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DRUG SPOTLIGHT…LEVETIRACETAM

December 1, 2013

New Drug Approvals

LEVETIRACETAM, etiracetam

(-)-(S)-α-ethyl-2-oxo-1-pyrrolidine acetamide

(−)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide

CAS…102767-28-2

(aS)-a-Ethyl-2-oxo-1-pyrrolidineacetamide
Names: 2(S)-(2-oxopyrrolidin-1-yl)butyramide
Manufacturers’ Codes: UCB-L059; SIB-S1
Trademarks: Keppra (UCB)
FDA UNII: 44YRR34555
MF: C8H14N2O2
MW 170.21
Percent Composition: C 56.45%, H 8.29%, N 16.46%, O 18.80%

Crystals from ethyl acetate, mp 117°. [a]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).

Mp: mp 117°C

O’Neil, M.J. (ed.). The Merck Index – An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 978
Optical Rotation: [a]25D -90.0° (c = 1 in acetone)
Specific optical rotation: -90 deg at 25 deg C/D (c = 1 in acetone)
Toxicity data: LD50 in male mice, male rats (mg/kg): 1081, 1038 i.v. (Gobert, 1990)
Therap-Cat: Anticonvulsant.
Very…

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