CHEBI:63632 - topotecan

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ChEBI Name topotecan
ChEBI ID CHEBI:63632
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:9634
Supplier Information
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Formula C23H23N3O5
Net Charge 0
Average Mass 421.44580
Monoisotopic Mass 421.164
InChI InChI=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
InChIKey UCFGDBYHRUNTLO-QHCPKHFHSA-N
SMILES CC[C@@]1(O)C(=O)OCc2c1cc1-c3nc4ccc(O)c(CN(C)C)c4cc3Cn1c2=O
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing topotecan (CHEBI:63632) has role antineoplastic agent (CHEBI:35610)
topotecan (CHEBI:63632) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
topotecan (CHEBI:63632) is a pyranoindolizinoquinoline (CHEBI:48626)
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 Sources
topotecan ChemIDplus
topotecane ChemIDplus
topotecanum ChemIDplus
Synonyms Sources
9-[(dimethylamino)methyl]-10-hydroxy-(4S)-camptothecin ChEBI
Topotecan KEGG COMPOUND
Database Links Databases
C11158 KEGG COMPOUND
D08618 KEGG DRUG
DB01030 DrugBank
EP321122 Patent
LSM-5662 LINCS
Topotecan Wikipedia
TTC PDBeChem
View more database links
Registry Numbers Types Sources
123948-87-8 CAS Registry Number KEGG COMPOUND
123948-87-8 CAS Registry Number ChemIDplus
4279441 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20574789 PubMed citation Europe PMC
21255983 PubMed citation Europe PMC
21352915 PubMed citation Europe PMC
21910214 PubMed citation Europe PMC
22028494 PubMed citation Europe PMC
22075006 PubMed citation Europe PMC
22136714 PubMed citation Europe PMC
22190039 PubMed citation Europe PMC
Last Modified
25 February 2016