Pimozide

• CAT Number: R057848
• CAS Number: 2062-78-4
• Molecular Formula: C28H29F2N3O
• Molecular Weight: 461.557
• Purity: ≥95%
• Target: Dopamine Receptor
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: 3-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1H-benzimidazol-2-one
• InChI: 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)
• InChIKey: YVUQSNJEYSNKRX-UHFFFAOYSA-N
• SMILES: C1CN(CCC1N2C3=CC=CC=C3NC2=O)CCCC(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F

Pimozide (Orap) is an antipsychotic drug of the diphenylbutylpiperidine class. It was discovered at Janssen Pharmaceutica in 1963. It has a high potency compared to chlorpromazine (ratio 50-70:1). On a weight basis it is even more potent than haloperidol. It 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.

Reference

1:Inhibition of wnt/β-catenin Signaling in Hepatocellular Carcinoma by an Antipsychotic Drug Pimozide. Fako V, Yu Z, Henrich CJ, Ransom T, Budhu AS, Wang XW.Int J Biol Sci. 2016 Apr 28;12(7):768-75. doi: 10.7150/ijbs.14718. eCollection 2016. PMID: 27313491 Free PMC Article2:The antipsychotic drug pimozide inhibits cell growth in prostate cancer through suppression of STAT3 activation. Zhou W, Chen MK, Yu HT, Zhong ZH, Cai N, Chen GZ, Zhang P, Chen JJ.Int J Oncol. 2016 Jan;48(1):322-8. doi: 10.3892/ijo.2015.3229. Epub 2015 Nov 4. PMID: 26549437 3:The neuroleptic drug pimozide inhibits stem-like cell maintenance and tumorigenicity in hepatocellular carcinoma. Chen JJ, Cai N, Chen GZ, Jia CC, Qiu DB, Du C, Liu W, Yang Y, Long ZJ, Zhang Q.Oncotarget. 2017 Mar 14;8(11):17593-17609. doi: 10.18632/oncotarget.4307. PMID: 26061710 Free PMC Article4:Exacerbation of tics after combining aripiprazole with pimozide: a case with Tourette Syndrome. Mazlum B, Zaimoğlu S, Öztop DB.J Clin Psychopharmacol. 2015 Jun;35(3):350-1. doi: 10.1097/JCP.0000000000000331. No abstract available. PMID: 25928702 5:The Influence of the CYP3A4*22 Polymorphism and CYP2D6 Polymorphisms on Serum Concentrations of Aripiprazole, Haloperidol, Pimozide, and Risperidone in Psychiatric Patients. van der Weide K, van der Weide J.J Clin Psychopharmacol. 2015 Jun;35(3):228-36. doi: 10.1097/JCP.0000000000000319. PMID: 25868121 6:Timing recalibration in childhood Tourette syndrome associated with persistent pimozide treatment. Vicario CM, Gulisano M, Martino D, Rizzo R.J Neuropsychol. 2016 Sep;10(2):211-22. doi: 10.1111/jnp.12064. Epub 2015 Feb 23. PMID: 25705969 7:Pimozide, a novel fatty acid binding protein 4 inhibitor, promotes adipogenesis of 3T3-L1 cells by activating PPARγ. Wang Y, Lin HQ, Law WK, Liang WC, Zhang JF, Hu JS, Ip TM, Waye MM, Wan DC.ACS Chem Neurosci. 2015 Feb 18;6(2):211-8. doi: 10.1021/cn5002107. Epub 2014 Dec 3. PMID: 25437245 8:Signal transducer and activator of transcription 5a inhibited by pimozide may regulate survival of goat mammary gland epithelial cells by regulating parathyroid hormone-related protein. Li H, Zheng H, Sun Y, Yu Q, Li L.Gene. 2014 Nov 10;551(2):279-89. doi: 10.1016/j.gene.2014.09.005. Epub 2014 Sep 4. PMID: 25194899 9:Inhibition of activated STAT5 in Bcr/Abl expressing leukemia cells with new pimozide derivatives. Rondanin R, Simoni D, Romagnoli R, Baruchello R, Marchetti P, Costantini C, Fochi S, Padroni G, Grimaudo S, Pipitone RM, Meli M, Tolomeo M.Bioorg Med Chem Lett. 2014 Sep 15;24(18):4568-74. doi: 10.1016/j.bmcl.2014.07.069. Epub 2014 Aug 1. PMID: 25131537 10:Pimozide: parasitosis (delusional). Generali JA, Cada DJ.Hosp Pharm. 2014 Feb;49(2):134-5. doi: 10.1310/hpj4902-134. PMID: 24623867 Free PMC Article