idalopirdine   Click here for help

GtoPdb Ligand ID: 8689

Synonyms: compound 52 [4] | Lu AE58054 | LU-AE58054
Compound class: Synthetic organic
Comment: Idalopirdine is a serotonin 5-HT6 receptor antagonist [4].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 37.05
Molecular weight 398.14
XLogP 5.38
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Fc1ccc2c(c1)[nH]cc2CCNCc1cccc(c1)OCC(C(F)F)(F)F
Isomeric SMILES Fc1ccc2c(c1)[nH]cc2CCNCc1cccc(c1)OCC(C(F)F)(F)F
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
InChI Key YBAWYTYNMZWMMJ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Idalopirdine reached Phase 2I clinical trial as a potential augmentation therapy for the treatment of the cognitive deficits associated with Alzheimer's disease (AD) [2], being assessed in patients with mild-moderate AD who were receiving donepezil therapy. Wilkinson et al. (2014) reported encouraging results from the earlier Phase 2 trial [6]. However, the developer, Lundbeck, reported failure of the first of three Phase 2I studies (STARSHINE) to meet primary and secondary endpoints (Sept 2016), and failure of its two other Phase 2I trials (STARBEAM and STARBRIGHT) to show efficacy (Feb 2017), and that they were therefore not submitting idalopirdine for regulatory approval.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
5-HT6 receptor antagonists have been reported to improve cognitive deficit [5], and are being investigated as a novel mechanism to treat the cognitive impairment which develops in AD [1,3].