Page last updated: 2024-11-05

norchlorcyclizine

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

Description

Norchlorcyclizine is a piperazine derivative that acts as an antihistamine. It is structurally related to cyclizine, and is a potent inhibitor of histamine H1 receptors. It has been used to treat motion sickness, allergic reactions, and other conditions. Research on norchlorcyclizine has focused on its potential therapeutic applications in the treatment of various diseases, such as Alzheimer's disease, Parkinson's disease, and cancer. Its mechanism of action involves blocking histamine receptors, which play a role in various physiological processes, including inflammation, allergic reactions, and neurotransmission. Norchlorcyclizine has been shown to exhibit anti-inflammatory and anti-tumor activity in preclinical studies. However, its clinical use is limited due to its potential side effects, such as drowsiness, dizziness, and dry mouth.'

norchlorcyclizine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9340
CHEMBL ID81324
SCHEMBL ID467086
MeSH IDM0052719

Synonyms (108)

Synonym
AC-3019
CHEMBL81324
EN300-18220
smr000131751
MLS000521343
n-(4-chlorophenyl)phenylmethylpiperazine
n-(p-chlorobenzhydryl)piperazine
1-(4-chlorobenzhydryl)piperazine
4-(4-chlorobenzhydryl)piperazine
piperazine, 1-[.alpha.-(4-chlorophenyl)benzyl]-
nsc-86164
1-(.alpha.-phenyl-4-chlorobenzyl)piperazine
norchlorcyclizine
nsc86164
piperazine, 1-(p-chloro-.alpha.-phenylbenzyl)-
303-26-4
1-(4-chloro-.alpha.-phenylbenzyl)piperazine
piperazine, 1-[(4-chlorophenyl)phenylmethyl]-
n-(4-chlorobenzhydryl)piperazine
einecs 206-137-4
1-(4-chloro-alpha-phenylbenzyl)piperazine
piperazine, 1-((4-chlorophenyl)phenylmethyl)-
1-(alpha-phenyl-4-chlorobenzyl)piperazine
piperazine, 1-(alpha-(4-chlorophenyl)benzyl)-
nsc 86164
brn 0243027
piperazine, 1-(p-chloro-alpha-phenylbenzyl)-
1-[(4-chlorophenyl)(phenyl)methyl]piperazine
STK083473
EU-0099994
1-(4-chlorobenzhydryl)piperazine, technical grade, 90%
OPREA1_771131
C1611
1-(4-chlorodiphenylmethyl)piperazine
AKOS000268792
HMS1648P05
1-[(4-chlorophenyl)-phenylmethyl]piperazine
(-)-1-[(4-chlorophenyl)phenylmethyl]piperazine
FT-0658637
FT-0664913
130018-88-1
1-[(4-chlorophenyl)-phenyl-methyl]piperazine
A806004
1-((4-chlorophenyl)(phenyl)methyl)piperazine
NCGC00245963-01
HMS2464F07
unii-t875vn0d6e
t875vn0d6e ,
4-23-00-00072 (beilstein handbook reference)
1-(4-chlorobenzhydryl) piperazine
BBL010366
c17h19cln2
FT-0604325
FT-0604324
FT-0629215
meclozine dihydrochloride impurity h [ep impurity]
hydroxyzine hydrochloride impurity a [ep impurity]
cetirizine dihydrochloride impurity a [ep impurity]
cetirizine hydrochloride impurity cbhp [usp impurity]
cbhp
1-((4-chlorophenyl)phenylmethyl)piperazine
(+/-)-1-(p-chlorobenzhydryl)piperazine
chlorobenzhydryl piperazine
cetirizine impurity a
norchlorcyclizine, (+/-)-
1-[(4-chlorophenyl)phenylmethyl]piperazine
AKOS016039386
GF-0133
mfcd00005965
SY003580
1-[(r)-(4-chlorophenyl)-phenyl-methyl]piperazine
piperazine, 1-(.alpha.-(4-chlorophenyl)benzyl)-
(-)-1-[(4chlorophenyl) phenylmethyl]piperazine
(-)-1-[(4-chloro-phenyl)-phenyl-methyl]-piperazine
1-[(4-chloro-phenyl)-phenyl-methyl]-piperazine
4-chlorobenzhydrylpiperazine
1-[(4-chlorophenyl)-phenylmethyl]-piperazine
(-)-1-[(4-chloro phenyl)phenylmethyl]piperazine
4-chlorobenzhydryl piperazine
1-[(4-chlorophenyl)phenylmethyl)piperazine
n-[(4-chlorophenyl)(phenyl)-methyl]piperazine
SCHEMBL467086
levocetirizine impurity 2
Q-200042
(s)-nor-ccz
gtpl9162
compound c10 [pmid: 24297249]
cetirizine impurity a, european pharmacopoeia (ep) reference standard
SR-01000597190-1
sr-01000597190
CS-W001978
meclozine impurity h, european pharmacopoeia (ep) reference standard
(rs)-1-[(4-chlorophenyl)phenylmethyl]piperazine
cpp_287.1310_14.5
Z57388987
DTXSID00891490
Q27076864
BCP08791
(-)-1-[(4-chlorophenyl) phenylmethyl] piperazine
(r)-cetirizine ep impurity a;(r)-1-((4-chlorophenyl)(phenyl)methyl)piperazine
BCP34517
AMY40892
c 10c10
(-)-1-[1-(4-chlorophenyl)phenylmethyl]piperazine
SB47944
meclozine impurity h
1-[(4-chlorophenyl)phenylmethyl]-piperazine-d8
HY-W001978

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Depending on the intended indication and dosing regimen, PPL can delay or stop development of a compound in the drug discovery process."( Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential.
Gehlhaar, D; Greene, N; Johnson, TO; Pelletier, DJ; Tilloy-Ellul, A,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency5.62340.044717.8581100.0000AID485294
glp-1 receptor, partialHomo sapiens (human)Potency8.91250.01846.806014.1254AID624417
thioredoxin reductaseRattus norvegicus (Norway rat)Potency15.84890.100020.879379.4328AID588453
GLS proteinHomo sapiens (human)Potency35.48130.35487.935539.8107AID624170
TDP1 proteinHomo sapiens (human)Potency19.47630.000811.382244.6684AID686978; AID686979
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency22.38720.28189.721235.4813AID2326
glucocerebrosidaseHomo sapiens (human)Potency2.51190.01268.156944.6684AID2101
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency0.70790.707936.904389.1251AID504333
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency15.84890.316212.765731.6228AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency15.84890.00638.235039.8107AID881
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
short transient receptor potential channel 6 isoform 1Mus musculus (house mouse)EC50 (µMol)50.12000.020020.518970.7900AID2696
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID214497Percent Inhibition of trypanothione reductase activity at 57 uM concentration1997Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15
A virtual screening approach applied to the search for trypanothione reductase inhibitors.
AID1810699Agonist activity at full length TLX activating element expressed in human HEK293T cells coexpressing human full-length TLX/Gal4-VP 16 assessed as fold increase in reporter activity at 100 uM by luciferase reporter gene assay relative to control2021Journal of medicinal chemistry, 06-24, Volume: 64, Issue:12
Propranolol Activates the Orphan Nuclear Receptor TLX to Counteract Proliferation and Migration of Glioblastoma Cells.
AID214496Percent Inhibition of trypanothione reductase activity at 5.7 uM concentration1997Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15
A virtual screening approach applied to the search for trypanothione reductase inhibitors.
AID588208Literature-mined public compounds from Lowe et al phospholipidosis modelling dataset2010Molecular pharmaceutics, Oct-04, Volume: 7, Issue:5
Predicting phospholipidosis using machine learning.
AID1280180Selectivity index, ratio of CC50 for human Huh7.5.1 cells infected with HCV JFH-1 virus to EC50 for HCV JFH-1 virus2016Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3
Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection.
AID1810680Stabilization of human recombinant TLX LBD assessed as change in melting temperature at 500 uM by DSF assay2021Journal of medicinal chemistry, 06-24, Volume: 64, Issue:12
Propranolol Activates the Orphan Nuclear Receptor TLX to Counteract Proliferation and Migration of Glioblastoma Cells.
AID1280178Antiviral activity against HCV JFH-1 infected in Huh7.5.1 cells after 48 hrs by luciferase reporter gene assay2016Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3
Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection.
AID1810678Agonist activity at in human TLX LBD expressed in human HEK293T cells coexpressing Gal4-VP 16 assessed as fold decrease in reporter activity at 100 uM measured after 14 hrs by luciferase reporter gene assay relative to control2021Journal of medicinal chemistry, 06-24, Volume: 64, Issue:12
Propranolol Activates the Orphan Nuclear Receptor TLX to Counteract Proliferation and Migration of Glioblastoma Cells.
AID540237Phospholipidosis-positive literature compound observed in rat
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID214495Percent Inhibition of trypanothione reductase activity at 28.5 uM concentration1997Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15
A virtual screening approach applied to the search for trypanothione reductase inhibitors.
AID1280179Cytotoxicity against human Huh7.5.1 cells assessed as ATP level by luminescence analysis2016Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3
Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1345469Human Guanylyl cyclase-B (Receptor Guanylyl Cyclase (RGC) family)2014Naunyn-Schmiedeberg's archives of pharmacology, Jan, Volume: 387, Issue:1
Identification of small molecule NPR-B antagonists by high throughput screening--potential use in heart failure.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.88)18.2507
2000's2 (11.76)29.6817
2010's11 (64.71)24.3611
2020's3 (17.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.32

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.32 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index5.22 (4.65)
Search Engine Demand Index42.09 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]