Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H28N4O6 |
| Molecular Weight | 444.4809 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[N+](C)([O-])CCNC1=C2C(=O)C3=C(O)C=CC(O)=C3C(=O)C2=C(NCC[N+](C)(C)[O-])C=C1
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 / 2 |
| 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
Cmax
| Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
| Value | Dose | Co-administered | 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 |
|
| Reduction of aromatic and heterocyclic aromatic N-hydroxylamines by human cytochrome P450 2S1. | 2013-06-17 |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:15:54 GMT 2025
by
admin
on
Mon Mar 31 18:15:54 GMT 2025
|
| Record UNII |
W5H7E45YT3
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C253
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
136470-65-0
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
8400
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
9955116
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
W5H7E45YT3
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
DTXSID90869860
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
100000177189
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
C79528
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
DB04975
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
PRIMARY | |||
|
CHEMBL117391
Created by
admin on Mon Mar 31 18:15:54 GMT 2025 , Edited by admin on Mon Mar 31 18:15:54 GMT 2025
|
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 |
|