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Details

Stereochemistry ACHIRAL
Molecular Formula C22H26F3N3OS.C4H4O4
Molecular Weight 553.594
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FLUPHENAZINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.OCCN1CCN(CCCN2C3=CC=CC=C3SC4=CC=C(C=C24)C(F)(F)F)CC1

InChI

InChIKey=NKGQWGWZXIYMHO-BTJKTKAUSA-N
InChI=1S/C22H26F3N3OS.C4H4O4/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29;5-3(6)1-2-4(7)8/h1-2,4-7,16,29H,3,8-15H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C22H26F3N3OS
Molecular Weight 437.522
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fluphenazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Fluphenazine has not been shown effective in the management of behaviorial complications in patients with mental retardation. Fluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Psuedotetanus caused by neuroleptics. Description of a case caused by fluphenazine].
1966 Sep-Oct
Treatment of resistant schizophrenics with extreme high dosage fluphenazine hydrochloride.
1970 Sep-Oct
Side effects of parenteral long-acting phenothiazines.
1972 Jan 22
The therapeutic use of diazepam for akathisia.
1973 Jul-Aug
Maintenance treatment of schizophrenia with long-acting fluphenazine.
1974 Aug
Phenothiazine-induced decompensation.
1974 Jan
Dystonic reaction to high dose propranolol.
1977 Oct 29
The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats.
1978 Sep-Oct
Sleep disturbance associated with fluphenazine HCl: a case report.
1979 Jul
Delirium associated with combined fluphenazine-clonidine therapy.
1979 May
behavior of rats and mice administered active metabolites of fluphenazine, 7-hydroxy-fluphenazine and fluphenazine-sulfoxide.
1980 Nov
Intrauterine effect of phenothiazines.
1981 Apr 18
[Catatonia due to fluphenazine].
1986 Apr 1
A case of neuroleptic malignant syndrome in a mentally retarded adolescent.
1986 Nov
Drug-induced dystonia in young and elderly patients.
1988 Jul
[Tardive dystonia--a case report on therapy and metaphylaxis].
1988 May
Prolonged fever without extrapyramidal symptoms during neuroleptic treatment.
1989 Jun
Behavioral and electroencephalographic effects of a depot type neuroleptic fluphenazine decanoate, in rats.
1989 Nov
Fluphenazine dose, clinical response, and extrapyramidal symptoms during acute treatment.
1990 Aug
Affective disorder following use of phenylpropanolamine.
1990 Mar
Actions of ORG 5222 as a novel psychotropic agent.
1990 Mar
On the selection of mice for haloperidol response and non-response.
1991
Blockade of both D-1 and D-2 dopamine receptors may induce catalepsy in mice.
1991
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
1991 Apr 18
Interaction between fluoxetine and neuroleptics.
1993 May
Central effects of SL 82.0715, an antagonist of polyamine site of the NMDA receptor complex.
1993 Sep-Dec
The natural course of pseudotumor cerebri in lithium-treated patients.
1994 Aug
Relation of plasma fluphenazine levels to treatment response and extrapyramidal side effects in first-episode schizophrenic patients.
1994 Jan
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors.
1994 Mar
Effects of concomitant risperidone and lithium treatment.
1995 Jul
Some behavioral effects of CNQX AND NBQX, AMPA receptor antagonists.
1995 Jul-Aug
Fluphenazine plasma levels, dosage, efficacy, and side effects.
1995 May
Some central effects of GYKI 52466, a non-competitive AMPA receptor antagonist.
1995 Nov-Dec
Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine.
1995 Sep 5
Roxindole, a potential antidepressant. I. Effect on the dopamine system.
1996
Tardive dyskinesia induced by risperidone?
1996 Jun
The neuroleptic drug, fluphenazine, blocks neuronal voltage-gated sodium channels.
2006 Aug 23
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Hybrid approach for the design of highly affine and selective dopamine D(3) receptor ligands using privileged scaffolds of biogenic amine GPCR ligands.
2007 Dec 1
Neuroleptic-induced dysphagia: case report and literature review.
2007 Jan
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Incorporating clinical guidelines through clinician decision-making.
2008 Feb 29
Relapse of tardive dyskinesia due to reduction in clozapine dose.
2009 Aug
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.
2010 Feb 23
An insight into the sialotranscriptome of the brown dog tick, Rhipicephalus sanguineus.
2010 Jul 22
[A case of drug-induced syndrome of inappropriate secretion of antidiuretic hormone].
2010 Jul-Aug
Long-acting injectable antipsychotics: focus on olanzapine pamoate.
2010 Jun 24
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Antitubercular pharmacodynamics of phenothiazines.
2013 Apr
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes.
2013 Jun
Patents

Sample Use Guides

In Vivo Use Guide
For most patients, a dose of 12.5 to 25 mg (0.5 to 1 mL) may be given to initiate therapy.
Route of Administration: Intramuscular
In Vitro Use Guide
30uM Fluphenazine inhibited the high-threshold Ca2 channel current in rat sympathetic neurons (blocking by 66%).
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:49:52 UTC 2019
Edited
by admin
on Tue Oct 22 00:49:52 UTC 2019
Record UNII
97151695PW
Record Status Validated (UNII)
Record Version
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Name Type Language
FLUPHENAZINE MALEATE
JAN   WHO-DD  
Common Name English
FLUPHENAZINE MALEATE [JAN]
Common Name English
2-(4-(3-(2-(TRIFLUOROMETHYL)PHENOTHIAZIN-10-YL)PROPYL)PIPERAZIN-1-YL)ETHANOL (Z)-BUT-2-ENEDIOIC ACID (1:1)
Systematic Name English
FLUPHENAZINE MALEATE [WHO-DD]
Common Name English
FLUOROPHENAZINE MALEATE
Systematic Name English
Code System Code Type Description
ChEMBL
CHEMBL1200951
Created by admin on Tue Oct 22 00:49:52 UTC 2019 , Edited by admin on Tue Oct 22 00:49:52 UTC 2019
PRIMARY
CAS
78126-11-1
Created by admin on Tue Oct 22 00:49:52 UTC 2019 , Edited by admin on Tue Oct 22 00:49:52 UTC 2019
PRIMARY
EVMPD
SUB22373
Created by admin on Tue Oct 22 00:49:52 UTC 2019 , Edited by admin on Tue Oct 22 00:49:52 UTC 2019
PRIMARY
PUBCHEM
5282479
Created by admin on Tue Oct 22 00:49:52 UTC 2019 , Edited by admin on Tue Oct 22 00:49:52 UTC 2019
PRIMARY
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ACTIVE MOIETY