Topiramate

CAT: 0804-HY-B0122-01Size: 100 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-B0122-01Size:100 mg

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Description

Topiramate (McN 4853) is a broad-spectrum antiepileptic agent. Topiramate is a GluR5 receptor antagonist. Topiramate produces its antiepileptic effects through enhancement of GABAergic activity, inhibition of kainate/AMPA receptors, inhibition of voltage-sensitive sodium and calcium channels, increases in potassium conductance, and inhibition of carbonic anhydrase[1][2][3].

CAS Number

97240-79-4

Product Name Alternative

McN 4853; RWJ 17021

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Calcium Channel; Carbonic Anhydrase; GABA Receptor; iGluR; Potassium Channel; Sodium Channel

Type

Reference compound

Related Pathways

Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling

Applications

Neuroscience-Neuromodulation

Field of Research

Neurological Disease

Assay Protocol

https://www.medchemexpress.com/Topiramate.html

Purity

99.76

Solubility

DMSO : ≥ 100 mg/mL|H2O : 4 mg/mL (ultrasonic)

Smiles

NS(OC[C@]1(OC(C)(C)O2)[C@@H]2[C@H](OC(C)(C)O3)[C@H]3CO1)(=O)=O

Molecular Formula

C12H21NO8S

Molecular Weight

339.36

Precautions

H302, H315, H319, H335

References & Citations

[1]Lyseng-Williamson KA, et al. Topiramate: a review of its use in the treatment of epilepsy. Drugs. 2007;67 (15) :2231-56.|[2]Nakamura J, et al. Target pharmacology of topiramate, a new antiepileptic drug. Nihon Yakurigaku Zasshi. 2000 Jan;115 (1) :53-7.|[3]Kaminski RM, et al. Topiramate selectively protects against seizures induced by ATPA, a GluR5 kainate receptor agonist. Neuropharmacology. 2004 Jun;46 (8) :1097-104.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

Launched

Isoform

AMPA Receptor; Kainate Receptor

Chemical Information

Topiramate

Topiramate can cause developmental toxicity according to state or federal government labeling requirements.

CAS Number	97240-79-4
PubChem CID	5284627
IUPAC Name	[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate
Molecular Formula	C12H21NO8S
Molecular Weight	339.36
XLogP	-0.8
Topological Polar Surface Area	124
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Heavy Atom Count	22
Formal Charge	0
Complexity	556

SMILES

CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C

InChI

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

InChIKey

KJADKKWYZYXHBB-XBWDGYHZSA-N

Chemical Structure

2D Structure

CAS: 97240-79-4

CID: 5284627

Formula: C12H21NO8S

MW: 339.36

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	339.36
XLogP3	-0.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	339.09878780
Monoisotopic Mass	339.09878780
Topological Polar Surface Area	124 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	556
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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T0675-01	Topiramate

Topiramate

Chemical Information

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