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Details

Stereochemistry ACHIRAL
Molecular Formula C18H19F3N2S
Molecular Weight 352.417
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIFLUPROMAZINE

SMILES

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

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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

PubMed

PubMed

TitleDatePubMed
A case report of akathisia due to triflupromazine.
1971 Apr
[Four cases of extrapyramidal effects following the treatment of hyperemesis gravidarum with triflupromazin (author's transl)].
1976 Apr
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.
1984 Sep
Aluminum balance in intensive care patients.
2001 Apr
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].
2001 Jul
Partition of N-monodemethylated phenothiazine drugs to phosphatidylcholine bilayer vesicles studied by second-derivative spectrophotometry.
2002 Jun
Interaction of protonated anticancer thiazines with water-insoluble phospholipids and antineoplastic agents.
2002 Mar-Apr
Activation of Maxi Cl(-) channels by antiestrogens and phenothiazines in NIH3T3 fibroblasts.
2002 May
Inactivation of cholinesterase induced by chlorpromazine cation radicals.
2003 Feb
Trans-cellular proliferating cell nuclear antigen gene activation in cerebral vascular smooth muscle by endothelial oxidative injury in vivo.
2003 Nov 1
Thermodynamics of partitioning of phenothiazine drugs between phosphatidylcholine bilayer vesicles and water studied by second-derivative spectrophotometry.
2003 Sep
Triflupromazine: a microbicide non-antibiotic compound.
2004
Romifidine-ketamine anaesthesia in atropine and triflupromazine pre-medicated buffalo calves.
2004 Dec
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
19F NMR spectroscopic study on the binding of triflupromazine to bovine and human serum albumins.
2004 Oct 29
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 Jan
Chlorpromazine for schizophrenia: a Cochrane systematic review of 50 years of randomised controlled trials.
2005 Oct 17
A kinetic study on the phenothiazine dependent oxidation of NADH by bovine ceruloplasmin.
2006 Feb
Effects of inorganic ions on the binding of triflupromazine and chlorpromazine to bovine serum albumin studied by spectrometric methods.
2006 Jul
Trypanosoma cruzi dihydrolipoamide dehydrogenase as target for phenothiazine cationic radicals. Effect of antioxidants.
2006 Sep
Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives.
2007 Mar 1
[Derivative spectrophotometric and NMR spectroscopic study in pharmaceutical science].
2007 Oct
Simultaneous determination of some phenothiazine derivatives in human blood by headspace solid-phase microextraction and gas chromatography with nitrogen-phosphorus detection.
2008 Nov-Dec
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
Inhibitors of clathrin-dependent endocytosis enhance TGFbeta signaling and responses.
2009 Jun 1
The effect of calmodulin antagonists on experimental scoliosis: a pinealectomized chicken model.
2009 Mar 15
Effects of chemical manipulation of mitotic arrest and slippage on cancer cell survival and proliferation.
2009 Sep 15
Phenothiazine-type antipsychotics elicit cutaneous analgesia in rats.
2010 Mar
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes.
2013 Jun
Patents
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:07:00 UTC 2019
Edited
by admin
on Tue Oct 22 06:07:00 UTC 2019
Record UNII
RO16TQF95Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIFLUPROMAZINE
HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
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
FLUOPROMAZINE
Common Name English
TRIFLUPROMAZINE [USP]
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
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
WHO-ATC N05AA05
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
WHO-VATC QN05AA05
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
NCI_THESAURUS C740
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
NCI_THESAURUS C29710
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
Code System Code Type Description
IUPHAR
4330
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
RXCUI
10805
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY RxNorm
WIKIPEDIA
TRIFLUPROMAZINE
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
INN
725
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
NCI_THESAURUS
C66635
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
HSDB
146-54-3
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
MERCK INDEX
M11123
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
205-673-6
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
EPA CompTox
146-54-3
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
ChEMBL
CHEMBL570
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
CAS
146-54-3
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
EVMPD
SUB11290MIG
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
MESH
D014273
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
PUBCHEM
5568
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
DRUG BANK
DB00508
Created by admin on Tue Oct 22 06:07:00 UTC 2019 , Edited by admin on Tue Oct 22 06:07:00 UTC 2019
PRIMARY
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