53772-83-1

Basic information

• Product Name: Zuclopenthixol
• Synonyms: Zuclopenthixol;4-[3-[(9Z)-2-Chloro-9H-thioxanthene-9-ylidene]propyl]-1-piperazineethanol;4-[3-[(Z)-2-Chloro-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol;cis-Clopenthixol;(Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol;Clopentixol cis-(Z)-;Clopixol;Einecs 258-758-5
• CAS NO: 53772-83-1
• Molecular Formula: C22H25ClN2OS
• Molecular Weight: 400.137612
• EINECS: 258-758-5
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 53772-83-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 56-60°C
• Boiling Point: 577.4 °C at 760 mmHg
• Flash Point: 303 °C
• Appearance: /
• Density: 1.289 g/cm³
• Vapor Pressure: 3.56E-14mmHg at 25°C
• Refractive Index: 1.675
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.96±0.10(Predicted)
• CAS DataBase Reference: Zuclopenthixol(CAS DataBase Reference)
• NIST Chemistry Reference: Zuclopenthixol(53772-83-1)
• EPA Substance Registry System: Zuclopenthixol(53772-83-1)

Safety Data

• Hazardous Substances Data: 53772-83-1(Hazardous Substances Data)

Usage

Description

Zuclopenthixol, also known as the (Z)-isomer of clopenthixol, is a thioxanthene-based neuroleptic and a potent dopamine receptor antagonist. It exhibits its antipsychotic effects by antagonizing D1 and D2 dopamine receptors, as well as serotonin (5-HT) receptor subtypes 5-HT2 and 5-HT6, α1-adrenergic, and histamine receptors. Zuclopenthixol is characterized by its pale yellow, low melting solid appearance and is used in various formulations, including zuclopenthixol decanoate, zuclopenthixol acetate, and zuclopenthixol dihydrochloride.

Uses

Used in Pharmaceutical Industry:
Zuclopenthixol is used as an antipsychotic agent for the treatment of schizophrenia and bipolar mania. It works by antagonizing D1 and D2 dopamine receptors, which helps in managing the symptoms of these mental health disorders.
Additionally, Zuclopenthixol is used as an inhibitor of coxsackievirus B3, demonstrating its potential application in the field of virology and infectious diseases.
Furthermore, Zuclopenthixol serves as an intermediate in the synthesis of Zuclopenthixol Decanoate (Z701490), which is utilized in the maintenance treatment of chronic schizophrenic patients. This highlights its importance in the development of long-acting antipsychotic medications for better patient compliance and management of chronic conditions.

Clinical Use

Antipsychotic for schizophrenia and other psychoses

Drug interactions

Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effects. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; increased risk of ventricular arrhythmias with methadone. Anti-arrhythmics: increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval - avoid with amiodarone and disopyramide. Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin and parenteral erythromycin - avoid Antidepressants: increased level of tricyclics; possible increased risk of convulsions with vortioxetine. Antiepileptics: anticonvulsant effect antagonised. Antimalarials: avoid concomitant use with artemether/lumefantrine. Antipsychotics: avoid concomitant use of clozapine with depot preparations in case of neutropenia; possible increased risk of ventricular arrhythmias with risperidone. Antivirals: concentration possibly increased with ritonavir. Atomoxetine: increased risk of ventricular arrhythmias. Anxiolytics and hypnotics: increased sedative effects. Beta-blockers: increased risk of ventricular arrhythmias with sotalol - avoid. Cytotoxics: increased risk of ventricular arrhythmias with vandetanib - avoid; increased risk of ventricular arrhythmias with arsenic trioxide.

Metabolism

Metabolism of zuclopenthixol is by sulphoxidation, sidechain N-dealkylation and glucuronic acid conjugation. The sulphoxide metabolites are mainly excreted in the urine while unchanged drug and the dealkylated form tend to be excreted in the faeces.

References

https://www.drugbank.ca/drugs/DB01624 https://en.wikipedia.org/wiki/Tiabendazole

InChI:InChI=1/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5-

Upstream product

• 77278-40-1 tert-butyl 4-(benzoyloxy)piperazine-1-carboxylate 
• 86-39-5 2-Chlorothioxanthone 
• 463-49-0 1,2-propanediene 
• 540-51-2 2-bromoethanol 

Downstream Products

• 85721-05-7 zuclopenthixol acetate 

Relevant articles and documents

Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct

Allene (C3H4) gas is produced and separated on million-metric-ton scale per year during petroleum refining but is rarely employed in organic synthesis. Meanwhile, the addition of an allyl group (C3H5) to ketones is among the most common and prototypical reactions in synthetic chemistry. Herein, we report that the combination of allene gas with inexpensive and environmentally benign hydrosilanes, such as PMHS, can serve as a replacement for stoichiometric quantities of allylmetal reagents, which are required in most enantioselective ketone allylation reactions. This process is catalyzed by copper salts and commercially available ligands, operates without specialized equipment or pressurization, and tolerates a broad range of functional groups. Furthermore, the exceptional chemoselectivity of this catalyst system enables industrially relevant C3 hydrocarbon mixtures of allene with methylacetylene and propylene to be applied directly.