CHEBI:90225 - rubitecan

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name rubitecan
Definition A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group.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.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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
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 (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 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.
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rubitecan (CHEBI:90225) has role antineoplastic agent (CHEBI:35610)
rubitecan (CHEBI:90225) has role EC (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)
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
Rubitecan Wikipedia
View more database links
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
10200331 PubMed citation Europe PMC
11901310 PubMed citation Europe PMC
15122081 PubMed citation Europe PMC
15357630 PubMed citation Europe PMC
16370935 PubMed citation Europe PMC
21191594 PubMed citation Europe PMC
21695227 PubMed citation Europe PMC
23873658 PubMed citation Europe PMC
23934323 PubMed citation Europe PMC
24549232 PubMed citation Europe PMC
25445521 PubMed citation Europe PMC
26004006 PubMed citation Europe PMC
26487893 PubMed citation Europe PMC
Last Modified
22 February 2017