VIGABATRIN

Search structure
Trade Names:
Synonyms:
Status: Approved (2009)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: N03AG04
UNII: GR120KRT6K

Structure
InChI Key PJDFLNIOAUIZSL-UHFFFAOYSA-N
Smile C=CC(N)CCC(=O)O
InChI
InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

Physicochemical Descriptors

Property Name Value
Molecular Formula C6H11NO2
Molecular Weight 129.16
AlogP 0.36
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 63.32
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 9.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Gamma-amino-N-butyrate transaminase inhibitor FDA PubMed
Primary Target
4-aminobutyrate aminotransferase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- 39720 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 79

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Spasms, Infantile 4 D013036 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Tuberous Sclerosis 2 D014402 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Obesity 2 D009765 ClinicalTrials
Amphetamine-Related Disorders 2 D019969 ClinicalTrials
Tourette Syndrome 1 D005879 ClinicalTrials

Related Entries

MCS

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Upper respiratory tract infection 51.0
Infections and infestations Upper respiratory tract infection 46.0
Ear and labyrinth disorders Otitis media 44.0
General disorders and administration site conditions Asthenia 40.0
General disorders and administration site conditions Fatigue 40.0
Nervous system disorders Headache 33.0
Nervous system disorders Headache
Ear and labyrinth disorders Otitis media 30.0
Investigations Body temperature increased 29.0
Cardiac disorders Dizziness 26.0
Nervous system disorders Headache 26.0
Nervous system disorders Somnolence 26.0
Cardiac disorders Dizziness 24.0
General disorders and administration site conditions Asthenia 23.0
General disorders and administration site conditions Fatigue 23.0
General disorders and administration site conditions Irritability 23.0
Nervous system disorders Somnolence 22.0
Infections and infestations Viral infection 20.0
Gastrointestinal disorders Vomiting 20.0
Investigations Body temperature increased 19.0
Eye disorders Nystagmus 19.0
Nervous system disorders Somnolence 19.0
Infections and infestations Viral infection 19.0
Cardiac disorders Dizziness
Nervous system disorders Somnolence 17.0
Investigations Weight increased 17.0
General disorders and administration site conditions Asthenia
Nervous system disorders Coordination abnormal 16.0
Gastrointestinal disorders Diarrhoea 16.0
Eye disorders Diplopia 16.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Irritability 16.0
Nervous system disorders Memory impairment 16.0
Nervous system disorders Tremor 16.0
Eye disorders Vision blurred 16.0
Nervous system disorders Tremor 15.0
Nervous system disorders Confusional state 14.0
Gastrointestinal disorders Constipation 14.0
Respiratory, thoracic and mediastinal disorders Cough 14.0
Psychiatric disorders Depression 14.0
Infections and infestations Ear infection 14.0
General disorders and administration site conditions Feeling abnormal 14.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 14.0
Infections and infestations Nasopharyngitis 14.0
Gastrointestinal disorders Vomiting 14.0
Investigations Weight increased 14.0
Gastrointestinal disorders Diarrhoea 13.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 13.0
Eye disorders Nystagmus 13.0
Infections and infestations Pneumonia 13.0
Nervous system disorders Somnolence
Eye disorders Vision blurred 13.0
Gastrointestinal disorders Constipation 12.0
Gastrointestinal disorders Diarrhoea 12.0
General disorders and administration site conditions Gait disturbance 12.0
Nervous system disorders Insomnia 12.0
Skin and subcutaneous tissue disorders Dermatitis 11.0
Infections and infestations Pneumonia 11.0
Skin and subcutaneous tissue disorders Rash 11.0
Musculoskeletal and connective tissue disorders Arthralgia 10.0
Gastrointestinal disorders Diarrhoea 10.0
Nervous system disorders Insomnia 10.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 10.0
Infections and infestations Nasopharyngitis
Gastrointestinal disorders Nausea 10.0
Infections and infestations Upper respiratory tract infection 10.0
General disorders and administration site conditions Asthenia 9.0
General disorders and administration site conditions Decreased appetite 9.0
Nervous system disorders Disturbance in attention 9.0
Reproductive system and breast disorders Dysmenorrhoea 9.0
General disorders and administration site conditions Fatigue 9.0
Musculoskeletal and connective tissue disorders Muscle twitching 9.0
Infections and infestations Nasopharyngitis 9.0
Eye disorders Nystagmus
Infections and infestations Sinusitis 9.0
Infections and infestations Upper respiratory tract infection 9.0
Gastrointestinal disorders Vomiting 9.0
Infections and infestations Candida infection 8.0
Gastrointestinal disorders Constipation 8.0
Respiratory, thoracic and mediastinal disorders Cough 8.0
Skin and subcutaneous tissue disorders Dermatitis 8.0
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Rash 8.0
Nervous system disorders Somnolence 8.0
Nervous system disorders Tremor
General disorders and administration site conditions Asthenia 7.0
Musculoskeletal and connective tissue disorders Back pain 7.0
Investigations Body temperature increased 7.0
Convulsion 7.0
Nervous system disorders Coordination abnormal 7.0
Respiratory, thoracic and mediastinal disorders Cough
General disorders and administration site conditions Decreased appetite 7.0
Gastrointestinal disorders Diarrhoea
Eye disorders Diplopia 7.0
Infections and infestations Ear infection 7.0
Expressive language disorder 7.0
General disorders and administration site conditions Gait disturbance
Infections and infestations Influenza 7.0
General disorders and administration site conditions Irritability
General disorders and administration site conditions Irritability 7.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 7.0
General disorders and administration site conditions Lethargy 7.0
Nervous system disorders Memory impairment 7.0
Social circumstances Mental disability 7.0
Cardiac disorders Oedema peripheral 7.0
Nervous system disorders Paraesthesia 7.0
Nervous system disorders Sensory disturbance 7.0
Nervous system disorders Thinking abnormal 7.0
Infections and infestations Upper respiratory tract infection 7.0
Gastrointestinal disorders Vomiting 7.0
Psychiatric disorders Abnormal behaviour 6.0
Psychiatric disorders Depression 6.0
Gastrointestinal disorders Diarrhoea 6.0
General disorders and administration site conditions Gait disturbance 6.0
Musculoskeletal and connective tissue disorders Hypotonia 6.0
Infections and infestations Influenza 6.0
Surgical and medical procedures Muscle relaxant therapy 6.0
Ear and labyrinth disorders Otitis media 6.0
Musculoskeletal and connective tissue disorders Pain in extremity 6.0
Nervous system disorders Sinus headache 6.0
Nervous system disorders Somnolence 6.0
Nervous system disorders Status epilepticus 6.0
Nervous system disorders Tremor 6.0
Infections and infestations Upper respiratory tract infection
Infections and infestations Urinary tract infection 6.0
Gastrointestinal disorders Viral diarrhoea 6.0
Gastrointestinal disorders Vomiting
Investigations Weight increased 6.0
Gastrointestinal disorders Abdominal pain upper 5.0
Psychiatric disorders Abnormal behaviour 5.0
Nervous system disorders Abnormal dreams 5.0
Psychiatric disorders Aggression 5.0
Musculoskeletal and connective tissue disorders Arthralgia 5.0
General disorders and administration site conditions Asthenia 5.0
Infections and infestations Bronchitis 5.0
Cardiac disorders Chest pain 5.0
Eye disorders Conjunctivitis 5.0
Gastrointestinal disorders Constipation 5.0
Injury, poisoning and procedural complications Contusion 5.0
Infections and infestations Croup infectious 5.0
Psychiatric disorders Depressed mood 5.0
Skin and subcutaneous tissue disorders Dermatitis 5.0
Eye disorders Diplopia 5.0
General disorders and administration site conditions Discomfort 5.0
Reproductive system and breast disorders Dysmenorrhoea 5.0
Gastrointestinal disorders Dyspepsia 5.0
Psychiatric disorders Erectile dysfunction 5.0
Eye disorders Eye pain 5.0
General disorders and administration site conditions Feeling abnormal 5.0
Nervous system disorders Hypoaesthesia 5.0
Nervous system disorders Hyporeflexia 5.0
General disorders and administration site conditions Ill-defined disorder 5.0
General disorders and administration site conditions Increased appetite 5.0
Infections and infestations Influenza 5.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain
General disorders and administration site conditions Lethargy 5.0
General disorders and administration site conditions Malaise 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Musculoskeletal and connective tissue disorders Myalgia 5.0
Psychiatric disorders Nervousness 5.0
Eye disorders Nystagmus 5.0
Cardiac disorders Oedema peripheral 5.0
Cardiac disorders Pulmonary congestion 5.0
Skin and subcutaneous tissue disorders Rash 5.0
Respiratory, thoracic and mediastinal disorders Respiratory tract congestion 5.0
Nervous system disorders Sensory loss 5.0
Infections and infestations Sinusitis 5.0
Nervous system disorders Status epilepticus 5.0
Eye disorders Strabismus 5.0
Psychiatric disorders Tension 5.0
Gastrointestinal disorders Toothache 5.0
Infections and infestations Urinary tract infection 5.0
Ear and labyrinth disorders Vertigo 5.0
Gastrointestinal disorders Viral diarrhoea 5.0
Eye disorders Vision blurred
Gastrointestinal disorders Abdominal discomfort 4.0
Nervous system disorders Agitation 4.0
Psychiatric disorders Anxiety 4.0
General disorders and administration site conditions Asthenia
Musculoskeletal and connective tissue disorders Back pain 4.0
Investigations Body temperature increased 4.0
Nervous system disorders Confusional state 4.0
Convulsion 4.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 4.0
Nervous system disorders Disorientation 4.0
Gastrointestinal disorders Dyspepsia 4.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling abnormal 4.0
Nervous system disorders Hyperreflexia 4.0
Nervous system disorders Hypoaesthesia 4.0
Nervous system disorders Hyporeflexia 4.0
Musculoskeletal and connective tissue disorders Hypotonia 4.0
Infections and infestations Influenza
General disorders and administration site conditions Lethargy 4.0
Surgical and medical procedures Muscle relaxant therapy 4.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 4.0
Musculoskeletal and connective tissue disorders Pain in extremity
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 4.0
Nervous system disorders Sensory disturbance 4.0
Nervous system disorders Status epilepticus 4.0
Infections and infestations Upper respiratory tract infection
Infections and infestations Urinary tract infection 4.0
Gastrointestinal disorders Abdominal pain 3.0
Gastrointestinal disorders Abdominal pain upper 3.0
Psychiatric disorders Abnormal behaviour 3.0
Skin and subcutaneous tissue disorders Acne 3.0
Psychiatric disorders Anxiety
Musculoskeletal and connective tissue disorders Arthralgia
Investigations Body temperature increased
Infections and infestations Candida infection 3.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 3.0
Injury, poisoning and procedural complications Contusion 3.0
Respiratory, thoracic and mediastinal disorders Cough 3.0
Psychiatric disorders Depression
Eye disorders Diplopia
Reproductive system and breast disorders Dysmenorrhoea
Reproductive system and breast disorders Dysmenorrhoea 3.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Gastrointestinal pain 3.0
Nervous system disorders Hyperreflexia
Infections and infestations Influenza 3.0
Nervous system disorders Memory impairment
Social circumstances Mental disability 3.0
Musculoskeletal and connective tissue disorders Muscle spasms 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Myalgia 3.0
Nervous system disorders Thinking abnormal 3.0
Eye disorders Vision blurred 3.0
Investigations Weight increased
Investigations Weight increased 3.0
Gastrointestinal disorders Abdominal discomfort 2.0
Gastrointestinal disorders Abdominal distension 2.0
Gastrointestinal disorders Abdominal pain 2.0
Psychiatric disorders Abnormal behaviour
Nervous system disorders Agitation
Eye disorders Asthenopia 2.0
Musculoskeletal and connective tissue disorders Back pain
Eye disorders Conjunctivitis 2.0
Gastrointestinal disorders Constipation
Injury, poisoning and procedural complications Contusion
Nervous system disorders Coordination abnormal
Respiratory, thoracic and mediastinal disorders Cough 2.0
Gastrointestinal disorders Diarrhoea
Nervous system disorders Dysarthria 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Nervous system disorders Hyperreflexia 2.0
Infections and infestations Influenza
General disorders and administration site conditions Lethargy
Injury, poisoning and procedural complications Ligament sprain 2.0
Injury, poisoning and procedural complications Muscle strain 2.0
Gastrointestinal disorders Nausea 2.0
Psychiatric disorders Nervousness
Psychiatric disorders Nervousness 2.0
Eye disorders Nystagmus
Musculoskeletal and connective tissue disorders Osteoarthritis 2.0
Ear and labyrinth disorders Otitis media
Musculoskeletal and connective tissue disorders Pain in extremity 2.0
Nervous system disorders Paraesthesia 2.0
Nervous system disorders Postictal state 2.0
Nervous system disorders Sensory disturbance
Nervous system disorders Sinus headache 2.0
Nervous system disorders Somnolence
Nervous system disorders Status epilepticus 2.0
Psychiatric disorders Tension
Psychiatric disorders Tension 2.0
General disorders and administration site conditions Thirst 2.0
Ear and labyrinth disorders Tinnitus 2.0
Gastrointestinal disorders Toothache
Gastrointestinal disorders Toothache 2.0
Ear and labyrinth disorders Vertigo 2.0
Investigations Weight increased
General disorders and administration site conditions Wound secretion 2.0
Gastrointestinal disorders Abdominal discomfort
Gastrointestinal disorders Abdominal distension
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain upper
Psychiatric disorders Abnormal behaviour
Nervous system disorders Abnormal dreams
Nervous system disorders Abnormal dreams 1.0
General disorders and administration site conditions Asthenia
Infections and infestations Bronchitis
Cardiac disorders Chest pain
Cardiac disorders Chest pain 1.0
Nervous system disorders Confusional state
Infections and infestations Croup infectious 1.0
Psychiatric disorders Depressed mood
Nervous system disorders Disturbance in attention
Nervous system disorders Dysarthria
Expressive language disorder
Expressive language disorder 1.0
General disorders and administration site conditions Feeling abnormal
Gastrointestinal disorders Gastrointestinal pain
Nervous system disorders Hypoaesthesia
Nervous system disorders Hyporeflexia
General disorders and administration site conditions Increased appetite
General disorders and administration site conditions Increased appetite 1.0
Injury, poisoning and procedural complications Ligament sprain
Injury, poisoning and procedural complications Ligament sprain 1.0
Musculoskeletal and connective tissue disorders Muscle spasms
Injury, poisoning and procedural complications Muscle strain
Injury, poisoning and procedural complications Muscle strain 1.0
Musculoskeletal and connective tissue disorders Muscle twitching
Musculoskeletal and connective tissue disorders Muscle twitching 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Myalgia
Cardiac disorders Oedema peripheral
Musculoskeletal and connective tissue disorders Osteoarthritis
Nervous system disorders Paraesthesia
Nervous system disorders Postictal state
Cardiac disorders Pulmonary congestion
Respiratory, thoracic and mediastinal disorders Respiratory tract congestion
Nervous system disorders Sinus headache
Ear and labyrinth disorders Tinnitus
Ear and labyrinth disorders Vertigo

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
25.45
General disorders and administration site conditions
16.62
Psychiatric disorders
11.5
Respiratory, thoracic and mediastinal disorders
8.86
Infections and infestations
7.11
Eye disorders
5.37
Injury, poisoning and procedural complications
4.75
Gastrointestinal disorders
4.42
Investigations
2.39
Metabolism and nutrition disorders
2.13

Cross References

Resources Reference
CAS NUMBER 68506-86-5
ChEBI 63638
ChEMBL CHEMBL89598
DrugBank DB01080
DrugCentral 2819
EPA CompTox DTXSID4041153
FDA SRS GR120KRT6K
Human Metabolome Database HMDB0015212
Guide to Pharmacology 4821
KEGG C07500
PharmGKB PA10231
PubChem 5665
SureChEMBL SCHEMBL26714
ZINC ZINC00403618
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