Aripiprazole

Aripiprazole
Clinical data
Pronunciation/ˌærɪˈpɪprəzl/
AIR-ih-PIP-rə-zohl
Abilify /əˈbɪlɪf/
ə-BIL-if-eye
Trade namesAbilify, others
Other namesOPC-14597; OPC14597; OPC-31; OPC31; RDC-3317
AHFS/Drugs.comMonograph
MedlinePlusa603012
License data
Pregnancy
category
  • AU: C
Routes of
administration
By mouth, intramuscular
Drug classAtypical antipsychotic
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • NZ: Prescription only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability87%
Protein binding>99%
MetabolismLiver (mostly via CYP3A4 and 2D6)
MetabolitesDehydroaripiprazole
Elimination half-life75 hours (active metabolite is 94 hours)
ExcretionKidney (27%; <1% unchanged)
feces (60%; 18% unchanged)
Identifiers
  • 7-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy}-3,4-dihydroquinolin-2(1H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.112.532
Chemical and physical data
FormulaC23H27Cl2N3O2
Molar mass448.39 g·mol−1
3D model (JSmol)
  • Clc4cccc(N3CCN(CCCCOc2ccc1c(NC(=O)CC1)c2)CC3)c4Cl
  • 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) Y
  • Key:CEUORZQYGODEFX-UHFFFAOYSA-N Y
  (verify)

Aripiprazole, sold under the brand name Abilify, among others, is an atypical antipsychotic primarily used in the treatment of schizophrenia, mania in bipolar disorder, and irritability associated with autism spectrum disorder (in children and adolescents aged 6 to 17 years); other uses include as an add-on treatment for major depressive disorder, obsessive–compulsive disorder, and tic disorders. Aripiprazole is taken by mouth or via injection into a muscle.

It has generally favorable tolerability. Common side effects include restlessness, insomnia, transient weight gain, nausea, vomiting, constipation, dizziness, and mild sedation. Serious side effects may include neuroleptic malignant syndrome, tardive dyskinesia, and anaphylaxis. It is not recommended for older people with dementia-related psychosis due to an increased risk of death. In pregnancy, there is evidence of possible harm to the fetus. It is not recommended in women who are breastfeeding. It has not been very well studied in people younger than 18.

Aripiprazole is a pharmacologically unique atypical antipsychotic whose principal pharmacological action is as a functionally selective partial agonist at dopamine D₂ receptors, stabilizing dopamine activity by enhancing signaling when levels are low and reducing it when levels are high. It also acts as a partial agonist at dopamine D₃ and D₄ receptors and at serotonin 5-HT₁A and 5-HT₂C receptors. It is a third-generation antipsychotic and its introduction led to a paradigm shift in antipsychotic drug development.

Aripiprazole was discovered in 1988 by Otsuka Pharmaceutical. It received approval for medical use in the United States in 2002 and has since become available as a generic medication. In 2023, it was the 95th most commonly prescribed medication in the U.S., with more than 7 million prescriptions. It is on the World Health Organization's List of Essential Medicines.