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Compound Detail

CHEMBL3647420

PYROTINIB
🧪 Phase III
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🧪 Phase III
CCOc1cc2ncc(C#N)c(Nc3ccc(OCc4ccccn4)c(Cl)c3)c2cc1NC(=O)/C=C/[C@H]1CCCN1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3647420
Name PYROTINIB
Phase Phase III
Structure Type MOL
InChI Key SADXACCFNXBCFY-IYNHSRRRSA-N

Known Names

Pyrotinib SHR-1258
14
Targets
25
Activities
1
Assay Types
0
PK Parameters
15
Publications
2
Known Names
8
Indications
2
Mechanisms

Molecular Properties

583.1
MW (Da)
6.47
ALogP
8
HBA
2
HBD
112.4
PSA (Ų)
0.20
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -tinib

Extended Properties

Molecular Formula C32H31ClN6O3
MW 583.09
Aromatic Rings 4
Heavy Atoms 42
NP-Likeness -1.39

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Epidermal growth factor receptor erbB1 inhibitor INHIBITOR Epidermal growth factor receptor ✓ ✓
Receptor protein-tyrosine kinase erbB-2 inhibitor INHIBITOR Receptor tyrosine-protein kinase erbB-2 ✓ ✓

Indications

Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Colorectal Neoplasms Digestive System Neoplasms Neoplasms Stomach Neoplasms Triple Negative Breast Neoplasms

Activity Summary

IC50 25 meas. best 9.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 9.32 8.225 0.5 6
NCI-N87
CHEMBL614197
 IC50 9.07 9.07 0.8 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 8.62 8.14 2.4 6
BT-474
CHEMBL614529
 IC50 8.4 8.4 4.0 1
SK-BR-3
CHEMBL613834
 IC50 7.85 7.85 14.0 1
BaF3
CHEMBL614524
 IC50 7.82 7.715 15.0 2
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 7.5 7.5 31.7 1
NUGC-4
CHEMBL613519
 IC50 7.22 7.22 60.8 1
MDA-MB-468
CHEMBL614335
 IC50 6.18 6.18 659.5 1
ES-2
CHEMBL5058622
 IC50 6.11 6.11 778.3 1
MFE-280
CHEMBL1075502
 IC50 5.81 5.81 1559.1 1
Unchecked
CHEMBL612545
 IC50 5.77 5.77 1688.5 1
COLO-678
CHEMBL1075425
 IC50 5.74 5.74 1837.0 1
NCI-H441
CHEMBL1075542
 IC50 5.72 5.72 1886.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 0.48 nM 9.32 Inhibition of EGFR (unknown origin) 35319895
NCI-N87 IC50 = 0.85 nM 9.07 Antiproliferative activity against human NCI-N87 cells assessed as inhibition of... 35319895
Epidermal growth factor receptor IC50 = 0.98 nM 9.01 Inhibition of wild type human N-terminal GST tagged EGFR (669 to 1210 residues) ... 35319895
Receptor tyrosine-protein kinase erbB-2 IC50 = 2.4 nM 8.62 Inhibition of HER2 R896C mutant (unknown origin) incubated for 120 mins in prese... 35319895
Receptor tyrosine-protein kinase erbB-2 IC50 = 3.91 nM 8.41 Inhibition of HER2 V777L mutant (unknown origin) incubated for 120 mins in prese... 35319895
BT-474 IC50 = 3.97 nM 8.4 Antiproliferative activity against human BT-474 cells assessed as inhibition of ... 35319895
Receptor tyrosine-protein kinase erbB-2 IC50 = 4.43 nM 8.35 Inhibition of HER2 (unknown origin) 35319895
Receptor tyrosine-protein kinase erbB-2 IC50 = 6.65 nM 8.18 Inhibition of HER2 D769H mutant (unknown origin) incubated for 120 mins in prese... 35319895
Receptor tyrosine-protein kinase erbB-2 IC50 = 9.07 nM 8.04 Inhibition of wild type human GST-tagged HER2 (676 to end residues) expressed in... 35319895
Epidermal growth factor receptor IC50 = 13.0 nM 7.89 Time-Resolved Fluorescence Assay: The following assay may be used to determine t... -
Epidermal growth factor receptor IC50 = 13.0 nM 7.89 Time-Resolved Fluorescence Assay: The following assay may be used to determine t... -
Epidermal growth factor receptor IC50 = 13.0 nM 7.89 Time-Resolved Fluorescence Assay: The following assay may be used to determine t... -
SK-BR-3 IC50 = 14.0 nM 7.85 Antiproliferative activity against human SK-BR-3 cells overexpressing wild type ... 35319895
BaF3 IC50 = 15.0 nM 7.82 Antiproliferative activity against mouse BaF3 cells harbouring HER2 A775_G77insY... 35319895
BaF3 IC50 = 24.67 nM 7.61 Antiproliferative activity against mouse BaF3 cells harboring HER2 YVMA mutant b... 38518121
Tyrosine-protein kinase BTK IC50 = 31.7 nM 7.5 Inhibition of BTK (unknown origin) measured by ADP-Glo assay 35939993
Epidermal growth factor receptor IC50 = 45.0 nM 7.35 Cell Proliferation Inhibition Assay: The following in vitro assay is to determin... -
Receptor tyrosine-protein kinase erbB-2 IC50 = 57.36 nM 7.24 Inhibition of HER2 D769Y mutant (unknown origin) incubated for 120 mins in prese... 35319895
NUGC-4 IC50 = 60.8 nM 7.22 Antiproliferative activity against human NUGC-4 cells assessed as cell growth in... 35319895
MDA-MB-468 IC50 = 659.49 nM 6.18 Antiproliferative activity against human MDA-MB-468 cells overexpressing wild ty... 35319895

Literature References

PubMed DOI Target Context # Activities
35319895 10.1021/acs.jmedchem.1c00710 Receptor tyrosine-protein kinase erbB-2 6
35319895 10.1021/acs.jmedchem.1c00710 Epidermal growth factor receptor 2
35319895 10.1021/acs.jmedchem.1c00710 Unchecked 2
35319895 10.1021/acs.jmedchem.1c00710 NCI-N87 2
35319895 10.1021/acs.jmedchem.1c00710 BT-474 2
35319895 10.1021/acs.jmedchem.1c00710 BaF3 2
35939993 10.1016/j.ejmech.2022.114611 Tyrosine-protein kinase BTK 1
35319895 10.1021/acs.jmedchem.1c00710 NCI-H441 1
35319895 10.1021/acs.jmedchem.1c00710 SK-BR-3 1
35319895 10.1021/acs.jmedchem.1c00710 MDA-MB-468 1
35319895 10.1021/acs.jmedchem.1c00710 ES-2 1
35319895 10.1021/acs.jmedchem.1c00710 MFE-280 1
35319895 10.1021/acs.jmedchem.1c00710 NUGC-4 1
35319895 10.1021/acs.jmedchem.1c00710 COLO-678 1
38518121 10.1021/acs.jmedchem.3c02302 BaF3 1

Data from ChEMBL 36 via Core Engine