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)
1. Aggarwal A, Gopalakrishna G, Lauriello J. (2016)
Aripiprazole Lauroxil Long-Acting Injectable: The Latest Addition to Second-Generation Long-Acting Agents.
Clin Schizophr Relat Psychoses, 10 (1): 58-63. [PMID:27074333]
2. Allen JA, Yost JM, Setola V, Chen X, Sassano MF, Chen M, Peterson S, Yadav PN, Huang XP, Feng B et al.. (2011)
Discovery of β-arrestin-biased dopamine D2 ligands for probing signal transduction pathways essential for antipsychotic efficacy.
Proc Natl Acad Sci USA, 108 (45): 18488-93. [PMID:22025698]
3. Kroeze WK, Hufeisen SJ, Popadak BA, Renock SM, Steinberg S, Ernsberger P, Jayathilake K, Meltzer HY, Roth BL. (2003)
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
Neuropsychopharmacology, 28 (3): 519-26. [PMID:12629531]
4. Lawler CP, Prioleau C, Lewis MM, Mak C, Jiang D, Schetz JA, Gonzalez AM, Sibley DR, Mailman RB. (1999)
Interactions of the novel antipsychotic aripiprazole (OPC-14597) with dopamine and serotonin receptor subtypes.
Neuropsychopharmacology, 20 (6): 612-27. [PMID:10327430]
5. Raedler LA. (2016)
Aripiprazole Lauroxil (Aristada): Long-Acting Atypical Antipsychotic Injection Approved for the Treatment of Patients with Schizophrenia.
Am Health Drug Benefits, 9 (Spec Feature): 40-3. [PMID:27668044]
6. Rohde M, M Rk N, Håkansson AE, Jensen KG, Pedersen H, Dige T, J Rgensen EB, Holm R. (2014)
Biological conversion of aripiprazole lauroxil - An N-acyloxymethyl aripiprazole prodrug.
Results Pharma Sci, 4: 19-25. [PMID:25756003]
7. Schetz JA, Benjamin PS, Sibley DR. (2000)
Nonconserved residues in the second transmembrane-spanning domain of the D(4) dopamine receptor are molecular determinants of D(4)-selective pharmacology.
Mol Pharmacol, 57 (1): 144-52. [PMID:10617689]
8. Shapiro DA, Renock S, Arrington E, Chiodo LA, Liu LX, Sibley DR, Roth BL, Mailman R. (2003)
Aripiprazole, a novel atypical antipsychotic drug with a unique and robust pharmacology.
Neuropsychopharmacology, 28 (8): 1400-11. [PMID:12784105]
9. Zajdel P, Marciniec K, Maślankiewicz A, Grychowska K, Satała G, Duszyńska B, Lenda T, Siwek A, Nowak G, Partyka A et al.. (2013)
Antidepressant and antipsychotic activity of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole targeting serotonin 5-HT₁A/5-HT₂A/5-HT₇ and dopamine D₂/D₃ receptors.
Eur J Med Chem, 60: 42-50. [PMID:23279866]