IDALOPIRDINE

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Search structure


Synonyms	Idalopirdine LU AE-58054 LU-AE-58054 LU-AE58054 LY-483518 LY483518 Lu AE58054 Lu-ae58054 SGS-518 SGS518
Status
Molecule Category	UNKNOWN
UNII	59WCJ0YNWM


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	YBAWYTYNMZWMMJ-UHFFFAOYSA-N
Smiles	Fc1ccc2c(CCNCc3cccc(OCC(F)(F)C(F)F)c3)c[nH]c2c1
InChI	InChI=1S/C20H19F5N2O/c21-15-4-5-17-14(11-27-18(17)9-15)6-7-26-10-13-2-1-3-16(8-13)28-12-20(24,25)19(22)23/h1-5,8-9,11,19,26-27H,6-7,10,12H2

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H19F5N2O
Molecular Weight	398.38
AlogP	4.92
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	9.0
Polar Surface Area	37.05
Molecular species	BASE
Aromatic Rings	3.0
Heavy Atoms	28.0

Bioactivity

Mechanism of Action	Action	Reference
Serotonin 6 (5-HT6) receptor antagonist	ANTAGONIST	PubMed Other


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(%)
Enzyme Hydrolase	-	-	-	-	6
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor	-	-	-	1215	-
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor	-	1000	-	1-7	88-106

Assay Description	Organism	Bioactivity	Reference
Displacement of [3H]5-HT from 5-HT2C receptor (unknown origin) expressed in hamster AV12 cells	Homo sapiens	250.0 nM		Displacement of [3H]5-HT from 5-HT2C receptor (unknown origin) expressed in hamster AV12 cells	Homo sapiens	251.19 nM
Displacement of [3H]LSD from human 5-HT6 receptor expressed in hamster BHK cells after 60 mins by scintillation counting analysis	Homo sapiens	0.83 nM		Displacement of [3H]LSD from human 5-HT6 receptor expressed in hamster BHK cells after 60 mins by scintillation counting analysis	Homo sapiens	0.8318 nM
Antagonist activity at human recombinant 5HT6 receptor expressed in CHO cells	Homo sapiens	0.83 nM
Antagonist activity at 5-HT6 receptor (unknown origin)	Homo sapiens	0.83 nM
Binding affinity to 5HT6R (unknown origin)	Homo sapiens	0.83 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	0.53 %
Displacement of [3H]-LSD from human 5-HT6R expressed in HEK293 cells after 1 hr by microbeta plate reader analysis	Homo sapiens	3.54 nM
Binding affinity to human 5-HT2AR expressed in HEK293 cells by competitive binding assay	Homo sapiens	791.0 nM
Displacement of [3H]Lu AE60157 from rat brain 5-HT6 receptor	Rattus norvegicus	0.83 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	5.066 %
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	0.02 %		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	0.02 %
Inhibition of human erythrocyte AChE at 10^-6 M using acetylthiocholine iodide as substrate peincubated for 5 mins followed by substrate addition by DTNB-reagent based Ellman's method relative to control	Homo sapiens	6.0 %
Displacement of [3H]-LSD from human 5HT6 receptor expressed in HEK293 cell membrane at 10^-6 M measured after 60 mins relative to control	Homo sapiens	106.0 %
Displacement of [3H]-LSD from human 5HT6 receptor expressed in HEK293 cell membrane at 10^-5 M measured after 60 mins relative to control	Homo sapiens	88.0 %
Displacement of [3H]-LSD from human 5HT6 receptor expressed in HEK293 cell membrane measured after 60 mins	Homo sapiens	6.9 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL3286580
DrugBank	DB11957
FDA SRS	59WCJ0YNWM
Guide to Pharmacology	8689
PubChem	21071390
SureChEMBL	SCHEMBL762762
ZINC	ZINC000095936819

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).