reparixin   Click here for help

GtoPdb Ligand ID: 8498

Synonyms: DF 1681Y | repertaxin
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Reparixin is an orally bioavailable compound that has been explored for potential to disrupt IL-8/CXCR1/2 signalling in cancer and transplant indications. It negatively modulates CXCR1 and CXCR2 dependent functions [1], but without inhibiting chemokine binding to either receptor. Direct binding to CXCR1 has only been indicated by molecular modelling, so the mechanism of action of this molecule remains to be fully resolved.
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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

reparixin 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 71.62
Molecular weight 283.12
XLogP 3.02
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(Cc1ccc(cc1)C(C(=O)NS(=O)(=O)C)C)C
Isomeric SMILES CC(Cc1ccc(cc1)[C@H](C(=O)NS(=O)(=O)C)C)C
InChI InChI=1S/C14H21NO3S/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(16)15-19(4,17)18/h5-8,10-11H,9H2,1-4H3,(H,15,16)/t11-/m1/s1
InChI Key KQDRVXQXKZXMHP-LLVKDONJSA-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
Reparixin has completed Phase 3 clinical trial as a single agent anti-rejection therapy for patients receiving pancreatic islet transplant . Published results showed that it did not improve insulin secretion in islet cell recipients [3]. Phase 2 trial NCT01861054 in HER2 negative breast cancer has reported that as a single agent reparixin reduced cancer stem cell numbers, with no serious adverse effects [2]. A Phase 2 study investigating reparixin's potential to prevent early allograft dysfunction in orthotopic liver transplantation (NCT03031470) has been completed, but no results have been published as far as we can ascertain.

COVID-19: Reparixin's anti-inflammatory activity is being explored for potential to reduce the risk of disease progression in COVID-19 patients.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05254990 Reparixin as add-on Therapy to Standard of Care to Limit Disease Progression in Adult Patients With COVID-19. Phase 3 Interventional Dompé Farmaceutici S.p.A