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Merck

SML1854

Banoxantrone dihydrochloride

≥98% (HPLC)

Synonym(s):

1,4-Bis[[2-(dimethyloxidoamino)ethyl]amino]-5,8-dihydroxy-9,10-anthracenedione, AQ4N dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H28N4O6 · 2HCl
CAS Number:
252979-56-9
Molecular Weight:
517.40
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD19690955

Key Documents

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Product Name

Banoxantrone dihydrochloride, ≥98% (HPLC)

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

SMILES string

O=C1C2=C(C(NCC[N+](C)([O-])C)=CC=C2NCC[N+]([O-])(C)C)C(C3=C(O)C=CC(O)=C31)=O.[H]Cl.[H]Cl

InChI key

SBWCPHUXRZRTDP-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

blue

solubility

H2O: 3 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Banoxantrone dihydrochloride has been used as an organic ligand during a self-assembled metal-organic coordinated nanoparticle (Cu–OCNP/Lap) synthesis. It has also been used for the preparation of supramolecularly functionalized graphene oxide for hypoxia-activated chemotherapy of cancer.

Biochem/physiol Actions

Banoxantrone (AQ4N) is a hypoxia-activated prodrug of topoisomerase II inhibitor AQ4 (Bioreductive AQ4 precursor).
Banoxantrone dihydrochloride enhances the anti-tumor effect caused by radiation.
Hypoxia-activated prodrug of topoisomerase II inhibitor AQ4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000140352
017M4737V

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Alshad S Lalani et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 13(7), 2216-2225 (2007-04-04)
The antitumor activities and pharmacokinetics of the hypoxia-activated cytotoxin AQ4N and its metabolites were assessed in several preclinical models of pancreatic cancers. The cytotoxic effects of AQ4N prodrug and its bioreduced form, AQ4, were tested against multiple human tumor cell
Yuan-Fu Ding et al.
Biomaterials science, 9(10), 3804-3813 (2021-04-22)
Nano-graphene oxide (NGO) has attracted increasing attention as an advanced drug delivery system. However, the current surface functionalization and drug-loading of NGO either rely on π-π stacking that is limited to aromatic molecules, or covalent conjugation that requires tedious synthesis.
O P Friery et al.
British journal of cancer, 82(8), 1469-1473 (2000-04-26)
The ability of the bioreductive drugs AQ4N and tirapazamine to enhance the anti-tumour effect of cyclophosphamide was assessed in three murine tumour models. In male BDF mice implanted with the T50/80 mammary carcinoma, AQ4N (50-150 mg kg(-1)) in combination with
Olivier Trédan et al.
Cancer research, 69(3), 940-947 (2009-01-30)
Hypoxic tumor cells are likely to be resistant to conventional chemotherapy, in large part because many anticancer drugs are unable to penetrate into poorly oxygenated tumor tissue. Here, we used quantitative immunofluorescence to study the distribution of mitoxantrone and AQ4N
Qi Zhang et al.
Scientific reports, 12(1), 6294-6294 (2022-04-21)
Spike-mediated entry of SARS-CoV-2 into human airway epithelial cells is an attractive therapeutic target for COVID-19. In addition to protein receptors, the SARS-CoV-2 spike (S) protein also interacts with heparan sulfate, a negatively charged glycosaminoglycan (GAG) attached to certain membrane
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