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T0575 Sigma

Topiramate

≥98% (HPLC), solid

Synonym: 2,3:4,5-Bis-O-(1-methylethylidene)-36-D-fructo-pyranose sulfamate, McN 4853, RWJ 17021, Topamax

  • CAS Number 97240-79-4

  • Empirical Formula (Hill Notation) C12H21NO8S

  • Molecular Weight 339.36

  •  MDL number MFCD00865320

  •  PubChem Substance ID 24724627

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
InChI Key   KJADKKWYZYXHBB-XBWDGYHZSA-N
assay   ≥98% (HPLC)
form   solid
color   white
solubility   DMSO: 40 mg/mL
originator   Johnson & Johnson
storage temp.   2-8°C
Gene Information   human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768)
mouse ... Car5a(12352)
rat ... Car2(54231), Car4(29242)

Description

Biochem/physiol Actions

Kainate GluR5 receptor antagonist; anticonvulsant.

Topiramate is a derivative of suphamate fructopyranose that inhibits the release of mesocorticolimbic dopamine. It facilitates GABA activity and inhibits glutamate function to alleviate the rewarding effects of alcohol. It modulates the trigeminovascular signaling that is effective in migraine prevention. Topiramate is structurally similar to fructose- 1,6-diphosphate and has the ability to inhibit the enzyme fructose 1,6-bisphosphatase, thereby preventing gluconeogenesis. It is found to inhibit the AMPA/kainate receptor-mediated signaling pathway in cultured neurons.

Packaging

10, 50 mg in glass bottle

Application

Topiramate has been used:
• to study the antiaggressive effects of topiramate in mice.
• to study of the effect of topiramate in promoting neurite outgrowth post nerve injury in fetal rat cortical and hippocampal tissues.
• as a mitochondrial carbonic anhydrase inhibitor to block the effects of high glucose or glucotoxicity.
• to reduce cell death and mitochondrial dysfunction induced by the administration of kainic acid.

Features and Benefits

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

Topiramate has a molar mass of 339, with 40% of this mass being that of oxygen atoms. These oxygen atoms serve as proton acceptors and the amide group functions as a donor for the formation of hydrogen bond. Topiramate is an antiepileptic drug (AED) and is structurally quite distinct from other AEDs as it is derived from D-fructose, a naturally occurring sugar moiety, and has sulfamate functionality. Topiramate crosses the cell membranes and blood-brain barrier readily.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
LS7083000

Documents

Certificate of Analysis

Certificate of Origin


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Protocols & Articles
Peer-Reviewed Papers
15

References

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