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Compound Detail

CHEMBL554

LAPATINIB
💊 Approved Drug
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💊 Approved Drug
CS(=O)(=O)CCNCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL554
Name LAPATINIB
Phase Approved
Structure Type MOL
InChI Key BCFGMOOMADDAQU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

GSK-572016 GW-2016 GW-572016 GW-572016X GW572016 Lapatinib Tyverb
243
Targets
834
Activities
4
Assay Types
11
PK Parameters
20
Publications
7
Known Names
20
Indications

Molecular Properties

581.1
MW (Da)
6.14
ALogP
8
HBA
2
HBD
106.3
PSA (Ų)
0.18
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2007
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -tinib
USAN Year 2003

Extended Properties

Molecular Formula C29H26ClFN4O4S
MW 581.07
Aromatic Rings 5
Heavy Atoms 40
NP-Likeness -1.59

Indications

Brain Diseases Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Head and Neck Neoplasms Head and Neck Neoplasms Neoplasms Neoplasms Sarcoma Adenocarcinoma Bile Duct Neoplasms Brain Neoplasms Carcinoma, Ductal Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Carcinoma, Squamous Cell Colorectal Neoplasms Colorectal Neoplasms Esophageal Neoplasms

ATC Classification

L01EH01
lapatinib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 731 meas. best 10.22
Kd 80 meas. best 9.05
EC50 14 meas. best 7.0
Ki 9 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 10.22 7.3484 0.1 89
Epidermal growth factor receptor
CHEMBL203
 Kd 9.05 8.4211 0.9 46
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 Ki 8.8 8.8 1.6 2
SK-BR-3
CHEMBL613834
 IC50 8.7 6.75 2.0 10
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 8.57 7.1659 2.7 56
Epidermal growth factor receptor
CHEMBL203
 Ki 8.52 8.52 3.0 1
SK-OV-3
CHEMBL614925
 IC50 8.52 7.02 3.0 2
CAL-27
CHEMBL1075408
 IC50 8.15 7.215 7.0 2
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 Kd 8.15 8.112 7.0 5
4T1
CHEMBL612589
 IC50 7.98 6.545 10.4 2
MCF7
CHEMBL387
 IC50 7.96 5.5216 11.0 19
HCT-116
CHEMBL394
 IC50 7.92 5.4057 12.0 7
MDA-MB-231
CHEMBL400
 IC50 7.7 5.315 20.0 8
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 Ki 7.6 7.6 25.1 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.6 5.6865 25.0 46
BT-474
CHEMBL614529
 IC50 7.6 7.2225 25.0 8
HN5
CHEMBL614828
 IC50 7.6 7.26 25.0 2
NCI-H1648
CHEMBL2366214
 IC50 7.59 7.59 25.4 1
MDA-MB-435
CHEMBL614697
 IC50 7.53 7.53 29.7 1
NCI-N87
CHEMBL614197
 IC50 7.44 7.254 36.0 5
WI-38
CHEMBL614391
 IC50 7.34 7.34 45.2 1
HCC2218
CHEMBL2366221
 IC50 7.27 7.27 53.3 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 Kd 7.27 7.27 54.0 4
Unchecked
CHEMBL612545
 IC50 7.27 5.2425 54.0 12
Unchecked
CHEMBL612545
 Kd 7.27 7.27 54.0 1
OCUB-M
CHEMBL2366121
 IC50 7.24 7.24 57.4 1
AU565
CHEMBL1075393
 IC50 7.19 7.19 64.0 1
MDA-MB-468
CHEMBL614335
 IC50 7.08 5.44 83.2 4
ECC12
CHEMBL2366180
 IC50 7.04 7.04 92.3 1
DSH1
CHEMBL2366079
 IC50 7.03 7.03 94.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 EC50 7.0 6.9233 99.0 3
Calu-3
CHEMBL614534
 IC50 7.0 6.835 100.0 2
Epidermal growth factor receptor
CHEMBL203
 EC50 6.98 6.98 105.0 1
A-431
CHEMBL614069
 IC50 6.98 5.8025 104.0 12
HeLa
CHEMBL399
 IC50 6.92 6.075 120.0 2
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 6.72 6.52 190.0 3
MDA-MB-453
CHEMBL614334
 IC50 6.72 6.49 190.0 2
BB30-HNC
CHEMBL2366271
 IC50 6.61 6.61 246.5 1
HepG2
CHEMBL395
 IC50 6.57 5.4075 270.0 4
EKVX
CHEMBL614487
 IC50 6.35 6.35 448.7 1
TE-12
CHEMBL2366278
 IC50 6.31 6.31 490.6 1
Plasmodium falciparum
CHEMBL364
 EC50 6.28 6.28 530.0 1
HCC827
CHEMBL4296422
 IC50 6.22 6.22 600.0 2
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta
CHEMBL5554
 Kd 6.17 6.17 670.0 2
A388
CHEMBL2366355
 IC50 6.14 6.14 722.6 1
TE-9
CHEMBL2366147
 IC50 6.13 6.13 744.5 1
Phosphatidylinositol 4-kinase beta
CHEMBL3268
 Kd 6.03 6.03 940.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.0 6.0 1000.0 1
MDA-MB-361
CHEMBL614129
 IC50 5.99 5.99 1029.0 1
Dual specificity mitogen-activated protein kinase kinase 5
CHEMBL4948
 Kd 5.96 5.96 1100.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1.06 nmol/100.000 cells x h Homo sapiens
AUC 3893.17 ng.hr.mL-1 Mus musculus
AUC 26037.75 ng.hr.mL-1 Mus musculus
AUC 644.99 ng.hr.mL-1 Mus musculus
CL 36.31 mL.min-1.g-1 Homo sapiens
CL 91.2 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 73.7 mL.min-1.g-1 Mus musculus
CL 16.7 mL.min-1.g-1 Homo sapiens
Cmax 4180.0 nM Homo sapiens
Cmax 1470.0 nM Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 0.06 nM 10.22 Inhibition of human N-terminal GST-tagged EGFR (669 to 1210 residues) expressed ... 32931277
Epidermal growth factor receptor IC50 = 0.2 nM 9.7 Inhibition of human N-terminal GST-tagged EGFR L858R mutant (669 to 1210 residue... 32931277
Epidermal growth factor receptor Kd = 0.9 nM 9.05 Selectivity interaction (Kinome Scan (DiscoverX, competition-binding assay)) EUB... -
Epidermal growth factor receptor Kd = 0.92 nM 9.04 Binding constant for EGFR(G719C) kinase domain 18183025
Epidermal growth factor receptor Kd = 0.92 nM 9.04 Binding constant for EGFR(G719C) kinase domain 22037378
Epidermal growth factor receptor Kd = 0.92 nM 9.04 Selectivity interaction (Kinase panel (literature)) EUB0001487a EGFR -
Epidermal growth factor receptor Kd = 1.2 nM 8.92 Binding constant for EGFR(L861Q) kinase domain 18183025
Epidermal growth factor receptor Kd = 1.2 nM 8.92 Binding constant for EGFR(L861Q) kinase domain 22037378
Epidermal growth factor receptor Kd = 1.2 nM 8.92 Selectivity interaction (Kinase panel (literature)) EUB0001487a EGFR -
Epidermal growth factor receptor Kd = 1.2 nM 8.92 Selectivity interaction (Kinome Scan (DiscoverX, competition-binding assay)) EUB... -
Receptor tyrosine-protein kinase erbB-2 Ki = 1.585 nM 8.8 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Receptor tyrosine-protein kinase erbB-2 Ki = 1.585 nM 8.8 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Epidermal growth factor receptor IC50 = 1.8 nM 8.74 Inhibition of probe binding to EGFR L858R mutant (unknown origin) using rabbit r... 31023512
SK-BR-3 IC50 = 2.0 nM 8.7 Cytotoxicity against human SKBR3 cells overexpressing HER2 by resazurin dye redu... 21080629
Epidermal growth factor receptor Kd = 2.1 nM 8.68 Selectivity interaction (Kinome Scan (DiscoverX, competition-binding assay)) EUB... -
Epidermal growth factor receptor Kd = 2.1 nM 8.68 Selectivity interaction (Kinase panel (literature)) EUB0001487a EGFR -
Epidermal growth factor receptor Kd = 2.1 nM 8.68 Binding constant for EGFR(G719S) kinase domain 22037378
Epidermal growth factor receptor Kd = 2.1 nM 8.68 Binding constant for EGFR(G719S) kinase domain 18183025
Epidermal growth factor receptor Kd = 2.2 nM 8.66 Binding constant for EGFR(L747-E749del, A750P) kinase domain 22037378
Epidermal growth factor receptor Kd = 2.2 nM 8.66 Selectivity interaction (Kinome Scan (DiscoverX, competition-binding assay)) EUB... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5465560 Epidermal growth factor receptor 33
22169601 10.1016/j.bmc.2011.11.023 NON-PROTEIN TARGET 28
- 10.6019/CHEMBL5444388 Epidermal growth factor receptor 24
- 10.6019/CHEMBL5444388 Receptor tyrosine-protein kinase erbB-2 24
25305330 10.1016/j.ejmech.2014.10.006 BT-474 21
33314925 10.1021/acs.jmedchem.0c01647 Receptor tyrosine-protein kinase erbB-2 15
- 10.6019/CHEMBL5465560 Tyrosine-protein kinase ABL1 15
22037378 10.1038/nbt.1990 Tyrosine-protein kinase ABL1 15
22511346 10.1124/dmd.112.044958 Cytochrome P450 3A5 14
33545637 10.1016/j.ejmech.2021.113222 Mus musculus 14
30973735 10.1021/acs.jmedchem.9b00350 Unchecked 14
22037378 10.1038/nbt.1990 Epidermal growth factor receptor 12
23404373 10.1124/dmd.113.051151 Cytochrome P450 3A4 12
22037378 10.1038/nbt.1990 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 10
- 10.6019/CHEMBL5465560 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 10
18183025 10.1038/nbt1358 Epidermal growth factor receptor 10
23404373 10.1124/dmd.113.051151 Cytochrome P450 3A5 10
- 10.6019/CHEMBL5303304 U2OS 9
33314925 10.1021/acs.jmedchem.0c01647 Unchecked 9
26254279 10.18632/oncotarget.4214 Epidermal growth factor receptor and ErbB2 (HER1 and HER2) 9

Data from ChEMBL 36 via Core Engine