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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
Molecular Weight:
444.48
MDL Number:
MFCD00242942
MOL File:
65271-80-9.mol
Last updated:2024-02-04 22:50:33

Mitoxantrone 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)
FDA UNII BZ114NVM5P
ATC code L01DB07
IARC 2B (Vol. 76) 2000

Pharmacokinetic data

Protein binding 78%
Excreted unchanged in urine 7%
Volume of distribution 1000 L/m2(L/kg)
Biological half-life 5-18 days / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS09
Signal word  Warning
Hazard statements  H351-H411
Precautionary statements  P201-P202-P281-P308+P313-P405-P501
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
NFPA 704
0
3 0

Mitoxantrone price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical M3133 Mitoxantrone >97.0%(HPLC) 65271-80-9 200mg $147 2024-03-01 Buy
TCI Chemical M3133 Mitoxantrone >97.0%(HPLC) 65271-80-9 1g $441 2024-03-01 Buy
Usbiological 017685 Mitoxantrone 65271-80-9 50mg $460 2021-12-16 Buy
TRC M373425 Mitoxantrone 65271-80-9 1g $285 2021-12-16 Buy
Usbiological M4017-01 Mitoxantrone 65271-80-9 50mg $297 2021-12-16 Buy
Product number Packaging Price Buy
M3133 200mg $147 Buy
M3133 1g $441 Buy
017685 50mg $460 Buy
M373425 1g $285 Buy
M4017-01 50mg $297 Buy

Mitoxantrone Chemical Properties,Uses,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.

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.

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

81-59-4
111-41-1
65271-80-9
Synthesis of Mitoxantrone from 2,3-dihydro-1,4,5,8-tetrahydroxyanthraquinone and 2-(2-Aminoethylamino)ethanol

Mitoxantrone Preparation Products And Raw materials

Global( 218)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Lingding Biotechnology Co., Ltd.
+86-18031140164 +86-19933155420 erin@hbldbiotech.com China 881 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Accela ChemBio Inc.
(+1)-858-699-3322 info@accelachem.com United States 19965 58
BOC Sciences
+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Shaanxi Dideu Medichem Co. Ltd
+86-29-87569266 15319487004 1015@dideu.com China 2263 58
ANHUI WITOP BIOTECH CO., LTD
+8615255079626 eric@witopchemical.com China 23556 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29831 58
AFINE CHEMICALS LIMITED
0571-85134551 info@afinechem.com CHINA 15377 58
Finetech Industry Limited
+86-27-87465837 +8618971612321 info@finetechnology-ind.com China 9589 58
Baoji Guokang Bio-Technology Co., Ltd.
0917-3909592 13892490616 gksales1@gk-bio.com China 9340 58

View Lastest Price from Mitoxantrone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Mitoxantrone pictures 2024-02-03 Mitoxantrone
65271-80-9
US $50.00-50.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
Mitoxantrone pictures 2021-10-20 Mitoxantrone
65271-80-9
US $50.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
Mitoxantrone pictures 2021-08-12 Mitoxantrone
65271-80-9
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Mitoxantrone pictures
  • Mitoxantrone
    65271-80-9
  • US $50.00-50.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.
  • Mitoxantrone pictures
  • Mitoxantrone
    65271-80-9
  • US $50.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.
  • Mitoxantrone pictures
  • Mitoxantrone
    65271-80-9
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
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 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 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) dihydroxyanthraquinone itoxantrone mitoxanthrone 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 API