114488-10-7

Basic information

• Product Name: (S)-Thioridazine
• Synonyms: (S)-(-)-Thioridazine;(S)-Thioridazine;10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-, (S)-;10H-Phenothiazine, 10-[2-[(2S)-1-methyl-2-piperidinyl]ethyl]-2-(methylthio)- (9CI)
• CAS NO: 114488-10-7
• Molecular Formula: C₂₁H₂₆N₂S₂
• Molecular Weight: 370.57
• EINECS: 200-044-2
• Mol File: 114488-10-7.mol

Chemical Properties

• Boiling Point: 515.7°C at 760 mmHg
• Flash Point: 265.7°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 9.65E-11mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: (S)-Thioridazine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Thioridazine(114488-10-7)
• EPA Substance Registry System: (S)-Thioridazine(114488-10-7)

Safety Data

• Hazardous Substances Data: 114488-10-7(Hazardous Substances Data)

Usage

Uses

Used in Psychiatry:
(S)-Thioridazine is used as an antipsychotic agent for the treatment of psychiatric disorders, particularly schizophrenia. It helps in restoring the balance of neurotransmitters and alleviating symptoms associated with psychosis.
Used in Neurotransmitter Regulation:
(S)-Thioridazine is used as a receptor antagonist to regulate the levels of dopamine and serotonin in the brain, which contributes to the mitigation of psychotic symptoms.
Used in Cardiac Monitoring:
Due to the risk of cardiac arrhythmias and cardiovascular complications associated with (S)-Thioridazine, it is also used as a reference point for monitoring and managing potential side effects in patients undergoing treatment with this medication.
Used in Ophthalmological Supervision:
Given the potential for retinopathy and vision impairment with long-term use, (S)-Thioridazine necessitates regular ophthalmological assessment and supervision to ensure patient safety and minimize the risk of adverse effects on vision.

InChI:InChI=1/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

Upstream product

• 16463-38-0 potassium 2-chlorobenzoate 
• 18902-93-7 N-(3'-methylthiophenyl)anthranylic acid 
• 101895-74-3 2-benzylsulfanyl-10H-phenothiazine 
• 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 
• 2557-78-0 2-fluorothiophenol 
• 1199-36-6 1-chloro-4-(methylthio)-2-nitrobenzene 
• 129846-85-1 N-(2-(1-methyl-2-piperidynyl)ethyl)-2-(2-fluorophenylthio)-5-(methylthio)aniline 

Downstream Products

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

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.

THE (S)-ENANTIOMER OF MEPAZINE

The present invention relates to the (S)-enantiomer of mepazine, its applicability in therapy, a pharmacological composition comprising (S)-mepazine, and processes for the preparation of (S)- mepazine and one of its intermediates.

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.

MODIFIED SYNTHESES OF 2-(METHYLTHIO)-10-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)PHENOTHIAZINE (THIORIDAZINE) AND 1-(3-(2-(METHYLSULFONYL)-10-PHENOTHIAZINYL)PROPYL)-PIPERIDINE-4-CARBOXAMIDE (METOPIMAZINE)

Modified syntheses