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

• ChemBase ID: 1074
• Molecular Formular: C22H28N4O6
• Molecular Mass: 444.48092
• Monoisotopic Mass: 444.20088464
• SMILES: O=C1c2c(c(NCCNCCO)ccc2NCCNCCO)C(=O)c2c1c(O)ccc2O
• Canonical SMILES: OCCNCCNc1ccc(c2c1C(=O)c1c(C2=O)c(O)ccc1O)NCCNCCO
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: mitoxantrone
• Brand Name: Mitox; Novantron; Novantrone
• Synonyms: DHAD; DHAQ; DHAQ HCl; Dihydroxyanthraquinone; Mitoxanthrone; Mitoxantron; Mitoxantrona [INN-Spanish]; Mitoxantrone 2HCl; Mitoxantrone dihydrochloride; Mitoxantrone HCl; Mitoxantrone hydrochloride; Mitoxantronum [INN-Latin]; Mitozantrone hydrochloride; Mitozantrone; mitoxantrone; Mitoxantrone; 1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione Hydrochloride; Bisantrone; CL 232315; Immunex; NCI 301739; NSC 301739; Novatrone; Mitoxantrone Dihydrochloride; 1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione; 1,4-Bis[(2-(2-hydroxyethylamino)ethyl)amino]-5,8-dihydroxyanthraquinone; Mitox; Nimitoxantron; Novantron; Novantrone; Ralenova; NSC 279836

Database IDs

• CAS Number: 70476-82-3; 65271-80-9
• PubChem SID: 46504608; 160964537
• PubChem CID: 4212

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.775683
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -4.25051
• LogD (pH = 7.4): -1.2001225
• Log P: 1.1855145
• Molar Refractivity: 123.5338 cm^3
• Polarizability: 45.86351 Å^3
• Polar Surface Area: 163.18 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.91
• LOG S: -2.78
• Solubility (Water): 7.34e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Dark Blue Solid
• Melting Point: 170-174°C; 265-270°C (dec.)
• Hydrophobicity(logP): -3.1

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Refrigerator

Pharmacology Properties

• Target: Topoisomerase

Product Information

• Salt Data: Free Base

DETAILS

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

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]

Toronto Research Chemicals - M373425

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

Toronto Research Chemicals - M373426

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

REFERENCES

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