rugocrixan   Click here for help

GtoPdb Ligand ID: 13739

Synonyms: AZD-8797 | AZD8797 | compound 18a [PMID: 23516963] | KAND-567 | KAND567
Compound class: Synthetic organic
Comment: The chemical structure for rugocrixan was derived from WHO proposed INN list 132 (Feb 2025), in which it is listed as CX3C chemokine receptor 1 (CX3CR1) antagonist and anti-inflammatory agent. A structural match in PubChem provides the synonyms AZD8797 [1-2] and KAND567 which appear to be names for the same compound. Rugocrixan is a non-competitive allosteric modulator of CX3CR1, blocking activation of the receptor by the chemotactic cytokine CX3CL1 (fractalkine) [2]. As CX3CL1 is invloved in regulating the function of certain immune and cancer cells, this inhibitor has potential therapeutic applications in inflammatory conditions and cancer [3]. There is also evidence of a link between CX3CR1/CX3CL1 signalling and coronary artery disease [4].

COVID-19: Kancera initiated a clinical trial to evaluate the efficacy of rugocrixan (KAND567) to reduce SARS-CoV-2-associated lung inflammation, but the study was terminated due to slow recruitment of subjects.
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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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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 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 145.96
Molecular weight 403.57
XLogP 1.97
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 CC(C)C[C@H](CO)NC1=C2C(=NC(=N1)S[C@@H](C)C3=CC=CC=C3)N=C(N)S2
Isomeric SMILES C[C@@H](C1=CC=CC=C1)SC2=NC3=C(C(=N2)N[C@H](CC(C)C)CO)SC(=N3)N
InChI InChI=1S/C19H25N5OS2/c1-11(2)9-14(10-25)21-16-15-17(22-18(20)27-15)24-19(23-16)26-12(3)13-7-5-4-6-8-13/h4-8,11-12,14,25H,9-10H2,1-3H3,(H3,20,21,22,23,24)/t12-,14+/m0/s1
InChI Key ZMQSLMZOWVGBSM-GXTWGEPZSA-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/)
Bioactivity Comments
Rugocrixan inhibits the capture of CX3CR1-expressing leucocytes by CX3CL1-expressing endothelial cells in vitro (IC50 5.8 nM), and prevents CX3CL1-induced signalling in a [35S]GTPγS accumulation assay (IC50 340 nM) [2]. 3H-rugocrixan binds to CX3CR1 with a Kd of 12 nM in a radioligand-binding assay.
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CX3CR1 Hs Allosteric modulator Antagonist 8.1 pKi - 2
⤷ pKi 8.1 (Ki 7.3x10-9 M) [2]
Description: Measuring displacement of [3H]AZD8797/rugocrixan by unlabelled ligand