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T0575

Topiramate

≥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
Quality level:
200
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Product Name

Topiramate, ≥98% (HPLC), solid

Quality Level

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

human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768), GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), GABRD(2563), GABRE(2564), GABRG1(2565), GABRG2(2566), GABRG3(2567), GABRP(2568), GABRQ(55879), GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIK5(2901), SCN10A(6336), SCN11A(11280), SCN1A(6323), SCN2A(6326), SCN3A(6328), SCN4A(6329), SCN5A(6331), SCN7A(6332), SCN8A(6334), SCN9A(6335)
mouse ... Car5a(12352)
rat ... Car2(54231), Car4(29242)

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

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.

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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pictograms

Exclamation mark
GHS07

signalword

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

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCB0373
SLBZ5431
SLBR9037V
SLBS0283V
SLBN2021V

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Bankole A Johnson et al.
Lancet (London, England), 361(9370), 1677-1685 (2003-05-28)
Topiramate, a sulphamate fructopyranose derivative, might antagonise alcohol's rewarding effects associated with abuse liability by inhibiting mesocorticolimbic dopamine release via the contemporaneous facilitation of gamma-amino-butyric acid activity and inhibition of glutamate function. We aimed to see whether topiramate was more
Jose Francisco Navarro et al.
Methods and findings in experimental and clinical pharmacology, 29(3), 195-198 (2007-05-24)
Topiramate, an antiepileptic drug, has been found to be useful for the treatment of aggression in clinical populations. However, no studies have explored the action of this compound on aggressive behavior in laboratory animals. This work examined the effects of
Jan Lewis Brandes et al.
JAMA, 291(8), 965-973 (2004-02-26)
Small open-label and controlled trials suggest that the antiepileptic drug topiramate is effective for migraine prevention. To assess the efficacy and safety of topiramate for migraine prevention in a large controlled trial. A 26-week, randomized, double-blind, placebo-controlled study was conducted
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Global Trade Item Number

SKUGTIN
T0575-50MG04061837335396
T0575-10MG04061837335365