TRIFLUPERIDOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H23F4NO2
Molecular Weight	409.4171
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C3=CC=CC(=C3)C(F)(F)F

InChI

InChIKey=GPMXUUPHFNMNDH-UHFFFAOYSA-N

InChI=1S/C22H23F4NO2/c23-19-8-6-16(7-9-19)20(28)5-2-12-27-13-10-21(29,11-14-27)17-3-1-4-18(15-17)22(24,25)26/h1,3-4,6-9,15,29H,2,5,10-14H2

HIDE SMILES / InChI

Molecular Formula	C22H23F4NO2
Molecular Weight	409.4171
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22497960 | https://www.ncbi.nlm.nih.gov/pubmed/9223571 | Gillies, D. & Lader, M.H. (1986) Guide to the use of psychotropic drugs, page 520, retrieved from: https://books.google.ru/books?id=7NhsAAAAMAAJ | Vardanyan, R. & Hruby, V. (2006) Synthesis of Essential Drugs, page 91, retrieved from: https://books.google.ru/books?id=Jjc7KYWZdOYC | Grant, W.M. & Schuman, J.S. (1993) Toxicology of the eye, page 1465, retrieved from: https://books.google.ru/books?id=mDLYCQAAQBAJ

Trifluperidol is an antipsychotic butyrophenone derivative. It is a high-affinity sigma receptor blocker and it was strongly selective for NR1a/2B receptors. It exhibit pharmacological effects and a mechanism of action very similar to that of phenothiazines and thioxanthenes in that it blocks dopaminergic receptors. It is more selective with respect to D2 receptors. Trifluperidol is indicated for the treatment of acute and chronic schizophrenia, mania and hypomania, organic psychoses, childhood behavioral disorders, agitation in psychotic illness and motor tics. Trifluperidol has been suspected as a cause of cataract in Japan. Patients receiving trifluperidol treatment may develop a parkinsonian-like syndrome which responds to withdrawal of the drug or concurrent administration of an anti-parkinsonian drug. Acute dystonias and akathisia are other acute extrapyramidal effects; tardive dyskinesia may supervene after longer periods of treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: DOI: 10.1021/om901011t	Antagonist 2849
Sigma opioid receptor 64 Target ID: CHEMBL3602 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7823122 \| https://www.ncbi.nlm.nih.gov/pubmed/9223571	Blocker 555	0.83 nM [Ki]
Glutamate NMDA receptor; Grin1/Grin2b 5 Target ID: CHEMBL2096666 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9223571 \| https://www.ncbi.nlm.nih.gov/pubmed/9023267	Antagonist 2849	1.2 µM [IC50]
Glutamate NMDA receptor; Grin1/Grin2a 5 Target ID: CHEMBL2096680 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9223571	Antagonist 2849	69.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 305 Sources: https://www.tabletwise.com/triperidol-tablet	Primary	Approved 8583	Triperidol Approved Use Trifluperidol is indicated for the treatment of acute and chronic schizophrenia, mania and hypomania, organic psychoses, childhood behavioral disorders, agitation in psychotic illness and motor tics.
Obsessive-compulsive disorder 33 Sources: http://www.medicina.ufrj.br/cursos/LH%20FROTA%20-%201%20Ed%20-%2050%20ANOS%20DE%20MEDICAMENTOS%20ANTIPSIC%D3TICOS.pdf	Primary	Approved 8583	Triperidol Approved Use Trifluperidol is indicated for the treatment of acute and chronic schizophrenia, mania and hypomania, organic psychoses, childhood behavioral disorders, agitation in psychotic illness and motor tics.
Mania 3 Sources: Seth, S.D. (2009) Textbook Of Pharmacology, page 112, retrieved from: https://books.google.ru/books?id=51ozlZRBvQwC	Primary	Approved 8583	Triperidol Approved Use Trifluperidol is indicated for the treatment of acute and chronic schizophrenia, mania and hypomania, organic psychoses, childhood behavioral disorders, agitation in psychotic illness and motor tics.

Doses

Dose	Population	Adverse events
5 mg 3 times / day multiple, oral Studied dose Dose: 5 mg, 3 times / day Route: oral Route: multiple Dose: 5 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4389944/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4389944/	Sources: https://pubmed.ncbi.nlm.nih.gov/4389944/
6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	Other AEs: Tremor of hands, Dryness of mouth... Other AEs: Tremor of hands (6 patients) Dryness of mouth (3 patients) Dizziness (3 patients) Constipation (3 patients) Movements abnormal (2 patients) Drowsiness (3 patients) Tremor (3 patients) Nausea (2 patients) Facial spasm (3 patients) Insomnia (2 patients) Rash (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/

AEs

AE	Significance	Dose	Population
Rash	1 pt	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Insomnia	2 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Movements abnormal	2 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Nausea	2 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Constipation	3 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Dizziness	3 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Drowsiness	3 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Dryness of mouth	3 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Facial spasm	3 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Tremor	3 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/
Tremor of hands	6 patients	6 mg 1 times / day multiple, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: multiple Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5329635/

PubMed

Title	Date	PubMed
International consensus study of antipsychotic dosing.	2010-06	20360319
Research on antipsychotics in India.	2010-01	21836703
In vitro metabolism of haloperidol and sila-haloperidol: new metabolic pathways resulting from carbon/silicon exchange.	2010-01	19812350
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.	2009-11-01	19583963
Antagonism by haloperidol and its metabolites of mechanical hypersensitivity induced by intraplantar capsaicin in mice: role of sigma-1 receptors.	2009-07	19326101
Antifungals: need to search for a new molecular target.	2006-04-17	20046765
Chlorpromazine for schizophrenia: a Cochrane systematic review of 50 years of randomised controlled trials.	2005-10-17	16229742
Flupentixol and trifluperidol reduce interleukin-1 beta and interleukin-2 release by rat mixed glial and microglial cell cultures.	2004-01-05	15591644
Flupentixol and trifluperidol reduce secretion of tumor necrosis factor-alpha and nitric oxide by rat microglial cells.	2003-07	12620286
Metoclopramide and dystonic reactions in Sardinians.	1979-06-23	87799

Patents

Sample Use Guides

In Vivo Use Guide

Initial dose - 0.5 mg daily, increased at intervals of 3-4 days until improvement occurs or a total dose of 6-8 mg daily is reached.

Route of Administration: Oral

In Vitro Use Guide

The effect of neuroleptics on the release of proinflammatory cytokines (IL-1beta and IL-2) by mixed glial and microglial cell cultures was investigated. Trifluperidol at 20 and 2 uM reduced IL-beta secretion by mixed glial cultures after 3 days of exposure. Trifluperidol at 20, 2 and 0.2 uM diminished IL-beta secretion after 1 day of incubation. Trifluperidol at 20 and 2 uM reduced IL-2 release after 1 and 3 days of exposure.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:37:06 GMT 2025` Edited by `admin` on `Wed Apr 02 07:37:06 GMT 2025`
Record UNII	R8869Q7R8I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MCN-JR-2498

Preferred Name

English

TRIFLUPERIDOL

Official Name

English

R-2498

Code

English

Trifluperidol [WHO-DD]

Common Name

English

TRIFLUPERIDOL [USAN]

Common Name

English

trifluperidol [INN]

Common Name

English

TRIFLUPERIDOL [MI]

Common Name

English

NSC-170978

Code

English

TRIFLUPERIDOL [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05AD02