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Levetiracetam

Levetiracetam is clinically used to treat a wide variety of seizure disorders, including partial, myoclonic, and tonic-clonic seizures as well as mood and psychiatric disorders such as anxiety, autism, and Tourette’s syndrome. Levetiracetam displays anticonvulsant/antiepileptic, neuromodulatory, anxiolytic, and cognition enhancing activities. Levetiracetam binds to synaptic vesicle glycoprotein SV2A, a membrane glycoprotein common to all synaptic and endocrine vesicles. SV2A plays a role in Ca2+-induced vesicle fusion, action potential proliferation, normal CNS function, and survival. Altering SV2A function inhibits presynaptic Ca2+ release, reduces excitatory postsynaptic potentials, and inhibits synaptic transmission. This compound is also under examination as a potential treatment for Alzheimer’s disease, as it reduces memory and learning deficits, synaptic dysfunction, and hippocampal remodeling in a transgenic murine model of the disease.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18939687

Cas No.

102767-28-2

Purity

≥98%

Formula

C8H14N2O2

Formula Wt.

170.21

Chemical Name

2(S)-(2-oxopyrrolidin-1-yl)butyramide

IUPAC Name

(2S)-2-(2-oxopyrrolidin-1-yl)butanamide

Melting Point

117°C

Solubility

Soluble in DMSO, water, and ethanol, all to 34mg/mL

Appearance

White to off white powder

Vogl C, Mochida S, Wolff C, et al. The synaptic vesicle glycoprotein 2A ligand levetiracetam inhibits presynaptic Ca2+ channels through an intracellular pathway. Mol Pharmacol. 2012 Aug;82(2):199-208. PMID: 22554805.

Sanchez PE, Zhu L, Verret L, et al. Levetiracetam suppresses neuronal network dysfunction and reverses synaptic and cognitive deficits in an Alzheimers disease model. Proc Natl Acad Sci U S A. 2012 Oct 16;109(42):E2895-903. PMID: 22869752.

Farooq MU, Bhatt A, Majid A, et al. Levetiracetam for managing neurologic and psychiatric disorders. Am J Health Syst Pharm. 2009 Mar 15;66(6):541-61. PMID: 19265183.

Lynch BA, Lambeng N, Nocka K, et al. The synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam. Proc Natl Acad Sci U S A. 2004 Jun 29;101(26):9861-6. PMID: 15210974.

CHIR-99022