CHEBI:63631 - topiramate

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ChEBI Name topiramate
ChEBI ID CHEBI:63631
Definition A hexose derivative that is 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose in which the hydroxy group has been converted to the corresponding sulfamate ester. It blocks voltage-dependent sodium channels and is used as an antiepileptic and for the prevention of migraine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:9633
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Formula C12H21NO8S
Net Charge 0
Average Mass 339.36200
Monoisotopic Mass 339.099
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
InChIKey KJADKKWYZYXHBB-XBWDGYHZSA-N
SMILES CC1(C)O[C@@H]2CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@H]3[C@@H]2O1
Roles Classification
Biological Role(s): sodium channel blocker
An agent that inhibits sodium influx through cell membranes.
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
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ChEBI Ontology
Outgoing topiramate (CHEBI:63631) has role anticonvulsant (CHEBI:35623)
topiramate (CHEBI:63631) has role sodium channel blocker (CHEBI:38633)
topiramate (CHEBI:63631) is a cyclic ketal (CHEBI:59779)
topiramate (CHEBI:63631) is a ketohexose derivative (CHEBI:63391)
topiramate (CHEBI:63631) is a sulfamate ester (CHEBI:48199)
INNs Sources
topiramate ChemIDplus
topiramato ChemIDplus
topiramatum ChemIDplus
Synonyms Sources
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate ChemIDplus
2,3:4,5-di-O-isopropylidene-β-D-fructopyranose sulfamate ChemIDplus
McN-4853 ChemIDplus
RWJ-17021 ChemIDplus
tipiramate DrugBank
tipiramato DrugBank
Topiramate KEGG COMPOUND
TPM ChEBI
Brand Name Source
Topamax DrugBank
Database Links Databases
2706 DrugCentral
C07502 KEGG COMPOUND
D00537 KEGG DRUG
DB00273 DrugBank
LSM-5435 LINCS
Topiramate Wikipedia
TOR PDBeChem
US4513006 Patent
View more database links
Registry Numbers Types Sources
5988957 Reaxys Registry Number Reaxys
97240-79-4 CAS Registry Number KEGG COMPOUND
97240-79-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22233396 PubMed citation Europe PMC
22249827 PubMed citation Europe PMC
Last Modified
22 February 2017