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 297 Target ID: CHEMBL217 Sources: DOI: 10.1021/om901011t	Antagonist 2778
Sigma opioid receptor 63 Target ID: CHEMBL3602 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7823122 \| https://www.ncbi.nlm.nih.gov/pubmed/9223571	Blocker 537	0.83 nM [Ki]
Glutamate NMDA receptor; Grin1/Grin2b 4 Target ID: CHEMBL2096666 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9223571 \| https://www.ncbi.nlm.nih.gov/pubmed/9023267	Antagonist 2778	1.2 µM [IC50]
Glutamate NMDA receptor; Grin1/Grin2a 4 Target ID: CHEMBL2096680 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9223571	Antagonist 2778	69.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 298 Sources: https://www.tabletwise.com/triperidol-tablet	Primary	Approved 8429	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 28 Sources: http://www.medicina.ufrj.br/cursos/LH%20FROTA%20-%201%20Ed%20-%2050%20ANOS%20DE%20MEDICAMENTOS%20ANTIPSIC%D3TICOS.pdf	Primary	Approved 8429	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 8429	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.

PubMed

Title	Date	PubMed
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.	2009 Nov 1	19583963
Research on antipsychotics in India.	2010 Jan	21836703
In vitro metabolism of haloperidol and sila-haloperidol: new metabolic pathways resulting from carbon/silicon exchange.	2010 Jan	19812350
International consensus study of antipsychotic dosing.	2010 Jun	20360319

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 `Sat Dec 16 16:17:41 UTC 2023` Edited by `admin` on `Sat Dec 16 16:17:41 UTC 2023`
Record UNII	R8869Q7R8I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIFLUPERIDOL

Official Name

English

R-2498

Code

English

MCN-JR-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