Compound Detail

CHEMBL178

DAUNORUBICIN

💊 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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL178
Name	DAUNORUBICIN
Phase	Approved
Structure Type	MOL
InChI Key	STQGQHZAVUOBTE-VGBVRHCVSA-N
Therapeutic	✓ Yes

Known Names

Daunomycin Daunorubicin Daunorubicin component of vyxeos Daunorubicina Daunorubicine Daunoxome Epirubicin hydrochloride impurity, daunorubicin- FI 6339 FI-6339 NSC-83142 RP 13057 RP-13057 +1 more

Targets

183

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

527.5

MW (Da)

1.03

ALogP

HBA

HBD

185.8

PSA (Å²)

0.31

QED

Ro5 Violations

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	C27H29NO10
MW	527.53
Aromatic Rings	2
Heavy Atoms	38
NP-Likeness	1.75

Mechanism of Action

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

Indications

Leukemia, Myeloid, Acute Neoplasms Hepatitis B, Chronic Leukemia Leukemia, Myeloid Lymphoma, Non-Hodgkin Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor T-Cell Lymphoblastic Leukemia-Lymphoma Sarcoma, Kaposi Anemia, Refractory Leukemia, Lymphoid Myelodysplastic Syndromes Hematologic Neoplasms Leukemia, Biphenotypic, Acute Leukemia, Myelogenous, Chronic, BCR-ABL Positive Polycythemia Vera Primary Myelofibrosis Thrombocythemia, Essential

ATC Classification

L01DB02

daunorubicin

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 173 meas. best 8.52

EC50 5 meas. best 7.24

Ki 5 meas. best 7.16

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
P388 CHEMBL389	IC50	8.52	7.89	3.0	3
NCI-H460 CHEMBL396	IC50	8.46	7.44	3.5	2
NSCLC CHEMBL612554	IC50	8.41	8.41	3.9	1
HL-60 CHEMBL383	IC50	8.3	7.335	5.0	4
Unchecked CHEMBL612545	IC50	8.21	6.7524	6.1	25
KB 3-1 CHEMBL614590	IC50	8.15	8.15	7.0	2
YOSHIDA CHEMBL612816	IC50	8.13	8.13	7.4	1
B16 CHEMBL381	IC50	8.05	8.045	8.9	2
DNA topoisomerase 2-alpha CHEMBL1806	IC50	8.0	8.0	10.0	1
NCI-H1975 CHEMBL614348	IC50	7.88	7.88	13.3	1
MES-SA/Dx5 CHEMBL613827	IC50	7.85	6.775	14.0	2
K562 CHEMBL385	IC50	7.82	6.5167	15.0	6
MDA-MB-361 CHEMBL614129	IC50	7.77	7.63	17.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.7	5.7583	20.0	6
Histone deacetylase 6 CHEMBL1865	IC50	7.7	7.7	20.0	1
MES-SA CHEMBL614343	IC50	7.68	6.7867	21.0	3
HepG2 CHEMBL395	IC50	7.67	5.8825	21.3	4
DU-145 CHEMBL613508	IC50	7.61	7.1833	24.5	3
PC-3 CHEMBL390	IC50	7.58	7.175	26.0	2
U-87 MG CHEMBL614247	IC50	7.55	7.55	27.9	1
L1210 CHEMBL386	IC50	7.52	7.4667	30.0	3
A2058 CHEMBL613503	IC50	7.48	7.48	33.3	1
MCF7 CHEMBL387	IC50	7.41	6.1638	39.0	13
P388/ADR CHEMBL614218	IC50	7.4	6.6833	40.0	3
4T1 CHEMBL612589	IC50	7.39	6.955	40.8	2
ADMET CHEMBL612558	IC50	7.36	6.03	44.0	3
Histone deacetylase 1 CHEMBL325	IC50	7.33	7.33	47.0	1
WALKER CHEMBL613532	IC50	7.33	7.33	47.0	1
NCI-H1650 CHEMBL1075518	IC50	7.32	7.32	47.5	1
MDA-MB-231 CHEMBL400	IC50	7.28	7.16	52.9	2
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.24	6.95	58.0	2
U2OS CHEMBL615023	IC50	7.21	7.21	61.0	1
Lewis lung carcinoma cell line CHEMBL614088	IC50	7.21	7.21	61.0	1
ACHN CHEMBL614519	IC50	7.2	7.2	63.0	1
A549 CHEMBL392	IC50	7.17	6.7267	68.2	6
Multidrug resistance-associated protein 1 CHEMBL3004	Ki	7.16	6.59	70.0	2
MRC5 CHEMBL614181	IC50	7.11	6.5867	78.0	3
MDA-MB-435 CHEMBL614697	IC50	7.1	6.6667	79.0	3
Jurkat CHEMBL397	IC50	7.08	7.08	82.6	1
BHK-21 CHEMBL614527	IC50	7.05	7.05	90.0	1
NCI-H69 CHEMBL614805	IC50	7.0	7.0	100.0	1
LNCaP CHEMBL612518	IC50	7.0	7.0	100.0	1
HeLa CHEMBL399	IC50	7.0	6.265	100.0	2
A2780 CHEMBL614004	IC50	6.93	6.93	117.5	1
HCT-116 CHEMBL394	IC50	6.9	6.79	127.1	2
CT26.WT CHEMBL4513123	IC50	6.9	6.64	126.0	2
HT-29 CHEMBL384	IC50	6.88	6.6675	133.0	4
Plasmodium falciparum CHEMBL364	IC50	6.81	6.64	155.0	2
B16 CHEMBL381	EC50	6.8	6.8	160.0	1
SK-MES-1 CHEMBL614923	IC50	6.77	6.77	170.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	86.0	ug.ml-1	Canis lupus familiaris
AUC	601.9	-	Chlorocebus sabaeus
Clp	2031.0	ml.min-1	Canis lupus familiaris
Clp	59.0	ml.min-1	Canis lupus familiaris
F	-	%	Homo sapiens
Ka	3.1e-07	M-1	Clupeidae
T1/2	0.08833	hr	Canis lupus familiaris
T1/2	24.2	hr	Canis lupus familiaris
Vd	51.0	L.kg-1	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
P388	IC50	=	3.0	nM	8.52	Compound was evaluated for cytotoxicity against P388 leukemia cell line.	10479297
NCI-H460	IC50	=	3.5	nM	8.46	Evaluated in vitro for antiproliferative activity against NIC-H460 cell lines de...	-
NSCLC	IC50	=	3.9	nM	8.41	Evaluated in vitro for antiproliferative activity against NYH cell lines derived...	-
HL-60	IC50	=	5.0	nM	8.3	In vitro inhibitory concentration against proliferation of HL60 cells	12877593
Unchecked	IC50	=	6.1	nM	8.21	PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce...	-
KB 3-1	IC50	=	7.0	nM	8.15	In vitro cytotoxicity using human epidermoid carcinoma (KB-3-1) cells	-
KB 3-1	IC50	=	7.0	nM	8.15	In vitro cytotoxic activity was evaluated using the human epidermoid carcinoma c...	12443763
YOSHIDA	IC50	=	7.4	nM	8.13	In vitro antiproliferative activity against Yoshida cell lines	-
Unchecked	IC50	=	8.05	nM	8.09	PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator...	-
B16	IC50	=	8.9	nM	8.05	Cytostatic activity against mouse B16 cells preincubated for 24 hrs under serum ...	31100648
B16	IC50	=	9.2	nM	8.04	In vitro antiproliferative activity against B16 cell lines	-
DNA topoisomerase 2-alpha	IC50	=	10.0	nM	8.0	Inhibition of Topo IIalpha (unknown origin)	37847948
Unchecked	IC50	=	10.16	nM	7.99	PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of ass...	-
NCI-H1975	IC50	=	13.3	nM	7.88	Cytostatic activity against human NCI-H1975 cells preincubated for 24 hrs under ...	31100648
MES-SA/Dx5	IC50	=	14.0	nM	7.85	The compound was evaluated for the growth inhibition of Dx5 w/PSC cell lines usi...	10698449
HL-60	IC50	=	15.0	nM	7.82	Antiproliferative activity against human HL-60 cells after 72 hrs by XTT assay	33750129
K562	IC50	=	15.0	nM	7.82	Cytotoxicity against K562 cells by MTS	16451059
MDA-MB-361	IC50	=	17.0	nM	7.77	The compound was tested for intracellular cytotoxicity against MDA MB 361(mammar...	10395490
Histone deacetylase 6	IC50	=	20.0	nM	7.7	Inhibition of HDAC6 (unknown origin)	33143937
NON-PROTEIN TARGET	IC50	=	20.0	nM	7.7	Antiproliferative activity against drug sensitive Messa cell line by Alamar Blue...	17286393

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	892
7452666	10.1021/jm00185a004	Mus musculus	24
21051535	10.1124/dmd.110.034629	ADMET	21
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22480495	10.1016/j.ejmech.2012.03.016	MONO-MAC-6	17
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
1992140	10.1021/jm00105a007	P388	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
1271407	10.1021/jm00227a015	L1210	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
-	10.1007/s00044-008-9154-8	ADMET	8
370390	10.1021/jm00189a006	Salmonella typhimurium	7
16451059	10.1021/jm050800q	K562	7
39088428	10.1021/acs.jmedchem.4c00614	ADMET	7
176359	10.1021/jm00225a011	P388	7
628003	10.1021/jm00201a009	P388	7
11602674	-	ATP-dependent translocase ABCB1	7
10479297	10.1021/jm990166e	Mus musculus	6
29016119	10.1021/acs.jmedchem.7b00788	Unchecked	6
571021	10.1021/jm00190a010	P388	5

Data from ChEMBL 36 via Core Engine