CCX354   Click here for help

GtoPdb Ligand ID: 10164

Synonyms: CCX 354 | CCX-354 | CCX-354-C
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: CCX354 is an orally active CCR1 antagonist that was originally developed by Chemocentryx for anti-inflammatory/immunomodulatory potential. The chemical structure is claimed as Example 16 in patent WO2008147815A1 [1]. The structure in the patent resolves to PubChem CID 25016615, which is a tautomeric representation of the claimed structure.
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 1
Rotatable bonds 5
Topological polar surface area 91.11
Molecular weight 451.15
XLogP 2.67
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 COc1cc(ccc1Cl)N1CCN(CC1)C(=O)Cn1[nH]c(=C2N=CC=N2)c2c1nccc2
Isomeric SMILES COc1cc(ccc1Cl)N1CCN(CC1)C(=O)Cn1[nH]c(=C2N=CC=N2)c2c1nccc2
InChI InChI=1S/C22H22ClN7O2/c1-32-18-13-15(4-5-17(18)23)28-9-11-29(12-10-28)19(31)14-30-22-16(3-2-6-26-22)20(27-30)21-24-7-8-25-21/h2-8,13,27H,9-12,14H2,1H3
InChI Key WSVDLXWYJRCDBZ-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
CCX354 (as code CCX-354-C) completed Phase 2 clinical evaluation in rheumatoid arthritis patients in which it appeared to be safe and well tolerated, and showed some evidence of clinical efficacy [2], but development was not progressed further (see NCT01242917).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
CCX354 downregulates migration of monocytes and macrophages to synovial tissue, by antagonising the effects of CCR1 chemokines such as CCL3 (MIP-1α) and CCL5 (RANTES).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01242917 A Study to Evaluate the Safety and Efficacy of CCX354-C in Subjects With Rheumatoid Arthritis Partially Responsive to Methotrexate Therapy Phase 2 Interventional ChemoCentryx