SML2577
Pixantrone dimaleate
≥98% (HPLC)
Synonym(s):
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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About This Item
Empirical Formula (Hill Notation):
C17H19N5O2 · C8H8O8
CAS Number:
Molecular Weight:
557.51
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
desiccated
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
purple to dark blue
solubility
H2O: 2 mg/mL, clear
storage temp.
2-8°C
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
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.
Signal Word
Warning
Hazard Codes
Precautionary Statements
Hazard Classifications
Muta. 2 - Repr. 2
Storage Class
13 - Non Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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