AZD5069   Click here for help

GtoPdb Ligand ID: 8948

Synonyms: AZD-5069
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AZD5069 is a novel, selective antagonist of the chemokine receptor, CXCR2. The structure shown here was drawn from that in [6], which specifies stereochemistry. This structure is identical to Example 47 in patent US7838675 [1]. PubChem records the structure with no specified stereochemistry (CID 59558839).
Small-molecule antagonists of CXCR2 are being developed for their potential to treat inflammatory conditions.
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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
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 8
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 158.56
Molecular weight 476.1
XLogP 1.73
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 OCC(C(Oc1nc(SCc2cccc(c2F)F)nc(c1)NS(=O)(=O)N1CCC1)C)O
Isomeric SMILES OC[C@@H]([C@H](Oc1nc(SCc2cccc(c2F)F)nc(c1)NS(=O)(=O)N1CCC1)C)O
InChI InChI=1S/C18H22F2N4O5S2/c1-11(14(26)9-25)29-16-8-15(23-31(27,28)24-6-3-7-24)21-18(22-16)30-10-12-4-2-5-13(19)17(12)20/h2,4-5,8,11,14,25-26H,3,6-7,9-10H2,1H3,(H,21,22,23)/t11-,14+/m1/s1
InChI Key QZECRCLSIGFCIO-RISCZKNCSA-N
Bioactivity Comments
In a selectivity screening set if 153 human receptors and enzymes, significant levels of activity was only observed at CCR2 (pEC50 5.2) and CCR5 (pEC50 4.9) using ≥10μM AZD5069, in addition to the primary target [6].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CXCR2 Primary target of this compound Hs Antagonist Antagonist 9.1 pIC50 - 6
⤷ pIC50 9.1 (IC50 7.9x10-10 M) [6]
Description: Measuring displacement of CXCL8 binding to recombinant CXCR2 in HEK cell membrane preparations.
CXCR1 Hs Antagonist Antagonist 6.9 pIC50 - 6
⤷ pIC50 6.9 (IC50 1.25x10-7 M) [6]
Description: Measuring displacement of CXCL8 binding to recombinant CXCR1 in HEK cell membrane preparations.