ETIRACETAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C8H14N2O2
Molecular Weight	170.209
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(N1CCCC1=O)C(N)=O

InChI

InChIKey=HPHUVLMMVZITSG-UHFFFAOYSA-N

InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)

HIDE SMILES / InChI

Molecular Formula	C8H14N2O2
Molecular Weight	170.209
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.rxlist.com/keppra-drug.htm | https://www.ncbi.nlm.nih.gov/pubmed/6771807 | https://www.ncbi.nlm.nih.gov/pubmed/3786350 | https://www.ncbi.nlm.nih.gov/pubmed/7312895

Etiracetam is a nootropic agent. (-)-(S) enantiomer of etiracetam levetiracetam (Keppra®) is used for the treatment of epilepsy.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
Desynchronizing effect of levetiracetam on epileptiform responses in rat hippocampal slices.	2003-07-01	12824774
Expression of brain-derived neurotrophic factor (BDNF) and inducible nitric oxide synthase (iNOS) in rat astrocyte cultures treated with Levetiracetam.	2003-06-27	12763257
Levetiracetam monotherapy for liver transplant patients with seizures.	2003-06	12826199
[Levetiracetam in the treatment of epilepsy].	2003-05-29	12822020
Anxiolytic profile of the antiepileptic drug levetiracetam in the Vogel conflict test in the rat.	2003-05-23	12782190
Efficacy of levetiracetam in a patient with Unverricht-Lundborg progressive myoclonic epilepsy.	2003-04-22	12707458
Levetiracetam has no significant gamma-aminobutyric acid-related effect on paired-pulse interaction in the dentate gyrus of rats.	2003-04-18	12694808
A systematic review of the behavioral effects of levetiracetam in adults with epilepsy, cognitive disorders, or an anxiety disorder during clinical trials.	2003-04	12697136
Maintenance of improvement in health-related quality of life during long-term treatment with levetiracetam.	2003-04	12697135
Dramatic effect of levetiracetam on epileptic negative myoclonus.	2003-04	12675706
Levetiracetam for benign epilepsy of childhood with centrotemporal spikes-three cases.	2003-04	12651081
Levetiracetam monotherapy for newly diagnosed epilepsy patients.	2003-04	12651080
Levetiracetam monotherapy for primary generalised epilepsy.	2003-04	12651079
An open-label study of levetiracetam at individualised doses between 1000 and 3000 mg day(-1) in adult patients with refractory epilepsy.	2003-04	12651078
Clinical experience of marketed Levetiracetam in an epilepsy clinic-a one year follow up study.	2003-04	12651077
Efficacy and tolerability of levetiracetam during 1-year follow-up in patients with refractory epilepsy.	2003-04	12651076
Levetiracetam reduces caffeine-induced Ca2+ transients and epileptiform potentials in hippocampal neurons.	2003-03-03	12634506
The pharmacokinetic characteristics of levetiracetam.	2003-03	12731458
Microemulsion electrokinetic chromatography applied for separation of levetiracetam from other antiepileptic drugs in polypharmacy.	2003-03	12658687
Electrophysiological, neurochemical and regional effects of levetiracetam in the rat pilocarpine model of temporal lobe epilepsy.	2003-03	12566232
Clinically relevant reduction of lamotrigine concentrations by carbamazepine.	2003-02	12648898
Effects of lamotrigine and levetiracetam on seizure development in a rat amygdala kindling model.	2003-02	12576171
Evidence for sustained efficacy of levetiracetam as add-on epilepsy therapy.	2003-02	12576168
Effects of antiepileptic comedication on levetiracetam pharmacokinetics: a pooled analysis of data from randomized adjunctive therapy trials.	2003-02	12576167
Levetiracetam efficacy in refractory partial-onset seizures, especially after failed epilepsy surgery.	2003-02	12558576
Levetiracetam, a new antiepileptic agent: lack of in vitro and in vivo pharmacokinetic interaction with valproic acid.	2003-02	12558570
Correlation of levetiracetam concentrations between serum and saliva.	2003-02	12548146
Neuroprotective effects of anticonvulsants in rat hippocampal slice cultures exposed to oxygen/glucose deprivation.	2003-01-02	12531459
Successful treatment of pharmacoresistent continuous spike wave activity during slow sleep with levetiracetam.	2003-01	12607537
A paradoxical effect of levetiracetam may be seen in both children and adults with refractory epilepsy.	2003-01	12495648
Effect of levetiracetam in refractory childhood epilepsy syndromes.	2003	12788038
Levetiracetam control of myoclonus in a patient with Creutzfeldt-Jakob disease.	2003	12646771
Antiepileptic drug therapy for adults: when to initiate and how to choose.	2002-12	12479527
Effect of levetiracetam on rapid motor learning in humans.	2002-12	12470179
Levetiracetam may be more effective for late-onset partial epilepsy.	2002-12	12470178
Effect of levetiracetam on epileptiform discharges in human neocortical slices.	2002-12	12460248
New antiepileptic drug therapies.	2002-11	12616686
Improvement of a patient with stuttering on levetiracetam.	2002-10-22	12391373
Amelioration of spinal myoclonus with levetiracetam.	2002-10	12235322
[Effectiveness and tolerability of the new antiepileptic drugs: the position of levetiracetam].	2002-09-18	12235583
[Characteristics and indications of levetiracetam].	2002-09	12373663
The effects of levetiracetam on objective and subjective sleep parameters in healthy volunteers and patients with partial epilepsy.	2002-09	12220322
Levetiracetam in autistic children: an open-label study.	2002-08	12177568
Aggravation of partial seizures by antiepileptic drugs: is there evidence from clinical trials?	2002-07-09	12105311
[Levetiracetam: an anti-epileptic drug with interesting pharmacokinetic properties].	2002-06-29	12132136
Levetiracetam in refractory pediatric epilepsy.	2002-06	12174960
[Levetiracetam: a molecule with a novel mechanism of action in the pharmaceutical treatment of epilepsy].	2002-05-20	12122879
Levetiracetam in the treatment of paroxysmal kinesiogenic choreoathetosis.	2002-05	12112221
The 'number needed to treat' with levetiracetam (LEV): comparison with the other new antiepileptic drugs (AEDs).	2002-04	12185762
A case of levetiracetam (Keppra) poisoning with clinical and toxicokinetic data.	2002	12507057

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:06:32 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:32 GMT 2025`
Record UNII	230447L0GL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVETIRACETAM RACEMIC MIXTURE

Preferred Name

English

ETIRACETAM

Official Name

English

(±)-.ALPHA.-ETHYL-2-OXO-1-PYRROLIDINEACETAMIDE

Systematic Name

English

LEVETIRACETAM RACEMIC MIXTURE [USP-RS]

Common Name

English

1-PYRROLIDINEACETAMIDE, .ALPHA.-ETHYL-2-OXO-

Systematic Name

English

UCB-6474

Code

English

etiracetam [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264