Banoxantrone
Grundinformationen
- CAS
136470-65-0- Standard-SMILES
C[N+](C)([O-])CCNc1ccc(NCC[N+](C)(C)[O-])c2c1C(=O)c1c(O)ccc(O)c1C2=O- InChIKey
YZBAXVICWUUHGG-UHFFFAOYSA-N- Summenformel
- C22H28N4O6
- Durchschnittliche Molmasse
- 444,5 g/mol
- Monoisotopische Masse
- 444,20088463
Überblick
Banoxantrone is a highly selective bioreductive drug that is activated in, and is preferentially toxic to, hypoxic cells in tumours. It has been shown to work synergistically with fractionated radiation to significantly delay growth of tumours compared to administration of either banoxantrone or radiation alone. Banoxantrone was also efficacious in tumour models when administered in combination with either cisplatin or chemoradiation.
Namen und Bezeichner
- Bevorzugter Name
- Banoxantrone
- IUPAC
- 2-[[4-[2-[dimethyl(oxido)azaniumyl]ethylamino]-5,8-dihydroxy-9,10-dioxoanthracen-1-yl]amino]-N,N-dimethylethanamine oxide
- Englischer Name
- Banoxantrone
- Summenformel
- C22H28N4O6
- Molmasse
- 444.48
Namen und Synonyme
Banoxantrone136470-65-0AQ-4NbanoxantronaW5H7E45YT3AQ 4NDTXSID908698601,4-bis-((2-(dimethylamino)ethyl)amino)-5,8-dihydroxyanthracene-9,10-dione9,10-Anthracenedione, 1,4-bis((2-(dimethylamino)ethyl)amino)-5,8-dihydroxy-, N,N'-dioxide9,10-Anthracenedione, 1,4-bis((2-(dimethyloxidoamino)ethyl)amino)-5,8-dihydroxy-banoxantronum9,10-Anthracenedione, 1,4-bis[[2-(dimethyloxidoamino)ethyl]amino]-5,8-dihydroxy-
Weitere Namen anzeigen
YZBAXVICWUUHGG-UHFFFAOYSA-NBanoxantrone dihydrochloride1,4-Bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide
RefChem:116442DTXCID308177641,4-bis-((2-(dimethylamino-N-oxide)ethyl)amino)-5,8-dihydroxyanthracene-9,10-dione2-((4-((2-(dimethyl-oxo-$l^(5)-azanyl)ethyl)amino)-5,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino)-N,N-dimethylethanamine oxideAQ4NBanoxantrone (AQ4N)2-[[4-[2-[dimethyl(oxido)azaniumyl]ethylamino]-5,8-dihydroxy-9,10-dioxoanthracen-1-yl]amino]-N,N-dimethylethanamine oxideBanoxantrone [INN:BAN]
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,3
- Polarare Oberfläche (TPSA)
- 135 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 32
- Formalladung
- 0
- Komplexität
- 644
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
AQ4N was rationally designed to have anti-tumor activity following bioreduction by tissue cytochrome P450 to AQ4, an active DNA topoisomerase II inhibitor. Preclinical studies demonstrated AQ4N selectively targets lymphoid tissues and hypoxic tumor tissues.
Mechanism of Action
Banoxantrone (formally known as AQ4N) is preferentially and irreversibly converted to AQ4, its cytotoxic form, in hypoxic tumour cells where it remains localised. When the surrounding oxygenated cells are killed by radiotherapy or chemotherapy bringing these AQ4-containing quiescent cells closer to the oxygen source, they become reoxygenated, attempt to resume replication and, in this state, are killed by AQ4 through potent DNA intercalation and topoisomerase II inhibition.
Biological Half-Life0.64 to 0.83 hours
Metabolism/MetabolitesAQ4N is selectively and irreversibly converted to AQ4, its cytotoxic form, in hypoxic tumor cells, which are its targeted site of action.
MeSH Pharmacological ClassificationSubstances that inhibit or prevent the proliferation of NEOPLASMS.
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