Brivaracetam

Title: Brivaracetam
CAS Registry Number: 357336-20-0
CAS Name: (aS,4R)-a-Ethyl-2-oxo-4-propyl-1-pyrrolidineacetamide
Additional Names: (2S)-2-[(4R)-2-oxo-4-propylpyrrolidinyl]butanamide
Manufacturers' Codes: UCB-34714
Molecular Formula: C11H20N2O2
Molecular Weight: 212.29
Percent Composition: C 62.23%, H 9.50%, N 13.20%, O 15.07%
Literature References: Orally active synaptic vesicle protein 2 (SV2A) ligand; analog of levetiracetam, q.v. Prepn: E. Differding et al., WO 0162726; eidem, US 6911461 (2001, 2005 both to UCB); B. M. Kenda et al., J. Med. Chem. 47, 530 (2004). Review of pharmacology and clinical experience: B. Malawska, K. Kulig, Curr. Opin. Invest. Drugs 6, 740-746 (2005).
Properties: Colorless, monoclinic crystals from isopropyl ether, mp 76.38°. [a]D25 -60.57° (c = 1 in methanol). Crystal density: 1.093. Log P (octanol/water, pH 7.4 PBS): 1.00. Soly in water: 681 mg/ml.
Melting point: mp 76.38°
Optical Rotation: [a]D25 -60.57° (c = 1 in methanol)
Log P: Log P (octanol/water, pH 7.4 PBS): 1.00
Therap-Cat: Anticonvulsant; in treatment of progressive myoclonic epilepsies.
Keywords: Anticonvulsant.
Brivudine Brodimoprim Bromacil Bromadiolone Bromal

Brivaracetam
Brivaracetam.svg Brivaracetam3d.png
Identifiers
PubChem 9837243
ChemSpider 8012964 YesY
ChEMBL CHEMBL607400
Jmol-3D images Image 1
Properties
Molecular formula C11H20N2O2
Molar mass 212.29 g mol−1
Pharmacology
Routes of
administration
Oral
Legal status


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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Brivaracetam, the 4-n-propyl analog of levetiracetam, is a racetam derivative with anticonvulsant properties.[1][2] Brivaracetam is believed to act by binding to the ubiquitous synaptic vesicle protein SV2.[3] Phase II clinical trials in adult patients with refractory partial seizures were promising. Positive preliminary results from stage III trials have been recorded,[4][5] along with evidence that it is around 10 times more potent[6] for the prevention of certain types of seizure in mouse models than levetiracetam, of which it is an analogue.