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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H19N5O4S
Molecular Weight 401.44
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VOSAROXIN

SMILES

CN[C@H]1CN(C[C@@H]1OC)C2=CC=C3C(=O)C(=CN(C4=NC=CS4)C3=N2)C(O)=O

InChI

InChIKey=XZAFZXJXZHRNAQ-STQMWFEESA-N
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

HIDE SMILES / InChI

Molecular Formula C18H19N5O4S
Molecular Weight 401.44
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18516764 | https://www.ncbi.nlm.nih.gov/pubmed/21252718 | https://www.ncbi.nlm.nih.gov/pubmed/21134979

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 Pharmaceuticals Inc.

CNS Activity

Curator's Comment: Radiolabeling experiments in mice indicate that vosaroxin crosses the blood–brain barrier

Originator

Curator's Comment: In 2003 Sunesis licensed worldwide development and commercialization rights to vosaroxin from Sumitomo Dainippon Pharma Co., Ltd. (http://www.sunesis.com/ongoing-partnerships.php)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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.
2004 Apr 8
SNS-595, a naphthyridine cell cycle inhibitor and stimulator of apoptosis for the treatment of cancers.
2008 Jun
Voreloxin, a first-in-class anticancer quinolone derivative, in relapsed/refractory solid tumors: a report on two dosing schedules.
2010 Apr 1
Voreloxin, a first-in-class anticancer quinolone derivative, acts synergistically with cytarabine in vitro and induces bone marrow aplasia in vivo.
2010 Oct
A phase Ib study of vosaroxin, an anticancer quinolone derivative, in patients with relapsed or refractory acute leukemia.
2011 Dec
Vosaroxin : a novel antineoplastic quinolone.
2012 Aug
Molecular and Pharmacologic Properties of the Anticancer Quinolone Derivative Vosaroxin: A New Therapeutic Agent for Acute Myeloid Leukemia.
2016 Sep
Patents

Sample Use Guides

50 mg/m2 on Days 1 and 4 of 28 day cycle (Dose level 1), 72 mg/m2 on Days 1 and 4 of 28 day cycle (Dose level 2), 50 mg/m2 on Days 1, 4, 8 and 11 of 28 day cycle (Dose level 3), 72 mg/m2 on Days 1, 4, 8 and 11 of 28 day cycle (Dose level 4)
Route of Administration: Intravenous
Inhibition of proliferation by vosaroxin was studied in three cancer cell lines: HL-60 (acute promyelocytic leukemia), MV4-11 (AML), and CCRF-CEM (Acute lymphoblastic leukemia) using initial concentrations of voreloxin: CCRF-CEM, 1.5 uM; MV4-11, 1.0 uM; HL-60, 9 uM. Cells were seeded in opaque, clear bottom 96-well plates at 1 × 10^5/well in growth media. Voreloxin was serially diluted in growth media and added to the appropriate wells. CellTiter-Glo Luminescent Cell Viability Assay (Promega, Madison, WI) was performed as per manufacturer’s protocol, and the median of three replicate wells was used for IC50 curve generation. The average IC50 for voreloxin in the AML cell lines MV4-11 and HL-60 was 95 ± 8 nM and 884 ± 114 nM, respectively. CCRF-CEM cell line was also sensitive to voreloxin with an average IC50 of 166 ± 0.4 nM.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:21:52 UTC 2023
Edited
by admin
on Wed Jul 05 23:21:52 UTC 2023
Record UNII
K6A90IIZ19
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOSAROXIN
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
VOSAROXIN [MART.]
Common Name English
SNS-595
Code English
Vosaroxin [WHO-DD]
Common Name English
(+)-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
Systematic Name English
VORELOXIN
Common Name English
VOSAROXIN [USAN]
Common Name English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1,4-DIHYDRO-7-((3S,4S)-3-METHOXY-4-(METHYLAMINO)-1-PYRROLIDINYL)-4-OXO-1-(2-THIAZOLYL)-
Common Name English
vosaroxin [INN]
Common Name English
AG-7352
Code English
SPC-595
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 294509
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
EU-Orphan Drug EU/3/12/990
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
NCI_THESAURUS C259
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
WHO-ATC L01XX53
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
NCI_THESAURUS C795
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID50938662
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
DRUG BANK
DB11999
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
PUBCHEM
9952884
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
WIKIPEDIA
Vosaroxin
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL68117
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
EVMPD
SUB76117
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
SMS_ID
100000137627
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
USAN
SS-107
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
MESH
C485113
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
CAS
175414-77-4
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
INN
9066
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
FDA UNII
K6A90IIZ19
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
NCI_THESAURUS
C95148
Created by admin on Wed Jul 05 23:21:52 UTC 2023 , Edited by admin on Wed Jul 05 23:21:52 UTC 2023
PRIMARY
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ACTIVE MOIETY