Compound Detail

CHEMBL2403108

CERITINIB

💊 Approved Drug

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💊 Approved Drug

Cc1cc(Nc2ncc(Cl)c(Nc3ccccc3S(=O)(=O)C(C)C)n2)c(OC(C)C)cc1C1CCNCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2403108
Name	CERITINIB
Phase	Approved
Structure Type	MOL
InChI Key	VERWOWGGCGHDQE-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Ceritinib Ceritinib[mi] LDK-378 LDK378 NVP-LDK-378-NX NVP-LDK378-NX Zykadia

Targets

368

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

558.1

MW (Da)

6.36

ALogP

HBA

HBD

105.2

PSA (Å²)

0.28

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

USAN Stem	-tinib
USAN Year	2013

Extended Properties

Molecular Formula	C28H36ClN5O3S
MW	558.15
Aromatic Rings	3
Heavy Atoms	38
NP-Likeness	-1.18

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
ALK tyrosine kinase receptor inhibitor	INHIBITOR	ALK tyrosine kinase receptor	✓	✓
EML4-ALK inhibitor	INHIBITOR	EML4-ALK	✓	✓
NPM/ALK (Nucleophosmin/ALK tyrosine kinase receptor) inhibitor	INHIBITOR	NPM/ALK (Nucleophosmin/ALK tyrosine kinase receptor)	✓	✓

Indications

Carcinoma, Non-Small-Cell Lung Neoplasms Neoplasms Sarcoma Cholangiocarcinoma Glioblastoma Granuloma, Plasma Cell Lymphoma, Large-Cell, Anaplastic Melanoma Melanoma Neuroblastoma Thyroid Neoplasms Liver Diseases

ATC Classification

L01ED02

ceritinib

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 322 meas. best 9.7

EC50 23 meas. best 7.82

Kd 16 meas. best 8.89

Ki 7 meas. best 9.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
ALK tyrosine kinase receptor CHEMBL4247	IC50	9.7	7.9705	0.2	77
Proto-oncogene tyrosine-protein kinase ROS CHEMBL5568	Ki	9.4	8.3967	0.4	6
Unchecked CHEMBL612545	IC50	9.2	6.5587	0.6	23
ALK tyrosine kinase receptor CHEMBL4247	Kd	8.89	8.89	1.3	1
Proto-oncogene tyrosine-protein kinase ROS CHEMBL5568	IC50	8.7	8.2513	2.0	8
SR CHEMBL614300	IC50	8.66	8.66	2.2	1
Insulin receptor CHEMBL1981	IC50	8.15	7.16	7.0	5
BaF3 CHEMBL614524	IC50	8.15	6.6215	7.1	13
Insulin-like growth factor 1 receptor CHEMBL1957	IC50	8.1	7.245	8.0	2
KARPAS-299 CHEMBL2366156	IC50	7.89	7.5018	13.0	17
NCI-H2228 CHEMBL1075536	IC50	7.82	6.8171	15.0	21
SU-DHL-1 CHEMBL2366200	IC50	7.82	7.365	15.0	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.82	6.9378	15.0	9
EML4-ALK CHEMBL3883330	IC50	7.8	6.9208	16.0	26
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.75	7.35	18.0	4
NCI-H3122 CHEMBL4296475	IC50	7.75	7.0489	18.0	9
Epidermal growth factor receptor CHEMBL203	IC50	7.72	6.7475	19.0	4
Testis-specific serine/threonine-protein kinase 1 CHEMBL6003	IC50	7.64	7.64	23.0	1
NPM/ALK (Nucleophosmin/ALK tyrosine kinase receptor) CHEMBL2111387	IC50	7.58	7.58	26.0	1
EML4-ALK CHEMBL3883330	EC50	7.58	6.55	26.0	3
Non-receptor tyrosine-protein kinase TNK1 CHEMBL5334	Kd	7.57	7.57	27.0	1
Activated CDC42 kinase 1 CHEMBL4599	IC50	7.47	7.47	33.6	1
HCC78 CHEMBL4296421	IC50	7.41	7.0357	39.0	7
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	IC50	7.22	6.5933	60.0	3
H-2 class II histocompatibility antigen gamma chain/Proto-oncogene tyrosine-protein kinase ROS CHEMBL6066844	IC50	7.15	6.81	71.0	2
A549 CHEMBL392	IC50	7.09	5.9155	81.0	11
ATP-dependent translocase ABCB1 CHEMBL4302	EC50	7.05	7.05	89.0	1
SH-SY5Y CHEMBL614910	EC50	6.73	6.73	186.0	1
Tyrosine-protein kinase Fer CHEMBL3982	Kd	6.67	6.67	214.0	1
Focal adhesion kinase 1 CHEMBL2695	Kd	6.66	6.66	218.0	1
Fibroblast growth factor receptor 2 CHEMBL4142	IC50	6.58	6.58	260.0	1
Hepatocyte growth factor receptor CHEMBL3717	IC50	6.57	5.98	271.0	3
SK-N-SH CHEMBL614924	EC50	6.52	6.52	303.0	1
SK-N-FI CHEMBL2366120	EC50	6.46	6.46	349.0	1
SH-SY5Y CHEMBL614910	IC50	6.43	6.43	370.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	6.4	6.02	400.0	2
Fibroblast growth factor receptor 3 CHEMBL2742	IC50	6.37	6.37	430.0	1
Raji CHEMBL614628	IC50	6.31	6.31	490.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.25	6.21	560.0	2
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	6.21	5.94	610.0	2
Calcium/calmodulin-dependent protein kinase type IV CHEMBL2494	Kd	6.2	6.2	635.0	1
HT-29 CHEMBL384	IC50	6.16	6.0333	700.0	3
KM12 CHEMBL614709	IC50	6.14	6.14	728.0	1
PC-3 CHEMBL390	IC50	6.12	6.0467	760.0	3
HepG2 CHEMBL395	IC50	6.11	5.75	770.0	2
Tyrosine-protein kinase Lyn CHEMBL3905	IC50	6.08	5.86	840.0	2
U2OS CHEMBL615023	IC50	6.07	6.07	850.0	1
HeLa CHEMBL399	IC50	6.03	6.03	940.0	1
Activated CDC42 kinase 1 CHEMBL4599	Kd	6.03	6.03	929.0	1
Fibroblast growth factor receptor 4 CHEMBL3973	IC50	6.02	6.02	950.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	42603.59	ng.hr.mL-1	Macaca fascicularis
AUC	37898.39	ng.hr.mL-1	Canis lupus familiaris
AUC	10102.52	ng.hr.mL-1	Canis lupus familiaris
AUC	6865.24	ng.hr.mL-1	Mus musculus
AUC	6307.1	ng.hr.mL-1	Macaca fascicularis
AUC	3400.25	ng.hr.mL-1	Rattus norvegicus
AUC	3144.62	ng.hr.mL-1	Mus musculus
AUC	1551.1	ng.hr.mL-1	Rattus norvegicus
AUC	1380.0	ng.hr.mL-1	Rattus norvegicus
AUC	2650.0	ng.hr.mL-1	Rattus norvegicus
AUC	1098.6	ng.hr.mL-1	Rattus norvegicus
AUC	1249.7	ng.hr.mL-1	Rattus norvegicus
AUC	1400.0	ng.hr.mL-1	Rattus norvegicus
CL	36.8	mL.min-1.kg-1	Rattus norvegicus
CL	26.6	mL.min-1.kg-1	Mus musculus
CL	19.0	mL.min-1.g-1	Homo sapiens
CL	15.0	mL.min-1.g-1	Mus musculus
CL	12.8	mL.min-1.kg-1	Macaca fascicularis
CL	10.0	mL.min-1.g-1	Rattus norvegicus
CL	9.2	mL.min-1.kg-1	Canis lupus familiaris
Cmax	2526.0	nM	Macaca fascicularis
Cmax	2329.0	nM	Canis lupus familiaris
Cmax	1899.0	nM	Canis lupus familiaris
Cmax	1756.0	nM	Mus musculus
Cmax	1697.0	nM	Macaca fascicularis
Cmax	770.0	nM	Rattus norvegicus
Cmax	696.0	nM	Mus musculus
Cmax	259.0	nM	Rattus norvegicus
Cmax	160.89	nM	Rattus norvegicus
Cmax	102.23	nM	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
ALK tyrosine kinase receptor	IC50	=	0.2	nM	9.7	Inhibition of ALK (unknown origin)	35311289
ALK tyrosine kinase receptor	IC50	=	0.2	nM	9.7	Inhibition of ALK (unknown origin)	23837797
ALK tyrosine kinase receptor	IC50	=	0.2	nM	9.7	Inhibition of ALK (unknown origin) after 60 mins	23742252
ALK tyrosine kinase receptor	IC50	=	0.25	nM	9.6	Inhibition of ALK L1196M mutant (unknown origin)	34237620
Proto-oncogene tyrosine-protein kinase ROS	Ki	=	0.4	nM	9.4	Binding affinity to recombinant human ROS1 L2026M mutant assessed as inhibition ...	25733882
Proto-oncogene tyrosine-protein kinase ROS	Ki	=	0.4	nM	9.4	Inhibition of ROS1 L2026M mutant (unknown origin)	28431340
ALK tyrosine kinase receptor	IC50	=	0.61	nM	9.21	Inhibition of N-terminal GST tagged wild-type human ALK cytoplasmic domain (1058...	33185101
Unchecked	IC50	=	0.63	nM	9.2	Inhibition of ALK T1151-L1152 insT mutant (unknown origin) using peptide as subs...	27915169
Proto-oncogene tyrosine-protein kinase ROS	Ki	=	0.7	nM	9.15	Binding affinity to recombinant human ROS1 assessed as inhibition constant in pr...	25733882
Proto-oncogene tyrosine-protein kinase ROS	Ki	=	0.7	nM	9.15	Inhibition of wild type ROS1 (unknown origin)	28431340
ALK tyrosine kinase receptor	IC50	=	0.83	nM	9.08	Inhibition of wild type N-terminal GST tagged ALK L1196M mutant cytoplasmic doma...	35576654
ALK tyrosine kinase receptor	IC50	=	1.0	nM	9.0	Inhibitory Activity Against Anaplastic Lymphoma Kinase (ALK): A proliferation in...	-
ALK tyrosine kinase receptor	IC50	=	1.1	nM	8.96	Inhibition of human ALK L1196M mutant expressed Sf9 cells pre-incubated for 30 m...	33185101
ALK tyrosine kinase receptor	IC50	=	1.2	nM	8.92	Inhibition of wild type N-terminal GST tagged ALK cytoplasmic domain (1058 to 16...	35576654
ALK tyrosine kinase receptor	Kd	=	1.3	nM	8.89	Binding affinity to wild-type human partial length ALK (I1088 to E1409 residues)...	29627725
ALK tyrosine kinase receptor	IC50	=	1.4	nM	8.85	Inhibition of ALK G1269A mutant (unknown origin) using peptide as substrate meas...	27915169
ALK tyrosine kinase receptor	IC50	=	1.5	nM	8.82	Inhibition of ALK F1174L mutant (unknown origin) using peptide as substrate meas...	27915169
ALK tyrosine kinase receptor	IC50	=	1.6	nM	8.8	Inhibition of human ALK S1206Y mutant expressed Sf9 cells pre-incubated for 30 m...	33185101
Unchecked	IC50	=	1.7	nM	8.77	Inhibition of crizotinib-resistant ALK T1151-L1152 insT mutant (unknown origin) ...	26712094
ALK tyrosine kinase receptor	IC50	=	1.9	nM	8.72	Inhibition of human ALK G1269A mutant expressed Sf9 cells pre-incubated for 30 m...	33185101

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724801	Fibroblast	320
-	10.6019/CHEMBL5724801	U2OS	320
-	10.6019/CHEMBL5724801	HEK-293T	317
27780853	10.1158/1078-0432.ccr-16-0569	EML4-ALK	59
36628851	10.1016/j.ejmech.2022.115082	NCI-H3122	31
23742252	10.1021/jm400402q	Rattus norvegicus	15
23742252	10.1021/jm400402q	Mus musculus	13
28287083	10.1038/ncomms14768	Unchecked	12
23742252	10.1021/jm400402q	Canis familiaris	11
35691173	10.1016/j.ejmech.2022.114493	NCI-H2228	10
-	10.6019/CHEMBL5058564	U2OS	10
27915169	10.1016/j.ejmech.2016.11.046	ALK tyrosine kinase receptor	9
-	10.6019/CHEMBL5303304	U2OS	9
26568289	10.1021/acs.jmedchem.5b01136	NON-PROTEIN TARGET	9
23742252	10.1021/jm400402q	Cynomolgus monkey	9
29288940	10.1016/j.ejmech.2017.12.060	ALK tyrosine kinase receptor	9
-	10.6019/CHEMBL5303304	HEK-293T	8
26568289	10.1021/acs.jmedchem.5b01136	EML4-ALK	8
28528303	10.1016/j.ejmech.2017.04.079	Epidermal growth factor receptor	8
-	10.6019/CHEMBL5058564	HEK-293T	8

Data from ChEMBL 36 via Core Engine