Hycanthone (CHEM016727)

Record Information
Version1.0
Creation Date2016-05-22 03:41:38 UTC
Update Date2026-08-20 06:03:01 UTC
Accession NumberCHEM016727
Identification
Common NameHycanthone
ClassSmall Molecule
Description
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with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-((2-(Diethylamino)ethyl)amino)-4-(hydroxymethyl)-9H-thioxanthen-9-oneChEBI
1-((2-(Diethylamino)ethyl)amino)-4-(hydroxymethyl)thioxanthen-9-oneChEBI
1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)thioxanthen-9-oneChEBI
HicantonaChEBI
HycanthonChEBI
HycanthonumChEBI
Lucanthone metaboliteChEBI
Chemical FormulaC20H24N2O2S
Average Molecular Mass356.480 g/mol
Monoisotopic Mass356.156 g/mol
CAS Registry Number3105-97-3
IUPAC Name1-{[2-(diethylamino)ethyl]amino}-4-(hydroxymethyl)-9H-thioxanthen-9-one
Traditional Namehycanthone
SMILESCCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(CO)C=C1
InChI IdentifierInChI=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
InChI KeyMFZWMTSUNYWVBU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiochromenes. These are organosulfur compounds that are analogues to chromene, with the difference that are sulfur atom replaces the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiochromenes
Sub ClassNot Available
Direct ParentThiochromenes
Alternative Parents
Substituents
  • Thiochromene
  • 1-benzothiopyran
  • Benzothiopyran
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary amine
  • Alcohol
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.87ALOGPS
logP3.74ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)14.79ChemAxon
pKa (Strongest Basic)8.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.57 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.79 m³·mol⁻¹ChemAxon
Polarizability40.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0253234
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHycanthone
Chemspider ID3508
ChEBI ID52768
PubChem Compound ID3634
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1888160
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21935361
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2957147
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=5573958
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=626982
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7369442