Ritanserin (CHEM017836)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:41:05 UTC
Update Date2016-11-09 01:15:40 UTC
Accession NumberCHEM017836
Identification
Common NameRitanserin
ClassSmall Molecule
DescriptionA thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-(2-(4-(Bis(p-fluorophenyl)methylene)-piperidino)ethyl)-7-methyl-5H-thiazolo-(3,2-a)pyrimidin-5-oneChEBI
R 55,667ChEBI
R-55667ChEBI
RitanserinaChEBI
RitanserineChEBI
RitanserinumChEBI
TisertonKegg
6-(2-(4-(Bis(4-fluorophenyl)methylene)-1-piperidinyl)ethyl)-7-methyl-5H-thiazolo(3,2-a)pyrimidin-5-oneMeSH
Ritanserin hydrochlorideMeSH
Ritanserin tartrateMeSH
RitanserinMeSH
Chemical FormulaC27H25F2N3OS
Average Molecular Mass477.570 g/mol
Monoisotopic Mass477.169 g/mol
CAS Registry Number87051-43-2
IUPAC Name6-(2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
Traditional Nameritanserin
SMILESCC1=C(CCN2CCC(CC2)=C(C2=CC=C(F)C=C2)C2=CC=C(F)C=C2)C(=O)N2C=CSC2=N1
InChI IdentifierInChI=1S/C27H25F2N3OS/c1-18-24(26(33)32-16-17-34-27(32)30-18)12-15-31-13-10-21(11-14-31)25(19-2-6-22(28)7-3-19)20-4-8-23(29)9-5-20/h2-9,16-17H,10-15H2,1H3
InChI KeyJUQLTPCYUFPYKE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Fluorobenzene
  • Halobenzene
  • Pyrimidone
  • Aralkylamine
  • Aryl fluoride
  • Aryl halide
  • Piperidine
  • Pyrimidine
  • Thiazole
  • Heteroaromatic compound
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organofluoride
  • Organohalogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • 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 Solubility0.0098 g/LALOGPS
logP5.02ALOGPS
logP5.31ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity144.47 m³·mol⁻¹ChemAxon
Polarizability50.47 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6t-3290000000-bc5d102863d190032aedSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fc3-2900000000-aeed8cd6efbb3b93af8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2900000000-e63814b1ab90bb7dbff0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0fc3-2900000000-aeed8cd6efbb3b93af8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0120900000-2b497f82b7be60923129Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0691400000-0c8177d3e5ab3969c8e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-4964000000-91e06533d512fbdbbae9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-8551e56e48dfdf64e171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0120900000-36880e5ac2306f556ef6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-8390300000-ac0d1ec8fba9b1d3ebacSpectrum
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 IDDB12693
HMDB IDHMDB0257243
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRitanserin
Chemspider ID4896
ChEBI ID64195
PubChem Compound IDNot Available
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=11897543
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12905101
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18801405
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8974378