Identification

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

Levetiracetam is an anticonvulsant medication used to treat epilepsy. Levetiracetam may selectively prevent hypersynchronization of epileptiform burst firing and propagation of seizure activity. Levetiracetam binds to the synaptic vesicle protein SV2A, which is thought to be involved in the regulation of vesicle exocytosis. Although the molecular significance of levetiracetam binding to synaptic vesicle protein SV2A is not understood, levetiracetam and related analogs showed a rank order of affinity for SV2A which correlated with the potency of their antiseizure activity in audiogenic seizure-prone mice.

Structure
Thumb
Synonyms
  • Levetiracetam
  • Levetiracetame
  • Levetiracetamum
  • Levitiracetam
External IDs
N03AX14 / UCB 22059 / UCB L059 / UCB-22059 / UCB-L059
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act LevetiracetamTablet250 mgOralActavis Pharma Company2005-12-07Not applicableCanada
Act LevetiracetamTablet750 mgOralActavis Pharma Company2005-12-07Not applicableCanada
Act LevetiracetamTablet500 mgOralActavis 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 coated500 mg/1OralUcb Inc2000-04-24Not applicableUs50474 0595 40 nlmimage10 ec15f63f
KeppraTablet, film coated500 mg/1OralMckesson Rxpak Inc2000-04-24Not applicableUs
KeppraTablet250 mgOralUcb Inc2003-07-23Not applicableCanada
KeppraTablet, film coated750 mg/1OralPhysicians Total Care, Inc.2005-04-15Not applicableUs50474 0596 40 nlmimage10 04160230
KeppraTablet, film coated500 mg/1OralStat Rx USA2000-04-24Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abbott-levetiracetamTablet750 mgOralAbbott2014-05-302015-12-31Canada
Abbott-levetiracetamTablet250 mgOralAbbott2014-05-302015-12-31Canada
Abbott-levetiracetamTablet500 mgOralAbbott2014-05-302015-12-31Canada
Apo-levetiracetamTablet250 mgOralApotex Corporation2006-10-20Not applicableCanada
Apo-levetiracetamTablet750 mgOralApotex Corporation2006-10-20Not applicableCanada
Apo-levetiracetamTablet500 mgOralApotex Corporation2006-10-20Not applicableCanada
Auro-levetiracetamTablet250 mgOralAuro Pharma Inc2012-02-14Not applicableCanada
Auro-levetiracetamTablet750 mgOralAuro Pharma Inc2012-02-14Not applicableCanada
Auro-levetiracetamTablet500 mgOralAuro Pharma Inc2012-03-15Not applicableCanada
Ava-levetiracetamTablet500 mgOralAvanstra Inc2011-10-112014-08-21Canada
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

Used as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

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. Protection was observed, however, against secondarily generalized activity from focal seizures induced by pilocarpine and kainic acid, two chemoconvulsants that induce seizures that mimic some features of human complex partial seizures with secondary generalization. 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. Levetiracetam is thought to stimulate synaptic vesicle protein 2A (SV2A), inhibiting neurotransmitter release.

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

Rapidly and almost completely absorbed after oral administration (99%). Peak plasma concentrations occurring in about an hour following oral administration in fasted subjects.

Volume of distribution
Not Available
Protein binding

Very low (<10%)

Metabolism

The major metabolic pathway of levetiracetam (24% of dose) is an enzymatic hydrolysis of the acetamide group. No CYP450 metabolism detected.

Route of elimination

Sixty-six percent (66%) of the dose is renally excreted unchanged. The metabolites have no known pharmacological activity and are renally excreted. The mechanism of excretion is glomerular filtration with subsequent partial tubular reabsorption.

Half life

6-8 hours

Clearance
  • 0.96 mL/min/kg
Toxicity

Side effects include aggression, agitation, coma, drowsiness, reduced consciousness, slowed breathing

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

Interactions

Drug Interactions
DrugInteraction
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.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Levetiracetam is combined with 3,4-Methylenedioxyamphetamine.
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.
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
Not Available
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
FDA label
Download (52.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentAphasia / Strokes1
1CompletedNot AvailableHealthy Volunteers6
1CompletedBasic ScienceEpilepsies1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentBenign Childhood Epilepsy With Centro-Temporal Spikes1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHuman Volunteers2
1CompletedTreatmentSeizures1
1RecruitingTreatmentPompe's Disease1
1, 2CompletedTreatmentDisorder of Fetus or Newborn / Seizures1
1, 2CompletedTreatmentEpilepsies / Malaria, Cerebral / Seizures1
1, 2CompletedTreatmentSeizures1
1, 2CompletedTreatmentSeizures / Term Neonates1
1, 2CompletedTreatmentTremor, Essential1
1, 2Not Yet RecruitingTreatmentNeonatal Convulsions1
1, 2RecruitingTreatmentNeonatal Convulsions1
2Active Not RecruitingTreatmentSickle Cell Disorders1
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
2CompletedTreatmentAlcoholism / 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
2Not Yet RecruitingTreatmentGlioblastoma Multiforme (GBM)1
2Not Yet RecruitingTreatmentGlioma of Brain / Gliomas / Neoplasms, Brain1
2RecruitingOtherPsychosis / Schizo Affective Disorder / Schizophrenic Disorders / Schizophreniform1
2RecruitingPreventionAPOE 41
2RecruitingTreatmentAlzheimer's Disease (AD)1
2RecruitingTreatmentNeonatal Convulsions1
2RecruitingTreatmentNeuroblastomas1
2SuspendedTreatmentCervical Dystonia1
2TerminatedTreatmentAcute Myelogenous Leukaemia (AML) / Refractory Acute Myelogenous Leukemia1
2TerminatedTreatmentAlcohol Abuse / Alcohol Dependence / Alcoholism1
2Unknown StatusTreatmentLevodopa Induced Dyskinesia (LID)1
2Unknown StatusTreatmentRefractory seizure disorders1
2WithdrawnTreatmentSeizure, Alcohol Related1
2, 3CompletedTreatmentPost-Traumatic Stress Disorder (PTSD)1
2, 3TerminatedTreatmentObsessive-Compulsive Disorder (OCD)1
3Active Not RecruitingTreatmentAdverse Effects / Epilepsy, Localization Related1
3CompletedNot AvailableEpilepsy, Generalized1
3CompletedNot AvailableEpilepsy, Localization Related3
3CompletedNot AvailableEpilepsy, Tonic-Clonic1
3CompletedNot AvailableGeneralized Convulsive Epilepsy1
3CompletedPreventionAlcohol Dependence / Alcoholic Relapse1
3CompletedPreventionSubarachnoid Hemorrhage1
3CompletedTreatmentAlcohol Withdrawal Syndrome(AWS)1
3CompletedTreatmentEpilepsies7
3CompletedTreatmentEpilepsies / Grand mal Generalized tonic-clonic seizure3
3CompletedTreatmentEpilepsies / Partial1
3CompletedTreatmentEpilepsies / Partial onset seizure Epilepsy4
3CompletedTreatmentEpilepsy, Generalized1
3CompletedTreatmentEpilepsy, Localization Related4
3CompletedTreatmentEpilepsy, Tonic-Clonic1
3CompletedTreatmentGeneralized Convulsive Epilepsy1
3CompletedTreatmentPanic Disorders1
3CompletedTreatmentStatus; Epilepticus, Tonic-clonic1
3CompletedTreatmentTardive Dyskinesia1
3CompletedTreatmentPartial onset seizure Epilepsy1
3Not Yet RecruitingTreatment: Acute intraCerebral Haemorrhage1
3RecruitingHealth Services ResearchEpilepsies1
3RecruitingTreatmentBenzodiazepine Refractory Status Epilepticus1
3RecruitingTreatmentPartial onset seizure Epilepsy1
3TerminatedPreventionPost-Traumatic Seizure Disorder1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentDrug Resistant / Epilepsies1
3TerminatedTreatmentEpilepsies / Seizures1
3TerminatedTreatmentEpilepsy, Localization Related1
3Unknown StatusTreatmentEpilepsies1
3Unknown StatusTreatmentSeizures, Epileptic / Strokes1
3WithdrawnTreatmentEpilepsies / Refractory seizure disorders1
4Active Not RecruitingTreatmentEpilepsies1
4CompletedNot AvailableEpilepsies1
4CompletedNot AvailableEpilepsy, Localization Related2
4CompletedBasic ScienceHealthy Volunteers / Impaired Renal Function1
4CompletedPreventionManic State Associated With Corticosteroid Use / Memory Loss Associated With Corticosteroid Use1
4CompletedTreatmentAlcoholism1
4CompletedTreatmentBody Dysmorphic Disorders1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentEpilepsies8
4CompletedTreatmentEpilepsies / Primary Brain Tumors1
4CompletedTreatmentEpilepsy, Localization Related4
4CompletedTreatmentGilles de la Tourette's Syndrome / Tic Disorders1
4CompletedTreatmentGrand mal Generalized tonic-clonic seizure1
4CompletedTreatmentPainful Polyneuropathy1
4CompletedTreatmentPain / Spinal Cord Injuries (SCI)1
4CompletedTreatmentParkinson's Disease (PD)1
4CompletedTreatmentSubarachnoid Hemorrhage / Traumatic Brain Injury (TBI)1
4RecruitingNot AvailableEpilepsies1
4RecruitingSupportive CareIntracranial Aneurysms / Seizures1
4RecruitingTreatmentAcute Kidney Injury (AKI) / Impaired Renal Function / Pharmacokinetics / Renal Failure1
4RecruitingTreatmentBrain Cancer / Cancer of Brain / Cancer of the Brain / Neoplasms, Brain / Seizures1
4RecruitingTreatmentEpilepsies1
4RecruitingTreatmentGliomas1
4RecruitingTreatmentNeonatal Convulsions1
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 AvailableEpilepsies / Seizures1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedBasic ScienceAlzheimer's Disease (AD) / Seizures1
Not AvailableCompletedTreatmentAlcohol Abuse / Drug Abuse1
Not AvailableCompletedTreatmentChildhood Absence Epilepsy / Epilepsies / Seizures1
Not AvailableCompletedTreatmentDepression, Bipolar1
Not AvailableCompletedTreatmentEpilepsies1
Not AvailableCompletedTreatmentFibromyalgia1
Not AvailableCompletedTreatmentMigraines1
Not AvailableCompletedTreatmentPostoperative pain1
Not AvailableCompletedTreatmentPremenstrual Dysphoric Disorder1
Not AvailableCompletedTreatmentSeizures4
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cyanide Poisoning / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / Gynaecological infection / Headaches / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperlipidemias / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombosis / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
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
Tablet, extended releaseOral1000 mg/1
Tablet, extended releaseOral1500 mg/1
TabletOral250 mg
TabletOral500 mg
TabletOral750 mg
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 coatedOral750 mg/1
Tablet, film coated, extended releaseOral1000 mg/1
Tablet, film coatedOral1000 mg
Tablet, film coatedOral250 mg
Tablet, film coatedOral500 mg
Tablet, film coatedOral750 mg
SolutionOral100 mg/ml
Tablet, film coated, extended releaseOral500 mg/1
Tablet, film coated, extended releaseOral750 mg/1
Injection, solution, concentrateIntravenous100 mg/ml
TabletOral1000 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)
US8802142Yes2011-12-072031-12-07Us
US7858122No2008-09-172028-09-17Us
US6471992No1998-02-202018-02-20Us
US9463160No1998-02-202018-02-20Us
US9669009No2014-03-142034-03-14Us
US9339489No2014-03-142034-03-14Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
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
Human
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. Lambeng N, Grossmann M, Chatelain P, Fuks B: Solubilization and immunopurification of rat brain synaptic vesicle protein 2A with maintained binding properties. Neurosci Lett. 2006 May 1;398(1-2):107-12. Epub 2006 Jan 24. [PubMed:16434140]
  4. Gillard M, Chatelain P, Fuks B: Binding characteristics of levetiracetam to synaptic vesicle protein 2A (SV2A) in human brain and in CHO cells expressing the human recombinant protein. Eur J Pharmacol. 2006 Apr 24;536(1-2):102-8. Epub 2006 Mar 10. [PubMed:16556440]
  5. Newton HB, Dalton J, Goldlust S, Pearl D: Retrospective analysis of the efficacy and tolerability of levetiracetam in patients with metastatic brain tumors. J Neurooncol. 2007 Sep;84(3):293-6. Epub 2007 Apr 13. [PubMed:17431542]
  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]
Kind
Protein
Organism
Human
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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Transporters

Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 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]

Drug created on June 13, 2005 07:24 / Updated on September 25, 2018 17:45