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Compound Detail

CHEMBL3414621

TAZEMETOSTAT
💊 Approved Drug
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💊 Approved Drug
CCN(c1cc(-c2ccc(CN3CCOCC3)cc2)cc(C(=O)NCc2c(C)cc(C)[nH]c2=O)c1C)C1CCOCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3414621
Name TAZEMETOSTAT
Phase Approved
Structure Type MOL
InChI Key NSQSAUGJQHDYNO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

E-7438 E7438 EPZ-6438 EPZ6438 Tazemetostat
25
Targets
103
Activities
4
Assay Types
30
PK Parameters
20
Publications
5
Known Names
13
Indications

Molecular Properties

572.8
MW (Da)
4.73
ALogP
6
HBA
2
HBD
86.9
PSA (Ų)
0.39
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2020
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product First in Class Chemical Probe
USAN Stem -stat
USAN Year 2018

Extended Properties

Molecular Formula C34H44N4O4
MW 572.75
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness -1.18

Indications

Neoplasms Lymphoma, Follicular Lymphoma, Follicular Sarcoma Lymphoma Mesothelioma Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Leukemia, Myeloid, Acute Lymphoma, Large B-Cell, Diffuse Multiple Myeloma Prostatic Neoplasms Urinary Bladder Neoplasms

ATC Classification

L01XX72
tazemetostat
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 84 meas. best 9.47
EC50 10 meas. best 8.3
Ki 5 meas. best 8.6
Kd 4 meas. best 8.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone-lysine N-methyltransferase EZH2
CHEMBL2189110
 IC50 9.47 8.1958 0.3 36
Unchecked
CHEMBL612545
 IC50 9.43 7.5373 0.4 11
Polycomb protein EED
CHEMBL2189117
 IC50 8.7 8.05 2.0 2
Pfeiffer
CHEMBL4296489
 IC50 8.65 7.8467 2.3 3
Unchecked
CHEMBL612545
 Ki 8.6 8.6 2.5 2
Histone-lysine N-methyltransferase EZH2
CHEMBL2189110
 Ki 8.6 8.6 2.5 3
KARPAS-422
CHEMBL2366368
 IC50 8.41 7.58 3.9 4
Histone-lysine N-methyltransferase EZH2
CHEMBL4739840
 IC50 8.4 8.4 4.0 1
EZH1/SUZ12/EED/AEBP2/RBBP4 complex
CHEMBL3137287
 IC50 8.4 8.4 4.0 1
Histone-lysine N-methyltransferase EZH2
CHEMBL2189110
 EC50 8.3 7.348 5.0 10
WSUDLCL2
CHEMBL5058628
 IC50 8.19 8.19 6.4 1
Unchecked
CHEMBL612545
 Kd 8.07 7.98 8.6 3
Histone-lysine N-methyltransferase EZH2
CHEMBL2189110
 Kd 8.04 8.04 9.1 1
Histone-lysine N-methyltransferase EZH1
CHEMBL2189116
 IC50 7.03 6.555 93.0 4
Medulloblastoma cell
CHEMBL4296520
 IC50 5.06 5.06 8740.0 1
MDA-MB-231
CHEMBL400
 IC50 4.96 4.53 11070.0 3
SUD4
CHEMBL613711
 IC50 4.84 4.84 14340.0 1
BT-549
CHEMBL614072
 IC50 4.81 4.43 15360.0 3
A549
CHEMBL392
 IC50 4.8 4.8 15830.0 1
SU-DHL-6
CHEMBL4296496
 IC50 4.66 4.66 21950.0 1
MV4-11
CHEMBL613835
 IC50 4.65 4.65 22380.0 1
HeLa
CHEMBL399
 IC50 4.56 4.56 27690.0 1
4T1
CHEMBL612589
 IC50 4.53 4.53 29300.0 1
A2780
CHEMBL614004
 IC50 4.33 4.33 47000.0 1
MDA-MB-468
CHEMBL614335
 IC50 4.33 4.33 46670.0 2
PA-1
CHEMBL614949
 IC50 4.33 4.33 46600.0 1
K562
CHEMBL385
 IC50 4.23 4.23 59200.0 1
SK-BR-3
CHEMBL613834
 IC50 4.17 4.17 67100.0 1
ES-2
CHEMBL5058622
 IC50 4.1 4.1 79000.0 1
SK-OV-3
CHEMBL614925
 IC50 4.05 4.05 89800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2500.0 ng.hr.mL-1 Mus musculus
AUC 4335.0 ng.hr.mL-1 Mus musculus
AUC 2710.0 ng.hr.mL-1 Mus musculus
AUC 4371.0 ng.hr.mL-1 Mus musculus
AUC 2719.0 ng.hr.mL-1 Mus musculus
CL 13.0 mL.min-1.kg-1 Mus musculus
CL 22.0 mL.min-1.kg-1 Mus musculus
CL 103.0 mL.min-1.g-1 Homo sapiens
CL 173.82 mL.min-1.g-1 Homo sapiens
CL 12.4 mL.min-1.kg-1 Mus musculus
CL 1718.2 mL.min-1.kg-1 Mus musculus
CL 346.9 mL.min-1.kg-1 Rattus norvegicus
CL 457.7 mL.min-1.kg-1 Canis lupus familiaris
CL 237.2 mL.min-1.kg-1 Macaca mulatta
CL 65.7 mL.min-1.kg-1 Homo sapiens
Cmax 3399.39 nM Mus musculus
Cmax 3516.37 nM Mus musculus
F 55.0 % Mus musculus
F 20.0 % Mus musculus
F 32.0 % Mus musculus
Fu 0.014 - Mus musculus
Ka 8.093 10^6/M/s Homo sapiens
Ka 8.84 10^5/M/s Homo sapiens
Ka 5.656 10^6/Ms Homo sapiens
Ka 4.49 10^5/M/s Homo sapiens
T1/2 1.6 hr Mus musculus
T1/2 0.3367 hr Homo sapiens
T1/2 0.1328 hr Homo sapiens
T1/2 0.88 hr Mus musculus
T1/2 0.59 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone-lysine N-methyltransferase EZH2 IC50 = 0.34 nM 9.47 Inhibition of wild type EZH2 (unknown origin) by AlphaLISA assay 31959420
Unchecked IC50 = 0.37 nM 9.43 Inhibition of EZH2 Y641F mutant (unknown origin) preincubated for 15 mins follow... 38640588
Unchecked IC50 = 0.85 nM 9.07 Inhibition of EZH2 Y641N mutant (unknown origin) preincubated for 15 mins follow... 38640588
Histone-lysine N-methyltransferase EZH2 IC50 = 1.0 nM 9.0 Inhibition of EZH2 (unknown origin) using biotinylated nucleosome, H3K27me3 acti... 26189078
Histone-lysine N-methyltransferase EZH2 IC50 = 1.0 nM 9.0 Inhibition of EZH2 Y641N mutant (unknown origin) using biotinylated nucleosome, ... 26189078
Histone-lysine N-methyltransferase EZH2 IC50 = 1.2 nM 8.92 Inhibition of human N-terminal His-tagged EZH2 (2 to end residues) using [3H]-SA... 37826933
Histone-lysine N-methyltransferase EZH2 IC50 = 1.2 nM 8.92 Inhibition of wild type EZH2 (unknown origin) preincubated for 15 mins followed ... 38640588
Histone-lysine N-methyltransferase EZH2 IC50 = 1.43 nM 8.85 Inhibition of EZH2 (unknown origin) 38580135
Histone-lysine N-methyltransferase EZH2 IC50 = 1.6 nM 8.8 Inhibition of EZH2 (unknown origin) 37956762
Histone-lysine N-methyltransferase EZH2 IC50 = 1.7 nM 8.77 Inhibition of EZH2 Y641F mutant (unknown origin) using [3H]-SAM as substrate pre... 37826933
Histone-lysine N-methyltransferase EZH2 IC50 = 1.9 nM 8.72 Inhibition of EZH2 A677G mutant (unknown origin) using [3H]-SAM as substrate pre... 37826933
Polycomb protein EED IC50 = 2.0 nM 8.7 Inhibition of recombinant N-terminal GST-tagged EED (76 to 441 residues) (unknow... 28092155
Histone-lysine N-methyltransferase EZH2 IC50 = 2.2 nM 8.66 Inhibition of EZH2 Y641N mutant (unknown origin) using [3H]-SAM as substrate pre... 37826933
Pfeiffer IC50 = 2.26 nM 8.65 Antiproliferative activity against human Pfeiffer cells harboring EZH2 A677G mut... 37956762
Histone-lysine N-methyltransferase EZH2 IC50 = 2.45 nM 8.61 Inhibitory Activity Assay: The inhibitory activity of the synthesized compounds ... -
Histone-lysine N-methyltransferase EZH2 IC50 = 2.5 nM 8.6 Inhibition of EZH2 Y641S mutant (unknown origin) using [3H]-SAM as substrate pre... 37826933
Unchecked Ki = 2.5 nM 8.6 Binding affinity to wild type human PRC2 assessed as inhibition constant 37156182
Histone-lysine N-methyltransferase EZH2 Ki = 2.5 nM 8.6 Binding affinity to Ezh2 (unknown origin) assessed as inhibition constant 36155354
Histone-lysine N-methyltransferase EZH2 Ki = 2.5 nM 8.6 Inhibition of PRC2 catalytic core EZH2 (unknown origin) 32871345
Histone-lysine N-methyltransferase EZH2 Ki = 2.5 nM 8.6 Inhibition of wild-type human EZH2 by flash plate assay 25406853

Literature References

PubMed DOI Target Context # Activities
37956762 10.1016/j.bmcl.2023.129558 ADMET 30
33606537 10.1021/acs.jmedchem.0c02234 Unchecked 26
25406853 10.1021/jm501234a Unchecked 15
32579914 10.1016/j.celrep.2020.107782 Medulloblastoma cell 12
27191993 10.18632/oncotarget.9371 Histone-lysine N-methyltransferase EZH2 10
34664960 10.1021/acs.jmedchem.1c01154 Histone-lysine N-methyltransferase EZH2 9
28246360 10.1128/mbio.00133-17 Human immunodeficiency virus 1 8
31476112 10.15252/emmm.201809930 Histone-lysine N-methyltransferase EZH2 7
28092155 10.1021/acs.jmedchem.6b01576 Mus musculus 7
32370249 10.3390/biology9050093 Mus musculus 7
38580135 10.1016/j.bmcl.2024.129726 A549 7
37826933 10.1016/j.ejmech.2023.115825 Histone-lysine N-methyltransferase EZH2 6
38580135 10.1016/j.bmcl.2024.129726 HeLa 6
36692394 10.1021/acs.jmedchem.2c01370 Histone-lysine N-methyltransferase EZH2 6
39196854 10.1021/acs.jmedchem.4c01250 CWR22R 5
34196564 10.1021/acs.jmedchem.1c00460 SU-DHL-6 5
38134746 10.1016/j.ejmech.2023.116054 Histone-lysine N-methyltransferase EZH2 4
26189078 10.1016/j.bmcl.2015.06.056 Plasma 4
25746006 10.1038/onc.2015.38 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4

Data from ChEMBL 36 via Core Engine