Structure via PubChem · Public domain (PubChem)
aripiprazole
Sign in to saveAlso known as OPC 14597, OPC-14597, OPC 31
alt=A box of aripiprazole 15 mg tablets.|thumb|Aripiprazole 15 mg tablets 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 (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.
Key facts
- Drug.ChEMBL
- 1112
- Drug.legal_UK
- POM
- Drug.ChEBI
- 31236
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 443398218
- Drug.image
- Aripiprazole chemical structure.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Structural formula of aripiprazole
- Drug.width
- 250px
- Drug.image2
- Aripiprazole 3D ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the aripiprazole molecule
- Drug.width2
- 250px
- Drug.pronounce
- Abilify
- Drug.tradename
- Abilify, others
- Drug.MedlinePlus
- a603012
- Drug.DailyMedID
- Aripiprazole
via Wikipedia infobox
Chemical data
- Formula
- C23H27Cl2N3O2
- Molecular weight
- 448.4 g/mol
- IUPAC name
- 7-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one
- SMILES
- C1CC(=O)NC2=C1C=CC(=C2)OCCCCN3CCN(CC3)C4=C(C(=CC=C4)Cl)Cl
- InChIKey
- CEUORZQYGODEFX-UHFFFAOYSA-N
- XLogP
- 4.6
- Polar surface area
- 44.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2002
- Admin. routes
- oral, parenteral
- Indications
- attention deficit hyperactivity disorder, autism, psychosis, Tourette syndrome
via ChEMBL · EBI
Research
6,214 papers- Aripiprazole.The American journal of hospice & palliative care · 2017
- Aripiprazole in Children and Adolescents.Journal of child and adolescent psychopharmacology · 2021
- Aripiprazole for the treatment of Tourette syndrome.Expert review of neurotherapeutics · 2021
- Aripiprazole.Profiles of drug substances, excipients, and related methodology · 2013
- Aripiprazole for the treatment of delusional disorders: A systematic review.General hospital psychiatry · 2020
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- chlorine
- Mass
- 447.148032
- Has use
- medication
Show 11 more facts
- chemical formula
- C₂₃H₂₇Cl₂N₃O₂
- medical condition treated
- borderline personality disorder
- canonical SMILES
- C1CC(=O)NC2=C1C=CC(=C2)OCCCCN3CCN(CC3)C4=C(C(=CC=C4)Cl)Cl
- World Health Organisation international non-proprietary name
- aripiprazole
- Commons category
- Aripiprazole
- subject has role
- atypical antipsychotic
- physically interacts with
- Histamine receptor H1
- legal status (medicine)
- boxed warning
- stylized name
- ARIPiprazole
- defined daily dose
- 13.3
- significant drug interaction
- fosphenytoin
Sources (8)
via Wikidata · CC0
~36 min read
Encyclopedic overview
30 sectionsContents
- Medical uses
- Schizophrenia
- Bipolar disorder
- Depression
- Autism
- Tic disorders
- Obsessive–compulsive disorder
- Sleep disorders
- Available forms
- Contraindications
- Adverse effects
- Discontinuation
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Analogues
- History
- Society and culture
- Legal status
- Classification
- Brand names
- Research
- Attention deficit hyperactivity disorder
- Substance dependence
- References
- Further reading
- External links
{{Infobox drug | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 443398218 | image = Aripiprazole chemical structure.svg | image_class = skin-invert-image | alt = Structural formula of aripiprazole | width = 250px | image2 = Aripiprazole 3D ball-and-stick.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the aripiprazole molecule | width2 = 250px | caption = | pronounce = Abilify | tradename = Abilify, others | Drugs.com = | MedlinePlus = a603012 | DailyMedID = Aripiprazole | pregnancy_AU = C | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth, intramuscular | class = Atypical antipsychotic | ATC_prefix = N05 | ATC_suffix = AX12 | ATC_supplemental = | legal_AU = S4 | legal_AU_comment = | legal_BR = C1 | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = Prescription only | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =
| bioavailability = 87% | protein_bound = >99% | metabolism = Liver (mostly via CYP3A4 and 2D6) | metabolites = Dehydroaripiprazole | onset = | elimination_half-life = 75 hours (active metabolite is 94 hours) | duration_of_action = | excretion = Kidney (27%; feces (60%; 18% unchanged)
Excerpted from Wikipedia’s “aripiprazole” article, available under the CC BY-SA 4.0 licence.