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Compound Detail

CHEMBL343448

ROMIDEPSIN
💊 Approved Drug
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💊 Approved Drug
C/C=C1\NC(=O)[C@H]2CSSCC/C=C/[C@H](CC(=O)N[C@H](C(C)C)C(=O)N2)OC(=O)[C@H](C(C)C)NC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL343448
Name ROMIDEPSIN
Phase Approved
Structure Type MOL
InChI Key OHRURASPPZQGQM-GCCNXGTGSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL146250

Known Names

Chromadax Depsipeptide FK-228 FK228 FR-901228 FR901228 Istodax NSC-630176 Romidepsin Romidepsina Romidepsine
31
Targets
159
Activities
3
Assay Types
8
PK Parameters
20
Publications
11
Known Names
20
Indications
1
Mechanisms

Molecular Properties

540.7
MW (Da)
1.43
ALogP
8
HBA
4
HBD
142.7
PSA (Ų)
0.18
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Protein
First Approval 2009
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product Prodrug Chemical Probe
USAN Stem -depsin
USAN Year 2006

Extended Properties

Molecular Formula C24H36N4O6S2
MW 540.71
Aromatic Rings 0
Heavy Atoms 36
NP-Likeness 2.22

Mechanism of Action

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

Indications

Lymphoma, T-Cell Lymphoma, T-Cell, Cutaneous Lymphoma, T-Cell, Peripheral Lymphoma, T-Cell, Peripheral Neoplasms Neoplasms Immunoblastic Lymphadenopathy Lymphoma Adenocarcinoma, Follicular Breast Neoplasms Breast Neoplasms, Male Carcinoma, Non-Small-Cell Lung Colorectal Neoplasms HIV Infections HIV Infections Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Promyelocytic, Acute Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Lymphoma, Large-Cell, Anaplastic

ATC Classification

L01XH02
romidepsin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 128 meas. best 9.7
Ki 24 meas. best 10.42
EC50 7 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 2
CHEMBL1937
 Ki 10.42 10.0567 0.0 3
Histone deacetylase 3
CHEMBL1829
 Ki 9.82 9.355 0.1 2
Histone deacetylase 8
CHEMBL3192
 Ki 9.82 9.82 0.1 2
Histone deacetylase 3/NCoR1
CHEMBL3038484
 Ki 9.82 9.82 0.1 1
Histone deacetylase 1
CHEMBL325
 IC50 9.7 8.235 0.2 28
Histone deacetylase 11
CHEMBL3310
 IC50 9.52 9.52 0.3 3
Histone deacetylase 6
CHEMBL2878
 IC50 9.2 7.016 0.6 5
MCF7
CHEMBL387
 IC50 9.12 9.12 0.8 1
Histone deacetylase 1
CHEMBL325
 Ki 9.06 9.06 0.9 1
Histone deacetylase 3
CHEMBL1829
 IC50 9.05 8.6917 0.9 6
Histone deacetylase
CHEMBL5541
 IC50 9.05 9.05 0.9 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 9.05 8.802 0.9 5
NFF
CHEMBL614198
 IC50 9.0 9.0 1.0 1
Histone deacetylase
CHEMBL2093865
 IC50 9.0 7.766 1.0 5
Histone deacetylase 2
CHEMBL1937
 IC50 9.0 7.9175 1.0 16
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.96 8.74 1.1 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 8.52 7.6 3.0 6
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.52 7.81 3.0 2
Unchecked
CHEMBL612545
 EC50 8.35 7.315 4.5 2
Histone deacetylase 6
CHEMBL1865
 IC50 8.04 6.2474 9.1 19
Histone deacetylase 6
CHEMBL1865
 Ki 8.02 7.5133 9.5 3
Histone deacetylase 8
CHEMBL3192
 IC50 8.0 7.7 10.0 2
Histone deacetylase 4
CHEMBL3524
 Ki 7.69 7.69 20.5 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 Ki 7.6 7.6 24.9 1
A549
CHEMBL392
 IC50 7.6 7.6 25.0 1
HCT-116
CHEMBL394
 IC50 7.55 7.55 28.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 7.46 7.46 35.0 1
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.44 7.44 36.0 1
Plasmodium falciparum
CHEMBL364
 IC50 7.05 7.018 90.0 5
Protein Tat
CHEMBL4011
 EC50 6.66 6.66 220.0 1
IGROV-1
CHEMBL613984
 IC50 6.66 6.66 220.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 6.29 6.0923 510.0 13
Histone deacetylase 5
CHEMBL2563
 Ki 6.26 6.26 550.0 2
Histone deacetylase 9
CHEMBL4145
 Ki 5.96 5.96 1100.0 2
Histone deacetylase 7
CHEMBL2716
 Ki 5.9 5.9 1250.0 2
Histone deacetylase 2/Nuclear receptor corepressor 2
CHEMBL3885591
 IC50 5.82 5.82 1500.0 1
Unchecked
CHEMBL612545
 IC50 5.7 5.7 2000.0 1
Histone deacetylase 1/Nuclear receptor corepressor 2
CHEMBL3885590
 IC50 5.17 5.17 6700.0 1
Histone deacetylase 1
CHEMBL325
 EC50 4.44 4.44 36000.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 4.24 4.24 57100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.4 mL.min-1.kg-1 Homo sapiens
MRT 2.6 hr Homo sapiens
T1/2 11.0 hr Homo sapiens
T1/2 0.4333 hr Homo sapiens
T1/2 0.6833 hr Homo sapiens
T1/2 1666.67 hr Homo sapiens
T1/2 0.9833 hr Homo sapiens
T1/2 3.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 2 Ki = 0.038 nM 10.42 Inhibition of human HDAC2 20139990
Histone deacetylase 2 Ki = 0.038 nM 10.42 Inhibition of recombinant human HDAC2 enzyme using flurogenic Ac-LeuGlyLys (Ac)-... 23865683
Histone deacetylase 3 Ki = 0.15 nM 9.82 Inhibition of human HDAC3 20139990
Histone deacetylase 8 Ki = 0.15 nM 9.82 Activity of human HDAC8 20139990
Histone deacetylase 8 Ki = 0.15 nM 9.82 Inhibition of recombinant human HDAC8 enzyme using Ac-LeuGlyLys (tfa)-AMC as sub... 23865683
Histone deacetylase 3/NCoR1 Ki = 0.15 nM 9.82 Inhibition of GST-tagged recombinant human HDAC3/NcoR1 enzyme using flurogenic A... 23865683
Histone deacetylase 1 IC50 = 0.2 nM 9.7 Inhibition of recombinant HDAC1 using Ac-Lys(Ac)-AMC as substrate after 30 mins ... 24900500
Histone deacetylase 11 IC50 = 0.3 nM 9.52 Inhibition of HDAC11 (unknown origin) incubated for 3 hrs in presence of BSA and... 25147612
Histone deacetylase 11 IC50 = 0.3 nM 9.52 Inhibition of HDAC11 (unknown origin) 32608981
Histone deacetylase 11 IC50 = 0.3 nM 9.52 Inhibition of HDAC11 (unknown origin) 38520762
Histone deacetylase 1 IC50 = 0.31 nM 9.51 Inhibition of human recombinant HDAC1 after 1 hr by luminescence assay 23997923
Histone deacetylase 2 Ki = 0.47 nM 9.33 Binding affinity to HDAC2 (unknown origin) using Ac-LGKac-AMC as substrate asses... 37651268
Histone deacetylase 6 IC50 = 0.625 nM 9.2 Inhibition of mouse HDAC6 using fluorescent substrate Ac-KGLGK(Ac)-MCA after 30 ... 24997578
MCF7 IC50 = 0.75 nM 9.12 Growth inhibition of MCF7 cells 17958342
Histone deacetylase 1 IC50 = 0.8 nM 9.1 Inhibition of HDAC1 (unknown origin) incubated for 30 mins in presence of BSA an... 25147612
Histone deacetylase 1 Ki = 0.88 nM 9.06 Binding affinity to HDAC1 (unknown origin) using Ac-LGKac-AMC as substrate asses... 37651268
Histone deacetylase 3 IC50 = 0.9 nM 9.05 Inhibition of HDAC3 in human DU-145 cells assessed as increase in histone H3 ace... 35133171
Histone deacetylase IC50 = 0.9 nM 9.05 Inhibition of HDAC1 in Plasmodium falciparum 3D7 nuclear extract using Ac-RGK(Ac... 28241112
Polyamine deacetylase HDAC10 IC50 = 0.9 nM 9.05 Inhibition of HDAC10 (unknown origin) incubated for 30 mins in presence of BSA a... 25147612
Polyamine deacetylase HDAC10 IC50 = 1.0 nM 9.0 Inhibition of HDAC10 (unknown origin) 38520762

Literature References

PubMed DOI Target Context # Activities
24589486 10.1016/j.ejmech.2014.02.044 NON-PROTEIN TARGET 14
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 1 7
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 2 6
23313638 10.1016/j.ejmech.2012.12.023 NON-PROTEIN TARGET 6
18426954 10.1124/dmd.108.020479 ADMET 4
27318982 10.1016/j.ejmech.2016.05.031 Unchecked 4
21967146 10.1021/np200532d U-251 4
21793558 10.1021/np200324x Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 4
21967146 10.1021/np200532d COLO 205 4
28241112 10.1021/acs.jmedchem.6b01595 Unchecked 4
21967146 10.1021/np200532d SF-295 4
21967146 10.1021/np200532d MDA-MB-231 4
30245402 10.1016/j.ejmech.2018.09.018 Unchecked 4
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 3 3
26331334 10.1021/acs.jmedchem.5b01044 ADMET 3
30973727 10.1021/acs.jmedchem.9b00462 Protein Tat 3
18430569 10.1016/j.bmcl.2008.04.007 Histone deacetylase 6 2
18430569 10.1016/j.bmcl.2008.04.007 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 2
21967146 10.1021/np200532d NCI 2
21967146 10.1021/np200532d LOX IMVI 2

Data from ChEMBL 36 via Core Engine