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M6545

Sigma-Aldrich

Mitoxantrone dihydrochloride

≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C22H28N4O6 · 2HCl
CAS Number:
70476-82-3
Molecular Weight:
517.40
EC Number:
274-619-1
MDL number:
MFCD00242943
UNSPSC Code:
12352005
PubChem Substance ID:
24278562
NACRES:
NA.25

Assay

≥97% (HPLC)

SMILES string

Cl[H].Cl[H].OCCNCCNc1ccc(NCCNCCO)c2C(=O)c3c(O)ccc(O)c3C(=O)c12

InChI

1S/C22H28N4O6.2ClH/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;2*1H

InChI key

ZAHQPTJLOCWVPG-UHFFFAOYSA-N

Gene Information

human ... TOP2A(7153)

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Application

Mitoxantrone dihydrochloride has been used:
  • to induce calreticulin surface expression in cells
  • as a genotoxin agent
  • as a topoisomerase inhibitor

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.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H360

Hazard Classifications

Muta. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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FitzGerald J
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Peritoneal carcinomatosis is a common cause of death in pancreatic cancer patients. In this metastatic stage of the disease, few patients show a sustained response to therapy. In the palliative situation, targeted and compartment restricted delivery of drugs offers the
James M Stankiewicz et al.
Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics, 10(1), 77-88 (2012-12-29)
Immunosuppressives have been used in multiple sclerosis (MS) since 1966. Today, we have many treatments for the relapsing forms of the disease, including 8 US Food and Drug Administration-approved therapies, with more soon to be introduced. Given the current treatment
Chyuan-Chuan Wu et al.
Nucleic acids research, 41(22), 10630-10640 (2013-09-17)
Type II topoisomerases (Top2s) alter DNA topology via the formation of an enzyme-DNA adduct termed cleavage complex, which harbors a transient double-strand break in one DNA to allow the passage of another. Agents targeting human Top2s are clinically active anticancer
Yuting Ma et al.
The Journal of experimental medicine, 208(3), 491-503 (2011-03-09)
By triggering immunogenic cell death, some anticancer compounds, including anthracyclines and oxaliplatin, elicit tumor-specific, interferon-γ-producing CD8(+) αβ T lymphocytes (Tc1 CTLs) that are pivotal for an optimal therapeutic outcome. Here, we demonstrate that chemotherapy induces a rapid and prominent invasion
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