ARIPIPRAZOLE

Search structure
Trade Names:
Synonyms:
Status: Approved (2002)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N05AX12
UNII: 82VFR53I78

Structure
InChI Key CEUORZQYGODEFX-UHFFFAOYSA-N
Smile O=C1CCc2ccc(OCCCCN3CCN(c4cccc(Cl)c4Cl)CC3)cc2N1
InChI
InChI=1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29)

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H27Cl2N3O2
Molecular Weight 448.39
AlogP 4.86
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 44.81
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 30.0

Pharmacology

Action Mechanism of Action Reference
PARTIAL AGONIST Dopamine D2 receptor partial agonist DailyMed
Primary Target
D2 receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel 5HT3 receptor
- - - 1000 -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 631-3860 - 598-1020 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 170-170 - 9-100 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
1-1100 8-32 - 0-5 96
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 420-420 - 25-100 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
24-285 1380-1380 - 1-63 0
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- - - 32-1080 21
Transporter Electrochemical transporter
- - - 32-1080 21
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 780 - - 99

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Depressive Disorder 4 D003866 FDA
Depressive Disorder 4 D003866 ClinicalTrials
Depressive Disorder, Major 4 D003865 ClinicalTrials
Psychotic Disorders 4 D011618 ClinicalTrials
Bipolar Disorder 4 D001714 ClinicalTrials
Depression, Postpartum 3 D019052 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Tourette Syndrome 3 D005879 ClinicalTrials
Stress Disorders, Post-Traumatic 3 D013313 ClinicalTrials
Anorexia Nervosa 3 D000856 ClinicalTrials
Child Development Disorders, Pervasive 3 D002659 ClinicalTrials
Alcoholism 3 D000437 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Child Development Disorders, Pervasive 3 D002659 ClinicalTrials
Attention Deficit Disorder with Hyperactivity 2 D001289 ClinicalTrials
Asperger Syndrome 2 D020817 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Obsessive-Compulsive Disorder 2 D009771 ClinicalTrials
Fragile X Syndrome 2 D005600 ClinicalTrials
Amphetamine-Related Disorders 1 D019969 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 32.0
Nervous system disorders Headache 31.0
Nervous system disorders Headache 30.0
Nervous system disorders Headache 27.0
Nervous system disorders Headache
Nervous system disorders Agitation 25.0
Nervous system disorders Akathisia 25.0
Psychiatric disorders Anxiety 25.0
Nervous system disorders Headache
Nervous system disorders Headache 25.0
Nervous system disorders Agitation
Nervous system disorders Agitation 24.0
Psychiatric disorders Anxiety
Nervous system disorders Insomnia 24.0
Nervous system disorders Headache
Nervous system disorders Somnolence 23.0
Psychiatric disorders Anxiety 20.0
Nervous system disorders Extrapyramidal disorder 20.0
Nervous system disorders Insomnia 20.0
Psychiatric disorders Mental disorder 20.0
Nervous system disorders Agitation 19.0
Nervous system disorders Akathisia 19.0
Nervous system disorders Insomnia
Nervous system disorders Insomnia 19.0
Nervous system disorders Extrapyramidal disorder 18.4
Nervous system disorders Insomnia 18.0
Nervous system disorders Agitation
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 17.0
General disorders and administration site conditions Asthenia 17.0
Nervous system disorders Extrapyramidal disorder 17.0
General disorders and administration site conditions Fatigue 17.0
Psychiatric disorders Mental disorder 17.0
Nervous system disorders Akathisia 16.0
Gastrointestinal disorders Nausea 16.0
Nervous system disorders Somnolence 16.0
Nervous system disorders Akathisia 15.0
Gastrointestinal disorders Dyspepsia 15.0
Nervous system disorders Insomnia
Nervous system disorders Insomnia 15.0
Gastrointestinal disorders Nausea 15.0
Nervous system disorders Extrapyramidal disorder 14.0
Nervous system disorders Insomnia 14.0
Gastrointestinal disorders Vomiting 14.0
Nervous system disorders Akathisia 13.0
Psychiatric disorders Anxiety
Gastrointestinal disorders Constipation 13.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 13.0
Nervous system disorders Headache 13.0
Nervous system disorders Insomnia
Nervous system disorders Agitation 12.0
Nervous system disorders Akathisia 12.0
Nervous system disorders Headache
Nervous system disorders Headache 12.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 12.0
Nervous system disorders Somnolence 12.0
Gastrointestinal disorders Vomiting 12.0
General disorders and administration site conditions Asthenia 11.8
General disorders and administration site conditions Fatigue 11.8
General disorders and administration site conditions Asthenia 11.0
Gastrointestinal disorders Constipation 11.0
Cardiac disorders Dizziness 11.0
General disorders and administration site conditions Fatigue 11.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 11.0
Nervous system disorders Somnolence 11.0
Gastrointestinal disorders Vomiting 11.0
Nervous system disorders Akathisia 10.0
General disorders and administration site conditions Asthenia 10.0
Gastrointestinal disorders Constipation 10.0
Cardiac disorders Dizziness 10.0
Gastrointestinal disorders Dyspepsia 10.0
General disorders and administration site conditions Fatigue 10.0
Nervous system disorders Headache 10.0
Gastrointestinal disorders Nausea 10.0
Nervous system disorders Somnolence 10.0
Nervous system disorders Tremor 10.0
Investigations Body temperature increased 9.0
Nervous system disorders Drooling 9.0
Gastrointestinal disorders Dyspepsia 9.0
Gastrointestinal disorders Nausea 9.0
Nervous system disorders Tremor 9.0
Gastrointestinal disorders Vomiting 9.0
Investigations Weight increased 9.0
Nervous system disorders Akathisia 8.0
General disorders and administration site conditions Asthenia 8.0
Gastrointestinal disorders Constipation
Cardiac disorders Dizziness
Cardiac disorders Dizziness 8.0
Gastrointestinal disorders Dyspepsia 8.0
General disorders and administration site conditions Fatigue 8.0
Nervous system disorders Insomnia 8.0
Gastrointestinal disorders Nausea 8.0
Nervous system disorders Somnolence
Nervous system disorders Somnolence 8.0
Eye disorders Vision blurred 8.0
Nervous system disorders Akathisia 7.9
Nervous system disorders Akathisia
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 7.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 7.0
General disorders and administration site conditions Decreased appetite 7.0
Cardiac disorders Dizziness
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 7.0
General disorders and administration site conditions Fatigue 7.0
Nervous system disorders Headache
Nervous system disorders Headache 7.0
General disorders and administration site conditions Increased appetite 7.0
Nervous system disorders Somnolence 7.0
Nervous system disorders Tremor 7.0
Gastrointestinal disorders Vomiting
Nervous system disorders Agitation 6.0
Nervous system disorders Akathisia 6.0
General disorders and administration site conditions Asthenia 6.0
Gastrointestinal disorders Constipation
Skin and subcutaneous tissue disorders Dermatitis 6.0
Nervous system disorders Extrapyramidal disorder 6.0
General disorders and administration site conditions Fatigue 6.0
Injury, poisoning and procedural complications Injury 6.0
Infections and infestations Nasopharyngitis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Gastrointestinal disorders Salivary hypersecretion 6.0
Nervous system disorders Somnolence 6.0
Nervous system disorders Tremor
Nervous system disorders Tremor 6.0
Infections and infestations Upper respiratory tract infection 6.0
Eye disorders Vision blurred 6.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 6.0
Nervous system disorders Insomnia 5.8
General disorders and administration site conditions Injection site pain 5.1
Nervous system disorders Agitation 5.0
Nervous system disorders Akathisia
Nervous system disorders Akathisia 5.0
Musculoskeletal and connective tissue disorders Arthralgia 5.0
General disorders and administration site conditions Asthenia
Investigations Body temperature increased 5.0
Gastrointestinal disorders Constipation 5.0
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea 5.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 5.0
Gastrointestinal disorders Dry mouth 5.0
Nervous system disorders Extrapyramidal disorder 5.0
Injury, poisoning and procedural complications Injury 5.0
General disorders and administration site conditions Lethargy 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Rash
Nervous system disorders Somnolence 5.0
Nervous system disorders Tremor 5.0
Nervous system disorders Akathisia
Nervous system disorders Akathisia 4.0
Psychiatric disorders Anxiety 4.0
Musculoskeletal and connective tissue disorders Arthralgia 4.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Decreased appetite 4.0
Cardiac disorders Dizziness 4.0
Nervous system disorders Drooling 4.0
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 4.0
Nervous system disorders Extrapyramidal disorder
Nervous system disorders Extrapyramidal disorder 4.0
General disorders and administration site conditions Fatigue
Injury, poisoning and procedural complications Injury
Nervous system disorders Insomnia
Nervous system disorders Insomnia 4.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.0
Musculoskeletal and connective tissue disorders Musculoskeletal stiffness 4.0
Musculoskeletal and connective tissue disorders Myalgia 4.0
Gastrointestinal disorders Nausea
Musculoskeletal and connective tissue disorders Pain in extremity 4.0
Gastrointestinal disorders Pharyngitis 4.0
Infections and infestations Rhinitis 4.0
Gastrointestinal disorders Salivary hypersecretion 4.0
Nervous system disorders Somnolence
Nervous system disorders Somnolence 4.0
Gastrointestinal disorders Toothache 4.0
Nervous system disorders Tremor
Nervous system disorders Tremor 4.0
Infections and infestations Upper respiratory tract infection
Gastrointestinal disorders Vomiting 4.0
Gastrointestinal disorders Abdominal discomfort 3.0
Gastrointestinal disorders Abdominal pain upper 3.0
Nervous system disorders Agitation
Nervous system disorders Agitation 3.0
Nervous system disorders Akathisia
Musculoskeletal and connective tissue disorders Arthralgia
General disorders and administration site conditions Asthenia
Investigations Body temperature increased 3.0
Gastrointestinal disorders Constipation 3.0
Respiratory, thoracic and mediastinal disorders Cough 3.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 3.0
Nervous system disorders Disturbance in attention 3.0
Cardiac disorders Dizziness 3.0
Nervous system disorders Extrapyramidal disorder
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling jittery 3.0
General disorders and administration site conditions Increased appetite
General disorders and administration site conditions Increased appetite 3.0
Injury, poisoning and procedural complications Injury
Respiratory, thoracic and mediastinal disorders Laryngeal pain 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal stiffness
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 3.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 3.0
Infections and infestations Nasopharyngitis
Infections and infestations Nasopharyngitis 3.0
Gastrointestinal disorders Nausea
Psychiatric disorders Nervousness 3.0
General disorders and administration site conditions Pain 3.0
Gastrointestinal disorders Pharyngitis
Gastrointestinal disorders Pharyngitis 3.0
Infections and infestations Rhinitis
Infections and infestations Rhinitis 3.0
Gastrointestinal disorders Salivary hypersecretion 3.0
Nervous system disorders Somnolence
Gastrointestinal disorders Toothache
Gastrointestinal disorders Toothache 3.0
Nervous system disorders Tremor
Nervous system disorders Tremor 3.0
Eye disorders Vision blurred 3.0
Gastrointestinal disorders Vomiting 3.0
Investigations Weight increased 3.0
Gastrointestinal disorders Abdominal discomfort
Gastrointestinal disorders Abdominal discomfort 2.0
Gastrointestinal disorders Abdominal pain upper
Nervous system disorders Agitation
Nervous system disorders Agitation 2.0
Nervous system disorders Akathisia
Nervous system disorders Akathisia 2.0
Vascular disorders Angiopathy 2.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 2.0
Gastrointestinal disorders Constipation
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 2.0
General disorders and administration site conditions Decreased appetite
Skin and subcutaneous tissue disorders Dermatitis 2.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Dry mouth 2.0
Reproductive system and breast disorders Dysmenorrhoea 2.0
Nervous system disorders Extrapyramidal disorder
Nervous system disorders Extrapyramidal disorder 2.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 2.0
Vascular disorders Hypertension 2.0
General disorders and administration site conditions Increased appetite
Nervous system disorders Insomnia
Respiratory, thoracic and mediastinal disorders Laryngeal pain
General disorders and administration site conditions Lethargy 2.0
Musculoskeletal and connective tissue disorders Muscle spasms 2.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.0
Infections and infestations Nasopharyngitis
Infections and infestations Nasopharyngitis 2.0
Cardiac disorders Oedema peripheral 2.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 2.0
Musculoskeletal and connective tissue disorders Pain in extremity
Musculoskeletal and connective tissue disorders Pain in extremity 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 2.0
Gastrointestinal disorders Salivary hypersecretion
Gastrointestinal disorders Salivary hypersecretion 2.0
Cardiac disorders Tachycardia 2.0
Nervous system disorders Tremor
Nervous system disorders Tremor 2.0
Investigations Weight increased
Investigations Weight increased 2.0
Gastrointestinal disorders Abdominal discomfort
Gastrointestinal disorders Abdominal discomfort 1.0
Nervous system disorders Agitation
Nervous system disorders Agitation 1.0
Nervous system disorders Akathisia
Vascular disorders Angiopathy
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 1.0
Musculoskeletal and connective tissue disorders Arthralgia 1.0
General disorders and administration site conditions Asthenia
Investigations Body temperature increased
Skin and subcutaneous tissue disorders Dermatitis
Nervous system disorders Disturbance in attention
Nervous system disorders Disturbance in attention 1.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 1.0
Nervous system disorders Dyskinesia 1.0
Reproductive system and breast disorders Dysmenorrhoea
Gastrointestinal disorders Dyspepsia 1.0
Nervous system disorders Extrapyramidal disorder
Nervous system disorders Extrapyramidal disorder 1.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Feeling jittery
General disorders and administration site conditions Feeling jittery 1.0
Nervous system disorders Hypersomnia 1.0
Vascular disorders Hypertension
General disorders and administration site conditions Irritability 1.0
Musculoskeletal and connective tissue disorders Muscle spasms
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal stiffness 1.0
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 1.0
Infections and infestations Nasopharyngitis
Psychiatric disorders Nervousness
Psychiatric disorders Nervousness 1.0
Cardiac disorders Oedema peripheral
Cardiac disorders Oedema peripheral 1.0
Nervous system disorders Orthostatic hypotension 1.0
Skin and subcutaneous tissue disorders Rash
Respiratory, thoracic and mediastinal disorders Rhinorrhoea
Gastrointestinal disorders Salivary hypersecretion
Gastrointestinal disorders Salivary hypersecretion 1.0
Cardiac disorders Tachycardia
General disorders and administration site conditions Thirst 1.0
Nervous system disorders Tremor
Eye disorders Vision blurred
Eye disorders Vision blurred 1.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 1.0
Investigations Weight increased

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Psychiatric disorders
32.29
Injury, poisoning and procedural complications
10.63
Nervous system disorders
9.95
General disorders and administration site conditions
8.59
Social circumstances
8.04
Investigations
4.13
Metabolism and nutrition disorders
3.02
Gastrointestinal disorders
2.67
Musculoskeletal and connective tissue disorders
2.58
Pregnancy, puerperium and perinatal conditions
2.15
Skin and subcutaneous tissue disorders
2.04
Respiratory, thoracic and mediastinal disorders
2.03
Vascular disorders
2.03

Cross References

Resources Reference
CAS NUMBER 129722-12-9
ChEBI 31236
ChEMBL CHEMBL1112
DrugBank DB01238
DrugCentral 242
EPA CompTox DTXSID3046083
FDA SRS 82VFR53I78
Human Metabolome Database HMDB0005042
Guide to Pharmacology 34
KEGG C12564
PDB 9SC
PharmGKB PA10026
PubChem 60795
SureChEMBL SCHEMBL8255
ZINC ZINC000001851149
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