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Details

Stereochemistry ACHIRAL
Molecular Formula C21H24F3N3S
Molecular Weight 407.496
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIFLUOPERAZINE

SMILES

CN1CCN(CCCN2C3=CC=CC=C3SC4=CC=C(C=C24)C(F)(F)F)CC1

InChI

InChIKey=ZEWQUBUPAILYHI-UHFFFAOYSA-N
InChI=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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00831 | https://www.drugs.com/cdi/trifluoperazine.html | https://clinicaltrials.gov/ct2/show/NCT02600741 | http://reference.medscape.com/drug/trifluoperazine-342991

Trifluoperazine (Eskazinyl, Eskazine, Jatroneural, Modalina, Stelazine, Terfluzine, Trifluoperaz, Triftazin) is a typical antipsychotic of the phenothiazine chemical class used for the short-term treatment of certain types of anxiety. 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. The primary application of trifluoperazine is for schizophrenia. Other official indications may vary country by country, but generally, it is also indicated for use in agitation and patients with behavioral problems, severe nausea, and vomiting as well as severe anxiety. Trials have shown a moderate benefit of this drug in patients with borderline personality disorder. A 2004 meta-analysis of the studies on trifluoperazine found that it is more likely than placebo to cause extrapyramidal side effects such as akathisia, dystonia, and Parkinsonism. It is also more likely to cause somnolence and anticholinergic side effects such as red-eye and xerostomia (dry mouth).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
STELAZINE

Approved Use

For the management of schizophrenia. Trifluoperazine HCl is effective for the short-term treatment of generalized non-psychotic anxiety. However, trifluoperazine HCl is not the first drug to be used in therapy for most patients with non-psychotic anxiety because certain risks associated with its use are not shared by common alternative treatments (i.e., benzodiazepines). When used in the treatment of non-psychotic anxiety, trifluoperazine HCl should not be administered at doses of more than 6 mg per day or for longer than 12 weeks because the use of trifluoperazine HCl at higher doses or for longer intervals may cause persistent tardive dyskinesia that may prove irreversible (see WARNINGS ). The effectiveness of trifluoperazine HCl as a treatment for non-psychotic anxiety was established in a four-week clinical multicenter study of outpatients with generalized anxiety disorder (DSM-III). This evidence does not predict that trifluoperazine HCl will be useful in patients with other non-psychotic conditions in which anxiety, or signs that mimic anxiety, are found (i.e., physical illness, organic mental conditions, agitated depression, character pathologies, etc.). Trifluoperazine HCl has not been shown effective in the management of behavioral complications in patients with mental retardation.

Launch Date

1959
Primary
STELAZINE

Approved Use

For the management of schizophrenia. Trifluoperazine HCl is effective for the short-term treatment of generalized non-psychotic anxiety. However, trifluoperazine HCl is not the first drug to be used in therapy for most patients with non-psychotic anxiety because certain risks associated with its use are not shared by common alternative treatments (i.e., benzodiazepines). When used in the treatment of non-psychotic anxiety, trifluoperazine HCl should not be administered at doses of more than 6 mg per day or for longer than 12 weeks because the use of trifluoperazine HCl at higher doses or for longer intervals may cause persistent tardive dyskinesia that may prove irreversible (see WARNINGS ). The effectiveness of trifluoperazine HCl as a treatment for non-psychotic anxiety was established in a four-week clinical multicenter study of outpatients with generalized anxiety disorder (DSM-III). This evidence does not predict that trifluoperazine HCl will be useful in patients with other non-psychotic conditions in which anxiety, or signs that mimic anxiety, are found (i.e., physical illness, organic mental conditions, agitated depression, character pathologies, etc.). Trifluoperazine HCl has not been shown effective in the management of behavioral complications in patients with mental retardation.

Launch Date

1959
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.053 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIFLUOPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10.144 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIFLUOPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.9 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIFLUOPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
yes [IC50 17.6 uM]
yes [IC50 8 uM]
yes
yes
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
The antinicotinic effects of drugs with clinically useful sedative-antianxiety properties.
1975
Trifluoroperazine for the symptomatic treatment of chorea.
1975 Mar
Low urinary dopamine and prediction of phenothiazine-induced Parkinsonism: a preliminary report.
1976 Jun
Neuroleptic malignant syndrome after venlafaxine.
2000 Jan 22
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
2000 Jul 28
A new potent calmodulin antagonist with arylalkylamine structure: crystallographic, spectroscopic and functional studies.
2000 Mar 31
Calmodulin antagonists inhibit T-type Ca(2+) currents in mouse spermatogenic cells and the zona pellucida-induced sperm acrosome reaction.
2001 Aug 1
Activity of phenothiazines against antibiotic-resistant Mycobacterium tuberculosis: a review supporting further studies that may elucidate the potential use of thioridazine as anti-tuberculosis therapy.
2001 May
Characterization of afloqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s).
2005 Jan
Control of hepatitis C: a medicinal chemistry perspective.
2005 Jan 13
"Calm, but still alert": Marketing Stelazine to disturbed America, 1958-1980.
2008
Miscellaneous.
2008 Oct
Research on antipsychotics in India.
2010 Jan
Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology.
2010 Mar 3
Patents

Sample Use Guides

Initial: 2-5 mg PO q12hr Maintenance Dose: 15-20 mg/day Not to exceed 40mg/day
Route of Administration: Oral
In Vitro Use Guide
Log-phase suspension cultures of P388/S and P388/R cells were treated with ADR (Adriamycin) (0.01 to 5.0 mkg/ml) in the presence and absence of 4 mkM TFP (Trifluoperazine ) for 24 hr at 37C. Cell counts in control and treated cultures were then determined by trypan blue dye exclusion in a hemacytometer.
Name Type Language
APO-TRIFLUOPERAZINE
Preferred Name English
TRIFLUOPERAZINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENOTHIAZINE, 10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-2-(TRIFLUOROMETHYL)-
Systematic Name English
TRIFLUOPERAZINE [MI]
Common Name English
TRIFLUOPERAZINE [VANDF]
Common Name English
TRIFLUOPERAZINE [HSDB]
Common Name English
FLURAZINE
Brand Name English
NSC-17474
Code English
RP-7623
Code English
10H-PHENOTHIAZINE, 10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-2-(TRIFLUOROMETHYL)-
Systematic Name English
Trifluoperazine [WHO-DD]
Common Name English
trifluoperazine [INN]
Common Name English
NSC-46061
Code English
Classification Tree Code System Code
NDF-RT N0000007544
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
NDF-RT N0000175746
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
NCI_THESAURUS C29710
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
WHO-VATC QN05AB06
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
NDF-RT N0000007544
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
NDF-RT N0000007544
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
NCI_THESAURUS C740
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
WHO-ATC N05AB06
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
LIVERTOX NBK548927
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
Code System Code Type Description
HSDB
3195
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
MERCK INDEX
m11116
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB00831
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
LACTMED
Trifluoperazine
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID1046928
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
ChEMBL
CHEMBL422
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
CAS
117-89-5
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-219-4
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
IUPHAR
214
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
MESH
D014268
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
NCI_THESAURUS
C62084
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
INN
718
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
EVMPD
SUB11288MIG
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
CHEBI
45951
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
FDA UNII
214IZI85K3
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
PUBCHEM
5566
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
RXCUI
10800
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY RxNorm
DAILYMED
214IZI85K3
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
NSC
17474
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
SMS_ID
100000077744
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
NSC
46061
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
WIKIPEDIA
TRIFLUOPERAZINE
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY
DRUG CENTRAL
2740
Created by admin on Mon Mar 31 17:48:00 GMT 2025 , Edited by admin on Mon Mar 31 17:48:00 GMT 2025
PRIMARY