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CHEBI:144046 - diflomotecan

ChEBI IDCHEBI:144046
ChEBI Namediflomotecan
Stars
DefinitionAn organic heteropentacyclic compound that is (5R)-8-[(6,7-difluoroquinolin-3-yl)methyl]-5-ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine moiety is joined to position 3 of the difluoroquinoine ring by a single bond. An E-ring modified camptothecin analogue that has greater lactone stability in plasma compared with other topoisomerase I inhibitors.
Last Modified3 July 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H16F2N2O4
Net Charge0
Average Mass398.365
Monoisotopic Mass398.10781
SMILESCC[C@@]1(O)CC(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(F)c(F)cc3nc2-1
InChIInChI=1S/C21H16F2N2O4/c1-2-21(28)7-18(26)29-9-12-13(21)5-17-19-11(8-25(17)20(12)27)3-10-4-14(22)15(23)6-16(10)24-19/h3-6,28H,2,7-9H2,1H3/t21-/m1/s1
InChIKeyLFQCJSBXBZRMTN-OAQYLSRUSA-N
Roles Classification
Biological Role:
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)
diflomotecan (CHEBI:144046) has functional parent (R)-homocamptothecin (CHEBI:144047)
diflomotecan (CHEBI:144046) has role antineoplastic agent (CHEBI:35610)
diflomotecan (CHEBI:144046) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
diflomotecan (CHEBI:144046) is a organic heteropentacyclic compound (CHEBI:38164)
diflomotecan (CHEBI:144046) is a organofluorine compound (CHEBI:37143)
diflomotecan (CHEBI:144046) is a organonitrogen heterocyclic compound (CHEBI:38101)
diflomotecan (CHEBI:144046) is a tertiary alcohol (CHEBI:26878)
diflomotecan (CHEBI:144046) is a ε-lactone (CHEBI:50239)
IUPAC Name 
(5R)-5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione
INNs  Source
diflomotecanWHO MedNet
diflomotecanumWHO MedNet
diflomotecánWHO MedNet
diflomotécanWHO MedNet
Synonyms  Source
(5R)-5-ethyl-9,10-difluoro-1,4,5,13-tetrahydro-5-hydroxy-3H,15H-oxepino(3',4':6,7)indolizino(1,2-b)quinoline-3,15-dioneChemIDplus
BN80915ChEBI
BN-80915ChEBI
BN 80915ChEBI
Registry NumbersSources
CAS:220997-97-7ChemIDplus
Citations