Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H19F3N2S.ClH |
Molecular Weight | 388.878 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)CCCN1C2=C(SC3=C1C=C(C=C3)C(F)(F)F)C=CC=C2
InChI
InChIKey=FTNWXGFYRHWUKG-UHFFFAOYSA-N
InChI=1S/C18H19F3N2S.ClH/c1-22(2)10-5-11-23-14-6-3-4-7-16(14)24-17-9-8-13(12-15(17)23)18(19,20)21;/h3-4,6-9,12H,5,10-11H2,1-2H3;1H
Triflupromazine is antipsychotic and an antiemetic drug (sold under the brand names VESPRIN) which used to management of psychoses. However, this drug was discontinued. Triflupromazine binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. Moreover, binds the muscarinic acetylcholine receptors (M1 and M2).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1678146 |
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Target ID: P08172 Gene ID: 1129.0 Gene Symbol: CHRM2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4152054 |
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Target ID: CHEMBL2056 |
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Target ID: CHEMBL217 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | VESPRIN Approved UseUsed mainly in the management of psychoses. Also used to control nausea and vomiting Launch Date1957 |
Doses
Dose | Population | Adverse events |
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800 mg 1 times / day multiple, oral Overdose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Psychotic disorders Sources: |
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150 mg 1 times / day multiple, intramuscular Recommended Dose: 150 mg, 1 times / day Route: intramuscular Route: multiple Dose: 150 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Psychotic disorders Sources: |
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3 mg 1 times / day multiple, intravenous Recommended Dose: 3 mg, 1 times / day Route: intravenous Route: multiple Dose: 3 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Nausea Sources: |
PubMed
Title | Date | PubMed |
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A case report of akathisia due to triflupromazine. | 1971 Apr |
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[Four cases of extrapyramidal effects following the treatment of hyperemesis gravidarum with triflupromazin (author's transl)]. | 1976 Apr |
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Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. | 1984 Sep |
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Aluminum balance in intensive care patients. | 2001 Apr |
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[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo]. | 2001 Jul |
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Partition of N-monodemethylated phenothiazine drugs to phosphatidylcholine bilayer vesicles studied by second-derivative spectrophotometry. | 2002 Jun |
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Interaction of protonated anticancer thiazines with water-insoluble phospholipids and antineoplastic agents. | 2002 Mar-Apr |
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Activation of Maxi Cl(-) channels by antiestrogens and phenothiazines in NIH3T3 fibroblasts. | 2002 May |
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Inactivation of cholinesterase induced by chlorpromazine cation radicals. | 2003 Feb |
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Trans-cellular proliferating cell nuclear antigen gene activation in cerebral vascular smooth muscle by endothelial oxidative injury in vivo. | 2003 Nov 1 |
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Thermodynamics of partitioning of phenothiazine drugs between phosphatidylcholine bilayer vesicles and water studied by second-derivative spectrophotometry. | 2003 Sep |
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Triflupromazine: a microbicide non-antibiotic compound. | 2004 |
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Dissociation constants of phenothiazine drugs incorporated in phosphatidylcholine bilayer of small unilamellar vesicles as determined by carbon-13 nuclear magnetic resonance spectrometric titration. | 2004 Feb 10 |
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19F NMR spectroscopic study on the binding of triflupromazine to bovine and human serum albumins. | 2004 Oct 29 |
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Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods. | 2006 Jul |
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Trypanosoma cruzi dihydrolipoamide dehydrogenase as target for phenothiazine cationic radicals. Effect of antioxidants. | 2006 Sep |
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Modification of the thermal unfolding pathways of myoglobin upon drug interaction in different aqueous media. | 2007 Dec 13 |
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Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives. | 2007 Mar 1 |
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[Derivative spectrophotometric and NMR spectroscopic study in pharmaceutical science]. | 2007 Oct |
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Energetics of binding and protein unfolding upon amphiphilic drug complexation with a globular protein in different aqueous media. | 2008 Jun 1 |
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Monitoring the (photo)genotoxicity of photosensitizer drugs: direct quantitation of single-strand breaks in deoxyribonucleic acid using an oligonucleotide chip. | 2008 Nov 1 |
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Rapid method for the determination of tranquilizers and a beta-blocker in porcine and bovine kidney by liquid chromatography with tandem mass spectrometry. | 2009 Apr 1 |
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Inhibitors of clathrin-dependent endocytosis enhance TGFbeta signaling and responses. | 2009 Jun 1 |
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Effects of chemical manipulation of mitotic arrest and slippage on cancer cell survival and proliferation. | 2009 Sep 15 |
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Experimental analyses of synergistic combinations of antibiotics with a recently recognised antibacterial agent, lacidipine. | 2010 Feb |
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NCI_THESAURUS |
C740
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CFR |
21 CFR 522.2582
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NCI_THESAURUS |
C29710
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ACTIVE MOIETY
SUBSTANCE RECORD