117-89-5 Usage
Originator
Stelazine,SKF,US,1958
Uses
Different sources of media describe the Uses of 117-89-5 differently. You can refer to the following data:
1. Antipsychotic.
2. 10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine is a psychoactive drug.
3. 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.
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
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 117-89-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 117-89:
(5*1)+(4*1)+(3*7)+(2*8)+(1*9)=55
55 % 10 = 5
So 117-89-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H24F3N3S.2ClH/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24;;/h2-3,5-8,15H,4,9-14H2,1H3;2*1H
117-89-5Relevant articles and documents
Kuppuswamy et al.
, p. 652 (1974)
A mechanistic study on the disproportionation and oxidative degradation of phenothiazine derivatives by manganese(III) complexes in phosphate acidic media
Wisniewska, Joanna,Rzesnicki, Pawel,Topolski, Adrian
scheme or table, p. 767 - 774 (2012/07/01)
The oxidative degradation of phenothiazine derivatives (PTZ) by manganese(III) was studied in the presence of a large excess of manganese(III)-pyrophosphate (P2O7 2-), phosphate (PO4 3-), and H+ ions using UV-vis. spectroscopy. The first irreversible step is a fast reaction between phenothiazine and manganese pyrophosphate leading to the complete conversion to a stable phenothiazine radical. In the second step, the cation radical is oxidized by manganese to a dication, which subsequently hydrolyzes to phenothiazine 5-oxide. The reaction rate is controlled by the coordination and stability of manganese(III) ion influenced by the reduction potential of these ions and their strong ability to oxidize many reducing agents. The cation radical might also be transformed to the final product in another competing reaction. The final product, phenothiazine 5-oxide, is also formed via a disproportionation reaction. The kinetics of the second step of the oxidative degradation could be studied in acidic phosphate media due to the large difference in the rates of the first and further processes. Linear dependences of the pseudo-first-order rate constants (k obs) on [Mn III] with a significant non-zero intercept were established for the degradation of phenothiazine radicals. The rate is dependent on [H+] and independent of [PTZ] within the excess concentration range of the manganese(III) complexes used in the isolation method. The kinetics of the disproportionation of the phenothiazine radical have been studied independently from the further oxidative degradation process in acidic sulphate media. The rate is inversely dependent on [PTZ+.], dependent on [H+], and increases slightly with decreasing H+ concentration. Mechanistic consequences of all these results are discussed.
Stability of some phenothiazine free radicals.
Levy,Tozer,Tuck,Loveland
, p. 898 - 905 (2007/10/10)
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