JNJ-42165279   Click here for help

GtoPdb Ligand ID: 9012

Synonyms: Example 1 [WO2011139951 A1] [3] | JNJ42165279
Compound class: Synthetic organic
Comment: JNJ-42165279 is an investigational, covalent and selective inhibitor of fatty acid amide hydrolase (FAAH) [3]. Preclinical test findings are reported in [2], with the conclusion that the favourable ADME and pharmacodynamic profiles of JNJ-42165279 supported it being progressed to 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 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 66.93
Molecular weight 410.1
XLogP 1.98
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(N1CCN(CC1)Cc1ccc2c(c1)OC(O2)(F)F)Nc1cnccc1Cl
Isomeric SMILES O=C(N1CCN(CC1)Cc1ccc2c(c1)OC(O2)(F)F)Nc1cnccc1Cl
InChI InChI=1S/C18H17ClF2N4O3/c19-13-3-4-22-10-14(13)23-17(26)25-7-5-24(6-8-25)11-12-1-2-15-16(9-12)28-18(20,21)27-15/h1-4,9-10H,5-8,11H2,(H,23,26)
InChI Key YWGYNGCRVZLMCS-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Two Phase 2 clinical trials evaluating JNJ-42165279 in patients with depressive disorder and anxiety (NCT02498392), or phobic disorders (NCT02432703) were suspended as a precaution, following the BIA 10-2474 Phase 1 trial disaster in France in January 2016 (link to Janssen's statement regarding trial suspensions).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
FAAH is a serine hydrolase enzyme of the endocannabinoid system which is responsible for the catabolic inactivation of the neuromodulator anandamide. FAAH inhibitors cause a build up of anandamide, which acts through activation of cannabinoid receptors to promote analgesia, and may have anti-inflammatory action [5] and prove beneficial in managing psychiatric disorders [1,4].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02432703 A Safety and Efficacy Study of JNJ-42165279 in Participants With Social Anxiety Disorder Phase 2 Interventional Janssen Research & Development, LLC
NCT02498392 An Efficacy, Safety and Tolerability Study of JNJ-42165279 in Participants With Major Depressive Disorder With Anxious Distress Phase 2 Interventional Janssen Research & Development, LLC