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
Neurologic complications in patients treated with lithium.	1988 Sep	3054982
[Electroconvulsive therapy in treatment of acute life threatening catatonia in toxic epidermal necrolysis (Lyell syndrome)].	1992 May	1603193
An acute psychotic disorder caused by pefloxacin: a case report.	1996 Feb	8861197
Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4.	2002 Jul-Aug	12523495
The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothiazine neuroleptics.	2002 Oct	12208554
Schizophrenia.	2003 Dec	15555143
Which neuroleptic would psychiatrists take for themselves or their relatives?	2003 Feb	12648897
Mechanisms of cellular distribution of psychotropic drugs. Significance for drug action and interactions.	2003 Feb	12551728
Effects of cytochrome P-450 inducers on the perazine metabolism in a primary culture of human hepatocytes.	2003 Jul-Aug	14581727
Screening, library-assisted identification and validated quantification of fifteen neuroleptics and three of their metabolites in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.	2003 Mar	12644990
Antipsychotic efficacy of the antidepressant trimipramine: a randomized, double-blind comparison with the phenothiazine perazine.	2003 Mar-Apr	12734763
Identification of P-glycoprotein substrates and inhibitors among psychoactive compounds--implications for pharmacokinetics of selected substrates.	2004 Aug	15285840
Schizophrenia.	2004 Dec	15865730
Blood dyscrasias induced by psychotropic drugs.	2004 Mar	15052517
The AMUP study for drug surveillance in psychiatry - a summary of inpatient data.	2004 Mar	15052511
The metabolism of the piperazine-type phenothiazine neuroleptic perazine by the human cytochrome P-450 isoenzymes.	2004 May	15056479
Halogenation of drugs enhances membrane binding and permeation.	2004 May 3	15122640
Acute psychosis with a mediastinal carcinoma metastasis.	2005 Jan	15614198
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms.	2005 Jan	15572279
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
Interactions between neuroleptics and CYP2C6 in rat liver--in vitro and ex vivo study.	2005 Nov-Dec	16382211
Direct effects of neuroleptics on the activity of CYP2A in the liver of rats.	2005 Nov-Dec	16382210
Effect of chronic treatment with perazine on lipopolysaccharide-induced interleukin-1 beta levels in the rat brain.	2006 Apr	16583240
Perazine for schizophrenia.	2006 Apr 19	16625562
Metabolic profiling of CSF: evidence that early intervention may impact on disease progression and outcome in schizophrenia.	2006 Aug	16933966
Automated analysis of quetiapine and other antipsychotic drugs in human blood by high performance-liquid chromatography with column-switching and spectrophotometric detection.	2006 Jan 18	16337441
[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
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.	2006 Oct 20	16798119
Perazine and carbamazepine in comparison to olanzapine in schizophrenia.	2007	17570951
Simple and simultaneous determination for 12 phenothiazines in human serum by reversed-phase high-performance liquid chromatography.	2007 Jul 1	17459789
[Ischemic colitis without atherosclerosis?].	2007 Mar 30	17377880
The activity of cytochrome P450 CYP2B in rat liver during neuroleptic treatment.	2007 Sep-Oct	18048963
Typical and atypical antipsychotics--the misleading dichotomy. Results from the Working Group 'Drugs in Psychiatry' (AGATE).	2008	18515977
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913).	2008 Dec 22	19102734
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008 Feb	18224312
Amisulpride plus valproate vs haloperidol plus valproate in the treatment of acute mania of bipolar I patients: a multicenter, open-label, randomized, comparative trial.	2008 Jun	18830442
[Antipsychotics in clinical practice. Treatment of the first schizophrenic episode].	2008 Nov-Dec	19441663
[Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples].	2008 Oct-Dec	19441687
[Drug-induced agranulocytosis--case reports and literature review].	2009	19788146
Perazine elevates clozapine serum levels by inhibiting hepatic metabolism.	2009 Aug 1	19376183
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study.	2009 Dec	19823762
Spectroscopic and electrochemical analysis of psychotropic drugs.	2009 Jan	20177449
Validation of derivative spectrophotometry method for determination of active ingredients from neuroleptics in pharmaceutical preparations.	2009 Jul-Aug	19702165
Effects of typical and atypical antipsychotic drugs on gene expression profiles in the liver of schizophrenia subjects.	2009 Sep 16	19758435
Perazine at therapeutic drug concentrations inhibits human cytochrome P450 isoenzyme 1A2 (CYP1A2) and caffeine metabolism--an in vitro study.	2009 Sep-Oct	19904008
The role of CYP2D6 and TaqI A polymorphisms in malignant neuroleptic syndrome: two case reports with three episodes.	2010 Mar	20305604
[Perazine in the treatment of psychotic disorders--research review].	2010 May-Jun	20672521
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