CHEBI:90225 - rubitecan

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ChEBI Name rubitecan
ChEBI ID CHEBI:90225
Definition A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H15N3O6
Net Charge 0
Average Mass 393.350
Monoisotopic Mass 393.09609
InChI InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
InChIKey VHXNKPBCCMUMSW-FQEVSTJZSA-N
SMILES [N+]([O-])(=O)C=1C2=CC=3CN4C(C=5COC([C@](C5C=C4C3N=C2C=CC1)(O)CC)=O)=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.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing rubitecan (CHEBI:90225) has role antineoplastic agent (CHEBI:35610)
rubitecan (CHEBI:90225) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
rubitecan (CHEBI:90225) has role prodrug (CHEBI:50266)
rubitecan (CHEBI:90225) is a δ-lactone (CHEBI:18946)
rubitecan (CHEBI:90225) is a C-nitro compound (CHEBI:35716)
rubitecan (CHEBI:90225) is a pyranoindolizinoquinoline (CHEBI:48626)
rubitecan (CHEBI:90225) is a semisynthetic derivative (CHEBI:72588)
rubitecan (CHEBI:90225) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(4S)-4-ethyl-4-hydroxy-10-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
INNs Sources
rubitecán WHO MedNet
rubitécan WHO MedNet
rubitecan ChemIDplus
rubitecanum WHO MedNet
Synonyms Sources
9-NC ChemIDplus
9-nitro-(20S)-camptothecin ChEBI
9-nitro-20(S)-camptothecin ChemIDplus
9-nitrocamptothecin ChemIDplus
RFS 2000 ChemIDplus
Brand Names Sources
Camptogen ChemIDplus
Orathecin ChemIDplus
Manual Xrefs Databases
2411 DrugCentral
D04031 KEGG DRUG
Rubitecan Wikipedia
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Registry Numbers Types Sources
5365063 Reaxys Registry Number Reaxys
91421-42-0 CAS Registry Number ChemIDplus
91421-42-0 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017