1377. Brivaracetam

Nomenclature

CAS number: 357336-20-0
(αS,4R)-α-Ethyl-2-oxo-4-propyl-1-pyrrolidineacetamide; (2S)-2-[(4R)-2-oxo-4-propylpyrrolidinyl]butanamide; UCB-34714.
C11H20N2O2; mol wt 212.29.
C 62.23%, H 9.50%, N 13.20%, O 15.07%.

Description and 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. Investig. Drugs 6, 740-746 (2005).

Chemical structure

Properties

Colorless, monoclinic crystals from isopropyl ether, mp 76.38°. [α]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.

Therapeutic Category

Anticonvulsant; in treatment of progressive myoclonic epilepsies.

Keywords

Anticonvulsant