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Compound Detail

CHEMBL5089410

PILAVAPADIN
🧪 Phase II
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🧪 Phase II
CC(C)C[C@](C)(N)COc1ccc(-c2ccnc(C(F)F)c2)nc1C(F)F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5089410
Name PILAVAPADIN
Phase Phase II
Structure Type MOL
InChI Key RKAHOQATMSONTM-IBGZPJMESA-N

Known Names

AAK1-IN-1 BMS-986176 LX-9211 Lx9211 Pilavapadin Pilavapadina Pilavapadine
10
Targets
20
Activities
2
Assay Types
30
PK Parameters
20
Publications
7
Known Names
1
Indications

Molecular Properties

385.4
MW (Da)
5.16
ALogP
4
HBA
1
HBD
61.0
PSA (Ų)
0.64
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -padin

Extended Properties

Molecular Formula C19H23F4N3O
MW 385.41
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.63

Indications

Neuralgia, Postherpetic

Activity Summary

IC50 19 meas. best 8.92
Ki 1 meas. best 9.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.51 9.51 0.3 1
AP2-associated protein kinase 1
CHEMBL3830
 IC50 8.92 8.6982 1.2 11
MAP kinase-interacting serine/threonine-protein kinase 1
CHEMBL4718
 IC50 6.8 6.8 160.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.41 6.41 390.0 1
Citron Rho-interacting kinase
CHEMBL5579
 IC50 6.39 6.39 410.0 1
Serine/threonine-protein kinase LATS2
CHEMBL5907
 IC50 6.18 6.18 660.0 1
Cyclin-G-associated kinase
CHEMBL4355
 IC50 6.1 6.1 800.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.85 5.85 1400.0 1
BMP-2-inducible protein kinase
CHEMBL4522
 IC50 5.72 5.72 1900.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 5.27 5.27 5400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6710.0 ng.hr.mL-1 Mus musculus
AUC 5780.0 ng.hr.mL-1 Mus musculus
AUC 1180.0 ng.hr.mL-1 Rattus norvegicus
AUC 880.0 ng.hr.mL-1 Rattus norvegicus
AUC 1210.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1630.0 ng.hr.mL-1 Canis lupus familiaris
AUC 980.0 ng.hr.mL-1 Macaca mulatta
AUC 270.0 ng.hr.mL-1 Macaca mulatta
CL 5.0 mL.min-1.kg-1 Mus musculus
CL 28.5 mL.min-1.kg-1 Rattus norvegicus
CL 28.5 mL.min-1.kg-1 Canis lupus familiaris
CL 41.2 mL.min-1.kg-1 Macaca mulatta
Cmax 5.0 nM Rattus norvegicus
Cmax 19.0 nM Rattus norvegicus
Cmax 63.0 nM Rattus norvegicus
Cmax 6.0 nM Rattus norvegicus
Cmax 25.0 nM Rattus norvegicus
Cmax 92.0 nM Rattus norvegicus
Cmax 366.0 nM Rattus norvegicus
Cmax 200.0 nM Rattus norvegicus
Cmax 780.0 nM Rattus norvegicus
Cmax 1650.0 nM Rattus norvegicus
Cmax 674.61 nM Mus musculus
Cmax 155.68 nM Rattus norvegicus
Cmax 518.93 nM Canis lupus familiaris
Cmax 51.89 nM Macaca mulatta
F 100.0 % Mus musculus
F 50.0 % Rattus norvegicus
F 87.0 % Canis lupus familiaris
F 11.0 % Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.31 nM 9.51 Displacement of 3H-LP-927443 from AAK1 in mouse brain membrane homogenate assess... 35257579
AP2-associated protein kinase 1 IC50 = 1.2 nM 8.92 Inhibition of AAK1 (unknown origin) 38377825
AP2-associated protein kinase 1 IC50 = 2.0 nM 8.7 Inhibition of GST-Xa tagged human AAK1 (30 to 330 residues) expresssed in bacter... 35257579
AP2-associated protein kinase 1 IC50 = 2.0 nM 8.7 Inhibition of full length human AAK1 expressed in HEK293F cells assessed as supp... 35261239
AP2-associated protein kinase 1 IC50 = 2.0 nM 8.7 Inhibition of bacterially expressed GST-Xa-tagged human AAK1 using 5-FAM-labelle... 35261239
AP2-associated protein kinase 1 IC50 = 2.0 nM 8.7 Inhibition of AKK1 in HEK293F cells assessed as reduction in phospho mu2 formati... 35257579
AP2-associated protein kinase 1 IC50 = 2.2 nM 8.66 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 2.2 nM 8.66 Kinase Assay: The assays were performed in U-bottom 384-well plates. The final a... -
AP2-associated protein kinase 1 IC50 = 2.2 nM 8.66 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 2.2 nM 8.66 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
AP2-associated protein kinase 1 IC50 = 2.2 nM 8.66 Kinase Assay: The assays were performed in U-bottom 384-well plates. The final a... -
AP2-associated protein kinase 1 IC50 = 2.2 nM 8.66 AAK1 Kinase Assay: The assays were performed in U-bottom 384-well plates. The fi... -
MAP kinase-interacting serine/threonine-protein kinase 1 IC50 = 160.0 nM 6.8 Inhibition of MNK1 (unknown origin) 35257579
Sodium-dependent noradrenaline transporter IC50 = 390.0 nM 6.41 Inhibition of NET (unknown origin) 35257579
Citron Rho-interacting kinase IC50 = 410.0 nM 6.39 Inhibition of CRIK (unknown origin) 35257579
Serine/threonine-protein kinase LATS2 IC50 = 660.0 nM 6.18 Inhibition of LATS2 (unknown origin) 35257579
Cyclin-G-associated kinase IC50 = 800.0 nM 6.1 Inhibition of GAK (unknown origin) 35257579
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 1400.0 nM 5.85 Inhibition of human ERG by patch clamp assay 35257579
BMP-2-inducible protein kinase IC50 = 1900.0 nM 5.72 Inhibition of BIKE (unknown origin) 35257579
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 5400.0 nM 5.27 Inhibition of BCRP (unknown origin) 35257579

Literature References

PubMed DOI Target Context # Activities
35257579 10.1021/acs.jmedchem.1c02131 ADMET 86
35257579 10.1021/acs.jmedchem.1c02131 No relevant target 12
35257579 10.1021/acs.jmedchem.1c02131 Rattus norvegicus 12
35257579 10.1021/acs.jmedchem.1c02131 Unchecked 10
35257579 10.1021/acs.jmedchem.1c02131 Cytochrome P450 3A4 7
38377825 10.1016/j.ejmech.2024.116232 SARS-CoV-2 4
35261239 10.1021/acs.jmedchem.1c02132 ADMET 3
38377825 10.1016/j.ejmech.2024.116232 AP2-associated protein kinase 1 2
35261239 10.1021/acs.jmedchem.1c02132 AP2-associated protein kinase 1 2
35257579 10.1021/acs.jmedchem.1c02131 AP2-associated protein kinase 1 2
35257579 10.1021/acs.jmedchem.1c02131 Aorta 1
35257579 10.1021/acs.jmedchem.1c02131 Cytochrome P450 1A2 1
35257579 10.1021/acs.jmedchem.1c02131 Cytochrome P450 1
35257579 10.1021/acs.jmedchem.1c02131 Cytochrome P450 2C9 1
35257579 10.1021/acs.jmedchem.1c02131 Cytochrome P450 2D6 1
35257579 10.1021/acs.jmedchem.1c02131 Cytochrome P450 2B6 1
35257579 10.1021/acs.jmedchem.1c02131 Voltage-gated inwardly rectifying potassium channel KCNH2 1
35257579 10.1021/acs.jmedchem.1c02131 Solute carrier organic anion transporter family member 1B1 1
38377825 10.1016/j.ejmech.2024.116232 Unchecked 1
35257579 10.1021/acs.jmedchem.1c02131 Bile salt export pump 1

Data from ChEMBL 36 via Core Engine