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Details

Stereochemistry ACHIRAL
Molecular Formula C20H25N3S.2C4H4O4
Molecular Weight 571.642
Optical Activity NONE
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 No
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 No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Cytochrome P450 2B, Rattus norvegicus
45.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Taxilan

Approved Use

Taxilan is used in the treatment of schizophrenia
PubMed

PubMed

TitleDatePubMed
Neurologic complications in patients treated with lithium.
1988 Sep
[Electroconvulsive therapy in treatment of acute life threatening catatonia in toxic epidermal necrolysis (Lyell syndrome)].
1992 May
An acute psychotic disorder caused by pefloxacin: a case report.
1996 Feb
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia].
2001 Jan-Feb
Switching to amisulpride due to hepatic complications.
2002 May
Schizophrenia.
2003 Dec
Mechanisms of cellular distribution of psychotropic drugs. Significance for drug action and interactions.
2003 Feb
Blood dyscrasias induced by psychotropic drugs.
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
Interactions between neuroleptics and CYP2C6 in rat liver--in vitro and ex vivo study.
2005 Nov-Dec
Direct effects of neuroleptics on the activity of CYP2A in the liver of rats.
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
Characterization of human cytochrome p450 enzymes involved in the metabolism of the piperidine-type phenothiazine neuroleptic thioridazine.
2006 Mar
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
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
[Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples].
2008 Oct-Dec
[Perazine in the treatment of psychotic disorders--research review].
2010 May-Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In acutely ill and severely disturbed patients 50 mg perazine at time-intervals of 30 minutes can be administered intramuscularly
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 Fri Dec 15 16:59:01 GMT 2023
Edited
by admin
on Fri Dec 15 16:59:01 GMT 2023
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
PHENOTHIAZINE, 10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, MALEATE (1:2)
Systematic Name English
Perazine dimaleate [WHO-DD]
Common Name English
10H-PHENOTHIAZINE, 10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, (2Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
Code System Code Type Description
SMS_ID
100000079420
Created by admin on Fri Dec 15 16:59:01 GMT 2023 , Edited by admin on Fri Dec 15 16:59:01 GMT 2023
PRIMARY
PUBCHEM
5282417
Created by admin on Fri Dec 15 16:59:01 GMT 2023 , Edited by admin on Fri Dec 15 16:59:01 GMT 2023
PRIMARY
CAS
14516-56-4
Created by admin on Fri Dec 15 16:59:01 GMT 2023 , Edited by admin on Fri Dec 15 16:59:01 GMT 2023
PRIMARY
EVMPD
SUB14812MIG
Created by admin on Fri Dec 15 16:59:01 GMT 2023 , Edited by admin on Fri Dec 15 16:59:01 GMT 2023
PRIMARY
FDA UNII
3VG1507988
Created by admin on Fri Dec 15 16:59:01 GMT 2023 , Edited by admin on Fri Dec 15 16:59:01 GMT 2023
PRIMARY
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ACTIVE MOIETY