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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • CN[C@H]1CN(C[C@@H]1OC)C2=NC3=C(C=C2)C(=O)C(=CN3C4=NC=CS4)C(=O)O
Properties
C18H19N5O4S
Molar mass 401.44 g·mol−1
Density 1.5±0.1 g/cm3
Pharmacology
L01XX53 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1]

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.[2]

References

  1. ^ "Vosaroxin". Selleck Chemicals.
  2. ^ "Vosaroxin (Formerly Voreloxin)". Sunesis.


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