General
Preferred name
ARIPIPRAZOLE
Synonyms
Aripiprazole (D8) ()
OPC-14597?D8 ()
OPC-14597 ()
Aripiprazole (Abilify) ()
Abilify ()
NSC-759266 ()
Abilify mycite kit ()
Aripiprex ()
Abilify mycite ()
OPC-31 ()
Abilify Maintena ()
Abilify maintena kit ()
Aripiprazole-d8 ()
Aripiprazole (CRM) ()
P&D ID
PD000697
CAS
129722-12-9
24-29-3
1026778-41-5
1089115-04-7
Tags
drug
natural product
biased GPCR ligand
available
Approved by
PMDA
EMA
FDA
First approval
2002
Drug Status
investigational
approved
Drug indication
Bipolar disorder
Schizophrenia
Major depressive disorder
Antischizophrenic
Erythropoietic porphyrias
Antipsychotic
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Aripiprazole is an typical antipsychotic.
ROE 25% of a given dose will be eliminated in urine and 55% in the feces[Label,A177910]. <1% of a dose is eliminated in the urine as unmetabolized aripiprazole and approximately 18% of a dose will be eliminated in the feces unmetabolized[Label,A177910].
PHARMACODYNAMICS Aripiprazole has high affinity for serotonin type 2 (5HT2), dopamine type 2 (D2), alpha1 and 2 adrenergic, and H1 histaminergic receptors[Label,A4393]. It also acts on a number of other receptors with lower affinity[Label,A4393]. The exact method by which aripiprazole's action on these receptors translates to a clinically relevant effect is not yet known[Label].
MOA The antipsychotic action of aripiprazole is likely due to the agonism of D2 and 5-HT1A receptors though the exact mechanism has not been defined[Label,A4393]. Some adverse effects may be due to action on other receptors[Label]. For example, orthostatic hypotension may be explained by antagonism of the adrenergic alpha1 receptors[Label,A4393].
INDICATION Aripiprazole is indicated for manic and mixed episodes associated with bipolar I disorder, irritability associated with autism spectrum disorder, treatment of schizophrenia, treatment of Tourette's disorder, and as an adjunctive treatment of major depressive disorder[Label]. An injectable formulation of aripiprazole is indicated for agitation associated with schizophrenia or bipolar mania[Label].
METABOLISM Metabolism of aripiprazole is predominantly hepatic, mediated mostly by cytochrome P450 (CYP)3A4 and CYP2D6[Label,A31184]. These enzymes perform dehydrogenation and hydroxylation while CYP3A4 alone performs N-dealkylation[Label,A31184]. At any given time, the active metabolite dehydro-aripiprazole is approximately 40% of the drug available in plasma[Label].
ABSORPTION Aripiprazole tablets are 87% bioavailable and reach peak plasma concentrations in 3 to 5 hours[Label]. These tablets can be taken with or without food, but a high fat meal can delay the time to max concentration by 3 hours and up to 12 hours for the active metabolite[Label].
HALF-LIFE The half life of aripiprazole is 75 hours while the half life of the active metabolite is 94 hours[Label]. For populations that are poor CYP2D6 metabolizers, the half life of aripiprazole is 146 hours and these patients should be treated with half the normal dose[Label]. Other studies have reported a half life of 61.03±19.59 hours for aripiprazole and 279±299 hours for the active metabolite[A177904].
DESCRIPTION Aripiprazole is an atypical antipsychotic. (GtoPdb)
TOXICITY Studies on the safety and effectiveness of aripiprazole in pregnancy have not been performed, though there is currently a national pregnancy registry for mothers currently taking aripiprazole in pregnancy[Label,L6145]. In other studies of antipsychotic medication in pregnancy, children are at risk of extrapyramidal or withdrawal symptoms[Label]. In animal studies of pregnancy, aripiprazole was associated with a number of malformations and fetal death at doses higher than the maximum recommended human dose[Label]. Aripiprazole should only be prescribed in pregnancy if the benefits outweigh the risks[Label]. Neonates with third trimester exposure to aripiprazole may show extrapyramidal or withdrawal symptoms of varying severity[Label]. These symptoms may resolve in hours or require extended hospital care[Label]. Aripiprazole's effect on labor and delivery has not been investigated[Label]. Aripiprazole is present in human breast milk and so patients should either stop breastfeeding or stop taking aripiprazole depending on the risk and benefit to mother and child[Label]. Pharmacokinetic properties in patients 10-17 years of age are similar to that of adults once body weight has been corrected for[Label]. No dosage adjustment is necessary in elderly patients however aripiprazole is not approved for Alzheimer's associated psychosis[Label]. Patients calssified as CYP2D6 poor metabolizers should be prescribed half the regular dose of aripiprazole[Label]. Hepatic and renal function as well as sex, race, and smoking status do not affect dosage requirements for aripiprazole[Label,A177904].
DESCRIPTION High affinity and selective 5-HT6 agonist (Tocris Bioactive Compound Library)
DESCRIPTION High affinity D2 and 5-HT1A receptor partial agonist; also 5-HT2A antagonist (Tocriscreen Plus)
Compound Sets
39
AdooQ Bioactive Compound Library
A11801
Axon Medchem Screening Library
1143
BiasDB
Aripiprazole
Cayman Chemical Bioactives
19989
40171
28487
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL1112
ChEMBL Drugs
CHEMBL1112
Concise Guide to Pharmacology 2017/18
34
Concise Guide to Pharmacology 2019/20
34
Concise Guide to Pharmacology 2021/22
34
Concise Guide to Pharmacology 2023/24
34
Drug Repurposing Hub
DrugBank
DB01238
DrugBank Approved Drugs
DB01238
DrugCentral
242
DrugCentral Approved Drugs
242
DrugMAP
DM3NUMH
DrugMAP Approved Drugs
DM3NUMH
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS101100
Guide to Pharmacology
34
JUMP-Target 1 Compound Set
60795
Ki Database
ARIPIPRAZOLE
OPC-14597
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1112
MedChem Express Bioactive Compound Library
HY-14546
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
82VFR53I78
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
aripiprazole-abilify
TargetMol Bioactive Compound Library
T1566
The Spectrum Collection
Tocris Bioactive Compound Library
5584
Tocriscreen Plus
5584
External IDs
59
Properties
(calculated by RDKit )
Molecular Weight
447.15
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
1
Rotatable Bonds
7
Ring Count
4
Aromatic Ring Count
2
cLogP
4.86
TPSA
44.81
Fraction CSP3
0.43
Chiral centers
0.0
Largest ring
6.0
QED
0.61
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
7-TM Receptors
Pathway
GPCR/G protein
Neuronal Signaling
Neuroscience
Target
5-HT Receptor
D(3) dopamine receptor
Alpha-1B adrenergic receptor
Alpha-1a adrenergic receptor
5-hydroxytryptamine receptor 2C
Serotonin 2a (5-HT2a) receptor
D(4) dopamine receptor
Alpha-2c adrenergic receptor
Dopamine D2 receptor
Serotonin 1a (5-HT1a) receptor
5-HT1A
ADRA1A, ADRA1B, ADRA2A, ADRA2B, ADRA2C, CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, DRD1, DRD2, DRD3, DRD4, DRD5, HRH1, HTR1A, HTR1B, HTR1D, HTR1E, HTR2A, HTR2C, HTR3A, HTR6, HTR7
Atypical antipsychotic
HTR3A
Dopamine Receptor
MOA
Dopamine Receptor agonist
Dopamine Receptor antagonist
serotonin receptor agonist
serotonin receptor antagonist
Agonist
Dopamine D2 Receptor Partial Agonists
5-HT1A Receptor Partial Agonists
ADRA1B gene inhibitor
HTR2A gene inhibitor
serotonin receptor agonist, serotonin receptor antagonist
Primary Target
D2 Receptors
Member status
member
Indication
depression, schizophrenia, bipolar disorder
Therapeutic Indication
Neuroleptic
Therapeutic Class
CNS & PNS
Antipsychotic Agents
Source data