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HomeProduct name listTrifluoperazine

Trifluoperazine

  • CAS NO.:117-89-5
  • Empirical Formula: C21H24F3N3S
  • Molecular Weight: 407.5
  • MDL number: MFCD00242601
  • EINECS: 204-219-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-01 20:20:38
Trifluoperazine Structural

What is Trifluoperazine?

Toxicity

Symptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.

Originator

Stelazine,SKF,US,1958

The Uses of Trifluoperazine

Trifluoperazine is one of the most active antipsychotic drugs. A moderate stimulatory effect accompanies the neuroleptic effect. Trifluoperazine is unique in that, patients instead of the usual stiffness and weakness characteristic of phenothazine derivatives, become more lively. This drug has a strong anticonvulsant activity. It is widely used in psychiatry for treating schizophrenia and other mental illnesses.

The Uses of Trifluoperazine

Antipsychotic.

The Uses of Trifluoperazine

10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine is a psychoactive drug.

Indications

For the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation.

Background

A phenothiazine with actions similar to chlorpromazine. It is used as an antipsychotic and an antiemetic.

Definition

ChEBI: Trifluoperazine is a member of the class of phenothiazines that is phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(4-methylpiperazin-1-yl)propyl group at the N-10 position. It has a role as a dopaminergic antagonist, an antiemetic, an EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor, an EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor, a calmodulin antagonist and a phenothiazine antipsychotic drug. It is a N-alkylpiperazine, a N-methylpiperazine, a member of phenothiazines and an organofluorine compound.

Manufacturing Process

A mixture of 17.2 grams of 2-trifluoromethylphenothiazine, 3.1 grams of sodamide and 14 grams of 1-(3'-chloropropyl)-4-methylpiperazine in 200 ml of xylene is heated at reflux for 2 hours. The salts are extracted into 150 ml of water. The xylene layer is then extracted with several portions of dilute hydrochloric acid. The acid extracts are combined and neutralized with ammonium hydroxide solution. The product, 10-[3'-(4''-methyl-1''- piperazinyl)-propyl]-2-trifluoromethylphenothiazine, is taken into benzene and purified by vacuum distillation, BP 202° to 210°C at 0.6 mm.

Therapeutic Function

Tranquilizer

Pharmacokinetics

Trifluoperazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Trifluoperazine has not been shown effective in the management of behaviorial complications in patients with mental retardation.

Clinical Use


Schizophrenia and other psychoses
Anxiety
Severe nausea and vomiting

Synthesis

Trifluoperazine, 2-trifluoromethyl-10-[3-(4-methyl-1-piperazinyl) propyl]- phenothazine (6.1.5), is synthesized in the manner described above of alkylation using 2- trifluoromethylphenothazin-4-methyl-1-piperazinylpropylchloride [11,17–20].

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
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, e.g. procainamide, disopyramide, dronedarone and amiodarone - avoid with amiodarone and dronedarone.
Antibacterials: increased risk of ventricular arrhythmias with delamanid and moxifloxacin - avoid with moxifloxacin.
Antidepressants: increased level of tricyclics; possibly increased risk of antimuscarinic side effects; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine.
Antiepileptics: antagonism (convulsive threshold lowered).
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: increased risk of ventricular arrhythmias with droperidol and pimozide - avoid; possible increased risk of ventricular arrhythmias with risperidone.
Antivirals: concentration possibly increased with ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid.
Anxiolytics and hypnotics: increased sedative effects.
Atomoxetine: increased risk of ventricular arrhythmias.
Beta-blockers: enhanced hypotensive effect; increased risk of ventricular arrhythmias with sotalol.
Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide.
Diuretics: enhanced hypotensive effect.
Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity.
Pentamidine: increased risk of ventricular arrhythmias.

Metabolism

Hepatic.

Metabolism

Trifluoperazine undergoes extensive first pass metabolism. The major metabolite is the possibly active N-oxide; other metabolites include the sulfoxide and the 7-hydroxy derivative.
Elimination occurs in the bile and urine.

Properties of Trifluoperazine

Melting point: 232°C
Boiling point: bp0.6 202-210°
Density  1.2060 (estimate)
storage temp.  Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility  DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form  Solid
pka pKa 8.05±0.04(H2O t = 20 0.5 I not reported but pKa was stated to be independent of I.) (Uncertain)
color  White to Off-White
Water Solubility  12.23mg/L(24 ºC)
NIST Chemistry Reference Trifluoperazine(117-89-5)

Safety information for Trifluoperazine

Computed Descriptors for Trifluoperazine

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