Page last updated: 2024-11-10

4-phenyl-1-(4-phenylbutyl)piperidine

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

Description

4-phenyl-1-(4-phenylbutyl)piperidine: a potent ligand for sigma receptors; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035672
CHEMBL ID325238
CHEBI ID104237
SCHEMBL ID866873
MeSH IDM0249835

Synonyms (26)

Synonym
BRD-K78061844-103-01-6
tocris-0620
NCGC00024688-01 ,
NCGC00024688-02
CHEMBL325238 ,
4-phenyl-1-(4-phenylbutyl)piperidine
4-phenyl-1-(4-phenyl-butyl)-piperidine: maleate
bdbm50007400
4-phenyl-1-(4-phenyl-butyl)-piperidine
CHEBI:104237
207572-62-1
piperidine, 4-phenyl-1-(4-phenylbutyl)-
4-ppbp
136534-70-8
unii-hdl2dsb8ch
hdl2dsb8ch ,
4-ppbp maleate
SCHEMBL866873
HQGDPZPNAXRCSA-UHFFFAOYSA-N
4-phenyl-1-(4-phenylbutyl) piperidine
DTXSID50904029
Q4637191
4-bbpb
4-bbpb maleate
STARBLD0019162
PD071104

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Piglets subjected to hypoxia followed by asphyxic cardiac arrest were treated with saline or two dosing regimens of PPBP after resuscitation."( Sigma receptor ligand 4-phenyl-1-(4-phenylbutyl)-piperidine modulates neuronal nitric oxide synthase/postsynaptic density-95 coupling mechanisms and protects against neonatal ischemic degeneration of striatal neurons.
Carter, EL; Koehler, RC; Martin, LJ; Torbey, MT; Yang, ZJ, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
piperidines
[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 (31)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency35.48130.003245.467312,589.2998AID2517
USP1 protein, partialHomo sapiens (human)Potency39.81070.031637.5844354.8130AID504865
TDP1 proteinHomo sapiens (human)Potency17.53510.000811.382244.6684AID686978; AID686979
thyroid stimulating hormone receptorHomo sapiens (human)Potency3.98110.001318.074339.8107AID926; AID938
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency0.03980.00207.533739.8107AID891
cellular tumor antigen p53 isoform aHomo sapiens (human)Potency25.11890.316212.443531.6228AID902
cytochrome P450 2C19 precursorHomo sapiens (human)Potency15.84890.00255.840031.6228AID899
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency31.62280.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency1.99530.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency10.00000.316212.765731.6228AID881
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency10.00000.00638.235039.8107AID881
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency31.62281.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DRattus norvegicus (Norway rat)IC50 (µMol)10.00000.00030.50267.7625AID61032
D(2) dopamine receptorBos taurus (cattle)IC50 (µMol)0.33500.00100.79948.0000AID62166
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.16500.00010.54948.4000AID61566
5-hydroxytryptamine receptor 4 Sus scrofa (pig)IC50 (µMol)0.33500.33500.33500.3350AID62166
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

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)
synaptic transmission, dopaminergicD(2) dopamine receptorBos taurus (cattle)
negative regulation of prolactin secretionD(2) dopamine receptorBos taurus (cattle)
negative regulation of lactationD(2) dopamine receptorBos taurus (cattle)
positive regulation of mammary gland involutionD(2) dopamine receptorBos taurus (cattle)
hyaloid vascular plexus regressionD(2) dopamine receptorBos taurus (cattle)
[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 (9)

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)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
Golgi membraneD(2) dopamine receptorBos taurus (cattle)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID62166Binding affinity against Dopamine receptor D2 in bovine striatal homogenate using 200 pM [3H]- spiperone and 250 nM unlabeled ketanserin1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
N-(1-arylpropionyl)-4-aryltetrahydropyridines, a new class of high-affinity selective sigma receptor ligands.
AID61032Binding affinity towards Dopamine receptor D1 in rat membranes using [3H]SCH-23390 as radioligand1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID772808Neuroprotective activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide release at 50 uM after 20 to 24 hrs by Griess assay relative to control2013Bioorganic & medicinal chemistry, Oct-01, Volume: 21, Issue:19
N-substituted 8-aminopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecanes as σ receptor ligands with potential neuroprotective effects.
AID229185Binding affinity against sigma receptor in bovine cerebellum using 2.0 nM [3H]haloperidol in the presence of 25 nM unlabeled spiperone1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
N-(1-arylpropionyl)-4-aryltetrahydropyridines, a new class of high-affinity selective sigma receptor ligands.
AID772807Neuroprotective activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide release at 100 uM after 20 to 24 hrs by Griess assay relative to control2013Bioorganic & medicinal chemistry, Oct-01, Volume: 21, Issue:19
N-substituted 8-aminopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecanes as σ receptor ligands with potential neuroprotective effects.
AID156975Compound was tested for its affinity towards PCP receptor in rat brain membrane [3H]MK-801 as radioligand1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID204001The compound was tested for its binding affinity towards Sigma opioid receptor in guinea pig brain membranes1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID772806Neuroprotective activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide release at 20 uM after 20 to 24 hrs by Griess assay2013Bioorganic & medicinal chemistry, Oct-01, Volume: 21, Issue:19
N-substituted 8-aminopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecanes as σ receptor ligands with potential neuroprotective effects.
AID772809Neuroprotective activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide release at 30 uM after 20 to 24 hrs by Griess assay relative to control2013Bioorganic & medicinal chemistry, Oct-01, Volume: 21, Issue:19
N-substituted 8-aminopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecanes as σ receptor ligands with potential neuroprotective effects.
AID61566Compound was tested for its binding affinity towards Dopamine receptor D2 by using [3H]domperidone as radioligand1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID493017Wombat Data for BeliefDocking1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's8 (38.10)18.2507
2000's4 (19.05)29.6817
2010's6 (28.57)24.3611
2020's3 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.48

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

MetricThis Compound (vs All)
Research Demand Index11.48 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.48)

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%
Other21 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]