Compound Detail

CHEMBL27759

ENTINOSTAT

🧪 Phase III

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🧪 Phase III

Nc1ccccc1NC(=O)c1ccc(CNC(=O)OCc2cccnc2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL27759
Name	ENTINOSTAT
Phase	Phase III
Structure Type	MOL
InChI Key	INVTYAOGFAGBOE-UHFFFAOYSA-N

Known Names

Entinostat MS-27-275 MS-275-27 SNDX-275

378

Targets

752

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

376.4

MW (Da)

3.34

ALogP

HBA

HBD

106.3

PSA (Å²)

0.57

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem	-stat
USAN Year	2008

Extended Properties

Molecular Formula	C21H20N4O3
MW	376.42
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	-1.26

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Histone deacetylase inhibitor	INHIBITOR	Histone deacetylase	✓	✓

Indications

Breast Neoplasms Breast Neoplasms Breast Neoplasms Neoplasms Neoplasms Breast Neoplasms, Male Carcinoma, Non-Small-Cell Lung Carcinoma, Renal Cell Carcinoma, Renal Cell Colonic Neoplasms Hodgkin Disease Leukemia, Myeloid, Acute Lymphoma Melanoma Myelodysplastic Syndromes Neuroendocrine Tumors Rectal Neoplasms Triple Negative Breast Neoplasms Urinary Bladder Neoplasms Uveal Melanoma

ATC Classification

L01XH05

entinostat

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 731 meas. best 9.7

Ki 12 meas. best 8.24

EC50 7 meas. best 6.75

Kd 2 meas. best 6.81

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase 1 CHEMBL325	IC50	9.7	6.5754	0.2	69
Histone deacetylase 9 CHEMBL4145	IC50	9.3	9.3	0.5	1
HepG2 CHEMBL395	IC50	9.05	6.032	0.9	5
Histone deacetylase 2 CHEMBL1937	IC50	8.92	6.4251	1.2	39
Histone deacetylase 3 CHEMBL1829	IC50	8.64	6.3642	2.3	33
Histone deacetylase 2 CHEMBL1937	Ki	8.24	7.404	5.7	5
Histone deacetylase 1 CHEMBL325	Ki	7.66	6.945	22.0	2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	Ki	7.62	7.025	24.0	4
Histone deacetylase 6 CHEMBL1865	IC50	7.47	5.6213	34.0	8
Unchecked CHEMBL612545	IC50	7.4	5.6665	40.0	23
SCC-3 CHEMBL2366081	IC50	7.21	7.21	61.0	1
ALL-PO CHEMBL2366294	IC50	7.2	7.2	63.5	1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	7.11	6.1733	77.2	6
KM3/BTZ CHEMBL4483251	IC50	7.01	6.35	98.0	2
697 CHEMBL2366253	IC50	7.0	7.0	99.8	1
NCI-H748 CHEMBL2366163	IC50	6.99	6.99	103.3	1
NKM-1 CHEMBL2366133	IC50	6.96	6.96	109.1	1
ES1 CHEMBL2366146	IC50	6.95	6.95	112.5	1
NCI-H1963 CHEMBL2366075	IC50	6.94	6.94	115.8	1
NCI-H1417 CHEMBL2366149	IC50	6.89	6.89	129.7	1
NEC8 CHEMBL2366340	IC50	6.87	6.87	135.3	1
Histone deacetylase 1 CHEMBL325	Kd	6.81	6.81	156.0	1
CRO-AP2 CHEMBL2366080	IC50	6.77	6.77	168.9	1
A3-KAW CHEMBL2366273	IC50	6.75	6.75	176.3	1
Histone deacetylase 1 CHEMBL325	EC50	6.75	6.375	180.0	2
Histone deacetylase 8 CHEMBL3192	IC50	6.74	5.1293	181.0	14
NOS-1 CHEMBL2366141	IC50	6.71	6.71	196.2	1
SF-539 CHEMBL614860	IC50	6.71	6.71	195.9	1
NTERA-2-cl-D1 CHEMBL614206	IC50	6.7	6.7	201.1	1
COR-L88 CHEMBL2366329	IC50	6.64	6.64	229.6	1
Histone deacetylase CHEMBL2093865	IC50	6.63	5.5057	233.0	21
EM-2 CHEMBL2366281	IC50	6.62	6.62	240.8	1
MV4-11 CHEMBL613835	IC50	6.62	6.4175	240.0	4
Jurkat CHEMBL397	IC50	6.6	6.4367	250.0	3
Histone deacetylase 2 CHEMBL1937	Kd	6.55	6.55	282.0	1
KARPAS-45 CHEMBL2366305	IC50	6.55	6.55	278.3	1
DSH1 CHEMBL2366079	IC50	6.54	6.54	287.1	1
RS4-11 CHEMBL2366159	IC50	6.52	5.32	300.0	2
HT-144 CHEMBL2366291	IC50	6.52	6.52	302.6	1
ATN-1 CHEMBL2366277	IC50	6.51	6.51	305.8	1
NB12 CHEMBL2366285	IC50	6.5	6.5	317.6	1
HEL CHEMBL613888	IC50	6.5	6.2675	313.5	4
C6 CHEMBL614657	IC50	6.48	6.48	330.0	1
MOLT-13 CHEMBL2366103	IC50	6.47	6.47	338.1	1
J-RT3-T3-5 CHEMBL2366219	IC50	6.47	6.47	337.2	1
LU-139 CHEMBL2366248	IC50	6.47	6.47	335.1	1
AGS CHEMBL613860	IC50	6.47	5.52	340.0	2
MCF7 CHEMBL387	IC50	6.46	5.465	350.0	6
SR CHEMBL614300	IC50	6.46	6.46	342.6	1
CMK CHEMBL2366177	IC50	6.45	6.45	357.3	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	5264.0	ng.hr.mL-1	Mus musculus
Cmax	16595.82	nM	Mus musculus
ka	0.46	/uM/min	Homo sapiens
MRT	0.96	hr	Mus musculus
T1/2	6.75	hr	Rattus norvegicus
T1/2	6.75	hr	Homo sapiens
T1/2	33.9	hr	Homo sapiens
T1/2	52.0	hr	Homo sapiens
T1/2	16666.67	hr	Homo sapiens
T1/2	4.0	hr	Homo sapiens
T1/2	1.583	hr	Homo sapiens
T1/2	0.75	hr	Homo sapiens
T1/2	3.18	hr	Mus musculus
Tmax	0.25	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase 1	IC50	=	0.2	nM	9.7	Inhibition of recombinant human HDAC1 using pan-HDAC substrate incubated for 3 h...	32608981
Histone deacetylase 9	IC50	=	0.5	nM	9.3	Inhibition of recombinant human HDAC9 using pan-HDAC substrate incubated for 3 h...	32608981
HepG2	IC50	=	0.9	nM	9.05	Inhibition of human HepG2 cells	18247554
Histone deacetylase 2	IC50	=	1.2	nM	8.92	Inhibition of recombinant human HDAC2 using pan-HDAC substrate incubated for 3 h...	32608981
Histone deacetylase 3	IC50	=	2.3	nM	8.64	Inhibition of recombinant human HDAC3 using pan-HDAC substrate incubated for 3 h...	32608981
Histone deacetylase 2	Ki	=	5.7	nM	8.24	Inhibition of full-length recombinant human C-terminal GST tagged HDAC2 expresse...	37847303
Histone deacetylase 2	Ki	=	6.0	nM	8.22	Inhibition of full length C-terminal FLAG-tagged HDAC2 (unknown origin) assessed...	35586419
Histone deacetylase 1	IC50	=	14.0	nM	7.85	Inhibition of Histone Deacetylase Enzymatic Activity: The following non-trypsin ...	-
Histone deacetylase 2	IC50	=	15.0	nM	7.82	Inhibition of HDAC2	20472442
Histone deacetylase 1	Ki	=	22.0	nM	7.66	Inhibition of human HDAC1	20139990
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Ki	=	24.0	nM	7.62	Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina...	35586419
Histone deacetylase 1	IC50	=	25.0	nM	7.6	Inhibition of HDAC1	20472442
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Ki	=	27.0	nM	7.57	Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina...	35586419
Histone deacetylase 6	IC50	=	34.0	nM	7.47	Inhibition of recombinant human HDAC6 using ZMAL (Z-(Ac)Lys-AMC as substrate inc...	35306288
Histone deacetylase 3	IC50	=	35.0	nM	7.46	Inhibition of full length recombinant human HDAC3 expressed in Sf9 cells using 6...	38060537
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	Ki	=	39.0	nM	7.41	Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina...	35586419
Unchecked	IC50	=	40.0	nM	7.4	Inhibition of HDAC3-SMRT (unknown origin) using Boc-(Ac)Lys-AMC as substrate pre...	36545434
Histone deacetylase 1	IC50	=	44.0	nM	7.36	Inhibition of recombinant human HDAC1 using Cbz-Lys(TFAc)-AMC as substrate by fl...	20947351
Histone deacetylase 1	IC50	=	53.89	nM	7.27	Inhibition of recombinant HDAC1 (unknown origin) using Boc-Lys(acetyl)-AMC as su...	32321249
SCC-3	IC50	=	61.0	nM	7.21	SANGER: Inhibition of human SCC-3 cell growth in a cell viability assay.	-

Literature References

PubMed	DOI	Target Context	# Activities
32267687	10.1021/acs.jmedchem.9b02161	KM3/BTZ	26
31003060	10.1016/j.ejmech.2019.04.017	SMMC-7721	25
29202397	10.1016/j.ejmech.2017.08.041	SMMC-7721	21
32940035	10.1021/acs.jmedchem.0c01541	No relevant target	15
24900596	10.1021/ml400289e	Histone deacetylase	14
28109947	10.1016/j.ejmech.2016.12.032	Unchecked	12
20452226	10.1016/j.bmc.2010.04.033	HCT-116	11
22321215	10.1016/j.bmcl.2012.01.053	HCT-116	10
34097389	10.1021/acs.jmedchem.1c00413	B16-F10	10
38060537	10.1021/acs.jmedchem.3c01236	ADMET	8
32325365	10.1016/j.ejmech.2020.112291	MDA-MB-231	8
19966789	10.1038/nchembio.275	Histone deacetylase	8
35586419	10.1021/acsmedchemlett.1c00702	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	8
34097389	10.1021/acs.jmedchem.1c00413	ADMET	7
18381238	10.1016/j.bmcl.2008.03.055	U-937	7
28511906	10.1016/j.bmc.2017.03.036	Unchecked	6
34097389	10.1021/acs.jmedchem.1c00413	Unchecked	6
35586419	10.1021/acsmedchemlett.1c00702	Histone deacetylase 2	6
35041998	10.1016/j.bmc.2021.116599	Histone deacetylase 1/2/3	6
23089527	10.1016/j.bmcl.2012.09.093	Histone deacetylase	6

Data from ChEMBL 36 via Core Engine