Aripiprazole

Aripiprazole

Clinical data
Pronunciation	/ˌeɪrᵻˈpɪprəzoʊl/ AIR-i-PIP-rə-zohl Abilify ə-BIL-i-fy
Trade names	Abilify
AHFS/Drugs.com	Monograph
MedlinePlus	a603012
License data	EU EMA: Aripiprex Abilify, Aripiprex US FDA: Aripiprazole
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	By mouth (tablets, dissolving tablets, solution); IM (including a depot)
ATC code	N05AX12 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	87%
Protein binding	>99%
Metabolism	Liver (mostly via CYP3A4 and 2D6)
Biological half-life	75 hours (active metabolite is 94 hours)
Excretion	Renal (27%; <1% unchanged), Faecal (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 Y
PubChem (CID)	60795
IUPHAR/BPS	34
DrugBank	DB01238 N
ChemSpider	54790 Y
UNII	82VFR53I78 Y
KEGG	D01164 Y
ChEBI	CHEBI:31236 Y
ChEMBL	CHEMBL1112 Y
ECHA InfoCard	100.112.532
Chemical and physical data
Formula	C23H27Cl2N3O2
Molar mass	448.385 g/mol
3D model (Jmol)	Interactive image
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) Y Key:CEUORZQYGODEFX-UHFFFAOYSA-N Y
NY (what is this?)

Aripiprazole, sold under the brand name Abilify among others, is an atypical antipsychotic. It is recommended and primarily used in the treatment of schizophrenia and bipolar disorder. Other uses include as an add-on treatment in major depressive disorder, tic disorders, and irritability associated with autism. According to a Cochrane review, evidence for the oral form in schizophrenia is not sufficient to determine effects on general functioning. Additionally, because many people dropped out of the medication trials before they were completed, the overall strength of the conclusions is low.

Side effects include neuroleptic malignant syndrome, a movement disorder known as tardive dyskinesia, and high blood sugar in those with diabetes. In the elderly there is an increased risk of death. It is thus not recommended for use in those with psychosis due to dementia. It is pregnancy category C in the United States and category C in Australia, meaning there is possible evidence of harm to the fetus. It is not recommended for women who are breastfeeding. It is unclear whether it is safe or effective in people less than 18 years old.

It is a partial dopamine agonist. Aripiprazole was developed by Otsuka in Japan. In the United States, Otsuka America markets it jointly with Bristol-Myers Squibb. From April 2013 to March 2014, sales of Abilify amounted to almost $6.9 billion.