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Details

Stereochemistry ACHIRAL
Molecular Formula C22H28N4O6.2ClH
Molecular Weight 517.403
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BANOXANTRONE DIHYDROCHLORIDE

SMILES

Cl.Cl.C[N+](C)([O-])CCNC1=CC=C(NCC[N+](C)(C)[O-])C2=C1C(=O)C3=C(O)C=CC(O)=C3C2=O

InChI

InChIKey=SBWCPHUXRZRTDP-UHFFFAOYSA-N
InChI=1S/C22H28N4O6.2ClH/c1-25(2,31)11-9-23-13-5-6-14(24-10-12-26(3,4)32)18-17(13)21(29)19-15(27)7-8-16(28)20(19)22(18)30;;/h5-8,23-24,27-28H,9-12H2,1-4H3;2*1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H28N4O6
Molecular Weight 444.4809
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Banoxantrone (formally known as AQ4N), a bioreductive drug that is irreversibly converted to AQ4, a stable DNA affinic cytotoxic compound. Banoxantrone is activated by haem-containing reductases such as inducible nitric oxide synthase (iNOS). In hypoxic cells, AQ4N is reduced to the topoisomerase II inhibitor AQ4. By inhibition of topoisomerase II within these hypoxic areas, AQ4N has been shown to sensitize tumors to existing chemo- and radiotherapy treatments. Novacea, the company which was responsible for clinical trials for banoxantrone had decided to scale back on its clinical development, including discontinuing the clinical trial in acute lymphoblastic leukemia and delaying the planned clinical trial in B-cell lymphoma. The company decided to continue enrollment in an ongoing Phase 1b/2a clinical trial in patients with glioblastoma multiforme. However, further information about these clinical trials are not available. Some recent experiments have shown that targeting hypoxic tumors with high levels of iNOS with a combination of AQ4N and radiotherapy could be a useful clinical therapeutic strategy.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Substance Class Chemical
Record UNII
658876KMFP
Record Status Validated (UNII)
Record Version