Hycanthone mesylate (CHEM016161)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:17:21 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016161
Identification
Common NameHycanthone mesylate
ClassSmall Molecule
DescriptionA methanesulfonate salt resulting from the reaction of equimolar amounts of hycanthone and methanesulfonic acid. It was formerly used 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with Schistosoma haematobium and S. mansoni, but due to its toxicity and concern about possible carcinogenicity, it has been replaced by other drugs such as praziquantel.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
  • IARC Carcinogens Group 3
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
EtrenolChEBI
Hycanthone methanesulfonateChEBI
Hycanthone methanesulphonateChEBI
Hycanthone monomesylateChEBI
Hycanthone monomethanesulfonateChEBI
Hycanthone monomethanesulphonateChEBI
N,N-Diethyl-2-{[4-(hydroxymethyl)-10-oxo-10H-dibenzo[b,e]thiopyran-1-yl]amino}ethanaminium methanesulfonateChEBI
N-[2-(Diethylamino)ethyl]-4-methoxy-9-oxoxanthene-1-amine monomethanesulfonateChEBI
Hycanthone methanesulfonic acidGenerator
Hycanthone methanesulphonic acidGenerator
Hycanthone monomesylic acidGenerator
Hycanthone monomethanesulfonic acidGenerator
Hycanthone monomethanesulphonic acidGenerator
N,N-Diethyl-2-{[4-(hydroxymethyl)-10-oxo-10H-dibenzo[b,e]thiopyran-1-yl]amino}ethanaminium methanesulfonic acidGenerator
N,N-Diethyl-2-{[4-(hydroxymethyl)-10-oxo-10H-dibenzo[b,e]thiopyran-1-yl]amino}ethanaminium methanesulphonateGenerator
N,N-Diethyl-2-{[4-(hydroxymethyl)-10-oxo-10H-dibenzo[b,e]thiopyran-1-yl]amino}ethanaminium methanesulphonic acidGenerator
N-[2-(Diethylamino)ethyl]-4-methoxy-9-oxoxanthene-1-amine monomethanesulfonic acidGenerator
N-[2-(Diethylamino)ethyl]-4-methoxy-9-oxoxanthene-1-amine monomethanesulphonateGenerator
N-[2-(Diethylamino)ethyl]-4-methoxy-9-oxoxanthene-1-amine monomethanesulphonic acidGenerator
Hycanthone mesylic acidGenerator
Diethyl-[2-[[4-(hydroxymethyl)-9-oxothioxanthen-1-yl]amino]ethyl]azanium;methanesulfonic acidGenerator
Diethyl-[2-[[4-(hydroxymethyl)-9-oxothioxanthen-1-yl]amino]ethyl]azanium;methanesulphonateGenerator
Diethyl-[2-[[4-(hydroxymethyl)-9-oxothioxanthen-1-yl]amino]ethyl]azanium;methanesulphonic acidGenerator
Chemical FormulaC21H28N2O5S2
Average Molecular Mass452.580 g/mol
Monoisotopic Mass452.144 g/mol
CAS Registry Number23255-93-8
IUPAC Name1-{[2-(diethylamino)ethyl]amino}-4-(hydroxymethyl)-9H-thioxanthen-9-one; methanesulfonic acid
Traditional Namehycanthone; methanesulfonic acid
SMILESCS(O)(=O)=O.CCN(CC)CCNC1=C2C(=O)C3=CC=CC=C3SC2=C(CO)C=C1
InChI IdentifierInChI=1S/C20H24N2O2S.CH4O3S/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;1-5(2,3)4/h5-10,21,23H,3-4,11-13H2,1-2H3;1H3,(H,2,3,4)
InChI KeyLOEQGPPJCCUXEJ-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
  • Methanesulfonate
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Heteroaromatic compound
  • Vinylogous amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary amine
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-7404f621ca314e4c4403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000900000-7404f621ca314e4c4403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0000900000-7404f621ca314e4c4403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-0932feaafc48757e281bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-0932feaafc48757e281bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0000900000-0932feaafc48757e281bSpectrum
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
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID24624
PubChem Compound ID31764
Kegg Compound IDC19432
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1206768
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1618027
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2266978
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2499511
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2503417
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3104567
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=6408464
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6815525
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=8375330