NEFLAMAPIMOD

/static/temp/default.svg Search structure
Synonyms
745
Status
Molecule Category Free-form
UNII TYL52QM320
EPA CompTox DTXSID90175115

Structure

InChI Key VEPKQEUBKLEPRA-UHFFFAOYSA-N
Smiles O=c1ncn2nc(Sc3ccc(F)cc3F)ccc2c1-c1c(Cl)cccc1Cl
InChI
InChI=1S/C19H9Cl2F2N3OS/c20-11-2-1-3-12(21)17(11)18-14-5-7-16(25-26(14)9-24-19(18)27)28-15-6-4-10(22)8-13(15)23/h1-9H

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H9Cl2F2N3OS
Molecular Weight 436.27
AlogP 5.49
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 47.26
Molecular species None
Aromatic Rings 4.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
MAP kinase p38 alpha inhibitor INHIBITOR PubMed
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 Kinase Protein Kinase AGC protein kinase group AGC protein kinase DMPK family AGC protein kinase ROCK subfamily
- - - - 8
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC alpha subfamily
- - - - 5
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC delta subfamily
- - - - 0
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC iota subfamily
- - - - 0
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKN family
- - - - 13
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase RSK family AGC protein kinase MSK subfamily
- - - - 0
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase RSK family AGC protein kinase RSK subfamily
- - - - 0
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase SGK family
- - - - 5
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family CAMK protein kinase CHK1 subfamily
- - - - 0
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase MAPKAPK family CAMK protein kinase MAPKAPK subfamily
- - - - 12
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase RSKb family CAMK protein kinase MSKb subfamily
- - - - 0
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase RSKb family CAMK protein kinase RSKb subfamily
- - - - 0
Enzyme Kinase Protein Kinase CK1 protein kinase group CK1 protein kinase CK1 family
- - - - 1
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase CDC2 subfamily
- - - - 0
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase CDK family CMGC protein kinase CDK5 subfamily
- - - - 0
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase ERK subfamily
- - - - 0
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase JNK subfamily
- - - - 10
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase p38 subfamily
- 9-25119 3-3 1 84
Enzyme Kinase Protein Kinase Other protein kinase group
- - - - 0
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase MST subfamily
- - - - 0
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase PAKA subfamily
- - - - 0
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE7 family
- - - - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- - 710-7200 - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Axl family
- - - - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase DDR family
- - 1100-1100 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- - - - 7
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Eph family
- - 1600-6200 - 16
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase FGFR family
- - - - 20
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Fer family
- - - - 7
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase InsR family
- - - - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- - 870-8400 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- - 1200-1300 - 0
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tie family
- - - - 0
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase RAF family
- - - - 0
Assay Description Organism Bioactivity Reference
Ex vivo inhibition of Mitogen activated protein kinase activated protein 1 hr after 3 mg/kg dose Mus musculus 29.0 %
In vitro inhibitory activity determined against human mitogen-activated protein kinase p38 alpha None 29.0 nM
Tested in vitro for filter plate binding versus gamma-[33P]ATP in active recombinant murine FLAG-P38 alpha fusion protein (GST-Activating transcription factor-2). None 22.0 nM
Inhibition of LPS-induced p38-related Tumor necrosis factor alpha release in human whole blood Homo sapiens 700.0 nM
Inhibition of LPS-induced p38-related Tumor necrosis factor alpha release by THP-1 cells Homo sapiens 150.0 nM
Average Binding Constant for ABL2; NA=Not Active at 10 uM Homo sapiens 220.0 nM
Average Binding Constant for p38-alpha; NA=Not Active at 10 uM Homo sapiens 3.2 nM
Average Binding Constant for p38-beta; NA=Not Active at 10 uM Homo sapiens 160.0 nM
Average Binding Constant for PDGFRB; NA=Not Active at 10 uM Homo sapiens 870.0 nM
Average Binding Constant for ABL1; NA=Not Active at 10 uM Homo sapiens 870.0 nM
Average Binding Constant for ABL1(Y253F); NA=Not Active at 10 uM Homo sapiens 710.0 nM
Average Binding Constant for SRC; NA=Not Active at 10 uM Homo sapiens 980.0 nM
Inhibition of LPS-stimulated TNFalpha production in THP1 cells Homo sapiens 56.0 nM
Inhibition of p38 Homo sapiens 10.0 nM
Inhibition of p38 Homo sapiens 0.8 nM
Inhibition of LPS-induced TNFalpha production in human THP1 cells Homo sapiens 39.0 nM
Inhibition of human p38-alpha kinase Homo sapiens 29.0 nM
Binding constant for full-length p38-alpha Homo sapiens 2.8 nM
Binding constant for full-length p38-beta Homo sapiens 74.0 nM
Binding constant for ABL1 kinase domain Homo sapiens 730.0 nM
Inhibition of p38alpha None 70.0 nM
Inhibition of LPS-induced TNFalpha production in human whole blood by ELISA Homo sapiens 177.0 nM
Inhibition of human recombinant p38alpha by liquid scintillation counting Homo sapiens 10.0 nM
Binding constant for p38-alpha kinase domain None 2.8 nM
Binding constant for p38-beta kinase domain None 74.0 nM
DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substrate: Myelin Basic Protein) Escherichia coli 643.0 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: MAPK14 None 5.012 nM
PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member name: ROS1 None 398.11 nM
Inhibition of p38alpha kinase using KRELVEPLTPSGEAPNQALLR as substrate for 20 mins by lactate dehydrogenase-coupled spectrophotometric assay None 9.0 nM
Inhibition of p38alpha in human PBMC assessed as inhibition of LPS-induced IL1beta production after 16 to 18 hrs by ELISA Homo sapiens 45.0 nM
Inhibition of p38alpha in human PBMC assessed as inhibition of LPS-induced TNFalpha production after 16 to 18 hrs by ELISA Homo sapiens 51.0 nM
Inhibition of p38alpha in human whole blood assessed as inhibition of LPS-induced IL1beta production after 16 to 18 hrs by ELISA Homo sapiens 150.0 nM
Inhibition of p38alpha in human whole blood assessed as inhibition of LPS-induced TNFalpha production after 16 to 18 hrs by ELISA Homo sapiens 180.0 nM
Inhibition of p38beta using KRELVEPLTPSGEAPNQALLR as substrate for 10 mins by lactate dehydrogenase-coupled spectrophotometric assay None 220.0 nM
Inhibition of Abl at 2 uM None 0.0 %
Inhibition of Ampk at 2 uM None 0.0 %
Inhibition of Axl at 2 uM None 0.0 %
Inhibition of Blk at 2 uM None 0.0 %
Inhibition of CDK1 at 2 uM None 0.0 %
Inhibition of CDK5 at 2 uM None 0.0 %
Inhibition of CHK1 at 2 uM None 0.0 %
Inhibition of CK1 at 2 uM None 1.0 %
Inhibition of EGFR at 2 uM None 7.0 %
Inhibition of ERK1 at 2 uM None 0.0 %
Inhibition of EphB4 at 2 uM None 16.0 %
Inhibition of FES at 2 uM None 7.0 %
Inhibition of FGFR3 at 2 uM None 20.0 %
Inhibition of Fyn at 2 uM None 6.0 %
Inhibition of IKKa at 2 uM None 0.0 %
Inhibition of IKKb at 2 uM None 0.0 %
Inhibition of IRTK at 2 uM None 0.0 %
Inhibition of JNK1 at 2 uM None 10.0 %
Inhibition of LCK at 2 uM None 20.0 %
Inhibition of Lyn at 2 uM None 0.0 %
Inhibition of Mek1 at 2 uM None 5.0 %
Inhibition of MKK6 at 2 uM None 95.0 %
Inhibition of MKK7 at 2 uM None 0.0 %
Inhibition of MSK1 at 2 uM None 0.0 %
Inhibition of Mst2 at 2 uM None 0.0 %
Inhibition of MEK2 at 2 uM None 14.0 %
Inhibition of p38beta at 2 uM None 84.0 %
Inhibition of PAK2 at 2 uM None 0.0 %
Inhibition of PDGFR at 2 uM None 7.0 %
Inhibition of PKCb2 at 2 uM None 5.0 %
Inhibition of PKCiota at 2 uM None 0.0 %
Inhibition of PKCtheta at 2 uM None 0.0 %
Inhibition of PRAK at 2 uM None 12.0 %
Inhibition of PRK2 at 2 uM None 13.0 %
Inhibition of RAFc at 2 uM None 0.0 %
Inhibition of ROCK2 at 2 uM None 8.0 %
Inhibition of Rsk3 at 2 uM None 0.0 %
Inhibition of SGK at 2 uM None 5.0 %
Inhibition of Tie2 at 2 uM None 0.0 %
Antiarthritic activity in complete Freund's adjuvant-immunized DBA/1J mouse assessed as inhibition of type 2 collagen-induced paw inflammation at 2.5 mg/kg, po bid measured on day 20 Mus musculus 27.0 %
Antiarthritic activity in complete Freund's adjuvant-immunized DBA/1J mouse assessed as inhibition of type 2 collagen-induced paw inflammation at 5 mg/kg, po bid measured on day 20 Mus musculus 31.0 %
Antiarthritic activity in complete Freund's adjuvant-immunized DBA/1J mouse assessed as inhibition of type 2 collagen-induced paw inflammation at 10 mg/kg, po bid measured on day 20 Mus musculus 44.0 %
Antiarthritic activity in complete Freund's adjuvant-immunized DBA/1J mouse assessed as inhibition of type 2 collagen-induced bone and cartilage erosion at 2.5 mg/kg, po bid measured on day 20 Mus musculus 35.0 %
Antiarthritic activity in complete Freund's adjuvant-immunized DBA/1J mouse assessed as inhibition of type 2 collagen-induced bone and cartilage erosion at 5 mg/kg, po bid measured on day 20 Mus musculus 32.0 %
Antiarthritic activity in complete Freund's adjuvant-immunized DBA/1J mouse assessed as inhibition of type 2 collagen-induced bone and cartilage erosion at 10 mg/kg, po bid measured on day 20 Mus musculus 39.0 %
Binding affinity to p38alpha (unknown origin) Homo sapiens 2.8 nM
Inhibition of MAPK p38 (unknown origin) Homo sapiens 70.0 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 -9.62 %
Inhibition of P38 mitogen activated protein kinase (unknown origin) Homo sapiens 0.8 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 23.31 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.97 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -0.2704 %
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 -0.29 % 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 -0.15 % 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 0.03 % 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 -0.29 % 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 %
Antagonist activity at p38 MAPK alpha (unknown origin) Homo sapiens 10.0 nM

Cross References

Resources Reference
ChEBI 90528
ChEMBL CHEMBL119385
DrugBank DB07138
FDA SRS TYL52QM320
Guide to Pharmacology 5719
PDB 52P
PubChem 3038525
SureChEMBL SCHEMBL156367
ZINC ZINC000013493055
CONTENTS