OXCARBAZEPINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2000)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: N03AF02
UNII: VZI5B1W380

Structure
InChI Key CTRLABGOLIVAIY-UHFFFAOYSA-N
Smile NC(=O)N1c2ccccc2CC(=O)c2ccccc21
InChI
InChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H12N2O2
Molecular Weight 252.27
AlogP 2.64
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 63.4
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 1.110 - EST
Atmospheric OH Rate Constant 2.81E-11 cm3/molecule-sec EST
Melting Point 215.5 deg C EXP

Pharmacology

Action Mechanism of Action Reference
BLOCKER Sodium channel alpha subunit blocker PubMed PubMed DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel P2X receptor
- - - - 10
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 31-76
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 72

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Schizophrenia 3 D012559 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Epilepsies, Partial 3 D004828 ClinicalTrials
Aggression 3 D000374 ClinicalTrials
Psychomotor Agitation 3 D011595 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Neuralgia 3 D009437 ClinicalTrials
Multiple Sclerosis 2 D009103 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Cardiac disorders Dizziness 49.0
Cardiac disorders Dizziness 41.0
Eye disorders Diplopia 40.0
Nervous system disorders Somnolence 36.0
Gastrointestinal disorders Vomiting 36.0
Gastrointestinal disorders Vomiting 33.0
Cardiac disorders Dizziness 32.0
Nervous system disorders Headache 32.0
Nervous system disorders Ataxia 31.0
Nervous system disorders Headache 31.0
Nervous system disorders Somnolence 31.0
Eye disorders Diplopia 30.0
Gastrointestinal disorders Nausea 29.0
Cardiac disorders Dizziness 28.0
Nervous system disorders Headache 28.0
Nervous system disorders Somnolence 28.0
Cardiac disorders Dizziness 26.0
Nervous system disorders Headache 26.0
Eye disorders Nystagmus 26.0
Gastrointestinal disorders Nausea 25.0
Gastrointestinal disorders Vomiting 25.0
Nervous system disorders Headache
Cardiac disorders Dizziness 22.0
Gastrointestinal disorders Nausea 22.0
General disorders and administration site conditions Asthenia 21.0
General disorders and administration site conditions Fatigue 21.0
Cardiac disorders Dizziness 20.0
Eye disorders Nystagmus 20.0
Nervous system disorders Somnolence 20.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea 19.0
Nervous system disorders Somnolence 19.0
Nervous system disorders Ataxia 17.0
Eye disorders Diplopia 17.0
General disorders and administration site conditions Gait disturbance 17.0
Gastrointestinal disorders Nausea 16.0
Nervous system disorders Tremor 16.0
General disorders and administration site conditions Asthenia 15.0
Cardiac disorders Dizziness
General disorders and administration site conditions Fatigue 15.0
Nervous system disorders Headache 15.0
Gastrointestinal disorders Nausea 15.0
Ear and labyrinth disorders Vertigo 15.0
Gastrointestinal disorders Vomiting 15.0
Eye disorders Diplopia 14.0
Nervous system disorders Somnolence 14.0
Eye disorders Visual impairment 14.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Abdominal pain 13.0
General disorders and administration site conditions Asthenia 13.0
Nervous system disorders Ataxia 13.0
Eye disorders Diplopia 13.0
Cardiac disorders Dizziness
General disorders and administration site conditions Fatigue 13.0
Gastrointestinal disorders Gastrointestinal pain 13.0
Nervous system disorders Headache 13.0
Nervous system disorders Somnolence
Eye disorders Visual impairment 13.0
Gastrointestinal disorders Vomiting 13.0
General disorders and administration site conditions Asthenia 12.0
Eye disorders Diplopia 12.0
General disorders and administration site conditions Fatigue 12.0
Gastrointestinal disorders Nausea
Nervous system disorders Somnolence
Nervous system disorders Somnolence 12.0
Ear and labyrinth disorders Vertigo 12.0
Gastrointestinal disorders Abdominal pain 11.0
Gastrointestinal disorders Gastrointestinal pain 11.0
Gastrointestinal disorders Abdominal pain 10.0
Eye disorders Diplopia 10.0
General disorders and administration site conditions Gait disturbance 10.0
Gastrointestinal disorders Gastrointestinal pain 10.0
Nervous system disorders Headache
Nervous system disorders Headache 10.0
Gastrointestinal disorders Nausea
Infections and infestations Rhinitis 10.0
Infections and infestations Upper respiratory tract infection 10.0
Cardiac disorders Dizziness 9.8
General disorders and administration site conditions Asthenia
Nervous system disorders Ataxia 9.0
General disorders and administration site conditions Fatigue
Eye disorders Nystagmus 9.0
Infections and infestations Rhinitis
Nervous system disorders Somnolence
Gastrointestinal disorders Vomiting
Psychiatric disorders Affect lability 8.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 8.0
General disorders and administration site conditions Gait disturbance 8.0
Nervous system disorders Headache 8.0
Psychiatric disorders Mood swings 8.0
Nervous system disorders Tremor 8.0
Psychiatric disorders Anxiety 7.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 7.0
Nervous system disorders Ataxia 7.0
General disorders and administration site conditions Balance disorder 7.0
Nervous system disorders Confusional state 7.0
Gastrointestinal disorders Diarrhoea 7.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling abnormal 7.0
Nervous system disorders Headache
Gastrointestinal disorders Nausea 7.0
Psychiatric disorders Nervousness 7.0
Eye disorders Nystagmus 7.0
Psychiatric disorders Tension 7.0
Infections and infestations Upper respiratory tract infection 7.0
Infections and infestations Viral infection 7.0
Gastrointestinal disorders Vomiting 7.0
Cardiac disorders Dizziness 6.4
General disorders and administration site conditions Asthenia 6.0
Gastrointestinal disorders Constipation 6.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 6.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 6.0
Gastrointestinal disorders Dyspepsia 6.0
General disorders and administration site conditions Fatigue 6.0
Nervous system disorders Insomnia 6.0
Nervous system disorders Tremor 6.0
Ear and labyrinth disorders Vertigo 6.0
Eye disorders Visual impairment 6.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 6.0
Eye disorders Diplopia 5.9
Skin and subcutaneous tissue disorders Dermatitis 5.3
Skin and subcutaneous tissue disorders Rash 5.3
Gastrointestinal disorders Vomiting 5.3
Nervous system disorders Ataxia 5.2
Gastrointestinal disorders Vomiting 5.1
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 5.0
Nervous system disorders Amnesia 5.0
Psychiatric disorders Anxiety 5.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 5.0
Nervous system disorders Ataxia
Nervous system disorders Ataxia 5.0
General disorders and administration site conditions Balance disorder
General disorders and administration site conditions Balance disorder 5.0
Gastrointestinal disorders Constipation 5.0
Convulsion 5.0
Respiratory, thoracic and mediastinal disorders Cough 5.0
General disorders and administration site conditions Decreased appetite 5.0
Gastrointestinal disorders Diarrhoea 5.0
Eye disorders Diplopia
Gastrointestinal disorders Dysgeusia 5.0
Gastrointestinal disorders Dyspepsia 5.0
General disorders and administration site conditions Fatigue 5.0
General disorders and administration site conditions Gait disturbance 5.0
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 5.0
Metabolism and nutrition disorders Hyponatraemia 5.0
Gastrointestinal disorders Nausea
Psychiatric disorders Nervousness 5.0
Eye disorders Nystagmus
Infections and infestations Rhinitis 5.0
Nervous system disorders Somnolence 5.0
Psychiatric disorders Tension 5.0
Nervous system disorders Tremor
Nervous system disorders Tremor 5.0
Infections and infestations Upper respiratory tract infection 5.0
Infections and infestations Urinary tract infection 5.0
Infections and infestations Viral infection 5.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 5.0
Gastrointestinal disorders Nausea 4.9
Psychiatric disorders Affect lability
Nervous system disorders Amnesia 4.0
Nervous system disorders Ataxia
Musculoskeletal and connective tissue disorders Back pain 4.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 4.0
Injury, poisoning and procedural complications Contusion 4.0
Nervous system disorders Coordination abnormal 4.0
Skin and subcutaneous tissue disorders Dermatitis 4.0
Eye disorders Diplopia
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 4.0
Respiratory, thoracic and mediastinal disorders Epistaxis 4.0
Injury, poisoning and procedural complications Fall 4.0
Infections and infestations Infection 4.0
Nervous system disorders Insomnia 4.0
Social circumstances Mental disability 4.0
Psychiatric disorders Mood swings
Psychiatric disorders Nervousness 4.0
Skin and subcutaneous tissue disorders Rash 4.0
Infections and infestations Rhinitis
Infections and infestations Rhinitis 4.0
Infections and infestations Sinusitis 4.0
Psychiatric disorders Tension 4.0
Nervous system disorders Thinking abnormal 4.0
Nervous system disorders Tremor
Nervous system disorders Tremor 4.0
Eye disorders Vision blurred 4.0
Eye disorders Visual impairment
Eye disorders Visual impairment 4.0
Nervous system disorders Somnolence 3.8
Convulsion 3.7
Gastrointestinal disorders Nausea 3.7
Eye disorders Diplopia 3.2
Gastrointestinal disorders Abdominal pain 3.0
Gastrointestinal disorders Abdominal pain upper 3.0
Psychiatric disorders Affect lability 3.0
General disorders and administration site conditions Asthenia 3.0
Nervous system disorders Ataxia 3.0
Investigations Body temperature increased 3.0
Infections and infestations Bronchitis 3.0
Nervous system disorders Cerebellar syndrome 3.0
Nervous system disorders Coordination abnormal 3.0
General disorders and administration site conditions Decreased appetite 3.0
Gastrointestinal disorders Dry mouth 3.0
Gastrointestinal disorders Dyspepsia 3.0
General disorders and administration site conditions Fatigue 3.0
General disorders and administration site conditions Gait disturbance
General disorders and administration site conditions Gait disturbance 3.0
Gastrointestinal disorders Gastritis 3.0
Gastrointestinal disorders Gastrointestinal pain 3.0
General disorders and administration site conditions Hyperhidrosis 3.0
Nervous system disorders Hypoaesthesia 3.0
Metabolism and nutrition disorders Hyponatraemia 3.0
Nervous system disorders Insomnia 3.0
Psychiatric disorders Mood swings 3.0
Infections and infestations Nasopharyngitis 3.0
Eye disorders Nystagmus 3.0
Gastrointestinal disorders Pharyngitis 3.0
Infections and infestations Sinusitis 3.0
Nervous system disorders Speech disorder 3.0
Nervous system disorders Tremor 3.0
Ear and labyrinth disorders Vertigo 3.0
Eye disorders Vision blurred
Eye disorders Visual impairment 3.0
Nervous system disorders Headache 2.9
Nervous system disorders Somnolence 2.4
General disorders and administration site conditions Asthenia 2.1
General disorders and administration site conditions Fatigue 2.1
Eye disorders Visual impairment 2.1
Eye disorders Accommodation disorder 2.0
Skin and subcutaneous tissue disorders Acne 2.0
Psychiatric disorders Affect lability 2.0
Nervous system disorders Agitation 2.0
Nervous system disorders Amnesia
Nervous system disorders Amnesia 2.0
General disorders and administration site conditions Asthenia 2.0
Musculoskeletal and connective tissue disorders Back pain
Musculoskeletal and connective tissue disorders Back pain 2.0
Nervous system disorders Cerebellar syndrome 2.0
Cardiac disorders Chest pain 2.0
Nervous system disorders Confusional state 2.0
Gastrointestinal disorders Constipation 2.0
Injury, poisoning and procedural complications Contusion
Convulsion 2.0
Nervous system disorders Coordination abnormal
Nervous system disorders Coordination abnormal 2.0
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 2.0
Nervous system disorders Disturbance in attention 2.0
General disorders and administration site conditions Drug intolerance 2.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 2.0
Infections and infestations Ear infection 2.0
Ear and labyrinth disorders Ear pain 2.0
Investigations Electroencephalogram abnormal 2.0
General disorders and administration site conditions Feeling abnormal 2.0
Metabolism and nutrition disorders Fluid retention 2.0
Gastrointestinal disorders Gastritis
Gastrointestinal disorders Gastritis 2.0
General disorders and administration site conditions Generalised oedema 2.0
General disorders and administration site conditions Hot flush 2.0
Immune system disorders Hypersensitivity 2.0
Metabolism and nutrition disorders Hyponatraemia 2.0
Vascular disorders Hypotension 2.0
Infections and infestations Infection 2.0
Nervous system disorders Insomnia 2.0
Injury, poisoning and procedural complications Ligament sprain 2.0
Blood and lymphatic system disorders Lymphadenopathy 2.0
Reproductive system and breast disorders Menopausal symptoms 2.0
Social circumstances Mental disability 2.0
Psychiatric disorders Mood swings 2.0
Musculoskeletal and connective tissue disorders Muscle contractions involuntary 2.0
Nervous system disorders Muscular weakness 2.0
Psychiatric disorders Nervousness
Psychiatric disorders Nervousness 2.0
Eye disorders Nystagmus 2.0
Cardiac disorders Oedema peripheral 2.0
Infections and infestations Pneumonia 2.0
Renal and urinary disorders Pollakiuria 2.0
Blood and lymphatic system disorders Purpura 2.0
Skin and subcutaneous tissue disorders Rash
Gastrointestinal disorders Rectal haemorrhage 2.0
Infections and infestations Rhinitis 2.0
Infections and infestations Sinusitis
Infections and infestations Sinusitis 2.0
Nervous system disorders Speech disorder 2.0
Psychiatric disorders Tension
Psychiatric disorders Tension 2.0
Nervous system disorders Thinking abnormal 2.0
General disorders and administration site conditions Thirst 2.0
Gastrointestinal disorders Toothache 2.0
Nervous system disorders Tremor
Infections and infestations Vaginal infection 2.0
Vaginal inflammation 2.0
Blood and lymphatic system disorders Vascular purpura 2.0
Ear and labyrinth disorders Vertigo
Ear and labyrinth disorders Vertigo 2.0
Eye disorders Visual impairment 2.0
Gastrointestinal disorders Vomiting 2.0
Investigations Weight increased 2.0
Nervous system disorders Ataxia 1.8
Nervous system disorders Tremor 1.8
Skin and subcutaneous tissue disorders Dermatitis 1.7
Cardiac disorders Dizziness 1.7
General disorders and administration site conditions Gait disturbance 1.7
Gastrointestinal disorders Nausea 1.7
Skin and subcutaneous tissue disorders Rash 1.7
Nervous system disorders Tremor 1.6
Skin and subcutaneous tissue disorders Dermatitis 1.4
Nervous system disorders Headache 1.4
Skin and subcutaneous tissue disorders Rash 1.4
Eye disorders Diplopia 1.3
Cardiac disorders Dizziness 1.3
Skin and subcutaneous tissue disorders Rash maculo-papular 1.3
Nervous system disorders Ataxia 1.2
Nervous system disorders Status epilepticus 1.2
General disorders and administration site conditions Asthenia 1.1
General disorders and administration site conditions Fatigue 1.1
Eye disorders Nystagmus 1.1
Gastrointestinal disorders Abdominal pain upper
Skin and subcutaneous tissue disorders Acne 1.0
Nervous system disorders Agitation
Nervous system disorders Agitation 1.0
Nervous system disorders Amnesia 1.0
General disorders and administration site conditions Asthenia
Nervous system disorders Ataxia
Nervous system disorders Ataxia 1.0
Nervous system disorders Cerebellar syndrome 1.0
Nervous system disorders Confusional state
Nervous system disorders Confusional state 1.0
Gastrointestinal disorders Constipation
Convulsion
Nervous system disorders Coordination abnormal
Nervous system disorders Coordination abnormal 1.0
Eye disorders Diplopia
Eye disorders Diplopia 1.0
Nervous system disorders Disturbance in attention
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 1.0
Ear and labyrinth disorders Ear pain 1.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling abnormal
General disorders and administration site conditions Feeling abnormal 1.0
Metabolism and nutrition disorders Fluid retention 1.0
General disorders and administration site conditions Gait disturbance
Gastrointestinal disorders Gastritis
Gastrointestinal disorders Gastritis 1.0
General disorders and administration site conditions Generalised oedema 1.0
General disorders and administration site conditions Hot flush 1.0
Nervous system disorders Hypoaesthesia 1.0
Metabolism and nutrition disorders Hyponatraemia
Metabolism and nutrition disorders Hyponatraemia 1.0
Vascular disorders Hypotension 1.0
Nervous system disorders Insomnia
Injury, poisoning and procedural complications Ligament sprain
Reproductive system and breast disorders Menopausal symptoms 1.0
Social circumstances Mental disability
Musculoskeletal and connective tissue disorders Muscle contractions involuntary
Nervous system disorders Muscular weakness 1.0
Psychiatric disorders Nervousness
Eye disorders Nystagmus
Cardiac disorders Oedema peripheral
Cardiac disorders Oedema peripheral 1.0
Infections and infestations Pneumonia
Renal and urinary disorders Pollakiuria 1.0
Nervous system disorders Speech disorder
Nervous system disorders Speech disorder 1.0
Psychiatric disorders Tension
Gastrointestinal disorders Toothache 1.0
Nervous system disorders Tremor 1.0
Infections and infestations Urinary tract infection 1.0
Eye disorders Vision blurred 1.0
Eye disorders Visual impairment
Eye disorders Visual impairment 1.0
Investigations Weight increased
Investigations Weight increased 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
22.88
General disorders and administration site conditions
12.06
Psychiatric disorders
11.89
Injury, poisoning and procedural complications
8.88
Gastrointestinal disorders
6.06
Skin and subcutaneous tissue disorders
4.63
Musculoskeletal and connective tissue disorders
3.99
Vascular disorders
3.98
Cardiac disorders
3.62
Respiratory, thoracic and mediastinal disorders
3.12
Investigations
2.99
Immune system disorders
2.32
Metabolism and nutrition disorders
2.29
Eye disorders
2.2
Pregnancy, puerperium and perinatal conditions
2.07

Cross References

Resources Reference
CAS NUMBER 28721-07-5
ChEBI 7824
ChEMBL CHEMBL1068
DrugBank DB00776
DrugCentral 2017
EPA CompTox DTXSID0045703
FDA SRS VZI5B1W380
Human Metabolome Database HMDB0014914
Guide to Pharmacology 7254
KEGG C07492
PharmGKB PA450732
PubChem 34312
SureChEMBL SCHEMBL35129
ZINC ZINC000000004724
CONTENTS