aripiprazole   Click here for help

GtoPdb Ligand ID: 34

Synonyms: Abilify® | Aripiprex® | Aristada® (aripiprazole lauroxil) | OPC 14597 | OPC-14597
Approved drug PDB Ligand
aripiprazole is an approved drug (FDA (2002), EMA (2004))
Compound class: Synthetic organic
Comment: Aripiprazole is an atypical antipsychotic.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 44.81
Molecular weight 447.15
XLogP 4.61
No. Lipinski's rules broken 0
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Canonical SMILES O=C1CCc2c(N1)cc(cc2)OCCCCN1CCN(CC1)c1cccc(c1Cl)Cl
Isomeric SMILES O=C1CCc2c(N1)cc(cc2)OCCCCN1CCN(CC1)c1cccc(c1Cl)Cl
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)
No information available.
Summary of Clinical Use Click here for help
Atypical antipsychotic used in the treatment of schizophrenia and bipolar disorder and to control irritability in autistic patients. The first generic versions of the drug were approved by the FDA in April 2015. Aristada® contains aripiprazole lauroxil (PubChem CID 49831411) which is a second generation aripiprazole prodrug [6] that allows for extended-release and long-acting effects. It is an injectable formulation that is approved for the treatment of schizophrenia [1,5].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Aripiprazole's antipsychotic activity is likely due to a combination of antagonism at dopamine D2 receptors in the mesolimbic pathway and serotonin 5-HT2A receptors in the frontal cortex.