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70476-82-3

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Identification

Name
Mitoxantrone hydrochloride
CAS
70476-82-3
Synonyms
1,4-DIHYDROXY-5,8-BIS[2-[(2-HYDROXYETHYL)AMINO]ETHYL]AMINO]-9,10-ANTHRACENEDIONE DIHYDROCHLORIDE
1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthraquinone dihydrochloride
DHAQ
DHAQ DIHYDROCHLORIDE
MITOXANTHRONE HCL
MITOXANTRONE DIHYDROCHLORIDE
MITOXANTRONE HCL
MITOXANTRONE HYDROCHLORIDE
MITOXANTRONE HYDROCHLORIDE SALT
mitozantrone hydrochloride
novantrone
1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-anthracenedion
cl232315
MITOXANTRONE HCL USP
Mitoxantrone2Hcl
MitoxantroneHclEp5
1,4-Dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthrachinondihydrochlorid
Mitoxantron HCl
1,4-DIHYDROXY-5,8-BIS-[2-(2-HYDROXYETHYLAMINO)ETHYLAMINO]ANTHRAQUINONE 2HCL
1,4-Dihydroxy-5,8-bis-[2-(2-
EINECS(EC#)
274-619-1
Molecular Formula
C22H30Cl2N4O6
MDL Number
MFCD00242943
Molecular Weight
517.4
MOL File
70476-82-3.mol

Chemical Properties

Appearance
Dark blue, electrostatic, hygroscopic powder.
Melting point 
203-205 C
mp 
203-205 C
storage temp. 
2-8°C
solubility 
Sparingly soluble in water, slightly soluble in methanol, practically insoluble in acetone.
form 
neat
Water Solubility 
Soluble to 5 mM in water and to 75 mM in DMSO
InChIKey
ZAHQPTJLOCWVPG-UHFFFAOYSA-N
CAS DataBase Reference
70476-82-3(CAS DataBase Reference)
EPA Substance Registry System
70476-82-3(EPA Substance)

Safety Data

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 .
RIDADR 
3249
WGK Germany 
3

RTECS 
CB5748500

HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29146100
Hazardous Substances Data
70476-82-3(Hazardous Substances Data)

Hazard Information

Description
Mitoxantrone hydrochloride is the first of the synthetic anthracenediones related to doxorubicin to reach the marketplace. Mitoxantrone is useful in the treatment of advanced localized and metastatic mammary carcinomas. It is reported to be less cardiotoxic than doxorubicin.
Description
Mitoxantrone is an anthraquinone that intercalates in DNA and inhibits topoisomerase II (IC50 = 5.3 μM), thus inhibiting cell proliferation. It also inhibits HIV-1 integrase (IC50 = 3.8 μM). Mitoxantrone is exported from cells in an ATP- and glutathione-dependent manner by multidrug resistance protein-1. Formulations containing mitoxantrone have been used in the treatment of cancer and multiple sclerosis.
Chemical Properties
Dark blue, electrostatic, hygroscopic powder.
Originator
Lederle (USA)
Uses
Mitoxanthrone hydrochloride USP (Novantrone) is used to traet acute nonlymphocytic leukemia, including myelogenous promyelocytic, monocytic, and erythroid acute leukemias.
Uses
Mitoxantrone dihydrochloride is an antiviral, antibacterial, antiprotozoal, immunomodulating, and antineoplastic cytostatic anthraquinone derivative. Induces DNA damage by intercalating into DNA and inhibiting Topo II (topoisomerase II). Mitoxantrone dihydrochloride induces interstrand DNA cross-links and DNA-protein cross-links in cellular systems. Mitoxantrone dihydrochloride has recently been shown to be an inhibitor of DNA methylation.
Uses
analgesic, antipyretic
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
General Description
Mitoxantrone is supplied as a blue aqueous solution in 10-and 20-mg vials for IV administration in the treatment of acute lymphoid leukemia, acute myeloid leukemia, breastcancer, prostate cancer, non-Hodgkin’s lymphoma, andmultiple sclerosis. The mechanisms of resistance are thesame as those seen for the anthracyclines. The distributionhalf-life is 1.1 to 3.1 hours, and the drug has a large volumeof distribution (11 L/kg). The elimination half-life rangedfrom 23 to 215 hours, and elimination was primarily via thebile. Metabolism of the agent involves oxidation of the sidechainalcohols to give the monocarboxylic and dicarboxylicacids.Other toxicities are those seen for the anthracyclinesand include myelosuppression, nausea, vomiting, mucositis,diarrhea, and alopecia. The intense color of the parent drugand metabolites may turn the urine blue.
Biochem/physiol Actions
Mitoxantrone is a cytostatic anthracenedione that intercalates in DNA and increases the incidence of double-strand breaks by stabilizing the cleavable complex of topoisomerase II and DNA. Mitoxantrone also displays broad immunosuppressive activity inhibiting proliferation of all classes of lymphocytes and inducing apoptosis of antigen-presenting T cells. It used clinically as a chemotherapeutic agent against leukemias and solid tumors and as an immune system modulator in multiple sclerosis.
Clinical Use
Mitoxantrone is used in combination with other agents during the initial treatment of acute nonlymphocytic leukemia and hormone-refractory prostate cancer. Recent studies have shown that mitoxantrone also decreases the rate of relapse and disease progression in patients with multiple sclerosis. Although too toxic for use in patients with primary progressive disease, it is available for the treatment of chronic progressive, progressive relapsing, or deteriorating relapsing-remitting multiple sclerosis.
Metabolism
Mitoxantrone excretion primarily is biliary. Both the unchanged drug and inactive metabolites resulting from N-dealkylation, deamination, and oxidation of the resultant aldehyde to the carboxylic acid are observed. Both arms of the structure can be metabolized, leading to mono- or dicarboxylic acid metabolites, which are excreted as the glucuronide conjugate. The conjugated metabolites are an intense, dark blue in color and will result in blue-green urine.

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