Pimozide | CAS#2062-78-4 | Antipsychotic

MedKoo Cat#: 315363 | Name: Pimozide

Description:

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

Pimozide (Orap) is an antipsychotic drug of the diphenylbutylpiperidine class. It was discovered at Janssen Pharmaceutica in 1963. Pimozide has a high potency compared to chlorpromazine (ratio 50-70:1). Pimozide also has special neurologic indications for Tourette syndrome and resistant tics. The side effects include akathisia, tardive dyskinesia, and, more rarely, neuroleptic malignant syndrome and prolongation of the QT interval.

Chemical Structure

Pimozide

CAS#2062-78-4

Theoretical Analysis

MedKoo Cat#: 315363

Name: Pimozide

CAS#: 2062-78-4

Chemical Formula: C28H29F2N3O

Exact Mass: 461.2279

Molecular Weight: 461.55

Elemental Analysis: C, 72.86; H, 6.33; F, 8.23; N, 9.10; O, 3.47

Price and Availability

Size	Price	Availability
50mg	USD 150.00	Ready to ship
100mg	USD 250.00	Ready to ship
200mg	USD 425.00	Ready to ship
500mg	USD 750.00	Ready to ship
1g	USD 1,150.00	2 weeks

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Related CAS #

No Data

Synonym

R 6238; R-6238; R6238; Pimozide; Orap; Opiran.

IUPAC/Chemical Name

1-(1-(4,4-bis(4-fluorophenyl)butyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

InChi Key

YVUQSNJEYSNKRX-UHFFFAOYSA-N

InChi Code

InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)

SMILES Code

O=C1N(C2CCN(CCCC(C3=CC=C(F)C=C3)C4=CC=C(F)C=C4)CC2)C5=CC=CC=C5N1

Appearance

White solid powder

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.

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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#SG60801

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Pimozide is a dopamine receptor antagonist, with Kis of 1.4 nM, 2.5 nM and 588 nM for dopamine D2, D3 and D1 receptors, respectively, that inhibits STAT3 and STAT5 as well as has affinity at α1-adrenoceptor, with a Ki of 39 nM.

In vitro activity:

The migration PC3 and DU145 cells treated with pimozide were evaluated by the scratch assay. After a 24 h treatment with various concentrations of pimozide, cell migration into the scratched area was inhibited in a concentration-dependent manner (Figure 2A). PC3 and DU145 cells were treated with various concentrations of pimozide and measured ROS present in the cells after 24 h using the fluorescent dye, DCFH-DA. As expected, treatment of both cell lines with pimozide increased the production of ROS (Figure 3A). NADPH oxidase is known as a major source of ROS (D’Autréaux and Toledano, 2007). Treatment with DPI, an inhibitor of NADPH oxidase, decreased ROS production in pimozide-treated cancer cells (Figure 3B). It was also investigated whether the production of ROS by pimozide was related to its ability to inhibit the proliferation of prostate cancer cells. When PC3 and DU145 cells were treated with 15 µM pimozide (which increased ROS production compared to the control group) and 100 µM GSH, ROS levels decreased compared with cells treated with pimozide alone (Figure 3C). Furthermore, the presence of 200 µM GSH reduced, to some extent, the pimozide-mediated inhibition of proliferation (Figure 3D). Pimozide treatment reduced expression of the antioxidant enzymes SOD1, Prdx6, and CISD2 (which regulates the accumulation of ROS) (Figures 3E, F). The results of this study suggest that pimozide has a therapeutic effect on prostate cancer in vitro. Reference: Front Pharmacol. 2019; 10: 1517. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6976539/

In vivo activity:

To evaluate the ability of pimozide in inhibiting the growth of brain tumor cells in vivo, U-87 MG luc cells were injected intracranially into the brain of mice using stereotaxic apparatus. Once the tumor cells started growing, mice were randomized into two groups. The treatment group received 25 mg/kg pimozide every day by oral gavage, while the other group served as control and received vehicle only. The growth of tumor in mice was evaluated by using an IVIS imager. The results showed that pimozide treatment suppressed the growth of intracranially implanted U-87 MG tumors by 45% (Figure 9A). Luminescence was also analyzed in the isolated brains from both the control and treatment group. The average luminescence in the treated group was 70% less compared to the control group (Figure 9B). The pimozide-treated group of mice showed a reduction in the activation of STAT3 along with a reduced expression of anti-apoptotic proteins such as Mcl-1 and Bcl-2. Furthermore, pimozide-treated mice showed an increased expression of autophagy marker LC3B (Figure 9C). As an indicator of apoptosis, the increased expression of cleaved caspase 3 and PARP was observed with pimozide treatment. Taken together, these results suggest that reduced tumor growth in the brain by pimozide was due to autophagy-mediated apoptosis. Reference: Cells. 2020 Sep; 9(9): 2141. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7563195/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	30.0	65.00

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 461.55 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. Kim U, Kim CY, Lee JM, Ryu B, Kim J, Shin C, Park JH. Pimozide Inhibits the Human Prostate Cancer Cells Through the Generation of Reactive Oxygen Species. Front Pharmacol. 2020 Jan 16;10:1517. doi: 10.3389/fphar.2019.01517. PMID: 32009948; PMCID: PMC6976539. 2. Choi J, Lee YJ, Yoon YJ, Kim CH, Park SJ, Kim SY, Doo Kim N, Cho Han D, Kwon BM. Pimozide suppresses cancer cell migration and tumor metastasis through binding to ARPC2, a subunit of the Arp2/3 complex. Cancer Sci. 2019 Dec;110(12):37883801. doi: 10.1111/cas.14205. Epub 2019 Nov 15. PMID: 31571309; PMCID: PMC6890432. 3. Al Batran R, Gopal K, Capozzi ME, Chahade JJ, Saleme B, Tabatabaei-Dakhili SA, Greenwell AA, Niu J, Almutairi M, Byrne NJ, Masson G, Kim R, Eaton F, Mulvihill EE, Garneau L, Masters AR, Desta Z, Velázquez-Martínez CA, Aguer C, Crawford PA, Sutendra G, Campbell JE, Dyck JRB, Ussher JR. Pimozide Alleviates Hyperglycemia in Diet-Induced Obesity by Inhibiting Skeletal Muscle Ketone Oxidation. Cell Metab. 2020 May 5;31(5):909-919.e8. doi: 10.1016/j.cmet.2020.03.017. Epub 2020 Apr 9. PMID: 32275862. 4. Ranjan A, Kaushik I, Srivastava SK. Pimozide Suppresses the Growth of Brain Tumors by Targeting STAT3-Mediated Autophagy. Cells. 2020 Sep 22;9(9):2141. doi: 10.3390/cells9092141. PMID: 32971907; PMCID: PMC7563195.

In vitro protocol:

In vivo protocol:

1. Al Batran R, Gopal K, Capozzi ME, Chahade JJ, Saleme B, Tabatabaei-Dakhili SA, Greenwell AA, Niu J, Almutairi M, Byrne NJ, Masson G, Kim R, Eaton F, Mulvihill EE, Garneau L, Masters AR, Desta Z, Velázquez-Martínez CA, Aguer C, Crawford PA, Sutendra G, Campbell JE, Dyck JRB, Ussher JR. Pimozide Alleviates Hyperglycemia in Diet-Induced Obesity by Inhibiting Skeletal Muscle Ketone Oxidation. Cell Metab. 2020 May 5;31(5):909-919.e8. doi: 10.1016/j.cmet.2020.03.017. Epub 2020 Apr 9. PMID: 32275862. 2. Ranjan A, Kaushik I, Srivastava SK. Pimozide Suppresses the Growth of Brain Tumors by Targeting STAT3-Mediated Autophagy. Cells. 2020 Sep 22;9(9):2141. doi: 10.3390/cells9092141. PMID: 32971907; PMCID: PMC7563195

1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Pimozide. 2024 Jul 15. PMID: 30000125. 2: Ajiboye BO, Fatoki TH, Akinola OG, Ajeigbe KO, Bamisaye AF, Domínguez-Martín EM, Rijo P, Oyinloye BE. In silico exploration of anti-prostate cancer compounds from differential expressed genes. BMC Urol. 2024 Jul 3;24(1):138. doi: 10.1186/s12894-024-01521-9. PMID: 38956591; PMCID: PMC11221101. 3: Rogdaki M, McCutcheon RA, D'Ambrosio E, Mancini V, Watson CJ, Fanshawe JB, Carr R, Telesia L, Martini MG, Philip A, Gilbert BJ, Salazar-de-Pablo G, Kyriakopoulos M, Siskind D, Correll CU, Cipriani A, Efthimiou O, Howes OD, Pillinger T. Comparative physiological effects of antipsychotic drugs in children and young people: a network meta-analysis. Lancet Child Adolesc Health. 2024 Jul;8(7):510-521. doi: 10.1016/S2352-4642(24)00098-1. PMID: 38897716. 4: Pergolizzi JV Jr, LeQuang JA, El-Tallawy SN, Wagner M, Ahmed RS, Varrassi G. An update on pharmacotherapy for trigeminal neuralgia. Expert Rev Neurother. 2024 Aug;24(8):773-786. doi: 10.1080/14737175.2024.2365946. Epub 2024 Jun 13. PMID: 38870050. 5: Ceci C, Ruffini F, Falconi M, Grazia Atzori M, Falzon A, Lozzi F, Iacovelli F, D'Atri S, Graziani G, Miguel Lacal P. Pharmacological inhibition of PDGF-C/neuropilin-1 interaction: A novel strategy to reduce melanoma metastatic potential. Biomed Pharmacother. 2024 Jul;176:116766. doi: 10.1016/j.biopha.2024.116766. Epub 2024 May 23. PMID: 38788599. 6: Zhu CX, Yan K, Chen L, Huang RR, Bian ZH, Wei HR, Gu XM, Zhao YY, Liu MC, Suo CX, Li ZK, Yang ZY, Lu MQ, Hua XF, Li L, Zhao ZB, Sun LC, Zhang HF, Gao P, Lian ZX. Targeting OXCT1-mediated ketone metabolism reprograms macrophages to promote antitumor immunity via CD8+ T cells in hepatocellular carcinoma. J Hepatol. 2024 May 15:S0168-8278(24)00342-8. doi: 10.1016/j.jhep.2024.05.007. Epub ahead of print. PMID: 38759889. 7: Kandasamy T, Sarkar S, Sen P, Venkatesh D, Ghosh SS. Concurrent inhibition of IR, ITGB1, and CD36 perturbated the interconnected network of energy metabolism and epithelial-to-mesenchymal transition in breast cancer cells. J Cell Biochem. 2024 Jul;125(7):e30574. doi: 10.1002/jcb.30574. Epub 2024 May 5. PMID: 38704688. 8: Tezcanli Kaymaz B, Gumus N, Celik B, Alcitepe İ, Biray Avci C, Aktan C. Ponatinib and STAT5 Inhibitor Pimozide Combined Synergistic Treatment Applications Potentially Overcome Drug Resistance via Regulating the Cytokine Expressional Network in Chronic Myeloid Leukemia Cells. J Interferon Cytokine Res. 2024 Apr;44(4):178-189. doi: 10.1089/jir.2023.0170. PMID: 38579140. 9: Dai F, Hu C, Li X, Zhang Z, Wang H, Zhou W, Wang J, Geng Q, Dong Y, Tang C. Cav3.2 channel regulates cerebral ischemia/reperfusion injury: a promising target for intervention. Neural Regen Res. 2024 Nov 1;19(11):2480-2487. doi: 10.4103/1673-5374.390966. Epub 2023 Dec 15. PMID: 38526284; PMCID: PMC11090426. 10: Gutierrez RA, Smith P, Kranyak A, Davis M, Koo J. Pimozide-induced tardive dyskinesia in the treatment of delusions of infestation. JAAD Case Rep. 2024 Jan 20;45:71-73. doi: 10.1016/j.jdcr.2024.01.010. PMID: 38406621; PMCID: PMC10883974. 11: Storck W, de Laportalière TT, Yrondi A, Javelot H, Berna F, Montastruc F. Withdrawal syndrome after antipsychotics discontinuation: an analysis of the WHO database of spontaneous reports (Vigibase) between 2000 and 2022. Psychopharmacology (Berl). 2024 Jun;241(6):1205-1212. doi: 10.1007/s00213-024-06554-4. Epub 2024 Feb 20. PMID: 38376511. 12: Alrouji M, Yasmin S, Alhumaydhi FA, Sharaf SE, Shahwan M, Shamsi A. Unlocking therapeutic potential: computational insights into TREM2 protein targeting with FDA-approved drugs for neurodegeneration. J Biomol Struct Dyn. 2024 Feb 19:1-11. doi: 10.1080/07391102.2024.2317987. Epub ahead of print. PMID: 38373093. 13: Jiang G, Zhou X, Hu Y, Tan X, Wang D, Yang L, Zhang Q, Liu S. The antipsychotic drug pimozide promotes apoptosis through the RAF/ERK pathway and enhances autophagy in breast cancer cells. Cancer Biol Ther. 2024 Dec 31;25(1):2302413. doi: 10.1080/15384047.2024.2302413. Epub 2024 Feb 14. PMID: 38356266; PMCID: PMC10878017. 14: Li J, Hua Y, Liu Y, Qu X, Zhang J, Ishida M, Yoshida N, Tabata A, Miyoshi H, Shiba M, Higo S, Sougawa N, Takeda M, Kawamura T, Matsuura R, Okuzaki D, Toyofuku T, Sawa Y, Liu L, Miyagawa S. Human induced pluripotent stem cell- derived closed-loop cardiac tissue for drug assessment. iScience. 2024 Jan 23;27(2):108992. doi: 10.1016/j.isci.2024.108992. PMID: 38333703; PMCID: PMC10850789. 15: Alkafaas SS, Abdallah AM, Hassan MH, Hussien AM, Elkafas SS, Loutfy SA, Mikhail A, Murad OG, Elsalahaty MI, Hessien M, Elshazli RM, Alsaeed FA, Ahmed AE, Kamal HK, Hafez W, El-Saadony MT, El-Tarabily KA, Ghosh S. Molecular docking as a tool for the discovery of novel insight about the role of acid sphingomyelinase inhibitors in SARS- CoV-2 infectivity. BMC Public Health. 2024 Feb 6;24(1):395. doi: 10.1186/s12889-024-17747-z. PMID: 38321448; PMCID: PMC10848368. 16: Huang J, Liang L, Jiang S, Liu Y, He H, Sun X, Li Y, Xie L, Tao Y, Cong L, Jiang Y. BDH1-mediated LRRC31 regulation dependent on histone lysine β-hydroxybutyrylation to promote lung adenocarcinoma progression. MedComm (2020). 2023 Dec 13;4(6):e449. doi: 10.1002/mco2.449. PMID: 38098610; PMCID: PMC10719427. 17: Mardanshahi A, Vaseghi S, Hosseinimehr SJ, Abedi SM, Molavipordanjani S. 99mTc(CO)3-labeled 1-(2-Pyridyl)piperazine derivatives as radioligands for 5-HT7 receptors. Ann Nucl Med. 2024 Feb;38(2):139-153. doi: 10.1007/s12149-023-01885-2. Epub 2023 Nov 30. PMID: 38032496. 18: Guedes NLKO, Dwan AJ, Gerlero P, Nico MMS. Delusional infestation treated with risperidone: a series of 27 patients. Clin Exp Dermatol. 2024 Mar 21;49(4):364-367. doi: 10.1093/ced/llad411. PMID: 38001055. 19: Rana MH, Khan AAG, Khalid I, Ishfaq M, Javali MA, Baig FAH, Kota MZ, Khader MA, Hameed MS, Shaik S, Das G. Therapeutic Approach for Trigeminal Neuralgia: A Systematic Review. Biomedicines. 2023 Sep 22;11(10):2606. doi: 10.3390/biomedicines11102606. PMID: 37892981; PMCID: PMC10604820. 20: Pisoni LA, Semple SJ, Liu S, Sykes MJ, Venter H. Combined Structure- and Ligand-Based Approach for the Identification of Inhibitors of AcrAB-TolC in Escherichia coli. ACS Infect Dis. 2023 Dec 8;9(12):2504-2522. doi: 10.1021/acsinfecdis.3c00350. Epub 2023 Oct 27. PMID: 37888944.

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BJG-01-181

MedKoo CAT#: 465481

CAS#: unknown