TRIFLUPROMAZINE

First approved in 1957

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H19F3N2S
Molecular Weight	352.417
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCCN1C2=C(SC3=C1C=C(C=C3)C(F)(F)F)C=CC=C2

InChI

InChIKey=XSCGXQMFQXDFCW-UHFFFAOYSA-N

InChI=1S/C18H19F3N2S/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

HIDE SMILES / InChI

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 169 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 2778
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 2778
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: http://www.druglib.com/activeingredient/triflupromazine/	Antagonist 2778
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: http://www.druglib.com/activeingredient/triflupromazine/	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychosis 16 Sources: http://www.druglib.com/activeingredient/triflupromazine/	Primary		Approved 8429	VESPRIN Approved Use Used mainly in the management of psychoses. Also used to control nausea and vomiting Launch Date -3.87935994E11

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 Condition: Psychotic disorders 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 Condition: Psychotic disorders 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 Condition: Nausea 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
ZINC	ZINC000000538507	http://zinc15.docking.org/substances/ZINC000000538507
eMolecules	1989361	https://www.emolecules.com/cgi-bin/more?vid=1989361

PubMed

Title	Date	PubMed
[Four cases of extrapyramidal effects following the treatment of hyperemesis gravidarum with triflupromazin (author's transl)].	1976 Apr	936714
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.	1984 Sep	6147851
Partition of N-monodemethylated phenothiazine drugs to phosphatidylcholine bilayer vesicles studied by second-derivative spectrophotometry.	2002 Jun	12115855
Activation of Maxi Cl(-) channels by antiestrogens and phenothiazines in NIH3T3 fibroblasts.	2002 May	11960619
Chlorpromazine for schizophrenia: a Cochrane systematic review of 50 years of randomised controlled trials.	2005 Oct 17	16229742
Trypanosoma cruzi dihydrolipoamide dehydrogenase as target for phenothiazine cationic radicals. Effect of antioxidants.	2006 Sep	17017892
Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives.	2007 Mar 1	17188865
[Derivative spectrophotometric and NMR spectroscopic study in pharmaceutical science].	2007 Oct	17917421
Simultaneous determination of some phenothiazine derivatives in human blood by headspace solid-phase microextraction and gas chromatography with nitrogen-phosphorus detection.	2008 Nov-Dec	19202796
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	19286028
Inhibitors of clathrin-dependent endocytosis enhance TGFbeta signaling and responses.	2009 Jun 1	19461075
The effect of calmodulin antagonists on experimental scoliosis: a pinealectomized chicken model.	2009 Mar 15	19282733
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.	2010 Feb 23	20142494
Changes in clinical trials methodology over time: a systematic review of six decades of research in psychopharmacology.	2010 Mar 3	20209133

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 `Fri Dec 15 15:01:58 UTC 2023` Edited by `admin` on `Fri Dec 15 15:01:58 UTC 2023`
Record UNII	RO16TQF95Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIFLUPROMAZINE

Official Name

English

TRIFLUPROMAZINE [MI]

Common Name

English

TRIFLUPROMAZINE [MART.]

Common Name

English

Triflupromazine [WHO-DD]

Common Name

English

triflupromazine [INN]

Common Name

English

VESPRIN

Brand Name

English

TRIFLUPROMAZINE [USP MONOGRAPH]

Common Name

English

FLUOPROMAZINE

Common Name

English

10-3-(Dimethylamino)propyl-2-(trifluoromethyl)phenothiazine

Systematic Name

English

TRIFLUPROMAZINE [HSDB]

Common Name

English

TRIFLUPROMAZINE [ORANGE BOOK]

Common Name

English

TRIFLUPROMAZINE [VANDF]

Common Name

English

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

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 520.2582