ARIPIPRAZOLE MONOHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H27Cl2N3O2.H2O
Molecular Weight	466.401
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.ClC1=C(Cl)C(=CC=C1)N2CCN(CCCCOC3=CC4=C(CCC(=O)N4)C=C3)CC2

InChI

InChIKey=UXQBDXJXIVDBTF-UHFFFAOYSA-N

InChI=1S/C23H27Cl2N3O2.H2O/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);1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C23H27Cl2N3O2
Molecular Weight	448.385
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12784105/, https://www.ncbi.nlm.nih.gov/pubmed/12587943, https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0000157/

Aripiprazole is the first next-generation atypical antipsychotic. The unique actions of aripiprazole in humans are likely a combination of "functionally selective" activation of D(2) (and possibly D(3))-dopamine receptors and serotonin 5-HT(1A) receptors, coupled with inhibition of 5-HT(2A) receptors. Aripiprazole was approved by FDA (Abilify trade name) for the treatment of schizophrenia; manic and mixed episodes associated with bipolar I disorder; major depressive disorder; irritability associated with autistic disorder; Tourette’s disorder and agitation associated with schizophrenia or bipolar mania.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Partial Agonist 297	0.34 nM [Ki]
Serotonin 2a (5-HT2a) receptor 237 Target ID: CHEMBL224 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Antagonist 2849	8.7 nM [Ki]
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Partial Agonist 297	5.6 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 305 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Primary	Approved 8583	ABILIFY Approved Use ABILIFY is an atypical antipsychotic. The oral formulations are indicated for: Schizophrenia, Acute Treatment of Manic and Mixed Episodes associated with Bipolar I, Adjunctive Treatment of Major Depressive Disorder, Irritability Associated with Autistic Disorder, Treatment of Tourette’s disorder, The injection is indicated for: Agitation associated with schizophrenia or bipolar mania Launch Date 2002
Bipolar I disorder 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Primary	Approved 8583	ABILIFY Approved Use ABILIFY is an atypical antipsychotic. The oral formulations are indicated for: Schizophrenia, Acute Treatment of Manic and Mixed Episodes associated with Bipolar I, Adjunctive Treatment of Major Depressive Disorder, Irritability Associated with Autistic Disorder, Treatment of Tourette’s disorder, The injection is indicated for: Agitation associated with schizophrenia or bipolar mania Launch Date 2002
Major depressive disorder 179 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Primary	Approved 8583	ABILIFY Approved Use ABILIFY is an atypical antipsychotic. The oral formulations are indicated for: Schizophrenia, Acute Treatment of Manic and Mixed Episodes associated with Bipolar I, Adjunctive Treatment of Major Depressive Disorder, Irritability Associated with Autistic Disorder, Treatment of Tourette’s disorder, The injection is indicated for: Agitation associated with schizophrenia or bipolar mania Launch Date 2002
Autism 20 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Primary	Approved 8583	ABILIFY Approved Use ABILIFY is an atypical antipsychotic. The oral formulations are indicated for: Schizophrenia, Acute Treatment of Manic and Mixed Episodes associated with Bipolar I, Adjunctive Treatment of Major Depressive Disorder, Irritability Associated with Autistic Disorder, Treatment of Tourette’s disorder, The injection is indicated for: Agitation associated with schizophrenia or bipolar mania Launch Date 2002
Tourette's syndrome 20 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Primary	Approved 8583	ABILIFY Approved Use ABILIFY is an atypical antipsychotic. The oral formulations are indicated for: Schizophrenia, Acute Treatment of Manic and Mixed Episodes associated with Bipolar I, Adjunctive Treatment of Major Depressive Disorder, Irritability Associated with Autistic Disorder, Treatment of Tourette’s disorder, The injection is indicated for: Agitation associated with schizophrenia or bipolar mania Launch Date 2002
Agitation associated with schizophrenia or bipolar mania 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021436s038,021713s030,021729s022,021866s023lbl.pdf	Primary	Approved 8583	ABILIFY Approved Use ABILIFY is an atypical antipsychotic indicated as oral formulations for the: Treatment of schizophrenia (1.1) Adults: Efficacy was established in four 4-6 week trials and one maintenance trial in patients with schizophrenia (14.1) Adolescents (ages 13-17): Efficacy was established in one 6-week trial in patients with schizophrenia (14.1) Acute treatment of manic or mixed episodes associated with bipolar I disorder as monotherapy and as an adjunct to lithium or valproate (1.2) Adults: Efficacy was established in four 3-week monotherapy trials and one 6-week adjunctive trial in patients with manic or mixed episodes (14.2) Pediatric Patients (ages 10-17): Efficacy was established in one 4-week monotherapy trial in patients with manic or mixed episodes (14.2) Maintenance treatment of bipolar I disorder, both as monotherapy and as an adjunct to lithium or valproate (1.2) Adults: Efficacy was established in one maintenance monotherapy trial and in one maintenance adjunctive trial (14.2) Adjunctive treatment of major depressive disorder (MDD) (1.3) Adults: Efficacy was established in two 6-week trials in patients with MDD who had an inadequate response to antidepressant therapy during the current episode (14.3) Treatment of irritability associated with autistic disorder (1.4) Pediatric Patients (ages 6-17 years): Efficacy was established in two 8-week trials in patients with autistic disorder (14.4) as an injection for the: Acute treatment of agitation associated with schizophrenia or bipolar I disorder (1.5) Adults: Efficacy was established in three 24-hour trials in agitated patients with schizophrenia or manic/mixed episodes of bipolar I disorder (14.5) 1.1 Schizophrenia ABILIFY is indicated for the treatment of schizophrenia. The efficacy of ABILIFY was established in four 4-6 week trials in adults and one 6-week trial in adolescents (13 to 17 years). Maintenance efficacy was demonstrated in one trial in adults and can be extrapolated to adolescents [see CLINICAL STUDIES (14.1) Launch Date 2002

C_max

Value	Dose	Co-administered	Analyte	Population
163 ng/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/15257633	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARIPIPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2947 ng × h/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/15257633	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARIPIPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
52.9 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/15257633	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARIPIPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% REVIEW https://www.ncbi.nlm.nih.gov/pubmed/15257633	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ARIPIPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18626272	unhealthy, 10-17 years Health Status: unhealthy Age Group: 10-17 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18626272	Other AEs: Abdominal pain upper, Vomiting... Other AEs: Abdominal pain upper (17%) Vomiting (17%) Dizziness (17%) Headache (50%) Sedation (33%) Somnolence (17%) Sources: https://pubmed.ncbi.nlm.nih.gov/18626272
2 mg single, intravenous Dose: 2 mg Route: intravenous Route: single Dose: 2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18563956/	healthy, 35 years (range: 18-45 years) Health Status: healthy Age Group: 35 years (range: 18-45 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18563956/	Sources: https://pubmed.ncbi.nlm.nih.gov/18563956/
45 mg single, intramuscular Highest studied dose Dose: 45 mg Route: intramuscular Route: single Dose: 45 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18563956/	unhealthy, 39 years (range: 18-65 years) Health Status: unhealthy Age Group: 39 years (range: 18-65 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18563956/	Sources: https://pubmed.ncbi.nlm.nih.gov/18563956/
195 mg single, oral Overdose Dose: 195 mg Route: oral Route: single Dose: 195 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf	unhealthy, < 12 years Health Status: unhealthy Age Group: < 12 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf	Other AEs: Vomiting, Somnolence... Other AEs: Vomiting Somnolence Tremor Acidosis Aggression Aspartate aminotransferase increased Atrial fibrillation Coma Confusional state Convulsion Blood creatine phosphokinase increased Depressed level of consciousness Hypertension Hypokalemia Hypotension Lethargy Loss of consciousness QT prolonged Aspiration pneumonia Respiratory arrest Status epilepticus Tachycardia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf
10 mg 1 times / day steady, oral Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00102063	unhealthy, adolescent Health Status: unhealthy Age Group: adolescent Sources: https://clinicaltrials.gov/ct2/show/NCT00102063	Other AEs: Extrapyramidal disorder, Neuroleptic malignant syndrome... Other AEs: Extrapyramidal disorder (serious, 1 patient) Neuroleptic malignant syndrome (serious, 1 patient) Aggression (serious, 1 patient) Schizophrenia (serious, 1 patient) Nausea (below serious, 9 patients) Nasopharyngitis (below serious, 5 patients) Dizziness (below serious, 7 patients) Extrapyramidal disorder (below serious, 13 patients) Headache (below serious, 16 patients) Somnolence (below serious, 11 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT00102063
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00102063	unhealthy, adolescent Health Status: unhealthy Age Group: adolescent Sources: https://clinicaltrials.gov/ct2/show/NCT00102063	Other AEs: Varicella, Depression... Other AEs: Varicella (serious, 1 patient) Depression (serious, 1 patient) Schizophrenia (serious, 1 patient) Suicidal ideation (serious, 1 patient) Thrombophlebitis (serious, 1 patient) Nausea (below serious, 10 patients) Nasopharyngitis (below serious, 5 patients) Dizziness (below serious, 4 patients) Extrapyramidal disorder (below serious, 22 patients) Headache (below serious, 11 patient) Somnolence (below serious, 22 patients) Tremor (below serious, 12 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00102063
1080 mg single, oral Overdose Dose: 1080 mg Route: oral Route: single Dose: 1080 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf	Other AEs: Vomiting, Somnolence... Other AEs: Vomiting Somnolence Tremor Acidosis Aggression Aspartate aminotransferase increased Atrial fibrillation Coma Confusional state Convulsion Blood creatine phosphokinase increased Depressed level of consciousness Hypertension Hypokalemia Hypotension Lethargy Loss of consciousness QT prolonged Aspiration pneumonia Respiratory arrest Status epilepticus Tachycardia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021729lbl.pdf
15 mg 1 times / day steady, oral Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00198107	unhealthy, children Health Status: unhealthy Age Group: children Sources: https://clinicaltrials.gov/ct2/show/NCT00198107	Other AEs: Constipation, Diarrhea... Other AEs: Constipation (below serious, 8 patients) Diarrhea (below serious, 7 patients) Nausea (below serious, 2 patients) Abdominal discomfort (below serious, 7 patients) Vomiting (below serious, 15 patients) Decreased appetite (below serious, 12 patients) Increased appetite (below serious, 16 patients) Drowsiness (below serious, 5 patients) Tiredness (below serious, 21 patient) Fever (below serious, 3 patients) Weight gain (below serious, 8 patients) Muscle rigidity (below serious, 3 patients) Tremor (below serious, 3 patients) Nervousness (below serious, 3 patients) Repetitive speech (below serious, 3 patients) Restlessness (below serious, 3 patients) Feeling sad (below serious, 3 patients) Self injurious behavior (below serious, 3 patients) Enuresis (below serious, 3 patients) Dizziness (below serious, 4 patients) Nose bleed (below serious, 3 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00198107
15 mg 1 times / day steady, oral Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01338298	unhealthy Health Status: unhealthy Sex: F Sources: https://clinicaltrials.gov/ct2/show/NCT01338298	Other AEs: Abdominal pain, Bruising... Other AEs: Abdominal pain (below serious, 7 patients) Bruising (below serious, 2 patients) Constipation (below serious, 6 patients) Diarrhea (below serious, 9 patients) Dizziness (below serious, 5 patients) Dry mouth (below serious, 6 patients) Enuresis (below serious, 5 patients) Headache (below serious, 6 patients) Insomnia (below serious, 8 patients) Malaise (below serious, 7 patients) Mucosal ulceration (below serious, 4 patients) Nausea (below serious, 10 patients) Restlessness (below serious, 5 patients) Sedation (below serious, 7 patients) Tinnitus (below serious, 7 patients) Tremor (below serious, 8 patients) Vomiting (below serious, 10 patients) Weight loss (below serious, 4 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01338298
20 mg 1 times / day steady, oral Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00489866	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00489866	Other AEs: Restlessness, Decreased activity... Other AEs: Restlessness (below serious, 2 patients) Decreased activity (below serious, 1 patient) Drowsiness (below serious, 2 patients) Vertigo (below serious, 1 patient) Cold extremities (below serious, 1 patient) Blurred vision (below serious, 2 patients) Sexual disorder NOS (below serious, 2 patients) Joint stiffness (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT00489866
20 mg 1 times / day steady, oral Dose: 20 mg, 1 times / day Route: oral Route: steady Dose: 20 mg, 1 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00497055	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00497055	Other AEs: Rhabdomyolysis, Pneumonia... Other AEs: Rhabdomyolysis (serious, 1 patient) Pneumonia (serious, 1 patient) Cellulitis (serious, 1 patient) Abrasions (below serious, 3 patients) Akathisia (below serious, 12 patients) Drowsiness (below serious, 6 patients) Fatigue (below serious, 8 patients) Depressed mood (below serious, 3 patients) Hypernatremia (below serious, 4 patients) Hypocalcemia (below serious, 3 patients) ALT increased (below serious, 8 patients) Aspartate aminotransferase increased (below serious, 6 patients) Restlessness (below serious, 4 patients) Sleep disturbance (below serious, 3 patients) Infection upper respiratory (below serious, 6 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00497055
400 mg 1 times / 4 weeks steady, oral Dose: 400 mg, 1 times / 4 weeks Route: oral Route: steady Dose: 400 mg, 1 times / 4 weeks Sources: https://clinicaltrials.gov/ct2/show/NCT00705783	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00705783	Other AEs: Suicidal ideation, Gun shot wound... Other AEs: Suicidal ideation (serious, 2 patients) Gun shot wound (serious, 1 patient) Injury (serious, 1 patient) Multiple injuries (serious, 1 patient) Diabetes mellitus (serious, 1 patient) Hyperglycaemia (serious, 1 patient) Pancreatic carcinoma (serious, 1 patient) Hallucination, auditory (serious, 1 patient) Suicide attempt (serious, 1 patient) Headache (below serious, 16 patients) Insomnia (below serious, 27 patients) Tremor (below serious, 16 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00705783

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 P-gp 1741 BCRP 910	CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729 UGT 219 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0	not significant	unlikely (co-administration study) Comment: aripiprazole had no effect ont the PK of omeprazole Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0	not significant	unlikely (co-administration study) Comment: aripiprazole had no effect on the PK of warfarin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0	not significant	unlikely (co-administration study) Comment: aripiprazole had no effect on the PK of of dextromethorphan Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0	not significant	unlikely (co-administration study) Comment: aripiprazole had no effect on the PK of of dextromethorphan Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0	not significant	unlikely Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-436_Abilify_biopharmr_P1.pdf#page=43 Page: 43.0
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22847220/	yes [IC50 1.2 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22847220/	yes [IC50 3.5 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021713s004,021436s007lbl.pdf#page=5 Page: 5.0	no
P-gp 2052	substrate 4014 Sources: https://www.futuremedicine.com/doi/abs/10.2217/pgs.11.55 Page: 1.0	yes
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207202lbl.pdf#page=29 Page: 29.0	yes	yes (co-administration study) Comment: Coadministration of aripiprazole with quinidine, a potent inhibitor of CYP2D6, increased the AUC of aripiprazole by 112% but decreased the AUC of its active metabolite, dehydroaripiprazole, by 35%; PHARMACOGENOMIC STUDY: 82% increase in aripiprazole systemic exposure in CYP2D6 PM compared to EM, net increase of aripiprazole exposure is greater than 60%, total body clearance of aripiprazole in PM decreased by 40%, not adequately studied in PM patients; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207202lbl.pdf#page=29 Page: 29.0
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207202lbl.pdf#page=29 Page: 29.0	yes	yes (co-administration study) Comment: Coadministration of ketoconazole increased the AUC of aripiprazole and its active metabolite by 63% and 77%, respectively; Coadministration of carbamazepine, a potent CYP3A4 inducer, resulted in an approximate 70% decrease in Cmax and AUC values of both aripiprazole and its active metabolite, dehydro-aripiprazole; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207202lbl.pdf#page=29 Page: 29.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3472675/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31236	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31236
ChemicalBook	CB42487193	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB42487193
ChemicalBook	CB8210870	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8210870
eMolecules	901410	https://www.emolecules.com/cgi-bin/more?vid=901410
MolPort	MolPort-002-885-808	https://www.molport.com/shop/molecule-link/MolPort-002-885-808
MolPort	MolPort-046-939-776	https://www.molport.com/shop/molecule-link/MolPort-046-939-776
Selleck Chemicals	aripiprazole-abilify	http://www.selleckchem.com/products/aripiprazole-abilify.html
ZINC	ZINC000001851149	http://zinc15.docking.org/substances/ZINC000001851149

PubMed

Title	Date	PubMed
In vivo canine model comparison of cardiohemodynamic and electrophysiological effects of a new antipsychotic drug aripiprazole (OPC-14597) to haloperidol.	2001 Jun 1	11384214
Gateways to clinical trials.	2002 Dec	12616965
Psychotropic drugs and the ECG: focus on the QTc interval.	2002 May	11996627
Gateways to clinical trials.	2002 Nov	12616707
Biological perspectives. Aripiprazole: a third generation of antipsychotics begins?	2002 Oct-Dec	12629954
Similarities and differences among antipsychotics.	2003	14680420
Aripiprazole: a partial dopamine D2 receptor agonist antipsychotic.	2003 Apr	12665420
Relationship of atypical antipsychotics with development of diabetes mellitus.	2003 Dec	14632602
Efficacy and safety of aripiprazole vs. haloperidol for long-term maintenance treatment following acute relapse of schizophrenia.	2003 Dec	14609439
Aripiprazole: efficacy and tolerability profile of a novel-acting atypical antipsychotic.	2003 Feb	12698209
New product intros.	2003 Jan-Feb	12682670
Aripiprazole: a review of its pharmacology and clinical use.	2003 Jan-Feb	12587943
Antipsychotic medication and seizures: a review.	2003 Jul	12973403
Gateways to clinical trials.	2003 Jun	12851663
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.	2003 Mar	12629531
Aripiprazole and extrapyramidal symptoms.	2003 Nov	14566162
Aripiprazole in an adult with Asperger disorder.	2003 Nov	14565842
Serotonin receptors: their key role in drugs to treat schizophrenia.	2003 Oct	14642974
Mechanism of new antipsychotic medications: occupancy is not just antagonism.	2003 Oct	14557141
Aripiprazole for the prevention of relapse in stabilized patients with chronic schizophrenia: a placebo-controlled 26-week study.	2003 Sep	14628980
Aripiprazole for schizophrenia.	2004	15106256
Dose response and dose equivalence of antipsychotics.	2004 Apr	15206667
Aripiprazole (OPC-14597) fully substitutes for the 5-HT1A receptor agonist LY293284 in the drug discrimination assay in rats.	2004 Apr	14647959
Survey on schizophrenia treatment in Mexico: perception and antipsychotic prescription patterns.	2004 Apr 27	15109398
Aripiprazole possibly worsens psychosis.	2004 Jan	15101571
Gateways to clinical trials.	2004 Jan-Feb	14988742
Aripiprazole, a novel antipsychotic drug, preferentially increases dopamine release in the prefrontal cortex and hippocampus in rat brain.	2004 Jun 16	15189766
Gateways to clinical trials.	2004 Mar	15071612
International Congress of Biological Psychiatry. 8-13 February 2004, Sydney, Australia.	2004 Mar	15017455
Aripiprazole: a comprehensive review of its pharmacology, clinical efficacy, and tolerability.	2004 May	15220010

Patents

Sample Use Guides

In Vivo Use Guide

In adults with schizophrenia the recommended starting and target dose for aripiprazole (ABILIFY) is 10 or 15 mg/day. In adolescents the target dose is 10 mg/day. In adults with Bipolar I Disorder, the recommended starting dose is 15 mg given once daily as monotherapy and 10 mg to 15 mg given once daily as adjunctive therapy with lithium or valproate. In pediatric patients (10 to 17 years) with Bipolar I Disorder, the starting dose as monotherapy is 2 mg/day, with titration to 5 mg/day after 2 days, and a target dose of 10 mg/day after 2 additional days. In adults with Major Depressive Disorder, the recommended starting dose as adjunctive treatment for patients already taking an antidepressant is 2 to 5 mg/day. The recommended dosage range is 2 to 15 mg/day. In pediatric patients with Irritability Associated with Autistic Disorder, dosing should be initiated at 2 mg/day. The dose should be increased to 5 mg/day, with subsequent increases to 10 or 15 mg/day if needed. In pediatric patient with Tourette’s Disorder, the recommended dosage is 5 to 20 mg/day. In adults with Agitation Associated with Schizophrenia or Bipolar Mania, the recommended dose is 9.75 mg. The recommended dosage range is 5.25 to 15 mg.

Route of Administration: Other

In Vitro Use Guide

PC12 cells were treated with 0.001-1.0 uM aripiprazole in the presence of NGF (2.5ng/ml). Aripiprazole significantly potentiated nerve growth factor (NGF)-induced neurite outgrowth in PC12 cells, in a concentration-dependent manner.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:24:17 GMT 2025` Edited by `admin` on `Mon Mar 31 23:24:17 GMT 2025`
Record UNII	O362MEQ7VR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARIPIPRAZOLE MONOHYDRATE

Common Name

English

2(1H)-QUINOLINONE, 7-(4-(4-(2,3-DICHLOROPHENYL)-1-PIPERAZINYL)BUTOXY)-3,4-DIHYDRO-, HYDRATE (1:1)

Preferred Name

English

ABILIFY ASIMTUFII

Brand Name

English

Aripiprazole monohydrate [WHO-DD]

Common Name

English

2(1H)-QUINOLINONE, 7-(4-(4-(2,3-DICHLOROPHENYL)-1-PIPERAZINYL)BUTOXY)-3,4-DIHYDRO-, MONOHYDRATE

Systematic Name

English

ARIPIPRAZOLE HYDRATE [JAN]

Common Name

English

Code System Code Type Description

CAS

851220-85-4