Compound Detail

CHEMBL939

GEFITINIB

💊 Approved Drug

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💊 Approved Drug

COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN1CCOCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL939
Name	GEFITINIB
Phase	Approved
Structure Type	MOL
InChI Key	XGALLCVXEZPNRQ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Gefitinib Gefitinib mylan Iressa NSC-759856 ZD-1839 ZD1839

712

Targets

1,644

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

446.9

MW (Da)

4.28

ALogP

HBA

HBD

68.7

PSA (Å²)

0.52

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2003
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

USAN Stem	-tinib
USAN Year	2002

Extended Properties

Molecular Formula	C22H24ClFN4O3
MW	446.91
Aromatic Rings	3
Heavy Atoms	31
NP-Likeness	-1.75

Mechanism of Action

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

Indications

Carcinoma, Non-Small-Cell Lung Neoplasms Neoplasms Adenocarcinoma of Lung Adenocarcinoma, Bronchiolo-Alveolar Breast Neoplasms Breast Neoplasms Carcinoma, Squamous Cell Carcinoma, Squamous Cell Carcinoma, Squamous Cell Head and Neck Neoplasms Head and Neck Neoplasms Lung Neoplasms Lung Neoplasms Lung Neoplasms Urinary Bladder Neoplasms Bile Duct Neoplasms Breast Neoplasms, Male Central Nervous System Neoplasms Colorectal Neoplasms

ATC Classification

L01EB01

gefitinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 1,360 meas. best 10.0

Kd 191 meas. best 9.28

Ki 73 meas. best 9.4

EC50 20 meas. best 8.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Epidermal growth factor receptor CHEMBL203	IC50	10.0	7.5918	0.1	227
HCC827 CHEMBL4296422	IC50	9.64	7.73	0.2	22
Epidermal growth factor receptor CHEMBL203	Ki	9.4	8.3811	0.4	9
Epidermal growth factor receptor CHEMBL203	Kd	9.28	8.5763	0.5	38
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.82	6.5248	1.5	29
BaF3 CHEMBL614524	IC50	8.7	6.8727	2.0	26
Unchecked CHEMBL612545	IC50	8.57	5.5878	2.7	55
Receptor-interacting serine/threonine-protein kinase 2 CHEMBL5014	IC50	8.42	7.68	3.8	3
EOL1 CHEMBL614489	IC50	8.29	8.29	5.2	1
PC-9 CHEMBL614102	IC50	8.21	6.9718	6.1	11
A549 CHEMBL392	IC50	8.15	5.1086	7.0	63
NCI-H3255 CHEMBL4296476	IC50	8.15	7.3571	7.0	7
Cyclin-G-associated kinase CHEMBL4355	Kd	8.15	7.7111	7.0	9
HN5 CHEMBL614828	EC50	8.0	8.0	10.0	1
Epidermal growth factor receptor CHEMBL3608	IC50	7.84	7.84	14.4	1
PC-9 CHEMBL614102	EC50	7.77	6.465	17.0	2
NCI-H292 CHEMBL614733	IC50	7.7	6.904	20.0	5
Receptor tyrosine-protein kinase erbB-2 CHEMBL1824	IC50	7.62	6.277	24.0	23
Receptor tyrosine-protein kinase erbB-2 CHEMBL1824	Ki	7.6	7.6	25.1	2
NCI-H720 CHEMBL2366105	IC50	7.57	7.57	26.9	1
SNU-5 CHEMBL614934	IC50	7.55	7.55	28.2	1
HUVEC CHEMBL613979	IC50	7.52	6.5067	30.0	3
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	7.48	5.9333	33.0	6
Epidermal growth factor receptor CHEMBL203	EC50	7.46	6.0333	35.0	3
EW-3 CHEMBL2366307	IC50	7.34	7.34	46.0	1
HCC2218 CHEMBL2366221	IC50	7.3	7.3	50.6	1
HCC4006 CHEMBL4523575	IC50	7.3	7.3	50.0	1
FaDu CHEMBL612250	IC50	7.3	6.76	50.0	2
KB CHEMBL398	IC50	7.27	6.2875	54.0	4
Transcription factor p65 CHEMBL5533	IC50	7.26	7.26	55.0	1
HuO-3N1 CHEMBL1075475	IC50	7.25	7.25	56.1	1
LoVo CHEMBL614721	IC50	7.23	6.65	59.0	2
HSC-4 CHEMBL1075469	IC50	7.21	7.21	61.5	1
DB CHEMBL2366331	IC50	7.21	7.21	61.0	1
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	Kd	7.16	7.16	69.0	1
KB 3-1 CHEMBL614590	IC50	7.1	7.1	80.0	1
DOK CHEMBL1075435	IC50	7.03	7.03	93.6	1
NCI-H1993 CHEMBL1075527	IC50	7.0	5.5233	100.0	3
Tyrosine-protein kinase HCK CHEMBL3234	IC50	6.96	6.96	110.0	1
HepG2 CHEMBL395	IC50	6.92	5.0127	120.0	15
H9 CHEMBL614806	IC50	6.86	6.86	137.2	1
Receptor tyrosine-protein kinase erbB-4 CHEMBL3009	Ki	6.8	6.8	158.5	2
Tyrosine-protein kinase Lyn CHEMBL3905	Ki	6.8	6.8	158.5	2
HSC-2 CHEMBL1075468	IC50	6.78	6.78	165.6	1
Lu-65 CHEMBL614694	IC50	6.78	6.78	166.6	1
BV-173 CHEMBL2366145	IC50	6.73	6.73	186.6	1
LB2241-RCC CHEMBL2366330	IC50	6.71	6.71	194.9	1
KG-1 CHEMBL612264	IC50	6.69	6.69	204.3	1
CHL-1 CHEMBL1075422	IC50	6.68	6.68	208.5	1
KYSE-140 CHEMBL1075484	IC50	6.68	6.68	210.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	143.01	ng.hr.mL-1	Rattus norvegicus
AUC	35171.82	ng.hr.mL-1	Mus musculus
AUC	38389.57	ng.hr.mL-1	Mus musculus
AUC	2523.7	ng.hr.mL-1	Rattus norvegicus
AUC	41.56	ng.hr.mL-1	Rattus norvegicus
AUC	14260.9	ng.hr.mL-1	Rattus norvegicus
AUC	2371.1	ng.hr.mL-1	Rattus norvegicus
AUC	2356.79	ng.hr.mL-1	Rattus norvegicus
AUC	500.8	ng.hr.mL-1	Rattus norvegicus
AUC	490.6	ng.hr.mL-1	Rattus norvegicus
AUC	2402.14	ng.hr.mL-1	Homo sapiens
AUC	7722.0	ng.hr.mL-1	Rattus norvegicus
AUC	7803.0	ng.hr.mL-1	Rattus norvegicus
CL	68.0	mL.min-1.kg-1	Rattus norvegicus
CL	12.0	mL.min-1.kg-1	Homo sapiens
CL	70.31	mL.min-1.kg-1	Rattus norvegicus
CL	33.81	mL.min-1.kg-1	Rattus norvegicus
CL	21.83	mL.min-1.kg-1	Rattus norvegicus
CL	94.0	mL.min-1.kg-1	Homo sapiens
CL	57.0	mL.min-1.kg-1	Rattus norvegicus
CL	17.0	mL.min-1.kg-1	Homo sapiens
CL	32.0	mL.min-1.kg-1	Rattus norvegicus
CL	46.0	mL.min-1.g-1	Homo sapiens
Cmax	8100.0	nM	Mus musculus
Cmax	6700.0	nM	Mus musculus
Cmax	2691.82	nM	Rattus norvegicus
Cmax	1390.21	nM	Rattus norvegicus
Cmax	356.0	nM	Homo sapiens
F	56.0	%	Rattus norvegicus
F	60.0	%	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Epidermal growth factor receptor	IC50	=	0.1	nM	10.0	Inhibition of wild type EGFR (unknown origin) using fluoresceine-labelled poly-G...	34464874
Epidermal growth factor receptor	IC50	=	0.1	nM	10.0	Inhibition of EGFR (unknown origin) after 1.5 hr by FRET-based Z-lyte assay	24607591
Epidermal growth factor receptor	IC50	=	0.1	nM	10.0	Inhibition of wild type EGFR (unknown origin) using Tyr 4 peptide as substrate a...	23792318
Epidermal growth factor receptor	IC50	=	0.1	nM	10.0	Inhibition of wild type EGFR (unknown origin) after 1.5 hrs by FRET-based Z'Lyte...	23668441
Epidermal growth factor receptor	IC50	=	0.15	nM	9.82	Inhibition of recombinant human GST-tagged EGFR cytoplasmic domain (668 to 1210 ...	28236592
Epidermal growth factor receptor	IC50	=	0.17	nM	9.77	Inhibition of recombinant human GST-tagged EGFR L858R mutant cytoplasmic domain ...	28236592
Epidermal growth factor receptor	IC50	=	0.2	nM	9.7	Inhibition of EGFR L858R mutant (unknown origin) after 1.5 hr by FRET-based Z-ly...	24607591
Epidermal growth factor receptor	IC50	=	0.2	nM	9.7	Inhibition of EGFR L858R mutant (unknown origin) using Tyr 4 peptide as substrat...	23792318
Epidermal growth factor receptor	IC50	=	0.2	nM	9.7	Inhibition of EGFR L858R mutant (unknown origin) after 1.5 hrs by FRET-based Z'L...	23668441
HCC827	IC50	=	0.23	nM	9.64	Antiproliferative activity against human HCC827 cells by CellTiter-Glo assay	38518121
Epidermal growth factor receptor	IC50	=	0.2512	nM	9.6	Inhibition of wild type N-terminal GST-tagged EGFR (669 to 1210 residues) (unkno...	38746885
Epidermal growth factor receptor	IC50	=	0.32	nM	9.49	Inhibition of wild type EGFR (unknown origin) using fluoresceine-labelled poly-G...	34464874
Epidermal growth factor receptor	Ki	=	0.4	nM	9.4	Inhibition of EGFR	15975507
Epidermal growth factor receptor	Ki	=	0.4	nM	9.4	Binding affinity to EGFR (unknown origin) assessed as inhibition constant	38852338
Epidermal growth factor receptor	IC50	=	0.45	nM	9.35	Inhibition of wild type EGFR (unknown origin) by Z'-Lyte kinase assay	25462282
Epidermal growth factor receptor	IC50	=	0.45	nM	9.35	Inhibition of wild type EGFR (unknown origin) by Z'-Lyte kinase assay	25468044
Epidermal growth factor receptor	IC50	=	0.458	nM	9.34	Kinase Assay (EGFR/L858R): Kinase Assay Protocol:Bar-coded Corning, low volume N...	-
Epidermal growth factor receptor	IC50	=	0.47	nM	9.33	Inhibition of recombinant human wild type GST-tagged EGFR (668 to 1210 residues)...	30472599
Epidermal growth factor receptor	IC50	=	0.5	nM	9.3	Inhibition of recombinant human N-terminal GST tagged EGFR (669 to 1210 residues...	29523467
Epidermal growth factor receptor	IC50	=	0.509	nM	9.29	Inhibition of recombinant human EGFR expressed in baculovirus by fluorescence ba...	27288180

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	649
-	10.6019/CHEMBL3885881	Rattus norvegicus	408
28245116	10.1021/acs.jmedchem.6b01489	Rattus norvegicus	24
37934858	10.1021/acs.jmedchem.3c01669	ADMET	23
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
26560049	10.1016/j.ejmech.2015.10.045	A549	15
18089823	10.1158/0008-5472.can-07-1885	BaF3	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
12384534	-	Epidermal growth factor receptor	13
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
32739648	10.1016/j.ejmech.2020.112640	Epidermal growth factor receptor	12
20033049	10.1038/nature08622	BaF3	11
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
18183025	10.1038/nbt1358	Epidermal growth factor receptor	10
30471829	10.1016/j.bmc.2018.11.009	NCI-H1975	10
29421573	10.1016/j.ejmech.2018.01.090	Epidermal growth factor receptor	9
27288180	10.1016/j.bmc.2016.05.063	Epidermal growth factor receptor	9
-	10.6019/CHEMBL4689842	U2OS	9
28711702	10.1016/j.ejmech.2017.07.005	Epidermal growth factor receptor	9
16806916	10.1016/j.bmcl.2006.06.054	Mus musculus	9

Data from ChEMBL 36 via Core Engine