Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL44657

ETOPOSIDE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL44657
Name ETOPOSIDE
Phase Approved
Structure Type MOL
InChI Key VJJPUSNTGOMMGY-MRVIYFEKSA-N
Therapeutic ✓ Yes

Known Names

Etoposide Etoposide resolution mixture Etoposido Etoposidum NSC-141540 Sintopozid Toposar Vepesid VP-16-213
694
Targets
2,290
Activities
4
Assay Types
25
PK Parameters
20
Publications
9
Known Names
20
Indications
1
Mechanisms

Molecular Properties

588.6
MW (Da)
1.34
ALogP
13
HBA
3
HBD
160.8
PSA (Ų)
0.43
QED
2
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1983
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1978

Extended Properties

Molecular Formula C29H32O13
MW 588.56
Aromatic Rings 2
Heavy Atoms 42
NP-Likeness 1.89

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA topoisomerase II inhibitor INHIBITOR DNA topoisomerase II ✓ ✓

Indications

Carcinoma, Small Cell Lung Neoplasms Lung Neoplasms Neoplasms Neoplasms Small Cell Lung Carcinoma Adenocarcinoma of Lung Adrenal Cortex Neoplasms Anemia, Refractory Anemia, Refractory, with Excess of Blasts Brain Neoplasms Brain Neoplasms Breast Neoplasms Burkitt Lymphoma Carcinoma Carcinoma, Embryonal Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Central Nervous System Neoplasms Choriocarcinoma

ATC Classification

L01CB01
etoposide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 2,269 meas. best 9.0
EC50 15 meas. best 6.68
Ki 4 meas. best 4.87
Kd 2 meas. best 4.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DU-145
CHEMBL613508
 IC50 9.0 5.5885 1.0 62
CCRF-CEM
CHEMBL382
 IC50 8.7 6.5256 2.0 9
A549
CHEMBL392
 IC50 8.59 5.5543 2.6 141
KB
CHEMBL398
 IC50 8.34 5.664 4.6 40
HeLa
CHEMBL399
 IC50 8.24 5.3477 5.7 105
MCF7
CHEMBL387
 IC50 8.1 5.3776 8.0 103
P388
CHEMBL389
 IC50 8.0 6.8854 10.0 13
PC-3
CHEMBL390
 IC50 7.8 5.1922 15.8 27
RH-1
CHEMBL2366078
 IC50 7.75 7.75 17.8 1
NCI-H446
CHEMBL612440
 IC50 7.75 6.9525 17.6 4
A253 cell line
CHEMBL614255
 IC50 7.73 7.73 18.4 1
HT-144
CHEMBL2366291
 IC50 7.7 7.7 20.1 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.7 5.6604 20.0 181
EW-16
CHEMBL2366358
 IC50 7.67 7.67 21.5 1
HL-60
CHEMBL383
 IC50 7.6 6.1881 25.0 68
NTERA-2-cl-D1
CHEMBL614206
 IC50 7.6 7.6 25.0 1
MOLT-3
CHEMBL614176
 IC50 7.52 7.3475 30.0 4
MOLT-4
CHEMBL614177
 IC50 7.42 6.9 38.0 2
Unchecked
CHEMBL612545
 IC50 7.4 5.1283 40.0 29
KE-37
CHEMBL2366287
 IC50 7.39 7.39 40.7 1
SK-UT-1
CHEMBL2366316
 IC50 7.37 7.37 42.4 1
OCUB-M
CHEMBL2366121
 IC50 7.35 7.35 44.5 1
8-MG-BA
CHEMBL2366115
 IC50 7.33 7.33 46.9 1
TE-9
CHEMBL2366147
 IC50 7.25 7.25 55.9 1
CGTH-W-1
CHEMBL2366300
 IC50 7.24 7.24 57.4 1
SK-HEP1
CHEMBL614912
 IC50 7.21 6.2607 62.0 14
BB30-HNC
CHEMBL2366271
 IC50 7.19 7.19 64.2 1
DNA topoisomerase 2-beta
CHEMBL3396
 IC50 7.16 5.53 69.8 4
SW480
CHEMBL612544
 IC50 7.16 5.7587 70.0 15
A2780
CHEMBL614004
 IC50 7.16 5.77 70.0 3
ACN
CHEMBL2366195
 IC50 7.1 7.1 79.0 1
Bel-7402
CHEMBL614279
 IC50 7.1 6.27 80.0 3
SGC-7901
CHEMBL614909
 IC50 7.1 5.7667 80.0 3
NCI-H647
CHEMBL614999
 IC50 7.1 7.1 80.0 1
EW-13
CHEMBL2366124
 IC50 7.05 7.05 88.8 1
MT4
CHEMBL388
 IC50 7.05 6.2833 90.0 3
NCI-H460
CHEMBL396
 IC50 7.05 6.5667 90.0 9
TERT-RPE1
CHEMBL615013
 IC50 7.05 6.845 90.0 2
DU-4475
CHEMBL2366246
 IC50 7.02 7.02 96.2 1
ADMET
CHEMBL612558
 IC50 7.0 5.4121 100.0 19
T47D
CHEMBL614361
 IC50 7.0 5.5794 100.0 32
CCRF-SB
CHEMBL614542
 IC50 7.0 7.0 100.0 2
HGC-27
CHEMBL1075463
 IC50 6.99 6.99 102.1 1
A-427
CHEMBL614515
 IC50 6.99 6.94 103.4 2
HT-1080
CHEMBL614580
 IC50 6.96 6.396 108.5 5
MC-IXC
CHEMBL1075495
 IC50 6.94 6.94 115.1 1
MRK-nu-1
CHEMBL2366325
 IC50 6.93 6.93 116.2 1
EW-7
CHEMBL2366112
 IC50 6.9 6.9 125.1 1
B16
CHEMBL381
 IC50 6.89 6.0967 130.0 6
SW982
CHEMBL2366238
 IC50 6.88 6.88 130.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 933.0 ng.hr.mL-1 Rattus norvegicus
AUC 6825.47 ng.hr.mL-1 Mus musculus
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 19.0 mL.min-1.kg-1 Homo sapiens
CL 66.0 mL.min-1.g-1 Mus musculus
CL 7.0 mL.min-1.kg-1 Mus musculus
Cmax 30090.39 nM Mus musculus
F 52.0 % Homo sapiens
Fu 0.12 - Homo sapiens
Fu 0.12 - Homo sapiens
Fu 0.049 - Homo sapiens
Fu 0.63 - Canis lupus familiaris
Fu 0.52 - Rattus norvegicus
Fu 0.357 - Rattus norvegicus
Fu 0.539 - Rattus norvegicus
MRT 6.0 hr Homo sapiens
T1/2 5.7 hr Homo sapiens
T1/2 0.75 hr Mus musculus
T1/2 0.35 hr Mus musculus
T1/2 2.88 hr -
T1/2 27.72 hr -
Tmax 0.08333 hr Mus musculus
Vd 0.432 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DU-145 IC50 = 1.0 nM 9.0 Cytotoxicity against human DU145 cells after 4 days by CCK-8 assay 25062006
CCRF-CEM IC50 = 2.0 nM 8.7 Tested for the inhibitory activity against CCRF CEM T- cell leukemia cells 7932571
A549 IC50 = 2.56 nM 8.59 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 21145139
KB IC50 = 4.61 nM 8.34 Cytotoxicity against human KB cells after 72 hrs by MTT assay 21145139
HeLa IC50 = 5.7 nM 8.24 Cytotoxicity against human HeLa cells by MTT assay 24422592
MCF7 IC50 = 8.0 nM 8.1 Anticancer activity against human MCF7 cells by MTT assay -
P388 IC50 = 10.0 nM 8.0 Cytotoxicity against P388 leukemia 8389875
PC-3 IC50 = 15.8 nM 7.8 Antiproliferative activity against human PC3 cells incubated for 72 hrs by MTT a... 32992133
A549 IC50 = 15.8 nM 7.8 Antiproliferative activity against human A549 cells incubated for 72 hrs by MTT ... 32992133
MCF7 IC50 = 15.8 nM 7.8 Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT ... 32992133
NCI-H446 IC50 = 17.59 nM 7.75 Antiproliferative activity against human NCI-H446 cells assessed as inhibition o... 35932565
RH-1 IC50 = 17.78 nM 7.75 SANGER: Inhibition of human RH-1 cell growth in a cell viability assay. -
A253 cell line IC50 = 18.43 nM 7.73 SANGER: Inhibition of human A253 cell growth in a cell viability assay. -
HT-144 IC50 = 20.09 nM 7.7 SANGER: Inhibition of human HT-144 cell growth in a cell viability assay. -
NON-PROTEIN TARGET IC50 = 20.0 nM 7.7 Antiproliferative activity against human DU145 cells after 72 hrs by CCK8 assay 27643560
NON-PROTEIN TARGET IC50 = 20.0 nM 7.7 Cytotoxicity against human MOLT3 cells -
NON-PROTEIN TARGET IC50 = 20.2 nM 7.7 Cytotoxicity against human 95-D cells after 72 hrs by MTT assay 21145139
EW-16 IC50 = 21.48 nM 7.67 SANGER: Inhibition of human EW-16 cell growth in a cell viability assay. -
HL-60 IC50 = 25.0 nM 7.6 Tested for the cytostatic activity as inhibitory concentration against leukemia ... -
NON-PROTEIN TARGET IC50 = 25.0 nM 7.6 Inhibitory concentration to reduce cell number to 50% of Murine P388 leukemia ce... 9207945

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1481
- 10.6019/CHEMBL3885881 Rattus norvegicus 766
30878833 10.1016/j.ejmech.2019.03.006 MCF7 63
35231830 10.1016/j.ejmech.2022.114196 MCF7 29
30471828 10.1016/j.bmc.2018.11.014 MDA-MB-231 22
21051535 10.1124/dmd.110.034629 ADMET 21
22364746 10.1016/j.bmc.2012.01.039 COLO 205 20
35231830 10.1016/j.ejmech.2022.114196 SW480 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
10395485 10.1021/jm990055f Mus musculus 17
35231830 10.1016/j.ejmech.2022.114196 NCI-H1299 16
23999041 10.1016/j.bmcl.2013.07.068 MCF7 16
10509925 10.1016/s0960-894x(99)00472-2 Mus musculus 16
34678573 10.1016/j.ejmech.2021.113916 ADMET 16
23182091 10.1016/j.bmcl.2012.10.099 A549 15
26183545 10.1016/j.bmc.2015.06.049 DNA topoisomerase 2-alpha 14
11356111 10.1021/jm0005149 Mus musculus 14
27654394 10.1016/j.ejmech.2016.09.004 Molecular identity unknown 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
36063665 10.1016/j.ejmech.2022.114706 ADMET 14

Data from ChEMBL 36 via Core Engine