Chemistry:Vosaroxin

Vosaroxin

Names
Preferred IUPAC name 7-[(3S,4S)-3-Methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Other names Voreloxin
Identifiers
CAS Number	175414-77-4 Y
3D model (JSmol)	Interactive image
ChemSpider	8128494
PubChem CID	9952884
UNII	K6A90IIZ19 Y
InChI 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 Key: XZAFZXJXZHRNAQ-STQMWFEESA-N InChI=1/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 Key: XZAFZXJXZHRNAQ-STQMWFEEBT
SMILES CN[C@H]1CN(C[C@@H]1OC)C2=NC3=C(C=C2)C(=O)C(=CN3C4=NC=CS4)C(=O)O
Properties
Chemical formula	C18H19N5O4S
Molar mass	401.44 g·mol−1
Density	1.5±0.1 g/cm3
Pharmacology
1=ATC code }}	L01XX53 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Vosaroxin (AG-7352, SPC-595, SNS 595, voreloxin) is a topoisomerase II inhibitor causing site-selective DNA damage. It is under phase III clinical trial investigation for acute myelogenous leukemia (AML) and ovarian cancer sponsored by Sunesis.

Mechanism of action

Vosaroxin is a naphthyridine analog of the anticancer quinolone derivatives (AQDs), a class of compounds that has not been used previously for the treatment of cancer. Topoisomerase II enzymes are essential for the survival of eukaryotic cells. Vosaroxin hinders the reunion of topoisomerase II-induced double-strand breaks at selective sites in DNA, resulting in G2 arrest and cell death by apoptosis.