CHEBI:231651 - vosaroxin

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ChEBI Name vosaroxin
ChEBI ID CHEBI:231651
Definition A 1,8-naphthyridine derivative that is 1,8-naphthyridin-4(1H)-one substituted by 1,3-thiazol-2-yl, carboxy, and (3S,4S)-3-methoxy-4-(methylamino)pyrrolidin-1-yl groups at positions 1, 3, and 7, respectively. It targets topoisomerase II and induces site-selective double-strand breaks in DNA, leading to apoptosis in cancer cells.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H19N5O4S
Net Charge 0
Average Mass 401.440
Monoisotopic Mass 401.11578
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
InChIKey XZAFZXJXZHRNAQ-STQMWFEESA-N
SMILES CN[C@H]1CN(C[C@@H]1OC)C1=NC2=C(C=C1)C(=O)C(=CN2C1=NC=CS1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): topoisomerase II inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase II.
intercalator
A role played by a chemical agent which exhibits the capability of occupying space between DNA base pairs due to particular properties in size, shape and charge. Intercalation of chemical compounds in DNA helix can result in replication errors (shift, mutation) or DNA damages.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
radiosensitizing agent
A drug that makes increases the sensitivity of tumour cells to radiation therapy.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vosaroxin (CHEBI:231651) has role antineoplastic agent (CHEBI:35610)
vosaroxin (CHEBI:231651) has role apoptosis inducer (CHEBI:68495)
vosaroxin (CHEBI:231651) has role intercalator (CHEBI:24853)
vosaroxin (CHEBI:231651) has role radiosensitizing agent (CHEBI:132992)
vosaroxin (CHEBI:231651) has role topoisomerase II inhibitor (CHEBI:156203)
vosaroxin (CHEBI:231651) is a 1,3-thiazoles (CHEBI:38418)
vosaroxin (CHEBI:231651) is a 1,8-naphthyridine derivative (CHEBI:73537)
vosaroxin (CHEBI:231651) is a cyclic ketone (CHEBI:3992)
vosaroxin (CHEBI:231651) is a ether (CHEBI:25698)
vosaroxin (CHEBI:231651) is a monocarboxylic acid (CHEBI:25384)
vosaroxin (CHEBI:231651) is a pyrrolidines (CHEBI:38260)
vosaroxin (CHEBI:231651) is a quinolone (CHEBI:23765)
vosaroxin (CHEBI:231651) is a secondary amino compound (CHEBI:50995)
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
INNs Sources
vosaroxin WHO MedNet
vosaroxina WHO MedNet
vosaroxine WHO MedNet
vosaroxinum WHO MedNet
Synonyms Sources
(+)-1,4-dihydro-7-(trans-3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acid ChEBI
AG 7352 ChEBI
AG-7352 DrugBank
AG7352 ChEBI
SNS 595 ChEBI
SNS-595 DrugBank
SPC-595 DrugBank
voreloxin DrugBank
Manual Xrefs Databases
D08024 KEGG DRUG
DB11999 DrugBank
US2011312988 Patent
Vosaroxin Wikipedia
View more database links
Registry Number Type Source
175414-77-4 CAS Registry Number DrugBank
Citations Waiting for Citations Types Sources
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Last Modified
25 June 2024