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ChemicalBook--->CAS DataBase List--->65271-80-9

65271-80-9

65271-80-9 Structure

65271-80-9 Structure
IdentificationMore
[Name]

Mitoxantrone
[CAS]

65271-80-9
[Synonyms]

1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]-anthracene-9,10-dione
MITOXANTRONE
1,4-dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthracenedi
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
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
Mitoxantrone (base and/or unspecified salts)
MITOXANTRONUM
1,4-Dihydroxy-5,8-bis[2-[(2-hydroxyethyl)amino]ethylamino]-9,10-anthraquinone
[EINECS(EC#)]

1533716-785-6
[Molecular Formula]

C22H28N4O6
[MDL Number]

MFCD00242942
[Molecular Weight]

444.48
[MOL File]

65271-80-9.mol
Chemical PropertiesBack Directory
[Appearance]

Dark Blue Crystalline Solid
[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)
[form ]

Solid
[pka]

pKa 5.99 (Uncertain);8.13 (Uncertain)
[color ]

Dark Blue to Black
[Usage]

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

InChI=1S/C22H28N4O6/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
[InChIKey]

KKZJGLLVHKMTCM-UHFFFAOYSA-N
[SMILES]

C1(O)=C2C(C(=O)C3=C(C2=O)C(NCCNCCO)=CC=C3NCCNCCO)=C(O)C=C1
[CAS DataBase Reference]

65271-80-9(CAS DataBase Reference)
[IARC]

2B (Vol. 76) 2000
Safety DataBack Directory
[Hazard Codes ]

T,T+
[Risk Statements ]

R61:May cause harm to the unborn child.
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S53:Avoid exposure-obtain special instruction before use .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S22:Do not breathe dust .
[WGK Germany ]

3
[RTECS ]

CB5748500
[HS Code ]

2922.50.2500
Hazard InformationBack Directory
[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.
[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.
[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.
[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.
[Clinical Use]

#N/A
[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),

Synthesis_65271-80-9

[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
[storage]

-20°C, protect from light
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