Pixantrone

Pixantrone
Names
Preferred IUPAC name
6,9-Bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • InChI=1S/C17H19N5O2/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/h1-3,6,9,21-22H,4-5,7-8,18-19H2 checkY
    Key: PEZPMAYDXJQYRV-UHFFFAOYSA-N checkY
  • InChI=1/C17H19N5O2/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/h1-3,6,9,21-22H,4-5,7-8,18-19H2
    Key: PEZPMAYDXJQYRV-UHFFFAOYAV
  • O=C2c3c(C(=O)c1c(ccc(NCCN)c12)NCCN)cncc3
Properties
C17H19N5O2
Molar mass 325.365 g/mol
Appearance Blue solid
Pharmacology
L01DB11 (WHO)
Intravenous
Pharmacokinetics:
9.5–17.5 hours
Fecal (main route of excretion) and renal (4–9%)
Legal status
  • UK: POM (Prescription only) / Discontinued[1]
  • EU: Rx-only / Expired[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Pixantrone (rINN; trade name Pixuvri) is an experimental antineoplastic (anti-cancer) drug, an analogue of mitoxantrone with fewer toxic effects on cardiac tissue.[3] It acts as a topoisomerase II poison and intercalating agent.[4][5] The code name BBR 2778 refers to pixantrone dimaleate, the actual substance commonly used in clinical trials.[6]

  1. ^ "Pixuvri 29 mg powder for concentrate for solution for infusion". (emc). 23 November 2021. Retrieved 12 July 2024.
  2. ^ Cite error: The named reference Pixuvri EPAR was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference pmid17285358 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference pmid7623772 was invoked but never defined (see the help page).
  5. ^ Evison BJ, Mansour OC, Menta E, Phillips DR, Cutts SM (2007). "Pixantrone can be activated by formaldehyde to generate a potent DNA adduct forming agent". Nucleic Acids Res. 35 (11): 3581–9. doi:10.1093/nar/gkm285. PMC 1920253. PMID 17483512.
  6. ^ Krapcho AP, Petry ME, Getahun Z, Landi JJ Jr, Stallman J, Polsenberg JF, et al. (1994). "6,9-Bis[(aminoalkyl)amino]benzo[g]isoquinoline-5,10-diones. A novel class of chromophore-modified antitumor anthracene-9,10-diones: synthesis and antitumor evaluations". J Med Chem. 37 (6): 828–37. doi:10.1021/jm00032a018. PMID 8145234.