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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 of TRIFLUPERIDOL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
0.83 nM [Ki]
1.2 µM [IC50]
69.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Triperidol
Primary
Triperidol
Primary
Triperidol

Doses

AEs

PubMed

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
Record UNII
R8869Q7R8I
Record Status Validated (UNII)
Record Version