REPARIXIN

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Synonyms
Status
Molecule Category UNKNOWN
UNII U604E1NB3K
EPA CompTox DTXSID6046509

Structure

InChI Key KQDRVXQXKZXMHP-LLVKDONJSA-N
Smiles CC(C)Cc1ccc([C@@H](C)C(=O)NS(C)(=O)=O)cc1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H21NO3S
Molecular Weight 283.39
AlogP 2.06
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 63.24
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Interleukin-8 receptor A modulator MODULATOR PubMed 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(%)
Enzyme Oxidoreductase
- - - - 8
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- 1-100 - - 65-68
Assay Description Organism Bioactivity Reference
Inhibition of CXCL8-induced chemotaxis in human polymorphonuclear cells Homo sapiens 5.3 nM
Inhibition of lipopolysaccharide-induced PGE-2 production at 10e-5 M Mus musculus 8.0 %
Inhibition of CXCL8-induced chemotaxis of human polymorphonuclear cells at 10e-8 M Homo sapiens 65.0 %
Inhibition of CXCL8-induced cell migration in L1.2 cells expressing wild type CXCR1 at 0.1 uM by chemotaxis assay Mus musculus 80.0 %
Inhibition of CXCL8-induced cell migration in L1.2 cells expressing CXCR1 by chemotaxis assay Mus musculus 5.6 nM
Inhibition of CXCL8-induced cell migration in L1.2 cells expressing Ile43Val CXCR1 mutant by chemotaxis assay Mus musculus 80.0 nM
Noncompetitive inhibition of human CXCR1 assessed as inhibition of CXCL8-induced neutrophile chemotaxis at 10 nM Homo sapiens 65.0 %
Inhibition of CXCR2 in human polymorphonucleate cells assessed as inhibition of CXCL1-induced chemotaxis at 10'-8 M incubated for 15 mins prior to CXCL1-induction measured after 45 mins Homo sapiens 22.0 %
Inhibition of CXCR1/2 in human polymorphonucleate cells assessed as inhibition of CXCL8-induced chemotaxis at 10'-8 M incubated for 15 mins prior to CXCL8-induction measured after 45 mins Homo sapiens 68.0 %
Antagonist activity at CXCR2 assessed as inhibition of CXCL8-induced neutrophil chemotaxis None 1.0 nM
Binding affinity to CXCR2 None 100.0 nM
Binding affinity to CXCR1 None 1.0 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 14.79 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 28.59 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.1 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.052 %
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 0.19 % 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 -0.01 % 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 -0.15 % 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 0.19 % 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 -0.15 % 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 -0.01 %

Cross References

Resources Reference
ChEMBL CHEMBL191413
DrugBank DB12614
FDA SRS U604E1NB3K
Guide to Pharmacology 8498
PubChem 9838712
SureChEMBL SCHEMBL1884299
ZINC ZINC000000008717
CONTENTS