Mitoxantrone

Base Information

• Chemical Name: Mitoxantrone
• CAS No.: 65271-80-9
• Deprecated CAS: 137635-96-2,70945-62-9
• Molecular Formula: C22H28N4O6
• Molecular Weight: 444.488
• European Community (EC) Number: 833-758-3
• NSC Number: 279836
• UNII: BZ114NVM5P
• DSSTox Substance ID: DTXSID4046947
• Nikkaji Number: J19.969I,J710.751J
• Wikipedia: Mitoxantrone
• Wikidata: Q239426
• NCI Thesaurus Code: C62050
• RXCUI: 7005
• Pharos Ligand ID: 1AZCKZ8DNQYZ
• Metabolomics Workbench ID: 43418
• ChEMBL ID: CHEMBL58
• Mol file: 65271-80-9.mol

Synonyms:Acetate, Mitoxantrone;CL 232325;CL-232325;CL232325;DHAQ;Hydrochloride, Mitoxantrone;Mitoxantrone;Mitoxantrone Acetate;Mitoxantrone Hydrochloride;Mitozantrone;Mitroxone;Novantron;Novantrone;NSC 279836;NSC 287836;NSC 299195;NSC 301739;NSC 301739D;NSC-279836;NSC-287836;NSC-299195;NSC-301739;NSC-301739D;NSC279836;NSC287836;NSC299195;NSC301739;NSC301739D;Onkotrone;Pralifan;Ralenova

Chemical Property of Mitoxantrone

Chemical Property:

• Appearance/Colour: Dark blue crystalline solid
• Vapor Pressure: 2.05E-27mmHg at 25°C
• Melting Point: 170-174 °C
• Refractive Index: 1.709
• Boiling Point: 805.743 °C at 760 mmHg
• PKA: pKa 5.99 (Uncertain);8.13 (Uncertain)
• Flash Point: 441.098 °C
• PSA: 163.18000
• Density: 1.45 g/cm³
• LogP: 0.78860
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Sparingly), Water (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 444.20088463
• Heavy Atom Count: 32
• Complexity: 571

Purity/Quality:

≥98% ^*data from raw suppliers

Mitoxantrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T,T+
• Statements: 46-61-26/27/28
• Safety Statements: 53-36/37/39-45-22

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents; Multiple Sclerosis Agents
• Canonical SMILES: C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO
• Recent ClinicalTrials: A Global Study of Midostaurin in Combination With Chemotherapy to Evaluate Safety, Efficacy and Pharmacokinetics in Newly Diagnosed Pediatric Patients With FLT3 Mutated AML
• Recent EU Clinical Trials: Venetoclax plus Azacitidine versus Standard intensive Chemotherapy for Patients with newly diagnosed Acute Myeloid Leukemia (AML) and NPM1 Mutations eligible for intensive Treatment (VINCENT)
• Recent NIPH Clinical Trials: A clinical trial of risk-stratification and gemtuzumab ozogamicin combined post-induction chemotherapy for children with AML
• Uses: Mitoxantrone is a DNA intercalating drug. Mitoxantrone inhibits DNA synthesis. Mitoxantrone is used as an anti-cancer agent.
• Indications: Mitoxantrone (Novantrone) is a synthetic anthraquinone that is structurally and mechanistically related to the anthracyclines. It intercalates with DNA and produces single- strand DNA breakage. It is cross-resistant with doxorubicin in multidrug-resistant cells and in patients who have failed to respond to doxorubicin therapy. Mitoxantrone is active against breast carcinomas, leukemias, and lymphomas. Its antitumor efficacy in patients with breast cancer is slightly lower than that of doxorubicin. Its major toxicity is myelosuppression; mucositis and diarrhea also may occur. Mitoxantrone produces less nausea, alopecia, and cardiac toxicity than does doxorubicin.
• Therapeutic Function: Antineoplastic
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugs Other antineoplastic agents: enhanced myelosuppression - when used in combination reduce mitoxantrone dose by 2-4 mg/m2. Antipsychotics: avoid with clozapine, increased risk of agranulocytosis. Cardiotoxic drugs: increased risk of cardiac toxicity. Ciclosporin: excretion of mitoxantrone reduced. Live vaccines: risk of generalised infections - avoid.

Technology Process of Mitoxantrone

There total 7 articles about Mitoxantrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.0%

1,4,5,8-tetrahydroxy-2,3-dihydro-9,10-anthracenedione (81-59-4) + 2-(2-Aminoethylamino)ethanol (111-41-1) → novantrone (65271-80-9,70945-62-9)

Guidance literature:

In 1,4-dioxane; at 53 ℃; for 2.2h; Temperature; Inert atmosphere;

Reference yield: 38.0%

1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione (131401-54-2) + 2-(2-Aminoethylamino)ethanol (111-41-1) → novantrone (65271-80-9,70945-62-9)

Guidance literature:

With pyridine;

DOI:10.1002/cmdc.201500274

Reference yield: 11.0%

1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione (131401-54-2) + 2-(2-Aminoethylamino)ethanol (111-41-1) → novantrone (65271-80-9,70945-62-9) + 6-Fluoro-8,11-dihydroxy-4-(2-hydroxy-ethyl)-1,2,3,4-tetrahydro-1,4-diaza-benzo[a]anthracene-7,12-dione (134529-38-7)

Guidance literature:

In pyridine; for 50h; Ambient temperature;

DOI:10.1021/jm00112a009

upstream raw materials:

1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione

2-(2-Aminoethylamino)ethanol

5,8-Dihydroxy-1,4-bis-[2-(2-hydroxy-ethylamino)-ethylamino]-2,3-dihydro-anthraquinone

1,4,5,8-tetrahydroxy-2,3-dihydro-9,10-anthracenedione

Downstream raw materials:

novantrone

Refernces

• 1、 -. "Semi-synthesis method for mitoxantrone". Paragraph 0023; 0025-0077. . Retrieved 2018/09/08.
• 2、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.