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

• ChemBase ID: 72816
• Molecular Formular: C22H30Cl2N4O6
• Molecular Mass: 517.4028
• Monoisotopic Mass: 516.15424006
• SMILES: c1cc(c2c(c1O)C(=O)c1c(C2=O)c(ccc1NCCNCCO)NCCNCCO)O.Cl.Cl
• Canonical SMILES: OCCNCCNc1ccc(c2c1C(=O)c1c(C2=O)c(O)ccc1O)NCCNCCO.Cl.Cl
• InChI: InChI=1S/C22H28N4O6.2ClH/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;2*1H
• InChIKey: ZAHQPTJLOCWVPG-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 dihydrochloride
• IUPAC Traditional name: mitoxantrone dihydrochloride
• Synonyms: NSC-310739; Novantrone; Mitoxantrone Hydrochloride; 1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione dihydrochloride; Mitoxantrone dihydrochloride

Database IDs

• CAS Number: 70476-82-3
• EC Number: 274-619-1
• MDL Number: MFCD00242943
• PubChem SID: 162037737; 24278562
• PubChem CID: 51082

CALCULATED PROPERTIES

• 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

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: CB5748500
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 46-61
• Safety Statements: 53-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: DNA/RNA

Product Information

• Purity: ≥97% (HPLC)
• Salt Data: Hydrochloride

DETAILS

Selleck Chemicals - S1889

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]

Sigma Aldrich - M6545

Biochem/physiol Actions
Mitoxantrone is a cytostatic anthracenedione that intercalates in DNA and increases the incidence of double-strand breaks by stabilizing the cleavable complex of topoisomerase II and DNA. Mitoxantrone also displays broad immunosuppressive activity inhibiting proliferation of all classes of lymphocytes and inducing apoptosis of antigen-presenting T cells. It used clinically as a chemotherapeutic agent against leukemias and solid tumors and as an immune system modulator in multiple sclerosis.

REFERENCES

• Desai PB et al. Pharm Res. 1992 Feb; 9(2):178-81