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=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
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 |
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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 |
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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 Date1959 |
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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 Date1959 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
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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 |
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The antinicotinic effects of drugs with clinically useful sedative-antianxiety properties. | 1975 |
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Trifluoroperazine for the symptomatic treatment of chorea. | 1975 Mar |
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Low urinary dopamine and prediction of phenothiazine-induced Parkinsonism: a preliminary report. | 1976 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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A new potent calmodulin antagonist with arylalkylamine structure: crystallographic, spectroscopic and functional studies. | 2000 Mar 31 |
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Calmodulin antagonists inhibit T-type Ca(2+) currents in mouse spermatogenic cells and the zona pellucida-induced sperm acrosome reaction. | 2001 Aug 1 |
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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 |
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Characterization of afloqualone N-glucuronidation: species differences and identification of human UDP-glucuronosyltransferase isoform(s). | 2005 Jan |
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Control of hepatitis C: a medicinal chemistry perspective. | 2005 Jan 13 |
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"Calm, but still alert": Marketing Stelazine to disturbed America, 1958-1980. | 2008 |
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Miscellaneous. | 2008 Oct |
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Research on antipsychotics in India. | 2010 Jan |
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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
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.
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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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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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ACTIVE MOIETY