Compound Detail

CHEMBL255863

NILOTINIB

💊 Approved Drug

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💊 Approved Drug

Cc1cn(-c2cc(NC(=O)c3ccc(C)c(Nc4nccc(-c5cccnc5)n4)c3)cc(C(F)(F)F)c2)cn1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL255863
Name	NILOTINIB
Phase	Approved
Structure Type	MOL
InChI Key	HHZIURLSWUIHRB-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

AMN 107 AMN-107 AMN107 Nilotinib NSC-747599

421

Targets

944

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

529.5

MW (Da)

6.36

ALogP

HBA

HBD

97.6

PSA (Å²)

0.27

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2007
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning First in Class

USAN Stem	-tinib
USAN Year	2006

Extended Properties

Molecular Formula	C28H22F3N7O
MW	529.53
Aromatic Rings	5
Heavy Atoms	39
NP-Likeness	-1.94

Indications

Alzheimer Disease Gastrointestinal Stromal Tumors Leukemia Leukemia, Myelogenous, Chronic, BCR-ABL Positive Leukemia, Myeloid Neoplasms Neoplasms Sarcoma Cerebellar Ataxia Glioma Graft vs Host Disease Hypertension, Pulmonary Leukemia, Myeloid, Acute Melanoma Melanoma Melanoma Neuroma, Acoustic Paraganglioma Parkinson Disease Precursor Cell Lymphoblastic Leukemia-Lymphoma

ATC Classification

L01EA03

nilotinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 825 meas. best 9.84

Kd 103 meas. best 8.96

Ki 13 meas. best 8.39

EC50 3 meas. best 7.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
EOL1 CHEMBL614489	IC50	9.84	9.84	0.1	1
Bcr/Abl fusion protein CHEMBL2096618	IC50	9.48	7.614	0.3	15
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	9.06	7.4702	0.9	52
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	8.96	7.95	1.1	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.81	6.7762	1.5	39
K562 CHEMBL385	IC50	8.74	6.998	1.8	10
KU812 cell line CHEMBL613997	IC50	8.74	8.45	1.8	3
Discoidin domain-containing receptor 2 CHEMBL5122	IC50	8.7	7.794	2.0	5
BaF3 CHEMBL614524	IC50	8.68	7.2406	2.1	17
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	8.44	7.7018	3.6	17
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	IC50	8.43	7.7633	3.7	3
Carbonic anhydrase 2 CHEMBL205	Ki	8.39	8.39	4.1	1
EM-2 CHEMBL2366281	IC50	8.39	8.39	4.1	1
LAMA-84 CHEMBL2366090	IC50	8.31	8.31	4.9	1
Discoidin domain-containing receptor 2 CHEMBL5122	Kd	8.22	7.498	6.0	5
Unchecked CHEMBL612545	IC50	8.15	6.9476	7.0	45
MEG-01 CHEMBL2366084	IC50	8.08	8.08	8.3	1
BCR/ABL1 CHEMBL4523652	IC50	8.0	7.945	10.0	2
BV-173 CHEMBL2366145	IC50	7.96	7.96	10.9	1
Mitogen-activated protein kinase kinase kinase 20 CHEMBL3886	Kd	7.96	6.97	11.0	2
KBM5 CHEMBL4483250	IC50	7.92	6.77	12.0	2
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	7.83	7.0225	14.7	4
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	7.8	7.47	16.0	2
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	7.77	7.0478	17.0	9
Integrin-linked protein kinase CHEMBL5247	Kd	7.7	7.7	20.0	1
Kasumi 1 CHEMBL613988	IC50	7.62	7.62	24.1	1
Platelet-derived growth factor receptor beta CHEMBL1913	IC50	7.6	7.3233	25.0	3
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	7.58	7.06	26.0	2
Carbonic anhydrase 1 CHEMBL261	Ki	7.53	7.53	29.3	1
Mitogen-activated protein kinase 11 CHEMBL3961	Kd	7.44	6.435	36.0	2
Ephrin type-A receptor 8 CHEMBL4134	Kd	7.43	7.43	37.0	1
Carbonic anhydrase 9 CHEMBL3594	Ki	7.38	7.38	41.9	1
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Kd	7.35	7.35	45.0	1
Tyrosine-protein kinase Lck CHEMBL258	Kd	7.33	7.33	47.0	1
Platelet-derived growth factor receptor alpha CHEMBL2007	IC50	7.15	7.15	71.0	1
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	7.13	6.94	74.0	2
SARS-CoV-2 CHEMBL4303835	EC50	7.1	7.1	80.0	1
Carbonic anhydrase 15 CHEMBL5973	Ki	7.1	7.1	79.0	1
Tyrosine-protein kinase FRK CHEMBL4223	Kd	7.07	6.66	86.0	2
Carbonic anhydrase 7 CHEMBL2326	Ki	7.0	7.0	99.0	1
Tyrosine-protein kinase Lyn CHEMBL3905	Kd	7.0	6.395	100.0	2
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.97	6.97	108.2	1
Ephrin type-A receptor 3 CHEMBL4954	Kd	6.96	6.96	110.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.9	5.8167	125.9	3
HEK293 CHEMBL614818	IC50	6.89	5.794	128.0	5
NB7 CHEMBL2366345	IC50	6.87	6.87	134.4	1
Molecular identity unknown CHEMBL612546	IC50	6.73	6.73	188.0	1
Dual specificity mitogen-activated protein kinase kinase 5 CHEMBL4948	Kd	6.72	6.72	190.0	1
Carbonic anhydrase 14 CHEMBL3510	Ki	6.65	6.65	223.0	1
Ephrin type-A receptor 2 CHEMBL2068	Kd	6.64	6.375	230.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	10527.5	ng.hr.mL-1	Mus musculus
AUC	-	-	Homo sapiens
AUC	11.9	ng.hr.mL-1	Mus musculus
Cmax	8326.25	nM	Mus musculus
Cmax	3104.64	nM	Homo sapiens
F	27.1	%	Rattus norvegicus
F	25.0	%	Mus musculus
T1/2	0.1315	hr	Mus musculus
T1/2	0.1315	hr	Homo sapiens
T1/2	1.8	hr	Mus musculus
T1/2	17.0	hr	Homo sapiens
T1/2	13.0	hr	Mus musculus
T1/2	6.483	hr	Homo sapiens
T1/2	3.0	hr	Homo sapiens
t1/2	-	-	Homo sapiens
Tmax	1.0	hr	Mus musculus
Tmax	3.0	hr	Homo sapiens
Vd	0.55	L.kg-1	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
EOL1	IC50	=	0.1445	nM	9.84	SANGER: Inhibition of human EoL-1-cell cell growth in a cell viability assay.	-
Bcr/Abl fusion protein	IC50	=	0.33	nM	9.48	Inhibition of Bcr-Abl kinase (unknown origin) after 30 mins by HTRF assay	23538233
Tyrosine-protein kinase ABL1	IC50	=	0.87	nM	9.06	Inhibition of human N-terminal his tagged unphosphorylated native ABL1 (229 to 4...	21481795
Bcr/Abl fusion protein	IC50	=	1.0	nM	9.0	Inhibition of BCR-ABL (unknown origin)	35551036
Epithelial discoidin domain-containing receptor 1	Kd	=	1.1	nM	8.96	Binding constant for DDR1 kinase domain	22037378
Tyrosine-protein kinase ABL1	IC50	=	1.1	nM	8.96	Inhibition of human ABL1 H396P mutant (229 to 499 residues) using ABLtide as sub...	21481795
Tyrosine-protein kinase ABL1	IC50	=	1.2	nM	8.92	Inhibition of recombinant human N-terminal His-tagged Abl (2 to 1130 residues) e...	32051094
NON-PROTEIN TARGET	IC50	=	1.54	nM	8.81	Antiproliferative activity against mouse BA/F3 cells expressing Bcr-Abl M244V mu...	23088644
KU812 cell line	IC50	=	1.8	nM	8.74	Cytotoxicity against human KU812 cells assessed as inhibition of cell growth mea...	34011155
K562	IC50	=	1.8	nM	8.74	Cytotoxicity against human K562 cells assessed as cell growth inhibition measure...	34011155
Discoidin domain-containing receptor 2	IC50	=	2.0	nM	8.7	Inhibition of wild type DDR2 (unknown origin) preincubated for 30 mins before su...	24754677
BaF3	IC50	=	2.1	nM	8.68	Antiproliferative activity against native mouse BaF3 cells assessed as inhibitio...	21481795
Tyrosine-protein kinase ABL1	IC50	=	2.2	nM	8.66	Inhibition of human N-terminal his tagged phosphorylated native ABL1 (229 to 499...	21481795
KU812 cell line	IC50	=	2.477	nM	8.61	SANGER: Inhibition of human KU812 cell growth in a cell viability assay.	-
NON-PROTEIN TARGET	IC50	=	3.0	nM	8.52	Cytotoxicity against mouse BA/F3 cells expressing BCR-ABL M351T mutant assessed ...	23301703
NON-PROTEIN TARGET	IC50	=	3.4	nM	8.47	Antiproliferative activity against human KU812 cells	21376587
Tyrosine-protein kinase ABL1	Kd	=	3.6	nM	8.44	Binding affinity to human ABL1	23273517
Epithelial discoidin domain-containing receptor 1	IC50	=	3.7	nM	8.43	Inhibition of autophosphorylation of DDR1 expressed in HEK293 cells by ELISA	20817538
K562	IC50	=	3.9	nM	8.41	Cytotoxicity against human K562 cells assessed as cell viability after 72 hrs by...	26814890
Carbonic anhydrase 2	Ki	=	4.1	nM	8.39	Inhibition of human carbonic anhydrase 2 by stopped flow CO2 hydration assay	19527930

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	HEK-293T	345
-	10.6019/CHEMBL4689842	U2OS	343
-	10.6019/CHEMBL4689842	Fibroblast	343
15930265	10.1158/0008-5472.can-05-0259	Unchecked	97
15930265	10.1158/0008-5472.can-05-0259	Tyrosine-protein kinase ABL1	49
15930265	10.1158/0008-5472.can-05-0259	BaF3	37
34583507	10.1021/acs.jmedchem.1c01022	Mus musculus	33
36094045	10.1021/acs.jmedchem.2c00671	Unchecked	21
23301703	10.1021/jm301581y	NON-PROTEIN TARGET	16
23088644	10.1021/jm301188x	NON-PROTEIN TARGET	16
21481795	10.1016/j.ccr.2011.03.003	BaF3	16
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
23301703	10.1021/jm301581y	Tyrosine-protein kinase ABL1	11
34583507	10.1021/acs.jmedchem.1c01022	Unchecked	11
21481795	10.1016/j.ccr.2011.03.003	Tyrosine-protein kinase ABL1	11
31923860	10.1016/j.ejmech.2019.112029	ADMET	10
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
30137981	10.1021/acs.jmedchem.8b01040	Bcr/Abl fusion protein	10
31699612	10.1016/j.bmcl.2019.126758	Bcr/Abl fusion protein	9

Data from ChEMBL 36 via Core Engine