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a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/24 11:09:25」(JST)

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Trifluoperazine (Eskazinyl, Eskazine, Jatroneural, Modalina, Stelazine, Terfluzine, Trifluoperaz, Triftazin) is a typical antipsychotic of the phenothiazine chemical class.

Uses[edit]

The primary application of trifluoperazine is for schizophrenia. Other official indications may vary country by country, but generally it is also indicated for use in agitation and patients with behavioural problems, severe nausea and vomiting as well as severe anxiety. Trials have shown a moderate benefit of this drug in patients with boderline personality disorder.^[1] Its use in many parts of the world has declined because of highly frequent and severe early and late tardive dyskinesia, a type of extrapyramidal symptom. The annual development rate of tardive dyskinesia may be as high as 4%.^{[citation needed]}

A 2005 study of patients with generalized anxiety disorder ^[2] noted that:

“

The results of a randomized placebo-controlled, flexible-dose acute treatment study indicate that the antipsychotic drug trifluoperazine had superior efficacy from the first week of double-blind treatment, although there were markedly more treatment emergent adverse events with trifluoperazine (62%,compared to 46% with placebo)

”

A 2006 study suggested that trifluoperazine may be able to reverse addiction to opioids.^[3]

A multi-year UK study by the Alzheimer's Research Trust suggested that this and other antipsychotic drugs commonly given to Alzheimer's patients with mild behavioural problems often make their condition worse.^[4] The study concluded that

“

For most patients with AD, withdrawal of neuroleptics had no overall detrimental effect on functional and cognitive status and by some measures improved functional and cognitive status. Neuroleptics may have some value in the maintenance treatment of more severe neuropsychiatric symptoms, but this possibility must be weighed against the unwanted effects of therapy. The current study helps to inform a clinical management strategy for current practice, but the considerable risks of maintenance therapy highlight the urgency of further work to find, develop, and implement safer and more effective treatment approaches for neuropsychiatric symptoms in people with AD.

”

Pharmacology[edit]

Trifluoperazine has central antiadrenergic,^[5] antidopaminergic,^[6]^[7] and minimal anticholinergic effects.^[8] It is believed to work by blockading dopamine D₁ and D₂ receptors in the mesocortical and mesolimbic pathways, relieving or minimizing such symptoms of schizophrenia as hallucinations, delusions, and disorganized thought and speech.^[9]

Side effects[edit]

A 2004 meta-analysis of the studies on trifluoperazine found that it is more likely than placebo to cause extrapyramidal side effects such as akathisia, dystonia, and Parkinsonism.^[9] It is also more likely to cause somnolence and anticholinergic side effects such as red eye and xerostomia (dry mouth).^[9] All antipsychotics can cause the rare and sometimes fatal neuroleptic malignant syndrome.^[10] Trifluoperazine can lower the seizure threshold.^[11] The antimuscarinic action of trifluoperazine can cause excessive dilation of the pupils (mydriasis), which increases the chances of patients with hyperopia developing glaucoma.^[12]

Contraindications[edit]

Trifluoperazine is contraindicated in CNS depression, coma, and blood dyscrasias. Trifluoperazine should be used with caution in patients suffering from renal or hepatic impairment.

Formulations[edit]

In the United Kingdom and some other countries, Trifluoperazine is sold and marketed under the brand 'Stelazine'.

The drug is sold as tablet, liquid and 'Trifluoperazine-injectable USP' for deep intramuscular short-term use.

In the past, trifluoperazine was used in fixed combinations with the MAO inhibitor (antidepressant) tranylcypromine to attenuate the strong stimulating effects of this antidepressant. This combination was sold under the brand name Jatrosom N. Likewise a combination with amobarbital (potent sedative/hypnotic agent) for the amelioration of psychoneurosis and insomnia existed under the brand name Jalonac. In Italy the first combination is still available, sold under the brand name Parmodalin (10 mg of Tranylcypromine and 1 mg of Trifluoperazine).

Chemistry[edit]

Trifluoperazine (2-trifluoromethyl-10-[3-(4-methyl-1-piperazinyl)propyl]phenothazine) is synthesized in the manner described already for prochlorperazine, alkylation is performed using 2-trifluoromethylphenothazin-4-methyl-1-piperazinylpropylchloride as the substrate.

Craig, P.; Nodiff, E.; Lafferty, J.; Ullyot, G. (1957). Journal of Organic Chemistry 22 (6): 709. doi:10.1021/jo01357a618. edit
G.E. Ullyot, U.S. Patent 2,921,069 (1960).
Sharma, H.; Banerjee, S.; Sharma, V.; Mital, R. (1968). "Phenothiazines Exhibiting Lesser Extraparamidal Manifestations". Journal of Medicinal Chemistry 11 (6): 1244. doi:10.1021/jm00312a600. PMID 5680054. edit
P.N. Craig, G.E. Ullyot, DE 1165034 (1956).
B.H. Chung, F. Zimalkowski, Arch. Pharm., 317, 323 (1984).

References[edit]

^ Rex William Cowdry, David L. Gardner (1988). "Pharmacotherapy of Borderline Personality DisorderAlprazolam, Carbamazepine, Trifluoperazine, and Tranylcypromine". Arch Gen Psychiatry 45 (2): 111–119. doi:10.1001/archpsyc.1988.01800260015002.
^ David S. Baldwin, Polkinghorn (2005). "Evidence-based pharmacotherapy of generalized anxiety disorder". International Journal of Neuropsychopharmacology 8: 293–302. doi:10.1017/S1461145704004870.
^ Tang L, Shukla PK, Wang ZJ (2006). "Trifluoperazine, an orally available clinically used drug, disrupts opioid antinociceptive tolerance". Neuroscience Letters 397 (1–2): 1–4. doi:10.1016/j.neulet.2005.11.050. PMID 16380209. Lay summary – ScienceDaily (2006-02-13).
^ Ballard C, Lana MM, Theodoulou M, et al. (April 2008). "A Randomised, Blinded, Placebo-Controlled Trial in Dementia Patients Continuing or Stopping Neuroleptics (The DART-AD Trial)". In Brayne, Carol. PLoS Medicine 5 (4): e76. doi:10.1371/journal.pmed.0050076. PMC 2276521. PMID 18384230. Lay summary – BBC News (2008-04-01). "Neuroleptics provided no benefit for patients with mild behavioural problems, but were associated with a marked deterioration in verbal skills" Cite uses deprecated parameters (help)
^ Huerta-Bahena J, Villalobos-Molina R, García-Sáinz JA (January 1983). "Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects". Molecular Pharmacology 23 (1): 67–70. PMID 6135146. Retrieved 2009-06-21. Cite uses deprecated parameters (help)
^ Seeman P, Lee T, Chau-Wong M, Wong K (June 1976). "Antipsychotic drug doses and neuroleptic/dopamine receptors". Nature 261 (5562): 717–9. Bibcode:1976Natur.261..717S. doi:10.1038/261717a0. PMID 945467. Cite uses deprecated parameters (help)
^ Creese I, Burt DR, Snyder SH (1996). "Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs". The Journal of Neuropsychiatry and Clinical Neurosciences 8 (2): 223–6. PMID 9081563. Retrieved 2009-06-21.
^ Ebadi, Manuchair S (1998). "Trifluoperazine Hydrochloride". CRC desk reference of clinical pharmacology (illustrated ed.). CRC Press. ISBN 978-0-8493-9683-0. Retrieved 2009-06-21.
^ ^a ^b ^c Marques LO, Lima MS, Soares BG (2004). "Trifluoperazine for schizophrenia". In Marques, Luciana de Oliveira. Cochrane Database of Systematic Reviews (Online) (1): CD003545. doi:10.1002/14651858.CD003545.pub2. PMID 14974020.
^ Smego RA, Durack DT (June 1982). "The neuroleptic malignant syndrome". Archives of Internal Medicine 142 (6): 1183–5. doi:10.1001/archinte.142.6.1183. PMID 6124221. Cite uses deprecated parameters (help)
^ Hedges D, Jeppson K, Whitehead P (July 2003). "Antipsychotic medication and seizures: a review". Drugs of Today (Barcelona, Spain : 1998) 39 (7): 551–7. doi:10.1358/dot.2003.39.7.799445. PMID 12973403. Cite uses deprecated parameters (help)
^ Boet DJ (July 1970). "Toxic effects of phenothiazines on the eye". Documenta Ophthalmologica. Advances in Ophthalmology 28 (1): 1–69. doi:10.1007/BF00153873. PMID 5312274. Cite uses deprecated parameters (help)

External links[edit]

Trifluoperazine bound to proteins in the PDB

UpToDate Contents

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English Journal

The Polymorphic Variant P24T of UDP-Glucuronosyltransferase 1A4 and Its Unusual Consequences.

Troberg J1, Finel M2.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2015 Nov;43(11):1769-72. doi: 10.1124/dmd.115.065680. Epub 2015 Sep 1.
The P24T polymorphic variant of the human UDP-glucuronosyltransferase 1A4 (UGT1A4*2, 70C>A) occurs within the signal peptide, five amino acids upstream of the cleavage site and the start of the mature protein. Bioinformatic analysis of the variant suggested that the signal peptide of part of the
PMID 26329791

In vitro antifungal activity of antipsychotic drugs and their combinations with conventional antifungals against Scedosporium and Pseudallescheria isolates.

Homa M1, Galgóczy L2, Tóth E1, Tóth L1, Papp T3, Chandrasekaran M3, Kadaikunnan S3, Alharbi NS3, Vágvölgyi C4.
Medical mycology.Med Mycol.2015 Nov 1;53(8):890-5. doi: 10.1093/mmy/myv064. Epub 2015 Aug 26.
In the present study, in vitro antifungal activities of five antipsychotic drugs (i.e., chlorpromazine hydrochloride, CPZ; trifluoperazine hydrochloride, TPZ; amantadine hydrochloride; R-(-)-deprenyl hydrochloride, and valproic acid sodium salt) and five conventional antifungal drugs (i.e., amphoter
PMID 26316212

Reversal of pathological features of Graves' Orbitopathy by activation of Forkhead transcription factors, FOXOs.

Zhang L1, Ji QH2, Ruge F1, Lane C3, Morris D3, Tee AR1, Dayan CM1, Ludgate M1.
The Journal of clinical endocrinology and metabolism.J Clin Endocrinol Metab.2015 Oct 26:jc20152932. [Epub ahead of print]
CONTEXT: Graves' Orbitopathy (GO) is a disfiguring/distressing, inflammatory autoimmune condition. This intractable problem is caused by expansion of the orbital contents around the eye by excessive fat generation (adipogenesis) and overproduction of extracellular matrix components, especially hyalu
PMID 26502358

Japanese Journal

Potentiometric Sensors for the Determination of Trifluoperazine Hydrochloride in Pharmaceutical Preparations

Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 25(11), 1295-1299, 2009-11-10
NAID 10026779843

Potentiometric Sensors for the Determination of Trifluoperazine Hydrochloride in Pharmaceutical Preparations

Analytical Sciences 25(11), 1295-1299, 2009
NAID 130004441776

A Simple and Rapid Spectrophotometric Determination of Thallium(III) with Trifluoperazine Hydrochloride

Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 18(10), 1131-1135, 2002-10-10
NAID 10011310712

Related Pictures

★リンクテーブル★

リンク元	「トリフロペラジン」「trifluoperazine maleate」
関連記事	「hydrochloride」

「トリフロペラジン」

Trifluoperazine
Systematic (IUPAC) name
	10-[3-(4-methylpiperazin-1-yl)propyl]-; 2-(trifluoromethyl)-10H-phenothiazine
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682121
Pregnancy cat.	C (AU) C (US)
Legal status	POM (UK) ℞-only (US)
Routes	oral, IM
Pharmacokinetic data
Metabolism	Hepatic
Half-life	10–20 hours
Identifiers
CAS number	117-89-5
ATC code	N05AB06
PubChem	CID 5566
IUPHAR ligand	214
DrugBank	DB00831
ChemSpider	5365
UNII	214IZI85K3
ChEBI	CHEBI:45951
ChEMBL	CHEMBL422
Chemical data
Formula	C21H24F3N3S
Mol. mass	407.497
	SMILES FC(F)(F)c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(C)CC4;
	InChI InChI=1S/C21H24F3N3S/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 ; Key:ZEWQUBUPAILYHI-UHFFFAOYSA-N ;
(what is this?) (verify)

　　[★]

英: trifluoperazine TFP
化: マレイン酸トリフロペラジン trifluoperazine maleate、trifluoperazine hydrochloride
商: トリフロペラジン、Stelazine

向精神薬

抗精神病薬

フェノチアジン系

「trifluoperazine maleate」

　　[★]

マレイン酸トリフロペラジン

関: TFP、trifluoperazine、trifluoperazine hydrochloride

「hydrochloride」

　　[★] 塩酸塩、ハイドロクロライド　

[1] Rex William Cowdry, David L. Gardner (1988). "Pharmacotherapy of Borderline Personality DisorderAlprazolam, Carbamazepine, Trifluoperazine, and Tranylcypromine". Arch Gen Psychiatry 45 (2): 111–119. doi:10.1001/archpsyc.1988.01800260015002.

[2] David S. Baldwin, Polkinghorn (2005). "Evidence-based pharmacotherapy of generalized anxiety disorder". International Journal of Neuropsychopharmacology 8: 293–302. doi:10.1017/S1461145704004870.

[3] Tang L, Shukla PK, Wang ZJ (2006). "Trifluoperazine, an orally available clinically used drug, disrupts opioid antinociceptive tolerance". Neuroscience Letters 397 (1–2): 1–4. doi:10.1016/j.neulet.2005.11.050. PMID 16380209. Lay summary – ScienceDaily (2006-02-13).

[4] Ballard C, Lana MM, Theodoulou M, et al. (April 2008). "A Randomised, Blinded, Placebo-Controlled Trial in Dementia Patients Continuing or Stopping Neuroleptics (The DART-AD Trial)". In Brayne, Carol. PLoS Medicine 5 (4): e76. doi:10.1371/journal.pmed.0050076. PMC 2276521. PMID 18384230. Lay summary – BBC News (2008-04-01). "Neuroleptics provided no benefit for patients with mild behavioural problems, but were associated with a marked deterioration in verbal skills" Cite uses deprecated parameters (help)

[5] Huerta-Bahena J, Villalobos-Molina R, García-Sáinz JA (January 1983). "Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects". Molecular Pharmacology 23 (1): 67–70. PMID 6135146. Retrieved 2009-06-21. Cite uses deprecated parameters (help)

[6] Seeman P, Lee T, Chau-Wong M, Wong K (June 1976). "Antipsychotic drug doses and neuroleptic/dopamine receptors". Nature 261 (5562): 717–9. Bibcode:1976Natur.261..717S. doi:10.1038/261717a0. PMID 945467. Cite uses deprecated parameters (help)

[7] Creese I, Burt DR, Snyder SH (1996). "Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs". The Journal of Neuropsychiatry and Clinical Neurosciences 8 (2): 223–6. PMID 9081563. Retrieved 2009-06-21.

[8] Ebadi, Manuchair S (1998). "Trifluoperazine Hydrochloride". CRC desk reference of clinical pharmacology (illustrated ed.). CRC Press. ISBN 978-0-8493-9683-0. Retrieved 2009-06-21.

[Marq-9] Marques LO, Lima MS, Soares BG (2004). "Trifluoperazine for schizophrenia". In Marques, Luciana de Oliveira. Cochrane Database of Systematic Reviews (Online) (1): CD003545. doi:10.1002/14651858.CD003545.pub2. PMID 14974020.

[10] Smego RA, Durack DT (June 1982). "The neuroleptic malignant syndrome". Archives of Internal Medicine 142 (6): 1183–5. doi:10.1001/archinte.142.6.1183. PMID 6124221. Cite uses deprecated parameters (help)

[11] Hedges D, Jeppson K, Whitehead P (July 2003). "Antipsychotic medication and seizures: a review". Drugs of Today (Barcelona, Spain : 1998) 39 (7): 551–7. doi:10.1358/dot.2003.39.7.799445. PMID 12973403. Cite uses deprecated parameters (help)

[12] Boet DJ (July 1970). "Toxic effects of phenothiazines on the eye". Documenta Ophthalmologica. Advances in Ophthalmology 28 (1): 1–69. doi:10.1007/BF00153873. PMID 5312274. Cite uses deprecated parameters (help)

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trifluoperazine hydrochloride