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Compound Detail

CHEMBL1090089

PAMAPIMOD
🧪 Phase II
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🧪 Phase II
Cn1c(=O)c(Oc2ccc(F)cc2F)cc2cnc(NC(CCO)CCO)nc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1090089
Name PAMAPIMOD
Phase Phase II
Structure Type MOL
InChI Key JYYLVUFNAHSSFE-UHFFFAOYSA-N

Known Names

Pamapimod R-1503 R1503 RO 4402257 Ro-4402257 RO4402257
13
Targets
29
Activities
3
Assay Types
20
PK Parameters
20
Publications
6
Known Names
1
Mechanisms

Molecular Properties

406.4
MW (Da)
1.94
ALogP
8
HBA
3
HBD
109.5
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -imod
USAN Year 2007

Extended Properties

Molecular Formula C19H20F2N4O4
MW 406.39
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.80

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
MAP kinase p38 alpha inhibitor INHIBITOR Mitogen-activated protein kinase 14 ✓ ✓

Activity Summary

Kd 18 meas. best 8.89
IC50 7 meas. best 7.85
EC50 4 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 14
CHEMBL260
 Kd 8.89 8.89 1.3 2
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 7.85 7.85 14.0 2
Mitogen-activated protein kinase 9
CHEMBL4179
 Kd 7.8 7.8 16.0 2
Mitogen-activated protein kinase 10
CHEMBL2637
 Kd 7.72 7.72 19.0 2
THP-1
CHEMBL614245
 IC50 7.6 7.6 25.0 2
Rattus norvegicus
CHEMBL376
 EC50 7.3 6.54 50.0 4
Blood
CHEMBL613416
 IC50 7.0 7.0 100.0 2
Mitogen-activated protein kinase 11
CHEMBL3961
 Kd 6.92 6.92 120.0 2
Ribosomal protein S6 kinase alpha-4
CHEMBL3125
 Kd 6.82 6.82 150.0 1
Unchecked
CHEMBL612545
 Kd 6.82 6.66 150.0 2
Serine/threonine-protein kinase NLK
CHEMBL5364
 Kd 6.77 6.77 170.0 2
Mitogen-activated protein kinase 8
CHEMBL2276
 Kd 6.72 6.72 190.0 2
Casein kinase I isoform epsilon
CHEMBL4937
 Kd 6.58 6.58 260.0 2
Ribosomal protein S6 kinase alpha-3
CHEMBL2345
 Kd 6.52 6.52 300.0 1
Mitogen-activated protein kinase 8
CHEMBL2276
 IC50 5.27 5.27 5420.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3130.0 ng.hr.mL-1 Rattus norvegicus
AUC 9410.0 ng.hr.mL-1 Macaca fascicularis
AUC 5220.0 ng.hr.mL-1 Canis lupus familiaris
CL 21.0 mL.min-1.kg-1 Rattus norvegicus
CL 10.83 mL.min-1.kg-1 Macaca fascicularis
CL 12.5 mL.min-1.kg-1 Canis lupus familiaris
CL 4.57 mL.min-1.g-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 3297.33 nM Rattus norvegicus
Cmax 4576.88 nM Macaca fascicularis
Cmax 3395.75 nM Canis lupus familiaris
F 80.1 % Rattus norvegicus
F 100.0 % Macaca fascicularis
F 78.2 % Canis lupus familiaris
T1/2 4.04 hr Rattus norvegicus
T1/2 13.8 hr Macaca fascicularis
T1/2 9.18 hr Canis lupus familiaris
Tmax 0.5 hr Rattus norvegicus
Tmax 1.5 hr Macaca fascicularis
Tmax 0.67 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 14 Kd = 1.3 nM 8.89 Binding affinity to p38alpha 19950901
Mitogen-activated protein kinase 14 Kd = 1.3 nM 8.89 Inhibition of p38alpha 21375264
Mitogen-activated protein kinase 14 IC50 = 14.0 nM 7.85 Inhibition of human recombinant p38alpha by liquid scintillation counting 19950901
Mitogen-activated protein kinase 14 IC50 = 14.0 nM 7.85 Inhibition of human recombinant p38alpha assessed as incorporation of 33P from g... 21375264
Mitogen-activated protein kinase 9 Kd = 16.0 nM 7.8 Binding affinity to JNK2 19950901
Mitogen-activated protein kinase 9 Kd = 16.0 nM 7.8 Inhibition of JNK2 21375264
Mitogen-activated protein kinase 10 Kd = 19.0 nM 7.72 Inhibition of JNK3 21375264
Mitogen-activated protein kinase 10 Kd = 19.0 nM 7.72 Binding affinity to JNK3 19950901
THP-1 IC50 = 25.0 nM 7.6 Inhibition of LPS-induced TNFalpha production in human THP1 cells by ELISA 19950901
THP-1 IC50 = 25.0 nM 7.6 Inhibition of LPS-induced TNFalpha production in human THP1 cells after 2 hrs by... 21375264
Rattus norvegicus EC50 = 50.0 nM 7.3 Inhibition of LPS-induced IL-6 production in po dosed rat serum administered 30 ... 21375264
Blood IC50 = 100.0 nM 7.0 Inhibition of LPS-induced IL1-beta production in human whole blood by ELISA 19950901
Blood IC50 = 100.0 nM 7.0 Inhibition of TNFalpha-induced IL1-beta production in human whole blood after 2 ... 21375264
Rattus norvegicus EC50 = 120.0 nM 6.92 Inhibition of LPS-induced TNFalpha production in po dosed rat serum administered... 21375264
Mitogen-activated protein kinase 11 Kd = 120.0 nM 6.92 Inhibition of P38beta 21375264
Mitogen-activated protein kinase 11 Kd = 120.0 nM 6.92 Binding affinity to p38beta 19950901
Unchecked Kd = 150.0 nM 6.82 Binding affinity to RSK4beta 19950901
Ribosomal protein S6 kinase alpha-4 Kd = 150.0 nM 6.82 Inhibition of RSK4 21375264
Serine/threonine-protein kinase NLK Kd = 170.0 nM 6.77 Binding affinity to NLK 19950901
Serine/threonine-protein kinase NLK Kd = 170.0 nM 6.77 Inhibition of NLK 21375264

Literature References

PubMed DOI Target Context # Activities
21375264 10.1021/jm101423y Rattus norvegicus 17
21375264 10.1021/jm101423y Cynomolgus monkey 7
21375264 10.1021/jm101423y Canis familiaris 7
19950901 10.1021/jm9012906 Mus musculus 4
21375264 10.1021/jm101423y Plasma 3
26704265 10.1016/j.bmcl.2015.11.099 Mitogen-activated protein kinase 8 3
21375264 10.1021/jm101423y Mitogen-activated protein kinase 14 3
21375264 10.1021/jm101423y Mitogen-activated protein kinase 10 2
19950901 10.1021/jm9012906 Mitogen-activated protein kinase 14 2
21375264 10.1021/jm101423y Mitogen-activated protein kinase 9 2
21375264 10.1021/jm101423y Mitogen-activated protein kinase 8 2
21375264 10.1021/jm101423y Cyclin-G-associated kinase 2
21375264 10.1021/jm101423y Casein kinase I isoform epsilon 2
21375264 10.1021/jm101423y Atypical kinase COQ8A, mitochondrial 2
21375264 10.1021/jm101423y Mitogen-activated protein kinase 11 2
19950901 10.1021/jm9012906 Rattus norvegicus 2
21375264 10.1021/jm101423y Serine/threonine-protein kinase NLK 2
19950901 10.1021/jm9012906 Unchecked 2
21375264 10.1021/jm101423y Ribosomal protein S6 kinase alpha-4 2
21375264 10.1021/jm101423y Serine/threonine-protein kinase 36 2

Data from ChEMBL 36 via Core Engine