KETANSERIN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC C02KD01
UNII 97F9DE4CT4
EPA CompTox DTXSID3023188

Structure

InChI Key FPCCSQOGAWCVBH-UHFFFAOYSA-N
Smiles O=C(c1ccc(F)cc1)C1CCN(CCn2c(=O)[nH]c3ccccc3c2=O)CC1
InChI
InChI=1S/C22H22FN3O3/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29/h1-8,16H,9-14H2,(H,24,29)

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H22FN3O3
Molecular Weight 395.43
AlogP 2.42
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 75.17
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0
Assay Description Organism Bioactivity Reference
Binding affinity by displacement to human cloned 5-hydroxytryptamine 1D receptor in CHO cells by [3H]5-HT displacement. None 260.0 nM
Displacement of [3H]5-HT binding to cloned human 5-hydroxytryptamine 1D receptor stably expressed in CHO cells None 270.0 nM
Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptamine 2C receptor binding site by using [3H]-MES as a radioligand. Sus scrofa 100.0 nM
Binding affinity against 5-hydroxytryptamine 1C receptor in rat using [3H]mesulergine as radioligand Rattus norvegicus 50.0 nM
Binding affinity at serotonin 5-hydroxytryptamine 2 receptor by [3H]ketanserin displacement. None 2.0 nM
Inhibition of binding of radioligand [3H]ketanserin to 5-hydroxytryptamine 2 receptor in rat cerebral cortex None 1.2 nM
In vitro binding affinity measured on serotonin 5-hydroxytryptamine 2 receptor using [3H]ketanserin as radioligand. None 1.2 nM
Inhibition of [3H]spiperone binding to 5-hydroxytryptamine 2 receptor from rat cortical membranes None 1.7 nM
Binding affinity for membrane-bound 5-hydroxytryptamine 2 receptor None 0.42 nM
Binding affinity against 5-hydroxytryptamine 2 receptor in rat brain using [3H]ketanserin as radioligand None 3.4 nM
In vitro antagonistic activity tested against the contraction induced by 5-HT through 5-hydroxytryptamine 2 receptor in rat thoracic aortic strips None 2.512 nM
Tested for 5-hydroxytryptamine 2 receptor binding ability by displacement of [3H]spiperone from rat brain frontal cortex synaptosomes None 5.012 nM
Binding affinity at 5-hydroxytryptamine 2 receptor was determined using [125I]- DOI as radioligand in rat frontal cortex None 2.4 nM
Binding affinity at [3H]DOB labeled sites of 5-hydroxytryptamine 2 receptor determined using [125I]- DOI as radioligand in rat frontal cortex None 1.3 nM
Binding affinity at [3H]KET labeled sites of 5-hydroxytryptamine 2 receptor was determined using [125I]- DOI as radioligand in rat frontal cortex None 1.2 nM
Binding affinity against 5-hydroxytryptamine 2 receptor in rat using [3H]ketanserin as radioligand None 3.5 nM
Binding affinity against 5-hydroxytryptamine 2 receptor of rat frontal cortex using [3H]ketanserin radioligand None 1.2 nM
Binding affinity for 5-hydroxytryptamine 2 receptor from striata of male Wistar rats by displacement of [3H]ketanserin Rattus norvegicus 0.66 nM
Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 receptor binding site by using [3H]- DOB as a radioligand Rattus norvegicus 1.0 nM
Evaluated for the binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 receptor binding site by using [3H]- KET as a radioligand. None 0.4 nM
Binding affinity to 5-hydroxytryptamine 2 receptor in rat frontal cortical membranes by [3H]- KET displacement. None 1.0 nM
Percentage specific displacement of radioligand [3H]-ketanserin from 5-hydroxytryptamine 2 receptor None 34.0 nM
Binding affinity at 5-hydroxytryptamine 2 receptor from striata wistar rats by [3H]ketanserin displacement. None 0.66 nM l-1 hr-1
In vitro antagonistic activity against the contraction induced by 5-HT through 5-hydroxytryptamine 2 receptor in rat thoracic aortic strips None 96.0 %
In vivo inhibitory activity of 10 mg/kg compound in rats against elevation of BP caused by 5-HT (300 ug/kg, iv) through 5-hydroxytryptamine 2 receptor 3h after oral administration None 100.0 %
In vivo inhibitory activity of 3 mg/kg compound in rats against elevation of BP caused by 5-HT (300 ug/kg, iv) through 5-hydroxytryptamine 2 receptor 1 hr after oral administration None 96.0 %
In vivo inhibitory activity of 3 mg/kg compound in rats against elevation of BP caused by 5-HT (300 ug/kg, iv) through 5-hydroxytryptamine 2 receptor 3h after oral administration None 84.0 %
Inhibitory constant on 5-hydroxytryptamine 2A receptor of Rat frontal cortex None 5.129 nM
Binding affinity against the site labelled by the 5-hydroxytryptamine 2A receptor - 5-hydroxytryptamine 2C receptor antagonist [3H]- ketanserin None 1.37 nM
Binding affinity towards rat 5-hydroxytryptamine 2A receptor was evaluated using [3H]- ketanserin as radioligand None 3.4 nM
Displacement of [3H]- Ketanserin from rat cortex 5-hydroxytryptamine 2A receptor Rattus norvegicus 1.5 nM
Negative log concentration of antagonist on 5-hydroxytryptamine 2A receptor in rat thoracic aorta None 1.349 nM
Inhibitory constant was determined on 5-hydroxytryptamine 2C receptor of Bovine choroid plexus Bos taurus 43.65 nM
In vivo inhibitory activity in rats against elevation of blood pressure caused by phenylephrine (30 ug/kg, iv) through Alpha-1 adrenergic receptor, after 1 hr oral administration at dose of 10 mg/kg None 80.0 %
Antagonism against Alpha-1 adrenergic receptor of rat aorta None 8.128 nM
In vitro antagonistic activity tested against the contraction induced by phenylephrine through Alpha-1 adrenergic receptor in rat thoracic aortic strips None 15.85 nM
Ability to displace [3H]-Prazosin binding to Alpha-1 adrenergic receptor None 3.5 nM l-1 hr-1
Inhibition of [3H]prazosin binding to alpha-1 adrenergic receptor from rat cortical membranes None 15.0 nM
Binding affinity towards human dopamine receptor D4 None 3.5 nM
Binding affinity for Dopamine receptor D2 by displacement of [3H]-spiperone None 240.0 nM
Competitive binding assay against Dopamine receptor D2 in rat striatal membranes and [125I]-IBF radioligand Rattus norvegicus 491.0 nM
Inhibitory constant against binding of [125I]- IBZM to rat striatal membrane None 359.0 nM
Antagonism against H1 histamine receptor of guinea pig ileum Cavia porcellus 1.413 nM
In vitro anti-platelet activity was determined by the inhibition of 5-HT plus collagen-induced platelet aggregation of rabbit platelet-rich plasma Oryctolagus cuniculus 26.0 nM
Inhibitory concentration against 5-HT in conscious spontaneously hypersensitive rats (SHR) Rattus norvegicus 27.8 nM
Inhibitory concentration against phenylephrine in conscious spontaneously hypersensitive rats (SHR) Rattus norvegicus 5.73 nM
In vivo inhibitory activity in rats against elevation of blood pressure caused by 5-HT (300 ug/kg, iv) through 5-HT2 receptor after 3h of oral administration at the dose of 3 mg/kg Rattus norvegicus 46.0 %
The compound was evaluated for the percentage inhibition in rat aorta stimulated with 30 uM 5-HT and tested at fixed concentration of 10 uM Rattus norvegicus 90.0 %
Tested for the antagonistic activity against serotonin-induced contractions in rat aorta ring strip of endothelium Rattus norvegicus 1.349 nM
Compound was evaluated for its activity at membrane-bound receptor (M+L+P fraction) from rat frontal cortex Rattus norvegicus 2.63 nM
Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solubilized preparation) from rat frontal cortex Rattus norvegicus 7.943 nM
Compound was evaluated for its activity at membrane-bound receptor (M+L+P fraction) from rat frontal cortex Rattus norvegicus 0.68 nM
Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solubilized preparation) from rat frontal cortex Rattus norvegicus 3.97 nM
Value was obtained against serotonin-induced (5-HT2A) contractions in rat aorta rings Rattus norvegicus 1.349 nM
Antagonism of 5-HT2A receptor of rat tail artery Rattus norvegicus 0.2818 nM
The compound was tested for affinity towards sigma-3 receptor None 1.0 nM
In vivo inhibitory activity in rats against elevation of blood pressure caused by 5-HT (300 ug/kg, iv) through 5-HT2 receptor after 1 hr of oral administration at the dose of 3 mg/kg None 52.0 %
In vivo inhibitory activity in rats against elevation of blood pressure caused by phenylephrine (30 ug/kg, iv) through alpha-1 receptor after 1 hr of oral administration at the dose of 10 mg/kg None 91.0 %
The inhibition of compound was measured for 5 min in head twitches of mice induced by 5-HTP(100 mg/kg, ip) at the dose of 10 mg/kg Mus musculus 100.0 %
The inhibition of compound was measured for 5 min in head twitches of mice induced by 5-HTP(100 mg/kg, ip) at the dose of 3 mg/kg Mus musculus 92.0 %
The inhibition of compound was measured for 8 min in head twitches of mice induced by 5-HTP(100 mg/kg, ip) at the dose of 0.1 mg/kg Mus musculus 49.0 %
The inhibition of compound was measured for 8 min in head twitches of mice induced by 5-HTP(100 mg/kg, ip) at the dose of 0.3 mg/kg Mus musculus 88.0 %
The inhibition of compound was measured for 8 min in head twitches of mice induced by 5-HTP(100 mg/kg, ip) at the dose of 1 mg/kg Mus musculus 93.0 %
Percent inhibition against 5-hydroxytryptamine 2C receptor at 1 uM Homo sapiens 2.7 nM
Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley cortex membrane Rattus norvegicus 3.5 nM
Displacement of [3H]ketanserin from 5HT2A receptor in rat cortex membrane Rattus norvegicus 0.49 nM
Displacement of [3H]ketanserin from 5HT2 receptor None 0.4 nM
Inhibition of human 5HT2A receptor Homo sapiens 13.0 nM
Antagonist activity at serotonin 5HT2A receptor assessed as effect on 5HT-induced isometric contractile force in isolated rings of pig coronary artery Sus scrofa 1.318 nM
Displacement of radiolabeled ketanserin from human 5HT2A receptor Homo sapiens 1.3 nM Displacement of radiolabeled ketanserin from human 5HT2A receptor Homo sapiens 2.5 nM
Antagonist activity at human 5HT2A receptor expressed in EC80 serotonin-stimulated CHOK1 cells by calcium mobilization assay Homo sapiens 32.0 nM
Displacement of [3H]ketanserin from 5HT2A receptor expressed in NIH3T3 cells None 0.4 nM
Displacement of [3H]ketanserein from 5HT2A receptor F340L mutant expressed in NIH3T3 cells Homo sapiens 0.23 nM
Binding affinity to 5HT1A receptor None 794.33 nM
Displacement of [3H]ketanserin from 5HT2A in Sprague-Dawley rat brain cortex by liquid scintillation counting Rattus norvegicus 0.85 nM
Inhibition of human 5-HT2A receptor Homo sapiens 2.6 nM
Binding affinity to 5HT2A receptor in Sprague-Dawley rat frontal cortical homogenates after 15 mins Rattus norvegicus 0.85 nM
Displacement of [3H]ketanserin from human 5HT2A receptor Homo sapiens 0.28 nM
Displacement of [3H]ketanserin from Sprague-Dawley rat brain cortex serotonin 5-HT2A receptor after 15 mins by liquid scintillation counting Rattus norvegicus 0.85 nM
Antagonist activity at histamine H1 receptor None 2.0 nM
Antagonist activity at 5HT2A receptor None 2.0 nM
Antagonist activity at 5HT2A receptor (unknown origin) expressed in CHOK1 cells coexpressing Galpha15 assessed as inhibition of agonist-induced response incubated for 60 mins in incubator followed by 15 mins at room temperature by FLIPR assay Homo sapiens 80.0 nM
Antagonist activity at 5HT2A receptor (unknown origin) expressed in CHOK1 cells coexpressing Galpha15 assessed as inhibition of agonist-induced response at 10 uM incubated for 60 mins in incubator followed by 15 mins at room temperature by FLIPR assay relative to control Homo sapiens 99.9 %
Antagonist activity at serotonin-activated human recombinant 5HT-2A receptor expressed in HEK293 cells assessed as decrease in intracellular calcium level after 5 mins measured for 1 min by fluorescence assay Homo sapiens 1.04 nM
Binding affinity to human 5-HT2A receptor by radioligand displacement assay Homo sapiens 0.77 nM
Displacement of [3H]Lysergic acid from human recombinant 5HT2B receptor expressed in CHOK1 cells after 60 mins Homo sapiens 180.0 nM Displacement of [3H]Lysergic acid from human recombinant 5HT2B receptor expressed in CHOK1 cells after 60 mins Homo sapiens 290.0 nM
Displacement of [3H]Lysergic acid from human recombinant 5HT2B receptor expressed in CHOK1 cells at 10 uM after 60 mins relative to control Homo sapiens 42.0 %
Binding affinity to human 5-HT2A receptor by radioligand displacement assay Homo sapiens 0.49 nM Binding affinity to human 5-HT2A receptor by radioligand displacement assay Homo sapiens 0.9 nM
Displacement of [3H]ketanserin from 5-HT2A receptor in Sprague-Dawley rat frontal cortex after 15 mins Rattus norvegicus 0.47 nM
Antagonist activity at human recombinant 5-HT2A receptor assessed as inhibition of serotonin-induced inositol phosphate accumulation Homo sapiens 14.0 nM
Displacement of [3H]ketanserin from human recombinant 5-HT2A receptor expressed in HEK293 cells Homo sapiens 0.3 nM
Displacement of [3H]ketanserin from human 5-HT2A receptor expressed in HEK-293 cells Homo sapiens 0.3 nM
Antagonist activity against human recombinant 5-HT2A receptor expressed in CHOK1 cells assessed as reduction in alpha-methylserotonin-induced increase in intracellular Ca2+ levels by aequorin based radiometric and luminescence plate counting method Homo sapiens 11.0 nM
Antagonist activity at human 5-HT2A receptor assessed as inhibition of 5-HT-mediated internal calcium mobilization by FLIPR assay Homo sapiens 32.0 nM
Antagonist activity at dopamine 5HT2A receptor (unknown origin) at 10 uM Homo sapiens 99.6 %
Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley rat brain cortex incubated for 15 mins by liquid scintillation counting analysis Rattus norvegicus 0.85 nM
Displacement of [3H]ketanserin from human recombinant 5-HT2A receptor expressed in HEK293 cells Homo sapiens 0.35 nM
Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley rat brain cortex incubated for 15 mins Rattus norvegicus 0.85 nM
Inhibition of 5-HTP-induced head twitch response in ddY mouse at >=1 mg/kg, po administered 1 hr before 5-HTP injection measured after 30 mins relative to untreated control Mus musculus 80.0 %
Inhibition of (+/-)DOI-induced head twitch response in Albino Swiss mouse at 5 mg/kg, ip administered 60 mins before (+/-)DOI injection measured for 20 mins relative to untreated control Mus musculus 100.0 %
Displacement of [3H]ketanserin from human recombinant 5HT2A receptor expressed in HEK293 cells measured after 60 mins by scintillation counting method Homo sapiens 0.35 nM
Displacement of [3H]ketanserin from human recombinant 5-HT2A receptor in HEK293 cells after 60 mins by scintillation counting Homo sapiens 0.52 nM Displacement of [3H]ketanserin from human recombinant 5-HT2A receptor in HEK293 cells after 60 mins by scintillation counting Homo sapiens 0.28 nM
Displacement of [3H]DOI-HCL from 5HT2A in Sprague-Dawley rat frontal cortex membranes measured after 20 mins Rattus norvegicus 2.4 nM
Displacement of [3H]ketanserin from 5HT2A in Sprague-Dawley rat frontal cortex membranes measured after 20 mins Rattus norvegicus 1.2 nM
Displacement of [3H]ketanserin from serotonin 5-HT2A receptor in Sprague-Dawley rat brain cortex homogenates incubated for 15 mins by liquid scintillation spectrometry Rattus norvegicus 0.85 nM
Displacement of [3H]reserpine from human VMAT2 expressed in HEK293 cell membranes incubated for 60 mins by scintillation counting method Homo sapiens 353.0 nM
Displacement of [3H]DHTB from human VMAT2 expressed in HEK293 cell membranes incubated for 90 mins by microbeta scintillation counting method Homo sapiens 77.0 nM
Inhibition of human VMAT2 expressed in HEK293 cell membranes assessed as reduction in [3H[-5HT uptake pre-incubated for 10 mins before [3H[-5HT addition and measured after 6 mins Homo sapiens 180.0 nM
Inhibition of VMAT2 in C57Bl/6J mouse striatal membranes assessed as reduction in [3H[-5HT uptake pre-incubated for 10 mins before [3H[-5HT addition and measured after 8 mins Mus musculus 100.0 nM
Displacement of [125I]DOI from human 5HT2A receptor expressed in HEK293 cell membranes Homo sapiens 10.7 nM
Antagonist activity at serotonin 5-HT2A receptor (unknown origin) expressed in HEK293 cells assessed as inhibition of serotonin-induced calcium flux at 10 uM after 15 mins by calcium 4-dye based FLIPR assay relative to control Homo sapiens 100.0 %
Antagonist activity at serotonin 5-HT2A receptor (unknown origin) expressed in HEK293 cells assessed as inhibition of serotonin-induced calcium flux after 15 mins by calcium 4-dye based FLIPR assay Homo sapiens 83.7 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 13.11 %
Displacement of [3H] ketanserin from human recombinant 5-HT2A receptor measured after 60 mins by scintillation counter method Homo sapiens 0.45 nM Displacement of [3H] ketanserin from human recombinant 5-HT2A receptor measured after 60 mins by scintillation counter method Homo sapiens 0.82 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 24.02 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.152 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.21 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.21 %
Antagonist activity at human 5HT2A receptor expressed in CHO-K1 cells assessed as inhibition of 5HT-induced calcium flux at 10 uM incubated for 60 mins at 37 degC followed by 15 mins incubation at room temperature and subsequent 5HT addition by calcium 4 dye based FLIPR assay relative to control Homo sapiens 99.4 %
Antagonist activity at human 5HT2A receptor expressed in CHO-K1 cells assessed as inhibition of 5HT-induced calcium flux incubated for 60 mins at 37 degC followed by 15 mins incubation at room temperature and subsequent 5HT addition by calcium 4 dye based FLIPR assay Homo sapiens 19.6 nM

Cross References

Resources Reference
ChEBI 6123
ChEMBL CHEMBL51
DrugBank DB12465
DrugCentral 1524
FDA SRS 97F9DE4CT4
Guide to Pharmacology 88
KEGG C07464
PubChem 3822
SureChEMBL SCHEMBL34294
ZINC ZINC000000537877
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