Compound Detail

CHEMBL535

SUNITINIB

💊 Approved Drug

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💊 Approved Drug

CCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3ccc(F)cc32)c1C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL535
Name	SUNITINIB
Phase	Approved
Structure Type	MOL
InChI Key	WINHZLLDWRZWRT-ATVHPVEESA-N
Therapeutic	✓ Yes

Known Names

NSC-736511 NSC-750690 SU-011248 SU-11248 SU011248 Sunitinib Sunitinib accord

603

Targets

1,915

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

398.5

MW (Da)

3.33

ALogP

HBA

HBD

77.2

PSA (Å²)

0.63

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2006
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning

USAN Stem

-tinib

Extended Properties

Molecular Formula	C22H27FN4O2
MW	398.48
Aromatic Rings	2
Heavy Atoms	29
NP-Likeness	-1.21

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Macrophage colony stimulating factor receptor inhibitor	INHIBITOR	Macrophage colony-stimulating factor 1 receptor	✓	✓
Vascular endothelial growth factor receptor 2 inhibitor	INHIBITOR	Vascular endothelial growth factor receptor 2	✓	✓
Stem cell growth factor receptor inhibitor	INHIBITOR	Mast/stem cell growth factor receptor Kit	✓	✓
Platelet-derived growth factor receptor beta inhibitor	INHIBITOR	Platelet-derived growth factor receptor beta	✓	✓
Platelet-derived growth factor receptor alpha inhibitor	INHIBITOR	Platelet-derived growth factor receptor alpha	✓	✓
Vascular endothelial growth factor receptor 1 inhibitor	INHIBITOR	Vascular endothelial growth factor receptor 1	✓	✓
Vascular endothelial growth factor receptor 3 inhibitor	INHIBITOR	Vascular endothelial growth factor receptor 3	✓	✓
Tyrosine-protein kinase receptor FLT3 inhibitor	INHIBITOR	Receptor-type tyrosine-protein kinase FLT3	✓	✓
Tyrosine-protein kinase receptor RET inhibitor	INHIBITOR	Proto-oncogene tyrosine-protein kinase receptor Ret	✓	✓

Indications

Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Carcinoma, Renal Cell Gastrointestinal Stromal Tumors Neoplasms Neoplasms Neuroendocrine Tumors Neuroendocrine Tumors Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Kidney Neoplasms Kidney Neoplasms Prostatic Neoplasms Prostatic Neoplasms Urogenital Neoplasms Adenocarcinoma Adrenal Cortex Neoplasms Ascites

ATC Classification

L01EX01

sunitinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

Kd 977 meas. best 10.12

IC50 891 meas. best 9.56

EC50 33 meas. best 7.84

Ki 14 meas. best 8.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	10.12	9.69	0.1	6
Vascular endothelial growth factor receptor 2 CHEMBL279	Kd	9.7	8.8867	0.2	6
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	9.68	8.6713	0.2	23
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	9.66	8.9008	0.2	25
MV4-11 CHEMBL613835	IC50	9.56	7.97	0.3	12
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	9.4	7.1458	0.4	59
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	9.15	7.1796	0.7	28
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	9.15	7.465	0.7	36
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	9.1	9.1	0.8	3
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	9.0	7.9533	1.0	3
Serine/threonine-protein kinase 17A CHEMBL4525	Kd	9.0	8.472	1.0	5
Unchecked CHEMBL612545	Kd	9.0	6.81	1.0	4
Chorioallantoic membrane CHEMBL2367390	IC50	8.89	6.64	1.3	4
Unchecked CHEMBL612545	IC50	8.85	6.552	1.4	25
Vascular endothelial growth factor receptor 1 CHEMBL1868	Kd	8.74	8.74	1.8	3
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Kd	8.7	8.6667	2.0	3
Vascular endothelial growth factor receptor 1 CHEMBL1868	Ki	8.7	8.7	2.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	8.7	6.5513	2.0	15
BaF3 CHEMBL614524	IC50	8.64	6.2336	2.3	11
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	8.54	8.148	2.9	5
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.52	5.4789	3.0	44
Mast/stem cell growth factor receptor Kit CHEMBL1936	Ki	8.4	8.4	4.0	1
Macrophage colony-stimulating factor 1 receptor CHEMBL5570	IC50	8.39	8.39	4.1	1
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	IC50	8.3	6.6118	5.0	11
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	8.3	6.3773	5.0	11
Phosphorylase b kinase gamma catalytic chain, skeletal muscle/heart isoform CHEMBL4004	Kd	8.26	7.82	5.5	5
BMP-2-inducible protein kinase CHEMBL4522	Kd	8.26	7.78	5.5	6
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	8.24	7.9064	5.8	11
Phosphorylase b kinase gamma catalytic chain, liver/testis isoform CHEMBL2349	Kd	8.23	7.615	5.9	6
MDA-MB-468 CHEMBL614335	IC50	8.21	8.21	6.1	1
Protein delta homolog 1 CHEMBL5671	Ki	8.2	8.2	6.3	2
Platelet-derived growth factor receptor alpha CHEMBL2007	IC50	8.16	7.3825	6.9	4
Serine/threonine-protein kinase Chk2 CHEMBL2527	Kd	8.15	8.075	7.1	2
HUVEC CHEMBL613979	IC50	8.15	5.9395	7.0	21
Platelet-derived growth factor receptor beta CHEMBL1913	Ki	8.1	8.1	8.0	1
Platelet-derived growth factor receptor CHEMBL2096980	IC50	8.1	7.82	8.0	4
Vascular endothelial growth factor receptor 3 CHEMBL1955	IC50	8.05	7.835	8.9	2
Tyrosine-protein kinase Lck CHEMBL258	IC50	8.05	8.05	8.9	1
Tyrosine-protein kinase JAK1 CHEMBL2835	Kd	8.05	6.8475	9.0	8
Tyrosine-protein kinase receptor UFO CHEMBL4895	IC50	8.05	8.05	9.0	2
Tyrosine-protein kinase receptor UFO CHEMBL4895	Kd	8.05	8.05	9.0	3
MDA-MB-435 CHEMBL614697	IC50	8.01	6.52	9.7	2
AP2-associated protein kinase 1 CHEMBL3830	Kd	7.96	7.6791	11.0	11
Tyrosine-protein kinase ITK/TSK CHEMBL2959	Kd	7.89	7.89	13.0	3
Casein kinase I isoform epsilon CHEMBL4937	Kd	7.89	7.435	13.0	4
Serine/threonine-protein kinase ULK2 CHEMBL5435	Kd	7.89	7.89	13.0	2
Interleukin-1 receptor-associated kinase 1 CHEMBL3357	Kd	7.85	7.85	14.0	2
OCI-AML-5 CHEMBL4523576	IC50	7.85	7.85	14.0	1
MOLM-13 CHEMBL3706572	EC50	7.84	7.84	14.3	1
Leucine-rich repeat serine/threonine-protein kinase 2 CHEMBL1075104	IC50	7.82	7.4763	15.0	8

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	438.33	ng.hr.mL-1	Mus musculus
AUC	7202.0	ng.hr.mL-1	Rattus norvegicus
AUC	23994.0	ng.hr.mL-1	Rattus norvegicus
AUC	11848.0	ng.hr.mL-1	Rattus norvegicus
AUC	1063.0	ng.hr.mL-1	Homo sapiens
AUC	1099.0	ng.hr.mL-1	Macaca fascicularis
AUC	1453.0	ng.hr.mL-1	Macaca fascicularis
CL	13.0	mL.min-1.kg-1	Rattus norvegicus
CL	21.0	mL.min-1.g-1	Homo sapiens
CL	58.0	mL.min-1.g-1	Mus musculus
Cmax	320.0	nM	Mus musculus
Cmax	4574.88	nM	Rattus norvegicus
Cmax	3144.45	nM	Rattus norvegicus
Cmax	2416.68	nM	Rattus norvegicus
Cmax	61.23	nM	Homo sapiens
Cmax	208.29	nM	Macaca fascicularis
Cmax	230.88	nM	Macaca fascicularis
Fu	0.007	-	Rattus norvegicus
Fu	0.009	-	Rattus norvegicus
T1/2	0.08333	hr	Homo sapiens
T1/2	0.08333	hr	Homo sapiens
T1/2	0.08333	hr	Homo sapiens
T1/2	0.08333	hr	Homo sapiens
T1/2	0.1833	hr	Mus musculus
T1/2	0.5	hr	Homo sapiens
T1/2	0.1883	hr	Homo sapiens
T1/2	0.735	hr	Homo sapiens
T1/2	0.205	hr	Mus musculus
T1/2	0.4417	hr	Rattus norvegicus
T1/2	7.4	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Platelet-derived growth factor receptor beta	Kd	=	0.075	nM	10.12	Binding constant for PDGFRB kinase domain	18183025
Platelet-derived growth factor receptor beta	Kd	=	0.075	nM	10.12	Binding affinity to PDGFRB	19654408
Platelet-derived growth factor receptor beta	Kd	=	0.075	nM	10.12	Binding constant for PDGFRB kinase domain	22037378
Vascular endothelial growth factor receptor 2	Kd	=	0.2	nM	9.7	Inhibition of KDR by cellular assay	18077425
Platelet-derived growth factor receptor beta	Kd	=	0.2	nM	9.7	Inhibition of PDGFRbeta by cellular assay	18077425
Platelet-derived growth factor receptor beta	Kd	=	0.21	nM	9.68	Average Binding Constant for PDGFRB; NA=Not Active at 10 uM	15711537
Mast/stem cell growth factor receptor Kit	Kd	=	0.21	nM	9.68	Binding constant for KIT(V559D,V654A) kinase domain	18183025
Mast/stem cell growth factor receptor Kit	Kd	=	0.21	nM	9.68	Binding affinity to KIT V559D,V654A mutant	19654408
Mast/stem cell growth factor receptor Kit	Kd	=	0.21	nM	9.68	Binding constant for KIT(V559D,V654A) kinase domain	22037378
Receptor-type tyrosine-protein kinase FLT3	Kd	=	0.22	nM	9.66	Binding affinity to FLT3 K663Q mutant	19654408
Receptor-type tyrosine-protein kinase FLT3	Kd	=	0.22	nM	9.66	Binding constant for FLT3(K663Q) kinase domain	22037378
Vascular endothelial growth factor receptor 2	Kd	=	0.23	nM	9.64	Average Binding Constant for VEGFR2; NA=Not Active at 10 uM	15711537
MV4-11	IC50	=	0.2722	nM	9.56	SANGER: Inhibition of human MV-4-11 cell growth in a cell viability assay.	-
Mast/stem cell growth factor receptor Kit	Kd	=	0.28	nM	9.55	Binding constant for KIT(V559D,T670I) kinase domain	18183025
Mast/stem cell growth factor receptor Kit	Kd	=	0.28	nM	9.55	Binding affinity to KIT V559D,T670I mutant	19654408
Mast/stem cell growth factor receptor Kit	Kd	=	0.28	nM	9.55	Binding constant for KIT(V559D,T670I) kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	0.37	nM	9.43	Binding affinity to human KIT incubated for 1 hr by kinase binding assay	21429632
Mast/stem cell growth factor receptor Kit	Kd	=	0.37	nM	9.43	Binding constant for KIT kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	0.37	nM	9.43	Binding affinity to KIT	19654408
Mast/stem cell growth factor receptor Kit	Kd	=	0.37	nM	9.43	Binding constant for KIT kinase domain	18183025

Literature References

PubMed	DOI	Target Context	# Activities
18077425	10.1073/pnas.0707498104	NON-PROTEIN TARGET	210
31250638	10.1021/acs.jmedchem.9b00280	Mast/stem cell growth factor receptor Kit	49
33797247	10.1021/acs.jmedchem.0c02247	MOLM-13	40
30968693	10.1021/acs.jmedchem.8b01845	Mast/stem cell growth factor receptor Kit	29
31721578	10.1021/acs.jmedchem.9b01229	Mast/stem cell growth factor receptor Kit	27
33797247	10.1021/acs.jmedchem.0c02247	MV4-11	26
26254279	10.18632/oncotarget.4214	Unchecked	18
30204441	10.1021/acs.jmedchem.8b00938	Mast/stem cell growth factor receptor Kit	16
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18077425	10.1073/pnas.0707498104	COLO	14
21885287	10.1016/j.bmc.2011.08.002	Vascular endothelial growth factor receptor 2	14
31250638	10.1021/acs.jmedchem.9b00280	Unchecked	13
22180047	10.1124/dmd.111.042853	Rattus norvegicus	13
19740074	10.1042/bj20091035	Leucine-rich repeat serine/threonine-protein kinase 2	12
30742435	10.1021/acs.jmedchem.8b01714	Receptor-type tyrosine-protein kinase FLT3	12
22180047	10.1124/dmd.111.042853	ADMET	12
26629594	10.1021/acs.jmedchem.5b01582	BaF3	12
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

Data from ChEMBL 36 via Core Engine