INTEPIRDINE

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Synonyms
Status
Molecule Category UNKNOWN
UNII 2IOB2M82HY

Structure

InChI Key JJZFWROHYSMCMU-UHFFFAOYSA-N
Smiles O=S(=O)(c1ccccc1)c1cnc2c(N3CCNCC3)cccc2c1
InChI
InChI=1S/C19H19N3O2S/c23-25(24,16-6-2-1-3-7-16)17-13-15-5-4-8-18(19(15)21-14-17)22-11-9-20-10-12-22/h1-8,13-14,20H,9-12H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H19N3O2S
Molecular Weight 353.45
AlogP 2.48
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 62.3
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
Serotonin 6 (5-HT6) receptor antagonist ANTAGONIST PubMed
Protein: Serotonin 6 (5-HT6) receptor
Description: 5-hydroxytryptamine receptor 6
Organism : Homo sapiens
P50406 ENSG00000158748
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 997-997 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 3-97 - 0-1 -
Assay Description Organism Bioactivity Reference
Binding affinity to 5HT6 receptor None 0.234 nM
Displacement of [3H]LSD from human 5HT6 receptor expressed in HeLa cells Homo sapiens 10.0 nM
Antagonist activity at 5-HT6 receptor (unknown origin) Homo sapiens 0.23 nM
Displacement of [3H]LSD from human 5-HT6 receptor expressed in human HeLa cells after 1 hr by scintillation spectroscopic analysis Homo sapiens 0.17 nM Displacement of [3H]LSD from human 5-HT6 receptor expressed in human HeLa cells after 1 hr by scintillation spectroscopic analysis Homo sapiens 0.166 nM
Antagonist activity at human recombinant 5HT6 receptor expressed in CHO cells Homo sapiens 0.25 nM
Antagonist activity at 5-HT6 receptor (unknown origin) Homo sapiens 0.23 nM
Displacement of [3H]LSD from human 5-HT6R expressed in HEK293 cell membranes after 1 hr Homo sapiens 1.4 nM
Displacement of [3H]-LSD from human 5HT6R expressed in HEK293 cell membranes after 1 hr by microbeta counting method Homo sapiens 1.4 nM
Antagonist activity at 5HT6R (unknown origin) transfected in NG108-15 cells co-transfected with CAMYEL assessed as reduction in cAMP levels after 5 mins by Coelanterazine H-based BRET assay Homo sapiens 2.8 nM
Displacement of [3H]-Ketanserin from human 5HT2AR expressed in CHO-K1 cell membranes after 1.5 hrs by microbeta counting method Homo sapiens 26.0 nM
Displacement of [3H]-Raclopride from human dopamine D2L receptor expressed in HEK293 cell membranes after 1 hr by microbeta counting method Homo sapiens 997.0 nM
Binding affinity to 5HT6R (unknown origin) Homo sapiens 0.28 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 2.93 %
Displacement of [3H]Lu AE60157 from rat brain 5-HT6 receptor Rattus norvegicus 0.234 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 11.42 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.438 %
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 0.17 % 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 0.61 % 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 0.61 % 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 0.17 %
Inverse agonist activity at recombinant human 5HT6 receptor expressed in NG108-15 cells assessed as inhibition of cAMP production measured after 5 mins by BRET assay Homo sapiens 97.0 nM
Displacement of [3H]-LSD from human 5HT6R expressed in HEK293 cell membranes incubated for 1 hr by micro-beta plate reader based analysis Homo sapiens 1.4 nM
Inverse agonist activity at 5HT6R (unknown origin) expressed in 1321N1 cells co-expressing CAMYEL assessed as reduction in basal cAMP accumulation by BRET assay Homo sapiens 2.8 nM
Displacement of [3H]-8-OH-DPAT from human 5HT2A expressed in HEK293 cell membranes incubated for 1 hr by micro-beta plate reader based analysis Homo sapiens 26.0 nM
Displacement of [3H]-raclopride from human D2L expressed in CHO-K1 cell membranes incubated for 1 hr by micro-beta plate reader based analysis Homo sapiens 997.0 nM
Displacement of [3H]-LSD from human 5HT6 receptor expressed in HEK293 cell membranes measured after 1 hr by microbeta counting method Homo sapiens 1.4 nM
Antagonist activity at 5-HT6 receptor (unknown origin) expressed in NG108-15 cells assessed as reduction in cAMP level after 5 mins by BRET assay Homo sapiens 2.8 nM

Cross References

Resources Reference
ChEMBL CHEMBL1083390
DrugBank DB12680
FDA SRS 2IOB2M82HY
Guide to Pharmacology 9444
PubChem 11256720
SureChEMBL SCHEMBL1683964
ZINC ZINC000043199965
CONTENTS