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Compound Detail

CHEMBL417

EPIRUBICIN
💊 Approved Drug
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💊 Approved Drug
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL417
Name EPIRUBICIN
Phase Approved
Structure Type MOL
InChI Key AOJJSUZBOXZQNB-VTZDEGQISA-N
Therapeutic ✓ Yes

Known Names

4'-epi-adriamycin Epiadriamycin Epidoxorubicin Epirubicin Epirubicina Epirubicine Farmorubicin NSC-256942
30
Targets
83
Activities
3
Assay Types
30
PK Parameters
20
Publications
8
Known Names
20
Indications

Molecular Properties

543.5
MW (Da)
0.00
ALogP
12
HBA
6
HBD
206.1
PSA (Ų)
0.24
QED
3
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -rubicin
USAN Year 1984

Extended Properties

Molecular Formula C27H29NO11
MW 543.53
Aromatic Rings 2
Heavy Atoms 39
NP-Likeness 1.81

Indications

Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Hepatocellular Inflammatory Breast Neoplasms Lymphoma, Large B-Cell, Diffuse Lymphoma, T-Cell, Peripheral Nasopharyngeal Carcinoma Sarcoma Stomach Neoplasms Stomach Neoplasms Thrombosis Triple Negative Breast Neoplasms Urinary Bladder Neoplasms Adenocarcinoma Carcinoma, Non-Small-Cell Lung Esophageal Neoplasms Hodgkin Disease Lymphoma, Follicular Lymphoma, Non-Hodgkin

ATC Classification

L01DB03
epirubicin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 81 meas. best 8.52
Kd 1 meas. best 7.62
Ki 1 meas. best 5.88

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DNA topoisomerase 2-alpha
CHEMBL1806
 IC50 8.52 8.52 3.0 1
NCI-H460
CHEMBL396
 IC50 7.7 7.19 20.0 4
Unchecked
CHEMBL612545
 Kd 7.62 7.62 24.0 1
MCF-10A
CHEMBL614321
 IC50 7.0 6.945 100.0 2
HepG2
CHEMBL395
 IC50 7.0 6.128 100.0 5
MDA-MB-231
CHEMBL400
 IC50 6.82 5.858 150.0 5
MCF7
CHEMBL387
 IC50 6.7 6.13 200.0 3
MDA-MB-435
CHEMBL614697
 IC50 6.64 6.49 230.0 4
K562
CHEMBL385
 IC50 6.62 6.2267 239.0 3
HCT-116
CHEMBL394
 IC50 6.43 6.3375 370.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.38 6.1071 420.0 7
PC-3
CHEMBL390
 IC50 6.34 5.615 460.0 4
SK-OV-3
CHEMBL614925
 IC50 6.3 6.3 498.0 1
MIA PaCa-2
CHEMBL614725
 IC50 6.3 6.3 500.0 1
Huh-7
CHEMBL614039
 IC50 6.3 5.67 495.0 2
NCI/ADR-RES
CHEMBL613829
 IC50 6.2 6.2 630.0 2
NS3
CHEMBL1293269
 IC50 6.12 6.12 750.0 1
A549
CHEMBL392
 IC50 6.09 5.6633 820.0 3
T-24
CHEMBL614774
 IC50 5.95 5.95 1120.0 1
MGC-803
CHEMBL3706566
 IC50 5.92 5.92 1200.0 1
A2780
CHEMBL614004
 IC50 5.89 5.89 1277.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
 Ki 5.88 5.88 1323.0 1
DU-145
CHEMBL613508
 IC50 5.7 5.35 2010.0 2
L02
CHEMBL4296457
 IC50 5.68 5.68 2100.0 1
SNB-19
CHEMBL614164
 IC50 5.64 5.64 2300.0 1
HT-29
CHEMBL384
 IC50 5.47 5.47 3360.0 1
NIH3T3
CHEMBL614822
 IC50 5.38 5.38 4200.0 1
T47D
CHEMBL614361
 IC50 5.37 5.37 4300.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
 IC50 5.29 5.29 5181.0 1
SGC-7901
CHEMBL614909
 IC50 5.29 5.29 5160.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
 IC50 5.1 5.1 7935.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 20.0 mL.min-1.kg-1 Homo sapiens
Fu 0.25 - Homo sapiens
MRT 38.0 hr Homo sapiens
PPB 80.7 % Rattus norvegicus
PPB 85.6 % Rattus norvegicus
PPB 88.2 % Rattus norvegicus
PPB 81.7 % Rattus norvegicus
PPB 81.0 % Rattus norvegicus
PPB 82.2 % Rattus norvegicus
PPB - % Homo sapiens
PPB 78.09 % Homo sapiens
PPB 77.35 % Homo sapiens
PPB 76.78 % Homo sapiens
PPB 76.52 % Mus musculus
PPB 79.89 % Mus musculus
PPB 79.96 % Mus musculus
PPB 80.35 % Mus musculus
PPB 79.06 % Rattus norvegicus
PPB 82.76 % Rattus norvegicus
PPB 81.27 % Rattus norvegicus
PPB 78.67 % Rattus norvegicus
PPB 78.46 % Oryctolagus cuniculus
PPB 70.17 % Oryctolagus cuniculus
PPB 78.4 % Oryctolagus cuniculus
PPB 77.06 % Oryctolagus cuniculus
PPB 80.32 % Canis lupus familiaris
PPB 81.22 % Canis lupus familiaris
PPB 80.68 % Canis lupus familiaris
PPB 80.9 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DNA topoisomerase 2-alpha IC50 = 3.0 nM 8.52 Inhibition of Topo IIalpha (unknown origin) 37847948
NCI-H460 IC50 = 20.0 nM 7.7 Cytotoxicity against human NCI-H460 cells after 48 hrs by MTT assay 29767975
Unchecked Kd = 24.0 nM 7.62 Binding affinity to pre-miR-21 (unknown origin) at A bulge assessed as dissociat... 31931338
NCI-H460 IC50 = 60.0 nM 7.22 Cytotoxicity against human NCI-H460 cells assessed as inhibition of cell prolife... 34852194
HepG2 IC50 = 100.0 nM 7.0 Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay 29767975
MCF-10A IC50 = 100.0 nM 7.0 Cytotoxicity against human MCF10A cells after 48 hrs by MTT assay 29767975
NCI-H460 IC50 = 120.0 nM 6.92 Cytotoxicity in human NCI-H460 cells assessed as reduction in cell viability inc... 31251621
NCI-H460 IC50 = 120.0 nM 6.92 Cytotoxicity against human NCI-H460 cells assessed as growth inhibition after 48... 28119026
MCF-10A IC50 = 130.0 nM 6.89 Cytotoxicity against human MCF10A cells assessed as growth inhibition after 48 h... 28119026
MDA-MB-231 IC50 = 150.0 nM 6.82 Antiproliferative activity against human MDA-MB-231 cells assessed as cell viabi... 33139111
MCF7 IC50 = 200.0 nM 6.7 Compound was tested for its toxicity against human breast cancer cells(MCF-7) 9548820
MDA-MB-435 IC50 = 230.0 nM 6.64 Cytotoxicity against human MDA-MB-435 cells assessed as inhibition of cell proli... 34852194
K562 IC50 = 239.0 nM 6.62 Cytotoxicity against human K562 cells incubated for 2 hrs followed by compound w... 39088428
MDA-MB-435 IC50 = 260.0 nM 6.58 Cytotoxicity against human MDA-MB-435 cells assessed as growth inhibition after ... 28119026
MDA-MB-435 IC50 = 260.0 nM 6.58 Cytotoxicity in human MDA-MB-435 cells assessed as reduction in cell viability i... 31251621
HepG2 IC50 = 320.0 nM 6.5 Cytotoxicity against human HepG2 cells assessed as growth inhibition after 48 hr... 28119026
HCT-116 IC50 = 370.0 nM 6.43 Cytotoxicity against human HCT116 cells assessed as growth inhibition after 48 h... 28119026
HCT-116 IC50 = 370.0 nM 6.43 Cytotoxicity in human HCT116 cells assessed as reduction in cell viability incub... 31251621
HCT-116 IC50 = 400.0 nM 6.4 Cytotoxicity against human HCT116 cells after 48 hrs by MTT assay 29767975
NON-PROTEIN TARGET IC50 = 420.0 nM 6.38 Cytotoxicity against human HeLa cells assessed as decrease in cell viability aft... 27560695

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 492
31685331 10.1016/j.bmc.2019.115131 quadruplex DNA 54
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
39088428 10.1021/acs.jmedchem.4c00614 ADMET 6
27560695 10.1021/acs.jnatprod.6b00639 NON-PROTEIN TARGET 5
26881291 10.1021/acs.jmedchem.5b01956 NCI/ADR-RES 4
19285415 10.1016/j.bmc.2009.02.032 Nucleic Acid 4
39088428 10.1021/acs.jmedchem.4c00614 K562 4
18426954 10.1124/dmd.108.020479 ADMET 4
31761381 10.1016/j.ejmech.2019.111851 MGC-803 3
26881291 10.1021/acs.jmedchem.5b01956 DNA 3
20014752 10.1021/tx900326k Hepatotoxicity 3
26881291 10.1021/acs.jmedchem.5b01956 MIA PaCa-2 3
39044437 10.1021/acs.jmedchem.4c01070 MDA-MB-231 3
19481462 10.1016/j.bmc.2009.05.007 NON-PROTEIN TARGET 3
31447082 10.1016/j.bmcl.2019.126631 C6 3
29903662 10.1016/j.bmcl.2018.05.033 SGC-7901 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
31685331 10.1016/j.bmc.2019.115131 Unchecked 2

Data from ChEMBL 36 via Core Engine