CAS 65271-80-9|CAS 70476-82-3|Mitoxantron|Mitoxantrona [INN-Spanish]|Mitozantrone|Mitoxantrone HCl|Novantrone|DHAQ|mitoxantrone|Mitoxantronum [INN-Latin]|Mitoxanthrone|mitoxantrone|Mitoxantrone dihy...

General Information

Structure

Molecular Formula

C₂₂H₂₈N₄O₆

Molecular Mass

444.48092

Exact Mass

444.20088464

Charge

0

InChI

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

InChIKey

KKZJGLLVHKMTCM-UHFFFAOYSA-N

Canonic Smiles

OCCNCCNc1ccc(c2c1C(=O)c1c(C2=O)c(O)ccc1O)NCCNCCO

Isomeric Smiles

O=C1c2c(c(NCCNCCO)ccc2NCCNCCO)C(=O)c2c1c(O)ccc2O

Calculated Properties

JChem

LogD (pH = 7.4)

-1.36

LogD (pH = 5.5)

-4.32

Log P

0.65

Rotatable Bonds

12

H Donor

8

H Acceptors

10

Lipinski's Rule of Five

false

Acid pKa

9.36

Polar Surface Area

163.18

Polarizability

47.82

Molar Refractivity

123.53

LOG S

-2.32

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

MitoxantronMitoxantrona [INN-Spanish]MitozantroneMitoxantrone HClDHAQmitoxantroneMitoxantronum [INN-Latin]MitoxanthroneMitoxantrone dihydrochlorideDihydroxyanthraquinoneDHADMitozantrone hydrochlorideDHAQ HClMitoxantroneMitoxantrone 2HClMitoxantrone hydrochlorideNCI 301739BisantroneImmunexNimitoxantronNSC 279836Mitox1,4-Bis[(2-(2-hydroxyethylamino)ethyl)amino]-5,8-dihydroxyanthraquinoneMitoxantrone DihydrochlorideRalenovaNSC 301739NovatroneNovantrone1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione HydrochlorideNovantronCL 232315Mitoxantrone1,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)-9,10-ANTHRACENEDIONEmitoxantrone

Brand Name

NovantroneNovantronMitox

IUPAC Traditional name

mitoxantrone

IUPAC name

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

International Nonproprietary Name (INN)

mitoxantronemitoxantronamitoxantronum

Names and Identifiers

Registration numbers

PubChem CID

4212

PubChem SID

1609645374650460856352855

CAS Number

65271-80-970476-82-3

Patent number

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

CHEMBL

CHEMBL58

CHEBI ID

CHEBI:50729CHEBI:43919CHEBI:6955

UniProt Database

Q5MB13O07549P9WI81Q9UNQ0O07550

Protein Data Bank

4g0v2kgp4i416vxi7nfd2fum6gh9

Wikipedia Title

Mitoxantrone

BRENDA Database

5.6.2.21.11.1.141.17.1.13.1.3.487.6.2.22.7.11.184.2.99.181.1.1.1841.11.1.71.6.2.4

BRENDA Ligand Database

22650011262229661132934229662224533127071228546125891

BKMS React Database

22854611262127071125891226500229661224533132934229662

MetaboLights Database

MTBLS2145MTBLS379MTBLS2871MTBLS2825MTBLS417MTBLS2384MTBLS743

DrugBank ID

DB01204

ACToR Database

65271-80-9137635-96-2

LINCS Database

LSM-2481

IntAct Database

EBI-28949089

KEGG ID

C11195

Drug Central Database

BindingDB Database

PDBeChem Database

KEGG DRUG Database

SureChEMBL Database

Beilstein Number

EnzymePortal Database

P0A5S4

CompTox Database

DTXSID4046947

Registration numbers

Properties

Pharmacology Properties

Target

Topoisomerase

Safety Information

Storage Condition

-20°C

-20°C Freezer

Refrigerator

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2485

Research Area: Cancer
Biological Activity:
Mitoxantrone Hydrochloride (NSC301739; Immunex) is a hydrochloride salt of mitoxantrone which is a synthetic antineoplastic anthracenedione (IC50 = 0.42 mM).Mitoxantrone Hydrochloride (NSC301739; Immunex) is also a synthetic antineoplastic anthracenedione. Mitoxantrone Hydrochloride (NSC301739; Immunex) is a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone Hydrochloride (NSC301739; Immunex) also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. Mitoxantrone Hydrochloride (NSC301739; Immunex) has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity. [1][2]

DrugBank

DB01204

Drug Groups

approved; investigational

Description

An anthracenedione-derived antineoplastic agent. [PubChem]

Indication

For the treatment of secondary (chronic) progressive, progressive relapsing, or worsening relapsing-remitting multiple sclerosis

Pharmacology

Mitoxantrone has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2.

Toxicity

Severe leukopenia with infection.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Poorly absorbed following oral administration

Half Life

75 hours

Protein Binding

78%

Distribution

* 1000 L/m2

Clearance

* 21.3 L/hr/m2 [Elderly patients with breast cancer receiving IV administration of 15-90 mg/m2]
* 28.3 L/hr/m2 [Non-elderly patients with nasopharyngeal carcinoma receiving IV administration of 15-90 mg/m2]
* 16.2 L/hr/m2 [Non-elderly patients with malignant lymphoma receiving IV administration of 15-90 mg/m2]

References

• Fox EJ: Management of worsening multiple sclerosis with mitoxantrone: a review. Clin Ther. 2006 Apr;28(4):461-74. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

TRC

M373425

Mitoxantrone is a DNA intercalating drug. Mitoxantrone inhibits DNA synthesis. Mitoxantrone is used as an anti-cancer agent.

M373426

Mitoxantrone is a DNA intercalating drug. Mitoxantrone inhibits DNA synthesis. Mitoxantrone is used as an anti-cancer agent.

ChEBI

CHEBI:50729

A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.

Molecule Details

References

PubChem Literature

From Data Sources

• Fox EJ: Management of worsening multiple sclerosis with mitoxantrone: a review. Clin Ther. 2006 Apr;28(4):461-74. Pubmed

• Parker C et al. Lancet. 2010 Dec 11;376(9757)

• McDonald, M., et al.: Drugs Exp. Clin. Res., 10, 745 (1984)

• Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 17, 221 (1984)

• McDonald, M., et al.: Drugs Exp. Clin. Res., 10, 745 (1984)

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:1074