Synonym
OPC-14597; OPC 14597; OPC14597; Abilify; Abilitat; Abilify Discmelt.
IUPAC/Chemical Name
7-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one
InChi Key
CEUORZQYGODEFX-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
C1CC(=O)NC2=C1C=CC(=C2)OCCCCN3CCN(CC3)C4=C(C(=CC=C4)Cl)Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Aripiprazole (OPC-14597) is a human 5-HT1A receptor partial agonist with a Ki of 4.2 nM.
In vitro activity:
The 6-3 cells were pre-treated with DMSO (0.1%), aripiprazole (5, 10 and 20 μM) or D2 receptor full agonist, quinpirole (5, 10 and 20μM) for 12h, then the cells were treated with each drug and IFN-γ (50 U/mL) for 48h. Aripiprazole significantly inhibited the NO release dose-dependently in comparison with the positive control (DMSO + IFN-γ group). In order to confirm whether these effects are specific to IFN-γ–induced microglial activation or not, the effect of aripiprazole on LPS-induced microglial activation was measured. Aripiprazole significantly inhibited NO release by LPS-activated 6-3 microglia (Fig. 2b). These results suggest that the inhibitory effects of aripiprazole were not specific to IFN-γ receptor-mediated signaling. In addition, prepared rat primary microglial cells were also prepared in order to confirm the relevance of our results in these cells. Similar to what was observed in the 6-3 murine microglial cells, aripiprazole significantly inhibited NO release from LPS-activated rat primary microglia. Then. the 6-3 cells were pre-treated with DMSO (0.1%), aripiprazole (5, 10 and 20μM) or quinpirole (5, 10 and 20μM) for 12h, then the cells were treated with each drug and IFN-γ (50 U/mL) for 48h. Aripiprazole strongly inhibited the release of TNF-α dose-dependently. Therefore, the present results suggest that aripiprazole may ameliorate white matter disorders via inhibiting microglial activation in the brain of patients with schizophrenia.
Reference: J Neurochem. 2008 Jul;106(2):815-25. https://onlinelibrary.wiley.com/doi/full/10.1111/j.1471-4159.2008.05435.x
In vivo activity:
Electrophysiological recordings were conducted from MAM rats and SAL rats, with each group receiving either VEH or ARI (aripiprazole ) (3 mg/kg or 10 mg/kg, p.o.). VEH-treated MAM rats (n = 6 rats, 63 neurons) exhibited the anticipated elevation in population activity with an average of 1.7 ± 0.1 cells/track compared to VEH-treated SAL rats (n = 8 rats, 61 neurons) which had an average of 1.1 ± 0.1 cells/track (Fig. 1a; 2-way ANOVA main effects: for MAM F(2, 40) = 3.189, p = 0.010; for ARI F(2, 40) = 5.049, p = 0.011; MAM-by-ARI interaction F(2, 40) = 5.882, p = 0.005; post hoc MAM control vs SAL control p = 0.001). Acute ARI treatment significantly reduced DA neuron population activity in MAM rats, both at 3 mg/kg (n = 6 rats, 37 neurons; post hoc MAM control vs MAM 3 mg/kg: p = 0.007) and 10 mg/kg (n = 10 rats, 63 neurons; post hoc MAM control vs MAM 10 mg/kg: p = 0.001) compared to VEH-treated MAM rats. Overall, this study demonstrates that ARI rapidly normalizes the hyperdopaminergic state observed in MAM rats without effect on DA neuron population activity in a normal system.
Reference: Neuropsychopharmacology. 2019 Feb; 44(3): 572–580. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6333840/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
67.0 |
149.42 |
| Ethanol |
50.0 |
111.51 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
448.39
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Brust TF, Hayes MP, Roman DL, Watts VJ. New functional activity of aripiprazole revealed: Robust antagonism of D2 dopamine receptor-stimulated Gβγ signaling. Biochem Pharmacol. 2015 Jan 1;93(1):85-91. doi: 10.1016/j.bcp.2014.10.014. Epub 2014 Nov 7. PMID: 25449598; PMCID: PMC4276521. 2. Kato T, Mizoguchi Y, Monji A, Horikawa H, Suzuki SO, Seki Y, Iwaki T, Hashioka S, Kanba S. Inhibitory effects of aripiprazole on interferon-gamma-induced microglial activation via intracellular Ca2+ regulation in vitro. J Neurochem. 2008 Jul;106(2):815-25. doi: 10.1111/j.1471-4159.2008.05435.x. Epub 2008 Apr 19. PMID: 18429930.
3. Gil CH, Kim YR, Lee HJ, Jung DH, Shin HK, Choi BT. Aripiprazole exerts a neuroprotective effect in mouse focal cerebral ischemia. Exp Ther Med. 2018 Jan;15(1):745-750. doi: 10.3892/etm.2017.5443. Epub 2017 Nov 6. PMID: 29399080; PMCID: PMC5772374.
4. Sonnenschein SF, Gill KM, Grace AA. State-dependent effects of the D2 partial agonist aripiprazole on dopamine neuron activity in the MAM neurodevelopmental model of schizophrenia. Neuropsychopharmacology. 2019 Feb;44(3):572-580. doi: 10.1038/s41386018-0219-1. Epub 2018 Sep 18. PMID: 30267014; PMCID: PMC6333840.
In vitro protocol:
1. Brust TF, Hayes MP, Roman DL, Watts VJ. New functional activity of aripiprazole revealed: Robust antagonism of D2 dopamine receptor-stimulated Gβγ signaling. Biochem Pharmacol. 2015 Jan 1;93(1):85-91. doi: 10.1016/j.bcp.2014.10.014. Epub 2014 Nov 7. PMID: 25449598; PMCID: PMC4276521. 2. Kato T, Mizoguchi Y, Monji A, Horikawa H, Suzuki SO, Seki Y, Iwaki T, Hashioka S, Kanba S. Inhibitory effects of aripiprazole on interferon-gamma-induced microglial activation via intracellular Ca2+ regulation in vitro. J Neurochem. 2008 Jul;106(2):815-25. doi: 10.1111/j.1471-4159.2008.05435.x. Epub 2008 Apr 19. PMID: 18429930.
In vivo protocol:
1. Gil CH, Kim YR, Lee HJ, Jung DH, Shin HK, Choi BT. Aripiprazole exerts a neuroprotective effect in mouse focal cerebral ischemia. Exp Ther Med. 2018 Jan;15(1):745-750. doi: 10.3892/etm.2017.5443. Epub 2017 Nov 6. PMID: 29399080; PMCID: PMC5772374.
2. Sonnenschein SF, Gill KM, Grace AA. State-dependent effects of the D2 partial agonist aripiprazole on dopamine neuron activity in the MAM neurodevelopmental model of schizophrenia. Neuropsychopharmacology. 2019 Feb;44(3):572-580. doi: 10.1038/s41386018-0219-1. Epub 2018 Sep 18. PMID: 30267014; PMCID: PMC6333840.
1: Grall-Bronnec M, Sauvaget A, Perrouin F, Leboucher J, Etcheverrigaray F, Challet-Bouju G, Gaboriau L, Derkinderen P, Jolliet P, Victorri-Vigneau C. Pathological Gambling Associated With Aripiprazole or Dopamine Replacement Therapy: Do Patients Share the Same Features? A Review. J Clin Psychopharmacol. 2015 Dec 12. [Epub ahead of print] PubMed PMID: 26658263.
2: Diomšina B, Rasmussen PD, Danilevičiütė V. CLINICAL EXPERIENCE OF LONG-TERM TREATMENT WITH ARIPIPRAZOLE (ABILIFY) IN CHILDREN AND ADOLESCENTS AT THE CHILD AND ADOLESCENT PSYCHIATRIC CLINIC 1 IN ROSKILDE, DENMARK. Acta Pol Pharm. 2015 May-Jun;72(3):597-606. PubMed PMID: 26642668.
3: Monga V, Padala PR. Aripiprazole for Treatment of Apathy. Innov Clin Neurosci. 2015 Sep-Oct;12(9-10):33-6. PubMed PMID: 26634180; PubMed Central PMCID: PMC4655898.
4: Tokisato K, Fukunaga K, Tokunaga M, Watanabe S, Nakanishi R, Yamanaga H. Aripiprazole Can Improve Apraxia of Eyelid Opening in Parkinson's Disease. Intern Med. 2015;54(23):3061-4. doi: 10.2169/internalmedicine.54.4279. Epub 2015 Dec 1. PubMed PMID: 26631893.
5: Palaniappan P. Aripiprazole as a treatment option for clozapine-induced enuresis. Indian J Pharmacol. 2015 Sep-Oct;47(5):574-5. doi: 10.4103/0253-7613.165176. PubMed PMID: 26600658; PubMed Central PMCID: PMC4621690.
6: Frank GK. Aripiprazole, a partial dopamine agonist to improve adolescent anorexia nervosa-A case series. Int J Eat Disord. 2015 Nov 23. doi: 10.1002/eat.22485. [Epub ahead of print] PubMed PMID: 26593328.
7: Prommer E. Aripiprazole: A New Option in Delirium. Am J Hosp Palliat Care. 2015 Nov 20. pii: 1049909115612800. [Epub ahead of print] PubMed PMID: 26589880.
8: Burback L. Management of a microprolactinoma with aripiprazole in a woman with cabergoline-induced mania. Endocrinol Diabetes Metab Case Rep. 2015;2015:150100. doi: 10.1530/EDM-15-0100. Epub 2015 Oct 6. PubMed PMID: 26587235; PubMed Central PMCID: PMC4650831.
9: Citrome L. Aripiprazole Long-Acting Injectable Formulations for Schizophrenia: Aripiprazole Monohydrate and Aripiprazole Lauroxil. Expert Rev Clin Pharmacol. 2015 Nov 17. [Epub ahead of print] PubMed PMID: 26573020.
10: Suzuki H, Sekiguchi G. The influence of aripiprazole once-monthly on the clinical symptoms and cognitive function in two schizophrenia patients: preliminary results. Psychiatry Clin Neurosci. 2015 Nov 10. doi: 10.1111/pcn.12374. [Epub ahead of print] PubMed PMID: 26556467.
