WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202650
Description: 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.
MedKoo Cat#: 202650
Chemical Formula: C18H19N5O4S
Exact Mass: 401.11577
Molecular Weight: 401.44
Elemental Analysis: C, 53.85; H, 4.77; N, 17.45; O, 15.94; S, 7.99
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
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
1: Evanchik MJ, Allen D, Yoburn JC, Silverman JA, Hoch U. Metabolism of (+)-1,4-dihydro-7-(trans-3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiaz olyl)-1,8-naphthyridine-3-carboxylic acid (voreloxin; formerly SNS-595), a novel replication-dependent DNA-damaging agent. Drug Metab Dispos. 2009 Mar;37(3):594-601. Epub 2008 Dec 12. PubMed PMID: 19074528.
2: Hoch U, Lynch J, Sato Y, Kashimoto S, Kajikawa F, Furutani Y, Silverman JA. Voreloxin, formerly SNS-595, has potent activity against a broad panel of cancer cell lines and in vivo tumor models. Cancer Chemother Pharmacol. 2009 Jun;64(1):53-65. Epub 2008 Oct 19. PubMed PMID: 18931998.
3: Mills DA, Fekrazad HM, Verschraegen CF. SNS-595, a naphthyridine cell cycle inhibitor and stimulator of apoptosis for the treatment of cancers. Curr Opin Investig Drugs. 2008 Jun;9(6):647-57. Review. PubMed PMID: 18516764.
4: Srivastava SK, Jha A, Agarwal SK, Mukherjee R, Burman AC. Synthesis and structure-activity relationships of potent antitumor active quinoline and naphthyridine derivatives. Anticancer Agents Med Chem. 2007 Nov;7(6):685-709. Review. PubMed PMID: 18045063.
5: Tsuzuki Y, Tomita K, Shibamori K, Sato Y, Kashimoto S, Chiba K. Synthesis and structure-activity relationships of novel 7-substituted 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids as antitumor agents. Part 2. J Med Chem. 2004 Apr 8;47(8):2097-109. PubMed PMID: 15056007.