Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H28N4O6 |
Molecular Weight | 444.4809 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=YZBAXVICWUUHGG-UHFFFAOYSA-N
InChI=1S/C22H28N4O6/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
Molecular Formula | C22H28N4O6 |
Molecular Weight | 444.4809 |
Charge | 0 |
Count |
|
Stereochemistry | MIXED |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18681417 |
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Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9054961 |
PubMed
Title | Date | PubMed |
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A cytochrome P450 2B6 meditated gene therapy strategy to enhance the effects of radiation or cyclophosphamide when combined with the bioreductive drug AQ4N. | 2005 Jul |
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Reduction of aromatic and heterocyclic aromatic N-hydroxylamines by human cytochrome P450 2S1. | 2013 Jun 17 |
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Versatile hyaluronic acid modified AQ4N-Cu(II)-gossypol infinite coordination polymer nanoparticles: Multiple tumor targeting, highly efficient synergistic chemotherapy, and real-time self-monitoring. | 2018 Feb |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:00:08 GMT 2023
by
admin
on
Fri Dec 15 16:00:08 GMT 2023
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Record UNII |
W5H7E45YT3
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C253
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100000177189
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C79528
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DB04975
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CHEMBL117391
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
CYP2S1 is expressed in the epithelial cells of trachea, small intestine, stomach, spleen, lung, and colon, but is found at much lower levels in liver, kidney, and most other tissues. The protein is apparently overexpressed in psoriatic skin (Karlgren et al., 2005) and hypoxic tumors.
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
Reduction of AQ4N to the mono N-oxide intermediate AQ4M [ 1-{[2-(dimethylamino-N-oxide)ethyl]amino}-4-{[2-(dimethylamino) ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione] and finally to AQ4 provides a mechanism for selectively generating the active topoisomerase inhibitor within hypoxic cancer cells.
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ACTIVE MOIETY |
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