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4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanol

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Description

4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119265
CHEMBL ID1036
CHEBI ID177583
SCHEMBL ID4540106
MeSH IDM0121028

Synonyms (39)

Synonym
34104-67-1
CHEMBL1036 ,
MLS001148158
4-(4-chlorophenyl)-1-[4-(4-luorophenyl)-4-hydroxybutyl]piperidin-4-ol
CHEBI:177583
mfcd00055102
haloperidol metabolite ii
MLS000069356 ,
r 2572
4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-hydroxy-butyl]piperidin-4-ol
hydroxy-haloperidol
1-piperidinebutanol, 4-(4-chlorophenyl)-.alpha.-(4-fluorophenyl)-4-hydroxy-(r/s)
smr000058675
hydroxyhaloperidol
4-(4-chloro-phenyl)-1-[4-(4-fluoro-phenyl)-4-hydroxy-butyl]-piperidin-4-ol
bdbm50064946
4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-hydroxybutyl]piperidin-4-ol
NCGC00018116-02
1-piperidinebutanol, 4-(4-chlorophenyl)-alpha-(4-fluorophenyl)-4-hydroxy-
reduced haloperidol
unii-d9m1q7kw8u
4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanol
d9m1q7kw8u ,
HMS2234D04
FT-0674336
HMS3372K12
SCHEMBL4540106
1-(p-fluorophenyl)-4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-1 -butanol
1-(p-fluorophenyl)-4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-1-butanol
1-piperidinebutanol, 4-(4-chlorophenyl)-.alpha.-(4-fluorophenyl)-4-hydroxy-
dihydrohaloperidol
OPERA_ID_1804
haloperidol metabolite ii, analytical standard
4-(4-chlorophenyl)-alpha-(4-fluorophenyl)-4-hydroxy-1-piperidinebutanol
J-019450
DTXSID80929321
4-(4-chlorophenyl)-.alpha.-(4-fluorophenyl)-4-hydroxy-1-piperidinebutanol
r-2572
AKOS040755657

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" These data were used to determine the pharmacokinetic factor(s) that correlate best with HL and RHL concentrations in hair."( Steady-state pharmacokinetics of haloperidol and reduced haloperidol in schizophrenic patients: analysis of factors determining their concentrations in hair.
Hasegawa, K; Hirayama, H; Matsuno, H; Nakashima, M; Sato, H; Uematsu, T, 1992
)
0.28
" The mean elimination half-life of 54."( Pharmacokinetics of haloperidol and reduced haloperidol in Chinese schizophrenic patients after intravenous and oral administration of haloperidol.
Chang, WH; Chen, H; Jann, MW; Lam, YW, 1992
)
0.28

Bioavailability

ExcerptReferenceRelevance
" After oral dosing, bioavailability of haloperidol was 35 +/- 8%, suggesting extensive first pass metabolism."( Pharmacokinetics of haloperidol and reduced haloperidol in Chinese schizophrenic patients after intravenous and oral administration of haloperidol.
Chang, WH; Chen, H; Jann, MW; Lam, YW, 1992
)
0.28

Dosage Studied

ExcerptRelevanceReference
" HD dosage was highly correlated with both RBC H and plasma H, but RBC RH and plasma RH were not significantly related to dosage at any time point."( Haloperidol decanoate pharmacokinetics in red blood cells and plasma.
Dysken, MW; Holden, L; Johnson, SB; Kim, SW; Skare, S; Thomsyck, L; Vatassery, G, 1992
)
0.28
" In addition, the polymorphic distribution of RH/HL ratios, suggested by previous investigators, was further tested in each dosage group (for controlling the potential dosage effect on RH/HL ratios)."( Dose-dependent reduced haloperidol/haloperidol ratios: influence of patient-related variables.
Chang, WH; Chang, YC; Hu, OY; Hu, WH; Jann, MW; Lane, HY; Lin, HN, 1997
)
0.3
" Sixteen patients who did not respond to the traditional antipsychotics after 2 weeks of treatment with a certain dosage of haloperidol were administered with 50 mg of sertraline for a period of 2 weeks."( Co-administration of sertraline and haloperidol.
Han, CS; Kim, SH; Lee, MS; You, YW, 1998
)
0.3
[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]

Pathways (1)

PathwayProteinsCompounds
Haloperidol Pathway, Pharmacokinetics115

Protein Targets (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency0.03980.044717.8581100.0000AID485294
glp-1 receptor, partialHomo sapiens (human)Potency10.00000.01846.806014.1254AID624417
ATAD5 protein, partialHomo sapiens (human)Potency5.80480.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency22.72650.000811.382244.6684AID686978; AID686979
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency89.12510.035520.977089.1251AID504332
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency20.59620.00419.984825.9290AID504444
importin subunit beta-1 isoform 1Homo sapiens (human)Potency0.25935.804836.130665.1308AID540253
snurportin-1Homo sapiens (human)Potency0.25935.804836.130665.1308AID540253
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency0.25935.804816.996225.9290AID540253
gemininHomo sapiens (human)Potency13.03740.004611.374133.4983AID624296; AID624297
lamin isoform A-delta10Homo sapiens (human)Potency15.84890.891312.067628.1838AID1487
[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)
D(2) dopamine receptorHomo sapiens (human)Ki0.09120.00000.651810.0000AID1616723
D(3) dopamine receptorRattus norvegicus (Norway rat)Ki1.02400.00010.25675.8000AID1686279
D(2) dopamine receptorRattus norvegicus (Norway rat)Ki0.24100.00000.437510.0000AID1686278
Sigma intracellular receptor 2Rattus norvegicus (Norway rat)Ki0.00240.00241.10509.3000AID1877931
Sigma non-opioid intracellular receptor 1Cavia porcellus (domestic guinea pig)Ki0.00280.00000.338510.0000AID1686276; AID1809442; AID1877932
[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)Kd0.09120.00000.64599.5000AID1616723
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (97)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (81)

Assay IDTitleYearJournalArticle
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
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.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
AID234273Selectivity is determined by the ratio of Ki for rat sigma 2 receptor to that of guinea pig sigma-1 receptor2001Journal of medicinal chemistry, Dec-06, Volume: 44, Issue:25
Synthesis and structure-activity relationships of N-(1-benzylpiperidin-4-yl)arylacetamide analogues as potent sigma1 receptor ligands.
AID1189669Induction of cell cycle arrest in rat C6 cells assessed as increase in accumulation at S phase after 72 hrs by propidium iodide staining based flow cytometry2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1877931Displacement of [3H]-DTG from Sprague-Dawley rat liver Sigma 2 receptor incubated for 120 mins in presence of [3H]-(+)-pentazocine by liquid scintillation counting analysis2022European journal of medicinal chemistry, Feb-15, Volume: 230Dual Sigma-1 receptor antagonists and hydrogen sulfide-releasing compounds for pain treatment: Design, synthesis, and pharmacological evaluation.
AID1686276Displacement of [3H]-pentazocine from sigma1 receptor in guinea pig brain membranes by scintillation counting2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189672Inhibition of HDAC in rat C6 cells assessed as increase in histone H3 acetylation at 5 uM after 15 hrs by flow cytometry2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1809444Antiproliferative activity against VEGF-A stimulated human retinal endothelial cell assessed as reduction in cell viability measured after 24 hrs by MTT assay2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
AID1189667Induction of cell cycle arrest in rat C6 cells assessed as accumulation at S phase after 24 and 48 hrs by propidium iodide staining based flow cytometry2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID226340Binding affinity for sigma 2 opioid receptor, measured on rat liver membranes using [3H]- DTG as radioligand in the presence of (+)-pentazocine2001Journal of medicinal chemistry, Dec-06, Volume: 44, Issue:25
Synthesis and structure-activity relationships of N-(1-benzylpiperidin-4-yl)arylacetamide analogues as potent sigma1 receptor ligands.
AID1686297Effect on cell migration of in HREC at 5 uM incubated for 24 to 72 hrs by wound healing assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1809448Antiangiogenic activity against VEGF-A stimulated human retinal endothelial cell assessed as cell proliferation measured after 48 hrs by crystal violet assay2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
AID1809442Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain membranes after 150 mins by microbeta scintillation counting method2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
AID566435Antiproliferative activity against human PC3 cells after 24 hrs by MTT assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells.
AID1686290Cytotoxicity in HREC assessed as reduction in cell viability at 20 uM incubated for 72 hrs in presence of 1 uM sigma2 receptor antagonist AC927 by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID566430Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in guinea pig brain membrane after 150 mins by liquid scintillation counting2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells.
AID1877932Displacement of [3H]-(+)-pentazocine from Dunkin-Hartley guinea pig brain cortex Sigma 1 receptor incubated for 150 mins by liquid scintillation counting analysis2022European journal of medicinal chemistry, Feb-15, Volume: 230Dual Sigma-1 receptor antagonists and hydrogen sulfide-releasing compounds for pain treatment: Design, synthesis, and pharmacological evaluation.
AID1686299Suppression of VEGF-A-induced cell migration in HREC assessed as crossing cells count at 5 uM incubated for 72 hrs by wound healing assay (Rvb = 26%)2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1616723Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes by TR-FRET assay
AID1686283Cytotoxicity in HREC assessed as reduction in cell viability incubated for 96 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189658Displacement of [3H]-DTG from sigma 2 receptor guinea pig brain membranes incubated for 120 mins by scintillation counting method2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1686289Cytotoxicity in HREC assessed as reduction in cell viability at 20 uM incubated for 72 hrs in presence of 1 uM sigma1 selective agonist (+)-pentazocine by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1686282Cytotoxicity in HREC assessed as reduction in cell viability incubated for 72 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1686281Cytotoxicity in HREC assessed as reduction in cell viability incubated for 48 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1686284Cytotoxicity in HREC assessed as reduction in cell viability by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1686279Displacement of [3H]-7-OH-DPAT from DRD3 in rat olfactory tubercle by scintillation counting2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189664Cytotoxicity against rat C6 cells assessed as reduction in cell viability at 0.1 to 5 uM after 48 hrs by MTT assay2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1809445Antiproliferative activity against VEGF-A stimulated human retinal endothelial cell assessed as reduction in cell viability measured after 48 hrs by MTT assay2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
AID1616720Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes assessed as association rate constant by TR-FRET assay
AID566434Antiproliferative activity against human LNCAP cells after 24 hrs by MTT assay2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells.
AID203685Binding affinity against sigma-1 receptor in guinea pig brain membranes using [3H](+)-pentazocine as the radioligand1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Synthesis and quantitative structure-activity relationships of N-(1-benzylpiperidin-4-yl)phenylacetamides and related analogues as potent and selective sigma1 receptor ligands.
AID1686298Suppression of VEGF-A-induced cell migration in HREC assessed as crossing cells count at 5 uM incubated for 24 hrs by wound healing assay (Rvb = 63%)2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189666Induction of cell cycle arrest in rat C6 cells assessed as accumulation at G1 phase after 24 and 48 hrs by propidium iodide staining based flow cytometry2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1686280Cytotoxicity in HREC assessed as reduction in cell viability incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1686295Suppression of VEGF-A-induced pro-angiogenesis in HREC assessed as alive cell number count at 5 uM incubated for 24 hrs by Trypan blue dye exclusion assay (Rvb = 52%)2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189670Antimigratory activity against rat C6 cells assessed as cell migration level at 5 uM after 24 hrs by transwell chamber assay (Rvb = 60%)2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1616722Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes assessed as dissociation half-life by TR-FRET assay
AID566432Displacement radioligand form dopamine D2 receptor in rat striatum by liquid scintillation counting2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells.
AID566433Displacement radioligand form dopamine D3 receptor in rat olfactory tubercle by liquid scintillation counting2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells.
AID226337Binding affinity for sigma 1 opioid receptor, measured on guinea pig brain membranes using [3H]- (+)-pentazocine as radioligand2001Journal of medicinal chemistry, Dec-06, Volume: 44, Issue:25
Synthesis and structure-activity relationships of N-(1-benzylpiperidin-4-yl)arylacetamide analogues as potent sigma1 receptor ligands.
AID1686296Suppression of VEGF-A-induced pro-angiogenesis in HREC assessed as alive cell number count at 5 uM incubated for 72 hrs by Trypan blue dye exclusion assay (Rvb = 42%)2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189671Inhibition of HDAC in rat C6 cells assessed as increase in histone H3 acetylation at 5 uM after 6 hrs by flow cytometry (Rvb = 4.5%)2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID1809449Antiangiogenic activity against VEGF-A stimulated Human endothelial cell assessed as cell proliferation measured after 72 hrs by crystal violet assay2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
AID1686293Cytotoxicity in HREC assessed as reduction in cell counts at 5 uM incubated for 24 hrs under basal conditions by Trypan blue dye exclusion assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1686288Cytotoxicity in HREC assessed as reduction in cell viability at 20 uM incubated for 72 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID203845Binding affinity towards sigma 2 receptor site in rat liver membranes using [3H]DTG as radioligand in presence of (+)-pentazocine.1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Synthesis and quantitative structure-activity relationships of N-(1-benzylpiperidin-4-yl)phenylacetamides and related analogues as potent and selective sigma1 receptor ligands.
AID203850Selectivity ratio for sigma 2 receptor site in rat liver membranes and sigma 1 receptor site in quinea pig brain membranes1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Synthesis and quantitative structure-activity relationships of N-(1-benzylpiperidin-4-yl)phenylacetamides and related analogues as potent and selective sigma1 receptor ligands.
AID1809443Displacement of [3H](+)-pentazocine from sigma 2 receptor in guinea pig brain membranes after 120 mins by microbeta scintillation counting method2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
AID1686294Cytotoxicity in HREC assessed as reduction in cell counts at 5 uM incubated for 72 hrs under basal conditions by Trypan blue dye exclusion assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1809446Antiproliferative activity against VEGF-A stimulated human retinal endothelial cell assessed as reduction in cell viability measured after 72 hrs by MTT assay2021Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18
Haloperidol Metabolite II Valproate Ester (
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
AID1686285Cytotoxicity in HREC assessed as reduction in cell viability at 200 uM incubated for 24 hrs by MTT assay2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID1189668Induction of cell cycle arrest in rat C6 cells assessed as accumulation at G2/M phase after 24 and 48 hrs by propidium iodide staining based flow cytometry2015European journal of medicinal chemistry, Jan-27, Volume: 90Haloperidol metabolite II prodrug: asymmetric synthesis and biological evaluation on rat C6 glioma cells.
AID566431Displacement of [3H]DTG from sigma 2 receptor in guinea pig brain membrane after 120 mins by liquid scintillation counting2011European journal of medicinal chemistry, Jan, Volume: 46, Issue:1
Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells.
AID1616721Displacement of PPHT-red from SNAP-tagged human D2LR expressed in CHOK1 cell membranes assessed as dissociation rate constant by TR-FRET assay
AID1686277Displacement of [3H]-DTG from sigma2 receptor in guinea pig brain membranes by scintillation counting2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
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
AID1686278Displacement of [3H]-spiperone from DRD2 in rat striatum by scintillation counting2016Journal of medicinal chemistry, 11-10, Volume: 59, Issue:21
Antiangiogenic Effect of (±)-Haloperidol Metabolite II Valproate Ester [(±)-MRJF22] in Human Microvascular Retinal Endothelial Cells.
AID504796Counterscreen for activators of the Protein Kinase A-R2B (PKA-R2B) complex: fluorescence polarization-based biochemical high throughput screening assay to identify fluorescence polarization assay artifacts2006Analytical chemistry, Dec-15, Volume: 78, Issue:24
Assay principle for modulators of protein-protein interactions and its application to non-ATP-competitive ligands targeting protein kinase A.
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.
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.
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
AID504797Fluorescence polarization-based biochemical high throughput confirmation assay for activators of the Protein Kinase A-R2B (PKA-R2B) complex2006Analytical chemistry, Dec-15, Volume: 78, Issue:24
Assay principle for modulators of protein-protein interactions and its application to non-ATP-competitive ligands targeting protein kinase A.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (10.29)18.7374
1990's37 (54.41)18.2507
2000's10 (14.71)29.6817
2010's9 (13.24)24.3611
2020's5 (7.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.65

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 Index10.65 (24.57)
Research Supply Index4.42 (2.92)
Research Growth Index5.07 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (17.14%)5.53%
Reviews1 (1.43%)6.00%
Case Studies1 (1.43%)4.05%
Observational0 (0.00%)0.25%
Other56 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]