Banoxantrone (AQ4N)

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200430

CAS#: 136470-65-0

Description: Banoxantrone is a bioreductive, alkylaminoanthraquinone prodrug with antineoplastic activity. Under hypoxic conditions, often seen in solid tumors, banoxantrone (AQ4N) is converted and activated by cytochrome P450 enzymes, which are upregulated in certain tumors, to the cytotoxic DNA-binding agent AQ4. Banoxantrone intercalates into and crosslinks DNA, and inhibits topoisomerase II. This results in an inhibition of DNA replication and repair in tumor cells. Combined with conventional therapeutic agents, both oxygenic and hypoxic regions of tumors can be targeted.


Price and Availability

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Banoxantrone (AQ4N), is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200430
Name: Banoxantrone (AQ4N)
CAS#: 136470-65-0
Chemical Formula: C22H28N4O6
Exact Mass: 444.20088
Molecular Weight: 444.48
Elemental Analysis: C, 59.45; H, 6.35; N, 12.60; O, 21.60


Synonym: AQ-4N; AZD-1689; AQ4N; AZD1689; AQ 4N; AZD 1689

IUPAC/Chemical Name: 2,2'-(5,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(azanediyl)bis(N,N-dimethylethanamine oxide)

InChi Key: YZBAXVICWUUHGG-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C(C1=C2C(O)=CC=C1O)C3=C(NCC[N+](C)([O-])C)C=CC(NCC[N+](C)([O-])C)=C3C2=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

 1: Gieling RG, Fitzmaurice RJ, Telfer BA, Babur M, Williams KJ. Dissemination via the lymphatic or angiogenic route impacts the pathology, microenvironment and hypoxia-related drug response of lung metastases. Clin Exp Metastasis. 2015 Jun 26. [Epub ahead of print] PubMed PMID: 26112891.

2: Guise CP, Mowday AM, Ashoorzadeh A, Yuan R, Lin WH, Wu DH, Smaill JB, Patterson AV, Ding K. Bioreductive prodrugs as cancer therapeutics: targeting tumor hypoxia. Chin J Cancer. 2014 Feb;33(2):80-6. doi: 10.5732/cjc.012.10285. Epub 2013 Jul 12. Review. PubMed PMID: 23845143; PubMed Central PMCID: PMC3935009.

3: Manley E Jr, Waxman DJ. Impact of tumor blood flow modulation on tumor sensitivity to the bioreductive drug banoxantrone. J Pharmacol Exp Ther. 2013 Feb;344(2):368-77. doi: 10.1124/jpet.112.200089. Epub 2012 Nov 28. PubMed PMID: 23192656; PubMed Central PMCID: PMC3558827.

4: Ming L, Byrne NM, Camac SN, Mitchell CA, Ward C, Waugh DJ, McKeown SR, Worthington J. Androgen deprivation results in time-dependent hypoxia in LNCaP prostate tumours: informed scheduling of the bioreductive drug AQ4N improves treatment response. Int J Cancer. 2013 Mar 15;132(6):1323-32. doi: 10.1002/ijc.27796. Epub 2012 Nov 23. PubMed PMID: 22915157.

5: Bebenek IG, Solaimani P, Bui P, Hankinson O. CYP2S1 is negatively regulated by corticosteroids in human cell lines. Toxicol Lett. 2012 Feb 25;209(1):30-4. doi: 10.1016/j.toxlet.2011.11.020. Epub 2011 Nov 30. PubMed PMID: 22155357.

6: Xiao Y, Shinkyo R, Guengerich FP. Cytochrome P450 2S1 is reduced by NADPH-cytochrome P450 reductase. Drug Metab Dispos. 2011 Jun;39(6):944-6. doi: 10.1124/dmd.111.039321. Epub 2011 Mar 23. PubMed PMID: 21430234; PubMed Central PMCID: PMC3100906.

7: Nishida CR, Lee M, de Montellano PR. Efficient hypoxic activation of the anticancer agent AQ4N by CYP2S1 and CYP2W1. Mol Pharmacol. 2010 Sep;78(3):497-502. doi: 10.1124/mol.110.065045. Epub 2010 Jun 21. PubMed PMID: 20566689; PubMed Central PMCID: PMC2939484.

8: Williams KJ, Albertella MR, Fitzpatrick B, Loadman PM, Shnyder SD, Chinje EC, Telfer BA, Dunk CR, Harris PA, Stratford IJ. In vivo activation of the hypoxia-targeted cytotoxin AQ4N in human tumor xenografts. Mol Cancer Ther. 2009 Dec;8(12):3266-75. doi: 10.1158/1535-7163.MCT-09-0396. Epub . PubMed PMID: 19996276.

9: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Apr;31(3):183-226. PubMed PMID: 19536362.

10: Mehibel M, Singh S, Chinje EC, Cowen RL, Stratford IJ. Effects of cytokine-induced macrophages on the response of tumor cells to banoxantrone (AQ4N). Mol Cancer Ther. 2009 May;8(5):1261-9. doi: 10.1158/1535-7163.MCT-08-0927. Epub 2009 May 12. PubMed PMID: 19435866.