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T0575

Sigma-Aldrich

Topiramate

≥98% (HPLC), solid

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Synonym(s):
2,3:4,5-Bis-O-(1-methylethylidene)-36-D-fructo-pyranose sulfamate, McN 4853, RWJ 17021, Topamax
Empirical Formula (Hill Notation):
C12H21NO8S
CAS Number:
Molecular Weight:
339.36
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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1 of 4

This Item
PHR1600Y0002134T-039
Topiramate ≥98% (HPLC), solid

Sigma-Aldrich

T0575

Topiramate

Topiramate Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1600

Topiramate

Topiramate European Pharmacopoeia (EP) Reference Standard

Y0002134

Topiramate

Topiramate solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

T-039

Topiramate solution

form

solid

form

-

form

-

form

liquid

color

white

color

-

color

-

color

-

solubility

DMSO: 40 mg/mL

solubility

-

solubility

-

solubility

-

originator

Johnson & Johnson

originator

-

originator

-

originator

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Topiramate Related Compound A United States Pharmacopeia (USP) Reference Standard

USP

1672210

Topiramate Related Compound A

Rufinamide ≥98% (HPLC), powder

Sigma-Aldrich

R8404

Rufinamide

Lamotrigine ≥98%, powder

Sigma-Aldrich

L3791

Lamotrigine

Oxcarbazepine ≥98% (HPLC), solid

Sigma-Aldrich

O3764

Oxcarbazepine

Topiramate-D12 solution 100 μg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

T-041

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Zonisamide sodium salt ≥98% (HPLC), powder

Sigma-Aldrich

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Zonisamide sodium salt

(±)-Vigabatrin

Sigma-Aldrich

V8261

(±)-Vigabatrin

(S)-CPP sodium salt ≥96% (HPLC)

Sigma-Aldrich

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(S)-CPP sodium salt

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
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.
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
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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