Thioridazine

• CAT Number: R063030
• CAS Number: 50-52-2
• Molecular Formula: C21H26N2S2
• Molecular Weight: 370.573
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine
• InChI: InChI=1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
• InChIKey: KLBQZWRITKRQQV-UHFFFAOYSA-N
• SMILES: CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)SC

Thioridazine is a piperidine typical antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis; the branded product was withdrawn worldwide in 2005 because it caused severe cardiac arrhythmias, however, generic versions are available in the US.

Reference

1:Thioridazine Therapy and CYP2D6 Genotypes. Dean L.In: Pratt V, McLeod H, Dean L, Malheiro A, Rubinstein W, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012-.2017 Feb 9. PMID: 28520378 Free Books & Documents2:Thioridazine has potent antitumor effects on lung cancer stem-like cells. Shen J, Ma B, Zhang X, Sun X, Han J, Wang Y, Chu L, Xu H, Yang Y.Oncol Lett. 2017 Mar;13(3):1563-1568. doi: 10.3892/ol.2017.5651. Epub 2017 Jan 25. PMID: 28454291 Free PMC Article3:Sulpiride, Amisulpride, Thioridazine, and Olanzapine: Interaction with Model Membranes. Thermodynamic and Structural Aspects. Skrobecki P, Chmielińska A, Bonarek P, Stepien P, Wisniewska-Becker A, Dziedzicka-Wasylewska M, Polit A.ACS Chem Neurosci. 2017 Apr 12. doi: 10.1021/acschemneuro.7b00057. [Epub ahead of print] PMID: 28375612 4:Systemic thioridazine in combination with dicloxacillin against early aortic graft infections caused by Staphylococcus aureus in a porcine model: In vivo results do not reproduce the in vitro synergistic activity. Stenger M, Behr-Rasmussen C, Klein K, Grønnemose RB, Andersen TE, Klitgaard JK, Kolmos HJ, Lindholt JS.PLoS One. 2017 Mar 9;12(3):e0173362. doi: 10.1371/journal.pone.0173362. eCollection 2017. PMID: 28278183 Free PMC Article5:Combination of thioridazine and dicloxacillin as a possible treatment strategy of staphylococci. Rasmussen KS, Poulsen MØ, Jacobsen K, Skov MN, Kolmos HJ, Kallipolitis BH, Klitgaard JK.New Microbiol. 2017 Apr;40(2):146-147. Epub 2017 Mar 1. PMID: 28255602 Free Article6:[Thioridazine Sensitizes Apoptotic Effect of TRAIL in Human Lung Cancer PC9 Cells Through ER Stress Mediated Up-regulation of DR5]. Li J, Wang Y, Liu L, Yuan Y, Bao Y.Zhongguo Fei Ai Za Zhi. 2017 Feb 20;20(2):80-87. doi: 10.3779/j.issn.1009-3419.2017.02.02. Chinese. PMID: 28228218 Free Article7:Thioridazine enhances sensitivity to carboplatin in human head and neck cancer cells through downregulation of c-FLIP and Mcl-1 expression. Seo SU, Cho HK, Min KJ, Woo SM, Kim S, Park JW, Kim SH, Choi YH, Keum YS, Hyun JW, Park HH, Lee SH, Kim DE, Kwon TK.Cell Death Dis. 2017 Feb 9;8(2):e2599. doi: 10.1038/cddis.2017.8. PMID: 28182008 Free PMC Article8:Thioridazine: A Non-Antibiotic Drug Highly Effective, in Combination with First Line Anti-Tuberculosis Drugs, against Any Form of Antibiotic Resistance of Mycobacterium tuberculosis Due to Its Multi-Mechanisms of Action. Amaral L, Viveiros M.Antibiotics (Basel). 2017 Jan 14;6(1). pii: E3. doi: 10.3390/antibiotics6010003. Review. PMID: 28098814 Free PMC Article9:The Effect of Fluphenazine and Thioridazine on Toxoplasma gondii In Vivo. Saraei M, Ghaderi Y, Mosavi T, Shahnazi M, Nassiri-Asl M, Jahanihashemi H.Iran J Parasitol. 2016 Apr-Jun;11(2):226-231. PMID: 28096857 Free PMC Article10:Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis. Scalacci N, Brown AK, Pavan FR, Ribeiro CM, Manetti F, Bhakta S, Maitra A, Smith DL, Petricci E, Castagnolo D.Eur J Med Chem. 2017 Feb 15;127:147-158. doi: 10.1016/j.ejmech.2016.12.042. Epub 2016 Dec 23. PMID: 28039773