Compound Detail

CHEMBL58

MITOXANTRONE

💊 Approved Drug

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💊 Approved Drug

O=C1c2c(O)ccc(O)c2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL58
Name	MITOXANTRONE
Phase	Approved
Structure Type	MOL
InChI Key	KKZJGLLVHKMTCM-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Misostol Mitoxantrona Mitoxantrone NSC-279836

Targets

305

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

444.5

MW (Da)

-0.14

ALogP

HBA

HBD

163.2

PSA (Å²)

0.14

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1987
Availability	Prescription
Chirality	Achiral

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	-antrone
USAN Year	1980

Extended Properties

Molecular Formula	C22H28N4O6
MW	444.49
Aromatic Rings	2
Heavy Atoms	32
NP-Likeness	0.22

Indications

Neoplasms Neoplasms Leukemia Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Lymphoid Leukemia, Myeloid, Acute Leukemia, Promyelocytic, Acute Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Multiple Sclerosis Multiple Sclerosis, Chronic Progressive Precursor Cell Lymphoblastic Leukemia-Lymphoma Precursor Cell Lymphoblastic Leukemia-Lymphoma Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Leukemia, Biphenotypic, Acute Lymphoma Lymphoma, Mantle-Cell

ATC Classification

L01DB07

mitoxantrone

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 274 meas. best 10.62

EC50 19 meas. best 7.52

Ki 9 meas. best 7.11

Kd 3 meas. best 7.48

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
HL-60 CHEMBL383	IC50	10.62	6.9219	0.0	16
A549 CHEMBL392	IC50	10.44	6.6573	0.0	11
L1210 CHEMBL386	IC50	10.4	7.7332	0.0	19
SGC-7901 CHEMBL614909	IC50	9.53	9.53	0.3	1
MDA-MB-435 CHEMBL614697	IC50	9.46	7.1633	0.3	3
A2780 CHEMBL614004	IC50	9.26	7.918	0.6	5
Plasmodium falciparum CHEMBL364	IC50	9.23	7.4979	0.6	14
G-361 CHEMBL614036	IC50	9.19	9.19	0.7	1
ADMET CHEMBL612558	IC50	9.12	8.1943	0.8	7
Multidrug resistance-associated protein 1 CHEMBL3004	IC50	8.82	8.48	1.5	4
K562 CHEMBL385	IC50	8.59	6.7638	2.6	8
CH1 CHEMBL614455	IC50	8.58	8.58	2.6	2
Unchecked CHEMBL612545	IC50	8.52	6.7017	3.0	12
MES-SA CHEMBL614343	IC50	8.52	8.1867	3.0	3
LoVo CHEMBL614721	IC50	8.48	7.1586	3.3	7
P388 CHEMBL389	IC50	8.37	6.465	4.3	2
MCF7 CHEMBL387	IC50	8.3	7.0913	5.0	16
Daudi CHEMBL614281	IC50	8.3	8.3	5.0	1
SK-OV-3 CHEMBL614925	IC50	8.28	7.4625	5.3	4
DU-145 CHEMBL613508	IC50	8.25	8.25	5.6	1
HCT-116 CHEMBL394	IC50	8.24	6.4243	5.8	7
OVCAR-3 CHEMBL614213	IC50	8.24	8.235	5.8	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.22	6.9307	6.0	14
PC-3 CHEMBL390	IC50	8.15	7.6133	7.0	3
2008 CHEMBL612818	IC50	8.11	8.11	7.8	1
WiDr CHEMBL614647	IC50	8.1	7.1325	8.0	8
Homo sapiens CHEMBL372	IC50	8.0	8.0	10.0	1
HT-29 CHEMBL384	IC50	8.0	6.8857	10.0	14
XRS6 CHEMBL614060	IC50	8.0	8.0	10.0	1
Ishikawa CHEMBL614649	IC50	8.0	8.0	10.0	1
HEK293 CHEMBL614818	IC50	8.0	7.334	10.0	5
MKN-45 CHEMBL614354	IC50	7.92	7.92	12.0	1
HCC78 CHEMBL4296421	IC50	7.86	7.86	13.8	1
SK-BR-3 CHEMBL613834	IC50	7.8	7.8	16.0	1
N592 CHEMBL613969	IC50	7.7	7.7	20.0	1
A-375 CHEMBL613859	IC50	7.58	7.265	26.0	2
Tumor cell line CHEMBL614310	IC50	7.57	7.57	27.0	1
MES-SA/Dx5 CHEMBL613827	IC50	7.55	7.55	28.0	1
NCI-H460 CHEMBL396	EC50	7.52	7.22	30.0	2
RPMI-8226 CHEMBL614882	IC50	7.52	7.135	30.0	2
Unchecked CHEMBL612545	Kd	7.48	7.4333	33.0	3
CCRF-CEM CHEMBL382	IC50	7.44	6.44	36.0	2
HeLa CHEMBL399	IC50	7.4	6.7967	40.0	3
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.38	6.555	42.0	6
UACC-375 CHEMBL614127	IC50	7.32	7.32	48.0	4
HT-1080 CHEMBL614580	IC50	7.18	7.18	66.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	7.11	7.11	77.9	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.05	7.05	89.8	1
Bel-7402 CHEMBL614279	IC50	6.93	6.93	116.6	1
SK-OV-3 CHEMBL614925	EC50	6.92	6.92	120.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	7.9	mL.min-1.kg-1	Homo sapiens
CL	7.9	mL.min-1.kg-1	Homo sapiens
Fu	0.25	-	Homo sapiens
Fu	0.13	-	Homo sapiens
Fu	0.0046	-	Rattus norvegicus
Ka	1.0	10'6/M	Bos taurus
MRT	25.0	hr	Homo sapiens
T1/2	53.0	hr	Homo sapiens
T1/2	0.42	hr	Not specified
Vd	1757.0	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
HL-60	IC50	=	0.024	nM	10.62	Antiproliferative activity against human HL60 cells after 72 hrs by CCK8 assay	30485090
A549	IC50	=	0.036	nM	10.44	Antiproliferative activity against human A549 cells after 72 hrs by sulforhodami...	30485090
L1210	IC50	=	0.04	nM	10.4	Cytotoxic potency required to inhibit L1210 cell growth by 50% after cell drug c...	9371240
SGC-7901	IC50	=	0.293	nM	9.53	Antiproliferative activity against human SGC7901 cells after 72 hrs by sulforhod...	30485090
MDA-MB-435	IC50	=	0.35	nM	9.46	Antiproliferative activity against MDA435/LCC6 cells by ELISA	17154505
A2780	IC50	=	0.55	nM	9.26	Concentration required to inhibit A2780-cell growth by 50%	9703471
A2780	IC50	=	0.55	nM	9.26	Cytotoxic potency required to inhibit A2780 cell growth by 50% after cell drug c...	9371240
Plasmodium falciparum	IC50	=	0.59	nM	9.23	Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g...	19734910
G-361	IC50	=	0.65	nM	9.19	Cytotoxic potency required to inhibit G-361 cell growth by 50%	9371240
ADMET	IC50	=	0.75	nM	9.12	Cytotoxicity against human H460M cancer cell line was determined after 144 hr	15456268
HL-60	IC50	=	0.81	nM	9.09	Compound was tested in vitro for cytotoxicity against HL60 human leukemia cell l...	10479282
Plasmodium falciparum	IC50	=	0.83	nM	9.08	Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g...	19734910
ADMET	IC50	=	0.85	nM	9.07	Cytotoxicity against human H460M cancer cell line was determined after 1 hr	15456268
Plasmodium falciparum	IC50	=	0.93	nM	9.03	Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g...	19734910
ADMET	IC50	=	1.0	nM	9.0	Tested for the cytotoxicity against the repair deficient xrs-6 chinese hamster o...	7525959
Plasmodium falciparum	IC50	=	1.0	nM	9.0	Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	1.12	nM	8.95	Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr...	19734910
Plasmodium falciparum	IC50	=	1.41	nM	8.85	Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	1.48	nM	8.83	Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g...	19734910
Multidrug resistance-associated protein 1	IC50	=	1.5	nM	8.82	TP_TRANSPORTER: cell accumulation in MCF7/MRP1-M24 cells	16434618

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	357
10479282	10.1021/jm980682p	HT-29	19
16472241	10.2174/1570163043334794	Hepatotoxicity	18
29232579	10.1016/j.ejmech.2017.11.101	NEDD8 activating enzyme	16
29232579	10.1016/j.ejmech.2017.11.101	Caco-2	15
19734910	10.1038/nchembio.215	Plasmodium falciparum	14
30108778	10.1039/C6MD00643D	HCC78	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
19553129	10.1016/j.bmc.2009.05.070	Unchecked	14
19786608	10.1128/aac.00803-09	Mycolicibacterium smegmatis	12
458801	10.1021/jm00191a008	P388	12
10479282	10.1021/jm980682p	Mus musculus	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
628005	10.1021/jm00201a012	P388	11
3351863	10.1021/jm00399a028	L1210	11
458801	10.1021/jm00191a008	L1210	10
21051535	10.1124/dmd.110.034629	ADMET	9
36167009	10.1016/j.ejmech.2022.114784	Unchecked	9
30925340	10.1016/j.ejmech.2019.03.051	H22	9
458801	10.1021/jm00191a008	B16	8

Data from ChEMBL 36 via Core Engine