ContaminantDB: Mitoxantrone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (13)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:38 UTC

Update Date

2026-05-14 16:58:43 UTC

Accession Number

CHEM002377

Identification

Common Name

Mitoxantrone

Class

Small Molecule

Description

Mitoxantrone is only found in individuals that have used or taken this drug. It is an anthracenedione-derived antineoplastic agent. Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.

Contaminant Sources

HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Analgesic
Antineoplastic Agent
Drug
Ester
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-DIHYDROXY-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-anthracenedione	ChEBI
Mitoxantrona	ChEBI
Mitoxantronum	ChEBI
Misostol	Kegg
Mitoxanthrone	HMDB
Mitoxantron	HMDB
ASTA medica brand OF mitoxantrone hydrochloride	HMDB
Ralenova	HMDB
Wyeth brand OF mitoxantrone hydrochloride	HMDB
AHP brand OF mitoxantrone hydrochloride	HMDB
Acetate, mitoxantrone	HMDB
Lederle brand OF mitoxantrone hydrochloride	HMDB
Mitozantrone	HMDB
Novantron	HMDB
Baxter oncology brand OF mitoxantrone hydrochloride	HMDB
Columbia brand OF mitoxantrone hydrochloride	HMDB
Hydrochloride, mitoxantrone	HMDB
Mitoxantrone acetate	HMDB
Novantrone	HMDB
Onkotrone	HMDB
Pralifan	HMDB
Amgen brand OF mitoxantrone hydrochloride	HMDB
DHAQ	HMDB
Inibsa brand OF mitoxantrone hydrochloride	HMDB
Mitoxantrone hydrochloride	HMDB
Mitroxone	HMDB

Chemical Formula

C₂₂H₂₈N₄O₆

Average Molecular Mass

444.481 g/mol

Monoisotopic Mass

444.201 g/mol

CAS Registry Number

65271-80-9

IUPAC Name

1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione

Traditional Name

mitoxantrone

SMILES

OCCNCCNC1=C2C(=O)C3=C(O)C=CC(O)=C3C(=O)C2=C(NCCNCCO)C=C1

InChI Identifier

InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2

InChI Key

KKZJGLLVHKMTCM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Vinylogous acid
Vinylogous amide
1,2-aminoalcohol
Ketone
Secondary amine
Secondary aliphatic amine
Alkanolamine
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:50729 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

analgesic

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	7.34e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	0.91	ALOGPS
logP	1.19	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	163.18 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	123.53 m³·mol⁻¹	ChemAxon
Polarizability	48.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03k9-4008900000-031c3e5b5c6fbec57bdc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-052b-3100094000-753b733851babd16586e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4j-0394000000-5f26812f41567533fe71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0012900000-147e3b4eed2bd9c29e51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4j-0394000000-5f26812f41567533fe71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3003900000-9c369ecea59cd969c230	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9004200000-d4db7c5244eae35ee957	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000m-9023000000-a3182f5d9afc8da8c7bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1001900000-a08d98fc5346d9d02409	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-4015900000-de9bc44a9432611d1ba2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-9214200000-bbad802d490cbc39d94d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-9872ce7cd43051fb4999	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-0007900000-f6154c5a82d91a893f26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-7019000000-8870a13752c5782dc6ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-1d51c2d6aecce92b7f20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0004900000-386f03ecb86d1b84ef6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00rb-0049000000-4e3c4122979a10d299c2	Spectrum

Toxicity Profile

Route of Exposure

Intravenous injection. Poorly absorbed following oral administration.

Mechanism of Toxicity

Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.

Metabolism

Hepatic Half Life: 75 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (2)

Uses/Sources

For the treatment of secondary (chronic) progressive, progressive relapsing, or worsening relapsing-remitting multiple sclerosis. Mitoxantrone is an Anthracenedione (not an anthracycline) antineoplastic agent.

Minimum Risk Level

Not Available

Health Effects

Cardiomyopathy is a particularly concerning effect as it is irreversible. [Wikipedia]

Symptoms

Severe leukopenia with infection.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID