ilacirnon   Click here for help

GtoPdb Ligand ID: 11185

Synonyms: CCX-140B | CCX140 | CCX140-B | CCX140B | Example 5 [WO2009009740A1]
Compound class: Synthetic organic
Comment: Ilacirnon (CCX140B) is a clinical stage, orally administered antagonist of the chemokine receptor CCR2 [3]. It was developed by Chemocentryx. The chemical structure of CCX140B matches that submitted to the WHO for the INN ilacirnon, and is one of those claimed in Chemocentryx's patent WO2009009740A1 [2]
Click here for help

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.

✖

View interactive charts of activity data across species

ilacirnon is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 126.08
Molecular weight 495.04
XLogP 3.98
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
Click here for help

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/)

✖
Canonical SMILES Cc1cnc(c(c1)NS(=O)(=O)c1ccc(c(c1)C(F)(F)F)Cl)C(=O)c1ncnc2c1cc[nH]2
Isomeric SMILES Cc1cnc(c(c1)NS(=O)(=O)c1ccc(c(c1)C(F)(F)F)Cl)C(=O)c1ncnc2c1cc[nH]2
InChI InChI=1S/C20H13ClF3N5O3S/c1-10-6-15(29-33(31,32)11-2-3-14(21)13(7-11)20(22,23)24)17(26-8-10)18(30)16-12-4-5-25-19(12)28-9-27-16/h2-9,29H,1H3,(H,25,27,28)
InChI Key LUUMLYXKTPBTQR-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
CCX140 was advanced to clinical evaluation, reaching Phase 2 for diabetic nephropathy and the rare kidney disorder focal segmental slomerulosclerosis (FSGS).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01440257 A Study to Evaluate the Effect of CCX140-B on Urinary Albumin Excretion in Subjects With Type 2 Diabetes and Albuminuria Phase 2 Interventional ChemoCentryx
NCT03703908 A Study of CCX140-B in Subjects With Primary FSGS and Nephrotic Syndrome Phase 2 Interventional ChemoCentryx
NCT01447147 A Study to Evaluate the Safety and Efficacy of CCX140-B in Subjects With Diabetic Nephropathy Phase 2 Interventional ChemoCentryx 1
NCT03536754 A Study of CCX140-B in Subjects With FSGS Phase 2 Interventional ChemoCentryx This trial is known as the LUMINA-1 study. In mid-2020, Chemocentryx announced (on their company website) that this study had found no evidence of meaningful clinical efficacy in FSGS patients compared to placebo after 12 weeks of CCX140 treatment, and that the compound would not continue in FSGS.