Compound Detail

CHEMBL502835

NINTEDANIB

💊 Approved Drug

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💊 Approved Drug

COC(=O)c1ccc2c(c1)NC(=O)/C2=C(\Nc1ccc(N(C)C(=O)CN2CCN(C)CC2)cc1)c1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL502835
Name	NINTEDANIB
Phase	Approved
Structure Type	MOL
InChI Key	XZXHXSATPCNXJR-ZIADKAODSA-N
Therapeutic	✓ Yes

Known Names

BIBF 1120 Bibf-1120 BIBF1120 Intedanib Nintedanib Nintedanib component of ofev Ofev Vargatef

237

Targets

438

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

539.6

MW (Da)

3.62

ALogP

HBA

HBD

94.2

PSA (Å²)

0.35

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2014
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product First in Class

USAN Stem	-anib
USAN Year	2012

Extended Properties

Molecular Formula	C31H33N5O4
MW	539.64
Aromatic Rings	3
Heavy Atoms	40
NP-Likeness	-1.13

Indications

Carcinoma, Non-Small-Cell Lung Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Idiopathic Pulmonary Fibrosis Lung Diseases, Interstitial Neoplasms Pulmonary Fibrosis Scleroderma, Systemic Severe Acute Respiratory Syndrome Appendiceal Neoplasms Astrocytoma Breast Neoplasms Bronchiolitis Obliterans Carcinoid Tumor Carcinoma, Hepatocellular Carcinoma, Medullary Carcinoma, Renal Cell Carcinoma, Squamous Cell Endometrial Neoplasms

ATC Classification

L01EX09

nintedanib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

Kd 303 meas. best 9.38

IC50 109 meas. best 8.74

Ki 19 meas. best 8.42

EC50 7 meas. best 8.15

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	9.38	8.6256	0.4	9
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	8.74	8.1089	1.8	9
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	8.74	7.745	1.8	2
Platelet-derived growth factor receptor alpha CHEMBL2007	IC50	8.72	7.8857	1.9	7
Unchecked CHEMBL612545	IC50	8.72	5.7367	1.9	15
BMP-2-inducible protein kinase CHEMBL4522	Kd	8.66	7.12	2.2	2
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	8.59	8.59	2.6	1
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	8.57	7.7488	2.7	8
Vascular endothelial growth factor receptor 2 CHEMBL279	Kd	8.54	8.54	2.9	1
Vascular endothelial growth factor receptor 3 CHEMBL1955	IC50	8.52	8.0933	3.0	6
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	8.52	7.916	3.0	5
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	8.51	8.134	3.1	10
Serine/threonine-protein kinase PknB CHEMBL1908385	Kd	8.44	8.44	3.6	1
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	8.42	8.42	3.8	3
Mitogen-activated protein kinase kinase kinase 7 CHEMBL5776	Kd	8.39	8.39	4.1	1
High affinity nerve growth factor receptor CHEMBL2815	Kd	8.35	6.94	4.5	2
Tyrosine-protein kinase JAK1 CHEMBL2835	Kd	8.32	6.96	4.8	2
Maternal embryonic leucine zipper kinase CHEMBL4578	Kd	8.31	7.795	4.9	2
Mitogen-activated protein kinase kinase kinase 19 CHEMBL6191	Kd	8.28	8.28	5.2	1
Maternal embryonic leucine zipper kinase CHEMBL4578	Ki	8.25	8.25	5.6	1
Fibroblast growth factor receptor 3 CHEMBL2742	Ki	8.23	8.23	5.9	3
Tyrosine-protein kinase Lck CHEMBL258	Kd	8.21	7.685	6.2	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	8.15	7.47	7.0	3
Unchecked CHEMBL612545	EC50	8.15	8.15	7.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	Ki	8.1	8.1	8.0	3
Tyrosine-protein kinase JAK3 CHEMBL2148	Kd	8.09	8.09	8.2	1
Serine/threonine-protein kinase PRP4 homolog CHEMBL1908382	Kd	8.08	8.08	8.4	1
Platelet-derived growth factor receptor alpha CHEMBL2007	Ki	8.08	8.08	8.4	3
Tyrosine-protein kinase Mer CHEMBL5331	Kd	8.07	8.07	8.5	1
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	8.06	8.06	8.8	1
Serine/threonine-protein kinase 4 CHEMBL4598	Kd	8.05	7.41	9.0	2
HUVEC CHEMBL613979	EC50	8.05	7.295	9.0	2
Mitogen-activated protein kinase kinase kinase 2 CHEMBL5914	Kd	8.03	6.925	9.4	2
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	8.0	6.8169	10.0	16
Dual specificity mitogen-activated protein kinase kinase 1 CHEMBL3587	Kd	8.0	8.0	10.0	1
HUVEC CHEMBL613979	IC50	8.0	8.0	10.0	1
Tyrosine-protein kinase receptor UFO CHEMBL4895	Kd	7.92	7.92	12.0	1
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	7.92	7.81	12.0	2
SRSF protein kinase 3 CHEMBL5415	Kd	7.92	7.92	12.0	1
Vascular endothelial growth factor receptor 1 CHEMBL1868	IC50	7.89	7.5833	13.0	6
Vascular endothelial growth factor receptor 2 CHEMBL3337	IC50	7.89	7.89	13.0	1
Tyrosine-protein kinase JAK2 CHEMBL2971	Kd	7.85	7.415	14.0	2
cGMP-dependent protein kinase 1 CHEMBL4273	Kd	7.85	7.85	14.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	7.82	7.665	15.0	2
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	7.8	7.8	16.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	7.8	7.8	16.0	2
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	7.8	7.14	16.0	3
Discoidin domain-containing receptor 2 CHEMBL5122	Kd	7.8	7.59	16.0	2
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta CHEMBL5667	Kd	7.77	7.77	17.0	1
G protein-coupled receptor kinase 4 CHEMBL5861	Kd	7.77	7.77	17.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2746.0	nM	Mus musculus
CL	173.0	mL.min-1.kg-1	Mus musculus
CL	63.5	mL.min-1.kg-1	Homo sapiens
Cmax	1091.0	nM	Mus musculus
F	45.0	%	Mus musculus
F	12.0	%	Rattus norvegicus
F	12.0	%	Rattus norvegicus
F	4.7	%	Homo sapiens
T1/2	5.0	hr	Mus musculus
T1/2	0.4563	hr	Homo sapiens
Vd	32.0	L.kg-1	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Receptor-type tyrosine-protein kinase FLT3	Kd	=	0.42	nM	9.38	Binding constant for FLT3(D835Y) kinase domain	22037378
Receptor-type tyrosine-protein kinase FLT3	Kd	=	0.71	nM	9.15	Binding constant for FLT3(D835H) kinase domain	22037378
Receptor-type tyrosine-protein kinase FLT3	Kd	=	0.7	nM	9.15	Binding constant for FLT3(ITD) kinase domain	22037378
Dual specificity mitogen-activated protein kinase kinase 5	Kd	=	1.8	nM	8.74	Binding constant for MEK5 kinase domain	22037378
Platelet-derived growth factor receptor beta	IC50	=	1.8	nM	8.74	Inhibition of recombinant PDGFRbeta (unknown origin) by off-chip mobility shift ...	29152045
Platelet-derived growth factor receptor beta	IC50	=	1.8	nM	8.74	Inhibition of PDGFRbeta (unknown origin) by enzymatic assay	37683364
Platelet-derived growth factor receptor alpha	IC50	=	1.9	nM	8.72	Inhibition of PDGFRalpha (unknown origin) preincubated for 10 mins followed by F...	28190652
Unchecked	IC50	=	1.9	nM	8.72	Inhibition of N-terminal GST-tagged human recombinant PDGFRalpha D842I mutant ex...	32305182
Platelet-derived growth factor receptor beta	IC50	=	2.0	nM	8.7	Inhibition of PDGFRbeta (unknown origin) using poly (Glu, Tyr)4:1 as substrate b...	23770449
BMP-2-inducible protein kinase	Kd	=	2.2	nM	8.66	Binding constant for BIKE kinase domain	22037378
Platelet-derived growth factor receptor alpha	IC50	=	2.3	nM	8.64	Inhibition of N-terminal GST tagged human PDGFRalpha (550 to 1089 end residues) ...	28826084
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	2.6	nM	8.59	Inhibition of human ERG	29152045
Receptor-type tyrosine-protein kinase FLT3	Kd	=	2.6	nM	8.59	Binding constant for FLT3(N841I) kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	2.7	nM	8.57	Binding constant for KIT(L576P) kinase domain	22037378
Vascular endothelial growth factor receptor 2	Kd	=	2.9	nM	8.54	Binding constant for VEGFR2 kinase domain	22037378
Mast/stem cell growth factor receptor Kit	Kd	=	2.9	nM	8.54	Binding constant for KIT(V559D,T670I) kinase domain	22037378
Proto-oncogene tyrosine-protein kinase receptor Ret	Kd	=	3.0	nM	8.52	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Unchecked	IC50	=	3.0	nM	8.52	Inhibition of GST-tagged human recombinant VEGFR3 cytoplasmic domain (800 to 129...	32305182
Vascular endothelial growth factor receptor 3	IC50	=	3.0	nM	8.52	Inhibition of recombinant human GST-tagged VEGFR3 cytoplasmic domain expressed i...	28190652
Vascular endothelial growth factor receptor 2	IC50	=	3.1	nM	8.51	Inhibition of VEGFR2 (unknown origin)	37683364

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724801	U2OS	320
-	10.6019/CHEMBL5724801	Fibroblast	320
-	10.6019/CHEMBL5724801	HEK-293T	320
26254279	10.18632/oncotarget.4214	Unchecked	19
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
18559524	10.1158/0008-5472.can-07-6307	FaDu	12
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
18559524	10.1158/0008-5472.can-07-6307	Unchecked	11
31699535	10.1016/j.ejmech.2019.111790	Mus musculus	10
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
37826934	10.1016/j.ejmech.2023.115856	Mus musculus	9
26254279	10.18632/oncotarget.4214	Fibroblast growth factor receptor	8
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
19522465	10.1021/jm900431g	Mus musculus	8
18559524	10.1158/0008-5472.can-07-6307	NON-PROTEIN TARGET	8
18559524	10.1158/0008-5472.can-07-6307	RAC-alpha serine/threonine-protein kinase	8
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
31866272	10.1016/j.bmc.2019.115254	Mus musculus	7
19522465	10.1021/jm900431g	FaDu	6
32334267	10.1016/j.ejmech.2020.112259	Mus musculus	6

Data from ChEMBL 36 via Core Engine