Page last updated: 2024-11-08

4(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydropyridine

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Description

4(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydropyridine: metabolite of haloperidol; much less potent neuroleptic agent than haloperidol; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID171187
CHEMBL ID3544895
CHEBI ID177523
SCHEMBL ID11793421
MeSH IDM0265109

Synonyms (26)

Synonym
CHEBI:177523
4-(4-(p-chlorophenyl)-2,5,6-trihydropyridino)-4'-fluorobutyrophenone
52669-92-8
4-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-1-(4-luorophenyl)butan-1-one
1-butanone, 4-(4-(4-chlorophenyl)-3,6-dihydro-1(2h)-pyridinyl)-1-(4-fluorophenyl)-
clp-fp-ob-thp
4-(4-(4-chlorophenyl)-3,6-dihydro-1(2h)-pyridinyl)-1-(4-fluorophenyl)-1-butanone
4-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-1-(4-fluorophenyl)butan-1-one
4(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydropyridine
unii-59ir9l62qf
59ir9l62qf ,
haloperidol tetrahydropyridine
hptp
SCHEMBL11793421
4-(4-(4-chlorophenyl)-3,6-dihydro-1(2h)-pyridinyl)-1-(4-fluorophenyl)-1-butanone #
ZNOLNAPJKOYTHY-UHFFFAOYSA-N
1-butanone, 4-[4-(4-chlorophenyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-(4-fluorophenyl)-
CHEMBL3544895 ,
DTXSID80200642
4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydropyridine
haloperidol 1,2,3,6-tetrahydropyridine
4-[4-(4-chlorophenyl)-3,6-dihydro-1(2h)-pyridinyl]-1-(4-fluorophenyl)-1-butanone
4-(4-(4-chlorophenyl)-5,6-dihydropyridin-1(2h)-yl)-1-(4-fluorophenyl)butan-1-one hydrochloride
Q27261705
4-[4-(4-chlorophenyl)-3,6-dihydropyridin-1(2h)-yl]-1-(4-fluorophenyl)butan-1-one
bdbm50530692
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic ring.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
D(2) dopamine receptorHomo sapiens (human)Ki0.01000.00000.651810.0000AID1616723
N-acetyltransferase EisMycobacterium tuberculosis H37RvIC50 (µMol)0.56000.39001.64255.1000AID1853637
[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)
D(2) dopamine receptorHomo sapiens (human)Kd0.01000.00000.64599.5000AID1616723
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (98)

Processvia Protein(s)Taxonomy
phospholipase C-activating dopamine receptor signaling pathwayD(2) dopamine receptorHomo sapiens (human)
temperature homeostasisD(2) dopamine receptorHomo sapiens (human)
response to hypoxiaD(2) dopamine receptorHomo sapiens (human)
negative regulation of protein phosphorylationD(2) dopamine receptorHomo sapiens (human)
response to amphetamineD(2) dopamine receptorHomo sapiens (human)
nervous system process involved in regulation of systemic arterial blood pressureD(2) dopamine receptorHomo sapiens (human)
regulation of heart rateD(2) dopamine receptorHomo sapiens (human)
regulation of sodium ion transportD(2) dopamine receptorHomo sapiens (human)
G protein-coupled receptor internalizationD(2) dopamine receptorHomo sapiens (human)
positive regulation of neuroblast proliferationD(2) dopamine receptorHomo sapiens (human)
positive regulation of receptor internalizationD(2) dopamine receptorHomo sapiens (human)
autophagyD(2) dopamine receptorHomo sapiens (human)
adenylate cyclase-inhibiting dopamine receptor signaling pathwayD(2) dopamine receptorHomo sapiens (human)
neuron-neuron synaptic transmissionD(2) dopamine receptorHomo sapiens (human)
neuroblast proliferationD(2) dopamine receptorHomo sapiens (human)
axonogenesisD(2) dopamine receptorHomo sapiens (human)
synapse assemblyD(2) dopamine receptorHomo sapiens (human)
sensory perception of smellD(2) dopamine receptorHomo sapiens (human)
long-term memoryD(2) dopamine receptorHomo sapiens (human)
grooming behaviorD(2) dopamine receptorHomo sapiens (human)
locomotory behaviorD(2) dopamine receptorHomo sapiens (human)
adult walking behaviorD(2) dopamine receptorHomo sapiens (human)
protein localizationD(2) dopamine receptorHomo sapiens (human)
negative regulation of cell population proliferationD(2) dopamine receptorHomo sapiens (human)
associative learningD(2) dopamine receptorHomo sapiens (human)
visual learningD(2) dopamine receptorHomo sapiens (human)
response to xenobiotic stimulusD(2) dopamine receptorHomo sapiens (human)
response to light stimulusD(2) dopamine receptorHomo sapiens (human)
response to toxic substanceD(2) dopamine receptorHomo sapiens (human)
response to iron ionD(2) dopamine receptorHomo sapiens (human)
response to inactivityD(2) dopamine receptorHomo sapiens (human)
Wnt signaling pathwayD(2) dopamine receptorHomo sapiens (human)
striatum developmentD(2) dopamine receptorHomo sapiens (human)
orbitofrontal cortex developmentD(2) dopamine receptorHomo sapiens (human)
cerebral cortex GABAergic interneuron migrationD(2) dopamine receptorHomo sapiens (human)
adenohypophysis developmentD(2) dopamine receptorHomo sapiens (human)
negative regulation of cell migrationD(2) dopamine receptorHomo sapiens (human)
peristalsisD(2) dopamine receptorHomo sapiens (human)
auditory behaviorD(2) dopamine receptorHomo sapiens (human)
regulation of synaptic transmission, GABAergicD(2) dopamine receptorHomo sapiens (human)
positive regulation of cytokinesisD(2) dopamine receptorHomo sapiens (human)
circadian regulation of gene expressionD(2) dopamine receptorHomo sapiens (human)
negative regulation of dopamine secretionD(2) dopamine receptorHomo sapiens (human)
response to histamineD(2) dopamine receptorHomo sapiens (human)
response to nicotineD(2) dopamine receptorHomo sapiens (human)
positive regulation of urine volumeD(2) dopamine receptorHomo sapiens (human)
positive regulation of renal sodium excretionD(2) dopamine receptorHomo sapiens (human)
positive regulation of multicellular organism growthD(2) dopamine receptorHomo sapiens (human)
response to cocaineD(2) dopamine receptorHomo sapiens (human)
negative regulation of circadian sleep/wake cycle, sleepD(2) dopamine receptorHomo sapiens (human)
dopamine metabolic processD(2) dopamine receptorHomo sapiens (human)
drinking behaviorD(2) dopamine receptorHomo sapiens (human)
regulation of potassium ion transportD(2) dopamine receptorHomo sapiens (human)
response to morphineD(2) dopamine receptorHomo sapiens (human)
pigmentationD(2) dopamine receptorHomo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transductionD(2) dopamine receptorHomo sapiens (human)
positive regulation of G protein-coupled receptor signaling pathwayD(2) dopamine receptorHomo sapiens (human)
negative regulation of blood pressureD(2) dopamine receptorHomo sapiens (human)
negative regulation of innate immune responseD(2) dopamine receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IID(2) dopamine receptorHomo sapiens (human)
negative regulation of insulin secretionD(2) dopamine receptorHomo sapiens (human)
acid secretionD(2) dopamine receptorHomo sapiens (human)
behavioral response to cocaineD(2) dopamine receptorHomo sapiens (human)
behavioral response to ethanolD(2) dopamine receptorHomo sapiens (human)
regulation of long-term neuronal synaptic plasticityD(2) dopamine receptorHomo sapiens (human)
response to axon injuryD(2) dopamine receptorHomo sapiens (human)
branching morphogenesis of a nerveD(2) dopamine receptorHomo sapiens (human)
arachidonic acid secretionD(2) dopamine receptorHomo sapiens (human)
epithelial cell proliferationD(2) dopamine receptorHomo sapiens (human)
negative regulation of epithelial cell proliferationD(2) dopamine receptorHomo sapiens (human)
negative regulation of protein secretionD(2) dopamine receptorHomo sapiens (human)
release of sequestered calcium ion into cytosolD(2) dopamine receptorHomo sapiens (human)
dopamine uptake involved in synaptic transmissionD(2) dopamine receptorHomo sapiens (human)
regulation of dopamine uptake involved in synaptic transmissionD(2) dopamine receptorHomo sapiens (human)
positive regulation of dopamine uptake involved in synaptic transmissionD(2) dopamine receptorHomo sapiens (human)
regulation of synapse structural plasticityD(2) dopamine receptorHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionD(2) dopamine receptorHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergicD(2) dopamine receptorHomo sapiens (human)
excitatory postsynaptic potentialD(2) dopamine receptorHomo sapiens (human)
positive regulation of growth hormone secretionD(2) dopamine receptorHomo sapiens (human)
prepulse inhibitionD(2) dopamine receptorHomo sapiens (human)
negative regulation of dopamine receptor signaling pathwayD(2) dopamine receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeD(2) dopamine receptorHomo sapiens (human)
regulation of locomotion involved in locomotory behaviorD(2) dopamine receptorHomo sapiens (human)
postsynaptic modulation of chemical synaptic transmissionD(2) dopamine receptorHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionD(2) dopamine receptorHomo sapiens (human)
negative regulation of cellular response to hypoxiaD(2) dopamine receptorHomo sapiens (human)
positive regulation of glial cell-derived neurotrophic factor productionD(2) dopamine receptorHomo sapiens (human)
positive regulation of long-term synaptic potentiationD(2) dopamine receptorHomo sapiens (human)
hyaloid vascular plexus regressionD(2) dopamine receptorHomo sapiens (human)
negative regulation of neuron migrationD(2) dopamine receptorHomo sapiens (human)
negative regulation of cytosolic calcium ion concentrationD(2) dopamine receptorHomo sapiens (human)
regulation of dopamine secretionD(2) dopamine receptorHomo sapiens (human)
negative regulation of adenylate cyclase activityD(2) dopamine receptorHomo sapiens (human)
phospholipase C-activating dopamine receptor signaling pathwayD(2) dopamine receptorHomo sapiens (human)
negative regulation of voltage-gated calcium channel activityD(2) dopamine receptorHomo sapiens (human)
positive regulation of MAPK cascadeD(2) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayD(2) dopamine receptorHomo sapiens (human)
symbiont-mediated suppression of host defense-related programmed cell deathN-acetyltransferase EisMycobacterium tuberculosis H37Rv
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
dopamine neurotransmitter receptor activity, coupled via Gi/GoD(2) dopamine receptorHomo sapiens (human)
G-protein alpha-subunit bindingD(2) dopamine receptorHomo sapiens (human)
protein bindingD(2) dopamine receptorHomo sapiens (human)
heterotrimeric G-protein bindingD(2) dopamine receptorHomo sapiens (human)
dopamine bindingD(2) dopamine receptorHomo sapiens (human)
ionotropic glutamate receptor bindingD(2) dopamine receptorHomo sapiens (human)
identical protein bindingD(2) dopamine receptorHomo sapiens (human)
heterocyclic compound bindingD(2) dopamine receptorHomo sapiens (human)
G protein-coupled receptor activityD(2) dopamine receptorHomo sapiens (human)
N-acetyltransferase activityN-acetyltransferase EisMycobacterium tuberculosis H37Rv
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (22)

Processvia Protein(s)Taxonomy
Golgi membraneD(2) dopamine receptorHomo sapiens (human)
acrosomal vesicleD(2) dopamine receptorHomo sapiens (human)
plasma membraneD(2) dopamine receptorHomo sapiens (human)
ciliumD(2) dopamine receptorHomo sapiens (human)
lateral plasma membraneD(2) dopamine receptorHomo sapiens (human)
endocytic vesicleD(2) dopamine receptorHomo sapiens (human)
axonD(2) dopamine receptorHomo sapiens (human)
dendriteD(2) dopamine receptorHomo sapiens (human)
synaptic vesicle membraneD(2) dopamine receptorHomo sapiens (human)
sperm flagellumD(2) dopamine receptorHomo sapiens (human)
dendritic spineD(2) dopamine receptorHomo sapiens (human)
perikaryonD(2) dopamine receptorHomo sapiens (human)
axon terminusD(2) dopamine receptorHomo sapiens (human)
postsynaptic membraneD(2) dopamine receptorHomo sapiens (human)
ciliary membraneD(2) dopamine receptorHomo sapiens (human)
non-motile ciliumD(2) dopamine receptorHomo sapiens (human)
dopaminergic synapseD(2) dopamine receptorHomo sapiens (human)
GABA-ergic synapseD(2) dopamine receptorHomo sapiens (human)
G protein-coupled receptor complexD(2) dopamine receptorHomo sapiens (human)
glutamatergic synapseD(2) dopamine receptorHomo sapiens (human)
presynaptic membraneD(2) dopamine receptorHomo sapiens (human)
plasma membraneD(2) dopamine receptorHomo sapiens (human)
cytosolN-acetyltransferase EisMycobacterium tuberculosis H37Rv
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (18)

Assay IDTitleYearJournalArticle
AID1616720Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes assessed as association rate constant by TR-FRET assay
AID1853651Antibacterial activity against Mycobacterium intracellulare ATCC 13950 assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853644Antibacterial activity against Mycobacterium tuberculosis mc2 6230-K204 with Eis C-14T mutation inhibition of bacterial growth at 100 uM incubated for 1 week by resazurin staining based microdilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853655Antibacterial activity against Mycobacterium tuberculosis mc2 6230 with Eis C-14T mutation assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1616722Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes assessed as dissociation half-life by TR-FRET assay
AID1853693Metabolic stability in human liver microsomes at 2 to 4 uM incubated for 30 mins by LC-MS/MS analysis2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853649Antibacterial activity against Mycobacterium smegmatis mc2 155 assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1616728Antagonist activity at SNAP-tagged human D2LR expressed in Flp-In CHO cells assessed as suppression of dopamine-induced inhibition of forskolin-stimulated cAMP accumulation at 10 uM preincubated with compound followed by forskolin and dopamine addition an
AID1616723Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes by TR-FRET assay
AID1853653Antibacterial activity against Mycobacterium bovis BCG ATCC 35734 assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1616727Agonist activity at SNAP-tagged human D2LR expressed in Flp-In CHO cells assessed as inhibition of forskolin-stimulated cAMP accumulation at 10 uM measured after 10 mins in presence of coelenterazine by BRET assay relative to control
AID1853650Antibacterial activity against Mycobacterium abscessus ATCC 19977 assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1616721Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes assessed as dissociation rate constant by TR-FRET assay
AID1853643Antibacterial activity against Mycobacterium tuberculosis H37Rv mc2 6230 with Eis C-14T mutation assessed as inhibition of bacterial growth at 100 uM incubated for 1 week by resazurin staining based microdilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853694Metabolic stability in mouse liver microsomes at 2 to 4 uM incubated for 30 mins by LC-MS/MS analysis2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853637Inhibition of Mycobacterium tuberculosis Eis assessed as Eis-mediated kanamycin acetylation preincubated for 10 mins followed by substrate addition and measured for 2 to 5 mins using acetyl-CoA as substrate in presence of kanamycin by UV-Vis spectroscopy 2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853652Antibacterial activity against Mycobacterium avium ATCC 25921 assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
AID1853654Antibacterial activity against Mycobacterium tuberculosis H37Ra ATCC NRS22 assessed as inhibition of bacterial growth incubated upto 3 weeks hrs by resazurin dye based double-dilution method2021RSC medicinal chemistry, Nov-17, Volume: 12, Issue:11
Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (55.56)18.2507
2000's2 (22.22)29.6817
2010's1 (11.11)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.15

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 Index12.15 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.15)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]