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Merck
CN

SML1823

Vosaroxin hydrochloride

≥98% (HPLC)

Synonym(s):

1,4-Dihydro-7-[(3S,4S)-3-methoxy-4-(methylamino)-1-pyrrolidinyl]-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid hydrochloride, SNS-595 hydrochloride, Voreloxin hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H19N5O4S · HCl
CAS Number:
175519-16-1
Molecular Weight:
437.90
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD13185156

Key Documents

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Product Name

Vosaroxin hydrochloride, ≥98% (HPLC)

InChI

1S/C18H19N5O4S.ClH/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);1H/t12-,13-;/m0./s1

SMILES string

O=C(C(C(O)=O)=C1)C2=C(N=C(C=C2)N3C[C@@H]([C@H](C3)NC)OC)N1C4=NC=CS4

InChI key

JJZCCQHWCOXGCL-QNTKWALQSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +42 to +52°, c = 1 in 0.1 M NaOH

color

white to beige

solubility

H2O: 1 mg/mL, clear (warmed)

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Vosaroxin is an anti-cancer quinolone derivative that acts as a DNA intercalator and a topoisomerase II inhibitor, causing p53 independent tumor cell apoptosis. Vosaroxin stabilizes cleavage complexes formed by topoisomerase IIα and IIβ, which results in an accumulation of DNA double-strand breaks. Vosaroxin showed antineoplastic activity in multiple solid tumor and hematologic cancer cell lines and has been in clinical trials for AML.
Vosaroxin is an anti-cancer quinolone derivative that acts as a DNA intercalator and a topoisomerase II inhibitor.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
126M4703V

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Nicholas J Short et al.
Expert review of hematology, 9(6), 529-534 (2016-05-10)
The outcomes of patients with relapsed or refractory acute myeloid leukemia (AML) are dismal, and effective treatment options in this patient population are therefore desperately needed. Vosaroxin is a first-in-class anticancer quinolone derivative that has shown promising activity in patients
Gene C Jamieson et al.
Drugs, 76(13), 1245-1255 (2016-08-04)
Vosaroxin is a first-in-class anticancer quinolone derivative that targets topoisomerase II and induces site-selective double-strand breaks in DNA, leading to tumor cell apoptosis. Vosaroxin has chemical and pharmacologic characteristics distinct from other topoisomerase II inhibitors due to its quinolone scaffold.
Christopher B Benton et al.
Future oncology (London, England), 13(2), 125-133 (2016-09-13)
Vosaroxin is a quinolone compound that intercalates DNA and induces TP53-independent apoptosis, demonstrating activity against acute myeloid leukemia (AML) in Phase I-III trials. Here, we examine vosaroxin's mechanism of action and pharmacology, and we review its use in AML to

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