PERAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H25N3S
Molecular Weight	339.498
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CCCN2C3=C(SC4=C2C=CC=C4)C=CC=C3)CC1

InChI

InChIKey=WEYVCQFUGFRXOM-UHFFFAOYSA-N

InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16625562
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12523495 and http://www.genome.jp/dbget-bin/www_bget?D01412

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. Perazine is an older antipsychotic drug first introduced in the 1950s. It is suggested to have a low level of side effects (especially for movement disorders). Its use is regional and restricted to countries like Germany, Poland, the Netherlands and the former Yugoslavia. Perazine has being shown to be a potent inhibitor of human CYP1A2. It acts as a dopamine antagonist.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12523495	Inhibitor 8297
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: http://www.genome.jp/dbget-bin/www_bget?D01412	Antagonist 2778
Cytochrome P450 2B, Rattus norvegicus 2 Target ID: Cytochrome P450 2B, Rattus norvegicus Sources: http://www.ncbi.nlm.nih.gov/pubmed/18048963	Inhibitor 8297	45.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11869638	Primary		Approved 8429	Taxilan Approved Use Taxilan is used in the treatment of schizophrenia

PubMed

Title	Date	PubMed
[Electroconvulsive therapy in treatment of acute life threatening catatonia in toxic epidermal necrolysis (Lyell syndrome)].	1992 May	1603193
Neuroleptics normalize increased release of interleukin- 1 beta and tumor necrosis factor-alpha from monocytes in schizophrenia.	2001 Jul 1	11439237
Switching to amisulpride due to hepatic complications.	2002 May	12052579
Which neuroleptic would psychiatrists take for themselves or their relatives?	2003 Feb	12648897
Schizophrenia.	2004 Dec	15865730
Increased serum interleukin-1beta and interleukin-6 in elderly, chronic schizophrenic patients on stable antipsychotic medication.	2005 Jun	18568063
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.	2005 Nov-Dec	16526447
Metabolic profiling of CSF: evidence that early intervention may impact on disease progression and outcome in schizophrenia.	2006 Aug	16933966
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].	2006 Jun	16856516
Characterization of human cytochrome p450 enzymes involved in the metabolism of the piperidine-type phenothiazine neuroleptic thioridazine.	2006 Mar	16272405
[Antipsychotics in clinical practice. Treatment of the first schizophrenic episode].	2008 Nov-Dec	19441663
[Drug-induced agranulocytosis--case reports and literature review].	2009	19788146
Validation of derivative spectrophotometry method for determination of active ingredients from neuroleptics in pharmaceutical preparations.	2009 Jul-Aug	19702165
The role of CYP2D6 and TaqI A polymorphisms in malignant neuroleptic syndrome: two case reports with three episodes.	2010 Mar	20305604
Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines.	2010 Oct 15	20615392

Patents

Sample Use Guides

In Vivo Use Guide

The customary dose range recommended for this antipsychotic under in-patient conditions is 75-600 mg/day (maximum 1000 mg/day).

Route of Administration: Oral

In Vitro Use Guide

About 80% of basal human CYP1A2 activity was reduced by the therapeutic concentrations of perazine (5-10 uM).

Name

Type

Language

PERAZINE

Common Name

English

PROCHLORPERAZINE MALEATE IMPURITY B [EP IMPURITY]

Common Name

English

10-(3-(4-METHYLPIPERAZIN-1-YL)PROPYL)PHENOTHIAZINE

Systematic Name

English

PERAZINE [MI]

Common Name

English

Perazine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05AB10