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
SMILES
CN1CCN(CCCN2C3=CC(=CC=C3SC4=C2C=CC=C4)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
Molecular Formula | C21H24F3N3S |
Molecular Weight | 407.496 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator'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
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).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
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Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
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Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
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Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26372073 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | STELAZINE Approved UseFor 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-3.38083185E11 |
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Primary | STELAZINE Approved UseFor 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-3.38083185E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.053 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3137618 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.144 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3137618 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3137618 |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: abstract |
no | |||
Page: 230.0 |
yes [IC50 17.6 uM] | |||
Page: abstract |
yes [IC50 8 uM] | |||
Page: abstract |
yes | |||
Page: abstract |
yes | |||
Page: abstract |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 607.0 |
likely | |||
Page: 60.0 |
yes | |||
Page: 3.0 |
yes | |||
Page: 24.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1369.0 |
PubMed
Title | Date | PubMed |
---|---|---|
The antinicotinic effects of drugs with clinically useful sedative-antianxiety properties. | 1975 |
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Low urinary dopamine and prediction of phenothiazine-induced Parkinsonism: a preliminary report. | 1976 Jun |
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Extra pyramidal side effects associated with paroxetine. | 1992 Dec |
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Antitubercular activity of trifluoperazine, a calmodulin antagonist. | 1992 Oct 1 |
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Fits and starts. | 1998 Nov |
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In vitro susceptibility testing of Mycobacterium tuberculosis strains to trifluoperazine. | 1999 Jun |
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Neuroleptic malignant syndrome after venlafaxine. | 2000 Jan 22 |
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Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds. | 2000 Jul 28 |
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Atypical antipsychotics: mechanism of action. | 2002 Feb |
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Novel protein kinase induced during sporangial cleavage in the oomycete Phytophthora infestans. | 2002 Oct |
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Characterization of PMCA isoforms and their contribution to transcellular Ca2+ flux in MDCK cells. | 2003 Jan |
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Acute dystonia caused by low dosage of olanzapine. | 2003 Spring |
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New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
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Altered inducible nitric oxide synthase expression and nitric oxide production in the bladder of cats with feline interstitial cystitis. | 2005 Feb |
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Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates. | 2005 Nov |
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Steady-state kinetics and inhibitory action of antitubercular phenothiazines on mycobacterium tuberculosis type-II NADH-menaquinone oxidoreductase (NDH-2). | 2006 Apr 28 |
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Hydrogen peroxide inhibits IL-12 p40 induction in macrophages by inhibiting c-rel translocation to the nucleus through activation of calmodulin protein. | 2006 Feb 15 |
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Effect of the flavonol quercetin on ion transport in the isolated intestine of the eel, Anguilla anguilla. | 2006 May |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
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Agricultural exposures and gastric cancer risk in Hispanic farm workers in California. | 2007 Jun |
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Clozapine-induced tardive dystonia (blepharospasm). | 2007 Winter |
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Physiological hydrostatic pressure protects endothelial monolayer integrity. | 2008 Jan |
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Interaction of antagonists with calmodulin: insights from molecular dynamics simulations. | 2008 Jun 12 |
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Finding my faith. | 2009 Jan |
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Structure of the inhibitor W7 bound to the regulatory domain of cardiac troponin C. | 2009 Jun 23 |
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The story of antipsychotics: Past and present. | 2009 Oct-Dec |
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Mechanism of catch force: tethering of thick and thin filaments by twitchin. | 2010 |
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Allosteric effects of the antipsychotic drug trifluoperazine on the energetics of calcium binding by calmodulin. | 2010 Aug 1 |
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Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010 Dec |
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A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010 Feb 23 |
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Inhibitory effect of chlorpromazine on RANKL-induced osteoclastogenesis in mouse bone marrow cells. | 2011 |
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Terpenoids inhibit Candida albicans growth by affecting membrane integrity and arrest of cell cycle. | 2011 Oct 15 |
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Comparison of the effect of non-antifungal and antifungal agents on Candida isolates from the gastrointestinal tract. | 2012 Jan |
|
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis. | 2013 Feb |
|
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes. | 2013 Jun |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6861140
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:40:38 UTC 2023
by
admin
on
Wed Jul 05 22:40:38 UTC 2023
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Record UNII |
214IZI85K3
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000007544
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NDF-RT |
N0000175746
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NCI_THESAURUS |
C29710
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WHO-VATC |
QN05AB06
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NDF-RT |
N0000007544
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NDF-RT |
N0000007544
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NCI_THESAURUS |
C740
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WHO-ATC |
N05AB06
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LIVERTOX |
NBK548927
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3195
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M11116
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DB00831
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Trifluoperazine
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DTXSID1046928
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CHEMBL422
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117-89-5
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204-219-4
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214
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D014268
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C62084
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718
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SUB11288MIG
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45951
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214IZI85K3
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5566
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10800
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214IZI85K3
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17474
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100000077744
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46061
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TRIFLUOPERAZINE
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2740
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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ACTIVE MOIETY |