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Compound Detail

CHEMBL1563

DAUNORUBICIN HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)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 CHEMBL1563
Name DAUNORUBICIN HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key GUGHGUXZJWAIAS-QQYBVWGSSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL178
Active Moiety CHEMBL178

Known Names

Cerubidine Daunorubicin (as hydrochloride) Daunorubicin hcl Daunorubicin hydrochloride FI 6339 HYDROCHLORIDE FI 6339 [AS THE BASE] FI-6339 HYDROCHLORIDE NDC 0082-4155 NDC-0082-4155 NSC-82151 RP 13057 HYDROCHLORIDE RP 13057 [AS THE BASE) +1 more
29
Targets
43
Activities
1
Assay Types
0
PK Parameters
20
Publications
13
Known Names
20
Indications
2
Mechanisms

Molecular Properties

527.5
MW (Da)
1.03
ALogP
11
HBA
5
HBD
185.8
PSA (Ų)
0.31
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1979
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -rubicin
USAN Year 1976

Extended Properties

Molecular Formula C27H30ClNO10
MW 563.99
Aromatic Rings 2
Heavy Atoms 38
NP-Likeness 1.75

Mechanism of Action

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

Indications

Leukemia, Lymphoid Anemia, Refractory Anemia, Refractory, with Excess of Blasts Leukemia Leukemia, Basophilic, Acute Leukemia, Biphenotypic, Acute Leukemia, Biphenotypic, Acute Leukemia, Erythroblastic, Acute Leukemia, Megakaryoblastic, Acute Leukemia, Monocytic, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myeloid, Acute Leukemia, Myelomonocytic, Acute Leukemia, Myelomonocytic, Chronic Leukemia, Promyelocytic, Acute Lymphoma Myelodysplastic Syndromes Myeloproliferative Disorders Precursor Cell Lymphoblastic Leukemia-Lymphoma

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 43 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MOLT-4
CHEMBL614177
 IC50 9.0 9.0 1.0 1
P388
CHEMBL389
 IC50 8.52 7.465 3.0 2
K562
CHEMBL385
 IC50 7.82 7.82 15.0 1
L1210 (1565)
CHEMBL614000
 IC50 7.8 7.315 16.0 2
HL-60
CHEMBL383
 IC50 7.01 7.01 98.0 1
Heat shock protein HSP90
CHEMBL2095165
 IC50 6.76 5.645 173.6 2
NHDF
CHEMBL614200
 IC50 6.72 6.555 190.0 2
MCF7
CHEMBL387
 IC50 6.66 5.835 220.0 4
MDA-MB-231
CHEMBL400
 IC50 6.6 6.6 250.0 1
OVCAR-3
CHEMBL614213
 IC50 6.54 6.475 287.0 2
CHO
CHEMBL613853
 IC50 6.53 6.47 294.0 2
HeLa
CHEMBL399
 IC50 6.5 6.5 320.0 1
HT-29
CHEMBL384
 IC50 6.45 6.28 357.0 2
HMEC
CHEMBL614734
 IC50 6.41 6.41 390.0 1
CAPAN-1
CHEMBL614536
 IC50 6.41 5.96 390.0 2
PC-3
CHEMBL390
 IC50 6.36 6.36 440.0 1
UCLA P-3
CHEMBL612797
 IC50 6.14 6.14 730.0 1
SK-MEL-28
CHEMBL614919
 IC50 5.85 5.825 1410.0 2
M19-MEL
CHEMBL614019
 IC50 5.7 5.7 2000.0 1
EVSA-T
CHEMBL614295
 IC50 5.7 5.7 2000.0 1
T-24
CHEMBL614774
 IC50 5.7 5.7 2000.0 1
A204
CHEMBL614514
 IC50 5.52 5.52 3000.0 1
A498
CHEMBL614516
 IC50 5.52 5.52 3000.0 1
WiDr
CHEMBL614647
 IC50 5.16 5.16 7000.0 1
Unchecked
CHEMBL612545
 IC50 5.13 5.13 7480.0 1
SW-620
CHEMBL612262
 IC50 5.07 5.07 8600.0 1
IGR-37 cell line
CHEMBL613985
 IC50 4.96 4.96 11000.0 1
IGROV-1
CHEMBL613984
 IC50 4.75 4.75 18000.0 1
HEK293
CHEMBL614818
 IC50 4.75 4.75 17720.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MOLT-4 IC50 = 1.0 nM 9.0 Cytotoxicity of compound was tested against Molt-4 cell line (T-cell leukemia) a... -
P388 IC50 = 3.0 nM 8.52 Growth Inhibition of P388/0 cell lines. 10669575
K562 IC50 = 15.0 nM 7.82 Cytotoxicity against drug-sensitive K562 cell line by MTS assay 16509594
L1210 (1565) IC50 = 16.0 nM 7.8 Cytotoxic activity against L-1210 parental cell line -
HL-60 IC50 = 98.0 nM 7.01 Cytotoxicity of compound was tested against HL-60 cell line (promyelocytic leuke... -
L1210 (1565) IC50 = 147.0 nM 6.83 Cytotoxic activity against adriamycin (ADR) resistant L-1210 cell line -
Heat shock protein HSP90 IC50 = 173.6 nM 6.76 PUBCHEM_BIOASSAY: Tumor Hsp90 Inhibitors Dose Response Confirmation. (Class of a... -
NHDF IC50 = 190.0 nM 6.72 Cytotoxicity of compound was tested against NHDF cell line (norm human dermal fi... -
MCF7 IC50 = 220.0 nM 6.66 Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay 17190447
MDA-MB-231 IC50 = 250.0 nM 6.6 Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay 17190447
OVCAR-3 IC50 = 287.0 nM 6.54 Cytotoxicity of compound was tested against Ovcar-3 cell line (ovarian carcinoma... -
CHO IC50 = 294.0 nM 6.53 Cytotoxicity of compound was tested against CHO cell line (Chinese hamster ovary... -
HeLa IC50 = 320.0 nM 6.5 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay 17190447
HT-29 IC50 = 357.0 nM 6.45 Cytotoxicity of compound was tested against HT-29 cell line (colon carcinoma) af... -
CAPAN-1 IC50 = 390.0 nM 6.41 Cytotoxicity of compound was tested against Capan-1 cell line (pancreatic carcin... -
CHO IC50 = 390.0 nM 6.41 Cytotoxicity of compound was tested against CHO cell line (Chinese hamster ovary... -
OVCAR-3 IC50 = 390.0 nM 6.41 Cytotoxicity of compound was tested against Ovcar-3 cell line (ovarian carcinoma... -
P388 IC50 = 390.0 nM 6.41 Cytotoxicity of compound was tested against P-388 cell line (mouse leukemia) aft... -
HMEC IC50 = 390.0 nM 6.41 Cytotoxicity of compound was tested against HMEC cell line (human mamm epithelia... -
NHDF IC50 = 404.0 nM 6.39 Cytotoxicity of compound was tested against NHDF cell line (norm human dermal fi... -

Literature References

PubMed DOI Target Context # Activities
423181 10.1021/jm00187a009 P388 8
1255661 10.1021/jm00225a008 Unchecked 7
17284452 10.1074/jbc.m608207200 Unchecked 4
7252976 10.1021/jm00138a005 Mus musculus 4
423181 10.1021/jm00187a009 Salmonella typhimurium 4
16509594 10.1021/jm050916m K562 3
- 10.1016/S0960-894X(00)80285-1 SK-MEL-28 2
7252976 10.1021/jm00138a005 L1210 2
- 10.1016/S0960-894X(00)80285-1 NHDF 2
- 10.1016/0960-894X(95)00067-4 L1210 (1565) 2
- 10.1016/S0960-894X(00)80285-1 HMEC 2
10669575 10.1021/jm990498j M109 2
6716401 10.1021/jm00371a014 Nucleic Acid 2
- 10.1016/S0960-894X(00)80285-1 OVCAR-3 2
- 10.1016/S0960-894X(00)80285-1 MOLT-4 2
- 10.1016/S0960-894X(00)80285-1 CAPAN-1 2
- 10.1016/S0960-894X(00)80285-1 CHO 2
- 10.1016/S0960-894X(00)80285-1 HL-60 2
- 10.1016/S0960-894X(00)80285-1 HT-29 2
- 10.1016/S0960-894X(00)80285-1 MCF7 2

Data from ChEMBL 36 via Core Engine