SML2577

Pixantrone dimaleate

Name: Pixantrone dimaleate
Brand: SIGMA

≥98% (HPLC)

别名:

2-Azaanthracene-9,10-dione dimaleate, 6,9-Bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione dimaleate, BBR 2778, BBR-2778, BBR2778, Pixantrone maleate

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关于此项目

经验公式（希尔记法）:

C₁₇H₁₉N₅O₂ · C₈H₈O₈

化学文摘社编号:

144675-97-8

分子量:

557.51

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00920108

主要文件

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SMILES string

N(CCN)c1c2c(c(cc1)NCCN)C(=O)c3c(cncc3)C2=O.OC(=O)\C=C\C(=O)O.OC(=O)\C=C\C(=O)O

InChI

1S/C17H19N5O2.2C4H4O4/c18-4-7-21-12-1-2-13(22-8-5-19)15-14(12)16(23)10-3-6-20-9-11(10)17(15)24;2*5-3(6)1-2-4(7)8/h1-3,6,9,21-22H,4-5,7-8,18-19H2;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+

InChI key

SVAGFBGXEWPNJC-LVEZLNDCSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

purple to dark blue

solubility

H₂O: 2 mg/mL, clear

storage temp.

2-8°C

Biochem/physiol Actions

Anthracycline DNA-intercalating topoisomerase II poison with enhanced antitumor activity and reduced cardiotoxicity than mitoxantrone and doxorubicin.

Pixantrone (BBR 2778) is an aza-anthracenedione with enhanced antitumor activity due to its DNA-intercalating and topoisomerase II-poisoning activity. Pixantrone shows no signs of acute or delayed cardiotoxicity seen with anthracyclines mitoxantrone and doxorubicin (DOX), while exhibiting comparable in vivo efficacy against solid tumors in mice. Tests conducted on human myocardial strips ex vivo shows that not only pixantrone does not form superoxide anion and hydrogen peroxide (O₂^•− and H₂O₂) seen with DOX due to redox activation, pixantrone and its metabolites, especially N-dealkylated, show competitive inhibition against DOX reduction. While mitoxantrone does not form O₂^•− and H₂O₂ on its own, it synergizes with DOX to form more O₂^•− and H₂O₂, whose formation and subsequent production of the long-lived metabolite doxorubicinol contribute to DOX cardiotoxicity.