52496-67-0

Basic information

• Product Name: (R)-Thioridazine
• Synonyms: (R)-(+)-Thioridazine;(R)-Thioridazine;10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-, (R)-;10H-Phenothiazine, 10-[2-[(2R)-1-methyl-2-piperidinyl]ethyl]-2-(methylthio)- (9CI)
• CAS NO: 52496-67-0
• Molecular Formula: C₂₁H₂₆N₂S₂
• Molecular Weight: 370.57
• Mol File: 52496-67-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-Thioridazine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Thioridazine(52496-67-0)
• EPA Substance Registry System: (R)-Thioridazine(52496-67-0)

Safety Data

• Hazardous Substances Data: 52496-67-0(Hazardous Substances Data)

Usage

Description

(R)-Thioridazine, the active enantiomer of the phenothiazine antipsychotic drug, is a chemical compound that functions as a dopamine antagonist. It is primarily used in the treatment of psychiatric disorders such as schizophrenia and bipolar disorder by blocking dopamine receptors in the brain, thereby alleviating symptoms of psychosis and stabilizing moods. Despite its effectiveness, the use of (R)-Thioridazine has declined due to its association with severe side effects like cardiotoxicity and neurological impairment, leading to the preference for safer and more effective antipsychotic medications.

Uses

Used in Pharmaceutical Industry:
(R)-Thioridazine is used as an antipsychotic medication for the treatment of psychiatric disorders such as schizophrenia and bipolar disorder. It is employed for its ability to block dopamine receptors in the brain, which helps in reducing psychotic symptoms and stabilizing moods.
However, due to the potential for severe side effects, its use has been largely replaced by safer and more effective antipsychotic medications in recent years. Despite this, research into the compound's mechanism of action and potential applications in other areas of medicine may still be ongoing.

Upstream product

• 129846-85-1 N-(2-(1-methyl-2-piperidynyl)ethyl)-2-(2-fluorophenylthio)-5-(methylthio)aniline 
• 1199-36-6 1-chloro-4-(methylthio)-2-nitrobenzene 
• 2557-78-0 2-fluorothiophenol 
• 16463-38-0 potassium 2-chlorobenzoate 
• 1783-81-9 3-methylmercaptoaniline 
• 99970-41-9 10H-phenothiazine-2-thiol 
• 13313-45-6 N-(3-methylthiophenyl)phenylamine 
• 7643-08-5 2-(methylthio)-10H-phenothiazine 
• 32672-69-8 mesoridazine besylate 
• 129846-82-8 2-(2-fluorophenylthio)-5-(methylthio)nitrobenzene 
• 129846-83-9 2-(2-fluorophenylthio)-5-(methylthio)aniline 
• 18902-93-7 N-(3'-methylthiophenyl)anthranylic acid 
• 101895-74-3 2-benzylsulfanyl-10H-phenothiazine 

Downstream Products

• 5588-33-0 mesoridazine 
• 7776-05-8 Thioridazine 5-sulfoxide 
• 103827-30-1 N-Oxide thioridazine 
• 130-61-0 thioridazine Hydrochloride 
• 10538-32-6 Northioridazine 
• 14759-06-9 sulforidazine 

Relevant articles and documents

Combination of experimental and in silico methods for the assessment of the phototransformation products of the antipsychotic drug/metabolite Mesoridazine

The lack of studies on the fate and effects of drug metabolites in the environment is of concern. As their parent compounds, metabolites enter the aquatic environment and are subject to biotic and abiotic process. In this regard, photolysis plays an important role. This study combined experimental and in silico quantitative structure-activity relationship (QSAR) methods to assess the fate and effects of Mesoridazine (MESO), a pharmacologically active human drug and metabolite of the antipsychotic agent Thioridazine, and its transformation products (TPs) formed through a Xenon lamp irradiation. After 256 min, the photodegradation of MESO ? besylate (50 mg L? 1) achieved 90.4% and 6.9% of primary elimination and mineralization, respectively. The photon flux emitted by the lamp (200–600 nm) was 169.55 J cm? 2. Sixteen TPs were detected by means of liquid chromatography-high resolution mass spectrometry (LC-HRMS), and the structures were proposed based on MSn fragmentation patterns. The main transformation reactions were sulfoxidation, hydroxylation, dehydrogenation, and sulfoxide elimination. A back-transformation of MESO to Thioridazine was evidenced. Aerobic biodegradation tests (OECD 301 D and 301F) were applied to MESO and the mixture of TPs present after 256 min of photolysis. Most of TPs were not biodegraded, demonstrating their tendency to persist in aquatic environments. The ecotoxicity towards Vibrio fischeri showed a decrease in toxicity during the photolysis process. The in silico QSAR tools QSARINS and US-EPA PBT profiler were applied for the screening of TPs with character of persistence, bioaccumulation, and toxicity (PBT). They have revealed the carbazole derivatives TP 355 and TP 337 as PBT/vPvB (very persistent and very bioaccumulative) compounds. In silico QSAR predictions for mutagenicity and genotoxicity provided by CASE Ultra and Leadscope indicated positive alerts for mutagenicity on TP 355 and TP 337. Further studies regarding the carbazole derivative TPs should be considered to confirm their hazardous character.

Anti-proliferative drugs

The present invention relates to methods for the treatment of diseases associated with hyper-proliferation of cells by administering to a subject in need a therapeutically effective amount of at least one psychotropic agent. Specific proliferative diseases against which psychotropic agents were found to be effective are cancer, including multi-drug resistant cancer and diseases associated with hyper-proliferation of the skin cells, such as psoriasis and hyperkeratosis.