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Compound Detail

CHEMBL359744

DOXORUBICIN HYDROCHLORIDE
💊 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.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL359744
Name DOXORUBICIN HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key MWWSFMDVAYGXBV-RUELKSSGSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL53463
Active Moiety CHEMBL53463

Known Names

Adriablastina cs Adriamycin Adriamycin pfs Adriamycin rdf Adriamycin, hydrochloride Caelyx Caelyx pegylated liposomal Celdoxome pegylated liposomal Doxil Doxil (liposomal) Doxorubicin citrate Doxorubicin citric acid salt +12 more
108
Targets
749
Activities
2
Assay Types
18
PK Parameters
20
Publications
24
Known Names
20
Indications
2
Mechanisms

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

Extended Properties

Molecular Formula C27H30ClNO11
MW 579.99
Aromatic Rings 2
Heavy Atoms 39
NP-Likeness 1.81

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA topoisomerase II alpha inhibitor INHIBITOR DNA topoisomerase 2-alpha ✓ ✓
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma Carcinoma Carcinoma, Ovarian Epithelial Carcinoma, Ovarian Epithelial Heart Failure Hodgkin Disease Hodgkin Disease Leukemia, Myelomonocytic, Acute Lymphoma, Non-Hodgkin Multiple Myeloma Osteosarcoma Osteosarcoma Ovarian Neoplasms Ovarian Neoplasms Ovarian Neoplasms Sarcoma

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
musculoskeletal toxicity
Country: United States

Activity Summary

IC50 738 meas. best 9.7
EC50 11 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ECa-109 cell line
CHEMBL614668
 IC50 9.7 9.7 0.2 1
Bel-7402
CHEMBL614279
 IC50 9.43 6.6211 0.4 9
HepG2
CHEMBL395
 IC50 9.35 6.2483 0.5 30
K562
CHEMBL385
 IC50 9.0 6.5215 1.0 40
MCF7
CHEMBL387
 IC50 8.92 5.9913 1.2 64
HCT-116
CHEMBL394
 IC50 8.92 6.4439 1.2 23
A549
CHEMBL392
 IC50 8.7 6.2274 2.0 61
MV4-11
CHEMBL613835
 IC50 8.22 7.8775 6.0 4
HT-1080
CHEMBL614580
 IC50 8.15 7.24 7.0 5
A-431
CHEMBL614069
 IC50 8.05 8.05 9.0 1
HL-60
CHEMBL383
 IC50 8.0 7.0741 10.0 27
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 5.8545 10.0 78
KB
CHEMBL398
 IC50 8.0 6.2764 10.0 11
BGC-823
CHEMBL614526
 IC50 8.0 6.3825 10.0 4
P388
CHEMBL389
 IC50 7.77 7.145 17.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.7 6.524 20.0 5
HeLa
CHEMBL399
 EC50 7.7 7.7 20.0 1
HT-1080
CHEMBL614580
 EC50 7.7 7.7 20.0 1
IMR-32
CHEMBL614585
 IC50 7.7 6.735 20.0 2
A549
CHEMBL392
 EC50 7.4 7.4 40.0 1
T47D
CHEMBL614361
 IC50 7.4 6.1089 40.0 18
Unchecked
CHEMBL612545
 IC50 7.37 5.4317 42.9 18
FHC
CHEMBL614654
 IC50 7.24 7.24 57.0 1
C6
CHEMBL614657
 IC50 7.22 7.22 60.0 1
ADMET
CHEMBL612558
 IC50 7.17 5.9125 68.0 4
MOLT-4
CHEMBL614177
 IC50 7.16 7.16 70.0 1
KG-1a
CHEMBL4296453
 IC50 7.1 7.1 80.0 1
WI-38
CHEMBL614391
 IC50 7.1 6.63 80.0 2
NCI-H187
CHEMBL2366276
 IC50 7.07 6.77 86.0 3
U-118-MG
CHEMBL1075602
 IC50 7.05 7.05 90.0 1
PC-3
CHEMBL390
 IC50 7.05 6.2813 90.0 15
SW-620
CHEMBL612262
 IC50 7.05 6.4767 90.0 3
NCI-H23
CHEMBL614997
 IC50 7.05 6.72 90.0 3
MDA-MB-231
CHEMBL400
 IC50 7.02 6.1058 96.0 36
HeLa
CHEMBL399
 IC50 7.0 6.049 100.0 50
U-87 MG
CHEMBL614247
 IC50 7.0 6.5078 100.0 9
SH-SY5Y
CHEMBL614910
 IC50 7.0 6.7667 100.0 3
LoVo
CHEMBL614721
 IC50 6.96 6.375 110.0 4
SW480
CHEMBL612544
 IC50 6.92 6.92 120.0 1
MKN-1
CHEMBL614352
 IC50 6.92 6.92 120.0 1
CCRF-CEM
CHEMBL382
 IC50 6.82 6.82 150.0 1
NUGC-3
CHEMBL614208
 IC50 6.82 6.82 150.0 1
MCF-10A
CHEMBL614321
 IC50 6.8 6.33 160.0 5
U-251
CHEMBL615022
 IC50 6.8 5.5525 157.0 4
HCT-15
CHEMBL612263
 IC50 6.77 5.935 170.0 16
ACHN
CHEMBL614519
 IC50 6.77 6.675 170.0 2
MGC-803
CHEMBL3706566
 IC50 6.7 6.1013 200.0 8
L02
CHEMBL4296457
 IC50 6.7 5.7933 200.0 6
ASPC1
CHEMBL612588
 IC50 6.7 6.35 200.0 6
NCI-H1975
CHEMBL614348
 IC50 6.7 6.4 200.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 324.0 mL/min/m2 Homo sapiens
CL 1088.0 mL/min/m2 Homo sapiens
CL 433.0 mL/min/m2 Homo sapiens
CL 1443.0 mL/min/m2 Homo sapiens
CL 1540.0 mL/min/m2 Homo sapiens
CL 813.0 mL/min/m2 Homo sapiens
Ka 27.1 10'-4/M Homo sapiens
Ka 7.45 10'-4/M Homo sapiens
Ka 4.19 10'-4/M Homo sapiens
Ka 3.26 10'-4/M Homo sapiens
PPB 75.0 % Homo sapiens
Ratio AUC 0.5 - Homo sapiens
T1/2 0.08333 hr Homo sapiens
T1/2 20.0 hr Homo sapiens
T1/2 54.0 hr Homo sapiens
T1/2 35.0 hr Homo sapiens
T1/2 23.0 hr Mus musculus
Vss 809.0 L/m2 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ECa-109 cell line IC50 = 0.201 nM 9.7 Cytotoxicity against human Eca-109 cells assessed as reduction in cell viability... 35152092
Bel-7402 IC50 = 0.369 nM 9.43 Cytotoxicity against human Bel-7402 cells assessed as reduction in cell viabilit... 35152092
HepG2 IC50 = 0.45 nM 9.35 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 35152092
K562 IC50 = 1.0 nM 9.0 Cytotoxicity against human K562 cells assessed as inhibition of cell growth incu... 36708676
HepG2 IC50 = 1.0 nM 9.0 Anticancer activity against human HepG2 cells assessed as inhibition of cell gro... 33940466
MCF7 IC50 = 1.2 nM 8.92 Anticancer activity against human MCF7 cells assessed as inhibition of cell grow... 33940466
HCT-116 IC50 = 1.2 nM 8.92 Anticancer activity against human HCT-116 cells assessed as inhibition of cell g... 33940466
A549 IC50 = 2.0 nM 8.7 Cytotoxicity against human A549 cells assessed as decrease in cell viability by ... 29489361
MV4-11 IC50 = 6.0 nM 8.22 Cytotoxicity against human MV4-11 cells assessed as cell viability after 72 hrs ... 24686018
MV4-11 IC50 = 6.0 nM 8.22 Antiproliferative activity against Homo sapiens (human) MV411 cells after 72 hr ... -
MV4-11 IC50 = 6.0 nM 8.22 Antiproliferative activity against human MV4-11 cells after 72 hrs by MTT assay 22748378
HT-1080 IC50 = 7.0 nM 8.15 Cytotoxicity against human HT-1080 cells assessed as inhibition of cell growth i... 37729693
HT-1080 IC50 = 8.0 nM 8.1 Cytotoxicity against human HT-1080 cells assessed as reduction in cell viability... 33774342
A-431 IC50 = 9.0 nM 8.05 Cytotoxicity against human A-431 cells assessed as inhibition of cell growth inc... 37729693
K562 IC50 = 10.0 nM 8.0 Antiproliferative activity against human K562 cells after 48 hrs 17973361
K562 IC50 = 10.0 nM 8.0 Antiproliferative activity against human K562 cells after 48 hrs 20537765
K562 IC50 = 10.0 nM 8.0 Antiproliferative activity against human K562 cells after 48 hrs by Alamar blue ... 28045256
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Cytotoxicity against human HCT116 cells assessed as inhibition of cell growth af... -
BGC-823 IC50 = 10.0 nM 8.0 Cytotoxicity against human BGC823 cells after 48 hrs by MTT assay 23131338
HL-60 IC50 = 10.0 nM 8.0 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 15387667

Literature References

PubMed DOI Target Context # Activities
20133021 10.1016/j.ejmech.2010.01.037 HL-60 15
27499368 10.1016/j.bmc.2016.07.056 HeLa 12
30739827 10.1016/j.ejmech.2019.01.070 SMMC-7721 9
20133021 10.1016/j.ejmech.2010.01.037 NON-PROTEIN TARGET 9
20133021 10.1016/j.ejmech.2010.01.037 518A2 8
21862329 10.1016/j.bmcl.2011.07.066 Serotransferrin 8
6716401 10.1021/jm00371a014 Mus musculus 7
26994845 10.1016/j.ejmech.2016.02.061 NCI-H226 7
27120394 10.1021/acs.jmedchem.6b00184 H9c2 7
28188067 10.1016/j.bmcl.2016.08.032 HeLa 7
27499368 10.1016/j.bmc.2016.07.056 MCF7 7
26994845 10.1016/j.ejmech.2016.02.061 MDA-MB-468 7
- 10.1007/s00044-013-0486-7 HeLa 7
26994845 10.1016/j.ejmech.2016.02.061 MDA-MB-435 7
- 10.1007/s00044-011-9688-z MCF7 7
26994845 10.1016/j.ejmech.2016.02.061 MCF7 7
28803046 10.1016/j.ejmech.2017.07.056 MCF7 7
36780419 10.1021/acs.jmedchem.2c01862 ADMET 6
30530194 10.1016/j.ejmech.2018.11.070 Unchecked 6
27643560 10.1016/j.ejmech.2016.09.019 NON-PROTEIN TARGET 6

Data from ChEMBL 36 via Core Engine