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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Deanol in the treatment of tardive dyskinesia. | 1975 Aug |
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Low urinary dopamine and prediction of phenothiazine-induced Parkinsonism: a preliminary report. | 1976 Jun |
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Drug-induced torsade de pointes. | 1985 Nov-Dec |
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The effects of chronic treatment and withdrawal of CNS depressants on aggressive behavior. | 1989 Dec |
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Pseudo-tetanus following trifluoperazine. | 1990 Oct |
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Association of high prolactin levels and neuroleptics immediately postpartum. | 1990 Winter |
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NTPase/helicase of Flaviviridae: inhibitors and inhibition of the enzyme. | 2002 |
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Characterization of PMCA isoforms and their contribution to transcellular Ca2+ flux in MDCK cells. | 2003 Jan |
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H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. | 2003 Mar |
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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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Delirium and extrapyramidal symptoms due to a lithium-olanzapine combination therapy: a case report. | 2005 Aug |
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Allosteric modulation of GABA(B) receptor function in human frontal cortex. | 2005 Jan |
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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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Transient activation and delayed inhibition of Na+,K+,Cl- cotransport in ATP-treated C11-MDCK cells involve distinct P2Y receptor subtypes and signaling mechanisms. | 2006 Oct 20 |
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Effects of age-dependent membrane transport changes on the homeostasis of senescent human red blood cells. | 2007 Aug 15 |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
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Comment on 'Topical verapamil HCL, topical trifluoroperazine, and topical magnesium sulfate for the treatment of Peyronie's disease--a placebo-controlled pilot study'. | 2007 Jul |
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Activity and post antifungal effect of chlorpromazine and trifluopherazine against Aspergillus, Scedosporium and zygomycetes. | 2007 Jul |
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Agricultural exposures and gastric cancer risk in Hispanic farm workers in California. | 2007 Jun |
|
Clozapine-induced tardive dystonia (blepharospasm). | 2007 Winter |
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"Calm, but still alert": Marketing Stelazine to disturbed America, 1958-1980. | 2008 |
|
Role of TRP channels and NCX in mediating hypoxia-induced [Ca(2+)](i) elevation in PC12 cells. | 2008 Dec 31 |
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Preservation of protein clefts in comparative models. | 2008 Jan 16 |
|
Miscellaneous. | 2008 Oct |
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Spectroscopic and electrochemical analysis of psychotropic drugs. | 2009 Jan |
|
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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A molecular model for diacylglycerol acyltransferase from Mortierella ramanniana var. angulispora. | 2009 Jun 28 |
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In vivo reorganization of the actin cytoskeleton in leaves of Nicotiana tabacum L. transformed with plastin-GFP. Correlation with light-activated chloroplast responses. | 2009 May 29 |
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The story of antipsychotics: Past and present. | 2009 Oct-Dec |
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Molecular mechanism of trifluoperazine induces apoptosis in human A549 lung adenocarcinoma cell lines. | 2009 Sep-Oct |
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Mechanism of catch force: tethering of thick and thin filaments by twitchin. | 2010 |
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Lithium, trifluperazine and idiopathic leucopenia: Author and reviewer perspectives on how to write a good case report. | 2010 Apr |
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Acute akathisia with quetiapine: A case report and review of literature. | 2010 Dec |
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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 |
|
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010 Feb 23 |
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Research on antidepressants in India. | 2010 Jan |
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Research on antipsychotics in India. | 2010 Jan |
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Inhibitory effect of chlorpromazine on RANKL-induced osteoclastogenesis in mouse bone marrow cells. | 2011 |
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Calcium signaling is involved in cadmium-induced neuronal apoptosis via induction of reactive oxygen species and activation of MAPK/mTOR network. | 2011 Apr 22 |
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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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Activity of trifluoperazine against replicating, non-replicating and drug resistant M. tuberculosis. | 2012 |
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Comparison of the effect of non-antifungal and antifungal agents on Candida isolates from the gastrointestinal tract. | 2012 Jan |
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Antitubercular pharmacodynamics of phenothiazines. | 2013 Apr |
|
Avermectin induces P-glycoprotein expression in S2 cells via the calcium/calmodulin/NF-κB pathway. | 2013 Apr 25 |
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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 |
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Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes. | 2013 Jun |
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Regorafenib impairs mitochondrial functions, activates AMP-activated protein kinase, induces autophagy, and causes rat hepatocyte necrosis. | 2015 Jan 2 |
|
In vitro selective inhibition of human UDP-glucuronosyltransferase (UGT) 1A4 by finasteride, and prediction of in vivo drug-drug interactions. | 2015 Jan 22 |
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
Fri Dec 16 16:18:36 UTC 2022
by
admin
on
Fri Dec 16 16:18:36 UTC 2022
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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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Classification Tree | Code System | Code | ||
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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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PRIMARY | Merck Index | ||
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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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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 |