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.
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
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 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
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 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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-2-[[2-amino-5-[(1S)-1-phenylethyl]sulfanyl-[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-methylpentan-1-ol
International Nonproprietary Names Click here for help
INN number INN
13371 rugocrixan
Synonyms Click here for help
AZD-8797 | AZD8797 | compound 18a [PMID: 23516963] | KAND-567 | KAND567
Database Links Click here for help
BindingDB Ligand 50432452
CAS Registry No. 911715-90-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL2349310
GtoPdb PubChem SID 507750372
PubChem CID 11965767
Search Google for chemical match using the InChIKey ZMQSLMZOWVGBSM-GXTWGEPZSA-N
Search Google for chemicals with the same backbone ZMQSLMZOWVGBSM
Search PubMed clinical trials rugocrixan
Search PubMed titles rugocrixan
Search PubMed titles/abstracts rugocrixan
UniChem Compound Search for chemical match using the InChIKey ZMQSLMZOWVGBSM-GXTWGEPZSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZMQSLMZOWVGBSM-GXTWGEPZSA-N