LEVETIRACETAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H14N2O2
Molecular Weight	170.209
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](N1CCCC1=O)C(N)=O

InChI

InChIKey=HPHUVLMMVZITSG-LURJTMIESA-N

InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C8H14N2O2
Molecular Weight	170.209
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021035s093,021505s033lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20136375

Levetiracetam is an anticonvulsant medication used to treat epilepsy. Levetiracetam may selectively prevent hypersynchronization of epileptiform burst firing and propagation of seizure activity. The precise mechanism(s) by which levetiracetam exerts its antiepileptic effect is unknown. The antiepileptic activity of levetiracetam was assessed in a number of animal models of epileptic seizures. Levetiracetam did not inhibit single seizures induced by maximal stimulation with electrical current or different chemoconvulsants and showed only minimal activity in submaximal stimulation and in threshold tests. Levetiracetam also displayed inhibitory properties in the kindling model in rats, another model of human complex partial seizures, both during kindling development and in the fully kindled state. The predictive value of these animal models for specific types of human epilepsy is uncertain. In vitro and in vivo recordings of epileptiform activity from the hippocampus have shown that levetiracetam inhibits burst firing without affecting normal neuronal excitability, suggesting that levetiracetam may selectively prevent hypersynchronization of epileptiform burst firing and propagation of seizure activity. Levetiracetam at concentrations of up to 10 µM did not demonstrate binding affinity for a variety of known receptors, such as those associated with benzodiazepines, GABA (gamma-aminobutyric acid), glycine, NMDA (Nmethyl-D-aspartate), re-uptake sites, and second messenger systems. Furthermore, in vitro studies have failed to find an effect of levetiracetam on neuronal voltage-gated sodium or T-type calcium currents and levetiracetam does not appear to directly facilitate GABAergic neurotransmission. However, in vitro studies have demonstrated that levetiracetam opposes the activity of negative modulators of GABA- and glycine-gated currents and partially inhibits N-type calcium currents in neuronal cells. A saturable and stereoselective neuronal binding site in rat brain tissue has been described for levetiracetam. Experimental data indicate that this binding site is the synaptic vesicle protein SV2A, thought to be involved in the regulation of vesicle exocytosis. Interaction of levetiracetam with the SV2A protein may contribute to the antiepileptic mechanism of action of the drug. Levetiracetam, along with other anti-epileptic drugs, can increase the risk of suicide behavior or thoughts. People taking levetiracetam should be monitored closely for signs of worsening depression, suicidal thoughts or tendencies, or any altered emotional or behavioral states.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Synaptic vesicle glycoprotein 2A 2 Target ID: CHEMBL1998 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15367040	Agonist 2678
Voltage-gated N-type calcium channel alpha-1B subunit 12 Target ID: CHEMBL4478 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11879381	Blocker 537

Conditions

Condition	Modality	Highest Phase	Product
Partial onset seizures 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021035s093,021505s033lbl.pdf	Palliative	Approved 8429	KEPPRA Approved Use Levetiracetam tablets USP are antiepileptic drugs indicated for adjunctive therapy in the treatment of: Partial onset seizures in patients 4 years of age and older with epilepsy ( ) 1.1 Myoclonic seizures in patients 12 years of age and older with juvenile myoclonic epilepsy ( ) 1.2 Primary generalized tonic-clonic seizures in patients 6 years of age and older with idiopathic generalized epilepsy ( ) 1.3 1.1 Partial Onset Seizures Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy. Information describing the use of levetiracetam in pediatric patients less than 4 years of age as adjunctive therapy in the treatment of partial onset seizures is approved for UCB, Inc.'s levetiracetam tablets. However, due to UCB, Inc.'s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.2 Myoclonic Seizures in Patients with Juvenile Myoclonic Epilepsy Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of myoclonic seizures in adults and adolescents 12 years of age and older with juvenile myoclonic epilepsy. 1.3 Primary Generalized Tonic-Clonic Seizures Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of primary generalized tonic-clonic seizures in adults and children 6 years of age and older with idiopathic generalized epilepsy. Launch Date 1999
Juvenile myoclonic epilepsy 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021035s093,021505s033lbl.pdf	Palliative	Approved 8429	KEPPRA Approved Use Levetiracetam tablets USP are antiepileptic drugs indicated for adjunctive therapy in the treatment of: Partial onset seizures in patients 4 years of age and older with epilepsy ( ) 1.1 Myoclonic seizures in patients 12 years of age and older with juvenile myoclonic epilepsy ( ) 1.2 Primary generalized tonic-clonic seizures in patients 6 years of age and older with idiopathic generalized epilepsy ( ) 1.3 1.1 Partial Onset Seizures Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy. Information describing the use of levetiracetam in pediatric patients less than 4 years of age as adjunctive therapy in the treatment of partial onset seizures is approved for UCB, Inc.'s levetiracetam tablets. However, due to UCB, Inc.'s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.2 Myoclonic Seizures in Patients with Juvenile Myoclonic Epilepsy Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of myoclonic seizures in adults and adolescents 12 years of age and older with juvenile myoclonic epilepsy. 1.3 Primary Generalized Tonic-Clonic Seizures Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of primary generalized tonic-clonic seizures in adults and children 6 years of age and older with idiopathic generalized epilepsy. Launch Date 1999
Idiopathic generalized epilepsy 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021035s093,021505s033lbl.pdf	Palliative	Approved 8429	KEPPRA Approved Use Levetiracetam tablets USP are antiepileptic drugs indicated for adjunctive therapy in the treatment of: Partial onset seizures in patients 4 years of age and older with epilepsy ( ) 1.1 Myoclonic seizures in patients 12 years of age and older with juvenile myoclonic epilepsy ( ) 1.2 Primary generalized tonic-clonic seizures in patients 6 years of age and older with idiopathic generalized epilepsy ( ) 1.3 1.1 Partial Onset Seizures Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy. Information describing the use of levetiracetam in pediatric patients less than 4 years of age as adjunctive therapy in the treatment of partial onset seizures is approved for UCB, Inc.'s levetiracetam tablets. However, due to UCB, Inc.'s marketing exclusivity rights, this drug product is not labeled with that pediatric information. 1.2 Myoclonic Seizures in Patients with Juvenile Myoclonic Epilepsy Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of myoclonic seizures in adults and adolescents 12 years of age and older with juvenile myoclonic epilepsy. 1.3 Primary Generalized Tonic-Clonic Seizures Levetiracetam tablets USP are indicated as adjunctive therapy in the treatment of primary generalized tonic-clonic seizures in adults and children 6 years of age and older with idiopathic generalized epilepsy. Launch Date 1999

C_max

Value	Dose	Analyte	Population
2.45 μg/mL REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	LEVETIRACETAM unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.38 μg/mL REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	LEVETIRACETAM unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
25.8 μg/mL REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVETIRACETAM unknown	Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
19.635 ug/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849485	750 mg single, oral dose: 750 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fed
21.625 ug/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849862	750 mg single, oral dose: 750 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fasted
26.32 ug/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00859430	1000 mg single, oral dose: 1000 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fed
30.281 ug/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00859521	1000 mg single, oral dose: 1000 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fasted

AUC

Value	Dose	Analyte	Population
17.7 μg × h/mL REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	LEVETIRACETAM unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
16 μg × h/mL REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	LEVETIRACETAM unknown	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
241 μg × h/mL REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVETIRACETAM unknown	Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
173.932 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849862	750 mg single, oral dose: 750 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fasted
176.267 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849485	750 mg single, oral dose: 750 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fed
249.26 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00859430	1000 mg single, oral dose: 1000 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fed
269.172 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00859521	1000 mg single, oral dose: 1000 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fasted
186.097 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849862	750 mg single, oral dose: 750 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fasted
186.758 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00849485	750 mg single, oral dose: 750 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fed
261.018 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00859430	1000 mg single, oral dose: 1000 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fed
281.155 ug*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00859521	1000 mg single, oral dose: 1000 mg route of administration: oral experiment type: single co-administered:	LEVETIRACETAM plasma	Homo sapiens population: age: sex: food status: Fasted

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% REVIEW https://doi.org/10.1111/j.1528-1167.2001.00005.x	1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		LEVETIRACETAM unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6437	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6437
MolPort	MolPort-003-848-377	https://www.molport.com/shop/molecule-link/MolPort-003-848-377
Selleck Chemicals	Levetiracetam	http://www.selleckchem.com/products/Levetiracetam.html
ZINC	ZINC000001547851	http://zinc15.docking.org/substances/ZINC000001547851
eMolecules	902043	https://www.emolecules.com/cgi-bin/more?vid=902043

PubMed

Title	Date	PubMed
		252159868
The novel antiepileptic drug levetiracetam (ucb L059) appears to act via a specific binding site in CNS membranes.	1995 Nov 14	8605950
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Influence of levetiracetam on the anticonvulsant efficacy of conventional antiepileptic drugs against audiogenic seizures in DBA/2 mice.	2007 Jul	17553669
Levetiracetam inhibits interleukin-1 beta inflammatory responses in the hippocampus and piriform cortex of epileptic rats.	2010 Mar 3	20080147

Patents

Sample Use Guides

In Vivo Use Guide

Partial Onset Seizures: Adults 16 Years and Older. Initiate treatment with a daily dose of 1000 mg/day, given as twice-daily dosing (500 mg twice daily) Myoclonic Seizures in Patients 12 Years of Age and Older with Juvenile Myocloni Epilepsy: Initiate treatment with a dose of 1000 mg/day, given as twice-daily dosing (500 mg twice daily). Increase the dosage by 1000 mg/day every 2 weeks to the recommended daily dose of 3000 mg. Primary Generalized Tonic-Clonic Seizures: Adults 16 Years and Older Initiate treatment with a dose of 1000 mg/day, given as twice-daily dosing(500 mg twice daily). Increase dosage by 1000 mg/day every 2 weeks to the recommended daily dose of 3000 mg.

Route of Administration: Oral

In Vitro Use Guide

Apoptosis and cytotoxic function of CD8+ T lymphocytes were measured using flow cytometry following in vitro exposure to Levetiracetam (LEV) (5 mg/L and 50 mg/L). High concentration of LEV decreased perforin release of CD8+ T lymphocytes. LEV had no influence on apoptosis and proliferation (p>0.05)

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:36:39 GMT 2023` Edited by `admin` on `Fri Dec 15 15:36:39 GMT 2023`
Record UNII	44YRR34555
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVETIRACETAM

Official Name

English

LEVETIRACETAM HOSPIRA

Brand Name

English

ELEPSIA

Brand Name

English

LEVETIRACETAM [USP-RS]

Common Name

English

LEVETIRACETAM [ORANGE BOOK]

Common Name

English

Levetiracetam [WHO-DD]

Common Name

English

LEVETIRACETAM [MI]

Common Name

English

LEVETIRACETAM RATIOPHARM

Brand Name

English

LEVETIRACETAM [USP MONOGRAPH]

Common Name

English

LEVETIRACETAM [EP MONOGRAPH]

Common Name

English

NSC-760119

Code

English

MATEVER

Brand Name

English

LEVETIRACETAME

Common Name

English

LEVETIRACETAM [HSDB]

Common Name

English

LEVETIRACETAM SUN

Brand Name

English

LEVETIRACETAM [JAN]

Common Name

English

AGB-101

Code

English

LEVETIRACETAM [USAN]

Common Name

English

LEVETIRACETAM [VANDF]

Common Name

English

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

Systematic Name

English

UCB 22059

Code

English

N03AX14

Code

English

LEVETIRACETAM [USP IMPURITY]

Common Name

English

1-PYRROLIDINEACETAMIDE, .ALPHA.-ETHYL-2-OXO-, (.ALPHA.S)-

Common Name

English

LEVETIRACETAM TEVA

Brand Name

English

LEVETIRACETAM ACTAVIS GROUP

Brand Name

English

LEVETIRACETAM [EP IMPURITY]

Common Name

English

LEVETIRACETAM ACTAVIS

Brand Name

English

LEVETIRACETAM [EMA EPAR]

Common Name

English

levetiracetam [INN]

Common Name

English

LEVETIRACETAM [MART.]

Common Name

English

UCB-L059

Code

English

UCB-22059

Code

English

LEVETIRACETAM ACCORD

Brand Name

English

Classification Tree Code System Code

NDF-RT

N0000175753