関: triflupromazine hydrochloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/29 14:11:48」(JST)

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Triflupromazine (Vesprin) is an antipsychotic medication of the phenothiazine class. Among different effects of triflupromazine indication for use of this drug is severe emesis. Due to its potential side effects (triflupromazine has higher risk for side effects than many other antipsychotics) it is not gold standard in antiemetic therapy.

Serious side effects of trifluproamzine can be akathisia and tardive dyskinesia as well as the rare, but potentially fatal, neuroleptic malignant syndrome.

Chemistry[edit]

In an analogous manner to what has already been seen for the preparation of promazine and chlorpromazine, triflupromazine (2-trifluoromethyl-10-(3-dimethylaminopropyl) phenothiazine) is synthesized by the alkylation of 2-trifluoromethylphenothiazine using 3-dimethylaminopropylchloride in the presence of sodamide base.

J. Bernstein, F. Sowinski, DE 1095836 (1956).
G.E. Ullyot, U.S. Patent 2,921,069 (1960).
Smith Kline & French Lab., GB 813861 (1959).
B. Duhm, L. Koester, W. Maul, H. Medenwald, Z. Naturforsch., 13, 756 (1958).
Craig, P.; Nodiff, E.; Lafferty, J.; Ullyot, G. (1957). Journal of Organic Chemistry 22 (6): 709. doi:10.1021/jo01357a618. edit
Yale, Harry L.; Sowinski, Francis; Bernstein, Jack (1957). "10-(3-Dimethylaminopropyl)-2-(Trifluoromethyl)-phenothiazine Hydrochloride (VESPRIN1) and Related Compounds. I". Journal of the American Chemical Society 79: 4375. doi:10.1021/ja01573a037. edit

References[edit]

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English Journal

Phenothiazines solution complexity - Determination of pKa and solubility-pH profiles exhibiting sub-micellar aggregation at 25 and 37°C.

Pobudkowska A1, Ràfols C2, Subirats X2, Bosch E2, Avdeef A3.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2016 Oct 10;93:163-76. doi: 10.1016/j.ejps.2016.07.013. Epub 2016 Jul 21.
PMID 27449396

Diagnosis and surgical management of non-cerebral coenurosis (Taenia gaigeri) in local Black Bengal goat of Tripura: report of six cases.

Monsang SW1, Singh MN2, Kumar M1, Roy J1, Pal SK3, Singh WR3.
Journal of parasitic diseases : official organ of the Indian Society for Parasitology.J Parasit Dis.2016 Sep;40(3):914-8. doi: 10.1007/s12639-014-0604-6. Epub 2014 Oct 30.
PMID 27605809

Sorption of structurally different ionized pharmaceutical and illicit drugs to a mixed-mode coated microsampler.

Peltenburg H1, Timmer N2, Bosman IJ3, Hermens JL2, Droge ST2.
Journal of chromatography. A.J Chromatogr A.2016 May 20;1447:1-8. doi: 10.1016/j.chroma.2016.04.017. Epub 2016 Apr 11.
PMID 27083257

Japanese Journal

紫外・可視微分分光法及び核磁気共鳴法による分光分析学的薬学研究

北村桂介
藥學雜誌 127(10), 1621-1642, 2007-10-01
… A ^<19>F NMR study revealed that triflupromazine binds to BSA and human serum albumin in two regions including Site II with different populations, and that a nonsteroidal anti-inflammatory drug, niflumic acid, binds Sites Ia and Ib. …
NAID 110006402948

Effects of Inorganic Ions on the Binding of Triflupromazine and Chlorpromazine to Bovine Serum Albumin Studied by Spectrometric Methods

KITAMURA Keisuke,OMRAN Ahmed Ahmed,NAGATA Chieyo,KAMIJIMA Yoshiko,TANAKA Rumi,TAKEGAMI Shigehiko,KITADE Tatsuya
Chemical & pharmaceutical bulletin 54(7), 972-976, 2006-07-01
… The effects of inorganic salts, NaCl, NaBr, Nal, Na_2SO_4, KCl, KBr, KI, on the binding constants (Ks) of psychotropic phenothiazine drugs, triflupromazine (TFZ) and chlorpromazine, to bovine serum albumin (BSA) were examined by using second-derivative spectrophotometry. …
NAID 110004836418

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「トリフルプロマジン」

Triflupromazine
Systematic (IUPAC) name
	N,N-dimethyl-3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propan-1-amine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a600010
Pregnancy cat.	?
Legal status	℞-only (US)
Identifiers
CAS number	146-54-3
ATC code	N05AA05
PubChem	CID 5568
IUPHAR ligand	4330
DrugBank	DB00508
ChemSpider	5367
UNII	RO16TQF95Y
KEGG	D00390
ChEMBL	CHEMBL570
Chemical data
Formula	C18H19F3N2S
Mol. mass	352.418 g/mol
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