Aripiprazole monohydrate | CAS# 851220-85-4 | Antipsychotic

MedKoo Cat#: 573269 | Name: Aripiprazole monohydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aripiprazole monohydrate is a third-generation antipsychotic with a dopamine receptor-binding profile distinct from other second-generation antipsychotics, used in schizophrenia.

Chemical Structure

Aripiprazole monohydrate

CAS#851220-85-4 (hydrate)

Theoretical Analysis

MedKoo Cat#: 573269

Name: Aripiprazole monohydrate

CAS#: 851220-85-4 (hydrate)

Chemical Formula: C23H29Cl2N3O3

Exact Mass: 0.0000

Molecular Weight: 466.40

Elemental Analysis: C, 59.23; H, 6.27; Cl, 15.20; N, 9.01; O, 10.29

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,650.00	Ready to ship

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Related CAS #

129722-12-9 (free base) 851220-85-4 (hydrate) 1259305-26-4 (cavoxil) 1259305-29-7 (lauroxil)

Synonym

Aripiprazole monohydrate; OPC 14597; OPC14597; OPC-14597; OPC 31; OPC-31; OPC31; Abilitat;

IUPAC/Chemical Name

7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one hydrate

InChi Key

UXQBDXJXIVDBTF-UHFFFAOYSA-N

InChi Code

1S/C23H27Cl2N3O2.H2O/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);1H2

SMILES Code

ClC1=C(Cl)C(N2CCN(CCCCOC3=CC(NC(CC4)=O)=C4C=C3)CC2)=CC=C1.O

Appearance

Solid powder

Purity

>99% (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

Shelf Life

>3 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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#YXM201029

QC Data

View QC data: current batch, Lot#YXM201029

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

TBD

In vitro activity:

In conclusion, aripiprazole inhibits cell proliferation in breast cancer MCF-7 cells line in a concentration dependent manner. Mechanistic studies indicated that the anti-cancer effect of aripiprazole may be due to an enhanced apoptosis in MCF-7 cells line. This was further supported by observing increased nuclear condensation in MCF-7 cells line. The drug inhibited cell cycle progression in subG0G1 phase. Aripiprazole also increased the expression of certain pro-apoptotic genes (caspases 3, and BCL10), while expression of anti-apoptotic genes (BCL2L1, and c-myc) that are involved in the progression of breast cancer were decreased. This study thus indicated that aripiprazole inhibit the cancer cell proliferation through apoptosis. Further studies, however, are required to study the effect of aripiprazole on intrinsic or extrinsic pathways of apoptosis, as well as to enhance its activity by structural modifications. Reference: PLoS One. 2020; 15(8): e0235676. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7398703/

In vivo activity:

The present study demonstrated the in vivo effects of aripiprazole on the downstream pathways of the D2R, by comparing it with haloperidol and bifeprunox. The results of the current study showed that aripiprazole had similar effects on PKA subunits to haloperidol, but not bifeprunox in the CPu and VTA, indicating that relatively lower intrinsic activity of aripiprazole on D2R might be the mechanism of aripiprazole to exert its therapeutic effects on treating positive symptoms of schizophrenia; on the other hand, aripiprazole displayed a very different action mode on the GSK3β activity from the other two chemicals, probably explaining its therapeutic effects on both positive and negative symptoms of schizophrenia, with reduced EPS. Together, these in vivo findings suggest that the relatively low intrinsic activity at D2R might be the reason that aripiprazole possesses unique pharmacological profiles and clinical effects from the other antipsychotic drugs. Reference: PLoS One. 2015; 10(7): e0132722. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498891/

Preparing Stock Solutions

The following data is based on the product molecular weight 466.40 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. Badran A, Tul-Wahab A, Zafar H, Mohammad N, Imad R, Ashfaq Khan M, Baydoun E, Choudhary MI. Antipsychotics drug aripiprazole as a lead against breast cancer cell line (MCF-7) in vitro. PLoS One. 2020 Aug 3;15(8):e0235676. doi: 10.1371/journal.pone.0235676. PMID: 32746451; PMCID: PMC7398703. 2. Kim MS, Yoo BC, Yang WS, Han SY, Jeong D, Song JM, Kim KH, Aravinthan A, Kim JH, Kim JH, Kim SC, Cho JY. Src is the primary target of aripiprazole, an atypical antipsychotic drug, in its anti-tumor action. Oncotarget. 2017 Dec 8;9(5):5979-5992. doi: 10.18632/oncotarget.23192. PMID: 29464048; PMCID: PMC5814188. 3. Rizzo F, Nespoli E, Abaei A, Bar-Gad I, Deelchand DK, Fegert J, Rasche V, Hengerer B, Boeckers TM. Aripiprazole Selectively Reduces Motor Tics in a Young Animal Model for Tourette's Syndrome and Comorbid Attention Deficit and Hyperactivity Disorder. Front Neurol. 2018 Feb 13;9:59. doi: 10.3389/fneur.2018.00059. PMID: 29487562; PMCID: PMC5816975. 4. Pan B, Chen J, Lian J, Huang XF, Deng C. Unique Effects of Acute Aripiprazole Treatment on the Dopamine D2 Receptor Downstream cAMP-PKA and Akt-GSK3β Signalling Pathways in Rats. PLoS One. 2015 Jul 10;10(7):e0132722. doi: 10.1371/journal.pone.0132722. PMID: 26162083; PMCID: PMC4498891.

In vitro protocol:

In vivo protocol:

1. Rizzo F, Nespoli E, Abaei A, Bar-Gad I, Deelchand DK, Fegert J, Rasche V, Hengerer B, Boeckers TM. Aripiprazole Selectively Reduces Motor Tics in a Young Animal Model for Tourette's Syndrome and Comorbid Attention Deficit and Hyperactivity Disorder. Front Neurol. 2018 Feb 13;9:59. doi: 10.3389/fneur.2018.00059. PMID: 29487562; PMCID: PMC5816975. 2. Pan B, Chen J, Lian J, Huang XF, Deng C. Unique Effects of Acute Aripiprazole Treatment on the Dopamine D2 Receptor Downstream cAMP-PKA and Akt-GSK3β Signalling Pathways in Rats. PLoS One. 2015 Jul 10;10(7):e0132722. doi: 10.1371/journal.pone.0132722. PMID: 26162083; PMCID: PMC4498891.

1: Citrome L, Du Y, Weiden PJ. Assessing effectiveness of aripiprazole lauroxil vs placebo for the treatment of schizophrenia using number needed to treat and number needed to harm. Neuropsychiatr Dis Treat. 2019 Sep 12;15:2639-2646. doi: 10.2147/NDT.S207910. eCollection 2019. PubMed PMID: 31686823; PubMed Central PMCID: PMC6751763. 2: Hard ML, Wehr A, von Moltke L, Du Y, Farwick S, Walling DP, Sonnenberg J. Pharmacokinetics and safety of deltoid or gluteal injection of aripiprazole lauroxil NanoCrystal(®) Dispersion used for initiation of the long-acting antipsychotic aripiprazole lauroxil. Ther Adv Psychopharmacol. 2019 Jul 2;9:2045125319859964. doi: 10.1177/2045125319859964. eCollection 2019. PubMed PMID: 31308935; PubMed Central PMCID: PMC6607563. 3: Farwick S, Hickey MB, Jacobs G, Faldu SP, Vandiver J, Weiden PJ. Best Practices for Aripiprazole Lauroxil Administration: From Formulation Development to Injection Technique. J Psychiatr Pract. 2019 Mar;25(2):82-90. doi: 10.1097/PRA.0000000000000376. PubMed PMID: 30849056. 4: Correll CU, Stanford AD, Claxton A, Du Y, Weiden PJ. Social and functional outcomes with two doses of aripiprazole lauroxil vs placebo in patients with schizophrenia: a post-hoc analysis of a 12-week phase 3 efficacy study. Psychiatry Res. 2019 Apr;274:176-181. doi: 10.1016/j.psychres.2019.02.021. Epub 2019 Feb 14. PubMed PMID: 30802689. 5: Miller BJ, Claxton A, Du Y, Weiden PJ, Potkin SG. Switching patients with schizophrenia from paliperidone palmitate to aripiprazole lauroxil: A 6-month, prospective, open-label study. Schizophr Res. 2019 Jun;208:44-48. doi: 10.1016/j.schres.2019.01.038. Epub 2019 Feb 7. PubMed PMID: 30745067. 6: Nasrallah HA, Aquila R, Du Y, Stanford AD, Claxton A, Weiden PJ. Long-term safety and tolerability of aripiprazole lauroxil in patients with schizophrenia. CNS Spectr. 2019 Aug;24(4):395-403. doi: 10.1017/S1092852918001104. Epub 2018 Aug 15. PubMed PMID: 30109845. 7: Ehret MJ, Davis E, Luttrell SE, Clark C. Aripiprazole Lauroxil NanoCrystal(®) Dispersion Technology (Aristada Initio(®)). Clin Schizophr Relat Psychoses. Summer 2018;12(2):92-96. doi: 10.3371/CSRP.EHDA071918. PubMed PMID: 30040476. 8: Hard ML, Wehr AY, Du Y, Weiden PJ, Walling D, von Moltke L. Pharmacokinetic Evaluation of a 1-Day Treatment Initiation Option for Starting Long-Acting Aripiprazole Lauroxil for Schizophrenia. J Clin Psychopharmacol. 2018 Oct;38(5):435-441. doi: 10.1097/JCP.0000000000000921. PubMed PMID: 30015676; PubMed Central PMCID: PMC6133194. 9: Hard ML, Wehr AY, Sadler BM, Mills RJ, von Moltke L. Population Pharmacokinetic Analysis and Model-Based Simulations of Aripiprazole for a 1-Day Initiation Regimen for the Long-Acting Antipsychotic Aripiprazole Lauroxil. Eur J Drug Metab Pharmacokinet. 2018 Aug;43(4):461-469. doi: 10.1007/s13318-018-0488-4. PubMed PMID: 29943125; PubMed Central PMCID: PMC6060990. 10: Weiden PJ, Du Y, Liu CC, Stanford AD. Switching stable patients with schizophrenia from their oral antipsychotics to aripiprazole lauroxil: a post hoc safety analysis of the initial 12-week crossover period. CNS Spectr. 2019 Aug;24(4):419-425. doi: 10.1017/S1092852918000986. Epub 2018 Jun 26. PubMed PMID: 29941057. 11: Sun Y, Lu X, Gai Y, Sha C, Leng G, Yang X, Liu W. LC-MS/MS method for the determination of the prodrug aripiprazole lauroxil and its three metabolites in plasma and its application to in vitro biotransformation and animal pharmacokinetic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Apr 1;1081-1082:67-75. doi: 10.1016/j.jchromb.2018.02.011. Epub 2018 Feb 10. PubMed PMID: 29510329. 12: Cameron C, Zummo J, Desai D, Drake C, Hutton B, Kotb A, Weiden PJ. Efficacy and safety of aripiprazole lauroxil once-monthly versus aripiprazole once-monthly long-acting injectable formulations in patients with acute symptoms of schizophrenia: an indirect comparison of two double-blind placebo-controlled studies. Curr Med Res Opin. 2018 Apr;34(4):725-733. doi: 10.1080/03007995.2017.1410471. Epub 2018 Jan 10. PubMed PMID: 29179595. 13: Frampton JE. Aripiprazole Lauroxil: A Review in Schizophrenia. Drugs. 2017 Dec;77(18):2049-2056. doi: 10.1007/s40265-017-0848-4. Review. PubMed PMID: 29177572. 14: McEvoy JP, Risinger R, Mykhnyak S, Du Y, Liu CC, Stanford AD, Weiden PJ. Durability of Therapeutic Response With Long-Term Aripiprazole Lauroxil Treatment Following Successful Resolution of an Acute Episode of Schizophrenia. J Clin Psychiatry. 2017 Sep/Oct;78(8):1103-1109. doi: 10.4088/JCP.17m11625. PubMed PMID: 28937706. 15: Nasrallah HA, Aquila R, Stanford AD, Jamal HH, Weiden PJ, Risinger R. Metabolic and Endocrine Profiles During 1-Year Treatment of Outpatients with Schizophrenia with Aripiprazole Lauroxil. Psychopharmacol Bull. 2017 Aug 1;47(3):35-43. PubMed PMID: 28839338; PubMed Central PMCID: PMC5546549. 16: Risinger R, Hard M, Weiden PJ. A Phase-1 Study Comparing Pharmacokinetic and Safety Profiles of Three Different Dose Intervals of Aripiprazole Lauroxil. Psychopharmacol Bull. 2017 Aug 1;47(3):26-34. PubMed PMID: 28839337; PubMed Central PMCID: PMC5546548. 17: Cameron C, Zummo J, Desai DN, Drake C, Hutton B, Kotb A, Weiden PJ. Aripiprazole Lauroxil Compared with Paliperidone Palmitate in Patients with Schizophrenia: An Indirect Treatment Comparison. Value Health. 2017 Jul - Aug;20(7):876-885. doi: 10.1016/j.jval.2017.03.010. Epub 2017 May 9. Review. PubMed PMID: 28712616. 18: Citrome L, Risinger R, Cutler AJ, Du Y, Zummo J, Nasrallah HA, Silverman BL. Effect of aripiprazole lauroxil in patients with acute schizophrenia as assessed by the Positive and Negative Syndrome Scale-supportive analyses from a Phase 3 study. CNS Spectr. 2018 Aug;23(4):284-290. doi: 10.1017/S1092852917000396. Epub 2017 Jun 19. PubMed PMID: 28625204. 19: Hard ML, Mills RJ, Sadler BM, Wehr AY, Weiden PJ, von Moltke L. Pharmacokinetic Profile of a 2-Month Dose Regimen of Aripiprazole Lauroxil: A Phase I Study and a Population Pharmacokinetic Model. CNS Drugs. 2017 Jul;31(7):617-624. doi: 10.1007/s40263-017-0447-7. PubMed PMID: 28597226; PubMed Central PMCID: PMC5511303. 20: Hard ML, Mills RJ, Sadler BM, Turncliff RZ, Citrome L. Aripiprazole Lauroxil: Pharmacokinetic Profile of This Long-Acting Injectable Antipsychotic in Persons With Schizophrenia. J Clin Psychopharmacol. 2017 Jun;37(3):289-295. doi: 10.1097/JCP.0000000000000691. PubMed PMID: 28350572; PubMed Central PMCID: PMC5400404.