Fluphenazine (CHEM002232)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (17)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:16 UTC
Update Date2016-11-09 01:08:43 UTC
Accession NumberCHEM002232
Identification
Common NameFluphenazine
ClassSmall Molecule
DescriptionFluphenazine is only found in individuals that have used or taken this drug. It is a phenothiazine used in the treatment of psychoses. Its properties and uses are generally similar to those of chlorpromazine. [PubChem]Fluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Phenothiazine
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-(2-Hydroxyethyl)-4-(3-(trifluoromethyl-10-phenothiazinyl)propyl)-piperazineChEBI
10-(3'-(4''-(beta-Hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazineChEBI
10-(3-(2-Hydroxyethyl)piperazinopropyl)-2-(trifluoromethyl)phenothiazineChEBI
2-(4-(3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl)-1-piperazinyl)ethanolChEBI
2-(Trifluoromethyl)-10-(3-(1-(beta-hydroxyethyl)-4-piperazinyl)propyl)phenothiazineChEBI
4-(3-(-Trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanolChEBI
4-(3-(2-(Trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-1-piperazineethanolChEBI
4-(3-(2-Trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanolChEBI
FlufenazinaChEBI
FluorfenazineChEBI
FluorophenazineChEBI
FluorphenazineChEBI
FluphenazinumChEBI
TriflumethazineChEBI
ModitenKegg
10-(3'-(4''-(b-Hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazineGenerator
10-(3'-(4''-(Β-hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazineGenerator
2-(Trifluoromethyl)-10-(3-(1-(b-hydroxyethyl)-4-piperazinyl)propyl)phenothiazineGenerator
2-(Trifluoromethyl)-10-(3-(1-(β-hydroxyethyl)-4-piperazinyl)propyl)phenothiazineGenerator
Fluphenazine decanoateHMDB
Fluphenazine hydrochlorideHMDB
LyogenHMDB
ProlixinHMDB
Hydrochloride, fluphenazineHMDB
FlufenazinHMDB
Chemical FormulaC22H26F3N3OS
Average Molecular Mass437.522 g/mol
Monoisotopic Mass437.175 g/mol
CAS Registry Number69-23-8
IUPAC Name2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethan-1-ol
Traditional Namefluphenazine
SMILESOCCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1
InChI IdentifierInChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2
InChI KeyPLDUPXSUYLZYBN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • N-alkylpiperazine
  • Para-thiazine
  • 1,4-diazinane
  • Benzenoid
  • Piperazine
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Alkanolamine
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point224-226°C (Salt)
Boiling Point268-274°C at 5.00E-01 mm Hg
Solubility31.1 mg/L (at 37°C)
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP4.4ALOGPS
logP3.97ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.95 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity117.27 m³·mol⁻¹ChemAxon
Polarizability44.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0bu4-9430100000-8ccf208ff236ff33462cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0bu4-9430100000-8ccf208ff236ff33462cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-5545900000-cdc372e9bc4eddfcf306Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0kfx-7374900000-19e721adf0c41ac35702Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0190000000-cf20413d597a3759305dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0310900000-a2a4be9e30f6506c9359Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0190000000-cf20413d597a3759305dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-007c-0911400000-e777fb408b0f7c2a2c88Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-0000900000-f3e326fb412f9c344ad9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0101900000-fb12e05240ff28e3f762Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-3714900000-faf32fabda604029301cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7934100000-f37950a800425ffc5ec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-d99d8367eb6a2ea7f9a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05r9-0198700000-1fae13d1c97088459b86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4490000000-017cae32ebc88bd742e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-1e7f5c7b20d4dd89afecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0201900000-1ca0886fa19d2ddcb4e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02p0-2925100000-3b2029bac39308857df0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-1cfdc24aa6524056f3c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0001900000-1c043e72b51e2f5a44dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0195100000-b2cce57b45399e5b895aSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2391100000-6928faa0b341426b2c11Spectrum
Toxicity Profile
Route of ExposureOral, Intramuscular
Mechanism of ToxicityFluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor management of manifestations of psychotic disorders.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00623
HMDB IDHMDB0014761
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluphenazine
Chemspider ID3255
ChEBI ID5123
PubChem Compound ID3372
Kegg Compound IDC07010
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Ullyot, G.E.; U.S. Patent 3,058,979; October 16, 1962; assigned to Smith Kline & French
Laboratories.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13950763
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16117689
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16839522
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25595294
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=5128930