Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL1201179

LAPATINIB DITOSYLATE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CS(=O)(=O)CCNCc1ccc(-c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2)o1.Cc1ccc(S(=O)(=O)O)cc1.Cc1ccc(S(=O)(=O)O)cc1.O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201179
Name LAPATINIB DITOSYLATE
Phase Approved
Structure Type MOL
InChI Key XNRVGTHNYCNCFF-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL554
Active Moiety CHEMBL554

Known Names

GW-572016F GW572016F Lapatinib ditoluenesulfonate monohydrate Lapatinib ditosylate Lapatinib ditosylate anhydrous Lapatinib ditosylate monohydrate Lapatinib tosilate Lapatinib tosilate hydrate Tycerb Tykerb Tyverb
5
Targets
21
Activities
2
Assay Types
11
PK Parameters
20
Publications
11
Known Names
20
Indications
2
Mechanisms

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 C43H44ClFN4O11S3
MW 943.49
Aromatic Rings 5
Heavy Atoms 40
NP-Likeness -1.59

Mechanism of Action

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

Indications

Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms, Male Carcinoma, Squamous Cell Endometrial Neoplasms Gallbladder Neoplasms Gliosarcoma Hypopharyngeal Neoplasms Liver Neoplasms Liver Neoplasms Oropharyngeal Neoplasms Pancreatic Neoplasms Prostatic Neoplasms, Castration-Resistant Squamous Cell Carcinoma of Head and Neck Stomach Neoplasms Urinary Bladder Neoplasms Urinary Bladder Neoplasms Central Nervous System Neoplasms

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States

Activity Summary

IC50 19 meas. best 8.52
EC50 2 meas. best 7.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 8.52 7.9814 3.0 7
Epidermal growth factor receptor
CHEMBL203
 IC50 8.3 7.8029 5.0 7
HN5
CHEMBL614828
 EC50 7.82 7.82 15.0 1
BT-474
CHEMBL614529
 EC50 7.7 7.7 20.0 1
BT-474
CHEMBL614529
 IC50 7.43 7.1433 37.4 3
NCI-N87
CHEMBL614197
 IC50 7.33 7.33 46.2 1
HN5
CHEMBL614828
 IC50 6.92 6.92 120.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 26921.0 ng.hr.mL-1 Rattus norvegicus
AUC 26908.0 ng.hr.mL-1 Rattus norvegicus
AUC 3580.0 ng.hr.mL-1 Homo sapiens
Cmax 6715.2 nM Rattus norvegicus
Cmax 567.92 nM Homo sapiens
F 100.0 % Rattus norvegicus
MRT 5.52 hr Rattus norvegicus
T1/2 1.91 hr Rattus norvegicus
T1/2 14.8 hr Homo sapiens
Tmax 2.5 hr Rattus norvegicus
Tmax 4.05 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Receptor tyrosine-protein kinase erbB-2 IC50 = 3.0 nM 8.52 Inhibition of HER2 by HTRF assay 19815412
Epidermal growth factor receptor IC50 = 5.0 nM 8.3 Inhibition of EGFR by HTRF assay 19028424
Receptor tyrosine-protein kinase erbB-2 IC50 = 5.0 nM 8.3 Inhibition of ERBb2 by HTRF assay 19028424
Receptor tyrosine-protein kinase erbB-2 IC50 = 9.0 nM 8.05 Inhibition of ErbB2 19111461
Receptor tyrosine-protein kinase erbB-2 IC50 = 9.0 nM 8.05 Inhibition of HER2 by homogeneous time-resolved fluorescence assay 21334203
Receptor tyrosine-protein kinase erbB-2 IC50 = 9.0 nM 8.05 Inhibition of Her-2 by time-resolved fluorescence assay 22101132
Epidermal growth factor receptor IC50 = 10.0 nM 8.0 Inhibition of EGFR by homogeneous time-resolved fluorescence assay 21334203
Epidermal growth factor receptor IC50 = 10.0 nM 8.0 Inhibition of EGFR phosphorylation in EGF-stimulated human A431 after 2 hrs by W... 22101132
Receptor tyrosine-protein kinase erbB-2 IC50 = 10.3 nM 7.99 Inhibition of HER-2 (unknown origin) using poly-(Glu4-Tyr) as substrate after 1 ... 24121234
Epidermal growth factor receptor IC50 = 11.0 nM 7.96 Inhibition of EGFR 19111461
HN5 EC50 = 15.0 nM 7.82 Antiproliferative activity against human HN5 cells overexpressing EGFR after 3 d... 19028424
Epidermal growth factor receptor IC50 = 16.3 nM 7.79 Inhibition of EGFR (unknown origin) using poly-(Glu4-Tyr) as substrate after 1 h... 24121234
Epidermal growth factor receptor IC50 = 19.0 nM 7.72 Inhibition of EGFR by HTRF assay 19815412
BT-474 EC50 = 20.0 nM 7.7 Antiproliferative activity against human BT474 cells overexpressing ERBb2 after ... 19028424
BT-474 IC50 = 37.4 nM 7.43 Cytotoxicity against human BT474 cells after 72 hrs by SRB assay 24121234
NCI-N87 IC50 = 46.2 nM 7.33 Cytotoxicity against human NCI-N87 cells after 72 hrs by SRB assay 24121234
BT-474 IC50 = 100.0 nM 7.0 Antiproliferative activity against human BT474 cells expressing ErbB2 by MEB ass... 19111461
BT-474 IC50 = 100.0 nM 7.0 Antiproliferative activity against human BT474 cells by methylene blue staining ... 21334203
HN5 IC50 = 120.0 nM 6.92 Antiproliferative activity against human HN5 cells expressing EGFR by MEB assay 19111461
Receptor tyrosine-protein kinase erbB-2 IC50 = 124.0 nM 6.91 Inhibition of HER2 in human SKBR3 cells by HTRF assay 19815412

Literature References

PubMed DOI Target Context # Activities
24121234 10.1016/j.ejmech.2013.09.032 Rattus norvegicus 7
21965624 10.1124/dmd.111.040949 Homo sapiens 4
24121234 10.1016/j.ejmech.2013.09.032 NCI-N87 2
22101132 10.1016/j.bmcl.2011.10.103 NCI-N87 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19815412 10.1016/j.bmcl.2009.09.038 Receptor tyrosine-protein kinase erbB-2 2
19815412 10.1016/j.bmcl.2009.09.038 Epidermal growth factor receptor 2
21334203 10.1016/j.bmcl.2011.01.119 No relevant target 2
21334203 10.1016/j.bmcl.2011.01.119 Epidermal growth factor receptor 1
22101132 10.1016/j.bmcl.2011.10.103 Epidermal growth factor receptor 1
21334203 10.1016/j.bmcl.2011.01.119 Unchecked 1
21334203 10.1016/j.bmcl.2011.01.119 BT-474 1
21334203 10.1016/j.bmcl.2011.01.119 Receptor tyrosine-protein kinase erbB-2 1
19028424 10.1016/j.bmcl.2008.11.023 Epidermal growth factor receptor 1
19111461 10.1016/j.bmcl.2008.12.011 HN5 1
19111461 10.1016/j.bmcl.2008.12.011 Receptor tyrosine-protein kinase erbB-2 1
19111461 10.1016/j.bmcl.2008.12.011 Epidermal growth factor receptor 1
19028424 10.1016/j.bmcl.2008.11.023 BT-474 1
19028424 10.1016/j.bmcl.2008.11.023 HN5 1

Data from ChEMBL 36 via Core Engine