CHEBI:51052 - lucanthone

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ChEBI Name lucanthone
Definition A thioxanthen-9-one compound having a methyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. Formerly used for the treatment of schistosomiasis. It is a prodrug, being metabolised to hycanthone.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6552, CHEBI:19039
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Formula C20H24N2OS
Net Charge 0
Average Mass 340.48200
Monoisotopic Mass 340.161
InChI InChI=1S/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3
SMILES CCN(CC)CCNc1ccc(C)c2sc3ccccc3c(=O)c12
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.
EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
Application(s): schistosomicide drug
Drugs that used to treat infestations by flukes (trematodes) of the genus Schistosoma.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lucanthone (CHEBI:51052) has role adjuvant (CHEBI:60809)
lucanthone (CHEBI:51052) has role antineoplastic agent (CHEBI:35610)
lucanthone (CHEBI:51052) has role EC (DNA topoisomerase) inhibitor (CHEBI:50276)
lucanthone (CHEBI:51052) has role EC [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
lucanthone (CHEBI:51052) has role mutagen (CHEBI:25435)
lucanthone (CHEBI:51052) has role photosensitizing agent (CHEBI:47868)
lucanthone (CHEBI:51052) has role prodrug (CHEBI:50266)
lucanthone (CHEBI:51052) has role schistosomicide drug (CHEBI:38941)
lucanthone (CHEBI:51052) is a thioxanthenes (CHEBI:50930)
Incoming hycanthone (CHEBI:52768) has functional parent lucanthone (CHEBI:51052)
INNs Sources
lucanthone ChemIDplus
lucanthone WHO MedNet
lucanthonum ChemIDplus
lucantona ChemIDplus
Synonyms Sources
1-((2-(diethylamino)ethyl)amino)-4-methylthioxanthen-9-one ChemIDplus
1-diethylaminoethylethylamino-4-methyl-thioxanthenone ChEBI
1-{[2-(diethylamino)ethyl]amino}-4-methylthioxanthen-9-one ChEBI
Database Links Databases
1616 DrugCentral
DB04967 DrugBank
HMDB0015607 HMDB
Lucanthone Wikipedia
View more database links
Registry Numbers Types Sources
312369 Beilstein Registry Number Beilstein
312369 Reaxys Registry Number Reaxys
479-50-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21148553 PubMed citation Europe PMC
21935361 PubMed citation Europe PMC
4368942 PubMed citation Europe PMC
6887199 PubMed citation Europe PMC
9169823 PubMed citation Europe PMC
Last Modified
22 February 2017