BANOXANTRONE DIHYDROCHLORIDE

Investigational

Details

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

SHOW SMILES / InChI

Structure of BANOXANTRONE DIHYDROCHLORIDE

Structure Search

SMILES

Cl.Cl.C[N+](C)([O-])CCNC1=C2C(=O)C3=C(C(O)=CC=C3O)C(=O)C2=C(NCC[N+](C)(C)[O-])C=C1

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	C22H28N4O6
Molecular Weight	444.4809
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17340571 | https://www.biospace.com/article/releases/novacea-inc-to-discontinue-cancer-drug-trial-/ | https://www.ncbi.nlm.nih.gov/pubmed/26782976

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
Nitric oxide synthase, inducible 55 Target ID: CHEMBL4481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18681417	Substrate 661
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9054961	Inhibitor 8504

C_max

Value	Dose	Analyte	Population
1720 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	12 mg/m² single, intravenous dose: 12 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4382 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	24 mg/m² single, intravenous dose: 24 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
7374 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	48 mg/m² single, intravenous dose: 48 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
13457 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	96 mg/m² single, intravenous dose: 96 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
28440 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	192 mg/m² single, intravenous dose: 192 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
50660 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	384 mg/m² single, intravenous dose: 384 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
98415 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	768 mg/m² single, intravenous dose: 768 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
144556 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	1200 mg/m² single, intravenous dose: 1200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
7092 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	12 mg/m² single, intravenous dose: 12 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6609 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	24 mg/m² single, intravenous dose: 24 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
12320 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	48 mg/m² single, intravenous dose: 48 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
44376 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	96 mg/m² single, intravenous dose: 96 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
65115 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	192 mg/m² single, intravenous dose: 192 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
153801 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	384 mg/m² single, intravenous dose: 384 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
242282 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	768 mg/m² single, intravenous dose: 768 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
485034 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	1200 mg/m² single, intravenous dose: 1200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	12 mg/m² single, intravenous dose: 12 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	24 mg/m² single, intravenous dose: 24 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	48 mg/m² single, intravenous dose: 48 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	96 mg/m² single, intravenous dose: 96 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	192 mg/m² single, intravenous dose: 192 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	384 mg/m² single, intravenous dose: 384 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	768 mg/m² single, intravenous dose: 768 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18981010/	1200 mg/m² single, intravenous dose: 1200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	BANOXANTRONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
Versatile hyaluronic acid modified AQ4N-Cu(II)-gossypol infinite coordination polymer nanoparticles: Multiple tumor targeting, highly efficient synergistic chemotherapy, and real-time self-monitoring.	2018-02	29128847
Reduction of aromatic and heterocyclic aromatic N-hydroxylamines by human cytochrome P450 2S1.	2013-06-17	23682735
A cytochrome P450 2B6 meditated gene therapy strategy to enhance the effects of radiation or cyclophosphamide when combined with the bioreductive drug AQ4N.	2005-07	15712360

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:02:20 GMT 2025` Edited by `admin` on `Mon Mar 31 18:02:20 GMT 2025`
Record UNII	658876KMFP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,4-BIS((2-(DIMETHYLNITRORYL)ETHYL)AMINO)-5,8-DIHYDROXYANTHRA-9,10-QUINONE DIHYDROCHLORIDE

Preferred Name

English

BANOXANTRONE DIHYDROCHLORIDE

Common Name

English

1,4-BIS((2-(DIMETHYLAMINO)ETHYL)AMINO)-5,8-DIHYDROXYANTHRACENE-9,10-DIONE BIS-N-OXIDE HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

MESH

C094428