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CHEBI:63632 - topotecan

Default Structure
ChEBI IDCHEBI:63632
ChEBI Nametopotecan
Stars
DefinitionA pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.
Secondary ChEBI IDCHEBI:9634
Last Modified25 February 2016
DownloadsMolfile
FormulaC23H23N3O5
Net Charge0
Average Mass421.453
Monoisotopic Mass421.16377
SMILESCC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1
InChIInChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
InChIKeyUCFGDBYHRUNTLO-QHCPKHFHSA-N
Wikipedia
Roles Classification
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
EC 5.99.1.2 (DNA topoisomerase) inhibitor  A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
topotecan (CHEBI:63632) has role antineoplastic agent (CHEBI:35610)
topotecan (CHEBI:63632) has role antiviral agent (CHEBI:22587)
topotecan (CHEBI:63632) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
topotecan (CHEBI:63632) is a pyranoindolizinoquinoline (CHEBI:48626)
Incoming Relation(s)
topotecan hydrochloride (CHEBI:232548) has part topotecan (CHEBI:63632)
IUPAC Name 
(4S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
INNs  Source
topotecanChemIDplus
topotecaneChemIDplus
topotecanumChemIDplus
Synonyms  Source
9-[(dimethylamino)methyl]-10-hydroxy-(4S)-camptothecinChEBI
Ff-10850 (liposomal topotecan)ChEMBL
HycamptinChEMBL
NogitecanChEMBL
NSC-609699ChEMBL
NSC-641007ChEMBL
Manual XrefsDatabases
C11158KEGG COMPOUND
D08618KEGG DRUG
DB01030DrugBank
EP321122Patent
LSM-5662LINCS
TopotecanWikipedia
TTCPDBeChem
Registry NumbersSources
Reaxys:4279441Reaxys
CAS:123948-87-8ChemIDplus
CAS:123948-87-8KEGG COMPOUND
Citations