Compound Detail

CHEMBL1289926

AXITINIB

💊 Approved Drug

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💊 Approved Drug

CNC(=O)c1ccccc1Sc1ccc2c(/C=C/c3ccccn3)n[nH]c2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1289926
Name	AXITINIB
Phase	Approved
Structure Type	MOL
InChI Key	RITAVMQDGBJQJZ-FMIVXFBMSA-N
Therapeutic	✓ Yes

Known Names

AG-013736 AG-13736 Axitinib Inlyta NSC-757441

574

Targets

807

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

386.5

MW (Da)

4.64

ALogP

HBA

HBD

70.7

PSA (Å²)

0.52

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2012
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-tinib
USAN Year	2005

Extended Properties

Molecular Formula	C22H18N4OS
MW	386.48
Aromatic Rings	4
Heavy Atoms	28
NP-Likeness	-1.43

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Vascular endothelial growth factor receptor inhibitor	INHIBITOR	Vascular endothelial growth factor receptor	✓	✓

Indications

Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Neoplasms Neoplasms Carcinoma, Pancreatic Ductal Kidney Neoplasms Kidney Neoplasms Adrenal Cortex Neoplasms Biliary Tract Neoplasms Carcinoid Tumor Carcinoma, Adenoid Cystic Carcinoma, Hepatocellular Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Colorectal Neoplasms Colorectal Neoplasms

ATC Classification

L01EK01

axitinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 639 meas. best 10.7

Kd 161 meas. best 9.31

Ki 7 meas. best 9.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	10.7	9.4557	0.0	7
EOL1 CHEMBL614489	IC50	10.29	10.29	0.1	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	10.0	10.0	0.1	2
Vascular endothelial growth factor receptor 3 CHEMBL1955	IC50	10.0	10.0	0.1	2
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	9.7	8.4813	0.2	8
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	9.7	9.06	0.2	2
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	9.31	7.722	0.5	10
NON-PROTEIN TARGET CHEMBL3879801	IC50	9.3	8.935	0.5	2
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	9.29	9.29	0.5	1
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	9.24	7.815	0.6	2
NCI-H1703 CHEMBL1075522	IC50	9.04	9.04	0.9	1
Aurora kinase C CHEMBL3935	Kd	8.89	8.89	1.3	1
Unchecked CHEMBL612545	IC50	8.89	5.82	1.3	20
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	8.82	6.995	1.5	16
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	8.8	8.8	1.6	1
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	8.77	8.77	1.7	1
Serine/threonine-protein kinase PLK4 CHEMBL3788	IC50	8.38	7.6075	4.2	4
Serine/threonine-protein kinase PLK4 CHEMBL3788	Ki	8.38	8.38	4.2	3
Vascular endothelial growth factor receptor 1 CHEMBL1868	Kd	8.24	8.24	5.8	1
Vascular endothelial growth factor receptor 2 CHEMBL279	Kd	8.23	8.23	5.9	1
Kasumi 1 CHEMBL613988	IC50	8.17	8.17	6.8	1
CGTH-W-1 CHEMBL2366300	IC50	8.14	8.14	7.2	1
A204 CHEMBL614514	IC50	8.0	8.0	9.9	1
Aurora kinase B CHEMBL2185	Kd	7.96	7.295	11.0	2
Serine/threonine-protein kinase PLK4 CHEMBL3788	Kd	7.8	6.97	16.0	2
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Kd	7.68	7.68	21.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	7.51	6.6943	31.0	7
Fibroblast growth factor receptor 1 CHEMBL3650	Ki	7.25	7.25	56.0	1
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	7.16	6.57	70.0	2
Aurora kinase A CHEMBL4722	Kd	7.14	6.785	72.0	2
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	IC50	7.11	7.11	78.0	1
Tyrosine-protein kinase receptor Tie-1 CHEMBL5274	Kd	7.01	7.01	97.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	7.0	6.518	100.0	5
H-EMC-SS CHEMBL1075451	IC50	6.96	6.96	110.0	1
Fibroblast growth factor receptor 2 CHEMBL4142	Kd	6.96	6.96	110.0	1
HOP-62 CHEMBL614643	IC50	6.96	6.96	108.4	1
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	6.85	6.85	140.0	1
Non-receptor tyrosine-protein kinase TNK1 CHEMBL5334	Kd	6.8	6.265	160.0	2
KU812 cell line CHEMBL613997	IC50	6.78	6.78	165.8	1
Vascular endothelial growth factor receptor 3 CHEMBL1955	Kd	6.77	6.77	170.0	1
EM-2 CHEMBL2366281	IC50	6.77	6.77	168.2	1
LAMA-84 CHEMBL2366090	IC50	6.75	6.75	176.7	1
TRAF2 and NCK-interacting protein kinase CHEMBL4527	Kd	6.75	6.25	180.0	2
Breakpoint cluster region protein CHEMBL5146	Kd	6.73	6.73	188.0	1
Fibroblast growth factor receptor 3 CHEMBL2742	Kd	6.68	6.68	210.0	2
JAR CHEMBL614587	IC50	6.62	6.62	239.9	1
Fibroblast growth factor receptor 1 CHEMBL3650	Kd	6.57	6.495	268.0	2
Mitogen-activated protein kinase kinase kinase 19 CHEMBL6191	Kd	6.57	6.57	270.0	1
Angiopoietin-1 receptor CHEMBL4128	Kd	6.51	6.51	310.0	1
G-361 CHEMBL614036	IC50	6.49	6.49	323.2	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1090.0	ng.hr.mL-1	Mus musculus
AUC	1760.0	ng.hr.mL-1	Mus musculus
AUC	950.0	ng.hr.mL-1	Mus musculus
AUC	1400.0	ng.hr.mL-1	Mus musculus
AUC	2680.0	ng.hr.mL-1	Mus musculus
AUC	4670.0	ng.hr.mL-1	Mus musculus
AUC	3950.0	ng.hr.mL-1	Mus musculus
AUC	4950.0	ng.hr.mL-1	Mus musculus
AUC	19067.0	ng.hr.mL-1	Mus musculus
AUC	13813.0	ng.hr.mL-1	Mus musculus
Cmax	60960.46	nM	Mus musculus
Cmax	35681.02	nM	Mus musculus
Cmax	1865.56	nM	Mus musculus
Cmax	9200.99	nM	Mus musculus
Cmax	71.93	nM	Homo sapiens
T1/2	0.8	hr	Mus musculus
T1/2	1.1	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Vascular endothelial growth factor receptor 2	IC50	=	0.02	nM	10.7	Inhibition of VEGFR-2 (unknown origin) expressed in PAE cells assessed as reduct...	37285684
EOL1	IC50	=	0.05132	nM	10.29	SANGER: Inhibition of human EoL-1-cell cell growth in a cell viability assay.	-
Vascular endothelial growth factor receptor 3	IC50	=	0.1	nM	10.0	Inhibition of VEGFR3 (unknown origin)	28844802
Vascular endothelial growth factor receptor 2	IC50	=	0.1	nM	10.0	Inhibition of VEGFR2 (unknown origin)	28844802
Vascular endothelial growth factor receptor 1	IC50	=	0.1	nM	10.0	Inhibition of VEGFR1 (unknown origin)	28844802
Vascular endothelial growth factor receptor 1	IC50	=	0.1	nM	10.0	Inhibition of VEGFR1 (unknown origin)	31306818
Vascular endothelial growth factor receptor 3	IC50	=	0.1	nM	10.0	Inhibition of VEGFR3 (unknown origin)	31306818
Vascular endothelial growth factor receptor 2	IC50	=	0.18	nM	9.74	Inhibition of VEGFR2 (unknown origin)	31306818
Vascular endothelial growth factor receptor 2	IC50	=	0.2	nM	9.7	Inhibition of human VEGFR2	29189002
Tyrosine-protein kinase ABL1	IC50	=	0.2	nM	9.7	Inhibition of active wild type His-tagged ABL T315I mutant (229 to 500 residues)...	30317026
Vascular endothelial growth factor receptor 2	Ki	=	0.2	nM	9.7	In-Vitro Kinase Inhibition Assay: Compounds 2-4 and cabozantinib were each teste...	-
Vascular endothelial growth factor receptor 2	IC50	=	0.25	nM	9.6	Inhibition of recombinant VEGFR2 after 1 hr by fluorescence polarization assay	20869793
Tyrosine-protein kinase ABL1	IC50	=	0.418	nM	9.38	Z′-LYTE Screening Assay: Axitinib was tested using a Z′-LYTE Screening Protocol ...	-
Mast/stem cell growth factor receptor Kit	Kd	=	0.49	nM	9.31	Binding constant for KIT(V559D) kinase domain	22037378
NON-PROTEIN TARGET	IC50	=	0.5	nM	9.3	Antiproliferative activity against VEGF-stimulated HUVEC cells assessed as reduc...	-
Platelet-derived growth factor receptor alpha	Kd	=	0.51	nM	9.29	Binding constant for PDGFRA kinase domain	22037378
Tyrosine-protein kinase ABL1	IC50	=	0.5511	nM	9.26	ABL1 Kinase Mobility-Shift Assay: Axitinib was tested with the Caliper LabChip30...	-
Platelet-derived growth factor receptor beta	Kd	=	0.57	nM	9.24	Binding constant for PDGFRB kinase domain	22037378
Vascular endothelial growth factor receptor 2	IC50	=	0.91	nM	9.04	Kinase Inhibition Assay: Measurement of the kinase inhibitory activity of each c...	-
NCI-H1703	IC50	=	0.9022	nM	9.04	SANGER: Inhibition of human NCI-H1703 cell growth in a cell viability assay.	-

Literature References

PubMed	DOI	Target Context	# Activities
26254279	10.18632/oncotarget.4214	Unchecked	27
21282407	10.1124/dmd.110.037317	ADMET	17
31046271	10.1021/acs.jmedchem.9b00176	Mast/stem cell growth factor receptor Kit	16
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
21282407	10.1124/dmd.110.037317	Brain	14
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
30317026	10.1016/j.ejmech.2018.10.007	Bcr/Abl fusion protein	9
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
21282407	10.1124/dmd.110.037317	Plasma	8
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
30317026	10.1016/j.ejmech.2018.10.007	Tyrosine-protein kinase ABL1	6
22037378	10.1038/nbt.1990	Proto-oncogene tyrosine-protein kinase receptor Ret	4
29191878	10.1126/science.aan4368	Unchecked	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
31445229	10.1016/j.ejmech.2019.111609	Unchecked	4
21282407	10.1124/dmd.110.037317	Broad substrate specificity ATP-binding cassette transporter ABCG2	4
37468498	10.1038/s41467-023-40064-9	Nuclear receptor subfamily 1 group I member 2	3
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	3

Data from ChEMBL 36 via Core Engine