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Merck
CN

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

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Product Name

Topiramate, ≥98% (HPLC), solid

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 key

KJADKKWYZYXHBB-XBWDGYHZSA-N

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

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: 40 mg/mL

originator

Johnson & Johnson

storage temp.

2-8°C

Quality Level

200

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)

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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.

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.

signalword

Warning

pictograms

Exclamation mark
GHS07

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
0000348944
0000336298
0000333435
0000333436
0000348944

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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
Ping Patrick et al.
Journal of endocrinology and diabetes, 2(2) (2015-07-15)
Hyperglycemia in diabetes mellitus causes oxidative stress and pericyte depletion from the microvasculature of the brain thus leading to the Blood-Brain Barrier (BBB) disruption. The compromised BBB exposes the brain to circulating substances, resulting in neurotoxicity and neuronal cell death.
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
V L Smith-Swintosky et al.
Neuroreport, 12(5), 1031-1034 (2001-04-17)
Topiramate is a structurally novel neurotherapeutic agent with a unique combination of pharmacological properties and currently is available in most world markets for treating several seizure disorders. Because its pharmacological profile was suggestive of possible activity as a neuroprotectant, topiramate
R P Shank et al.
Epilepsia, 41 Suppl 1, S3-S9 (2000-04-18)
In this overview, we discuss the discovery and development of topiramate (TPM) as an anticonvulsant, including notable aspects of its chemical, biologic, and pharmacokinetic properties. In particular, we highlight its anticonvulsant profile in traditional seizure tests and animal models of
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