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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
Structure of Banoxantrone

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

HIDE SMILES / InChI

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.

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:00:08 UTC 2023
Edited
by admin
on Fri Dec 15 16:00:08 UTC 2023
Record UNII
W5H7E45YT3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Banoxantrone
INN  
INN  
Official Name English
9,10-Anthracenedione, 1,4-bis[[2-(dimethyloxidoamino)ethyl]amino]-5,8-dihydroxy-
Common Name English
1,4-Bis[[2-(dimethyloxidoamino)ethyl]amino]-5,8-dihydroxy-9,10-anthracenedione
Systematic Name English
AQ4N
Code English
banoxantrone [INN]
Common Name English
AQ-4N
Code English
Classification Tree Code System Code
NCI_THESAURUS C253
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
Code System Code Type Description
CAS
136470-65-0
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
INN
8400
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
PUBCHEM
9955116
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
FDA UNII
W5H7E45YT3
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID90869860
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
SMS_ID
100000177189
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
NCI_THESAURUS
C79528
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
DRUG BANK
DB04975
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL117391
Created by admin on Fri Dec 15 16:00:08 UTC 2023 , Edited by admin on Fri Dec 15 16:00:08 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
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.
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
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.
Related Record Type Details
ACTIVE MOIETY