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Compound Detail

CHEMBL514201

TALMAPIMOD
🧪 Phase II
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🧪 Phase II
C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)c1cc2c(C(=O)C(=O)N(C)C)cn(C)c2cc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL514201
Name TALMAPIMOD
Phase Phase II
Structure Type MOL
InChI Key ZMELOYOKMZBMRB-DLBZAZTESA-N

Known Names

SCIO 469 Scio-469 Talmapimod
7
Targets
19
Activities
3
Assay Types
3
PK Parameters
20
Publications
3
Known Names
2
Indications
1
Mechanisms

Molecular Properties

513.0
MW (Da)
3.98
ALogP
5
HBA
0
HBD
65.9
PSA (Ų)
0.38
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -imod
USAN Year 2007

Extended Properties

Molecular Formula C27H30ClFN4O3
MW 513.01
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -1.30

Mechanism of Action

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

Indications

Arthritis, Rheumatoid Multiple Myeloma

Activity Summary

IC50 8 meas. best 8.05
Kd 6 meas. best 9.32
EC50 5 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 14
CHEMBL260
 Kd 9.32 8.71 0.5 2
Actin-related protein 2
CHEMBL6090
 Kd 8.4 8.4 4.0 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 8.05 7.712 9.0 5
Mitogen-activated protein kinase 11
CHEMBL3961
 Kd 7.82 7.82 15.0 1
MAP kinase-activated protein kinase 2
CHEMBL2208
 Kd 7.72 7.72 19.0 1
PBMC
CHEMBL613107
 EC50 7.7 7.7 20.0 4
Mitogen-activated protein kinase 11
CHEMBL3961
 IC50 7.01 7.01 98.0 1
Blood
CHEMBL613416
 EC50 6.52 6.52 300.0 1
Blood
CHEMBL613416
 IC50 6.52 6.52 300.0 2
Ribosyldihydronicotinamide dehydrogenase [quinone]
CHEMBL3959
 Kd 5.0 5.0 9918.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 15.0 % Rattus norvegicus
F 69.0 % Canis lupus familiaris
F 12.0 % Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 14 Kd = 0.48 nM 9.32 Binding affinity to p38alpha 19950901
Actin-related protein 2 Kd = 4.0 nM 8.4 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
Mitogen-activated protein kinase 14 Kd = 8.0 nM 8.1 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
Mitogen-activated protein kinase 14 IC50 = 9.0 nM 8.05 Inhibition of p38alpha 20071169
Mitogen-activated protein kinase 14 IC50 = 9.0 nM 8.05 Inhibition of human recombinant p38alpha by liquid scintillation counting 19950901
Mitogen-activated protein kinase 14 IC50 = 10.0 nM 8.0 Inhibition of human p38alpha assessed as reduction in [gamma32P]ATP incorporatio... 29620890
Mitogen-activated protein kinase 11 Kd = 15.0 nM 7.82 Binding affinity to p38beta 19950901
MAP kinase-activated protein kinase 2 Kd = 19.0 nM 7.72 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
PBMC EC50 = 20.0 nM 7.7 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL... 20071169
PBMC EC50 = 20.0 nM 7.7 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL... 20071169
PBMC EC50 = 20.0 nM 7.7 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL... 20071169
PBMC EC50 = 20.0 nM 7.7 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced TN... 20071169
Mitogen-activated protein kinase 14 IC50 = 36.0 nM 7.44 Inhibition of p38alpha active form expressed in Escherichia coli BL21(DE3) cells... 19928858
Mitogen-activated protein kinase 14 IC50 = 96.0 nM 7.02 Displacement of N,N'-(2,2'-(3,3'-disulfanediylbis(2,5-dioxopyrrolidine-3,1-diyl)... 19928858
Mitogen-activated protein kinase 11 IC50 = 98.0 nM 7.01 Inhibition of p38beta 20071169
Blood IC50 = 300.0 nM 6.52 Inhibition of LPS-induced TNFalpha production in human whole blood by ELISA 19950901
Blood IC50 = 300.0 nM 6.52 Inhibition of LPS-induced TNFalpha production in human whole blood 19195885
Blood EC50 = 300.0 nM 6.52 Antiinflammatory activity in 10 times diluted human whole blood assessed as inhi... 20071169
Ribosyldihydronicotinamide dehydrogenase [quinone] Kd = 9918.0 nM 5.0 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878

Literature References

PubMed DOI Target Context # Activities
20071169 10.1016/j.bmcl.2009.12.091 Liver microsomes 12
20071169 10.1016/j.bmcl.2009.12.091 ADMET 6
29191878 10.1126/science.aan4368 Unchecked 4
20071169 10.1016/j.bmcl.2009.12.091 PBMC 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19195885 10.1016/j.bmcl.2009.01.023 Unchecked 3
19928858 10.1021/jm901297e Mitogen-activated protein kinase 14 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL3301361 No relevant target 2
19950901 10.1021/jm9012906 Mitogen-activated protein kinase 14 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
20071169 10.1016/j.bmcl.2009.12.091 Rhesus monkey 1
29191878 10.1126/science.aan4368 Tyrosine-protein kinase ABL1 1
29191878 10.1126/science.aan4368 AP2-associated protein kinase 1 1
19195885 10.1016/j.bmcl.2009.01.023 Blood 1
20071169 10.1016/j.bmcl.2009.12.091 Canis familiaris 1
20071169 10.1016/j.bmcl.2009.12.091 Rattus norvegicus 1
20071169 10.1016/j.bmcl.2009.12.091 Blood 1
20071169 10.1016/j.bmcl.2009.12.091 Mitogen-activated protein kinase 14 1

Data from ChEMBL 36 via Core Engine