Mitoxantrone

ChemicalBook > CAS DataBase List > Mitoxantrone

Product Name: Mitoxantrone
CAS No.: 65271-80-9
Chemical Name: Mitoxantrone
Synonyms: itoxantrone;mitoxanthrone;dihydroxyanthraquinone;Ralenova;NSC-27983;nsc279836;MITOXANTRONE;MITOXANTRONUM;MitoxantroneBase;PharmasubstanceEP4
CBNumber: CB1246423
Molecular Formula: C22H28N4O6
Formula Weight: 444.48
MOL File: 65271-80-9.mol

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Mitoxantrone Property

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

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H351Suspected of causing cancer

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical

Product number: M3133
Product name: Mitoxantrone
Purity: >97.0%(HPLC)
Packaging: 200mg
Price: $147
Updated: 2024/03/01

TCI Chemical

Product number: M3133
Product name: Mitoxantrone
Purity: >97.0%(HPLC)
Packaging: 1g
Price: $441
Updated: 2024/03/01

Usbiological

Product number: 017685
Product name: Mitoxantrone
Packaging: 50mg
Price: $460
Updated: 2021/12/16

TRC

Product number: M373425
Product name: Mitoxantrone
Packaging: 1g
Price: $285
Updated: 2021/12/16

Usbiological

Product number: M4017-01
Product name: Mitoxantrone
Packaging: 50mg
Price: $297
Updated: 2021/12/16

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Mitoxantrone Chemical Properties,Usage,Production

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

Mitoxantrone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Mitoxantrone manufacturers

Hebei Lingding Biotechnology Co., Ltd.

Product: Mitoxantrone 65271-80-9
Price: US $50.00-50.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 9000kg/per week
Release date: 2024-02-03

Hebei Lingding Biotechnology Co., Ltd.

Product: Mitoxantrone 65271-80-9
Price: US $50.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 9000kg/per week
Release date: 2021-09-16

Zhuozhou Wenxi import and Export Co., Ltd

Product: Mitoxantrone 65271-80-9
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-08-11

65271-80-9, MitoxantroneRelated Search:

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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

PharmasubstanceEP4

1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione

NSC-27983

9,10-Anthracenedione, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-

1,4-dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthrace nedimitoxantrone

MITOXANTRONUM AND THE INTERMEDIATES

Ralenova

Mitoxantrone 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]-anthracene-9,10-dione

itoxantrone

5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxy-anthraquinon

5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxyanthraquinone

9,10-anthracenedione,1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)a

dihydroxyanthraquinone

mitoxanthrone

nsc279836

Mitoxantrone Control

1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthraquinone

Mitoxantrone USP/EP/BP

Mitoxantrone (Base,Hcl)

Mitoxantrone (mitozantrone)

65271-80-9

C22H28N4O6

Apoptosis and Cell Cycle

BioChemical

Cell Biology

Cell Signaling and Neuroscience

DNA Intercalators and Crosslinkers

DNA metabolism

Inhibitors

Anti-cancer&immunity

Pharmaceutical material and intermeidates

Intermediates & Fine Chemicals

Pharmaceuticals

APIs

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