Basic information Safety Supplier Related
ChemicalBook >  Product Catalog >  API >  Antineoplastic agents >  Antitumor Adjuvant Drugs >  Mitoxantrone

Mitoxantrone

Basic information Safety Supplier Related

Mitoxantrone Basic information

Product Name:
Mitoxantrone
Synonyms:
  • MITOXANTRONE
  • 1,4-dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthracenedi
  • 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]-anthracene-9,10-dione
  • Mitoxantrone (base and/or unspecified salts)
  • MITOXANTRONUM
  • 1,4-Dihydroxy-5,8-bis[2-[(2-hydroxyethyl)amino]ethylamino]-9,10-anthraquinone
  • MitoxantroneBase
  • Mitoxantrone Hcl 70476-82-3 / Base
CAS:
65271-80-9
MF:
C22H28N4O6
MW:
444.48
EINECS:
1533716-785-6
Product Categories:
  • Inhibitors
  • Anti-cancer&immunity
  • Pharmaceutical material and intermeidates
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • APIs
  • API
Mol File:
65271-80-9.mol
More
Less

Mitoxantrone Chemical Properties

Melting point:
170-1740C
Boiling point:
554.47°C (rough estimate)
Density 
1.3049 (rough estimate)
refractive index 
1.6500 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
DMSO (Slightly), Methanol (Sparingly), Water (Slightly)
pka
pKa 5.99 (Uncertain);8.13 (Uncertain)
form 
Solid
color 
Dark Blue to Black
CAS DataBase Reference
65271-80-9(CAS DataBase Reference)
IARC
2B (Vol. 76) 2000
More
Less

Safety Information

Hazard Codes 
T,T+
Risk Statements 
46-61-26/27/28
Safety Statements 
53-36/37/39-45-22
WGK Germany 
3
RTECS 
CB5748500
HS Code 
2922.50.2500
More
Less

Mitoxantrone Usage And Synthesis

Chemical Properties

Dark Blue Crystalline Solid

Originator

Novantrone,Immunex Corporation

Uses

A DNA intercalating drug. Inhibits DNA synthesis. Used as an anti-cancer agent

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.

Definition

ChEBI: Mitoxantrone is 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. It has a role as an antineoplastic agent and an analgesic.

Manufacturing Process

A suspension of 12.5 g of 2-(2-aminoethylamino)ethanol in 40 ml of N,N,N',N'-tetramethylethylenediamine is stirred and de-aerated by bubbling nitrogen in for 15 min. A 10.97 g of leuco-1,4,5,8-tetrahydroxyanthraquinone is gradually added with stirring. The suspension is heated and stirred under nitrogen at 50-52°C for 5 hours. The mixture is allowed to stand and cool under nitrogen for 12 hours. The solid is collected by decantation, macerated in ethanol, collected and washed with ethanol giving 15.06 g of the desired product leuco-1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8- dihydroxyanthraquinone as a green-gray solid, melting point 129-131°C.
Chloranil oxidation. To 17.86 g of a suspension of the leuco-1,4-bis[2-(2- hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone (0.03 mole) in 2- methoxyethanol was added gradually with stirring 15 ml of 8 N ethanolic hydrogen chloride. The system was chilled with an ice bath and stirred as 7.50 g (0.0305 mole) of chloranil powder was gradually added. The mixture was stirred overnight at room temperature and diluted with 600 ml of ether. The solid was collected and washed with tetrahydrofuran. Yield of 1,4-bis[2-(2- hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone dihydrochloride 21.34 g, melting point 203-205°C (without recrystallisation).

brand name

Novantrone (Serono).

Therapeutic Function

Antineoplastic

Mechanism of action

The mechanism of its action is not completely understood, although it is presumed, that mitoxantrone acts by binding with DNA, thus disturbing the twisting process of the chains. It is used intravenously for treating severe nonlymphatic leukemia, breast cancer, and so on. A synonym of this drug is novantrone.

Synthesis

Mitoxantrone, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl) amino) ethyl]amino]]-9,10-anthracendione (30.6.3), is structurally related to the antibiotic doxorubicine. It is synthesized from danthron (1,8-dihydroxyanthraquinone), which when reacted with nitric acid, and then a mixture of sodium sulfide and thiosulfate in a base, is transformed to 1,4,5,8-tetrahydroxyanthraquinone (30.6.2). Reacting this with 2-aminoethylaminoethanol in the presence of chloranyl (2,3,5,6-tetrachlorobenzoquinone-1,4) gives the desired mitoxantrone (30.6.3),

Veterinary Drugs and Treatments

Mitoxantrone may be useful in the treatment of several neoplastic diseases in dogs and cats, including lymphosarcoma mammary adenocarcinoma, squamous cell carcinoma, renal adenocarcinoma, fibroid sarcoma, thyroid or transitional cell carcinomas, and hemangiopericytoma.
Because renal clearance of the drug is minimal (10%), it may be administered to cats with renal insufficiency much more safely than doxorubicin.

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.

Metabolism

Extensive metabolism in the liver. Excretion is predominantly via the bile and faeces. 5-10% of a dose is excreted in the urine and 13-25% in the faeces, within 5 days

MitoxantroneSupplier

Hubei kangen Pharmaceutical Chemical Co., Ltd Gold
Tel
133-97105803 13397105803
Email
3357312443@qq.com
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Email
jkinfo@jkchemical.com
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Email
Sales-CN@TCIchemicals.com
Energy Chemical
Tel
021-021-58432009 400-005-6266
Email
sales8178@energy-chemical.com
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Email
zhangsn@titansci.com