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Details

Stereochemistry ACHIRAL
Molecular Formula C23H27Cl2N3O2
Molecular Weight 448.385
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARIPIPRAZOLE

SMILES

ClC1=CC=CC(N2CCN(CCCCOC3=CC=C4CCC(=O)NC4=C3)CC2)=C1Cl

InChI

InChIKey=CEUORZQYGODEFX-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C23H27Cl2N3O2
Molecular Weight 448.385
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
0.34 nM [Ki]
8.7 nM [Ki]
5.6 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ABILIFY
Primary
ABILIFY
Primary
ABILIFY
Primary
ABILIFY
Primary
ABILIFY
Primary
ABILIFY

Cmax

ValueDoseCo-administeredAnalytePopulation
163 ng/mL
10 mg 1 times / day multiple, oral
ARIPIPRAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2947 ng × h/mL
10 mg 1 times / day multiple, oral
ARIPIPRAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
52.9 h
10 mg 1 times / day multiple, oral
ARIPIPRAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
10 mg 1 times / day multiple, oral
ARIPIPRAZOLE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Record UNII
82VFR53I78
Record Status Validated (UNII)
Record Version