84-02-6

Basic information

• Product Name: PROCHLORPERAZINE MALEATE
• Synonyms: 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-phenothiazinmaleate(1:2);buccastem;emetiral;enedioate(1:2);meterazinmaleate;nibromina;pasotomin;prochloroproazinehydrogenmaleate
• CAS NO: 84-02-6
• Molecular Formula: 2C₄H₄O₄*C₂₀H₂₄ClN₃S
• Molecular Weight: 606.09
• EINECS: 201-511-3
• Product Categories: Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Antagonists;Dopaminergics;Neurotransmitters
• Mol File: 84-02-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 1750C
• Boiling Point: 524.8 °C at 760 mmHg
• Flash Point: 271.2 °C
• Appearance: Off-White Powder
• Vapor Pressure: 6.76E-32mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: Very slightly soluble in water and in ethanol (96 per cent).
• PKA: pKa 8.1(H2O,t =24±1) (Uncertain)
• Stability: Stable for 2 years as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• Merck: 14,7761
• CAS DataBase Reference: PROCHLORPERAZINE MALEATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROCHLORPERAZINE MALEATE(84-02-6)
• EPA Substance Registry System: PROCHLORPERAZINE MALEATE(84-02-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: SO3150000
• Hazardous Substances Data: 84-02-6(Hazardous Substances Data)

Usage

Description

Prochlorperazine maleate, also known as 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazinemaleate (Compazine), is a member of the piperazine subgroup of phenothiazines. It is characterized by high-milligram antipsychotic potency, a high prevalence of extrapyramidal symptoms (EPS), and low sedative and autonomic effects. Prochlorperazine is more potent on a milligram basis than its alkylamino counterpart, chlorpromazine. Due to the high prevalence of EPS, it is primarily used for its antiemetic effect rather than its antipsychotic effect.

Uses

Used in Pharmaceutical Industry:
Prochlorperazine maleate is used as an antipsychotic agent for its high potency and effectiveness in treating various mental health conditions.
Used in Oncology:
Prochlorperazine maleate is used to increase tumor cell antigen presentation, enhancing the efficacy of anti-tumor monoclonal antibodies (mAbs) in cancer treatment.
Used in Migraine Treatment:
Prochlorperazine maleate is used as an antimigraine agent, helping to alleviate the symptoms and frequency of migraine headaches.
Used in Antiemetic Therapy:
Prochlorperazine maleate is used as an antiemetic agent, primarily due to its high potency and effectiveness in preventing and treating nausea and vomiting.

Biological Activity

D 2 receptor antagonist. Also interacts with 5-HT 3 and nAChR. Displays antipsychotic, antispasmodic, antiemetic and antinociceptive activity in vivo .

Biochem/physiol Actions

Phenothiazine antipsychotic; D2 dopamine receptor antagonist; antispasmodic

References

References/Citations 1) Daniel?et al.?(2015),?Phenothiazine-derived antipsychotic drugs inhibit dynamin and clathrin-mediated endocytosis; Traffic,?16?635 2) Chew?et al.?(2020),?Endocytosis Inhibition in Humans to Improve Responses to ADCC-Mediating Antibodies; Cell,?180?895 3) Hollister?et al.?(1969),?Clinical use of psychotherapeutic drugs: current status;?Clin. Pharmacol. Ther.,?10?170 4) Cook and Newberry (2018),?Emergency Department Use of Intravenous Prochlorperazine for Acute Migraine; Adv. Emerg. Nurs. J.,?40?148 5) Van den Berg?et al.?(1996),?The prophylactic antiemetic efficacy of prochlorperazine and ondansetron in nasal septal surgery: a randomized double-blind comparison; Anaesth. Intensive Care,?24?538

InChI:InChI=1/C20H24ClN3S.2C4H4O4/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24;2*5-3(6)1-2-4(7)8/h2-3,5-8,15H,4,9-14H2,1H3;2*1-2H,(H,5,6)(H,7,8)