Voreloxin | SNS-595 | Vosaroxin | CAS#175414-77-4 | Topoisomerase II Inhibitor

MedKoo Cat#: 202650 | Name: Voreloxin

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Description:

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

Voreloxin, also known as SNS-595 or Vosaroxin, is a s mall molecule and a naphthyridine analogue with antineoplastic activity. Vosaroxin intercalates into DNA in a site-specific manner and blocks the re-ligation process carried out by topoisomerase II during DNA replication. As a result, inhibition of DNA replication, RNA and protein synthesis occurs, followed by cell cycle arrest at G2 phase and induced p53-independent apoptosis. This agent shows a favorable toxicity profile in several aspects: it does not generate reactive oxygen species, as do anthracyclines, reducing the risk of cardiotoxicity.

Chemical Structure

Voreloxin

CAS#175414-77-4

Theoretical Analysis

MedKoo Cat#: 202650

Name: Voreloxin

CAS#: 175414-77-4

Chemical Formula: C18H19N5O4S

Exact Mass: 401.1158

Molecular Weight: 401.44

Elemental Analysis: C, 53.85; H, 4.77; N, 17.45; O, 15.94; S, 7.99

Price and Availability

Size	Price	Availability
5mg	USD 450.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 950.00	2 Weeks
50mg	USD 1,450.00	2 Weeks
100mg	USD 2,250.00	2 Weeks

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Related CAS #

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Synonym

SNS 595; SNS595; SNS-595; SPC595; SPC-595; SPC 595; AG7352; AG 7352; AG-7352; Voreloxin; Vosaroxin.

IUPAC/Chemical Name

7-((3S,4S)-3-methoxy-4-(methylamino)pyrrolidin-1-yl)-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid.

InChi Key

XZAFZXJXZHRNAQ-STQMWFEESA-N

InChi Code

InChI=1S/C18H19N5O4S/c1-19-12-8-22(9-13(12)27-2)14-4-3-10-15(24)11(17(25)26)7-23(16(10)21-14)18-20-5-6-28-18/h3-7,12-13,19H,8-9H2,1-2H3,(H,25,26)/t12-,13-/m0/s1

SMILES Code

O=C(C1=CN(C2=NC=CS2)C3=C(C=CC(N4C[C@H](OC)[C@@H](NC)C4)=N3)C1=O)O

Appearance

White to off-white 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

>2 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).

HS Tariff Code

2934.99.9001

More Info

SNS-595 is a novel naphthyridine analog, structurally related to quinolones, a class of compounds which has not been used previously in the treatment of cancer. Sunesis researchers conducted in vitro and cell-based studies elucidating SNS-595's mechanism of action. SNS-595 selectively intercalates DNA and poisons topoisomerase II, resulting in replication-dependent DNA damage, irreversible G2 arrest and rapid apoptosis. SNS-595's targeted DNA-topoisomerase II interactions may contribute to the broad therapeutic window observed in patients treated with SNS-595. SNS-595 avoids common drug resistance pathways and may have advantages over other topoisomerase poisons

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 401.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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PMID: 35570520. 4: Anza M, Endale M, Cardona L, Cortes D, Eswaramoorthy R, Zueco J, Rico H, Trelis M, Abarca B. Antimicrobial Activity, in silico Molecular Docking, ADMET and DFT Analysis of Secondary Metabolites from Roots of Three Ethiopian Medicinal Plants. Adv Appl Bioinform Chem. 2021 Aug 20;14:117-132. doi: 10.2147/AABC.S323657. PMID: 34447254; PMCID: PMC8384431. 5: Mithula S, Nandikolla A, Murugesan S, Kondapalli VG. 1,8-naphthyridine derivatives: an updated review on recent advancements of their myriad biological activities. Future Med Chem. 2021 Sep;13(18):1591-1618. doi: 10.4155/fmc-2021-0086. Epub 2021 Jul 14. PMID: 34256591. 6: Al-Nuaimi A, Al-Hiari Y, Kasabri V, Haddadin R, Mamdooh N, Alalawi S, Khaleel S. A Novel Class of Functionalized Synthetic Fluoroquinolones with Dual Antiproliferative - Antimicrobial Capacities. Asian Pac J Cancer Prev. 2021 Apr 1;22(4):1075-1086. doi: 10.31557/APJCP.2021.22.4.1075. PMID: 33906299; PMCID: PMC8325119. 7: Ojha M, Yadav D, Kumar A, Dasgupta S, Yadav R. 1,8-Naphthyridine Derivatives: A Privileged Scaffold for Versatile Biological Activities. Mini Rev Med Chem. 2021;21(5):586-601. doi: 10.2174/1389557520666201009162804. PMID: 33038911. 8: Yang M, Liu H, Zhang Y, Wang X, Xu Z. Moxifloxacin-isatin Hybrids Tethered by 1,2,3-triazole and their Anticancer Activities. Curr Top Med Chem. 2020;20(16):1461-1467. doi: 10.2174/1568026620666200128144825. PMID: 31994464. 9: Jasek-Gajda E, Jurkowska H, Jasińska M, Litwin JA, Lis GJ. Combination of ERK2 inhibitor VX-11e and voreloxin synergistically enhances anti-proliferative and pro-apoptotic effects in leukemia cells. Apoptosis. 2019 Dec;24(11-12):849-861. doi: 10.1007/s10495-019-01564-6. PMID: 31482470; PMCID: PMC6823322. 10: Blower TR, Bandak A, Lee ASY, Austin CA, Nitiss JL, Berger JM. A complex suite of loci and elements in eukaryotic type II topoisomerases determine selective sensitivity to distinct poisoning agents. Nucleic Acids Res. 2019 Sep 5;47(15):8163-8179. doi: 10.1093/nar/gkz579. PMID: 31287876; PMCID: PMC6735899. 11: Economides MP, McCue D, Borthakur G, Pemmaraju N. Topoisomerase II inhibitors in AML: past, present, and future. Expert Opin Pharmacother. 2019 Sep;20(13):1637-1644. doi: 10.1080/14656566.2019.1621292. Epub 2019 May 28. PMID: 31136213. 12: Liu F, Knight T, Su Y, Edwards H, Wang G, Wang Y, Taub JW, Lin H, Sun L, Ge Y. Venetoclax Synergistically Enhances the Anti-leukemic Activity of Vosaroxin Against Acute Myeloid Leukemia Cells Ex Vivo. Target Oncol. 2019 Jun;14(3):351-364. doi: 10.1007/s11523-019-00638-4. PMID: 31115744. 13: Jasek-Gajda E, Gajda M, Jasińska M, Litwin JA, Lis GJ. TAK-733, a Selective MEK Inhibitor, Enhances Voreloxin-induced Apoptosis in Myeloid Leukemia Cells. Anticancer Res. 2018 Nov;38(11):6147-6156. doi: 10.21873/anticanres.12967. PMID: 30396931. 14: Huang J, Gui C, Zhang L, Che F, Wang C. A Bayesian Network Meta-Analysis Comparing the Efficacies of Eleven Novel Therapies with the Common Salvage Regimen for Relapsed or Refractory Acute Myeloid Leukemia. Cell Physiol Biochem. 2018;49(4):1589-1599. doi: 10.1159/000493494. Epub 2018 Sep 17. PMID: 30223267. 15: Zhao XL, Yu CZ. Vosaroxin induces mitochondrial dysfunction and apoptosis in cervical cancer HeLa cells: Involvement of AMPK/Sirt3/HIF-1 pathway. Chem Biol Interact. 2018 Jun 25;290:57-63. doi: 10.1016/j.cbi.2018.05.011. Epub 2018 May 22. PMID: 29800573. 16: Ravandi F, Ritchie EK, Sayar H, Lancet JE, Craig MD, Vey N, Strickland SA, Schiller GJ, Jabbour E, Pigneux A, Horst HA, Récher C, Klimek VM, Cortes JE, Carella AM, Egyed M, Krug U, Fox JA, Craig AR, Ward R, Smith JA, Acton G, Kantarjian HM, Stuart RK. Phase 3 results for vosaroxin/cytarabine in the subset of patients ≥60 years old with refractory/early relapsed acute myeloid leukemia. Haematologica. 2018 Nov;103(11):e514-e518. doi: 10.3324/haematol.2018.191361. Epub 2018 May 24. PMID: 29794146; PMCID: PMC6278965. 17: Sayar H, Bashardoust P. Therapies for acute myeloid leukemia: vosaroxin. Onco Targets Ther. 2017 Aug 7;10:3957-3963. doi: 10.2147/OTT.S121477. PMID: 28860803; PMCID: PMC5558588. 18: Daver N, Kantarjian H, Garcia-Manero G, Jabbour E, Borthakur G, Brandt M, Pierce S, Vaughan K, Ning J, Nogueras González GM, Patel K, Jorgensen J, Pemmaraju N, Kadia T, Konopleva M, Andreeff M, DiNardo C, Cortes J, Ward R, Craig A, Ravandi F. Vosaroxin in combination with decitabine in newly diagnosed older patients with acute myeloid leukemia or high-risk myelodysplastic syndrome. Haematologica. 2017 Oct;102(10):1709-1717. doi: 10.3324/haematol.2017.168732. Epub 2017 Jul 20. PMID: 28729302; PMCID: PMC5622855. 19: Sedov V, Stuart RK. Vosaroxin in relapsed/refractory acute myeloid leukemia: efficacy and safety in the context of the current treatment landscape. Ther Adv Hematol. 2017 Jun;8(6):185-195. doi: 10.1177/2040620717703012. Epub 2017 Apr 21. PMID: 28567238; PMCID: PMC5424861. 20: Paubelle E, Zylbersztejn F, Thomas X. The preclinical discovery of vosaroxin for the treatment of acute myeloid leukemia. Expert Opin Drug Discov. 2017 Jul;12(7):747-753. doi: 10.1080/17460441.2017.1331215. Epub 2017 May 22. PMID: 28504025.