ChemicalBook > Product Catalog > API > Antineoplastic agents > Antitumor Adjuvant Drugs > Mitoxantrone
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. -20°C Freezer
- pkapKa 5.99 (Uncertain);8.13 (Uncertain)
- CAS DataBase Reference65271-80-9(CAS DataBase Reference)
- IARC2B (Vol. 76) 2000
Mitoxantrone Usage And Synthesis
- Chemical PropertiesDark Blue Crystalline Solid
- OriginatorNovantrone,Immunex Corporation
- UsesA DNA intercalating drug. Inhibits DNA synthesis. Used as an anti-cancer agent
- UsesMitoxantrone is a DNA intercalating drug. Mitoxantrone inhibits DNA synthesis. Mitoxantrone is used as an anti-cancer agent.
- IndicationsMitoxantrone (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.
- Manufacturing ProcessA 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
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 nameNovantrone (Serono).
- Therapeutic FunctionAntineoplastic
- Mechanism of actionThe 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.
- Chemical SynthesisMitoxantrone, 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 TreatmentsMitoxantrone 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.
- 1,8-diaminobromo-4,5-dihydroxyanthraquinone 1,2,3,4-TETRAFLUORO-5,8-DIHYDROXYANTHRAQUINONE 1,8-diamino-2,7-dibromo-4,5-dihydroxyanthraquinone 6,7-DICHLORO-1,4-DIHYDROXYANTHRAQUINONE, 97,6,7-dichloro-1,4-dihydroxyanthraquinone MITOXANTRONE = 1,4-DIHYDROXY-5,8-BIS[[2-(2-HYDROXYETHYL)-AMINO]ETHYLAMINO]9,10-ANTHRACENDIONE DIHYDROCHLORIDE 1,4-bis[[4-(1,1-dimethylethyl)phenyl]amino]-5,8-dihydroxyanthraquinone MITOXANTRONE, [3H]-,MITOXANTRONE, [3H(G)] Mitoxantrone CHRYSAZIN(RG) 1-Hydroxyethylidene-1,1-diphosphonic acid Hydroxyethyl starch Tris Base 3-Diethylaminophenol Anthracene Mitoxantrone2Hcl,MITOXANTRONE HCL USP,MITOXANTRONE HCL,MITOXANTRONE HYDROCHLORIDE SALT,MITOXANTRONE HYDROCHLORIDE,MITOXANTRONE DIHYDROCHLORIDE Anthraquinone Hydroxyethyl Cellulose Mitoxantrone HCL for Injection (Lyophilized Power)
- Company Name:Hubei kangmingde Pharmaceutical Chemical Co., Ltd Gold
- Tel:15008015258 027-89771658-
- Company Name:Shanghai Fulland Pharmaceuticals Ltd Gold
- Tel:18964441746 021-50432069-
- Company Name:J & K SCIENTIFIC LTD.
- Tel:400-666-7788 010-82848833-
- Company Name:TCI (Shanghai) Development Co., Ltd.
- Tel:021-67121386 / 800-988-0390
- Company Name:LGM Pharma