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Mitoxantrone
Mitoxantrone
2D structure of mitoxantrone
Mitoxantrone
3D structure of mitoxantrone

Synonyms

CL-232315, DHAD, Dihydroxyanthracenedione, Mitozantrone, NSC-301739

Brand names

Novantrone, Onkotrone

IUPAC name

IUPAC name
1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione

ChemSpider

4067

DrugBank

DB01204

PubChem

4212

PDB fields

PDBs
2FUM (RCSB, PDBe; X-ray)
2KGP (RCSB, PDBe; NMR)
4G0V (RCSB, PDBe; X-ray)
4I41 (RCSB, PDBe; X-ray)

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

InChIKey
KKZJGLLVHKMTCM-UHFFFAOYSA-N

SMILES

SMILES
C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO
(Jmol 3D structure)

Formula

C22H28N4O6

Mol. mass

444.481 g/mol

MeSH

D008942


Mitoxantrone is an anthracenedione antibiotic that intercalates DNA, inhibits topoisomerase II and produces immunosuppressive effects, including via inhibiting the proliferation of macrophages, T-cells and B-cells.[1] It was first developed for the treatment of acute myeloid leukaemia in the 1980s, but was later developed for the treatment of prostate cancer and multiple sclerosis.[1]


Intercalation of DNA/RNA
3000px DNA intercalation by mitoxantrone based on 4G0V

Intercalation of DNA by mitoxantrone

3000px Diagram of mitoxantrone binding to RNA based on 2KGP

Intercalation of RNA by mitoxantrone



External linksEdit

Reference listEdit

  1. 1.0 1.1 Neuhaus, O; Kieseier, BC; Hartung, HP (15 August 2007). "Pharmacokinetics and pharmacodynamics of the interferon-betas, glatiramer acetate, and mitoxantrone in multiple sclerosis.". Journal of the Neurological Sciences 259 (1-2): 27–37. PMID 17391705. doi:10.1016/j.jns.2006.05.071. 

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