Page last updated: 2024-12-05

perazine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Perazine: A phenothiazine antipsychotic with actions and uses similar to those of CHLORPROMAZINE. Extrapyramidal symptoms may be more common than other side effects. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

perazine : A phenothiazine derivative in which 10H-phenothiazinecarries a 3-(4-methylpiperazin-1-yl)propyl substituent at the N-10 position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID4744
CHEMBL ID1697766
CHEBI ID59118
SCHEMBL ID147165
MeSH IDM0016251

Synonyms (44)

Synonym
CHEBI:59118 ,
n-methyl-piperazinylpropyl-phenothiazine
10-[3-(4-methylpiperazin-1-yl)propyl]-10h-phenothiazine
n-methyl-piperazinyl-n'-propyl-phenothiazin
nsc-638694
perazine
nsc638694
10h-phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-
phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-
10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine
10-(3-(4-methyl-1-piperazinyl)propyl)-10h-phenothiazine
n-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine
einecs 201-578-9
pernazine
taxilan
psytomin
p 725
n-methyl-piperazinyl-n'-propyl-phenothiazin [german]
10h-phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-
NCGC00159492-02
NCGC00159492-03
84-97-9
AKOS000281842
C16903
CHEMBL1697766
8915147a2b ,
unii-8915147a2b
dtxcid3028554
dtxsid6048628 ,
tox21_112970
cas-84-97-9
SCHEMBL147165
10-(3-(4-methylpiperazin-1-yl)propyl)phenothiazine
perazine [mi]
prochlorperazine maleate impurity b [ep impurity]
perazine [who-dd]
WEYVCQFUGFRXOM-UHFFFAOYSA-N
n-methyl-piperazinyl-n'-propyl-phenothiazine
perazin
DB12710
Q392481
10-(3-(4-methylpiperazin-1-yl)propyl)-10h-phenothiazine
us9504692, 3946
EN300-18544900

Research Excerpts

Overview

Perazine is an old phenothiazine derivative used for the treatment of people with schizophrenia. Perazine is reputed to have a low level of extrapyramidal adverse effects.

ExcerptReferenceRelevance
"Perazine is an old phenothiazine derivative used for the treatment of people with schizophrenia and is reputed to have a low level of extrapyramidal adverse effects. "( Perazine for schizophrenia.
Hartung, B; Helfer, B; Leucht, S, 2014
)
3.29
"Perazine is an old phenothiazine derivative used for the treatment of people with schizophrenia and is reputed to have a low level of extrapyramidal adverse effects. "( Perazine for schizophrenia.
Hartung, B; Leucht, S, 2006
)
3.22
"Perazine (PER) is a phenothiazine antipsychotic drug frequently used in Germany that undergoes extensive metabolism."( Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro.
Brockmöller, J; Roots, I; Schmider, J; Störmer, E, 2000
)
1.97
"Perazine is a potent inhibitor of dextromethorphan-O-demethylase, S-mephenytoin-hydroxylase, alprazolam-4-hydroxylase, phenacetin-O-deethylase and tolbutamide-hydroxylase activity in human liver microsomes."( Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro.
Brockmöller, J; Roots, I; Schmider, J; Störmer, E, 2000
)
1.25
"Perazine is an old phenothiazine derivative used for the treatment of people with schizophrenia which has a reputed low level of extrapyramidal side-effects. "( Perazine for schizophrenia.
Hartung, B; Leucht, S, 2002
)
3.2

Treatment

Treatment with perazine (30 mg/kg/day) reduced LPS-stimulated IL-1 beta levels in the hypothalamus. A tendency to its decrease in the striatum and frontal cortex was observed.

ExcerptReferenceRelevance
"Perazine treatment was associated with the significantly highest intensity of EPS."( Pharmacogenetics of adverse events in schizophrenia treatment: comparison study of ziprasidone, olanzapine and perazine.
Beszlej, A; Bienkowski, P; Frydecka, D; Grzywacz, A; Mierzejewski, P; Samochowiec, A; Samochowiec, J; Trześniowska-Drukała, B; Tybura, P, 2014
)
1.34
"Treatment with perazine (30 mg/kg/day) reduced LPS-stimulated IL-1 beta levels in the hypothalamus, and a tendency to its decrease in the striatum and frontal cortex was observed."( Effect of chronic treatment with perazine on lipopolysaccharide-induced interleukin-1 beta levels in the rat brain.
Daniel, WA; Drzyzga, L; Herman, ZS; Marcinowska, A; Obuchowicz, E; Wójcikowski, J, 2006
)
0.95

Toxicity

ExcerptReferenceRelevance
"The primary aim of the present study was to assess the possible associations between dopaminergic, serotonergic, and glutamatergic system-related genes and adverse events after antipsychotic treatment in paranoid schizophrenia patients."( Pharmacogenetics of adverse events in schizophrenia treatment: comparison study of ziprasidone, olanzapine and perazine.
Beszlej, A; Bienkowski, P; Frydecka, D; Grzywacz, A; Mierzejewski, P; Samochowiec, A; Samochowiec, J; Trześniowska-Drukała, B; Tybura, P, 2014
)
0.61

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetic parameters investigated seem to have a limited influence on the clinical outcome."( Prediction and evaluation criteria in perazine therapy of acute schizophrenics. Pharmacokinetic data.
Breyer-Pfaff, U; Brinkschulte, M; Rein, W; Schied, HW; Straube, E, 1983
)
0.54
" The aim of the present study was to investigate the contribution of lysosomal trapping to the total tissue uptake of perazine, and the pharmacokinetic interaction between the neuroleptic and antidepressants."( Lysosomal trapping as an important mechanism involved in the cellular distribution of perazine and in pharmacokinetic interaction with antidepressants.
Daniel, WA; Wójcikowski, J, 1999
)
0.74

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

After 7 days the zotepine group was significantly more improved than the perazine group. A close connection existed between perazine dosage and perazine serum level.

ExcerptRelevanceReference
" In determination of the optimal individual dosage must continue to be an empirical process based on clinical observations and experience."( [Correlation between plasma concentration and clinical effect of neuroleptics and antidepressants].
Modestin, J; Petrin, A, 1976
)
0.26
" A close connection existed between perazine dosage and perazine serum level."( [Relationship between perazine serum concentration and clinical results in long-term treated schizophrenic outpatients (author's transl)].
Chaskel, H; Müller-Oerlinghausen, B; Pietzcker, A; Poppenberg, A; Schley, J; Urban, R, 1978
)
0.85
" There was a negative correlation between the daily dosage of phenothiazine and the percentages of the polyunsaturated fatty acids arachidonic acid and alpha-linolenic acid+eicosapentaenoic acid+docosahexaenoic acid in thrombocytes (r = -0."( Schizophrenic patients treated with high dose phenothiazine or thioxanthene become deficient in polyunsaturated fatty acids in their thrombocytes.
Fischer, S; Kissling, W; Kuss, HJ, 1992
)
0.28
" After 7 days the zotepine group was significantly more improved than the perazine group, possibly due to a dosing effect in the perazine group."( [Zotepine versus perazine in patients with paranoid schizophrenia: a double-blind controlled trial of its effectiveness].
Benkert, O; Holsboer, F; von Bardeleben, U; Wetzel, H, 1991
)
0.85
"Rebound insomnia is one of the medical effects of reduction in dosage or discontinuation of neuroleptic drugs."( Rebound insomnia in neuroleptic drug withdrawal neurophysiologic characteristics.
van Sweden, B, 1987
)
0.27
" Numerous patients had already modified their neuroleptic dosage on their own initiative, in most cases discontinuing their medication but in some cases increasing or reducing the dose."( [Experiences of schizophrenic patients in ambulatory care with oral neuroleptics--baseline for psychoeducational interventions].
Buchkremer, G; Franzen, U; Hornung, WP, 1994
)
0.29
" Groups were matched for demographic characteristics and daily dosage of RIS."( Cytochrome P450-mediated interaction between perazine and risperidone: implications for antipsychotic polypharmacy.
Gründer, G; Haen, E; Hiemke, C; Lammertz, SE; Paulzen, M; Schoretsanitis, G; Stegmann, B, 2017
)
0.71
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
phenothiazine antipsychotic drugnull
dopaminergic antagonistA drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
N-alkylpiperazine
N-methylpiperazine
phenothiazines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency25.49570.000811.382244.6684AID686978; AID686979
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency26.83250.000214.376460.0339AID720691
estrogen nuclear receptor alphaHomo sapiens (human)Potency24.62300.000229.305416,493.5996AID743069; AID743078
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency21.31380.001019.414170.9645AID743140
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency28.18380.035520.977089.1251AID504332
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency10.59090.001723.839378.1014AID743083
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency18.87120.000323.4451159.6830AID743065; AID743066; AID743067
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency28.18380.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID1426438Antimycobacterial activity against drug-succeptible Mycobacterium tuberculosis CF73 incubated for 7 days measured 24 hrs post incubation by resazurin microtiter assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1426439Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis CF104 clinical isolate incubated for 7 days measured 24 hrs post incubation by resazurin microtiter assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1426434Antimycobacterial activity against Mycobacterium smegmatis MC2 155 ATCC 700084 by microplate alamar blue assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1148004Oleyl alcohol-water partition coefficient, Rm of the compound measured at 0% methanol by reverse-phase thin layer chromatography1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID1426444Inhibition of efflux pump in Mycobacterium smegmatis assessed as increase in accumulation of ethidium bromide at 0.25 times MIC measured every min for 60 mins by fluorimetric method2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1148003Dissociation constant, pKa of the compound by UV-visible spectrophotometer analysis1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID1148006Binding affinity to bovine serum albumin by circular dichroic probe technique1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1426435Antimycobacterial activity against Mycobacterium bovis BCG Pasteur ATCC 35734 by microplate alamar blue assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1426436Antimycobacterial activity against Mycobacterium tuberculosis MC2 7000 by microplate alamar blue assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1426437Antimycobacterial activity against Mycobacterium tuberculosis H37Rv ATCC 27294 incubated for 7 days measured 24 hrs post incubation by resazurin microtiter assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1148005Octanol-water partition coefficient, log P of the compound1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1148007Binding affinity to bovine serum albumin1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1148008Binding affinity to bovine serum albumin assessed as intrinsic binding constant1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID1426440Antimycobacterial activity against multidrug-resistant Mycobacterium tuberculosis CF81 clinical isolate incubated for 7 days measured 24 hrs post incubation by resazurin microtiter assay2017European journal of medicinal chemistry, Feb-15, Volume: 127Synthesis and SAR evaluation of novel thioridazine derivatives active against drug-resistant tuberculosis.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (137)

TimeframeStudies, This Drug (%)All Drugs %
pre-199070 (51.09)18.7374
1990's25 (18.25)18.2507
2000's24 (17.52)29.6817
2010's15 (10.95)24.3611
2020's3 (2.19)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.05

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index44.05 (24.57)
Research Supply Index5.21 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index65.65 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials17 (10.30%)5.53%
Reviews10 (6.06%)6.00%
Case Studies31 (18.79%)4.05%
Observational0 (0.00%)0.25%
Other107 (64.85%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Evaluation of the Necessity of Long-term Pharmacological Treatment With Antipsychotics for the Prevention of Relapse in Long-term Stabilized Schizophrenic Patients: a Randomized, Single-blind, Longitudinal Trial [NCT02307396]Phase 421 participants (Actual)Interventional2015-02-01Completed
Pharmacovigilance in Gerontopsychiatric Patients [NCT02374567]Phase 3407 participants (Actual)Interventional2015-01-31Terminated
[information is prepared from clinicaltrials.gov, extracted Sep-2024]