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Compound Detail

CHEMBL46286

OMACETAXINE MEPESUCCINATE
💊 Approved Drug
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💊 Approved Drug
COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@@H]1C(OC)=C[C@]23CCCN2CCc2cc4c(cc2[C@H]13)OCO4

Basic Information

ChEMBL ID CHEMBL46286
Name OMACETAXINE MEPESUCCINATE
Phase Approved
Structure Type MOL
InChI Key HYFHYPWGAURHIV-JFIAXGOJSA-N
Therapeutic ✓ Yes

Known Names

Ceflatonin CGX-635 Homoharringtonin HOMOHARRINGTONINE Mepesuccinate d'omacetaxine Mepesuccinato de omacetaxina Myelostat NSC-141633 Omacetaxine mepesuccinate Omapro Synribo
25
Targets
36
Activities
3
Assay Types
0
PK Parameters
20
Publications
11
Known Names
6
Indications
1
Mechanisms

Molecular Properties

545.6
MW (Da)
2.58
ALogP
10
HBA
2
HBD
124.0
PSA (Ų)
0.45
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product First in Class
USAN Year 2007

Extended Properties

Molecular Formula C29H39NO9
MW 545.63
Aromatic Rings 1
Heavy Atoms 39
NP-Likeness 2.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Protein synthesis inhibitor - -

Indications

Neoplasms Neoplasms Leukemia Leukemia, Myeloid, Acute Leukemia, Myelogenous, Chronic, BCR-ABL Positive Myelodysplastic Syndromes

ATC Classification

L01XX40
omacetaxine mepesuccinate
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 32 meas. best 9.06
EC50 3 meas. best 8.31
Kd 1 meas. best 4.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
IC50 9.06 9.06 0.9 1
A204
CHEMBL614514
IC50 8.4 8.4 4.0 1
KB
CHEMBL398
IC50 8.4 8.4 4.0 1
BJ
CHEMBL614358
EC50 8.31 8.31 4.9 1
MV4-11
CHEMBL613835
IC50 8.3 8.3 5.0 1
OCI-Ly3
CHEMBL4523565
IC50 8.3 8.3 5.0 1
MOLT-4
CHEMBL614177
IC50 8.15 8.15 7.0 1
U-937
CHEMBL612794
IC50 7.92 7.92 12.0 1
HL-60
CHEMBL383
IC50 7.89 7.7367 13.0 3
HCT-116
CHEMBL394
IC50 7.89 7.89 13.0 1
K562
CHEMBL385
IC50 7.85 7.765 14.0 2
Unchecked
CHEMBL612545
IC50 7.74 7.74 18.3 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 7.7 6.995 20.0 2
MDA-MB-453
CHEMBL614334
IC50 7.68 7.68 21.0 1
NCI-H1299
CHEMBL612255
IC50 7.66 7.66 22.0 1
NCI-H1975
CHEMBL614348
IC50 7.66 7.66 22.0 1
A549
CHEMBL392
IC50 7.52 7.51 30.0 2
HepG2
CHEMBL395
IC50 7.46 7.46 34.5 1
Huh-7
CHEMBL614039
IC50 7.4 7.4 40.0 1
SARS-CoV-2
CHEMBL4303835
EC50 7.22 6.45 60.0 2
4T1
CHEMBL612589
IC50 7.22 7.22 60.0 1
L02
CHEMBL4296457
IC50 7.19 7.19 64.0 1
NCI-H716
CHEMBL2366106
IC50 7.19 7.19 65.0 1
BaF3
CHEMBL614524
IC50 7.09 7.09 81.0 1
HeLa
CHEMBL399
IC50 6.4 6.085 400.0 2
SARS-CoV-2
CHEMBL4303835
IC50 5.33 5.33 4710.0 1
Unchecked
CHEMBL612545
Kd 4.77 4.77 16970.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 0.87 nM 9.06 Cytotoxicity against human MCF7 cells assessed as reduction in protein synthesis 28850227
KB IC50 = 4.0 nM 8.4 Cytotoxicity against human KB cells assessed as reduction of cell growth by SRB ... 18782668
A204 IC50 = 4.0 nM 8.4 Antiproliferative activity against human A204 cells assessed as inhibition of ce... 36242991
BJ EC50 = 4.88 nM 8.31 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Dose Response to Characterize Compound... -
MV4-11 IC50 = 5.0 nM 8.3 Antiproliferative activity against human MV4-11 cells assessed as inhibition of ... 36242991
OCI-Ly3 IC50 = 5.0 nM 8.3 Antiproliferative activity against human OCILY3 cells assessed as inhibition of ... 36242991
MOLT-4 IC50 = 7.0 nM 8.15 Antiproliferative activity against human MOLT-4 cells assessed as inhibition of ... 36242991
U-937 IC50 = 12.0 nM 7.92 Antiproliferative activity against human U-937 cells assessed as inhibition of c... 36242991
HCT-116 IC50 = 13.0 nM 7.89 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 36242991
HL-60 IC50 = 13.0 nM 7.89 Antiproliferative activity against human HL-60 cells assessed as inhibition of c... 36242991
K562 IC50 = 14.0 nM 7.85 Antiproliferative activity against human K562 cells assessed as inhibition of ce... 36242991
Unchecked IC50 = 18.28 nM 7.74 Inhibition of Nuclear factor erythroid 2-related factor 2 5'-untranslated region... 31270017
NON-PROTEIN TARGET IC50 = 20.0 nM 7.7 Cytotoxicity against human HL60 cells assessed as growth inhibition after 72 hrs... -
MDA-MB-453 IC50 = 21.0 nM 7.68 Antiproliferative activity against human MDA-MB-453 cells assessed as inhibition... 36242991
K562 IC50 = 21.0 nM 7.68 Antiproliferative activity against human K562 cells assessed as inhibition of ce... 36155354
HL-60 IC50 = 22.0 nM 7.66 Antiproliferative activity against human HL60 cells after 62 hrs by MTS assay 29286665
HL-60 IC50 = 21.8 nM 7.66 Antiproliferative activity against human HL-60 cells assessed as inhibition of c... 35148094
NCI-H1975 IC50 = 22.0 nM 7.66 Antiproliferative activity against human NCI-H1975 cells assessed as inhibition ... 36242991
NCI-H1299 IC50 = 22.0 nM 7.66 Antiproliferative activity against human NCI-H1299 cells assessed as inhibition ... 36242991
A549 IC50 = 30.0 nM 7.52 Cytotoxicity against human A549 cells assessed as reduction of cell growth by SR... 18782668

Literature References

PubMed DOI Target Context # Activities
31270017 10.1016/j.bmcl.2019.06.049 Unchecked 19
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
7161602 10.1021/np50024a005 Agrobacterium tumefaciens 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20014752 10.1021/tx900326k Hepatotoxicity 3
7707309 10.1021/jm00007a003 Unchecked 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
19209890 10.1021/np8006217 L1210 1
36155354 10.1016/j.ejmech.2022.114742 K562 1
18782668 10.1016/j.bmcl.2008.08.050 A549 1
7161602 10.1021/np50024a005 P388 1
1710653 10.1021/np50073a012 Human immunodeficiency virus type 1 reverse transcriptase 1

Data from ChEMBL 36 via Core Engine