Identification

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Name
Levetiracetam
Accession Number
DB01202  (APRD01068)
Type
Small Molecule
Groups
Approved
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

Structure
Thumb
Synonyms
  • Levetiracetam
  • Levetiracetame
  • Levetiracetamum
External IDs
UCB 22059 / UCB L059 / UCB-22059 / UCB-L059
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act LevetiracetamTabletOralActavis Pharma Company2005-12-07Not applicableCanada
Act LevetiracetamTabletOralActavis Pharma Company2005-12-07Not applicableCanada
Act LevetiracetamTabletOralActavis Pharma Company2005-12-07Not applicableCanada
Elepsia XRTablet, extended release1500 mg/1OralSun Pharma Advanced Research Company Limited2015-03-13Not applicableUs
Elepsia XRTablet, extended release1000 mg/1OralSun Pharma Advanced Research Company Limited2015-03-13Not applicableUs
KeppraTablet, film coated750 mg/1OralPhysicians Total Care, Inc.2005-04-15Not applicableUs50474 0596 40 nlmimage10 04160230
KeppraInjection, solution, concentrate100 mg/1mLIntravenousUCB, Inc.2006-08-23Not applicableUs
KeppraTablet1000 mg/1OralUCB Farchim S.A.2000-04-242010-04-22Us
KeppraSolution100 mg/1mLOralUcb Inc2003-10-20Not applicableUs
KeppraInjection, solution, concentrate100 mg/1mLIntravenousCardinal Health2006-07-312012-05-31Us
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 End
Abbott-levetiracetamTabletOralAbbott2014-05-302015-12-31Canada
Abbott-levetiracetamTabletOralAbbott2014-05-302015-12-31Canada
Abbott-levetiracetamTabletOralAbbott2014-05-302015-12-31Canada
Ag-levetiracetamTabletOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-levetiracetamTabletOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-levetiracetamTabletOralAngita Pharma Inc.Not applicableNot applicableCanada
Apo-levetiracetamTabletOralApotex Corporation2006-10-20Not applicableCanada
Apo-levetiracetamTabletOralApotex Corporation2006-10-20Not applicableCanada
Apo-levetiracetamTabletOralApotex Corporation2006-10-20Not applicableCanada
Auro-levetiracetamTabletOralAuro Pharma Inc2012-02-14Not applicableCanada
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
UNII
44YRR34555
CAS number
102767-28-2
Weight
Average: 170.212
Monoisotopic: 170.105527699
Chemical Formula
C8H14N2O2
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[C@H](N1CCCC1=O)C(N)=O

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
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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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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

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

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
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Levetiracetam is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineLevetiracetam may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineLevetiracetam may increase the excretion rate of 6-O-benzylguanine which could result in a lower serum level and potentially a reduction in efficacy.
7-DeazaguanineLevetiracetam may increase the excretion rate of 7-Deazaguanine which could result in a lower serum level and potentially a reduction in efficacy.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Additional Data Available
  • Extended Description
    Extended Description

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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

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Food Interactions
  • Take without regard to meals. Food does not affect bioavailabilty.

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]
External Links
KEGG Drug
D00709
KEGG Compound
C07841
PubChem Compound
5284583
PubChem Substance
46508406
ChemSpider
4447633
BindingDB
50422542
ChEBI
6437
ChEMBL
CHEMBL1286
Therapeutic Targets Database
DAP000502
PharmGKB
PA450206
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Levetiracetam
ATC Codes
N03AX14 — Levetiracetam
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAphasia / Strokes1
1CompletedNot AvailableHealthy Volunteers6
1CompletedBasic ScienceEpilepsies2
1CompletedBasic ScienceHealthy Volunteers1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentBenign Childhood Epilepsy With Centro-Temporal Spikes1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHuman Volunteers2
1CompletedTreatmentSeizures1
1, 2Active Not RecruitingTreatmentNeonatal Convulsions1
1, 2CompletedTreatmentDisorder of Fetus or Newborn / Seizures1
1, 2CompletedTreatmentEpilepsies / Malaria, Cerebral / Seizures1
1, 2CompletedTreatmentNeonatal Convulsions1
1, 2CompletedTreatmentSeizures1
1, 2CompletedTreatmentSeizures / Term Neonates1
1, 2CompletedTreatmentTremor, Essential1
1, 2Not Yet RecruitingTreatmentNeonatal Convulsions1
2CompletedNot AvailableCranial Dystonia / Oromandibular Dystonia1
2CompletedNot AvailableDyskinesia, Medication-Induced1
2CompletedNot AvailableIdiopathic Parkinson's Disease1
2CompletedNot AvailablePostherpetic Neuralgia1
2CompletedBasic ScienceMild Cognitive Impairment (MCI)1
2CompletedPreventionEpilepsies / Post-Traumatic Seizure Disorder1
2CompletedSupportive CareBrain and Central Nervous System Tumors / Seizures1
2CompletedTreatmentAlcohol Dependence1
2CompletedTreatmentAlcohol Dependence / Anxiety Disorders / Generalized Anxiety Disorder (GAD) / Panic Disorders / Social Phobia1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS) / Motor Neurone Disease / Primary Lateral Sclerosis1
2CompletedTreatmentAnxiety Disorders1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentChronic Idiopathic Axonal Polyneuropathy1
2CompletedTreatmentDependence, Cocaine / Opioid Dependence / Opioid Dependency1
2CompletedTreatmentDependence, Cocaine / Opioid Dependency1
2CompletedTreatmentEpilepsies6
2CompletedTreatmentEpilepsies / Malaria, Cerebral / Seizures1
2CompletedTreatmentEpilepsies / Partial onset seizure Epilepsy1
2CompletedTreatmentEpilepsy, Localization Related1
2CompletedTreatmentGrand Mal Status Epilepticus1
2CompletedTreatmentPhotosensitive Epilepsy1
2CompletedTreatmentRestless Legs Syndrome (RLS)1
2CompletedTreatmentSeizure, Absence1
2Enrolling by InvitationTreatmentAlzheimer's Disease (AD) / Epilepsies1
2Not Yet RecruitingTreatmentAlzheimer's Disease (AD)1
2Not Yet RecruitingTreatmentGlioblastoma Multiforme (GBM)1
2RecruitingOtherPsychosis / Schizo Affective Disorder / Schizophrenic Disorders / Schizophreniform1
2RecruitingTreatmentAlzheimer's Disease (AD)1
2RecruitingTreatmentAlzheimer's Disease, Early Onset1
2RecruitingTreatmentGlioma of Brain / Gliomas / Neoplasms, Brain1
2RecruitingTreatmentNeonatal Convulsions1
2RecruitingTreatmentNeuroblastomas1
2TerminatedTreatmentAcute Myelogenous Leukaemia (AML) / Refractory Acute Myelogenous Leukemia1
2TerminatedTreatmentAlcohol Abuse / Alcohol Dependence1
2TerminatedTreatmentCervical Dystonia1
2TerminatedTreatmentSickle Cell Disorders1
2Unknown StatusTreatmentLevodopa Induced Dyskinesia (LID)1
2Unknown StatusTreatmentRefractory seizure disorders1
2WithdrawnTreatmentSeizure, Alcohol Related1
2WithdrawnTreatmentStatus Epilepticus, Non-Convulsive1
2, 3CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
2, 3TerminatedTreatmentObsessive Compulsive Disorder (OCD)1
2, 3WithdrawnTreatmentSeizures1
3Active Not RecruitingTreatmentAdverse Effects / Epilepsy, Localization Related1
3Active Not RecruitingTreatmentBenzodiazepine Refractory Status Epilepticus1
3CompletedNot AvailableEpilepsy, Generalized1
3CompletedNot AvailableEpilepsy, Localization Related2
3CompletedNot AvailableEpilepsy, Tonic-Clonic1
3CompletedNot AvailableGeneralized Convulsive Epilepsy1
3CompletedPreventionAlcohol Dependence / Alcoholic Relapse1
3CompletedTreatmentAlcohol Withdrawal Syndrome(AWS)1
3CompletedTreatmentEpilepsies7
3CompletedTreatmentEpilepsies / Grand mal Generalized tonic-clonic seizure3
3CompletedTreatmentEpilepsies / Partial1
3CompletedTreatmentEpilepsies / Partial onset seizure Epilepsy4
3CompletedTreatmentEpilepsy, Generalized1
3CompletedTreatmentEpilepsy, Localization Related5
3CompletedTreatmentEpilepsy, Tonic-Clonic1
3CompletedTreatmentGeneralized Convulsive Epilepsy1
3CompletedTreatmentPanic Disorders1
3CompletedTreatmentStatus; Epilepticus, Tonic-clonic1
3CompletedTreatmentTardive Dyskinesia1
3CompletedTreatmentPartial onset seizure Epilepsy1
3RecruitingHealth Services ResearchEpilepsies1
3RecruitingTreatmentPartial onset seizure Epilepsy1
3TerminatedPreventionPost-Traumatic Seizure Disorder1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentDrug Resistant / Epilepsies1
3TerminatedTreatmentEpilepsies / Seizures1
3TerminatedTreatmentEpilepsy, Localization Related1
3TerminatedTreatmentEpilepsy, Rolandic1
3Unknown StatusTreatmentEpilepsies1
3Unknown StatusTreatmentSeizures, Epileptic / Strokes1
3WithdrawnTreatmentEpilepsies / Refractory seizure disorders1
4Active Not RecruitingSupportive CareIntracranial Aneurysms / Seizures1
4Active Not RecruitingTreatmentEpilepsy, Idiopathic Generalized1
4CompletedNot AvailableEpilepsies1
4CompletedNot AvailableEpilepsy, Localization Related2
4CompletedBasic ScienceHealthy Volunteers / Impaired Renal Function1
4CompletedPreventionManic State Associated With Corticosteroid Use / Memory Loss Associated With Corticosteroid Use1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentBody Dysmorphic Disorders1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentEpilepsies9
4CompletedTreatmentEpilepsies / Primary Brain Tumors1
4CompletedTreatmentEpilepsy, Localization Related4
4CompletedTreatmentGilles de la Tourette's Syndrome / Tic Disorders1
4CompletedTreatmentGrand mal Generalized tonic-clonic seizure1
4CompletedTreatmentPain NOS / Spinal Cord Injuries (SCI)1
4CompletedTreatmentPainful Polyneuropathy1
4CompletedTreatmentParkinson's Disease (PD)1
4CompletedTreatmentSubarachnoid Hemorrhage / Traumatic Brain Injury (TBI)1
4Not Yet RecruitingTreatmentBenign Childhood Epilepsy With Centrotemporal Spikes1
4Not Yet RecruitingTreatmentEpilepsy, Localization Related1
4RecruitingNot AvailableEpilepsies1
4RecruitingTreatmentAcute Kidney Injury (AKI) / Impaired Renal Function / Pharmacokinetics / Renal Failure1
4RecruitingTreatmentBrain Cancer / Cancer of Brain / Cancer of the Brain / Neoplasms, Brain / Seizures1
4RecruitingTreatmentEpilepsies1
4RecruitingTreatmentGliomas1
4RecruitingTreatmentSeizures / Traumatic Brain Injury (TBI)1
4TerminatedTreatmentIntracranial Aneurysms / Seizures1
4Unknown StatusTreatmentCSWS / Subclinical Sleep-Activated Epileptiform Activity1
4WithdrawnSupportive CareSeizures / Subarachnoid Hemorrhage1
4WithdrawnTreatmentParkinson's Disease (PD)1
Not AvailableCompletedNot AvailableEpilepsies3
Not AvailableCompletedNot AvailableEpilepsies / Seizures1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedBasic ScienceAlzheimer's Disease (AD) / Seizures1
Not AvailableCompletedTreatmentAlcohol Abuse / Substance Abuse1
Not AvailableCompletedTreatmentChildhood Absence Epilepsy / Epilepsies / Seizures1
Not AvailableCompletedTreatmentDepression, Bipolar1
Not AvailableCompletedTreatmentEpilepsies1
Not AvailableCompletedTreatmentFibromyalgia1
Not AvailableCompletedTreatmentMigraine1
Not AvailableCompletedTreatmentPostoperative pain1
Not AvailableCompletedTreatmentPremenstrual Dysphoric Disorder1
Not AvailableCompletedTreatmentSeizures4
Not AvailableRecruitingNot AvailableEpilepsies1
Not AvailableRecruitingNot AvailableEpileptic Encephalopathy1
Not AvailableRecruitingOtherSchizophrenic Disorders2
Not AvailableRecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Leukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndrome1
Not AvailableRecruitingTreatmentAnoxic Encephalopathy / Cardiac Arrest / Refractory seizure disorders1
Not AvailableRecruitingTreatmentHaematological disorders / Haemoglobinopathies congenital / Immunodeficiencies1
Not AvailableTerminatedNot AvailableNeonatal Convulsions1
Not AvailableTerminatedTreatmentSubarachnoid Hemorrhage1
Not AvailableUnknown StatusTreatmentAdults With Tonic Clonic Seizures and/or Partial Seizures1
Not AvailableUnknown StatusTreatmentEpilepsies1
Not AvailableWithdrawnSupportive CareBrain and Central Nervous System Tumors / Seizures / Unspecified Adult Solid Tumor, Protocol Specific1

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, extended releaseOral1000 mg/1
Tablet, extended releaseOral1500 mg/1
TabletOral250 mg
TabletOral500 mg
TabletOral750 mg
Tablet, film coatedOral750 mg/1
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/100mL
Injection, solutionIntravenous500 mg/5mL
Injection, solution, concentrateIntravenous100 mg/1mL
Injection, solution, concentrateIntravenous500 mg/5mL
SolutionOral100 mg/1mL
SolutionOral1000 mg/10mL
SolutionOral1500 mg/15mL
SolutionOral500 mg/5mL
TabletOral1000 mg/1
TabletOral250 mg/1
TabletOral500 mg/1
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, film coatedOral1000 mg
Tablet, film coatedOral250 mg
Tablet, film coatedOral500 mg
Tablet, film coatedOral750 mg
SolutionOral100 mg/ml
Injection, solution, concentrateIntravenous100 mg/ml
PowderNot applicable1 g/1g
SolutionIntravenous
SolutionOral
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)
US8802142Yes2014-08-122031-12-07Us
US7858122No2010-12-282028-09-17Us
US6471992No2002-10-292018-02-20Us
US9463160No2016-10-112018-02-20Us
US9669009No2017-06-062034-03-14Us
US9339489No2016-05-172034-03-14Us
US8431156No2013-04-302027-10-31Us
US8535717No2013-09-172026-02-22Us
US8425938No2013-04-232026-02-22Us
US8163306No2012-04-242027-09-03Us
US8470367No2013-06-252026-02-22Us
Additional Data Available
  • Filed On
    Filed On

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

    Learn more

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

Taxonomy

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
Alpha-amino acid or derivatives / Fatty amide / Pyrrolidone / 2-pyrrolidone / Fatty acyl / N-alkylpyrrolidine / Pyrrolidine / Tertiary carboxylic acid amide / Carboxamide group / Lactam
show 12 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
pyrrolidin-2-ones (CHEBI:6437)

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 September 23, 2019 04:11