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Compound Detail

CHEMBL1417019

MITOXANTRONE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.Cl.O=C1c2c(O)ccc(O)c2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1417019
Name MITOXANTRONE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key ZAHQPTJLOCWVPG-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL58
Active Moiety CHEMBL58

Known Names

CL 232,315 CL-232315 Mitoxantrone dihcl Mitoxantrone dihydrochloride Mitoxantrone hcl Mitoxantrone hydrochloride Mitozantrone Novantrone NSC-301739
10
Targets
32
Activities
2
Assay Types
0
PK Parameters
20
Publications
9
Known Names
20
Indications
2
Mechanisms

Molecular Properties

444.5
MW (Da)
-0.14
ALogP
10
HBA
8
HBD
163.2
PSA (Ų)
0.14
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral

Flags

Black Box Warning
USAN Stem -antrone
USAN Year 1980

Extended Properties

Molecular Formula C22H30Cl2N4O6
MW 517.41
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness 0.22

Mechanism of Action

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

Indications

Multiple Sclerosis Prostatic Neoplasms Prostatic Neoplasms Breast Neoplasms Leukemia Leukemia, Lymphoid Leukemia, Myeloid, Acute Leukemia, Promyelocytic, Acute Lymphoma Lymphoma, Non-Hodgkin Lymphoma, T-Cell, Peripheral Myelodysplastic Syndromes Myeloproliferative Disorders Nasopharyngeal Neoplasms Ovarian Neoplasms Pain Prostatic Neoplasms, Castration-Resistant Sarcoma, Myeloid Sarcoma, Myeloid Granuloma, Lethal Midline

Drug Warnings

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

Activity Summary

IC50 31 meas. best 9.0
EC50 1 meas. best 5.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.0 6.1678 1.0 18
Trypanosoma brucei brucei
CHEMBL612851
 IC50 8.62 7.31 2.4 2
HL-60
CHEMBL383
 IC50 8.14 8.14 7.2 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
 IC50 7.29 7.29 50.9 1
MCF7
CHEMBL387
 IC50 7.0 6.11 100.0 3
LoVo
CHEMBL614721
 IC50 7.0 6.525 100.0 2
HL60/MX2
CHEMBL4296431
 IC50 6.46 6.46 350.7 1
DNA repair nuclease/redox regulator APEX1
CHEMBL5619
 IC50 5.7 5.7 2000.0 1
DNA-3-methyladenine glycosylase
CHEMBL3396943
 IC50 5.6 5.6 2500.0 1
Nucleic Acid
CHEMBL345
 IC50 5.35 5.35 4500.0 1
Unchecked
CHEMBL612545
 EC50 5.18 5.18 6580.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Trypanosoma brucei brucei IC50 = 2.4 nM 8.62 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei brucei ... 23927763
Unchecked IC50 = 3.1 nM 8.51 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
Unchecked IC50 = 4.4 nM 8.36 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
HL-60 IC50 = 7.2 nM 8.14 Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay 28333459
Unchecked IC50 = 12.74 nM 7.89 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (vi... -
Unchecked IC50 = 30.3 nM 7.52 PubChem BioAssay. nuclear beta catenin stimulation in WNT3A conditioned C2C12 ce... -
Serine/threonine-protein kinase pim-1 IC50 = 50.9 nM 7.29 Inhibition of recombinant PIM1 (unknown origin) expressed in Escherichia coli BL... 23442188
LoVo IC50 = 100.0 nM 7.0 Cytotoxicity against human LoVo cells under oxic condition assessed as growth in... 22011244
MCF7 IC50 = 100.0 nM 7.0 Cytotoxicity against doxorubicin-sensitive human MCF7 cells under oxic condition... 22011244
HL60/MX2 IC50 = 350.7 nM 6.46 Antiproliferative activity against human HL60/MX2 cells after 72 hrs by MTT assa... 28333459
LoVo IC50 = 900.0 nM 6.05 Cytotoxicity against human LoVo cells under hypoxic condition assessed as growth... 22011244
MCF7 IC50 = 1000.0 nM 6.0 Cytotoxicity against doxorubicin-sensitive human MCF7 cells under hypoxic condit... 22011244
Trypanosoma brucei brucei IC50 = 1000.0 nM 6.0 Trypanocidal activity against Trypanosoma brucei brucei by Alamar Blue assay 23927763
Unchecked IC50 = 1029.1 nM 5.99 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 1233.5 nM 5.91 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 1509.0 nM 5.82 PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce... -
Unchecked IC50 = 1603.8 nM 5.79 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1718.0 nM 5.76 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 1830.6 nM 5.74 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -

Literature References

PubMed DOI Target Context # Activities
490545 10.1021/jm00195a002 P388 5
22011244 10.1021/jm200984x MCF7 4
490545 10.1021/jm00195a002 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
490545 10.1021/jm00195a002 L5178Y 2
490545 10.1021/jm00195a002 Lewis lung carcinoma cell line 2
490545 10.1021/jm00195a002 Mus musculus 2
23927763 10.1021/jm4004279 Trypanosoma brucei brucei 2
22011244 10.1021/jm200984x LoVo 2
490545 10.1021/jm00195a002 B16 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
23442188 10.1021/jm400045y Serine/threonine-protein kinase pim-1 1
25650313 10.1016/j.bmc.2014.12.067 Unchecked 1
25650313 10.1016/j.bmc.2014.12.067 DNA-3-methyladenine glycosylase 1
28333459 10.1021/acs.jmedchem.6b01502 HL-60 1
28333459 10.1021/acs.jmedchem.6b01502 Unchecked 1
28333459 10.1021/acs.jmedchem.6b01502 HL60/MX2 1
28161249 10.1016/j.bmc.2017.01.028 DNA repair nuclease/redox regulator APEX1 1
22011244 10.1021/jm200984x Nucleic Acid 1

Data from ChEMBL 36 via Core Engine