LOSMAPIMOD

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Synonyms
Status
Molecule Category Free-form
UNII F2DQF16BXE

Structure

InChI Key KKYABQBFGDZVNQ-UHFFFAOYSA-N
Smiles Cc1c(F)cc(C(=O)NC2CC2)cc1-c1ccc(C(=O)NCC(C)(C)C)cn1
InChI
InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H26FN3O2
Molecular Weight 383.47
AlogP 3.86
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 71.09
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
MAP kinase p38 alpha inhibitor INHIBITOR PubMed PubMed
Protein: MAP kinase p38 beta
Description: Mitogen-activated protein kinase 11
Organism : Homo sapiens
Q15759 ENSG00000185386
Protein: MAP kinase p38 alpha
Description: Mitogen-activated protein kinase 14
Organism : Homo sapiens
Q16539 ENSG00000112062
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 31623 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase p38 subfamily
- 25-100 - 8-63 -
Assay Description Organism Bioactivity Reference
Inhibition of LPS-induced TNFalpha production in human whole blood by ELISA Homo sapiens 25.12 nM
Binding affinity to p38alpha None 7.943 nM
Binding affinity to p38beta None 25.12 nM
Inhibition of GST-tagged p38alpha by fluorescence polarization method None 7.943 nM
Inhibition of GST-tagged p38beta by fluorescence polarization method None 25.12 nM
Inhibition of p38alpha-dependent TNFalpha production in human PBMC preincubated for 1 hr before LPS challenge by ELISA Homo sapiens 100.0 nM
Inhibition of p38alpha-dependent TNFalpha production in human whole blood preincubated for 1 hr before LPS challenge by ELISA Homo sapiens 25.12 nM
Competitive inhibition of p38alpha catalytic activity using ATP None 63.1 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 29.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 9.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 27.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 11.0 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 1.32 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.24 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.924 %
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 -0.11 % 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 -0.18 % 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 -0.11 % 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 -0.18 %

Cross References

Resources Reference
ChEBI 131167
ChEMBL CHEMBL1088752
DrugBank DB12270
FDA SRS F2DQF16BXE
Guide to Pharmacology 7835
PubChem 11552706
SureChEMBL SCHEMBL1070401
ZINC ZINC000035793138
CONTENTS