Compound Detail

CHEMBL98

VORINOSTAT

💊 Approved Drug

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💊 Approved Drug

O=C(CCCCCCC(=O)Nc1ccccc1)NO

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL98
Name	VORINOSTAT
Phase	Approved
Structure Type	MOL
InChI Key	WAEXFXRVDQXREF-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

MK-0683 MK0683 NSC-701852 NSC-748799 NSC-759852 Suberoylanilide hydroxamic acid Vorinostat Zolinza

744

Targets

4,329

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

264.3

MW (Da)

2.47

ALogP

HBA

HBD

78.4

PSA (Å²)

0.38

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2006
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-stat
USAN Year	2005

Extended Properties

Molecular Formula	C14H20N2O3
MW	264.32
Aromatic Rings	1
Heavy Atoms	19
NP-Likeness	-0.62

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Histone deacetylase 1 inhibitor	INHIBITOR	Histone deacetylase 1	✓	✓
Histone deacetylase 3 inhibitor	INHIBITOR	Histone deacetylase 3	✓	✓
Histone deacetylase 6 inhibitor	INHIBITOR	Histone deacetylase 6	✓	✓
Histone deacetylase 2 inhibitor	INHIBITOR	Histone deacetylase 2	✓	✓

Indications

Lymphoma, T-Cell Lymphoma, T-Cell, Cutaneous Neoplasms Neoplasms Leukemia, Myeloid, Acute Lung Neoplasms Lymphoma Mesothelioma Mesothelioma Multiple Myeloma Adenocarcinoma, Follicular Anemia, Sickle Cell Astrocytoma Brain Diseases Brain Neoplasms Brain Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms, Male Carcinoma, Medullary

ATC Classification

L01XH01

vorinostat

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 4,123 meas. best 9.68

EC50 105 meas. best 8.41

Ki 92 meas. best 9.0

Kd 9 meas. best 7.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
K562 CHEMBL385	IC50	9.68	5.9506	0.2	65
Histone deacetylase 1 CHEMBL325	IC50	9.64	7.3016	0.2	389
Histone deacetylase CHEMBL2093865	IC50	9.46	6.7253	0.3	165
Ramos CHEMBL614629	IC50	9.28	6.4775	0.5	8
HepG2 CHEMBL395	IC50	9.22	5.667	0.6	53
Unchecked CHEMBL612545	IC50	9.18	6.0821	0.7	106
Raji CHEMBL614628	IC50	9.01	6.2633	1.0	9
Histone deacetylase 6 CHEMBL1865	IC50	9.0	7.433	1.0	327
Histone deacetylase 6 CHEMBL1865	Ki	9.0	7.8036	1.0	11
Histone deacetylase 5 CHEMBL2563	IC50	9.0	5.5436	1.0	42
Histone deacetylase 4 CHEMBL3524	IC50	9.0	5.7467	1.0	52
Histone deacetylase 9 CHEMBL4145	IC50	9.0	5.7719	1.0	27
Histone deacetylase 1 CHEMBL325	Ki	8.89	7.9279	1.3	14
Histone deacetylase 3 CHEMBL1829	IC50	8.85	7.2976	1.4	164
Histone deacetylase 2 CHEMBL1937	Ki	8.8	7.8291	1.6	11
Histone deacetylase 3 CHEMBL1829	Ki	8.77	7.9563	1.7	8
Histone deacetylase 2 CHEMBL1937	IC50	8.77	7.0016	1.7	221
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	Ki	8.7	8.21	2.0	3
Histone deacetylase 7 CHEMBL2716	IC50	8.7	5.6488	2.0	33
HT-1080 CHEMBL614580	IC50	8.62	6.049	2.4	10
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	8.52	7.25	3.0	40
HDAC1/REST corepressor 3 CHEMBL4296112	Ki	8.52	8.52	3.0	1
Unchecked CHEMBL612545	EC50	8.41	5.9145	3.9	11
Histone deacetylase 11 CHEMBL3310	IC50	8.4	6.3132	4.0	37
Histone deacetylase 8 CHEMBL3192	IC50	8.26	6.1706	5.5	193
Plasmodium berghei CHEMBL612653	IC50	8.11	7.028	7.7	5
Histone deacetylase 3/NCoR1 CHEMBL3038484	IC50	8.01	7.5233	9.8	3
Bromodomain-containing protein 4 CHEMBL1163125	IC50	8.0	7.1667	10.0	3
Histone deacetylase (HDAC1 and HDAC2) CHEMBL2111429	IC50	8.0	6.96	10.0	23
Histone deacetylase 3/NCoR1 CHEMBL3038484	Ki	8.0	7.96	9.9	2
MCF7 CHEMBL387	EC50	8.0	7.095	10.0	2
MM96L CHEMBL614170	EC50	8.0	8.0	10.0	1
HCT-116 CHEMBL394	IC50	7.93	5.8432	11.8	112
Epidermal growth factor receptor CHEMBL203	IC50	7.92	6.985	12.0	2
A549 CHEMBL392	IC50	7.9	5.6121	12.5	104
Histone deacetylase 11 CHEMBL3310	Ki	7.89	7.59	13.0	5
Unchecked CHEMBL612545	Ki	7.85	7.09	14.0	3
Histone deacetylase 4 CHEMBL3524	Ki	7.8	5.884	16.0	5
HEL CHEMBL613888	IC50	7.7	6.3696	20.0	27
Histone deacetylase 6 CHEMBL1865	EC50	7.66	6.484	21.7	5
Plasmodium falciparum CHEMBL364	IC50	7.6	6.5287	25.0	45
Polyamine deacetylase HDAC10 CHEMBL5103	IC50	7.57	6.809	27.0	60
Histone deacetylase HD1B CHEMBL3541	IC50	7.55	7.535	28.0	2
Histone deacetylase 5 CHEMBL2563	Ki	7.48	6.32	33.0	4
Class 1 histone deacetylase CHEMBL4523988	IC50	7.47	5.9888	34.0	8
Histone deacetylase 1 CHEMBL325	Kd	7.4	7.07	40.0	2
Polyamine deacetylase HDAC10 CHEMBL5103	Ki	7.4	7.33	40.0	4
Histone deacetylase 9 CHEMBL4145	Ki	7.31	6.7333	49.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.3	5.8084	50.0	147
Histone deacetylase HD2 CHEMBL4919	IC50	7.3	7.0636	50.0	11

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	200.0	ng.hr.mL-1	Mus musculus
AUC	600.0	ng.hr.mL-1	Mus musculus
AUC	400.0	ng.hr.mL-1	Rattus norvegicus
AUC	200.0	ng.hr.mL-1	Mus musculus
AUC	600.0	ng.hr.mL-1	Mus musculus
AUC	400.0	ng.hr.mL-1	Rattus norvegicus
AUC	657.0	ng.hr.mL-1	Mus musculus
AUC	1486.0	ng.hr.mL-1	Mus musculus
AUC	619.0	ng.hr.mL-1	Mus musculus
AUC	965.14	ng.hr.mL-1	Canis lupus familiaris
AUC	968.32	ng.hr.mL-1	Canis lupus familiaris
AUC	783.0	ng.hr.mL-1	Mus musculus
AUC	2554.0	ng.hr.mL-1	Mus musculus
CL	78.0	mL.min-1.kg-1	Mus musculus
CL	67.0	mL.min-1.kg-1	Rattus norvegicus
CL	78.0	mL.min-1.kg-1	Mus musculus
CL	67.0	mL.min-1.kg-1	Rattus norvegicus
CL	127.0	mL.min-1.kg-1	Mus musculus
CL	112.17	mL.min-1.kg-1	Mus musculus
CL	28.0	mL.min-1.kg-1	Homo sapiens
CL	0.1122	mL.min-1.kg-1	Mus musculus
CL	0.1	mL.min-1.kg-1	Homo sapiens
CL	33.0	mL.min-1.kg-1	Mus musculus
CL	112.0	mL.min-1.kg-1	Mus musculus
CL	2.04	mL.min-1.g-1	Mus musculus
CL	4.02	mL.min-1.g-1	Homo sapiens
CL	8.6	mL.min-1.kg-1	Homo sapiens
CL	13636.0	mL.min-1.kg-1	Mus musculus
Cmax	1895429.78	nM	Mus musculus
Cmax	449.83	nM	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
K562	IC50	=	0.21	nM	9.68	Antiproliferative activity against human K562 cells assessed as cell growth inhi...	36622852
Histone deacetylase 1	IC50	=	0.23	nM	9.64	Fluorescence Detection: Enzymatic activity was tested in 96-well or 384-well fla...	-
Histone deacetylase	IC50	=	0.35	nM	9.46	Inhibition of HDAC in human HeLa cells nuclear extract incubated for 30 mins by ...	37057760
Ramos	IC50	=	0.52	nM	9.28	Antiproliferative activity against human Ramos cells after 72 hrs by MTT assay	28325601
HepG2	IC50	=	0.6	nM	9.22	Inhibition of human HepG2 cells	18247554
Unchecked	IC50	=	0.66	nM	9.18	Antiproliferative activity against human RPMI8266 cells after 72 hrs by MTT assa...	28325601
Histone deacetylase 1	IC50	=	0.85	nM	9.07	Inhibition of HDAC1 in human HeLa cells nuclear extract incubated for 30 mins by...	37057760
Raji	IC50	=	0.97	nM	9.01	Antiproliferative activity against human Raji cells after 72 hrs by MTT assay	28325601
Histone deacetylase 6	IC50	=	1.0	nM	9.0	Inhibition of HDAC6 (unknown origin)	38520762
Histone deacetylase 4	IC50	=	1.0	nM	9.0	Inhibition of HDAC4 (unknown origin)	38520762
Histone deacetylase 5	IC50	=	1.0	nM	9.0	Inhibition of HDAC5 (unknown origin)	38520762
Histone deacetylase 9	IC50	=	1.0	nM	9.0	Inhibition of HDAC9 (unknown origin)	38520762
Histone deacetylase 6	Ki	=	1.0	nM	9.0	Displacement of fluorescent 5-(3-(3-(4-((4-((7-(hydroxyamino)-7-oxoheptyl)carbam...	18430569
Histone deacetylase 1	Ki	=	1.3	nM	8.89	Inhibition of human HDAC1	20139990
Histone deacetylase 6	IC50	=	1.4	nM	8.85	Inhibition of human KDAC6	26681404
Histone deacetylase 3	IC50	=	1.4	nM	8.85	Inhibition of human KDAC3	26681404
Histone deacetylase 2	Ki	=	1.6	nM	8.8	Inhibition of human HDAC2	20139990
Histone deacetylase 6	Ki	=	1.6	nM	8.8	Inhibition of human HDAC6	20139990
Histone deacetylase 3	Ki	=	1.7	nM	8.77	Binding affinity to recombinant human HDAC3 assessed as inhibition constant	37651268
Histone deacetylase 2	IC50	=	1.7	nM	8.77	Inhibition of human recombinant HDAC2 after 30 mins by fluorometric assay	22439863

Literature References

PubMed	DOI	Target Context	# Activities
28218840	10.1021/acs.jmedchem.6b01507	Mus musculus	49
23252603	10.1021/jm301254q	CAL-27	46
23252603	10.1021/jm301254q	MDA-MB-231	46
23252603	10.1021/jm301254q	A2780	46
23252603	10.1021/jm301254q	KYSE-510	46
24613456	10.1016/j.bmc.2014.02.018	Jurkat	24
24694055	10.1021/jm401877m	U-937	24
35238576	10.1021/acs.jmedchem.1c02026	HEL	21
34116381	10.1016/j.bmc.2021.116251	Unchecked	21
36449947	10.1021/acs.jmedchem.2c01413	SNU-16	19
31938464	10.1021/acsmedchemlett.9b00471	MV4-11	17
27541357	10.1021/acs.jmedchem.6b00157	NON-PROTEIN TARGET	16
30559935	10.18632/oncotarget.26370	Histone deacetylase	16
31883490	10.1016/j.ejmech.2019.111991	HL-60	16
20218673	10.1021/jm901358y	Mus musculus	16
28648461	10.1016/j.bmcl.2017.06.033	Unchecked	16
19966789	10.1038/nchembio.275	Histone deacetylase 7	16
-	10.1039/C5MD00247H	HeLa	16
30045621	10.1021/acs.jmedchem.8b00664	A549	16
32151834	10.1016/j.ejmech.2020.112189	HCT-116	16

Data from ChEMBL 36 via Core Engine