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Topiramate (lithium)

CAT: 0804-HY-B0122ASize: 1 EachDry Ice: NoHazardous: No
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Description
Topiramate (McN 4853) lithium is a broad-spectrum antiepileptic agent. Topiramate lithium 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
488127-53-3
Product Name Alternative
McN 4853 (lithium) ; RWJ 17021 (lithium)
UNSPSC
12352005
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-lithium.html
Solubility
10 mM in DMSO
Smiles
NS(OC[C@]1(OC(C)(C)O2)[C@@H]2[C@H](OC(C)(C)O3)[C@H]3CO1)(=O)=O.[Li]
Molecular Formula
C12H21LiNO8S
Molecular Weight
346.30
References & Citations
[1]Kaminski RM, et al. Topiramate selectively protects against seizures induced by ATPA, a GluR5 kainate receptor agonist. Neuropharmacology. 2004 Jun;46 (8) :1097-104.|[2]Lyseng-Williamson KA, et al. Topiramate: a review of its use in the treatment of epilepsy. Drugs. 2007;67 (15) :2231-56.|[3]Nakamura J, et al. Target pharmacology of topiramate, a new antiepileptic drug. Nihon Yakurigaku Zasshi. 2000 Jan;115 (1) :53-7.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
AMPA Receptor; Kainate Receptor

Chemical Information

Topiramate lithium
CAS Number488127-53-3
PubChem CID23701952
IUPAC Namelithium [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methoxysulfonylazanide
Molecular FormulaC12H20LiNO8S
Molecular Weight345.3
Topological Polar Surface Area98.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Heavy Atom Count23
Formal Charge0
Complexity562
SMILES
[Li+].CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)[NH-])C
InChI
InChI=1S/C12H20NO8S.Li/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,(H-,13,14,15);/q-1;+1/t7-,8-,9+,12+;/m1./s1
InChIKey
FRVIGWXXRZKZOL-WGAVTJJLSA-N
Chemical Structure
2D Structure
2D structure of Topiramate lithium
CAS: 488127-53-3
CID: 23701952
Formula: C12H20LiNO8S
MW: 345.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight345.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass345.10696620
Monoisotopic Mass345.10696620
Topological Polar Surface Area98.9 Ų
Heavy Atom Count23
Formal Charge0
Complexity562
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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