WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202650
CAS#: 175414-77-4
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
Name: Voreloxin
CAS#: 175414-77-4
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
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
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 |
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.
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
