WordNet

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）』「2014/07/24 22:49:29」(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

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

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English Journal

Solubility and pKa determination of six structurally related phenothiazines.

Domańska U, Pelczarska A, Pobudkowska A.SourceDepartment of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland. ula@ch.pw.edu.pl
International journal of pharmaceutics.Int J Pharm.2011 Dec 12;421(1):135-44. doi: 10.1016/j.ijpharm.2011.09.040. Epub 2011 Oct 1.
Solubilities of six structurally related phenothiazines, namely chlorpromazine hydrochloride, fluphenazine dihydrochloride, promazine hydrochloride, thioridazine hydrochloride, trifluoperazine dihydrochloride, and triflupromazine hydrochloride at constant pH were measured in the temperature range fr
PMID 21983455

19F NMR spectroscopic study on the binding of triflupromazine to bovine and human serum albumins.

Kitamura K, Kume M, Yamamoto M, Takegami S, Kitade T.SourceKyoto Pharmaceutical University, 5 Nakauchicho, Misasagi, Yamashina-ku, Kyoto 607-8414, Japan. kitamura@mb.kyoto-phu.ac.jp
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2004 Oct 29;36(2):411-4.
The 19F NMR spectrum of triflupromazine hydrochloride (TFZ) in a buffer solution (pH 6.8) showed a single sharp signal of the TFZ CF3 group at 13.5 ppm from the external trifluoroacetic acid. The addition of 1 mM HSA or BSA to the sample solution caused a split of the CF3 signal into two broadened s
PMID 15496337

Haemodynamic and blood gas changes in buffaloes (Bubalus bubalis) in the supine position following thiopentone anaesthesia with premedication.

Peshin PK, Krishnamurthy D, Singh K, Nassimi MN, Nigam JM.AbstractStudies were undertaken on seven adult female buffaloes (Bubalus bubalis) premedicated with triflupromazine hydrochloride (0.3 mg/kg) and chloral hydrate (30 mg/kg). Anaesthesia was induced with thiopentone sodium (10 mg/kg) and animals were kept under intermittent positive pressure ventilation. Measurements were made for 30 min in the lateral position, for 20 min in the supine position and subsequently for 40 min again in the lateral position. Regurgitation during anaesthesia was avoided by evacuation of the rumen by rumenotomy two days prior to the experiment. When animals were in the lateral position there were minimal changes in arterial pressure and heart rate but central venous pressure rose. These changes were related to intermittent positive pressure ventilation. In the supine position, increase in heart rate (28%) was associated with profound hypotension (56%) and decrease in central venous pressure (171%) in these animals. There was a fall in venous oxygen tension and a marked increase (91%) in oxygen extraction ratio. Restoration to the lateral position ameliorated all these changes rapidly. It was suggested that a 'low pressure-low flow' circulatory state exists in anaesthetised adult buffaloes in the supine position.
Veterinary research communications.Vet Res Commun.1987;11(1):1-7.
Studies were undertaken on seven adult female buffaloes (Bubalus bubalis) premedicated with triflupromazine hydrochloride (0.3 mg/kg) and chloral hydrate (30 mg/kg). Anaesthesia was induced with thiopentone sodium (10 mg/kg) and animals were kept under intermittent positive pressure ventilation. Mea
PMID 3576966

Japanese Journal

Permeation of Drugs through Chitosan Membranes

沢柳洋市,南部直樹,永井恒司
Chemical & pharmaceutical bulletin 30(9), 3297-3301, 1982-09-25
… The permeation of several drugs such as promethazine hydrochloride, chlorpromazine hydrochloride, diethazine hydrochloride, triflupromazine hydrochloride, flufenamic acid, ketoprofen, indomethacin, and tolbutamide through a chitosan membrane was investigated as part of a series of studies on pharmaceutical applications of chitin and chitosan. …
NAID 110003634757

Interaction of Phenothiazines with Pectin in Aqueous Solution

高橋靖侑,南部直樹,永井恒司
Chemical & pharmaceutical bulletin 29(3), 828-833, 1981-03-25
… Scatchard plots were not linear for water-soluble drugs such as promazine hydrochloride, triflupromazine hydrochloride, and so on, and thus the number of binding sites of pectin was considered to be more than two. …
NAID 110003633738

Related Pictures

★リンクテーブル★

リンク元	「トリフルプロマジン」「塩酸トリフルプロマジン」
関連記事	「triflupromazine」「hydrochloride」

「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
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
ChEBI	CHEBI:9711
ChEMBL	CHEMBL570
Chemical data
Formula	C18H19F3N2S
Mol. mass	352.418 g/mol
	SMILES CN(C)CCCN1c2ccccc2Sc2ccc(cc12)C(F)(F)F;
	InChI InChI=1S/C18H19F3N2S/c1-22(2)10-5-11-23-14-6-3-4-7-16(14)24-17-9-8-13(12-15(17)23)18(19,20)21/h3-4,6-9,12H,5,10-11H2,1-2H3 ; Key:XSCGXQMFQXDFCW-UHFFFAOYSA-N ;
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