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Mitoxantrone

Mitoxantrone Structure
Mitoxantrone structure
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
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-16 07:06:08
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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
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)
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)  Health Hazard (GHS08)Environment (GHS09)
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(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical M3133 Mitoxantrone >97.0%(HPLC) 65271-80-9 200mg $166 2026-04-30 Buy
TCI Chemical M3133 Mitoxantrone >97.0%(HPLC) 65271-80-9 1g $497 2026-04-30 Buy
Biosynth FD26022 Mitoxantrone 65271-80-9 250mg $190 2026-06-04 Buy
Biosynth FD26022 Mitoxantrone 65271-80-9 500mg $290 2026-06-04 Buy
Biosynth FD26022 Mitoxantrone 65271-80-9 1000mg $480 2026-06-04 Buy
Product number Packaging Price Buy
M3133 200mg $166 Buy
M3133 1g $497 Buy
FD26022 250mg $190 Buy
FD26022 500mg $290 Buy
FD26022 1000mg $480 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.

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),

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

References

[1] Patent: CN108395379, 2018, A. Location in patent: Paragraph 0023; 0025-0077

Mitoxantrone synthesis

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

Raw materials

Dihydro-1,4,5,8-tetrahydroxyanthraquinone 2-(2-Aminoethylamino)ethanol Chloranil N,N,N',N'-Tetramethylethylenediamine 2,3-dihydro-1,4,5,8-tetrahydroxyanthraquinone

Preparation Products

Mitoxantrone Suppliers

Global( 258)Suppliers
Supplier Tel Email Country ProdList Advantage
Hubei kangen Pharmaceutical Chemical Co., Ltd 180-64105258 18064105258 3357312443@qq.com China 695 56
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Beijing HwrkChemical Technology Co., Ltd 89508211 18501085097 sales.bj@hwrkchemical.com China 9407 55
Energy Chemical 400-0056266 sales8178@energy-chemical.com China 44850 61
Adamas Reagent, Ltd. 400-6009262 15618770481 yhx@titansci.com China 14098 59
LGM Pharma 1-(800)-881-8210 inquiries@lgmpharma.com United States 2110 70
Chemsky（shanghai）International Co.,Ltd. 021-50135380 shchemsky@sina.com China 32273 50
Syntechem Co.,Ltd info@syntechem.com China 12973 57
Sinopharm Chemical Reagent Co,Ltd. 86-21-63210123 sj_scrc@sinopharm.com China 9791 79
Supplier Advantage
Hubei kangen Pharmaceutical Chemical Co., Ltd 56
J & K SCIENTIFIC LTD. 76
TCI (Shanghai) Development Co., Ltd. 81
Beijing HwrkChemical Technology Co., Ltd 55
Energy Chemical 61
Adamas Reagent, Ltd. 59
LGM Pharma 70
Chemsky（shanghai）International Co.,Ltd. 50
Syntechem Co.,Ltd 57
Sinopharm Chemical Reagent Co,Ltd. 79

Related articles

View Lastest Price from Mitoxantrone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Mitoxantrone USP/EP/BP pictures 2026-08-20 Mitoxantrone USP/EP/BP
65271-80-9
 $1.10 1g 99.9% 100 Tons Min Dideu Industries Group Limited
Mitoxantrone pictures 2026-07-15 Mitoxantrone
65271-80-9
 $33.00-65.00 97.02% 10g TargetMol Chemicals Inc.
Mitoxantrone pictures 2021-08-12 Mitoxantrone
65271-80-9
 $10.00-15.00 1KG 99%+ HPLC Zhuozhou Wenxi import and Export Co., Ltd
  • Mitoxantrone pictures
  • Mitoxantrone
    65271-80-9
  • $33.00-65.00
  • 97.02%
  • TargetMol Chemicals Inc.
  • Mitoxantrone pictures
  • Mitoxantrone
    65271-80-9
  • $10.00-15.00
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Mitoxantrone Spectrum

Mitoxantrone(65271-80-9)1HNMR

65271-80-9(Mitoxantrone)Related Search:

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Hydroxyethyl Cellulose Sodium isethionate Tris(hydroxymethyl)aminomethane Alizarin Mitoxantrone HCL for Injection (Lyophilized Power)
2-Bromo-1,8-diamino-4,5-dihydroxyanthraquinone 4,8-DIAMINO-1,5-DIHYDROXYANTHRAQUINONE-2,6-DISULFONIC ACID, DISODIUM SALT 4,5-diamino-1,8-dihydroxyanthraquinon 5,8-DICHLORO-1,4-DIHYDROXYANTHRAQUINONE Disperse Blue 56
ACID GREEN 41 Mitoxantrone hydrochloride Alizarin Complexone

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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 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) 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione Mitoxantrone, 10 mM in DMSO 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