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T0575

Topiramate

Name: Topiramate
Brand: SIGMA

≥98% (HPLC), Kainate GluR5 receptor antagonist, solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₂₁NO₈S

CAS Number:

97240-79-4

Molecular Weight:

339.36

UNSPSC Code:

12352200

PubChem Substance ID:

24724627

NACRES:

NA.77

MDL number:

MFCD00865320

Assay:

≥98% (HPLC)

Form:

solid

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Properties

Product Name

Topiramate, ≥98% (HPLC), solid

Quality Segment

200

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: 40 mg/mL

originator

Johnson & Johnson

storage temp.

2-8°C

SMILES string

NS(OC[C@]12[C@](OC(C)(C)O2)([H])[C@@]3([H])[C@@](OC(C)(C)O3)([H])CO1)(=O)=O

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

Gene Information

Description

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.

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.

Biochem/physiol Actions

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.

Kainate GluR5 receptor antagonist; anticonvulsant.

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.

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Signal Word

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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