SML2577

Pixantrone dimaleate

≥98% (HPLC)

• Synonyme(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
• Formule empirique (notation de Hill) : C₁₇H₁₉N₅O₂ · C₈H₈O₈
• Numéro CAS: 144675-97-8
• Poids moléculaire : 557.51
• Numéro MDL: MFCD00920108
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Essai: ≥98% (HPLC)
• Forme: powder
• Conditions de stockage: desiccated
• Couleur: purple to dark blue
• Solubilité: H₂O: 2 mg/mL, clear
• Température de stockage: 2-8°C
• Chaîne SMILES: 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+
• Clé InChI: SVAGFBGXEWPNJC-LVEZLNDCSA-N

Description

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS08
• Mention d'avertissement: Warning
• Mentions de danger: H341,H361d
• Conseils de prudence: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Classification des risques: Muta. 2 - Repr. 2
• Code de la classe de stockage: 13 - Non Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable