Compound Detail

CHEMBL24828

VANDETANIB

💊 Approved Drug

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💊 Approved Drug

COc1cc2/c(=N/c3ccc(Br)cc3F)nc[nH]c2cc1OCC1CCN(C)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL24828
Name	VANDETANIB
Phase	Approved
Structure Type	MOL
InChI Key	UHTHHESEBZOYNR-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Caprelsa GNF-PF-2188 NSC-744325 NSC-760766 Vandetanib Zactima ZD-64 ZD-6474 ZD6474

133

Targets

543

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

475.4

MW (Da)

4.43

ALogP

HBA

HBD

62.7

PSA (Å²)

0.59

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2011
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning

USAN Stem	-anib
USAN Year	2006

Extended Properties

Molecular Formula	C22H24BrFN4O2
MW	475.36
Aromatic Rings	3
Heavy Atoms	30
NP-Likeness	-0.87

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Tyrosine-protein kinase SRC inhibitor	INHIBITOR	Proto-oncogene tyrosine-protein kinase Src	✓	✓
Tyrosine-protein kinase BRK inhibitor	INHIBITOR	Protein-tyrosine kinase 6	✓	✓
Tyrosine-protein kinase TIE-2 inhibitor	INHIBITOR	Angiopoietin-1 receptor	✓	✓
Vascular endothelial growth factor receptor inhibitor	INHIBITOR	Vascular endothelial growth factor receptor	✓	✓
Tyrosine-protein kinase receptor RET inhibitor	INHIBITOR	Proto-oncogene tyrosine-protein kinase receptor Ret	✓	✓
Ephrin receptor inhibitor	INHIBITOR	Ephrin receptor	✓	✓
Epidermal growth factor receptor inhibitor	INHIBITOR	Epidermal growth factor receptor	✓	✓

Indications

Carcinoma, Medullary Neoplasms Neoplasms Thyroid Neoplasms Thyroid Neoplasms Thyroid Neoplasms Thyroid Neoplasms Carcinoma, Non-Small-Cell Lung Lung Neoplasms Adenocarcinoma, Follicular Astrocytoma Breast Neoplasms Breast Neoplasms Carcinoma, Hepatocellular Carcinoma, Renal Cell Carcinoma, Squamous Cell Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Fallopian Tube Neoplasms

ATC Classification

L01EX04

vandetanib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning

cardiotoxicity

Country: United States

Activity Summary

Kd 326 meas. best 8.34

IC50 190 meas. best 9.96

Ki 23 meas. best 8.2

EC50 4 meas. best 8.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Vascular endothelial growth factor receptor 3 CHEMBL1955	IC50	9.96	8.295	0.1	2
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	9.89	6.5044	0.1	25
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	9.1	7.73	0.8	3
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	8.4	7.1026	4.0	50
Receptor-interacting serine/threonine-protein kinase 2 CHEMBL5014	Kd	8.34	7.83	4.6	4
Epidermal growth factor receptor CHEMBL203	Kd	8.32	7.8424	4.8	25
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	8.2	8.2	6.3	1
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	8.05	7.1123	9.0	30
HUVEC CHEMBL613979	EC50	8.0	7.61	10.0	2
Epidermal growth factor receptor CHEMBL203	IC50	7.96	6.5646	11.0	24
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	7.96	7.2633	11.0	3
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	7.85	7.386	14.0	5
Tyrosine-protein kinase Lck CHEMBL258	Kd	7.77	7.0625	17.0	4
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Ki	7.7	7.7	19.9	1
Coiled-coil domain-containing protein 6/Tyrosine-protein kinase receptor RET CHEMBL3430904	IC50	7.7	7.7	20.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	7.66	6.7067	22.0	9
Vascular endothelial growth factor receptor CHEMBL2095227	IC50	7.6	7.0	25.0	2
Tyrosine-protein kinase ABL1 CHEMBL1862	Ki	7.5	7.5	31.6	1
Protein-tyrosine kinase 6 CHEMBL4601	Kd	7.48	6.7475	33.0	4
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	7.47	6.4638	34.0	16
Tyrosine-protein kinase Lck CHEMBL258	Ki	7.4	7.4	39.8	1
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	7.31	7.31	49.0	1
Ephrin type-A receptor 6 CHEMBL4526	Kd	7.3	7.2633	50.0	3
Serine/threonine-protein kinase 35 CHEMBL5651	Kd	7.25	7.25	56.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	Ki	7.2	7.2	63.1	1
Tyrosine-protein kinase receptor TYRO3 CHEMBL5314	Ki	7.2	7.2	63.1	1
Tyrosine-protein kinase Blk CHEMBL2250	Kd	7.18	7.18	66.0	2
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	Kd	7.16	7.03	70.0	3
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	7.16	7.07	69.0	3
Interleukin-1 receptor-associated kinase 4 CHEMBL3778	Kd	7.12	7.12	75.0	1
Ephrin type-B receptor 6 CHEMBL5836	Kd	7.12	7.12	76.0	1
Serine/threonine-protein kinase 10 CHEMBL3981	Kd	7.09	6.486	81.0	5
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	7.07	6.945	86.0	2
Cyclin-G-associated kinase CHEMBL4355	Kd	7.07	6.9225	86.0	4
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	7.06	6.9067	88.0	3
Ephrin type-A receptor 8 CHEMBL4134	Kd	7.04	6.96	91.0	3
Tyrosine-protein kinase receptor TYRO3 CHEMBL5314	Kd	7.03	7.03	93.0	3
STE20-like serine/threonine-protein kinase CHEMBL4202	Kd	7.02	7.02	95.0	3
Rho-associated protein kinase 2 CHEMBL2973	Ki	7.0	7.0	100.0	1
Tyrosine-protein kinase Lyn CHEMBL3905	Kd	6.96	6.69	110.0	3
TPC1 CHEMBL613836	IC50	6.94	6.94	116.0	1
Tyrosine-protein kinase Yes CHEMBL2073	Kd	6.92	6.7967	120.0	3
Activin receptor type-1 CHEMBL5903	Kd	6.82	6.82	150.0	2
Platelet-derived growth factor receptor alpha CHEMBL2007	Ki	6.8	6.8	158.5	1
Receptor tyrosine-protein kinase erbB-3 CHEMBL5838	Kd	6.8	6.8	160.0	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Ki	6.8	6.8	158.5	1
Tyrosine-protein kinase FRK CHEMBL4223	Kd	6.77	6.545	170.0	4
HUVEC CHEMBL613979	IC50	6.73	5.9	187.0	4
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	6.72	6.0515	190.0	13
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	6.7	6.7	200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
F	50.0	%	Rattus norvegicus
Fu	0.082	-	Rattus norvegicus
T1/2	8.3	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Vascular endothelial growth factor receptor 3	IC50	=	0.11	nM	9.96	Inhibition of VEGFR3 (unknown origin)	34402300
Proto-oncogene tyrosine-protein kinase receptor Ret	IC50	=	0.13	nM	9.89	Inhibition of RET (unknown origin)	34402300
Proto-oncogene tyrosine-protein kinase Src	IC50	=	0.79	nM	9.1	Inhibition of SRC (unknown origin)	33970631
Vascular endothelial growth factor receptor 2	IC50	=	4.0	nM	8.4	Inhibition of recombinant VEGFR2 (unknown origin) incubated for 120 mins by Perk...	34402300
Proto-oncogene tyrosine-protein kinase receptor Ret	IC50	=	4.0	nM	8.4	Measurement of Biochemical Activity of Compounds: In order to assess the activit...	-
Receptor-interacting serine/threonine-protein kinase 2	Kd	=	4.6	nM	8.34	Binding constant for RIPK2 kinase domain	18183025
Receptor-interacting serine/threonine-protein kinase 2	Kd	=	4.6	nM	8.34	Binding constant for RIPK2 kinase domain	22037378
Epidermal growth factor receptor	Kd	=	4.8	nM	8.32	Binding constant for EGFR(E746-A750del) kinase domain	18183025
Epidermal growth factor receptor	Kd	=	4.8	nM	8.32	Binding constant for EGFR(E746-A750del) kinase domain	22037378
Epidermal growth factor receptor	Kd	=	5.9	nM	8.23	Binding constant for EGFR(G719S) kinase domain	18183025
Epidermal growth factor receptor	Kd	=	5.9	nM	8.23	Binding constant for EGFR(G719S) kinase domain	22037378
Vascular endothelial growth factor receptor 2	Ki	=	6.31	nM	8.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Proto-oncogene tyrosine-protein kinase receptor Ret	IC50	=	7.0	nM	8.15	Inhibition of recombinant RET M918T (unknown origin) incubated for 120 mins by P...	34402300
Epidermal growth factor receptor	Kd	=	7.9	nM	8.1	Binding constant for EGFR(L747-S752del, P753S) kinase domain	22037378
Epidermal growth factor receptor	Kd	=	7.9	nM	8.1	Binding constant for EGFR(L747-S752del, P753S) kinase domain	18183025
Epidermal growth factor receptor	Kd	=	8.7	nM	8.06	Binding constant for EGFR(L858R) kinase domain	18183025
Epidermal growth factor receptor	Kd	=	8.7	nM	8.06	Binding constant for EGFR(L858R) kinase domain	22037378
Proto-oncogene tyrosine-protein kinase receptor Ret	IC50	=	9.0	nM	8.05	Inhibition of recombinant human RET using KKKSPGEYVNIEFG as substrate incubated ...	29133048
Tyrosine-protein kinase ABL1	Kd	=	9.0	nM	8.05	Binding constant for ABL1(Y253F)-phosphorylated kinase domain	22037378
Epidermal growth factor receptor	Kd	=	8.9	nM	8.05	Binding constant for EGFR(L747-T751del,Sins) kinase domain	22037378

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4295262	Unchecked	32
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
26254279	10.18632/oncotarget.4214	Unchecked	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
18183025	10.1038/nbt1358	Epidermal growth factor receptor	10
31387063	10.1016/j.ejmech.2019.07.055	A549	9
26254279	10.18632/oncotarget.4214	Proto-oncogene tyrosine-protein kinase receptor Ret	9
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
18183025	10.1038/nbt1358	Tyrosine-protein kinase ABL1	7
15711537	10.1038/nbt1068	Tyrosine-protein kinase ABL1	7
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
18183025	10.1038/nbt1358	Receptor-type tyrosine-protein kinase FLT3	5
18183025	10.1038/nbt1358	Mast/stem cell growth factor receptor Kit	5
16302797	10.1021/jm050559f	Vascular endothelial growth factor receptor 2	5
31387063	10.1016/j.ejmech.2019.07.055	NCI-H446	5
29133048	10.1016/j.ejmech.2017.09.018	BaF3	5
29191878	10.1126/science.aan4368	Unchecked	5
22037378	10.1038/nbt.1990	Proto-oncogene tyrosine-protein kinase receptor Ret	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4

Data from ChEMBL 36 via Core Engine