Aripiprazole

Aripiprazole
Clinical data
Pronunciation	/ˌærɪˈpɪprəzoʊl/; AIR-ih-PIP-rə-zohl; Abilify /əˈbɪlɪfaɪ/; ə-BIL-if-eye
Trade names	Abilify, others
Other names	OPC-14597; OPC14597; OPC-31; OPC31; RDC-3317
AHFS/Drugs.com	Monograph
MedlinePlus	a603012
License data	US DailyMed: Aripiprazole;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, intramuscular
Drug class	Atypical antipsychotic
ATC code	N05AX12 (WHO) ;
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
Bioavailability	87%
Protein binding	>99%
Metabolism	Liver (mostly via CYP3A4 and 2D6)
Metabolites	Dehydroaripiprazole
Elimination half-life	75 hours (active metabolite is 94 hours)
Excretion	Kidney (27%; <1% unchanged); feces (60%; 18% unchanged)
Identifiers
	IUPAC name 7-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy}-3,4-dihydroquinolin-2(1H)-one;
CAS Number	129722-12-9 ;
PubChem CID	60795;
IUPHAR/BPS	34;
DrugBank	DB01238 ;
ChemSpider	54790 ;
UNII	82VFR53I78;
KEGG	D01164 ;
ChEBI	CHEBI:31236 ;
ChEMBL	ChEMBL1112 ;
CompTox Dashboard (EPA)	DTXSID3046083 ;
ECHA InfoCard	100.112.532
Chemical and physical data
Formula	C23H27Cl2N3O2
Molar mass	448.39 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	138 to 150 °C (280 to 302 °F)
	SMILES Clc4cccc(N3CCN(CCCCOc2ccc1c(NC(=O)CC1)c2)CC3)c4Cl;
	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) ; Key:CEUORZQYGODEFX-UHFFFAOYSA-N ;
	(verify)

Aripiprazole, sold under the brand name Abilify, among others, is a unique atypical antipsychotic primarily used in the treatment of schizophrenia, mania in bipolar disorder, and irritability associated with autism spectrum disorder; 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.