LEVETIRACETAM

Search structure
Trade Names:
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N03AX14
UNII: 44YRR34555

Structure
InChI Key HPHUVLMMVZITSG-LURJTMIESA-N
Smile CC[C@@H](C(N)=O)N1CCCC1=O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H14N2O2
Molecular Weight 170.21
AlogP -0.13
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 63.4
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 12.0

Pharmacology

Action Mechanism of Action Reference
MODULATOR Synaptic vesicle glycoprotein 2A modulator DailyMed
Primary Target
synaptic vesicle glycoprotein 2A

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Epilepsy, Tonic-Clonic 4 D004830 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Panic Disorder 3 D016584 ClinicalTrials
Status Epilepticus 3 D013226 ClinicalTrials
Substance Withdrawal Syndrome 3 D013375 ClinicalTrials
Subarachnoid Hemorrhage 3 D013345 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Alcoholism 3 D000437 ClinicalTrials
Movement Disorders 3 D009069 ClinicalTrials
Alcoholism 3 D000437 ClinicalTrials
Epilepsies, Partial 3 D004828 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Torticollis 2 D014103 ClinicalTrials
Epilepsy, Absence 2 D004832 ClinicalTrials
Psychotic Disorders 2 D011618 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Bipolar Disorder 2 D001714 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Obsessive-Compulsive Disorder 2 D009771 ClinicalTrials
Restless Legs Syndrome 2 D012148 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Dyskinesia, Drug-Induced 2 D004409 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Polyneuropathies 2 D011115 ClinicalTrials
Epilepsy, Reflex 2 D020195 ClinicalTrials
Neuralgia, Postherpetic 2 D051474 ClinicalTrials
Essential Tremor 1 D020329 ClinicalTrials
Canavan Disease 1 D017825 ClinicalTrials
Aphasia 1 D001037 ClinicalTrials
Stroke 1 D020521 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Somnolence 23.0
Nervous system disorders Headache 19.0
Injury, poisoning and procedural complications Injury 17.0
Injury, poisoning and procedural complications Injury
General disorders and administration site conditions Asthenia 15.0
General disorders and administration site conditions Fatigue 15.0
Nervous system disorders Headache
Infections and infestations Nasopharyngitis 15.0
Nervous system disorders Somnolence 15.0
Gastrointestinal disorders Vomiting 15.0
Nervous system disorders Somnolence 14.9
General disorders and administration site conditions Asthenia 14.1
General disorders and administration site conditions Asthenia 14.0
Nervous system disorders Headache 14.0
Infections and infestations Nasopharyngitis 14.0
Nervous system disorders Headache
Infections and infestations Infection 13.2
Nervous system disorders Headache 13.1
General disorders and administration site conditions Decreased appetite 13.0
Nervous system disorders Headache
Infections and infestations Infection 13.0
Infections and infestations Rhinitis 13.0
Nervous system disorders Somnolence 13.0
Gastrointestinal disorders Vomiting
Psychiatric disorders Hostility 12.0
General disorders and administration site conditions Irritability 12.0
Infections and infestations Nasopharyngitis
Nervous system disorders Somnolence 12.0
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Asthenia 11.0
Respiratory, thoracic and mediastinal disorders Cough 11.0
General disorders and administration site conditions Fatigue 11.0
Nervous system disorders Somnolence
Injury, poisoning and procedural complications Injury 10.3
Psychiatric disorders Aggression 10.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 10.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 10.0
Injury, poisoning and procedural complications Injury
Psychiatric disorders Nervousness 10.0
Gastrointestinal disorders Pharyngitis 10.0
Nervous system disorders Somnolence
Psychiatric disorders Tension 10.0
General disorders and administration site conditions Asthenia
Nervous system disorders Somnolence
Cardiac disorders Dizziness 9.2
Gastrointestinal disorders Abdominal pain upper 9.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 9.0
Respiratory, thoracic and mediastinal disorders Cough 9.0
Cardiac disorders Dizziness 9.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 9.0
Nervous system disorders Somnolence
Gastrointestinal disorders Abdominal pain upper
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 8.0
Gastrointestinal disorders Diarrhoea 8.0
General disorders and administration site conditions Fatigue
Gastrointestinal disorders Gastrointestinal disorder 8.0
Infections and infestations Infection
Infections and infestations Influenza 8.0
Musculoskeletal and connective tissue disorders Neck pain 8.0
Psychiatric disorders Personality disorder 8.0
Gastrointestinal disorders Pharyngitis
Infections and infestations Rhinitis
Nervous system disorders Somnolence
Nervous system disorders Somnolence 8.0
Infections and infestations Infection
Psychiatric disorders Abnormal behaviour 7.0
Respiratory, thoracic and mediastinal disorders Cough
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness 7.0
Gastrointestinal disorders Gastrointestinal disorder
General disorders and administration site conditions Irritability 7.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 7.0
Infections and infestations Nasopharyngitis 7.0
General disorders and administration site conditions Pain 7.0
Psychiatric disorders Personality disorder
Gastrointestinal disorders Pharyngitis 7.0
Psychiatric disorders Hostility 6.93
Convulsion
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 6.5
Psychiatric disorders Affect lability 6.0
Nervous system disorders Agitation 6.0
Convulsion 6.0
Gastrointestinal disorders Diarrhoea 6.0
Psychiatric disorders Hostility
Infections and infestations Influenza
General disorders and administration site conditions Irritability 6.0
General disorders and administration site conditions Lethargy 6.0
Psychiatric disorders Mood swings 6.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 6.0
Gastrointestinal disorders Pharyngitis 6.0
Gastrointestinal disorders Pharyngitis 5.7
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Gastrointestinal pain
Psychiatric disorders Affect lability 5.0
Psychiatric disorders Aggression
General disorders and administration site conditions Asthenia
Respiratory, thoracic and mediastinal disorders Cough
Psychiatric disorders Depression 5.0
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness
Cardiac disorders Dizziness 5.0
General disorders and administration site conditions Fatigue
Infections and infestations Influenza 5.0
Nervous system disorders Insomnia 5.0
Psychiatric disorders Mood swings 5.0
Infections and infestations Nasopharyngitis
Gastrointestinal disorders Nausea 5.0
Ear and labyrinth disorders Vertigo 5.0
Nervous system disorders Somnolence 4.61
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Nausea
Nervous system disorders Somnolence 4.42
Cardiac disorders Dizziness
Infections and infestations Rhinitis 4.3
Gastrointestinal disorders Diarrhoea 4.2
Infections and infestations Influenza 4.2
Gastrointestinal disorders Nausea 4.2
Psychiatric disorders Abnormal behaviour
Psychiatric disorders Affect lability
Nervous system disorders Agitation 4.0
Renal and urinary disorders Albuminuria 4.0
Musculoskeletal and connective tissue disorders Back pain 4.0
General disorders and administration site conditions Decreased appetite 4.0
Psychiatric disorders Depression 4.0
Skin and subcutaneous tissue disorders Dermatitis
Cardiac disorders Dizziness
Blood and lymphatic system disorders Ecchymosis 4.0
Gastrointestinal disorders Gastroenteritis 4.0
Injury, poisoning and procedural complications Head injury 4.0
Infections and infestations Influenza
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Psychiatric disorders Mood swings
Psychiatric disorders Nervousness 4.0
Gastrointestinal disorders Pharyngitis
Skin and subcutaneous tissue disorders Rash
Infections and infestations Rhinitis 4.0
Nervous system disorders Somnolence 4.0
Psychiatric disorders Tension 4.0
Psychiatric disorders Nervousness 3.9
Psychiatric disorders Tension 3.9
Gastrointestinal disorders Abdominal pain 3.7
Gastrointestinal disorders Gastrointestinal pain 3.7
Gastrointestinal disorders Pharyngitis
Convulsion
Gastrointestinal disorders Dyspepsia
Infections and infestations Urinary tract infection
Psychiatric disorders Anxiety 3.33
Nervous system disorders Somnolence
Psychiatric disorders Affect lability 3.0
Psychiatric disorders Anxiety 3.0
General disorders and administration site conditions Asthenia
Nervous system disorders Ataxia 3.0
Eye disorders Conjunctivitis 3.0
Gastrointestinal disorders Constipation 3.0
Injury, poisoning and procedural complications Contusion 3.0
Nervous system disorders Coordination abnormal 3.0
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Decreased appetite 3.0
Psychiatric disorders Depression 3.0
Cardiac disorders Dizziness
Infections and infestations Influenza 3.0
Nervous system disorders Insomnia
Nervous system disorders Insomnia 3.0
Psychiatric disorders Mood swings 3.0
Gastrointestinal disorders Nausea
General disorders and administration site conditions Pain
Infections and infestations Rhinitis
Nervous system disorders Somnolence
Ear and labyrinth disorders Vertigo
Ear and labyrinth disorders Vertigo 3.0
Convulsion 2.99
General disorders and administration site conditions Asthenia 2.97
Nervous system disorders Somnolence 2.97
Convulsion
Skin and subcutaneous tissue disorders Dermatitis 2.8
Gastrointestinal disorders Dyspepsia 2.8
Nervous system disorders Insomnia
Skin and subcutaneous tissue disorders Rash 2.8
Infections and infestations Rhinitis
Nervous system disorders Ataxia 2.5
Ear and labyrinth disorders Vertigo 2.5
General disorders and administration site conditions Decreased appetite 2.4
Eye disorders Diplopia 2.4
Convulsion 2.38
Psychiatric disorders Depression
Gastrointestinal disorders Vomiting 2.2
Respiratory, thoracic and mediastinal disorders Cough 2.1
Psychiatric disorders Hostility 2.1
Infections and infestations Sinusitis 2.1
Psychiatric disorders Hostility
Psychiatric disorders Affect lability 2.0
Eye disorders Amblyopia 2.0
Nervous system disorders Amnesia 2.0
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 2.0
Musculoskeletal and connective tissue disorders Arthralgia 2.0
Immune system disorders Asthma 2.0
Nervous system disorders Confusional state 2.0
Eye disorders Conjunctivitis
Eye disorders Conjunctivitis 2.0
Nervous system disorders Coordination abnormal
Respiratory, thoracic and mediastinal disorders Cough 2.0
General disorders and administration site conditions Decreased appetite
Metabolism and nutrition disorders Dehydration 2.0
Psychiatric disorders Depressed mood 2.0
Psychiatric disorders Depression
Psychiatric disorders Depression 2.0
Skin and subcutaneous tissue disorders Dermatitis bullous 2.0
Eye disorders Diplopia 2.0
Cardiac disorders Dizziness
Ear and labyrinth disorders Ear pain 2.0
General disorders and administration site conditions Face oedema 2.0
General disorders and administration site conditions Feeling abnormal 2.0
Gastrointestinal disorders Gastroenteritis
Gastrointestinal disorders Gastroenteritis 2.0
Psychiatric disorders Hostility 2.0
Nervous system disorders Hyperreflexia 2.0
Nervous system disorders Hypersomnia 2.0
Infections and infestations Influenza
Nervous system disorders Insomnia 2.0
General disorders and administration site conditions Irritability
General disorders and administration site conditions Irritability 2.0
General disorders and administration site conditions Lethargy
Injury, poisoning and procedural complications Ligament sprain 2.0
Psychiatric disorders Mood swings 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion
Musculoskeletal and connective tissue disorders Neck pain
Musculoskeletal and connective tissue disorders Neck pain 2.0
Psychiatric disorders Nervousness
Psychiatric disorders Nervousness 2.0
Nervous system disorders Paraesthesia 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Infections and infestations Rash pustular 2.0
Infections and infestations Rhinitis 2.0
Infections and infestations Sinusitis 2.0
Skin and subcutaneous tissue disorders Skin discolouration 2.0
Nervous system disorders Somnolence
Nervous system disorders Somnolence 2.0
Psychiatric disorders Tension
Psychiatric disorders Tension 2.0
Renal and urinary disorders Urine abnormality 2.0
Investigations Urine analysis abnormal 2.0
Infections and infestations Viral infection 2.0
Gastrointestinal disorders Vomiting
Nervous system disorders Paraesthesia 1.9
Infections and infestations Urinary tract infection 1.9
Nervous system disorders Somnolence
Investigations Body temperature increased
Respiratory, thoracic and mediastinal disorders Cough
Eye disorders Diplopia
Psychiatric disorders Nervousness
Nervous system disorders Paraesthesia
Psychiatric disorders Tension
Nervous system disorders Tremor
Psychiatric disorders Anxiety
Psychiatric disorders Depressed mood 1.67
Psychiatric disorders Depression 1.67
Eye disorders Diplopia 1.67
Nervous system disorders Hypersomnia 1.67
Nervous system disorders Insomnia 1.67
General disorders and administration site conditions Irritability 1.67
Psychiatric disorders Nervousness 1.67
Nervous system disorders Somnolence 1.67
Psychiatric disorders Tension 1.67
Cardiac disorders Dizziness 1.64
Psychiatric disorders Affect lability 1.6
Nervous system disorders Amnesia 1.6
Psychiatric disorders Anxiety 1.6
Psychiatric disorders Mood swings 1.6
Nervous system disorders Somnolence
Blood and lymphatic system disorders Ecchymosis 1.5
Social circumstances Mental disability 1.5
Nervous system disorders Thinking abnormal 1.5
Gastrointestinal disorders Tooth disorder 1.5
Nervous system disorders Tremor 1.5
Cardiac disorders Dizziness 1.43
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Eye disorders Amblyopia
Nervous system disorders Ataxia
Infections and infestations Bronchitis
Social circumstances Mental disability
Nervous system disorders Thinking abnormal
Ear and labyrinth disorders Vertigo
General disorders and administration site conditions Asthenia 1.34
General disorders and administration site conditions Asthenia 1.3
Investigations Body temperature increased 1.3
Infections and infestations Bronchitis 1.3
Cardiac disorders Chest pain 1.3
Investigations Drug level increased 1.3
Eye disorders Amblyopia 1.2
Gastrointestinal disorders Gastroenteritis 1.2
Gastrointestinal disorders Gingivitis 1.2
Ear and labyrinth disorders Otitis media 1.2
Investigations Weight increased 1.2
Nervous system disorders Headache 1.19
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Psychiatric disorders Anxiety
Cardiac disorders Chest pain
Blood and lymphatic system disorders Ecchymosis
Investigations Weight increased
Psychiatric disorders Affect lability
Nervous system disorders Agitation
Nervous system disorders Amnesia
Psychiatric disorders Anxiety
Immune system disorders Asthma
Nervous system disorders Ataxia
Gastrointestinal disorders Constipation
Injury, poisoning and procedural complications Contusion
Respiratory, thoracic and mediastinal disorders Cough
Metabolism and nutrition disorders Dehydration
Psychiatric disorders Depression
Eye disorders Diplopia
Cardiac disorders Dizziness 1.0
Ear and labyrinth disorders Ear pain
Blood and lymphatic system disorders Ecchymosis
General disorders and administration site conditions Face oedema
Psychiatric disorders Hostility
Nervous system disorders Hyperreflexia
Infections and infestations Influenza
General disorders and administration site conditions Irritability
Injury, poisoning and procedural complications Ligament sprain
Psychiatric disorders Mood swings
Musculoskeletal and connective tissue disorders Neck pain
Nervous system disorders Paraesthesia
Psychiatric disorders Psychotic disorder 1.0
Infections and infestations Sinusitis
Renal and urinary disorders Urine abnormality
Investigations Urine analysis abnormal
Ear and labyrinth disorders Vertigo
Infections and infestations Viral infection
Investigations Drug level increased
Gastrointestinal disorders Gastroenteritis
Ear and labyrinth disorders Otitis media
Infections and infestations Sinusitis
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia
Gastrointestinal disorders Gingivitis
Psychiatric disorders Hostility
Gastrointestinal disorders Tooth disorder
Nervous system disorders Headache
Psychiatric disorders Affect lability
Nervous system disorders Amnesia
Psychiatric disorders Mood swings

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
22.75
Psychiatric disorders
14.23
General disorders and administration site conditions
10.45
Injury, poisoning and procedural complications
10.06
Pregnancy, puerperium and perinatal conditions
5.3
Investigations
3.59
Musculoskeletal and connective tissue disorders
3.13
Vascular disorders
3.03
Gastrointestinal disorders
3.02
Skin and subcutaneous tissue disorders
3.01
Respiratory, thoracic and mediastinal disorders
2.89
Cardiac disorders
2.69
Infections and infestations
2.19
Metabolism and nutrition disorders
2.14

Cross References

Resources Reference
CAS NUMBER 102767-28-2
ChEBI 6437
ChEMBL CHEMBL1286
DrugBank DB01202
DrugCentral 1563
EPA CompTox DTXSID9023207
FDA SRS 44YRR34555
Guide to Pharmacology 6826
KEGG C07841
PubChem 5284583
SureChEMBL SCHEMBL118843
ZINC ZINC000001547851
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