Page last updated: 2024-12-05

fluphenazine enanthate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID3389
CHEMBL ID1200951
CHEBI ID5125
SCHEMBL ID120793
MeSH IDM0068531

Synonyms (61)

Synonym
2-(4-{3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propyl}piperazin-1-yl)ethyl heptanoate
heptanoic acid, 2-(4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)-1-piperazinyl)ethyl ester
heptanoic acid, 2-(4-(3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)propyl)-1-piperazinyl)ethyl ester
fluphenazine enanthate [jan]
4-(3-(2-trifluoromethyl-10-phenothiazinyl)propyl)-1-piperazineethanol enanthate
brn 0598595
einecs 220-385-0
moditen enanthate
2-(4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)-1-piperazinyl)ethyl heptanoate
moditen-retard
fluphenazine enantate
sq 16,114
ccris 4033
fluphenazine o-enantate
eutimox
heptanoic acid, 2-(4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)- 1-piperazinyl)ethyl ester
fluphenazine enanthate
2746-81-8
prolixin enanthate
C07955
prolixin enanthate (tn)
fluphenazine enanthate (jp17/usp)
D00792
CHEMBL1200951
flufenan
fluphenazini enantas
chebi:5125 ,
sq 16144
2-[4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]piperazin-1-yl]ethyl heptanoate
AKOS003589053
mfcd00866641
unii-qsb34yf0w9
qsb34yf0w9 ,
fluphenazine enanthate [usp:jan]
fluphenazine enantate [who-dd]
fluphenazine enantate [who-ip]
fluphenazine enanthate [vandf]
2-(4-(3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)propyl)piperazin-1-yl)ethyl heptanoate
fluphenazine enanthate [mi]
fluphenazine enantate [ep monograph]
fluphenazine decanoate impurity c [ep impurity]
fluphenazine enanthate [orange book]
fluphenazine enanthate [usp monograph]
fluphenazini enantas [who-ip latin]
fluphenazine enantate [mart.]
SCHEMBL120793
heptanoic acid, 2-[4-[3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propyl]-1-piperazinyl]ethyl ester
2-(4-(3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propyl)-1-piperazinyl)ethyl heptanoate #
2-(4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)-1-piperazinyl))ethyl heptanoate
sq-16144
DTXSID6023070 ,
J-016771
FT-0737140
Q27106667
HY-107947
CS-0030966
dtxcid403070
fluphenazine enanthate (usp:jan)
fluphenazine enantate (ep monograph)
fluphenazine enantate (mart.)
fluphenazine enanthate (usp monograph)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"5 million adverse drug reaction (ADR) reports for 8620 drugs/biologics that are listed for 1191 Coding Symbols for Thesaurus of Adverse Reaction (COSTAR) terms of adverse effects."( Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
Benz, RD; Contrera, JF; Kruhlak, NL; Matthews, EJ; Weaver, JL, 2004
)
0.32

Pharmacokinetics

ExcerptReferenceRelevance
" The enanthate produces peak plasma concentrations on days 2 to 3 and declines with an apparent elimination half-life (i."( Clinical pharmacokinetics of the depot antipsychotics.
Ereshefsky, L; Jann, MW; Saklad, SR,
)
0.13
"Precise pharmacokinetic data of long-acting neuroleptics: apparent half life (T 1/2), time of peak plasma concentration (Tmax), bioavailability, has been a major contribution to determine optimal dosage of the drug."( [Clinical pharmacokinetics of haloperidol decanoate. Comparison with other prolonged-action neuroleptics].
Levron, JC; Ropert, R,
)
0.13

Bioavailability

ExcerptReferenceRelevance
" The absorption rate constant is slower than the elimination rate constant and therefore, the depot antipsychotics exhibit 'flip-flop' kinetics where the time to steady-state is a function of the absorption rate, and the concentration at steady-state is a function of the elimination rate."( Clinical pharmacokinetics of the depot antipsychotics.
Ereshefsky, L; Jann, MW; Saklad, SR,
)
0.13
" Optimal dose has been determined from the bioavailability of the oral formulation and the interval between two injections, it averages 15, 20 times the oral daily dose for haloperidol decanoate."( [Clinical pharmacokinetics of haloperidol decanoate. Comparison with other prolonged-action neuroleptics].
Levron, JC; Ropert, R,
)
0.13

Dosage Studied

ExcerptRelevanceReference
"Precise pharmacokinetic data of long-acting neuroleptics: apparent half life (T 1/2), time of peak plasma concentration (Tmax), bioavailability, has been a major contribution to determine optimal dosage of the drug."( [Clinical pharmacokinetics of haloperidol decanoate. Comparison with other prolonged-action neuroleptics].
Levron, JC; Ropert, R,
)
0.13
" To gather relevant data on pharmacokinetic characteristics of depot fluphenazines, the authors measured plasma levels of neuroleptic activity in 76 clinic patients on stable dosage regimens of fluphenazine decanoate or fluphenazine enanthate."( Plasma levels of neuroleptic in patients receiving depot fluphenazine.
Chouinard, G; Cohen, BM; Jones, B; Sommer, BR; Waternaux, C, 1985
)
0.45
"9% of the total antipsychotic dosage on average."( Ten year outcomes of outpatients with schizophrenia on conventional depot antipsychotics: a systematic chart review.
Den, R; Mimura, M; Sakurai, H; Suzuki, T; Tsutsumi, C; Uchida, H; Uchida, T, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenothiazines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID588217FDA HLAED, serum glutamic pyruvic transaminase (SGPT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588216FDA HLAED, serum glutamic oxaloacetic transaminase (SGOT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588219FDA HLAED, gamma-glutamyl transferase (GGT) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588218FDA HLAED, lactate dehydrogenase (LDH) increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588214FDA HLAED, liver enzyme composite activity2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588215FDA HLAED, alkaline phosphatase increase2004Current drug discovery technologies, Dec, Volume: 1, Issue:4
Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID1135106Antipsychotic activity in albino rat assessed as duration of inhibition of conditioned avoidance behavior at 25 mg/kg administered intramuscularly1977Journal of medicinal chemistry, Feb, Volume: 20, Issue:2
Esters of 4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazieneethanol and related compounds as long-acting antipsychotic agents. Synthesis of the 1-adamantoate, the first crystalline base.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-199021 (72.41)18.7374
1990's0 (0.00)18.2507
2000's3 (10.34)29.6817
2010's4 (13.79)24.3611
2020's1 (3.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.05

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.05 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (11.76%)5.53%
Reviews6 (17.65%)6.00%
Case Studies5 (14.71%)4.05%
Observational0 (0.00%)0.25%
Other19 (55.88%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (10)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Evaluation of the Necessity of Long-term Pharmacological Treatment With Antipsychotics for the Prevention of Relapse in Long-term Stabilized Schizophrenic Patients: a Randomized, Single-blind, Longitudinal Trial [NCT02307396]Phase 421 participants (Actual)Interventional2015-02-01Completed
Ascending-Dose, Double-Blind, Placebo-Controlled, Bilateral Study of Intralesional Fluphenazine Decanoate in Psoriasis [NCT00356200]Phase 210 participants (Actual)Interventional2006-07-31Terminated(stopped due to Enrollment criteria met)
Phase 1b Single Arm, Open Label, Multi-Center Study of Fluphenazine HCl Monotherapy in Relapsed or Relapsed-and-Refractory Multiple Myeloma [NCT00821301]Phase 130 participants (Anticipated)Interventional2008-12-31Recruiting
A 12-Month Randomized, Open-Label Study of Caregiver Psycho-education and Skills Training in Patients Recently Diagnosed With Schizophrenia, Schizoaffective Disorder, or Schizophreniform Disorder and Receiving Paliperidone Palmitate or Oral Antipsychotic [NCT02600741]296 participants (Actual)Observational2015-07-24Completed
A Phase I/IIa, Open-Label, Dose-Escalation Study to Determine the Safety, Tolerance, and Preliminary Activity of Intravenous High-Dose Fluphenazine HCI in Patients With Advanced Multiple Myeloma [NCT00335647]Phase 1/Phase 230 participants (Anticipated)Interventional2006-01-31Completed
[NCT00161018]Phase 3150 participants Interventional2003-11-30Completed
Comparative Effectiveness of Antipsychotic Medications in Patients With Schizophrenia (CATIE Schizophrenia Trial) [NCT00014001]Phase 41,600 participants Interventional2000-12-31Completed
Comparative Effects of a D2 and Mixed D1-D2 Dopamine Antagonist on Gambling and Amphetamine Reinforcement in Pathological Gamblers and Healthy Controls [NCT02203786]Phase 260 participants (Actual)Interventional2009-09-30Completed
Pharmacovigilance in Gerontopsychiatric Patients [NCT02374567]Phase 3407 participants (Actual)Interventional2015-01-31Terminated
Ascending-Dose, Double-Blind, Placebo-Controlled, Study of Intralesional Fluphenazine Hydrochloride for Psoriasis [NCT00929578]Phase 215 participants (Actual)Interventional2008-11-30Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT00356200 (2) [back to overview]Change in Target Lesion Pruritus Visual Analog Scale (VAS) at Week 4 Compared to Baseline.
NCT00356200 (2) [back to overview]Change in Target Lesion Score at Week 4 Compared to Baseline
NCT00929578 (4) [back to overview]Change in Target Lesion Scoring Evaluated at Baseline and 4 Weeks
NCT00929578 (4) [back to overview]Change in the Target Lesion Visual Analog Scale (VAS) Score for Pruritus Evaluated at Baseline and 4 Weeks
NCT00929578 (4) [back to overview]Fluphenazine Serum Levels Measured at Baseline, 2 Hours Post Dose and 1 Week Post Dose.
NCT00929578 (4) [back to overview]Safety Outcome Measures
NCT02203786 (6) [back to overview]Betting Behaviour in Laboratory-based Slot Machine Game
NCT02203786 (6) [back to overview]Cognitive Task Performance
NCT02203786 (6) [back to overview]Diastolic Blood Pressure (DBP)
NCT02203786 (6) [back to overview]Speed of Play on Slot Machine Game
NCT02203786 (6) [back to overview]Subjective Reinforcement Self-report Scales
NCT02203786 (6) [back to overview]Winnings on Slot Machine Upon Completion of Game

Change in Target Lesion Pruritus Visual Analog Scale (VAS) at Week 4 Compared to Baseline.

Target lesion pruritus as measured by the Visual Analog Scale (VAS) from 0 to 100 mm at week 4 compared to baseline (with 0 being no pruritis and 100 being maximum pruritis). (NCT00356200)
Timeframe: Baseline to week 4

Interventionmm (Mean)
Cohort 1, 10 ug/ml Fluphenazine Treated Lesion-30
Cohort 1, Placebo Treated Lesion-27.2
Cohort 2, 100 ug/ml Fluphenazine Treated Lesion-18
Cohort 2, Placebo Treated Lesion-32.6

[back to top]

Change in Target Lesion Score at Week 4 Compared to Baseline

Change in score from 0-14 of target lesion disease activity based on scaling, erythema, and induration as determined by a physician assessor at week 4 compared to baseline (with 0 being no disease activity and 14 being maximum disease activity). (NCT00356200)
Timeframe: Baseline to week 4

Interventionunits on a scale (Mean)
Cohort 1, 10 ug/ml Fluphenazine Treated Lesion-1
Cohort 1, Placebo Treated Lesion-0.8
Cohort 2, 100 ug/ml Fluphenazine Treated Lesion-0.4
Cohort 2, Placebo Treated Lesion-1.5

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Change in Target Lesion Scoring Evaluated at Baseline and 4 Weeks

Actual change in target lesion score comparing 4 week score with baseline score. Improvement is positive, worsening is negative. Target lesions scores range from 0 (no disease) to 12 (severe disease), and are scored based on the sum of erythema (0-4), induration (0-4) and scale (0-4) scores. (NCT00929578)
Timeframe: 4 weeks

Interventionunits on a scale (Mean)
Placebo-1.4
Fluphenazine-1.4

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Change in the Target Lesion Visual Analog Scale (VAS) Score for Pruritus Evaluated at Baseline and 4 Weeks

Visual Analog Scale (VAS) score for pruritus. Subjective measurement of pruritus on an analog scale with a single mark denoting self-perceived pruritus: Minimum 0mm for no itch, Maximum 100mm for worst itch imaginable. Scores are measured in millimeters. This secondary outcome is a percentage improvement from baseline score for pruritus. Improvement is negative, worsening is positive. (NCT00929578)
Timeframe: 4 weeks

Interventionpercentage of baseline pruritus (Mean)
Placebo0.86
Fluphenazine-2.16

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Fluphenazine Serum Levels Measured at Baseline, 2 Hours Post Dose and 1 Week Post Dose.

Number of participants with fluphenazine serum levels > 0.200ng/ml, at baseline, 2 hours post dose and 1 week post dose. (NCT00929578)
Timeframe: 1 week

Interventionparticipants (Number)
Baseline0
2 Hours Post Dose2
1 Week Post Dose2

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Safety Outcome Measures

adverse events will be recorded and monitored. Adverse events will be noted in a separate chart. (NCT00929578)
Timeframe: 8 weeks

InterventionAll Study Participant (Number)
All Study Participants12

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Betting Behaviour in Laboratory-based Slot Machine Game

Risk taking was operationally defined as credits wagered per spin (mean computed for total spins) (NCT02203786)
Timeframe: 1x per test session (total of 4 test sessions) for duration of the study: 4 weeks (1 session/week)

,,,
Interventioncredits/spin on slot machine (Mean)
Mean bet under drugMean bet under placebo
Fluphenazine - Controls14.412.2
Fluphenazine - Pathological Gamblers16.016.1
Haloperidol - Controls11.69.5
Haloperidol - Pathological Gamblers12.810.4

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Cognitive Task Performance

Response time to words (gambling, alcohol, positive affect, negative affect) as a percentage of neutral categorized words (parts of a building). This provides an index of the relative salience of stimuli from these four categories against a baseline of reaction to words with no clinical relevance or emotional valence. Smaller scores indicate faster relative response time to the test stimuli vs. neutral stimuli (i.e., greater salience) (NCT02203786)
Timeframe: At key points during testing: immediately after the slot machine, at expected peak subjective-behavioral effects for amphetamine (90-minutes post-capsule administration)

,,,
Interventionpercentage of neutral categorized words (Mean)
post-slots-GAM words under drugpost-slots-ALC words under drugpost-slots POS words under drugpost-slots NEG words under drugpost-slots GAM words under placebopost-slots ALC words under placebopost-slots POS words under placebopost-slots NEG words under placebopeak AMPH GAM words under drugpeak AMPH ALC words under drugpeak AMPH POS words under drugpeak AMPH NEG words under drugpeak AMPH GAM words under placebopeak AMPH ALC words under placebopeak AMPH POS words under placebopeak AMPH NEG words under placebo
Fluphenazine - Controls91.093.188.387.992.193.386.884.797.0100.396.398.796.997.595.196.7
Fluphenazine - Pathological Gamblers94.098.195.396.595.099.094.997.295.899.598.799.497.999.997.7100.0
Haloperidol - Controls94.896.593.789.697.297.093.792.398.199.197.296.896.8100.297.898.1
Haloperidol - Pathological Gamblers91.695.591.389.191.694.892.793.096.7101.298.299.595.099.998.499.0

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Diastolic Blood Pressure (DBP)

Measure changes from baseline, especially physiologic reactivity to the slot machine and amphetamine. (NCT02203786)
Timeframe: At key points in testing: immediately after the slot machine game (change from session baseline), and at expected peak subjective-behavioral effects for amphetamine (90-minutes post-capsule administration)(change from session baseline).

,,,
Interventionmm Hg (Mean)
Drug-Change in DBP pre-to-post slot machinePlacebo-Change in DBP pre-to-post slot machineDrug-Change in DBP pre-amphetamine to peak amphPlacebo-Change in DBP pre-amphetamine to peak amp
Fluphenazine - Controls23.61932.736.3
Fluphenazine - Pathological Gamblers2221.632.135.2
Haloperidol - Controls15.119.128.526.6
Haloperidol - Pathological Gamblers20.222.527.233.6

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Speed of Play on Slot Machine Game

Number of individual spins in a 15-minute slot machine game. Each spin corresponds to one wager. (NCT02203786)
Timeframe: 15-minutes

,,,
Interventionindividual spins/15-minutes (Mean)
Spins/15-minutes under DrugSpins/15-minutes under Placebo
Fluphenazine - Controls71.866.7
Fluphenazine - Pathological Gamblers78.568.4
Haloperidol - Controls66.472.2
Haloperidol - Pathological Gamblers76.988.6

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Subjective Reinforcement Self-report Scales

Self-reported Confidence to Refrain from Gambling (0 - 10) was assessed at test session baseline, before the slot machine and after the slot machine (Phase 1); and before amphetamine and at peak amphetamine (Phase 2). The maximum score (10) denotes complete confidence to refrain from gambling (i.e., NO urge or compulsion to gamble); the minimum score (0) denotes complete lack of confidence to refrain from gambling (i.e., overwhelming urge to gamble). Scores between 10 and 0 denote intermediate confidence to refrain from gambling with LOWER scores denoting less confidence to refrain from gambling -- i.e., GREATER urge or compulsive motivation to gamble. Scores shown are based on single item visual analogue ratings 0-10 from each participant at the specified time point. The mean (SD) of these single item ratings is presented for each sub-group. (NCT02203786)
Timeframe: At key points in testing: immediately after the slot machine game, and at expected peak subjective-behavioral effects for amphetamine (90-minutes post-capsule administration).

,,,
Interventionunits on a scale (Mean)
Drug - Confidence not to gamble after slot machinePlacebo - Confidence not to gamble after slot machDrug - Confidence not to gamble at peak amphetaminPlac -Confidence not to gamble at peak amphetamine
Fluphenazine - Controls9.38.29.89.3
Fluphenazine - Pathological Gamblers4.84.86.45.7
Haloperidol - Controls9.599.89.4
Haloperidol - Pathological Gamblers4.84.25.25.5

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Winnings on Slot Machine Upon Completion of Game

Credits (NCT02203786)
Timeframe: 15-minutes

,,,
Interventioncredits (Mean)
Winnings (Final Credit Tally) under drugWinnings (Final Credit Tally) under Placebo
Fluphenazine - Controls544.3215
Fluphenazine - Pathological Gamblers277.8140.8
Haloperidol - Controls449.1339.2
Haloperidol - Pathological Gamblers239562.4

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