Trifluoperazine (CHEM002283)

Record Information
Version1.0
Creation Date2009-07-21 20:27:45 UTC
Update Date2026-05-14 16:50:07 UTC
Accession NumberCHEM002283
Identification
Common NameTrifluoperazine
ClassSmall Molecule
Description
Trifluoperazine is only found in individuals that have used or taken this drug. It is a phenothiazine with actions similar to chlorpromazine. It is used as an antipsychotic and an antiemetic. [PubChem]Trifluoperazine 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
Contaminant Type
  • Amine
  • Antiemetic
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Phenothiazine
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazineChEBI
10-[3-(4-METHYL-piperazin-1-yl)-propyl]-2-trifluoromethyl-10H-phenothiazineChEBI
TrifluoperazinaChEBI
TrifluoperazinumChEBI
Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazineChEBI
TrifluoroperazineChEBI
TrifluperazineChEBI
Apo-trifluoperazineKegg
TrifluoperazinHMDB
TrifluoromethylperazineHMDB
TrifluroperizineHMDB
Rhone poulenc rorer brand OF trifluoperazine hydrochlorideHMDB
Rhone-poulenc rorer brand OF trifluoperazine hydrochlorideHMDB
Trifluoperazine HCLHMDB
Allphar brand OF trifluoperazine hydrochlorideHMDB
Apotex brand OF trifluoperazine hydrochlorideHMDB
GlaxoSmithKline brand OF trifluoperazine hydrochlorideHMDB
Link brand OF trifluoperazine hydrochlorideHMDB
Psicofarma brand OF trifluoperazine hydrochlorideHMDB
SmithKline beecham brand OF trifluoperazine hydrochlorideHMDB
StelazineHMDB
TriftazinHMDB
Apo trifluoperazineHMDB
ApoTrifluoperazineHMDB
EskazineHMDB
FlupazineHMDB
Scios brand OF trifluoperazine hydrochlorideHMDB
TerfluzineHMDB
Trifluoperazine hydrochlorideHMDB
Chemical FormulaC21H24F3N3S
Average Molecular Mass407.496 g/mol
Monoisotopic Mass407.164 g/mol
CAS Registry Number117-89-5
IUPAC Name10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine
Traditional Nametrifluoperazine
SMILESCN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1
InChI IdentifierInChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3
InChI KeyZEWQUBUPAILYHI-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
  • N-methylpiperazine
  • Para-thiazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organopnictogen compound
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • 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 Point202-210°C at 6.00E-01 mm Hg
Solubility12.2 mg/L (at 24°C)
Predicted Properties
PropertyValueSource
Water Solubility0.0088 g/LALOGPS
logP4.87ALOGPS
logP4.66ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.72 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity110.98 m³·mol⁻¹ChemAxon
Polarizability41.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityTrifluoperazine 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.
MetabolismHepatic. Half Life: 10-20 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.
TreatmentTreatment is essentially symptomatic and supportive. Early gastric lavage is helpful. Keep patient under observation and maintain an open airway, since involvement of the extrapyramidal mechanism may produce dysphagia and respiratory difficulty in severe overdosage. Do not attempt to induce emesis because a dystonic reaction of the head or neck may develop that could result in aspiration of vomitus. Extrapyramidal symptoms may be treated with anti-parkinsonism drugs, barbiturates or Benadryl. See prescribing information for these products. Care should be taken to avoid increasing respiratory depression. If administration of a stimulant is desirable, amphetamine, dextroamphetamine or caffeine with sodium benzoate is recommended. Stimulants that may cause convulsions (e.g., picrotoxin or pentylenetetrazol) should be avoided. If hypotension occurs, the standard measures for managing circulatory shock should be initiated. If it is desirable to administer a vasoconstrictor, Levophed and Neo-Synephrine are most suitable. Other pressor agents, including epinephrine, are not recommended because phenothiazine derivatives may reverse the usual elevating action of these agents and cause a further lowering of blood pressure. (2)
Concentrations
Not Available
External Links
DrugBank IDDB00831
HMDB IDHMDB0014969
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDTFP
Wikipedia LinkTrifluoperazine
Chemspider ID5365
ChEBI ID45951
PubChem Compound ID5566
Kegg Compound IDC07168
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11121417
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14974020
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15722405
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19277699
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19747949
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20544963
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7404501
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9730919