Pular para o conteúdo
Merck
Todas as fotos(2)

Key Documents

View All Documentation

T0575

Sigma-Aldrich

Topiramate

≥98% (HPLC), solid

Sinônimo(s):

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

Faça loginpara ver os preços organizacionais e de contrato
Todas as fotos(2)

About This Item

Fórmula empírica (Notação de Hill):
C12H21NO8S
Número CAS:
97240-79-4
Peso molecular:
339.36
Número MDL:
MFCD00865320
Código UNSPSC:
12352200
ID de substância PubChem:
24724627
NACRES:
NA.77

Ensaio

≥98% (HPLC)

forma

solid

cor

white

solubilidade

DMSO: 40 mg/mL

originador

Johnson & Johnson

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

KJADKKWYZYXHBB-XBWDGYHZSA-N

Informações sobre genes

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)

Procurando produtos similares? Visita Guia de comparação de produtos

Descrição geral

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.

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

Já possui este produto?

Encontre a documentação dos produtos que você adquiriu recentemente na biblioteca de documentos.

Visite a Biblioteca de Documentos

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
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.
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
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
Exibir todos os documentos relacionados

Nossa equipe de cientistas tem experiência em todas as áreas de pesquisa, incluindo Life Sciences, ciência de materiais, síntese química, cromatografia, química analítica e muitas outras.

Entre em contato com a assistência técnica