ChemicalBook--->CAS DataBase List--->175414-77-4

175414-77-4

175414-77-4 Structure

175414-77-4 Structure
IdentificationBack Directory
[Name]

Voreloxin
[CAS]

175414-77-4
[Synonyms]

AG-7352
SNS-595
SPC-595
CS-1489
VOSAROXIN
Voreloxin
Voreloxin, >=98%
Voreloxin (SNS-595)
Voreloxin USP/EP/BP
SNS-595; VOSAROXIN; AG 7352
7-[(3S,4S)-3-methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid
1,4-Dihydro-7-[(3S,4S)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid
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
1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-7-[(3S,4S)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo -1-(2-thiazolyl)-
AG-7352, 1,4-dihydro-7-[(S,S)-3-Methoxy-4-MethylaMino-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic, (+)-1,4-dihydro-7-[(3S,4S)-3-Methoxy-4-(MethylaMino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid
[Molecular Formula]

C18H19N5O4S
[MDL Number]

MFCD13185156
[MOL File]

175414-77-4.mol
[Molecular Weight]

401.44
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

insoluble in H2O; insoluble in EtOH; insoluble in DMSO
[form ]

solid
Hazard InformationBack Directory
[Uses]

Voreloxin is a potent Topoisomerase II inhibitor with broad-spectrum anti-tumor activity.
[Biological Activity]

voreloxin, formerly known as sns-595 or ag-7352, is a novel naphthyridine analog, which is structurally related to the quinolone antibiotics, a chemical class not previously used for the treatmentof cancer.
[in vitro]

in vitro studies demonstrated voreloxin has broad anti-proliferative activity in 11 tumor cell lines, with ic50 values ranging from 0.04 to 0.97 μm. similar activity was observed in vitro in drug-resistant cell lines, including those that overexpress p-glycoprotein [2].
[in vivo]

after a single intravenous dose, voreloxin concentrations in tumor were correlated with induction of the apoptosis marker caspase-3. administration of voreloxin at 20 mg/kg weekly inhibited tumor growth (86%). voreloxin demonstrated strong dose-dependent tumor growth inhibition (63–88%) in 10 of 11 solid tumor xenograft models [2].
[References]

[1] 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;47(8):2097-109.
[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;64(1):53-65.
[3] advani rh, hurwitz hi, gordon ms, ebbinghaus sw, mendelson ds, wakelee ha, hoch u, silverman ja, havrilla na, berman cj, fox ja, allen rs, adelman dc. voreloxin, a first-in-class anticancer quinolone derivative, in relapsed/refractory solid tumors: a report on two dosing schedules. clin cancer res. 2010;16(7):2167-75.
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