U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C32H44F3N3O2S
Molecular Weight 591.771
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUPHENAZINE DECANOATE

SMILES

CCCCCCCCCC(=O)OCCN1CCN(CCCN2C3=C(SC4=C2C=C(C=C4)C(F)(F)F)C=CC=C3)CC1

InChI

InChIKey=VIQCGTZFEYDQMR-UHFFFAOYSA-N
InChI=1S/C32H44F3N3O2S/c1-2-3-4-5-6-7-8-14-31(39)40-24-23-37-21-19-36(20-22-37)17-11-18-38-27-12-9-10-13-29(27)41-30-16-15-26(25-28(30)38)32(33,34)35/h9-10,12-13,15-16,25H,2-8,11,14,17-24H2,1H3

HIDE SMILES / InChI

Molecular Formula C32H44F3N3O2S
Molecular Weight 591.771
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including

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.

Originator

Curator's Comment: Introduced in 1959

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FLUPHENAZINE DECANOATE

Approved Use

Fluphenazine Decanoate Injection is a long­acting parenteral antipsychotic drug intended for use in the management of patients requiring prolonged parenteral neuroleptic therapy (e.g., chronic schizophrenics).

Launch Date

5.5313282E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 ng/mL
12 mg single, oral
dose: 12 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
261 ng/mL
2.5 mg 3 times / 3 days multiple, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.52 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6.92 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.4 h
12 mg single, oral
dose: 12 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.3 h
2.5 mg 3 times / 3 days multiple, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.6%
FLUPHENAZINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
21 mg 1 times / day multiple, intramuscular (max)
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources: Page: p.315
unhealthy, 35.4+/-10.4
n = 30
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 35.4+/-10.4
Sex: M+F
Population Size: 30
Sources: Page: p.315
Disc. AE: Akathisia, Dyskinesia...
AEs leading to
discontinuation/dose reduction:
Akathisia (3.3%)
Dyskinesia (3.3%)
Hypertonia (3.3%)
Stupor (3.3%)
Sources: Page: p.315
250 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 250 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 250 mg, 1 times / week
Sources: Page: p.1438
unhealthy, 44
n = 25
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 44
Sex: M+F
Population Size: 25
Sources: Page: p.1438
100 mg single, intramuscular|subcutaneous
Recommended
Dose: 100 mg
Route: intramuscular|subcutaneous
Route: single
Dose: 100 mg
Sources:
unhealthy
Disc. AE: Tardive dyskinesia, Neuroleptic malignant syndrome...
AEs leading to
discontinuation/dose reduction:
Tardive dyskinesia
Neuroleptic malignant syndrome
Fall
Sources:
AEs

AEs

AESignificanceDosePopulation
Akathisia 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular (max)
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources: Page: p.315
unhealthy, 35.4+/-10.4
n = 30
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 35.4+/-10.4
Sex: M+F
Population Size: 30
Sources: Page: p.315
Dyskinesia 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular (max)
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources: Page: p.315
unhealthy, 35.4+/-10.4
n = 30
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 35.4+/-10.4
Sex: M+F
Population Size: 30
Sources: Page: p.315
Hypertonia 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular (max)
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources: Page: p.315
unhealthy, 35.4+/-10.4
n = 30
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 35.4+/-10.4
Sex: M+F
Population Size: 30
Sources: Page: p.315
Stupor 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular (max)
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources: Page: p.315
unhealthy, 35.4+/-10.4
n = 30
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 35.4+/-10.4
Sex: M+F
Population Size: 30
Sources: Page: p.315
Fall Disc. AE
100 mg single, intramuscular|subcutaneous
Recommended
Dose: 100 mg
Route: intramuscular|subcutaneous
Route: single
Dose: 100 mg
Sources:
unhealthy
Neuroleptic malignant syndrome Disc. AE
100 mg single, intramuscular|subcutaneous
Recommended
Dose: 100 mg
Route: intramuscular|subcutaneous
Route: single
Dose: 100 mg
Sources:
unhealthy
Tardive dyskinesia Disc. AE
100 mg single, intramuscular|subcutaneous
Recommended
Dose: 100 mg
Route: intramuscular|subcutaneous
Route: single
Dose: 100 mg
Sources:
unhealthy
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Dystonic reactions to phenothiazine derivatives.
1966 Oct
[Psuedotetanus caused by neuroleptics. Description of a case caused by fluphenazine].
1966 Sep-Oct
Side-effects of phenothiazines.
1967 Apr 1
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967 Jan
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
Schizophrenia-like reaction to diethylpropion.
1976 Nov 27
Dystonic reaction to high dose propranolol.
1977 Oct 29
High vs standard dosage fluphenazine HCL in acute schizophrenia.
1978 Nov
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
Benztropine prophylaxis of dystonic reactions.
1979 Mar 28
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
Fluphenazine pharmacokinetics and therapeutic response.
1981
Neuroleptic-induced acute dyskinesias in rhesus monkeys.
1981
Stuttering: an unusual side effect of phenothiazines.
1981 Mar
Neuroleptic-induced seizures. An in vitro technique for assessing relative risk.
1982 Feb
Sexual dysfunction in women using major tranquilizers.
1982 Sep
Occurrence of neuroleptic malignant syndrome in a narcoleptic patient.
1983 Jun
Neuroleptic malignant syndrome.
1984 Jan 7
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.
1984 Sep
A case of neuroleptic malignant syndrome in a mentally retarded adolescent.
1986 Nov
Drug-induced dystonia in young and elderly patients.
1988 Jul
Manic syndrome associated with zidovudine treatment.
1988 Jun 17
[Repeated acute dystonia following administration of metoclopramide and fluphenazine].
1988 Mar 14
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
Actions of ORG 5222 as a novel psychotropic agent.
1990 Mar
Evidence for an involvement of D1 and D2 dopamine receptors in mediating nicotine-induced hyperactivity in rats.
1991
On the selection of mice for haloperidol response and non-response.
1991
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
1991 Apr 18
Central effects of SL 82.0715, an antagonist of polyamine site of the NMDA receptor complex.
1993 Sep-Dec
Some central effects of GYKI 52466, a non-competitive AMPA receptor antagonist.
1995 Nov-Dec
Roxindole, a potential antidepressant. I. Effect on the dopamine system.
1996
Tardive dyskinesia induced by risperidone?
1996 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
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.
2007 Jul 17
Incorporating clinical guidelines through clinician decision-making.
2008 Feb 29
Relapse of tardive dyskinesia due to reduction in clozapine dose.
2009 Aug
[A case of drug-induced syndrome of inappropriate secretion of antidiuretic hormone].
2010 Jul-Aug
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
Curator's Comment: Fluphenazine Decanoate Injection may be given IM or SC
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 Wed Jul 05 22:30:27 UTC 2023
Edited
by admin
on Wed Jul 05 22:30:27 UTC 2023
Record UNII
FMU62K1L3C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUPHENAZINE DECANOATE
EP   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
Common Name English
FLUPHENAZINE DECANOATE [EP MONOGRAPH]
Common Name English
FLUPHENAZINE ENANTHATE IMPURITY C [EP IMPURITY]
Common Name English
FLUPHENAZINE DECANOATE [USP MONOGRAPH]
Common Name English
DEPOT
Brand Name English
NSC-169510
Code English
MODITEN DEPOT
Brand Name English
PROLIXIN DECANOATE
Brand Name English
LYOGEN
Brand Name English
FLUPHENAZINE DECANOATE [WHO-IP]
Common Name English
FLUPHENAZINE DECANOATE [MART.]
Common Name English
FLUPHENAZINE DECANOATE [USP IMPURITY]
Common Name English
MODECATE
Brand Name English
FLUPHENAZINE DECANOATE [ORANGE BOOK]
Common Name English
Fluphenazine decanoate [WHO-DD]
Common Name English
FLUPHENAZINE DECANOATE [MI]
Common Name English
DAPOTUM D
Brand Name English
2-[4-[3-[2-(Trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazinyl]ethyl decanoate
Systematic Name English
DECANOIC ACID, 2-(4-(3-(2-(TRIFLUOROMETHYL)-10H-DECANOATE PHENOTHIAZIN-10-YL)PROPYL)-1-PIPERAZINYL)ETHYL ESTER
Common Name English
FLUPHENAZINI DECANOAS [WHO-IP LATIN]
Common Name English
QD-10733
Code English
FLUPHENAZINE DECANOATE [VANDF]
Common Name English
FLUPHENAZINE DECANOATE [JAN]
Common Name English
SQ-10733
Code English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
Code System Code Type Description
RXCUI
25190
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY RxNorm
CHEBI
5124
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
CAS
5002-47-1
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
MESH
C011825
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
SMS_ID
100000088511
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
EVMPD
SUB02230MIG
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
MERCK INDEX
M5490
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY Merck Index
PUBCHEM
3388
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
NCI_THESAURUS
C47996
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FLUPHENAZINE DECANOATE
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY Description: A pale yellow viscous liquid or a yellow, crystalline, oily solid; odour, faint, ester-like. Miscibility: Immiscible with water; miscible with dehydrated ethanol R and ether R.Category: Neuroleptic.Storage: Fluphenazine decanoate should be kept in a well-closed container, protected from light. Additional information: Even in the absence of light, Fluphenazine decanoate is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Fluphenazine decanoate contains not less than 98.5% and not more than 101.5% of C32H44F3N3O2S, calculated with reference to the dried substance.
EPA CompTox
DTXSID7023069
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200854
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
225-672-4
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
NSC
169510
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
DAILYMED
FMU62K1L3C
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
DRUG BANK
DBSALT000776
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
DRUG CENTRAL
1213
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
FDA UNII
FMU62K1L3C
Created by admin on Wed Jul 05 22:30:27 UTC 2023 , Edited by admin on Wed Jul 05 22:30:27 UTC 2023
PRIMARY
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