Identification

Name
Levetiracetam
Accession Number
DB01202
Description

Levetiracetam is a drug within the pyrrolidine class that is used to treat various types of seizures stemming from epileptic disorders. It was first approved for use in the United States in 1999 and is structurally and mechanistically unrelated to other anti-epileptic drugs (AEDs).11,13,15 Levetiracetam possesses a wide therapeutic index15,9 and little-to-no potential to produce, or be subject to, pharmacokinetic interactions11,13,15 - these characteristics make it a desirable choice over other AEDs, a class of drugs notorious for having generally narrow therapeutic indexes and a propensity for involvement in drug interactions.10

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 170.212
Monoisotopic: 170.105527699
Chemical Formula
C8H14N2O2
Synonyms
  • Levetiracetam
  • Levetiracetame
  • Levetiracetamum
External IDs
  • UCB 22059
  • UCB L059
  • UCB-22059
  • UCB-L059

Pharmacology

Indication

Levetiracetam is indicated as an adjunctive therapy in the treatment of partial onset seizures in epileptic patients who are one month of age and older. Additionally, it is indicated as an adjunct in the treatment of myoclonic seizures in patients with juvenile myoclonic epilepsy who are 12 years of age and older, and in primary generalized tonic-clonic seizures in patients with idiopathic generalized epilepsy who are 6 years of age and older.11

Levetiracetam is also available as an orally dissolvable tablet that is indicated as an adjunct in the treatment of partial onset seizures in patients with epilepsy who are 4 years of age and older and weigh more than 20kg.12

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Levetiracetam appears to prevent seizure activity via the selective inhibition of hypersynchronized epileptiform burst firing without affecting normal neuronal transmission, though the exact mechanism through which this occurs is unclear.11,15 The therapeutic index of levetiracetam is wide,15,9 making it relatively unique amongst other anti-epileptic medications.

Anti-epileptic drugs, including levetiracetam, may increase the risk of suicidal ideation or behaviour - patients taking levetiracetam should be monitored for the emergence or worsening of depressive symptoms, suicidal ideation, and behavioural abnormalities.11,13,15

Mechanism of action

The exact mechanism through which levetiracetam exerts its anti-epileptic effects is unclear, but is thought to be unique amongst other anti-epileptic medications. Current knowledge suggests that levetiracetam’s binding to synaptic vesicle protein 2A (SV2A) is a key driver of its action. SV2A is a membrane-bound protein that is found on synaptic vesicles and is ubiquitous throughout the CNS4 - it appears to play a role in vesicle exocytosis11,15 and in the modulation of synaptic transmission by increasing the available amount of secretory vesicles available for neurotransmission.7 Stimulation of pre-synaptic SV2A by levetiracetam may inhibit neurotransmitter release,6 but this action does not appear to affect normal neurotransmission. This has led to the suggestion that levetiracetam exclusively modulates the function of SV2A only under pathophysiological conditions.4 Levetiracetam and related analogues showed a correlation between affinity for SV2A and anti-epileptic potency, further suggesting that action at this site contributes to the anti-epileptic activity of the drug.11,15

Levetiracetam has also been shown to indirectly affect GABAergic neurotransmission (despite having no direct effect on GABAergic or glutamatergic receptors) and modulate ionic currents.7 Similarly, levetiracetam has been shown in vitro to inhibit N-type calcium channels.8 How, or even if, these actions are implicated in its anti-epileptic action have yet to be elucidated.

TargetActionsOrganism
ASynaptic vesicle glycoprotein 2A
agonist
Humans
AVoltage-dependent N-type calcium channel subunit alpha-1B
inhibitor
Humans
Absorption

Levetiracetam is rapidly and nearly completely absorbed following oral administration, with a reported absolute oral bioavailability of essentially 100%.15,11,13 Tmax is approximately 1.3 hours after dosing, and Cmax is 31 μg/mL following a single 1000mg dose and 43 μg/mL following repeated dosing.13,15 Co-administration of levetiracetam with food delays Tmax by approximately 1.5 hours and decreases Cmax by 20%.11,13

Volume of distribution

The volume of distribution of levetiracetam is approximately 0.5 to 0.7 L/kg.13,15

Protein binding

Levetiracetam and its metabolites are largely unbound to plasma proteins (<10%).15,11,13

Metabolism

Levetiracetam is minimally metabolized within the body - the major metabolic pathway appears to be the enzymatic hydrolysis of its acetamide group which produces an inactive carboxylic acid metabolite, L057, which accounts for approximately 24% of the total administered dose.11,13 The specific enzyme(s) responsible for this reaction are unclear, but this pathway is known to be independent of hepatic CYP enzymes and has been proposed to be driven primarily by type B esterases in the blood and other tissues.1 Two minor metabolites involving modifications to the pyrrolidone ring have been identified, one involving hydroxylation of the ring (constituting 1.6% of the total dose) and the other involving opening of the ring structure (constituting 0.9% of the total dose).15,11,13

Hover over products below to view reaction partners

Route of elimination

Approximately 66% of the administered dose of levetiracetam is excreted in the urine as unchanged drug,11,13 while only 0.3% of the total dose is excreted via the feces.15 The primary inactive metabolite of levetiracetam, L057, is also found in the urine as approximately 24% of the administered dose.15

Half-life

The plasma half-life of levetiracetam is 6-8 hours and is not affected by dose or repeat administration. Half-life is increased in the elderly (by about 40%)15 and those with renal impairment.11,13

Clearance

The total plasma clearance of levetiracetam is 0.96 mL/min/kg, with renal clearance comprising 0.6 mL/min/kg.11 The primary inactive metabolite of levetiracetam, L057, has a renal clearance of 4 mL/min/kg. Given the relatively high proportion of drug undergoing renal clearance, overall clearance of levetiracetam is reduced in patients with renal impairment.11,13

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

The oral TDLO of levetiracetam in humans is 10 mg/kg.14 Symptoms of levetiracetam overdose are consistent with its adverse effect profile and may include agitation, aggression, somnolence, decreased level of consciousness, respiratory depression, or coma.11,13 There is no antidote for levetiracetam overdose, therefore management should involve general supportive measures and symptomatic treatment. Hemodialysis results in significant clearance of plasma levetiracetam (approximately 50% within 4 hours) and should be considered in cases of overdose as indicated by the patient's status.11,13

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Levetiracetam.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Levetiracetam.
AclidiniumLevetiracetam may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Levetiracetam.
AlimemazineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with Alimemazine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Levetiracetam.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Levetiracetam.
AlprazolamThe risk or severity of adverse effects can be increased when Levetiracetam is combined with Alprazolam.
AlverineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with Alverine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.

Products

Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act LevetiracetamTabletOralTEVA Canada Limited2005-12-07Not applicableCanada flag
Act LevetiracetamTabletOralTEVA Canada Limited2005-12-07Not applicableCanada flag
Act LevetiracetamTabletOralTEVA Canada Limited2005-12-07Not applicableCanada flag
Elepsia XRTablet, extended release1500 mg/1OralSun Pharma Advanced Research Company Limited2019-05-17Not applicableUS flag
Elepsia XRTablet, extended release1000 mg/1OralSun Pharma Advanced Research Company Limited2019-05-17Not applicableUS flag
KeppraTablet1000 mg/1OralUCB Farchim S.A.2000-04-242010-04-22US flag
KeppraTablet, film coated500 mg/1OralMckesson Rxpak Inc2000-04-24Not applicableUS flag
KeppraTablet, film coated750 mg/1OralPhysicians Total Care, Inc.2005-04-15Not applicableUS flag50474 0596 40 nlmimage10 04160230
KeppraTablet, film coated750 mg/1OralUCB, Inc.2000-04-24Not applicableUS flag
KeppraTabletOralUcb Inc2003-07-23Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Abbott-levetiracetamTabletOralAbbott2014-05-302015-12-31Canada flag
Abbott-levetiracetamTabletOralAbbott2014-05-302015-12-31Canada flag
Abbott-levetiracetamTabletOralAbbott2014-05-302015-12-31Canada flag
Ag-levetiracetamTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-levetiracetamTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-levetiracetamTabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-levetiracetamTabletOralApotex Corporation2006-10-20Not applicableCanada flag
Apo-levetiracetamTabletOralApotex Corporation2006-10-20Not applicableCanada flag
Apo-levetiracetamTabletOralApotex Corporation2006-10-20Not applicableCanada flag
Auro-levetiracetamTabletOralAuro Pharma Inc2012-03-15Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
N03AX14 — Levetiracetam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Pyrrolidine-2-ones / N-alkylpyrrolidines / Fatty amides / Tertiary carboxylic acid amides / Primary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
2-pyrrolidone / Aliphatic heteromonocyclic compound / Alpha-amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Fatty acyl / Fatty amide / Hydrocarbon derivative / Lactam
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
pyrrolidin-2-ones (CHEBI:6437)

Chemical Identifiers

UNII
44YRR34555
CAS number
102767-28-2
InChI Key
HPHUVLMMVZITSG-LURJTMIESA-N
InChI
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
IUPAC Name
(2S)-2-(2-oxopyrrolidin-1-yl)butanamide
SMILES
CC[[email protected]](N1CCCC1=O)C(N)=O

References

Synthesis Reference

Tooru Futagawa, Jean-Pierre Canvat, Emile Cavoy, Michel Deleers, Michel Hamende, Vincent Zimmermann, "Process for the preparation of levetiracetam." U.S. Patent US6107492, issued September, 1996.

US6107492
General References
  1. Patsalos PN: Clinical pharmacokinetics of levetiracetam. Clin Pharmacokinet. 2004;43(11):707-24. doi: 10.2165/00003088-200443110-00002. [PubMed:15301575]
  2. Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46. Epub 2006 Oct 10. [PubMed:17045309]
  3. Luna-Tortos C, Fedrowitz M, Loscher W: Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75. doi: 10.1016/j.neuropharm.2008.08.032. Epub 2008 Sep 11. [PubMed:18824002]
  4. Lynch BA, Lambeng N, Nocka K, Kensel-Hammes P, Bajjalieh SM, Matagne A, Fuks B: The synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam. Proc Natl Acad Sci U S A. 2004 Jun 29;101(26):9861-6. Epub 2004 Jun 21. [PubMed:15210974]
  5. Stahl SM: Psychopharmacology of anticonvulsants: levetiracetam as a synaptic vesicle protein modulator. J Clin Psychiatry. 2004 Sep;65(9):1162-3. [PubMed:15367040]
  6. Johannessen Landmark C: Antiepileptic drugs in non-epilepsy disorders: relations between mechanisms of action and clinical efficacy. CNS Drugs. 2008;22(1):27-47. [PubMed:18072813]
  7. De Smedt T, Raedt R, Vonck K, Boon P: Levetiracetam: the profile of a novel anticonvulsant drug-part I: preclinical data. CNS Drug Rev. 2007 Spring;13(1):43-56. [PubMed:17461889]
  8. Lukyanetz EA, Shkryl VM, Kostyuk PG: Selective blockade of N-type calcium channels by levetiracetam. Epilepsia. 2002 Jan;43(1):9-18. [PubMed:11879381]
  9. Patsalos PN: Pharmacokinetic profile of levetiracetam: toward ideal characteristics. Pharmacol Ther. 2000 Feb;85(2):77-85. doi: 10.1016/s0163-7258(99)00052-2. [PubMed:10722121]
  10. Zaccara G, Perucca E: Interactions between antiepileptic drugs, and between antiepileptic drugs and other drugs. Epileptic Disord. 2014 Dec;16(4):409-31. doi: 10.1684/epd.2014.0714. [PubMed:25515681]
  11. FDA Approved Drugs: Levetiracetam Tablets [Link]
  12. FDA Approved Drugs: Levetiracetam ODT [Link]
  13. DPD Approved Drugs: Levetiracetam [Link]
  14. CaymenChem: Levetiracetam MSDS [Link]
  15. MedSafe NZ: Levetiracetam [Link]
KEGG Drug
D00709
KEGG Compound
C07841
PubChem Compound
5284583
PubChem Substance
46508406
ChemSpider
4447633
BindingDB
50422542
RxNav
114477
ChEBI
6437
ChEMBL
CHEMBL1286
ZINC
ZINC000001547851
Therapeutic Targets Database
DAP000502
PharmGKB
PA450206
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Levetiracetam
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingSupportive CareIntracranial Aneurysms / Seizures1
4Active Not RecruitingTreatmentBrain Cancer / Cancer of Brain / Cancer of the Brain / Neoplasms, Brain / Seizures1
4CompletedNot AvailableEpilepsy, Localization Related1
4CompletedBasic ScienceHealthy Volunteers / Impaired kidney function1
4CompletedPreventionManic State Associated With Corticosteroid Use / Memory Loss Associated With Corticosteroid Use1
4CompletedTreatmentAcute Kidney Injury (AKI) / Impaired kidney function / Pharmacokinetics / Renal Failure1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentBody Dysmorphic Disorders1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentEpilepsies8

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Boca Pharmacal
  • Cardinal Health
  • Caremark LLC
  • Catalent Pharma Solutions
  • Cipla Ltd.
  • Cobalt Pharmaceuticals Inc.
  • Cypress Pharmaceutical Inc.
  • D.M. Graham Laboratories Inc.
  • Dept Health Central Pharmacy
  • DispenseXpress Inc.
  • Doctor Reddys Laboratories Ltd.
  • Fleming and Co.
  • Glenmark Generics Ltd.
  • Greenstone LLC
  • Innoviant Pharmacy Inc.
  • InvaGen Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Oso Biopharmaceuticals Manufacturing LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Association
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Quality Care
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandoz
  • Silarx Pharmaceuticals
  • Solco Healthcare US LLC
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • Tolmar Inc.
  • Torrent Pharmaceuticals
  • UCB Pharma
  • UDL Laboratories
  • Vangard Labs Inc.
  • Vistapharm Inc.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
TabletOral
Tablet, coatedOral250 mg
Tablet, extended releaseOral1000 mg/1
Tablet, extended releaseOral1500 mg/1
Tablet, film coated1000 mg
Tablet, film coated250 mg
Tablet, film coated500 mg
Tablet, film coated750 mg
Injection, solution, concentrateParenteral500 mg/5ml
Tablet, film coatedOral
Injection, solution, concentrateIntravenous100 mg/1mL
Tablet, film coatedOral750 mg/1
InjectionIntravenous500 mg/5ml
Tablet
Tablet, coated1000 mg
Tablet, coated250 mg
Tablet, coated500 mg
Tablet, coated750 mg
Tablet, extended release500 mg
Tablet, extended release750 mg
Injection, solution, concentrate500 mg/5ml
SolutionOral
InjectionIntravenous10 mg/1mL
InjectionIntravenous100 mg/1mL
InjectionIntravenous15 mg/1mL
InjectionIntravenous5 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous100 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous100 mg/1mL
Injection, solutionIntravenous1000 mg/100mL
Injection, solutionIntravenous15 mg/1mL
Injection, solutionIntravenous1500 mg/100mL
Injection, solutionIntravenous5 mg/1mL
Injection, solutionIntravenous500 mg/5mL
Injection, solutionIntravenous500 mg/100mL
Injection, solution, concentrateIntravenous500 mg/5mL
SolutionOral100 mg/1mL
SolutionOral1000 mg/10mL
SolutionOral1500 mg/15mL
SolutionOral500 mg/5mL
TabletOral1000 mg/1
TabletOral250 mg
TabletOral250 mg/1
TabletOral500 mg/1
TabletOral500 mg
TabletOral750 mg/1
Tablet, extended releaseOral500 mg/1
Tablet, extended releaseOral750 mg/1
Tablet, film coatedOral1000 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coated, extended releaseOral1000 mg/1
Tablet, film coated, extended releaseOral500 mg/1
Tablet, film coated, extended releaseOral750 mg/1
Tablet, coatedOral1 g
Tablet, coatedOral1000 mg
SolutionOral100 MG
Tablet, film coatedOral1500 MG
Tablet, film coatedOral1000 mg
Tablet, film coatedOral250 mg
Tablet, film coatedOral500 mg
Tablet, film coatedOral750 mg
Tablet, film coatedOral1 G
SolutionOral100 mg/ml
Tablet, coatedOral750 MG
SolutionOral3 ML
GranuleOral1000 mg
GranuleOral1500 mg
GranuleOral250 MG
GranuleOral500 MG
GranuleOral750 MG
SolutionOral1 ML
Injection, solution, concentrateIntravenous100 mg/ml
InjectionIntravascular10 mg/1mL
InjectionIntravascular15 mg/1mL
InjectionIntravascular5 mg/1mL
PowderNot applicable1 g/1g
SolutionOral10 g
Tablet, effervescent1000 mg
Tablet, effervescent1500 mg
Tablet, effervescent250 mg
Tablet, effervescent500 mg
Tablet, film coated, extended release750 mg
TabletOral1000 mg
Tablet1000 mg
Tablet500 mg
Tablet750 mg
TabletOral750 mg
SolutionIntravenous
Tablet, coatedOral500 mg
Tablet, for suspensionOral1000 mg/1
Tablet, for suspensionOral250 mg/1
Tablet, for suspensionOral500 mg/1
Tablet, for suspensionOral750 mg/1
Prices
Unit descriptionCostUnit
Keppra 500 mg/5 ml vial9.28USD ml
Keppra 1000 mg tablet9.01USD tablet
Levetiracetam 1000 mg tablet7.18USD tablet
Keppra xr 750 mg tablet6.46USD tablet
Keppra xr 500 mg tablet6.43USD tablet
Keppra 500 mg tablet5.09USD tablet
Levetiracetam 750 mg tablet4.86USD tablet
Keppra 750 mg tablet4.74USD tablet
Keppra XR 500 mg 24 Hour tablet4.47USD tablet
Keppra 250 mg tablet3.62USD tablet
Levetiracetam 500 mg tablet3.59USD tablet
Levetiracetam 250 mg tablet2.93USD tablet
Apo-Levetiracetam 750 mg Tablet1.7USD tablet
Co Levetiracetam 750 mg Tablet1.7USD tablet
Pms-Levetiracetam 750 mg Tablet1.7USD tablet
Apo-Levetiracetam 500 mg Tablet1.23USD tablet
Co Levetiracetam 500 mg Tablet1.23USD tablet
Pms-Levetiracetam 500 mg Tablet1.23USD tablet
Apo-Levetiracetam 250 mg Tablet1.01USD tablet
Co Levetiracetam 250 mg Tablet1.01USD tablet
Pms-Levetiracetam 250 mg Tablet1.01USD tablet
Keppra 100 mg/ml Solution0.95USD ml
Levetiracetam 100 mg/ml Solution0.68USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8802142Yes2014-08-122031-12-07US flag
US7858122No2010-12-282028-09-17US flag
US6471992No2002-10-292018-02-20US flag
US9463160No2016-10-112018-02-20US flag
US9669009No2017-06-062034-03-14US flag
US9339489No2016-05-172034-03-14US flag
US8431156No2013-04-302027-10-31US flag
US8535717No2013-09-172026-02-22US flag
US8425938No2013-04-232026-02-22US flag
US8163306No2012-04-242027-09-03US flag
US8470367No2013-06-252026-02-22US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)115-119CCanadian label
water solubility104g/100mLCanadian label
logP-0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility298.0 mg/mLALOGPS
logP-0.64ALOGPS
logP-0.59ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)16.09ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.4 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.08 m3·mol-1ChemAxon
Polarizability17.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.9821
Caco-2 permeable-0.6114
P-glycoprotein substrateSubstrate0.5137
P-glycoprotein inhibitor INon-inhibitor0.5612
P-glycoprotein inhibitor IINon-inhibitor0.8786
Renal organic cation transporterNon-inhibitor0.7024
CYP450 2C9 substrateNon-substrate0.8801
CYP450 2D6 substrateNon-substrate0.8184
CYP450 3A4 substrateNon-substrate0.5191
CYP450 1A2 substrateNon-inhibitor0.9394
CYP450 2C9 inhibitorNon-inhibitor0.7603
CYP450 2D6 inhibitorNon-inhibitor0.9471
CYP450 2C19 inhibitorNon-inhibitor0.8459
CYP450 3A4 inhibitorNon-inhibitor0.9669
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9502
Ames testNon AMES toxic0.8783
CarcinogenicityNon-carcinogens0.9094
BiodegradationNot ready biodegradable0.9305
Rat acute toxicity2.1707 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9206
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Transmembrane transporter activity
Specific Function
Plays a role in the control of regulated secretion in neural and endocrine cells, enhancing selectively low-frequency neurotransmission. Positively regulates vesicle fusion by maintaining the readi...
Gene Name
SV2A
Uniprot ID
Q7L0J3
Uniprot Name
Synaptic vesicle glycoprotein 2A
Molecular Weight
82694.665 Da
References
  1. Lynch BA, Lambeng N, Nocka K, Kensel-Hammes P, Bajjalieh SM, Matagne A, Fuks B: The synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam. Proc Natl Acad Sci U S A. 2004 Jun 29;101(26):9861-6. Epub 2004 Jun 21. [PubMed:15210974]
  2. Stahl SM: Psychopharmacology of anticonvulsants: levetiracetam as a synaptic vesicle protein modulator. J Clin Psychiatry. 2004 Sep;65(9):1162-3. [PubMed:15367040]
  3. Johannessen Landmark C: Antiepileptic drugs in non-epilepsy disorders: relations between mechanisms of action and clinical efficacy. CNS Drugs. 2008;22(1):27-47. [PubMed:18072813]
  4. De Smedt T, Raedt R, Vonck K, Boon P: Levetiracetam: the profile of a novel anticonvulsant drug-part I: preclinical data. CNS Drug Rev. 2007 Spring;13(1):43-56. [PubMed:17461889]
  5. DPD Approved Drugs: Levetiracetam [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1B
Uniprot ID
Q00975
Uniprot Name
Voltage-dependent N-type calcium channel subunit alpha-1B
Molecular Weight
262493.84 Da
References
  1. De Smedt T, Raedt R, Vonck K, Boon P: Levetiracetam: the profile of a novel anticonvulsant drug-part I: preclinical data. CNS Drug Rev. 2007 Spring;13(1):43-56. [PubMed:17461889]
  2. Lukyanetz EA, Shkryl VM, Kostyuk PG: Selective blockade of N-type calcium channels by levetiracetam. Epilepsia. 2002 Jan;43(1):9-18. [PubMed:11879381]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46. Epub 2006 Oct 10. [PubMed:17045309]
  2. Luna-Tortos C, Fedrowitz M, Loscher W: Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75. doi: 10.1016/j.neuropharm.2008.08.032. Epub 2008 Sep 11. [PubMed:18824002]

Drug created on June 13, 2005 07:24 / Updated on October 29, 2020 19:26

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