Flupenthixol (CHEM002294)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (8)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:52 UTC
Update Date2026-04-05 16:05:42 UTC
Accession NumberCHEM002294
Identification
Common NameFlupenthixol
ClassSmall Molecule
DescriptionFlupentixol is an antipsychotic neuroleptic drug. It is a thioxanthene, and therefore closely related to the phenothiazines. Its primary use is as a long acting injection given two or three weekly to people with schizophrenia who have a poor compliance with medication and suffer frequent relapses of illness. It is a D1 and D2 receptor antagonist. It is not approved in the United States.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
  • Thioxanthene
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC23H27F3N2OS
Average Molecular Mass436.540 g/mol
Monoisotopic Mass436.180 g/mol
CAS Registry Number2709-56-0
IUPAC Name2-(4-{3-[(9E)-2-(trifluoromethyl)-9,9a-dihydro-4aH-thioxanthen-9-ylidene]propyl}piperazin-1-yl)ethan-1-ol
Traditional Name2-(4-{3-[(9E)-2-(trifluoromethyl)-4a,9a-dihydrothioxanthen-9-ylidene]propyl}piperazin-1-yl)ethanol
SMILES[H]\C(CCN1CCN(CCO)CC1)=C1\C2C=C(C=CC2SC2=CC=CC=C12)C(F)(F)F
InChI IdentifierInChI=1S/C23H27F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,20,22,29H,3,9-15H2/b18-5-
InChI KeyDTTVNHWDONBIKE-DVZOWYKESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thioxanthenes. These are organic polycyclic compounds containing a thioxanthene moiety, which is an aromatic tricycle derived from xanthene by replacing the oxygen atom with a sulfur atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiopyrans
Sub Class1-benzothiopyrans
Direct ParentThioxanthenes
Alternative Parents
Substituents
  • Thioxanthene
  • Thiochromane
  • Aryl thioether
  • N-alkylpiperazine
  • Alkylarylthioether
  • 1,4-diazinane
  • Piperazine
  • Thiopyran
  • Benzenoid
  • Tertiary aliphatic amine
  • 1,2-aminoalcohol
  • Tertiary amine
  • Azacycle
  • Alkanolamine
  • Thioether
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Organopnictogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility0.000346 mg/ml
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP4.12ALOGPS
logP3.54ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.71 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity120.93 m³·mol⁻¹ChemAxon
Polarizability45.23 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0201900000-73ec21fa2c7fa423d80cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2937500000-df7eb8e76ec3519db844Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-010a-3901000000-9de441d4a43c6d405a24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-ac8754cf6336195c2271Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1401900000-bee1aa4336a030e4209aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9201000000-bbbe4f3d1a218bd24204Spectrum
Toxicity Profile
Route of ExposureFairly slow and incomplete after oral administration
Mechanism of ToxicityFlupenthixol is a thioxanthene antipsychotic. The mechanism of action of Flupenthixol is not completely understood. Flupenthixol is a powerful antagonist of both D1 and D2 dopamine receptors, and an alpha-adrenergic receptor antagonist. It's antipsychotic activity is thought to be related to blocks postsynaptic dopamine receptors in the CNS.
MetabolismMainly hepatic Half Life: 19 to 39 hours
Toxicity ValuesLD50: 300 mk/kg (Oral,Mouse) (1) LD50: 791 mg/kg (Oral, Rat) (1) LD50: 87 mk/kg (Intravenous, Mouse) (1) LD50: 37 mg/kg (Intravenous, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use in the treatment of schizophrenia and depression
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 IDNot Available
PubChem Compound ID25137855
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Smith Kline & French Laboratories; British Patent 925,538; May 8, 1963.
Craig, P.N. and Zirkle, C.L.; U.S. Patent 3,282,930; November 1, 1966; assigned to Smith Kline & French Laboratories.

MSDSNot Available
General ReferencesNot Available