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=CC=CC=C3SC4=CC=C(C=C24)C(F)(F)F)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

1987
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.2 ng/mL
11.1 mg single, oral
dose: 11.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.92 ng/mL
18.5 mg 1 times / day steady-state, oral
dose: 18.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.519 ng/mL
8.57 mg single, oral
dose: 8.57 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.52 ng/mL
9.25 mg single, oral
dose: 9.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.3 ng/mL
11.1 mg single, oral
dose: 11.1 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
2.31 mg single, intravenous
dose: 2.31 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15.3 ng × h/mL
11.1 mg single, oral
dose: 11.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
22.62 ng × h/mL
18.5 mg 1 times / day steady-state, oral
dose: 18.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6.946 ng × h/mL
8.57 mg single, oral
dose: 8.57 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.92 ng × h/mL
9.25 mg single, oral
dose: 9.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.4 ng × h/mL
11.1 mg single, oral
dose: 11.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
100 ng × h/mL
2.31 mg single, intravenous
dose: 2.31 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.3 h
11.1 mg single, oral
dose: 11.1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.4 h
18.5 mg 1 times / day steady-state, oral
dose: 18.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.98 h
8.57 mg single, oral
dose: 8.57 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
13 h
9.25 mg single, oral
dose: 9.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.4 h
11.1 mg single, oral
dose: 11.1 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
2.31 mg single, intravenous
dose: 2.31 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLUPHENAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / 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
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources:
unhealthy, 35.4+/-10.4
Health Status: unhealthy
Age Group: 35.4+/-10.4
Sex: M+F
Sources:
Disc. AE: Akathisia, Dyskinesia...
AEs leading to
discontinuation/dose reduction:
Akathisia (3.3%)
Dyskinesia (3.3%)
Hypertonia (3.3%)
Stupor (3.3%)
Sources:
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:
unhealthy, 44
Health Status: unhealthy
Age Group: 44
Sex: M+F
Sources:
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
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources:
unhealthy, 35.4+/-10.4
Health Status: unhealthy
Age Group: 35.4+/-10.4
Sex: M+F
Sources:
Dyskinesia 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources:
unhealthy, 35.4+/-10.4
Health Status: unhealthy
Age Group: 35.4+/-10.4
Sex: M+F
Sources:
Hypertonia 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources:
unhealthy, 35.4+/-10.4
Health Status: unhealthy
Age Group: 35.4+/-10.4
Sex: M+F
Sources:
Stupor 3.3%
Disc. AE
21 mg 1 times / day multiple, intramuscular
Recommended
Dose: 21 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 21 mg, 1 times / day
Sources:
unhealthy, 35.4+/-10.4
Health Status: unhealthy
Age Group: 35.4+/-10.4
Sex: M+F
Sources:
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
Tardive dyskinesia induced by risperidone?
1996-06
Roxindole, a potential antidepressant. I. Effect on the dopamine system.
1996
Some central effects of GYKI 52466, a non-competitive AMPA receptor antagonist.
1995-11-01
Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine.
1995-09-05
Some behavioral effects of CNQX AND NBQX, AMPA receptor antagonists.
1995-07-01
Effects of concomitant risperidone and lithium treatment.
1995-07
Fluphenazine plasma levels, dosage, efficacy, and side effects.
1995-05
The natural course of pseudotumor cerebri in lithium-treated patients.
1994-08
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors.
1994-03
Relation of plasma fluphenazine levels to treatment response and extrapyramidal side effects in first-episode schizophrenic patients.
1994-01
Central effects of SL 82.0715, an antagonist of polyamine site of the NMDA receptor complex.
1993-09-01
Interaction between fluoxetine and neuroleptics.
1993-05
Drug-induced dystonia in young and elderly patients.
1988-07
Manic syndrome associated with zidovudine treatment.
1988-06-17
[Tardive dystonia--a case report on therapy and metaphylaxis].
1988-05
[Repeated acute dystonia following administration of metoclopramide and fluphenazine].
1988-03-14
Effects of the 5-HT3 receptor antagonist, GR38032F, on raised dopaminergic activity in the mesolimbic system of the rat and marmoset brain.
1987-12
A case of neuroleptic malignant syndrome in a mentally retarded adolescent.
1986-11
[Catatonia due to fluphenazine].
1986-04-01
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes.
1984-09
[Malignant neuroleptics syndrome].
1984-03-09
Neuroleptic malignant syndrome.
1984-01-07
Neuroleptic malignant syndrome: successful treatment with dantrolene and bromocriptine.
1983-07
Occurrence of neuroleptic malignant syndrome in a narcoleptic patient.
1983-06
Sexual dysfunction in women using major tranquilizers.
1982-09
A case of neuroleptic malignant syndrome successfully treated with amantadine.
1982-09
Neuroleptic-induced seizures. An in vitro technique for assessing relative risk.
1982-02
Intrauterine effect of phenothiazines.
1981-04-18
Stuttering: an unusual side effect of phenothiazines.
1981-03
Fluphenazine pharmacokinetics and therapeutic response.
1981
Neuroleptic-induced acute dyskinesias in rhesus monkeys.
1981
behavior of rats and mice administered active metabolites of fluphenazine, 7-hydroxy-fluphenazine and fluphenazine-sulfoxide.
1980-11
Sleep disturbance associated with fluphenazine HCl: a case report.
1979-07
Delirium associated with combined fluphenazine-clonidine therapy.
1979-05
Benztropine prophylaxis of dystonic reactions.
1979-03-28
Neuroleptics related to butaclamol. An investigation of the effects of chlorine substituents on the aromatic rings.
1978-12
High vs standard dosage fluphenazine HCL in acute schizophrenia.
1978-11
Phenothiazine-induced dystonic reaction while swimming.
1978-10-21
The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats.
1978-09-01
Dystonic reaction to high dose propranolol.
1977-10-29
Schizophrenia-like reaction to diethylpropion.
1976-11-27
Maintenance treatment of schizophrenia with long-acting fluphenazine.
1974-08
Phenothiazine-induced decompensation.
1974-01
The therapeutic use of diazepam for akathisia.
1973-07-01
Side effects of parenteral long-acting phenothiazines.
1972-01-22
Treatment of resistant schizophrenics with extreme high dosage fluphenazine hydrochloride.
1970-09-01
Side-effects of phenothiazines.
1967-04-01
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967-01
Dystonic reactions to phenothiazine derivatives.
1966-10
[Psuedotetanus caused by neuroleptics. Description of a case caused by fluphenazine].
1966-09-01
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 Mon Mar 31 17:33:30 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:30 GMT 2025
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
DAPOTUM D
Preferred 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
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 Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
Code System Code Type Description
RXCUI
25190
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY RxNorm
CHEBI
5124
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
CAS
5002-47-1
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
MESH
C011825
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
SMS_ID
100000088511
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
EVMPD
SUB02230MIG
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
MERCK INDEX
m5490
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY Merck Index
PUBCHEM
3388
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
NCI_THESAURUS
C47996
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
FLUPHENAZINE DECANOATE
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
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 Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200854
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
225-672-4
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
NSC
169510
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
DAILYMED
FMU62K1L3C
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
DRUG BANK
DBSALT000776
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
DRUG CENTRAL
1213
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
FDA UNII
FMU62K1L3C
Created by admin on Mon Mar 31 17:33:30 GMT 2025 , Edited by admin on Mon Mar 31 17:33:30 GMT 2025
PRIMARY
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