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Thioridazine Hydrochloride

Product ID T2936
Cas No. 130-61-0
Purity ≥98%
Product Unit SizeCostQuantityStock
500 mg $55.70 In stock
5 g $108.70 In stock
25 g $434.90 In stock
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Description

Thioridazine is a piperadine phenothiazine derivative classified as a ‘typical’ antipsychotic for its potent inhibition of D2 receptors. Thioridazine displays activity at D1-5 receptors, H1/2 histamine receptors, M1-5 muscarinic acetylcholine receptors (mAChRs), α1/2-adrenergic receptors, and 5-HT1/2/5/6/7 receptors; thioridazine also modulates activity of the norepinephrine transporter (NET). In addition to its well-established antipsychotic and sedative activities, thioridazine also exhibits antibacterial, anti-angiogenic, and anticancer properties. In vitro, thioridazine enhances β-lactam antibacterial capabilities; this compound inhibits peptidoglycan synthesis by interfering with the formation of pentaglycine branches and inducing amino acid shortages. Thioridazine inhibits phosphorylation of Akt, PDK-1, mTOR, and p70S6K, inhibiting migration, invasion, and capillary-like tube formation of cells. In cervical and endometrial cancer cells, thioridazine downregulates expression of cyclins D1 and A as well as cyclin-dependent kinase 4 (CDK4) and upregulates expression of p21 and p27, inducing apoptosis. In vivo, this compound decreases colony-forming units of Mycobacterium tuberculosis, inducing expression of the sigma6 regulon and Rv3160c-Rv3161c operon. Thioridazine, like other antipsychotics, also inhibits hERG K+ channels, potentially inducing QT prolongation and acts as a functional inhibitor of acid sphingomyelinase (FIASMA).

Product Info

Cas No.

130-61-0

Purity

≥98%

Formula

C21H26N2S2 • HCl

Formula Wt.

407.04

Chemical Name

10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine;hydrochloride

IUPAC Name

10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine; hydrochloride

Synonym

Sonapax hydrochloride, thioridazine chloride

Melting Point

158-160°C

Appearance

White to off white powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

T2936 MSDS PDF

Info Sheet

T2936 Info Sheet PDF

References

Thorsing M, Klitgaard JK, Atilano ML, et al. Thioridazine induces major changes in global gene expression and cell wall composition in methicillin-resistant Staphylococcus aureus USA300. PLoS One. 2013 May 17;8(5):e64518. PMID: 23691239.

Byun HJ, Lee JH, Kim BR, et al. Anti-angiogenic effects of thioridazine involving the FAK-mTOR pathway. Microvasc Res. 2012 Nov;84(3):227-34. PMID: 23022044.

Kang S, Dong SM, Kim BR, et al. Thioridazine induces apoptosis by targeting the PI3K/Akt/mTOR pathway in cervical and endometrial cancer cells. Apoptosis. 2012 Sep;17(9):989-97. PMID: 22460505.

Roth BL, Driscol J. PDSP Ki Database. Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. 2011 Jan.

van Soolingen D, Hernandez-Pando R, Orozco H, et al. The antipsychotic thioridazine shows promising therapeutic activity in a mouse model of multidrug-resistant tuberculosis. PLoS One. 2010 Sep 9;5(9). pii: e12640. PMID: 20844587.

Dutta NK, Mehra S, Kaushal D. A Mycobacterium tuberculosis sigma factor network responds to cell-envelope damage by the promising anti-mycobacterial thioridazine. PLoS One. 2010 Apr 8;5(4):e10069. PMID: 20386700.

Crumb WJ Jr, Ekins S, Sarazan RD, et al. Effects of antipsychotic drugs on I(to), I (Na), I (sus), I (K1), and hERG: QT prolongation, structure activity relationship, and network analysis. Pharm Res. 2006 Jun;23(6):1133-43. PMID: 16715368.

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