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Compound Detail

CHEMBL53463

DOXORUBICIN
💊 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 CHEMBL53463
Name DOXORUBICIN
Phase Approved
Structure Type MOL
InChI Key AOJJSUZBOXZQNB-TZSSRYMLSA-N
Therapeutic ✓ Yes

Known Names

Adriablastin Adriblastina Doxorubicin Doxorubicina Doxorubicine Epirubicin hydrochloride impurity, doxorubicin- Hydroxydaunorubicin NSC-123127 NSC-759155 Valrubicin impurity, doxorubicin
889
Targets
5,930
Activities
4
Assay Types
30
PK Parameters
20
Publications
10
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 1974
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -rubicin
USAN Year 1973

Extended Properties

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

Indications

Neoplasms Neoplasms Brain Neoplasms Brain Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma Carcinoma, Hepatocellular Choroid Plexus Neoplasms Desmoid Tumors Endometrial Neoplasms Endometrial Neoplasms Fallopian Tube Neoplasms Fallopian Tube Neoplasms Ganglioneuroblastoma Granuloma, Lethal Midline Hepatoblastoma Hodgkin Disease Hodgkin Disease

ATC Classification

L01DB01
doxorubicin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 5,829 meas. best 10.4
EC50 88 meas. best 8.05
Ki 9 meas. best 5.68
Kd 4 meas. best 7.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Chorioallantoic membrane
CHEMBL2367390
 IC50 10.4 8.9 0.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 10.33 6.2216 0.0 480
MKN-45
CHEMBL614354
 IC50 9.72 7.1183 0.2 6
KB
CHEMBL398
 IC50 9.64 6.631 0.2 77
MCF7
CHEMBL387
 IC50 9.53 6.0813 0.3 557
NCI-H460
CHEMBL396
 IC50 9.42 6.9934 0.4 58
NCI-H446
CHEMBL612440
 IC50 9.41 7.94 0.4 4
MDA-MB-231
CHEMBL400
 IC50 9.38 6.1931 0.4 220
A549
CHEMBL392
 IC50 9.0 6.1444 1.0 354
ACHN
CHEMBL614519
 IC50 9.0 6.8977 1.0 13
SK-MEL-2
CHEMBL614917
 IC50 9.0 7.5214 1.0 22
SK-OV-3
CHEMBL614925
 IC50 9.0 6.9089 1.0 63
HL-60
CHEMBL383
 IC50 8.95 7.012 1.1 111
A2780
CHEMBL614004
 IC50 8.92 7.2173 1.2 44
EOL1
CHEMBL614489
 IC50 8.9 8.23 1.3 2
A-431
CHEMBL614069
 IC50 8.87 7.0925 1.4 12
NTERA-2-cl-D1
CHEMBL614206
 IC50 8.86 8.86 1.4 1
EW-16
CHEMBL2366358
 IC50 8.72 8.72 1.9 1
HT-29
CHEMBL384
 IC50 8.7 6.3708 2.0 113
PC-3
CHEMBL390
 IC50 8.7 5.9007 2.0 132
MOLT-4
CHEMBL614177
 IC50 8.7 7.6693 2.0 15
HuTu80
CHEMBL614582
 IC50 8.67 7.685 2.1 2
Unchecked
CHEMBL612545
 IC50 8.6 5.9801 2.5 127
CCRF-CEM
CHEMBL382
 IC50 8.52 7.0516 3.0 45
MT4
CHEMBL388
 IC50 8.52 7.94 3.0 8
KS-1
CHEMBL2366228
 IC50 8.46 8.46 3.4 1
HT-144
CHEMBL2366291
 IC50 8.46 8.46 3.5 1
DU-145
CHEMBL613508
 IC50 8.41 5.9867 3.9 79
MFH-ino
CHEMBL2366262
 IC50 8.4 8.4 4.0 1
HOP-62
CHEMBL614643
 IC50 8.4 7.11 4.0 5
HeLa
CHEMBL399
 IC50 8.38 6.0958 4.2 268
U-937
CHEMBL612794
 IC50 8.35 6.9185 4.5 13
GOTO
CHEMBL2366179
 IC50 8.32 7.7267 4.7 3
DNA topoisomerase 2-alpha
CHEMBL1806
 IC50 8.31 6.2038 4.9 8
Fibroblast
CHEMBL5314315
 IC50 8.3 7.584 5.0 5
HCT-15
CHEMBL612263
 IC50 8.3 6.5909 5.0 46
MDA-MB-468
CHEMBL614335
 IC50 8.3 6.9938 5.0 8
LC-2-ad
CHEMBL2366260
 IC50 8.29 8.29 5.1 1
NB1
CHEMBL2366284
 IC50 8.29 7.9733 5.2 3
ADMET
CHEMBL612558
 IC50 8.29 6.2003 5.1 69
IMR-32
CHEMBL614585
 IC50 8.29 6.804 5.1 10
HT-1080
CHEMBL614580
 IC50 8.24 6.9587 5.8 15
SW982
CHEMBL2366238
 IC50 8.22 8.22 6.1 1
HCT-116
CHEMBL394
 IC50 8.22 6.2408 6.0 165
A2780cisR
CHEMBL614023
 IC50 8.22 7.995 6.0 2
KB 3-1
CHEMBL614590
 IC50 8.22 7.252 6.0 5
ES4
CHEMBL2366118
 IC50 8.21 8.21 6.1 1
SJSA-1
CHEMBL2366298
 IC50 8.21 7.58 6.2 2
K562
CHEMBL385
 IC50 8.21 6.3557 6.1 142
KGN
CHEMBL2366154
 IC50 8.2 8.2 6.3 1

Pharmacokinetic Data

Parameter Value Units Species
ALB_CHANGE - - Rattus norvegicus
AUC 1856.15 ng.hr.mL-1 Mus musculus
AUC 14.06 nmol.min.g-1 Mus musculus
AUC 8.697 nmol.min.g-1 Mus musculus
AUC 288.0 ug.ml-1 Canis lupus familiaris
AUC 1974.0 ng.hr.mL-1 Homo sapiens
AUC 11350.0 ng.hr.mL-1 Mus musculus
AUC 10370.0 ng.hr.mL-1 Mus musculus
CHOL_CHANGE - - Rattus norvegicus
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 13.2 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 17.0 mL.min-1.kg-1 Canis lupus familiaris
CL 17.0 mL.min-1.kg-1 Homo sapiens
CL 28.0 mL.min-1.kg-1 Macaca
CL 34.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.059 mL.min-1.kg-1 Canis lupus familiaris
CL 1.72 mL.min-1.kg-1 Canis lupus familiaris
CL 10.82 mL.min-1.kg-1 Rattus norvegicus
CL 3.68 mL.min-1.kg-1 Rattus norvegicus
CL 7.268 mL.min-1.kg-1 Homo sapiens
CL 2.035 mL.min-1.kg-1 Homo sapiens
Clp 607.0 ml.min-1 Canis lupus familiaris
Clp 15.0 ml.min-1 Canis lupus familiaris
CLp 57.0 L.h-1 Homo sapiens
Compound recovery - - Mus musculus
Compound recovery - - Mus musculus
Compound recovery - - Mus musculus
Compound recovery 2.08 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Chorioallantoic membrane IC50 = 0.04 nM 10.4 Antiangiogenic activity in fertile leghorn chicken egg Chorioallantoic membrane ... 24890652
NON-PROTEIN TARGET IC50 = 0.047 nM 10.33 Cytotoxicity against human MDA231 cells after 72 hrs by MTS assay 21142180
MKN-45 IC50 = 0.19 nM 9.72 Antiproliferative activity against human MKN45 cells after 72 hrs by methylene b... 21067930
KB IC50 = 0.23 nM 9.64 Antiproliferative activity against human KB cells after 72 hrs by methylene blue... 21067930
MCF7 IC50 = 0.294 nM 9.53 Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by... 26291039
NCI-H460 IC50 = 0.38 nM 9.42 Antiproliferative activity against human H460 cells after 72 hrs by methylene bl... 21067930
NCI-H446 IC50 = 0.39 nM 9.41 Antiproliferative activity against human NCI-H446 cells assessed as inhibition o... 35932565
NON-PROTEIN TARGET IC50 = 0.4 nM 9.4 Antiproliferative activity against human KB 3.1 cells after 72 hrs by MTT assay 17949859
MDA-MB-231 IC50 = 0.414 nM 9.38 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 5 d... 26291039
MCF7 IC50 = 0.7 nM 9.15 Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay 17949859
ACHN IC50 = 1.0 nM 9.0 Antiproliferative activity against human ACHN cell line by MTT assay 16913700
NON-PROTEIN TARGET IC50 = 1.0 nM 9.0 Cytotoxicity against human SK-MEL-2 cells assessed as reduction in cell prolifer... 27856237
SK-MEL-2 IC50 = 1.0 nM 9.0 Cytotoxicity against human SK-MEL-2 cells assessed as inhibition of cell growth ... 25981688
SK-MEL-2 IC50 = 1.0 nM 9.0 Cytotoxicity against human SK-MEL-2 cells assessed as cell growth inhibition aft... 25466198
SK-OV-3 IC50 = 1.0 nM 9.0 Cytotoxicity against human SKOV3 cells by SRB assay 20719504
A549 IC50 = 1.0 nM 9.0 Cytotoxicity against human A549 cells by SRB assay 22951040
KB IC50 = 1.0 nM 9.0 Cytotoxicity against human KB cells after 72 hrs by MTS assay 19655762
HL-60 IC50 = 1.13 nM 8.95 Cytotoxicity against human HL60 cells by MTT assay 19345581
HL-60 IC50 = 1.13 nM 8.95 Cytotoxicity against human HL60 cells after 3 days by MTT assay 20356655
A2780 IC50 = 1.2 nM 8.92 Cytotoxicity against human A2780 cells 21774499

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1385
- 10.6019/CHEMBL3885881 Rattus norvegicus 440
22867862 10.1124/dmd.112.046631 Rattus norvegicus 61
26142490 10.1016/j.ejmech.2015.06.044 ADMET 40
38810335 10.1016/j.ejmech.2024.116527 Ehrlich 26
34438013 10.1016/j.bmcl.2021.128337 ADMET 25
30025346 10.1016/j.ejmech.2018.07.021 Unchecked 23
37506545 10.1016/j.ejmech.2023.115675 HOP-92 22
31653441 10.1016/j.bmc.2019.115144 Unchecked 22
38642371 10.1021/acs.jmedchem.4c00239 Ehrlich 21
38117230 10.1021/acs.jmedchem.3c01708 Ehrlich 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
26948540 10.1016/j.bmcl.2016.02.072 MCF7 17
36395650 10.1016/j.ejmech.2022.114912 UO-31 17
37001390 10.1016/j.ejmech.2023.115304 ADMET 17
38784465 10.1039/d4md00015c HeLa 17
17993275 10.1016/j.bmcl.2007.10.069 NON-PROTEIN TARGET 17
21721528 10.1021/jm2006047 NIH3T3 15
2002471 10.1021/jm00107a007 Mus sp. 15
10579838 10.1021/jm9901226 Mus musculus 14

Data from ChEMBL 36 via Core Engine