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Details

Stereochemistry ACHIRAL
Molecular Formula C22H28N4O4
Molecular Weight 412.4821
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AQ4

SMILES

CN(C)CCNC1=C2C(=O)C3=C(C(O)=CC=C3O)C(=O)C2=C(NCCN(C)C)C=C1

InChI

InChIKey=DBAMBJQJKDHEQX-UHFFFAOYSA-N
InChI=1S/C22H28N4O4/c1-25(2)11-9-23-13-5-6-14(24-10-12-26(3)4)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

HIDE SMILES / InChI

Molecular Formula C22H28N4O4
Molecular Weight 412.4821
Charge 0
Count
Stereochemistry ACHIRAL
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
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
Reduction of aromatic and heterocyclic aromatic N-hydroxylamines by human cytochrome P450 2S1.
2013 Jun 17
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 Fri Dec 15 17:15:26 GMT 2023
Edited
by admin
on Fri Dec 15 17:15:26 GMT 2023
Record UNII
QXB9LEJ2B2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AQ4
Common Name English
BIS((2-(DIMETHYLAMINO)ETHYL)AMINO)-5,8-DIHYDROXYANTHRAQUINONE, 1,4-
Systematic Name English
Code System Code Type Description
CAS
70476-63-0
Created by admin on Fri Dec 15 17:15:26 GMT 2023 , Edited by admin on Fri Dec 15 17:15:26 GMT 2023
PRIMARY
FDA UNII
QXB9LEJ2B2
Created by admin on Fri Dec 15 17:15:26 GMT 2023 , Edited by admin on Fri Dec 15 17:15:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID00220741
Created by admin on Fri Dec 15 17:15:26 GMT 2023 , Edited by admin on Fri Dec 15 17:15:26 GMT 2023
PRIMARY
PUBCHEM
135468
Created by admin on Fri Dec 15 17:15:26 GMT 2023 , Edited by admin on Fri Dec 15 17:15:26 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
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.