10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-phenothiazin

Bezeichnung:10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-phenothiazin

CAS-Nr117-89-5

Englisch Name:Trifluoperazine

CBNumberCB9444115

SummenformelC21H24F3N3S

Molgewicht407.5

MOL-Datei117-89-5.mol

Synonyma

10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-phenothiazin

10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-phenothiazin physikalisch-chemischer Eigenschaften

Schmelzpunkt	232°C
Siedepunkt	bp0.6 202-210°
Dichte	1.2060 (estimate)
storage temp.	Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand	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)
Farbe	White to Off-White
Wasserlöslichkeit	12.23mg/L(24 ºC)
NIST chemische Informationen	Trifluoperazine(117-89-5)

Sicherheit

Giftige Stoffe Daten	117-89-5(Hazardous Substances Data)
Toxizität	LD50 orally in rats, mice: 542.7, 424.0 mg/ml (Fowler)

Trifluoperazine Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Stelazine,SKF,US,1958
Verwenden
10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine is a psychoactive drug.
Verwenden
Antipsychotic.
Verwenden
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.
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
Clinical Use

Schizophrenia and other psychoses
Anxiety
Severe nausea and vomiting
Synthese
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].
Arzneimittelwechselwirkung
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.
Stoffwechsel
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.

Trifluoperazine Upstream-Materialien And Downstream Produkte

10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-phenothiazin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

117-89-5, Trifluoperazine Verwandte Suche:

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