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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/15 17:24:12」(JST)

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Promazine (Sparine) is a medication that belongs to the phenothiazine class of antipsychotics. An older medication used to treat schizophrenia, it is still prescribed, alongside newer agents such as olanzapine and quetiapine. It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon either.

Promazine is not approved for human use in the United States. It is available in the US for veterinary use under the names Promazine and Tranquazine.

Chemistry

Promazine, 10-(3-dimethylaminopropyl)phenothiazine, is prepared by the alkylation of phenothiazine with 3-dimethylaminopropylchloride in the presence of sodamide.

P. Charpentier, U.S. Patent 2,519,886 (1950).
P. Charpentier, DE 824944 (1950).
W. Wirth, Arzneim.-Forsch., 8, 507 (1958).

Diethazine

A related drug, diethazine, is synthesized as follows: Charpentier, P.; Cmpt. Rend. 1947, 225, 306.

Pyrathiazine^[1]

Tetrameprozine (aminopromazin)

References

^ Reid, Wm. Bradley (1948). "Histamine Antagonists. II. N-(Pyrrolidylalkyl)-phenothiazines". Journal of the American Chemical Society 70 (9): 3100–3102. doi:10.1021/ja01189a079. edit

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

English Journal

Field-amplified sample injection coupled with pseudo-isotachophoresis technique for sensitive determination of selected psychiatric drugs in human urine samples after dispersive liquid-liquid microextraction.

Dziomba S1, Kowalski P2, Słomińska A1, Bączek T1.Author information 1Department of Pharmaceutical Chemistry, Medical University of Gdańsk, Hallera 107, 80-416 Gdańsk, Poland.2Department of Pharmaceutical Chemistry, Medical University of Gdańsk, Hallera 107, 80-416 Gdańsk, Poland. Electronic address: piotr.kowalski@gumed.edu.pl.AbstractA field-amplified sample injection (FASI) technique was elaborated for fast and sensitive determination of selected central nervous system drugs in human urine samples. Factors affecting the sensitivity enhancement, such as background electrolyte (BGE) and the analytical matrix composition were optimized and discussed. Pseudo-isotachophoresis (p-ITP) mechanism contribution in preconcentration mechanism was discussed. All separations were performed in uncoated fused silica capillaries 50 μm × 57 cm at 22 kV. The optimized analytical matrix was composed of 0.25 mM HCOOH in 90% (v/v) methanol, while BGE contained 45 mM TRIS/HCl (pH 2.20). The head-column injection was performed in 0.25 mM HCOOH water solution (3s, 3.45 kPa). Sample was introduced into the capillary by electrokinetic injection (70 s, 5 kV) followed by short BGE plug (3s, 3.45 kPa). Seven psychiatric drugs (olanzapine, prochlorperazine dimaleate, trifluoperazine dihydrochloride, perphenazine, promazine hydrochloride, clomipramine hydrochloride, and chlorprothixene hydrochloride) were separated in about 6 min. The elaborated method was additionally supported with dispersive liquid-liquid microextraction (DLLME) technique which in summary with FASI provided about 8000-13,000-fold sensitivity enhancement in comparison to the capillary zone electrophoresis (CZE) method with standard hydrodynamic injection (5s, 3.45 kPa).
Analytica chimica acta.Anal Chim Acta.2014 Feb 6;811:88-93. doi: 10.1016/j.aca.2013.12.021. Epub 2013 Dec 26.
A field-amplified sample injection (FASI) technique was elaborated for fast and sensitive determination of selected central nervous system drugs in human urine samples. Factors affecting the sensitivity enhancement, such as background electrolyte (BGE) and the analytical matrix composition were opti
PMID 24456599

Structural basis of prion inhibition by phenothiazine compounds.

Baral PK1, Swayampakula M1, Rout MK1, Kav NN2, Spyracopoulos L1, Aguzzi A3, James MN4.Author information 1Department of Biochemistry, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB T6G 2H7, Canada.2Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB T6G 2P5, Canada.3Department of Pathology, Institute of Neuropathology, University Hospital Zurich, Zurich 8091, Switzerland.4Department of Biochemistry, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB T6G 2H7, Canada. Electronic address: michael.james@ualberta.ca.AbstractConformational transitions of the cellular form of the prion protein, PrP(C), into an infectious isoform, PrP(Sc), are considered to be central events in the progression of fatal neurodegenerative diseases known as transmissible spongiform encephalopathies. Tricyclic phenothiazine compounds exhibit antiprion activity; however, the underlying molecular mechanism of PrP(Sc) inhibition remains elusive. We report the molecular structures of two phenothiazine compounds, promazine and chlorpromazine bound to a binding pocket formed at the intersection of the structured and the unstructured domains of the mouse prion protein. Promazine binding induces structural rearrangement of the unstructured region proximal to β1, through the formation of a "hydrophobic anchor." We demonstrate that these molecules, promazine in particular, allosterically stabilize the misfolding initiator-motifs such as the C terminus of α2, the α2-α3 loop, as well as the polymorphic β2-α2 loop. Hence, the stabilization effects of the phenothiazine derivatives on initiator-motifs induce a PrP(C) isoform that potentially resists oligomerization.
Structure (London, England : 1993).Structure.2014 Feb 4;22(2):291-303. doi: 10.1016/j.str.2013.11.009. Epub 2013 Dec 26.
Conformational transitions of the cellular form of the prion protein, PrP(C), into an infectious isoform, PrP(Sc), are considered to be central events in the progression of fatal neurodegenerative diseases known as transmissible spongiform encephalopathies. Tricyclic phenothiazine compounds exhibit
PMID 24373770

Quantification of typical antipsychotics in human plasma by ultra-high performance liquid chromatography tandem mass spectrometry for therapeutic drug monitoring.

Gradinaru J1, Vullioud A, Eap CB, Ansermot N.Author information 1Unit of Pharmacogenetics and Clinical Psychopharmacology, Center for Psychiatric Neurosciences, Department of Psychiatry, Lausanne University Hospital, Hospital of Cery, 1008 Prilly-Lausanne, Switzerland.AbstractA selective and sensitive method was developed for the simultaneous quantification of seven typical antipsychotic drugs (cis-chlorprothixene, flupentixol, haloperidol, levomepromazine, pipamperone, promazine and zuclopenthixol) in human plasma. Ultra-high performance liquid chromatography (UHPLC) was used for complete separation of the compounds in less than 4.5min on an Acquity UPLC BEH C18 column (2.1mm×50mm; 1.7μm), with a gradient elution of ammonium formate buffer pH 4.0 and acetonitrile at a flow rate of 400μl/min. Detection was performed on a tandem quadrupole mass spectrometer (MS/MS) equipped with an electrospray ionization interface. A simple protein precipitation procedure with acetonitrile was used for sample preparation. Thanks to the use of stable isotope-labeled internal standards for all analytes, internal standard-normalized matrix effects were in the range of 92-108%. The method was fully validated to cover large concentration ranges of 0.2-90ng/ml for haloperidol, 0.5-90ng/ml for flupentixol, 1-450ng/ml for levomepromazine, promazine and zuclopenthixol and 2-900ng/ml for cis-chlorprothixene and pipamperone. Trueness (89.1-114.8%), repeatability (1.8-9.9%), intermediate precision (1.9-16.3%) and accuracy profiles (<30%) were in accordance with the latest international recommendations. The method was successfully used in our laboratory for routine quantification of more than 500 patient plasma samples for therapeutic drug monitoring. To the best of our knowledge, this is the first UHPLC-MS/MS method for the quantification of the studied drugs with a sample preparation based on protein precipitation.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2014 Jan 25;88:36-44. doi: 10.1016/j.jpba.2013.07.041. Epub 2013 Aug 7.
A selective and sensitive method was developed for the simultaneous quantification of seven typical antipsychotic drugs (cis-chlorprothixene, flupentixol, haloperidol, levomepromazine, pipamperone, promazine and zuclopenthixol) in human plasma. Ultra-high performance liquid chromatography (UHPLC) wa
PMID 24036032

Japanese Journal

犬の麻酔前投薬-導入薬の組み合わせとしてのプロピオニールプロマジン-プロポフォール, -ケタミン, または-チオペンタールの効果

山下和人,伊藤若菜,久代季子,UMAR Mohammed Ahmed,都築圭子,前原誠也,瀬野貴弘,泉澤康晴
日本獣医師会雑誌 = Journal of the Japan Veterinary Medical Association 57(10), 651-656, 2004-10-20
NAID 10013655246

Thermodynamics of Partitioning of Phenothiazine Drugs between Phosphatidylcholine Bilayer Vesicles and Water Studied by Second-Derivative Spectrophotometry

TAKEGAMI Shigehiko,KITAMURA Keisuke,KITADE Tatsuya,KITAGAWA Ai,KAWAMURA Kikuko
Chemical & pharmaceutical bulletin 51(9), 1056-1059, 2003-09-01
… The partition coefficients (K_ps) of phenothiazine drugs (trifluoperazine, triflupromazine, chlorpromazine and promazine) between phosphatidylcholine (PC) small unilamellar vesicles (SUV) and water were determined over the temperature range of 10-40℃ by a second-derivative spectrophotometric method. …
NAID 110003615455

Related Pictures

★リンクテーブル★

リンク元	「プロマジン」「bromazine」
拡張検索	「chlorpromazine hydrochloride」「levomepromazine hydrochloride」「chlorpromazine」

「プロマジン」

Promazine
Systematic (IUPAC) name
	N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a600010
Legal status	?
Pharmacokinetic data
Protein binding	94%
Identifiers
CAS number	58-40-2
ATC code	N05AA03
PubChem	CID 4926
DrugBank	DB00420
ChemSpider	4757
UNII	O9M39HTM5W
ChEBI	CHEBI:8459
ChEMBL	CHEMBL564
Chemical data
Formula	C17H20N2S
Mol. mass	284.42 g/mol
	SMILES CN(C)CCCN1c2ccccc2Sc3c1cccc3;
	InChI InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 ; Key:ZGUGWUXLJSTTMA-UHFFFAOYSA-N ;
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