eluxadoline   Click here for help

GtoPdb Ligand ID: 7691

Synonyms: JNJ-27018966 | Truberzi®
Approved drug
eluxadoline is an approved drug (FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Eluxadoline is a first-in-class, locally-acting dual μ-opioid receptor agonist and δ-opioid receptor antagonist [1-2].
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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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Click here for structure editor
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 8
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 164.63
Molecular weight 569.26
XLogP 3.86
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 COc1ccc(cc1C(=O)O)CN(C(c1ncc([nH]1)c1ccccc1)C)C(=O)C(Cc1c(C)cc(cc1C)C(=O)N)N
Isomeric SMILES COc1ccc(cc1C(=O)O)CN([C@H](c1ncc([nH]1)c1ccccc1)C)C(=O)[C@H](Cc1c(C)cc(cc1C)C(=O)N)N
InChI InChI=1S/C32H35N5O5/c1-18-12-23(29(34)38)13-19(2)24(18)15-26(33)31(39)37(17-21-10-11-28(42-4)25(14-21)32(40)41)20(3)30-35-16-27(36-30)22-8-6-5-7-9-22/h5-14,16,20,26H,15,17,33H2,1-4H3,(H2,34,38)(H,35,36)(H,40,41)/t20-,26-/m0/s1
InChI Key QFNHIDANIVGXPE-FNZWTVRRSA-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
In September 2014 the US FDA granted fast-track status to facilitate the development and expedite the review of this comound as a treatment for diarrhea-predominant irritable bowel syndrome (IBS-D). This decision was based on the results of two Phase 3 clinical studies that met their primary endpoints, showing significant improvement over placebo in both pain and diarrhea. In May 2015 the drug received full FDA marketing authorisation for IBS-D. Click here to view a list of clinical trials involving eluxadoline (using its company research code JNJ-27018966) hosted on the ClinicalTrials.gov website.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Eluxadoline acts locally in the gastrointestinal tract. Whilst the μ opioid receptor agonist action treats pain it also reduces gastric propulsion and can lead to opioid induced constipation. The concomittant δ opioid receptor antagonist action should help reduce this constipation and permit the drug to deliver relief from the symptoms of IBS-D.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)