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Compound Detail

CHEMBL2105712

AFATINIB DIMALEATE
💊 Approved Drug
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💊 Approved Drug
CN(C)C/C=C/C(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[C@H]1CCOC1.O=C(O)/C=C\C(=O)O.O=C(O)/C=C\C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2105712
Name AFATINIB DIMALEATE
Phase Approved
Structure Type MOL
InChI Key USNRYVNRPYXCSP-JUGPPOIOSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL1173655
Active Moiety CHEMBL1173655

Known Names

Afatinib dimaleate Afatinib maleate BIBW-2992 MA2 BIBW-2992-MA2 BIBW-2992MA2 BIBW2992 MA2 BIBW2992-MA2 Gilotrif Giotrif
13
Targets
33
Activities
3
Assay Types
0
PK Parameters
20
Publications
9
Known Names
2
Indications
3
Mechanisms

Molecular Properties

485.9
MW (Da)
4.39
ALogP
7
HBA
2
HBD
88.6
PSA (Ų)
0.46
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -tinib
USAN Year 2010

Extended Properties

Molecular Formula C32H33ClFN5O11
MW 718.09
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.14

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 ✓ ✓
Receptor protein-tyrosine kinase erbB-4 inhibitor INHIBITOR Receptor tyrosine-protein kinase erbB-4 ✓ ✓

Indications

Carcinoma, Non-Small-Cell Lung Multiple Myeloma

Activity Summary

Kd 21 meas. best 9.52
IC50 10 meas. best 9.4
EC50 2 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 Kd 9.52 9.52 0.3 1
Epidermal growth factor receptor
CHEMBL203
 IC50 9.4 8.135 0.4 4
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 Kd 8.3 8.3 5.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 Kd 8.2 8.2 6.3 1
Epidermal growth factor receptor
CHEMBL203
 EC50 7.89 7.89 13.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 7.85 6.845 14.0 2
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 EC50 7.46 7.46 35.0 1
Cyclin-G-associated kinase
CHEMBL4355
 Kd 7.1 7.1 79.0 1
Tyrosine-protein kinase Blk
CHEMBL2250
 Kd 6.66 6.66 220.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 Kd 6.64 6.258 230.0 10
Interleukin-1 receptor-associated kinase 1
CHEMBL3357
 Kd 6.62 6.62 240.0 1
Ephrin type-A receptor 6
CHEMBL4526
 Kd 6.47 6.47 340.0 1
Homeodomain-interacting protein kinase 4
CHEMBL1075167
 Kd 6.44 6.44 360.0 1
Phosphorylase b kinase gamma catalytic chain, liver/testis isoform
CHEMBL2349
 Kd 6.33 6.33 470.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 Kd 6.24 6.24 570.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 6.13 6.13 736.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 Kd 6.01 6.01 970.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 5.93 5.93 1180.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 5.84 5.84 1437.0 1
Hepatocyte growth factor receptor
CHEMBL3717
 IC50 4.89 4.89 13000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor Kd = 0.3 nM 9.52 Affinity Biochemical interaction (Competition binding assay (DiscoverX)) EUB0000... -
Epidermal growth factor receptor IC50 = 0.4 nM 9.4 Selectivity interaction (Enzymatic activity assay) EUB0000596aBDA EGFR -
Epidermal growth factor receptor IC50 = 0.5 nM 9.3 Selectivity interaction (Enzymatic activity assay) EUB0000596aBDA EGFR -
Receptor tyrosine-protein kinase erbB-2 Kd = 5.0 nM 8.3 Affinity Biochemical interaction (Competition binding assay (DiscoverX)) EUB0000... -
Receptor tyrosine-protein kinase erbB-4 Kd = 6.3 nM 8.2 Affinity Biochemical interaction (Competition binding assay (DiscoverX)) EUB0000... -
Epidermal growth factor receptor IC50 = 10.0 nM 8.0 Selectivity interaction (Enzymatic activity assay) EUB0000596aBDA EGFR -
Epidermal growth factor receptor EC50 = 13.0 nM 7.89 Affinity On-target Cellular interaction (EGFR-phosphorylation in A431 cells) EUB... -
Receptor tyrosine-protein kinase erbB-4 IC50 = 14.0 nM 7.85 Selectivity interaction (Enzymatic activity assay) EUB0000596aBDA ERBB4 -
Receptor tyrosine-protein kinase erbB-2 EC50 = 35.0 nM 7.46 Affinity On-target Cellular interaction (HER2-phosphorylation in BT-474 cells) E... -
Cyclin-G-associated kinase Kd = 79.0 nM 7.1 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Tyrosine-protein kinase Blk Kd = 220.0 nM 6.66 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Tyrosine-protein kinase ABL1 Kd = 230.0 nM 6.64 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Interleukin-1 receptor-associated kinase 1 Kd = 240.0 nM 6.62 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Ephrin type-A receptor 6 Kd = 340.0 nM 6.47 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Homeodomain-interacting protein kinase 4 Kd = 360.0 nM 6.44 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Tyrosine-protein kinase ABL1 Kd = 380.0 nM 6.42 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Tyrosine-protein kinase ABL1 Kd = 420.0 nM 6.38 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Phosphorylase b kinase gamma catalytic chain, liver/testis isoform Kd = 470.0 nM 6.33 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Tyrosine-protein kinase ABL1 Kd = 500.0 nM 6.3 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Tyrosine-protein kinase Lck Kd = 570.0 nM 6.24 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 U2OS 262
- 10.6019/CHEMBL4689842 Fibroblast 262
- 10.6019/CHEMBL4689842 HEK-293T 260
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5212743 Tyrosine-protein kinase ABL1 11
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.6019/CHEMBL5212743 Epidermal growth factor receptor 3
26310890 10.1016/j.ejmech.2015.08.026 Mus musculus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
26310890 10.1016/j.ejmech.2015.08.026 NCI-H1975 2
- 10.6019/CHEMBL5212743 Tyrosine-protein kinase Lck 2
- 10.6019/CHEMBL5060014 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5724564 Hepatocyte spheroids 1
- 10.6019/CHEMBL5060014 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5060014 Peregrin 1
- 10.6019/CHEMBL5060014 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5060014 Aurora kinase A 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
26310890 10.1016/j.ejmech.2015.08.026 NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine