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Details

Stereochemistry ACHIRAL
Molecular Formula C20H25N3S.2C4H4O4
Molecular Weight 571.642
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PERAZINE DIMALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CN1CCN(CCCN2C3=C(SC4=C2C=CC=C4)C=CC=C3)CC1

InChI

InChIKey=PQDKNYWKLCFCJU-SPIKMXEPSA-N
InChI=1S/C20H25N3S.2C4H4O4/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;2*5-3(6)1-2-4(7)8/h2-5,7-10H,6,11-16H2,1H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Taxilan
PubMed

PubMed

TitleDatePubMed
Neurologic complications in patients treated with lithium.
1988 Sep
An acute psychotic disorder caused by pefloxacin: a case report.
1996 Feb
Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro.
2000 Sep
[Neuroleptic malignant syndrome--case report].
2001
The effect of selective serotonin reuptake inhibitors (SSRIs) on the pharmacokinetics and metabolism of perazine in the rat.
2001 Apr
Relevance of liver enzyme elevations with four different neuroleptics: a retrospective review of 7,263 treatment courses.
2001 Apr
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia].
2001 Jan-Feb
Neuroleptics normalize increased release of interleukin- 1 beta and tumor necrosis factor-alpha from monocytes in schizophrenia.
2001 Jul 1
Examination of iron (III) and hexacyanoferrate (III) ions as reagents for the spectrophotometric determination of promazine and perazine.
2001 Nov-Dec
Prevalence of obesity in adolescent and young adult patients with and without schizophrenia and in relationship to antipsychotic medication.
2001 Nov-Dec
Intracellular distribution of psychotropic drugs in the grey and white matter of the brain: the role of lysosomal trapping.
2001 Oct
Switching to amisulpride due to hepatic complications.
2002 May
Schizophrenia.
2003 Dec
Effects of cytochrome P-450 inducers on the perazine metabolism in a primary culture of human hepatocytes.
2003 Jul-Aug
Antipsychotic efficacy of the antidepressant trimipramine: a randomized, double-blind comparison with the phenothiazine perazine.
2003 Mar-Apr
Identification of P-glycoprotein substrates and inhibitors among psychoactive compounds--implications for pharmacokinetics of selected substrates.
2004 Aug
Blood dyscrasias induced by psychotropic drugs.
2004 Mar
The AMUP study for drug surveillance in psychiatry - a summary of inpatient data.
2004 Mar
The metabolism of the piperazine-type phenothiazine neuroleptic perazine by the human cytochrome P-450 isoenzymes.
2004 May
Acute psychosis with a mediastinal carcinoma metastasis.
2005 Jan
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
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2005 Nov-Dec
Effect of chronic treatment with perazine on lipopolysaccharide-induced interleukin-1 beta levels in the rat brain.
2006 Apr
Perazine for schizophrenia.
2006 Apr 19
Metabolic profiling of CSF: evidence that early intervention may impact on disease progression and outcome in schizophrenia.
2006 Aug
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
[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
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
Simple and simultaneous determination for 12 phenothiazines in human serum by reversed-phase high-performance liquid chromatography.
2007 Jul 1
[Ischemic colitis without atherosclerosis?].
2007 Mar 30
Typical and atypical antipsychotics--the misleading dichotomy. Results from the Working Group 'Drugs in Psychiatry' (AGATE).
2008
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
[Antipsychotics in clinical practice. Treatment of the first schizophrenic episode].
2008 Nov-Dec
[Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples].
2008 Oct-Dec
[Drug-induced agranulocytosis--case reports and literature review].
2009
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study.
2009 Dec
Spectroscopic and electrochemical analysis of psychotropic drugs.
2009 Jan
Validation of derivative spectrophotometry method for determination of active ingredients from neuroleptics in pharmaceutical preparations.
2009 Jul-Aug
Effects of typical and atypical antipsychotic drugs on gene expression profiles in the liver of schizophrenia subjects.
2009 Sep 16
Perazine at therapeutic drug concentrations inhibits human cytochrome P450 isoenzyme 1A2 (CYP1A2) and caffeine metabolism--an in vitro study.
2009 Sep-Oct
The role of CYP2D6 and TaqI A polymorphisms in malignant neuroleptic syndrome: two case reports with three episodes.
2010 Mar
[Perazine in the treatment of psychotic disorders--research review].
2010 May-Jun
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
Patents

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).
Substance Class Chemical
Created
by admin
on Tue Oct 22 19:43:28 UTC 2019
Edited
by admin
on Tue Oct 22 19:43:28 UTC 2019
Record UNII
3VG1507988
Record Status Validated (UNII)
Record Version
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Name Type Language
PERAZINE DIMALEATE
WHO-DD  
Common Name English
PERAZINE MALEATE [JAN]
Common Name English
PERAZINE MALEATE
JAN  
Common Name English
PERAZINE DIMALEATE [WHO-DD]
Common Name English
PHENOTHIAZINE, 10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, MALEATE (1:2)
Systematic Name English
10H-PHENOTHIAZINE, 10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, (2Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
Code System Code Type Description
PUBCHEM
5282417
Created by admin on Tue Oct 22 19:43:28 UTC 2019 , Edited by admin on Tue Oct 22 19:43:28 UTC 2019
PRIMARY
CAS
14516-56-4
Created by admin on Tue Oct 22 19:43:28 UTC 2019 , Edited by admin on Tue Oct 22 19:43:28 UTC 2019
PRIMARY
EVMPD
SUB14812MIG
Created by admin on Tue Oct 22 19:43:28 UTC 2019 , Edited by admin on Tue Oct 22 19:43:28 UTC 2019
PRIMARY
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