5461. Levetiracetam

Nomenclature

CAS number: 102767-28-2
(αS)-α-Ethyl-2-oxo-1-pyrrolidineacetamide; 2(S)-(2-oxopyrrolidin-1-yl)butyramide; UCB-L059; SIB-S1; Keppra (UCB).
C8H14N2O2; mol wt 170.21.
C 56.45%, H 8.29%, N 16.46%, O 18.80%.

Description and references

(S)-Enantiomer of the ethyl analog of piracetam, q.v. Prepn: J. Gobert et al., EP 162036; eidem, US 4943639 (1985, 1990 both to UCB); F. Boschi et al., Tetrahedron: Asymmetry 16, 3739 (2005). HPLC-UV determn in plasma: J. Martens-Lobenhoffer, S. M. Bode-Bger, J. Chromatogr. B 819, 197 (2005). Clinical evaluation in refractory partial seizures: S. D. Shorvon et al., Epilepsia 41, 1179 (2000); E. Ben-Menachem, U. Falter, ibid. 1276. Review of pharmacokinetics: P. N. Patsalos, Pharmacol. Ther. 85, 77-85 (2000); of clinical efficacy: E. Ben-Menachem, Expert Opin. Pharmacother. 4, 2079-2088 (2003); of safety and tolerability: D. E. Briggs, J. A. French, Expert Opin. Drug Saf. 3, 415-424 (2004).

Chemical structure

Properties

Crystals from ethyl acetate, mp 117°. [α]25D 90.0° (c = 1 in acetone). Soly (g/100 ml): water 104.0; chloroform 65.3; methanol 53.6; ethanol 16.5; acetonitrile 5.7. Practically insol in n-hexane. LD50 in male mice, male rats (mg/kg): 1081, 1038 i.v. (Gobert, 1990).

Therapeutic Category

Anticonvulsant.

Therapeutic Category (Veterinary)

Anticonvulsant.

Keywords

Anticonvulsant