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
• Empirical Formula (Hill Notation): C₁₇H₁₉N₅O₂ · C₈H₈O₈
• CAS Number: 144675-97-8
• Molecular Weight: 557.51
• MDL number: MFCD00920108
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H341,H361d
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Muta. 2 - Repr. 2
• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable