TRIFLUPROMAZINE HYDROCHLORIDE

US Previously Marketed

First approved in 1957

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

Structure of TRIFLUPROMAZINE HYDROCHLORIDE

Structure Search

SMILES

Cl.CN(C)CCCN1C2=CC=CC=C2SC3=CC=C(C=C13)C(F)(F)F

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H19F3N2S
Molecular Weight	352.417
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.druglib.com/activeingredient/triflupromazine

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
Muscarinic acetylcholine receptor M1 168 Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1678146	Antagonist 2849
Muscarinic acetylcholine receptor M2 121 Target ID: P08172 Gene ID: 1129.0 Gene Symbol: CHRM2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4152054	Antagonist 2849
Dopamine D1 receptor 106 Target ID: CHEMBL2056 Sources: http://www.druglib.com/activeingredient/triflupromazine/	Antagonist 2849
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: http://www.druglib.com/activeingredient/triflupromazine/	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychosis 16 Sources: http://www.druglib.com/activeingredient/triflupromazine/	Primary		Approved 8583	VESPRIN Approved Use Used mainly in the management of psychoses. Also used to control nausea and vomiting Launch Date 1957

Doses

Dose	Population	Adverse events
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: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de	unhealthy Health Status: unhealthy Sources: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de	Sources: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de
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: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de	unhealthy Health Status: unhealthy Sources: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de	Sources: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de
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: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de	unhealthy Health Status: unhealthy Sources: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de	Sources: http://www.jodrugs.com/products/39197-triflupromazine.aspx#cite4_de

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9711	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9711
eMolecules	1989361	https://www.emolecules.com/cgi-bin/more?vid=1989361
ZINC	ZINC000000538507	http://zinc15.docking.org/substances/ZINC000000538507

PubMed

Title	Date	PubMed
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes.	2013-06	23529728
The identification of inhibitors of Schistosoma mansoni miracidial transformation by incorporating a medium-throughput small-molecule screen.	2010-06	20060828
Molecularly imprinted polymers as analyte sequesters and selective surfaces for easy ambient sonic-spray ionization.	2010-04	20309446
Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology.	2010-03-03	20209133
Phenothiazine-type antipsychotics elicit cutaneous analgesia in rats.	2010-03	20434106
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.	2010-02-23	20142494
Experimental analyses of synergistic combinations of antibiotics with a recently recognised antibacterial agent, lacidipine.	2010-02	20012879
Research on antipsychotics in India.	2010-01	21836703
Mechanisms of action of antipsychotic drugs of different classes, refractoriness to therapeutic effects of classical neuroleptics, and individual variation in sensitivity to their actions: Part II.	2009-12	20514211
Effects of chemical manipulation of mitotic arrest and slippage on cancer cell survival and proliferation.	2009-09-15	19713760
Inhibitors of clathrin-dependent endocytosis enhance TGFbeta signaling and responses.	2009-06-01	19461075
Rapid method for the determination of tranquilizers and a beta-blocker in porcine and bovine kidney by liquid chromatography with tandem mass spectrometry.	2009-04-01	19286028
The effect of calmodulin antagonists on experimental scoliosis: a pinealectomized chicken model.	2009-03-15	19282733
Simultaneous determination of some phenothiazine derivatives in human blood by headspace solid-phase microextraction and gas chromatography with nitrogen-phosphorus detection.	2009-02-11	19202796
Analytical Applications of Reactions of Iron(III) and Hexacyanoferrate(III) with 2,10-Disubstituted Phenothiazines.	2009	20107561
Monitoring the (photo)genotoxicity of photosensitizer drugs: direct quantitation of single-strand breaks in deoxyribonucleic acid using an oligonucleotide chip.	2008-11-01	18675773
Energetics of binding and protein unfolding upon amphiphilic drug complexation with a globular protein in different aqueous media.	2008-06-01	18222070
Modification of the thermal unfolding pathways of myoglobin upon drug interaction in different aqueous media.	2007-12-13	18020438
[Derivative spectrophotometric and NMR spectroscopic study in pharmaceutical science].	2007-10	17917421
Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives.	2007-03-01	17188865
Trypanosoma cruzi dihydrolipoamide dehydrogenase as target for phenothiazine cationic radicals. Effect of antioxidants.	2006-09	17017892
Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods.	2006-07	16819214
A kinetic study on the phenothiazine dependent oxidation of NADH by bovine ceruloplasmin.	2006-02	16502325
Chlorpromazine for schizophrenia: a Cochrane systematic review of 50 years of randomised controlled trials.	2005-10-17	16229742
Effects of phosphatidylserine and phosphatidylethanolamine content on partitioning of triflupromazine and chlorpromazine between phosphatidylcholine-aminophospholipid bilayer vesicles and water studied by second-derivative spectrophotometry.	2005-01	15635254
Romifidine-ketamine anaesthesia in atropine and triflupromazine pre-medicated buffalo calves.	2004-12	15610485
19F NMR spectroscopic study on the binding of triflupromazine to bovine and human serum albumins.	2004-10-29	15496337
Dissociation constants of phenothiazine drugs incorporated in phosphatidylcholine bilayer of small unilamellar vesicles as determined by carbon-13 nuclear magnetic resonance spectrometric titration.	2004-02-10	14967475
Triflupromazine: a microbicide non-antibiotic compound.	2004	15362289
Trans-cellular proliferating cell nuclear antigen gene activation in cerebral vascular smooth muscle by endothelial oxidative injury in vivo.	2003-11-01	12969989
Thermodynamics of partitioning of phenothiazine drugs between phosphatidylcholine bilayer vesicles and water studied by second-derivative spectrophotometry.	2003-09	12951447
Inactivation of cholinesterase induced by chlorpromazine cation radicals.	2003-02	12747580
Partition of N-monodemethylated phenothiazine drugs to phosphatidylcholine bilayer vesicles studied by second-derivative spectrophotometry.	2002-06	12115855
Interaction of protonated anticancer thiazines with water-insoluble phospholipids and antineoplastic agents.	2002-05-17	12014679
Activation of Maxi Cl(-) channels by antiestrogens and phenothiazines in NIH3T3 fibroblasts.	2002-05	11960619
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].	2001-07	11496617
Aluminum balance in intensive care patients.	2001-04	11396781
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.	1984-09	6147851
[Four cases of extrapyramidal effects following the treatment of hyperemesis gravidarum with triflupromazin (author's transl)].	1976-04	936714
A case report of akathisia due to triflupromazine.	1971-04	5558821

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Intramuscular

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:27:37 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:37 GMT 2025`
Record UNII	9E75N4A5HM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIFLUPROMAZINE HYDROCHLORIDE

Common Name

English

MC-4703

Preferred Name

English

TRIFLUPROMAZINE HCL

Common Name

English

TRIFLUPROMAZINE HYDROCHLORIDE [VANDF]

Common Name

English

TRIFLUPROMAZINE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

NSC-14959

Code

English

TRIFLUPROMAZINE HYDROCHLORIDE [MART.]

Common Name

English

10-[3-(Dimethylamino)propyl]-2-(trifluoromethyl)phenothiazine monohydrochloride

Systematic Name

English

TRIFLUPROMAZINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

TRIFLUPROMAZINE HYDROCHLORIDE [JAN]

Common Name

English

NSC-17473

Code

English

TRIFLUPROMAZINE HYDROCHLORIDE [MI]

Common Name

English

TRIFLUPROMAZINE HYDROCHLORIDE [USP-RS]

Common Name

English

Triflupromazine hydrochloride [WHO-DD]

Common Name

English

TRIFLUPROMAZINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

10H-PHENOTHIAZINE-10-PROPANAMINE, N,N-DIMETHYL-2-(TRIFLUOROMETHYL)-, MONOHYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C740