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Compound Detail

CHEMBL452231

TENIPOSIDE
💊 Approved Drug
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💊 Approved Drug
COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](c6cccs6)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 CHEMBL452231
Name TENIPOSIDE
Phase Approved
Structure Type MOL
InChI Key NRUKOCRGYNPUPR-QBPJDGROSA-N
Therapeutic ✓ Yes

Known Names

NSC-122819 Teniposide Teniposido VM-26 VM26 Vumon
16
Targets
22
Activities
1
Assay Types
5
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

Molecular Properties

656.7
MW (Da)
2.75
ALogP
14
HBA
3
HBD
160.8
PSA (Ų)
0.33
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1978

Extended Properties

Molecular Formula C32H32O13S
MW 656.66
Aromatic Rings 3
Heavy Atoms 46
NP-Likeness 1.36

Mechanism of Action

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

Indications

Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Leukemia Lymphoma

ATC Classification

L01CB02
teniposide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States

Activity Summary

IC50 22 meas. best 7.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 7.8 6.5533 15.8 3
PC-3
CHEMBL390
 IC50 7.8 7.8 15.8 1
A549
CHEMBL392
 IC50 7.8 6.445 15.8 2
CWR22R
CHEMBL612657
 IC50 7.09 7.09 82.0 1
RPMI 8402
CHEMBL612517
 IC50 6.66 6.6233 220.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.55 6.55 280.0 1
GLC4 cell line
CHEMBL612707
 IC50 6.32 5.935 480.0 2
HepG2
CHEMBL395
 IC50 5.37 5.37 4300.0 1
L02
CHEMBL4296457
 IC50 4.94 4.94 11500.0 1
MRC5
CHEMBL614181
 IC50 4.91 4.91 12200.0 1
HMEC
CHEMBL614734
 IC50 4.91 4.91 12400.0 1
HeLa
CHEMBL399
 IC50 4.83 4.83 14900.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 4.69 4.69 20600.0 1
Unchecked
CHEMBL612545
 IC50 4.65 4.65 22300.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.46 4.46 34900.0 1
DNA topoisomerase II
CHEMBL2094255
 IC50 4.2 4.2 62700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.19 mL.min-1.kg-1 Homo sapiens
CL 0.19 mL.min-1.kg-1 Homo sapiens
Fu 0.0044 - Homo sapiens
MRT 37.0 hr Homo sapiens
T1/2 16.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 15.8 nM 7.8 Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT ... 32992133
A549 IC50 = 15.8 nM 7.8 Antiproliferative activity against human A549 cells incubated for 72 hrs by MTT ... 32992133
PC-3 IC50 = 15.8 nM 7.8 Antiproliferative activity against human PC3 cells incubated for 72 hrs by MTT a... 32992133
CWR22R IC50 = 82.0 nM 7.09 Antiproliferative activity against human 22Rv1 cells after 96 hrs by propidium i... 26854430
MCF7 IC50 = 125.0 nM 6.9 Antiproliferative activity against human MCF7 cells after 96 hrs by propidium io... 26854430
RPMI 8402 IC50 = 220.0 nM 6.66 Cytotoxicity against human lymphoblast tumor cell line RPM18402 12392745
RPMI 8402 IC50 = 220.0 nM 6.66 Cytotoxic activity against human lymphoblast tumor cell line RPMI8402 after 4 da... 12747798
RPMI 8402 IC50 = 280.0 nM 6.55 Cytotoxicity using camptothecin-resistant variant of RPM18402 (CPT-K5) possessin... 12392745
NON-PROTEIN TARGET IC50 = 280.0 nM 6.55 Cytotoxic activity against human lymphoblast tumor cell line CPT-K5 after 4 days... 12747798
GLC4 cell line IC50 = 480.0 nM 6.32 Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using ... 7783142
GLC4 cell line IC50 = 2800.0 nM 5.55 Cytotoxic effect against GLC4 (human small cell lung carcinoma cell line) using ... 7783142
HepG2 IC50 = 4300.0 nM 5.37 Anticancer activity against human HepG2 cells assessed as inhibition of cell pro... 32084316
A549 IC50 = 8200.0 nM 5.09 Anticancer activity against human A549 cells assessed as inhibition of cell prol... 32084316
MCF7 IC50 = 11100.0 nM 4.96 Anticancer activity against human MCF7 cells assessed as inhibition of cell prol... 32084316
L02 IC50 = 11500.0 nM 4.94 Cytotoxicity against human HL7702 cells assessed as inhibition of cell prolifera... 32084316
MRC5 IC50 = 12200.0 nM 4.91 Cytotoxicity against human MRC5 cells assessed as inhibition of cell proliferati... 32084316
HMEC IC50 = 12400.0 nM 4.91 Cytotoxicity against human HMEC cells assessed as inhibition of cell proliferati... 32084316
HeLa IC50 = 14900.0 nM 4.83 Anticancer activity against human HeLa cells assessed as inhibition of cell prol... 32084316
ATP-binding cassette sub-family C member 3 IC50 = 20600.0 nM 4.69 Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... 23956101
Unchecked IC50 = 22300.0 nM 4.65 Cytotoxicity against human H8 cells assessed as inhibition of cell proliferation... 32084316

Literature References

PubMed DOI Target Context # Activities
21051535 10.1124/dmd.110.034629 ADMET 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32084316 10.1021/acs.jmedchem.9b01354 L02 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
32084316 10.1021/acs.jmedchem.9b01354 HepG2 7
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
20014752 10.1021/tx900326k Hepatotoxicity 3
32084316 10.1021/acs.jmedchem.9b01354 ADMET 2
19445515 10.1021/jm900403j Homo sapiens 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
8988604 10.1021/np960144k C6 2
32084316 10.1021/acs.jmedchem.9b01354 Unchecked 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
12392745 10.1016/s0960-894x(02)00737-0 RPMI 8402 2
7783142 10.1021/jm00012a010 GLC4 cell line 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2

Data from ChEMBL 36 via Core Engine