CHEBI:52768 - hycanthone

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ChEBI Name hycanthone
ChEBI ID CHEBI:52768
Definition A thioxanthen-9-one compound having a hydroxymethyl substituent at the 1-position and a 2-[(diethylamino)ethyl]amino substituent at the 4-position. It was formerly used (particularly as the monomethanesulfonic acid salt) as a schistosomicide for individual or mass treatement of infection with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ulrike Wittig
Supplier Information
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Formula C20H24N2O2S
Net Charge 0
Average Mass 356.48200
InChI InChI=1S/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3
InChIKey MFZWMTSUNYWVBU-UHFFFAOYSA-N
SMILES CCN(CC)CCNc1ccc(CO)c2sc3ccccc3c(=O)c12
Roles Classification
Biological Role(s): mutagen
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.
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ChEBI Ontology
Outgoing hycanthone (CHEBI:52768) has functional parent lucanthone (CHEBI:51052)
hycanthone (CHEBI:52768) has role mutagen (CHEBI:25435)
hycanthone (CHEBI:52768) has role schistosomicide drug (CHEBI:38941)
hycanthone (CHEBI:52768) is a thioxanthenes (CHEBI:50930)
hycanthone (CHEBI:52768) is conjugate base of hycanthone(1+) (CHEBI:67141)
Incoming hycanthone(1+) (CHEBI:67141) is conjugate acid of hycanthone (CHEBI:52768)
IUPAC Name
1-{[2-(diethylamino)ethyl]amino}-4-(hydroxymethyl)-9H-thioxanthen-9-one
INNs Sources
hicantona ChemIDplus
hycanthone KEGG DRUG
hycanthone WHO MedNet
hycanthonum ChemIDplus
Synonyms Sources
1-((2-(Diethylamino)ethyl)amino)-4-(hydroxymethyl)-9H-thioxanthen-9-one ChemIDplus
1-((2-(Diethylamino)ethyl)amino)-4-(hydroxymethyl)thioxanthen-9-one ChemIDplus
1-(2-diethylaminoethylamino)-4-(hydroxymethyl)thioxanthen-9-one ChEBI
Hycanthon ChemIDplus
Hycanthone KEGG DRUG
Lucanthone metabolite ChemIDplus
Database Links Databases
D00541 KEGG DRUG
Hycanthone Wikipedia
NL6410359 Patent
US3294803 Patent
US3312598 Patent
View more database links
Registry Numbers Types Sources
1402722 Reaxys Registry Number Reaxys
1402722 Beilstein Registry Number Beilstein
3105-97-3 CAS Registry Number ChemIDplus
3105-97-3 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
1888160 PubMed citation CiteXplore
21935361 PubMed citation CiteXplore
2957147 PubMed citation CiteXplore
5573958 PubMed citation CiteXplore
626982 PubMed citation CiteXplore
7369442 PubMed citation CiteXplore
Last Modified
22 April 2013