Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H24N2O2S.C2H6O3S |
| Molecular Weight | 466.614 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCS(O)(=O)=O.CCN(CC)CCNC1=CC=C(CO)C2=C1C(=O)C3=C(S2)C=CC=C3
InChI
InChIKey=MFJJATAOPXFYNI-UHFFFAOYSA-N
InChI=1S/C20H24N2O2S.C2H6O3S/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;1-2-6(3,4)5/h5-10,21,23H,3-4,11-13H2,1-2H3;2H2,1H3,(H,3,4,5)
| Molecular Formula | C20H24N2O2S |
| Molecular Weight | 356.482 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C2H6O3S |
| Molecular Weight | 110.132 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Hycanthone is a thioxanthene derivative of lucanthone with anti-schistosomal activity and potential antineoplastic activity. It was clinically available for the treatment of human schistosomiasis. Anti-helmintic action relies on its ability to inhibit worm monoamine oxidase and cholinesterases. Hycanthone produced immediate side effects such as hepatotoxicity and gastrointestinal disturbances, and was consequently withdrawn. Hycanthone inhibits apurinic endonuclease-1 (APE1) by direct protein binding. Hycanthone was used in the 1980s as antitumor agents, it was pulled out of Phase II trials.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: UniProtKB: Q71SU7 (Carboxylic ester hydrolase) |
|||
Target ID: GO:0097621 |
|||
Target ID: CHEMBL5619 |
80.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Hycanthone Approved Usehuman schistosomiasis |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015-01-05 |
|
| RNA interference in Schistosoma mansoni schistosomula: selectivity, sensitivity and operation for larger-scale screening. | 2010-10-19 |
|
| Identification of novel p53 pathway activating small-molecule compounds reveals unexpected similarities with known therapeutic agents. | 2010-09-27 |
|
| Reduced susceptibility to praziquantel among naturally occurring Kenyan isolates of Schistosoma mansoni. | 2009-08-18 |
|
| Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening. | 2009-07-14 |
|
| Mefloquine--an aminoalcohol with promising antischistosomal properties in mice. | 2009 |
|
| The NIH-NIAID schistosomiasis resource center. | 2008-07-30 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Long-term hepatocellular effects of hycanthone and of two other anti-Schistosomal drugs in mice infected with Schistosoma mansoni. | 1976-06 |
Patents
Sample Use Guides
Human schistosomiasis: single intramuscular dose (3.0, 2.5, 2.0, 1.5, and 1.0 mg/kg body weight).Unresectable pancreatic cancer: hycanthone was administered 60 mg/m2 intravenously within 2 to 4 hr during each day of the 5-day course of infusions during the first and fifth weeks of radiation therapy.
Route of Administration:
Other
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
IOB67KGQ3N
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| Record Status |
Validated (UNII)
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| Record Version |
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