UE2343   Click here for help

GtoPdb Ligand ID: 12037

Synonyms: compound 4 [PMID: 28012176] | UE-2343 | Xanamem®
Compound class: Synthetic organic
Comment: UE2343 is an oral, brain-penetrant hydroxysteroid 11-beta dehydrogenase 1 (11-βHSD1) inhibitor that was developed to reduce brain levels of the stress hormone cortisol, as a mechanism to improve memory in Alzheimer's disease patients [1-2]. It failed to provide efficacy in a phase 2 clinical trial.
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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 CDK toolkit. 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 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 123.24
Molecular weight 381.13
XLogP 0.85
No. Lipinski's rules broken 0
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.

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Canonical SMILES O=C(N1[C@@H]2CC[C@H]1CC(C2)(O)c1ncccn1)c1csc(c1)c1c[nH]nc1
Isomeric SMILES C1C[C@H]2CC(C[C@@H]1N2C(=O)c1csc(c1)c1c[nH]nc1)(c1ncccn1)O
InChI InChI=1S/C19H19N5O2S/c25-17(12-6-16(27-11-12)13-9-22-23-10-13)24-14-2-3-15(24)8-19(26,7-14)18-20-4-1-5-21-18/h1,4-6,9-11,14-15,26H,2-3,7-8H2,(H,22,23)/t14-,15+,19?
InChI Key MMZFGTAMARVHAF-RTHVDDQRSA-N
No information available.
Summary of Clinical Use Click here for help
UE2343 was advanced to clinical trial, to evaluate its potential efficacy in patients with mild Alzheimer's disease.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02727699 A Phase II Study to Assess the Safety, Tolerability and Efficacy of Xanamem™ in Subjects With Mild Dementia Due to AD (XanADu) Phase 2 Interventional Actinogen Medical The results from this study have been posted on ClinicalTrials.gov. UE2343 (Xanamen®) failed to show clinical benefit in patients with mild Alzheimer's dementia when compared to placebo.