verucerfont   Click here for help

GtoPdb Ligand ID: 10378

Synonyms: Compound (S)-8d [PMID: 21074436] | GSK-561679 | GSK561679 | NBI-77860 | NBI77860
Compound class: Synthetic organic
Comment: Verucerfont (NBI-77860 or GSK561679) is an orally available, brain penetrant and selective corticotropin releasing factor-1 (CRF-1) receptor antagonist [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

verucerfont is commercially available from our sponsors

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 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 90.37
Molecular weight 406.21
XLogP 4.64
No. Lipinski's rules broken 0

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(c(c1)C)c1c(C)nn2c1nc(C)cc2NC(c1onc(n1)C)CC
Isomeric SMILES COc1ccc(c(c1)C)c1c(C)nn2c1nc(C)cc2N[C@H](c1onc(n1)C)CC
InChI InChI=1S/C22H26N6O2/c1-7-18(22-24-15(5)27-30-22)25-19-11-13(3)23-21-20(14(4)26-28(19)21)17-9-8-16(29-6)10-12(17)2/h8-11,18,25H,7H2,1-6H3/t18-/m0/s1
InChI Key VKHVAUKFLBBZFJ-SFHVURJKSA-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
Verucerfont (GSK561679) was advanced to Phase 2 clinical evaluation as a drug to combat alcohol dependence (see NCT01187511) [3]. Analysis of trial results did not identify clinical efficacy of CRF-1 blockade in stress-induced alcohol craving and relapse.[1], so development of verucerfont was terminated for this indication. Like other lead CRF-1 receptor antagonists, verucerfont was evaluated for therapeutic value in depressive disorder and anxiety disorders but failed to show significant efficacy in Phase 2 trials. Click here to link to ClinicalTrials.gov's full list of GSK561679 trials.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01187511 CRF1 Antagonist GSK561679 in Alcoholism Phase 2 Interventional National Institutes of Health Clinical Center (CC)