NAVARIXIN

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Synonyms
Status
Molecule Category Mixture
UNII 7V3BY6G538

Structure

InChI Key RXIUEIPPLAFSDF-CYBMUJFWSA-N
Smiles CC[C@@H](Nc1c(Nc2cccc(C(=O)N(C)C)c2O)c(=O)c1=O)c1ccc(C)o1
InChI
InChI=1S/C21H23N3O5/c1-5-13(15-10-9-11(2)29-15)22-16-17(20(27)19(16)26)23-14-8-6-7-12(18(14)25)21(28)24(3)4/h6-10,13,22-23,25H,5H2,1-4H3/t13-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H23N3O5
Molecular Weight 397.43
AlogP 2.9
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 7.0
Polar Surface Area 111.88
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Interleukin-8 receptor A antagonist ANTAGONIST PubMed PubMed ClinicalTrials PubMed
Protein: Interleukin-8 receptor A
Description: C-X-C chemokine receptor type 1
Organism : Homo sapiens
P25024 ENSG00000163464
Protein: Interleukin-8 receptor B
Description: C-X-C chemokine receptor type 2
Organism : Homo sapiens
P25025 ENSG00000180871
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- 0-680 - 4-5 -
Assay Description Organism Bioactivity Reference
Displacement of [125I]hCXCL8 from human CXCR2 receptor expressed in BaF3 cells Homo sapiens 2.6 nM
Displacement of [125I]hCXCL8 from human CXCR1 receptor expressed in BaF3 cells Homo sapiens 36.0 nM
Inhibition of CXCL8-induced human neutrophil chemotaxis Homo sapiens 16.0 nM
Inhibition of CXCL1-induced human neutrophil chemotaxis Homo sapiens 1.0 nM
Inhibition of CXCR3 receptor at 2 to 20 uM Homo sapiens 15.0 %
Inhibition of CCR5 receptor at 2 to 20 uM Homo sapiens 15.0 %
Displacement of [125I]IL8 from human CXCR2 expressed in CHO cells by SPA Homo sapiens 5.0 nM
Displacement of [125I]IL8 from human CXCR1 expressed in CHO cells by SPA Homo sapiens 18.0 nM
Binding affinity to CXCR2 None 4.0 nM
Binding affinity to CXCR1 None 20.0 nM
Displacement of human [125I]IL-8 from human CXCR2 Homo sapiens 5.0 nM
Binding affinity to CXCR2 None 0.049 nM
Binding affinity to CXCR1 None 3.9 nM
Antagonist activity at CXCR2 in human whole blood by CD11b assay Homo sapiens 450.0 nM
Antagonist activity at CXCR2 in C57 mouse whole blood assessed as inhibition of GROalpha-stimulated CD11b upregulation preincubated for 1 hr followed by GROalpha stimulation measured after 10 mins by FITC-staining based FACS analysis Mus musculus 8.1 nM
Antagonist activity at CXCR2 in human whole blood assessed as inhibition of GROalpha-stimulated CD11b upregulation preincubated for 15 mins followed by GROalpha stimulation measured after 15 mins by FITC-staining based FACS analysis Homo sapiens 680.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 6.94 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.55 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.42 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.22 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.22 %
Antagonist activity at CXCR1 (unknown origin) stably expressed in HEK293 cells assessed as reduction in IL-8-induced intracellular calcium change incubated for 15 mins followed by IL-8-stimulation and measured after 15 mins by cAMP-d2/Eu-Anti-cAM based fluorescence assay Homo sapiens 198.3 nM
Antagonist activity in CXCR2 (unknown origin) expressed in human HEK293 cells co-expressing Galpha16 assessed as reduction in calcium immobilization pretreated with Fluo-4AM for 45 mins followed by compound addition and measured after 10 mins by Fluo-4AM dye based fluorescence assay Homo sapiens 10.0 nM
Antagonist activity in CXCR1 (unknown origin) expressed in human HEK293 cells co-expressing Galpha16 assessed as reduction in calcium immobilization pretreated with Fluo-4AM for 45 mins followed by compound addition and measured after 10 mins by Fluo-4AM dye based fluorescence assay Homo sapiens 160.0 nM
Antagonist activity at CXCR1 (unknown origin) expressed in HEK293 cells assessed as suppression of IL-8-induced inhibition of forskolin-induced cAMP formation preincubated for 15 mins followed by forskolin and IL-8 stimulation and measured after 15 mins by cAMP-d2 and Eu-Anti-cAMP based fluorescence assay Homo sapiens 198.3 nM

Cross References

Resources Reference
ChEMBL CHEMBL2103864
FDA SRS 7V3BY6G538
Guide to Pharmacology 8497
PubChem 71587828
SureChEMBL SCHEMBL2024684
ChEMBL CHEMBL216981
FDA SRS 7V3BY6G538
Guide to Pharmacology 8497
PubChem 71587828
SureChEMBL SCHEMBL184744
ZINC ZINC000100033051
CONTENTS