Compound Detail

CHEMBL5416410

DASATINIB

💊 Approved Drug

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💊 Approved Drug

Cc1nc(Nc2ncc(C(=O)Nc3c(C)cccc3Cl)s2)cc(N2CCN(CCO)CC2)n1.O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL5416410
Name	DASATINIB
Phase	Approved
Structure Type	MOL
InChI Key	XHXFZZNHDVTMLI-UHFFFAOYSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL1421
Active Moiety	CHEMBL1421

Known Names

BMS-354825 HYDRATE BMS-354825-03 Dasatinib Dasatinib accord healthcare Dasatinib hydrate Dasatinib monohydrate NSC-759877 Sprycel

434

Targets

1,087

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

488.0

MW (Da)

3.31

ALogP

HBA

HBD

106.5

PSA (Å²)

0.47

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2006
Availability	Unknown
Chirality	Achiral

USAN Stem

-tinib

Extended Properties

Molecular Formula	C22H28ClN7O3S
MW	506.03
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-2.33

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Bcr/Abl fusion protein inhibitor	INHIBITOR	Bcr/Abl fusion protein	✓	✓

Indications

Leukemia, Myelogenous, Chronic, BCR-ABL Positive Precursor Cell Lymphoblastic Leukemia-Lymphoma

Activity Summary

IC50 657 meas. best 10.88

Kd 358 meas. best 10.8

Ki 47 meas. best 10.8

EC50 25 meas. best 10.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
EOL1 CHEMBL614489	IC50	10.88	10.88	0.0	1
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	10.8	9.4309	0.0	23
Bcr/Abl fusion protein CHEMBL2096618	IC50	10.8	8.05	0.0	7
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	Ki	10.8	10.4825	0.0	4
Bcr/Abl fusion protein CHEMBL2096618	Ki	10.52	10.52	0.0	2
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	10.52	9.2188	0.0	16
Unchecked CHEMBL612545	Ki	10.52	10.52	0.0	1
Ephrin type-B receptor 6 CHEMBL5836	Kd	10.41	8.94	0.0	2
Bcr/Abl fusion protein CHEMBL2096618	EC50	10.4	10.06	0.0	3
CTV-1 CHEMBL2366360	IC50	10.39	10.39	0.0	1
Proto-oncogene tyrosine-protein kinase LCK CHEMBL2480	Ki	10.19	10.19	0.1	1
K562 CHEMBL385	IC50	10.16	8.1353	0.1	17
NON-PROTEIN TARGET CHEMBL3879801	IC50	10.15	7.662	0.1	51
Ephrin type-A receptor 3 CHEMBL4954	Kd	10.03	10.03	0.1	2
Unchecked CHEMBL612545	IC50	10.0	6.822	0.1	15
KU812 cell line CHEMBL613997	IC50	10.0	8.46	0.1	2
HL-60 CHEMBL383	IC50	9.96	7.395	0.1	2
Tyrosine-protein kinase ABL1 CHEMBL1862	IC50	9.77	7.5964	0.2	28
Tyrosine-protein kinase ABL2 CHEMBL4014	Kd	9.77	9.3133	0.2	3
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	9.7	9.0233	0.2	3
Tyrosine-protein kinase Lck CHEMBL258	Kd	9.7	9.1833	0.2	3
Tyrosine-protein kinase Blk CHEMBL2250	Kd	9.68	9.68	0.2	2
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	Kd	9.68	9.104	0.2	5
Ephrin type-A receptor 5 CHEMBL3987	Kd	9.62	9.2133	0.2	3
Ephrin type-A receptor 8 CHEMBL4134	Kd	9.62	9.62	0.2	2
K562 CHEMBL385	EC50	9.59	9.02	0.3	3
Tyrosine-protein kinase Yes CHEMBL2073	Kd	9.52	9.1467	0.3	3
Tyrosine-protein kinase TXK CHEMBL4367	IC50	9.52	9.52	0.3	1
Tyrosine-protein kinase FRK CHEMBL4223	Kd	9.51	9.2075	0.3	4
Tyrosine-protein kinase HCK CHEMBL3234	Ki	9.5	9.5	0.3	1
Ephrin type-B receptor 4 CHEMBL5147	Kd	9.47	9.1133	0.3	3
Tyrosine-protein kinase HCK CHEMBL3234	Kd	9.46	8.82	0.3	3
Ephrin type-B receptor 2 CHEMBL3290	Kd	9.41	9.0733	0.4	3
Tyrosine-protein kinase Lck CHEMBL258	IC50	9.4	8.96	0.4	6
Proto-oncogene tyrosine-protein kinase Src CHEMBL3655	IC50	9.4	7.86	0.4	2
Discoidin domain-containing receptor 2 CHEMBL5122	IC50	9.4	8.3017	0.4	6
Ephrin type-B receptor 1 CHEMBL5072	Kd	9.35	9.35	0.5	2
Tyrosine-protein kinase ABL1 CHEMBL1862	Ki	9.34	9.34	0.5	1
Platelet-derived growth factor receptor alpha CHEMBL2007	Kd	9.33	9.33	0.5	2
Tyrosine-protein kinase Yes CHEMBL2073	IC50	9.3	9.3	0.5	3
Membrane-associated tyrosine- and threonine-specific cdc2-inhibitory kinase CHEMBL3984	Ki	9.3	8.22	0.5	2
Tyrosine-protein kinase Fgr CHEMBL4454	Kd	9.3	8.9667	0.5	3
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	IC50	9.3	8.81	0.5	2
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	IC50	9.24	8.3525	0.6	4
Macrophage colony-stimulating factor 1 receptor CHEMBL1844	Kd	9.24	9.24	0.6	3
Mast/stem cell growth factor receptor Kit CHEMBL1936	Kd	9.24	8.8	0.6	14
Tyrosine-protein kinase Lyn CHEMBL3905	Kd	9.24	8.86	0.6	3
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	9.2	8.3133	0.6	3
Tyrosine-protein kinase Srms CHEMBL5703	Ki	9.2	9.2	0.6	1
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	9.16	8.5633	0.7	3

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2342.5	ng.hr.mL-1	Mus musculus
AUC	6783.48	ng.hr.mL-1	Rattus norvegicus
AUC	1854.48	ng.hr.mL-1	Rattus norvegicus
AUC	304.52	ng.hr.mL-1	Homo sapiens
AUC	304.52	ng.hr.mL-1	Homo sapiens
AUC	213.26	ng.hr.mL-1	Mus musculus
AUC	219.61	ng.hr.mL-1	Mus musculus
AUC	287.44	ng.hr.mL-1	Mus musculus
AUC	335.27	ng.hr.mL-1	Mus musculus
AUC	-	-	Homo sapiens
AUC	48.8	ng.hr.mL-1	Mus musculus
CL	26400.0	mL.min-1.g-1	Rattus norvegicus
CL	28.18	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	75.0	mL.min-1.kg-1	Mus musculus
CL	40.0	%	Rattus norvegicus
Cmax	2700.0	nM	Mus musculus
Cmax	13200.0	nM	Rattus norvegicus
Cmax	500.0	nM	Rattus norvegicus
Cmax	200.0	nM	Homo sapiens
Cmax	1234.0	nM	Mus musculus
Cmax	202.0	nM	Mus musculus
F	27.0	%	Rattus norvegicus
F	4.0	%	Mus musculus
F	27.0	%	Rattus norvegicus
F	14.0	%	Mus musculus
F	27.0	%	Rattus norvegicus
F	27.0	%	Mus musculus
Fu	0.02	-	Homo sapiens
Fu	0.03	-	Mus musculus
Fu	0.026	-	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
EOL1	IC50	=	0.01309	nM	10.88	SANGER: Inhibition of human EoL-1-cell cell growth in a cell viability assay.	-
Bcr/Abl fusion protein	IC50	=	0.016	nM	10.8	Inhibition of BCR-Abl (unknown origin)	31926469
Tyrosine-protein kinase ABL1	Kd	=	0.016	nM	10.8	Binding constant for ABL1(M351T)-phosphorylated kinase domain	22037378
Proto-oncogene tyrosine-protein kinase Src	Ki	=	0.016	nM	10.8	Binding affinity to Src (unknown origin) assessed as inhibition constant	33148490
Proto-oncogene tyrosine-protein kinase Src	Ki	=	0.016	nM	10.8	Inhibition of SRC (unknown origin) assessed as inhibition constant	37801827
Proto-oncogene tyrosine-protein kinase Src	Ki	=	0.016	nM	10.8	Binding affinity to Src (unknown origin) assessed as inhibition constant in pres...	36758304
Tyrosine-protein kinase ABL1	Kd	=	0.019	nM	10.72	Binding constant for ABL1(F317L)-phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.025	nM	10.6	Binding constant for ABL1(H396P)-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.029	nM	10.54	Binding constant for ABL1-non phosphorylated kinase domain	22037378
Bcr/Abl fusion protein	Ki	=	0.03	nM	10.52	Binding affinity to Bcr-Abl (unknown origin) assessed as inhibition constant in ...	36758304
Proto-oncogene tyrosine-protein kinase Src	IC50	=	0.03	nM	10.52	Inhibition of SRC (unknown origin)	31926469
Unchecked	Ki	=	0.03	nM	10.52	Binding affinity to Abl (unknown origin) assessed as inhibition constant	33148490
Bcr/Abl fusion protein	Ki	=	0.03	nM	10.52	Binding affinity to wild type human BCR-ABL1 using Tyr2 peptide as substrate ass...	37801827
Tyrosine-protein kinase ABL1	Kd	=	0.032	nM	10.49	Binding constant for ABL1(F317L)-non phosphorylated kinase domain	22037378
Tyrosine-protein kinase ABL1	Kd	=	0.037	nM	10.43	Binding constant for ABL1(Q252H)-non phosphorylated kinase domain	22037378
Ephrin type-B receptor 6	Kd	=	0.039	nM	10.41	Binding constant for EPHB6 kinase domain	22037378
Bcr/Abl fusion protein	EC50	=	0.04	nM	10.4	Inhibition of human wild type BCR-ABL expressed in mouse BAF3 cells assessed as ...	27010810
Tyrosine-protein kinase ABL1	Kd	=	0.041	nM	10.39	Binding constant for ABL1(F317I)-phosphorylated kinase domain	22037378
CTV-1	IC50	=	0.04036	nM	10.39	SANGER: Inhibition of human CTV-1 cell growth in a cell viability assay.	-
Tyrosine-protein kinase ABL1	Kd	=	0.046	nM	10.34	Binding constant for ABL1(H396P)-phosphorylated kinase domain	22037378

Literature References

PubMed	DOI	Target Context	# Activities
31158845	10.1038/s41586-019-1291-3	ADMET	68
23301703	10.1021/jm301581y	NON-PROTEIN TARGET	16
23088644	10.1021/jm301188x	NON-PROTEIN TARGET	16
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15615512	10.1021/jm049486a	Rattus norvegicus	12
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
25835317	10.1021/acs.jmedchem.5b00270	MDA-MB-231	12
23301703	10.1021/jm301581y	Tyrosine-protein kinase ABL1	11
17360676	10.1073/pnas.0611681104	Dengue virus	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
18183025	10.1038/nbt1358	Epidermal growth factor receptor	10
19462975	10.1021/jm9002928	Proto-oncogene tyrosine-protein kinase Src	9
17684099	10.1073/pnas.0702654104	Tyrosine-protein kinase BTK	9
26789553	10.1021/acs.jmedchem.5b01618	Bcr/Abl fusion protein	9
18183025	10.1038/nbt1358	Tyrosine-protein kinase ABL1	8
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
27739679	10.1021/acs.jmedchem.6b00943	MDA-MB-231	8
31923860	10.1016/j.ejmech.2019.112029	ADMET	8

Data from ChEMBL 36 via Core Engine