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Compound Detail

CHEMBL3787344

NAZARTINIB
🧪 Phase II
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🧪 Phase II
Cc1cc(C(=O)Nc2nc3cccc(Cl)c3n2[C@@H]2CCCCN(C(=O)/C=C/CN(C)C)C2)ccn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3787344
Name NAZARTINIB
Phase Phase II
Structure Type MOL
InChI Key IOMMMLWIABWRKL-WUTDNEBXSA-N

Known Names

EGF-816 Egf816 Nazartinib NVP-EGF816-NX
3
Targets
17
Activities
1
Assay Types
18
PK Parameters
18
Publications
4
Known Names
4
Indications
3
Mechanisms

Molecular Properties

495.0
MW (Da)
4.32
ALogP
6
HBA
1
HBD
83.4
PSA (Ų)
0.52
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -tinib
USAN Year 2018

Extended Properties

Molecular Formula C26H31ClN6O2
MW 495.03
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -1.15

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Epidermal growth factor receptor erbB1 inhibitor INHIBITOR Epidermal growth factor receptor ✓ ✓
Epidermal growth factor receptor inhibitor INHIBITOR Epidermal growth factor receptor ✓ ✓
Epidermal growth factor receptor inhibitor INHIBITOR Epidermal growth factor receptor ✓ ✓

Indications

Carcinoma, Non-Small-Cell Lung Lung Neoplasms Neoplasms Bronchial Neoplasms

Activity Summary

IC50 17 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.82 7.1322 1.5 9
Epidermal growth factor receptor
CHEMBL203
 IC50 8.38 7.7857 4.2 7
Cytochrome P450 2D6
CHEMBL289
 IC50 5.16 5.16 7000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6331.43 ng.hr.mL-1 Mus musculus
AUC 2644.95 ng.hr.mL-1 Mus musculus
AUC 3231.06 ng.hr.mL-1 Rattus norvegicus
AUC 5915.61 ng.hr.mL-1 Rattus norvegicus
CL 34.0 mL.min-1.g-1 Homo sapiens
CL 66.0 mL.min-1.g-1 Mus musculus
CL 31.6 mL.min-1.kg-1 Mus musculus
CL 15.7 mL.min-1.kg-1 Rattus norvegicus
CL 30.0 % Rattus norvegicus
CL 35.0 % Mus musculus
Cmax 2938.0 nM Mus musculus
Cmax 987.0 nM Rattus norvegicus
F 60.0 % Mus musculus
F 55.0 % Rattus norvegicus
MRT 1.5 hr Mus musculus
MRT 2.6 hr Rattus norvegicus
Tmax 0.83 hr Mus musculus
Tmax 3.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.52 nM 8.82 Inhibition of EGFR E746 to A750 deletion mutant phosphorylation in human patient... 27433829
Unchecked IC50 = 2.9 nM 8.54 Cytotoxicity against mouse Ba/F3 EGFR-Del19 cells assessed as inhibition of cell... 28287083
Epidermal growth factor receptor IC50 = 4.18 nM 8.38 Inhibition of EGFR L858R/T790M mutant phosphorylation in human patient derived H... 27433829
Epidermal growth factor receptor IC50 = 6.11 nM 8.21 Inhibition of EGFR L858R mutant phosphorylation in human patient derived H3255 c... 27433829
Unchecked IC50 = 7.7 nM 8.11 Cytotoxicity against mouse Ba/F3 EGFR-L858R cells assessed as inhibition of cell... 28287083
Epidermal growth factor receptor IC50 = 9.0 nM 8.05 Inhibition of EGFR L858R mutant in human H3255 cells assessed as suppression of ... 26968253
Epidermal growth factor receptor IC50 = 11.0 nM 7.96 Inhibition of EGFR Del ex19 mutant in human HCC827 cells assessed as suppression... 26968253
Unchecked IC50 = 15.5 nM 7.81 Cytotoxicity against mouse Ba/F3 EGFR-T790M/L858R cells assessed as inhibition o... 28287083
Unchecked IC50 = 18.5 nM 7.73 Cytotoxicity against mouse Ba/F3 EGFR-Del19/T790M cells assessed as inhibition o... 28287083
Epidermal growth factor receptor IC50 = 25.0 nM 7.6 Inhibition of EGFR L858R/T790M double mutant in human NCI-H1975 cells assessed a... 26968253
Epidermal growth factor receptor IC50 = 31.0 nM 7.51 Inhibition of EGFR L858R/T790M mutant (unknown origin) in human NCI-H1975 cells 36561076
Epidermal growth factor receptor IC50 = 160.6 nM 6.79 Inhibition of wild type EGFR phosphorylation in human HaCaT cells incubated for ... 27433829
Unchecked IC50 = 1241.0 nM 5.91 Cytotoxicity against mouse Ba/F3 EGFR-Del19/C797S cells assessed as inhibition o... 28287083
Unchecked IC50 = 1408.0 nM 5.85 Cytotoxicity against mouse Ba/F3 EGFR-Del19/T790M/C797S cells assessed as inhibi... 28287083
Unchecked IC50 = 1659.0 nM 5.78 Cytotoxicity against mouse Ba/F3 EGFR-C797S/L858R cells assessed as inhibition o... 28287083
Unchecked IC50 = 2278.0 nM 5.64 Cytotoxicity against mouse Ba/F3 EGFR-T790M/C797S/L858R cells assessed as inhibi... 28287083
Cytochrome P450 2D6 IC50 = 7000.0 nM 5.16 Inhibition of CYP2D6 (unknown origin) 27433829

Literature References

PubMed DOI Target Context # Activities
27433829 10.1021/acs.jmedchem.5b01985 ADMET 22
28287083 10.1038/ncomms14768 Unchecked 8
27433829 10.1021/acs.jmedchem.5b01985 Epidermal growth factor receptor 7
27433829 10.1021/acs.jmedchem.5b01985 NON-PROTEIN TARGET 5
27433829 10.1021/acs.jmedchem.5b01985 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
26968253 10.1016/j.bmcl.2016.02.067 Epidermal growth factor receptor 3
27433829 10.1021/acs.jmedchem.5b01985 No relevant target 2
27433829 10.1021/acs.jmedchem.5b01985 Mus musculus 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
27433829 10.1021/acs.jmedchem.5b01985 Cytochrome P450 3A4 1
27433829 10.1021/acs.jmedchem.5b01985 Cytochrome P450 2D6 1
27433829 10.1021/acs.jmedchem.5b01985 Cytochrome P450 2C9 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
36561076 10.1039/d2md00216g Epidermal growth factor receptor 1
- 10.6019/EOS300108 HepG2 1

Data from ChEMBL 36 via Core Engine