAS Registry No. 97240-79-4
ChEBI CHEBI:63631
ChEMBL Ligand CHEMBL220492
DrugBank Ligand DB00273
DrugCentral Ligand 2706
GtoPdb PubChem SID 178103455
PubChem CID 5284627
RCSB PDB Ligand TOR
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SynPHARM 79189 (in complex with carbonic anhydrase 1)
Wikipedia Topiramate

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Tocris
Topiramate
Cat. No. 3620