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| Targets |
Fluphenazine Decanoate targets dopamine D2 receptors in the central nervous system. It acts as a postsynaptic dopamine D2 receptor antagonist, blocking the actions of dopamine. This prevents the overstimulation of dopamine receptors in the mesolimbic and mesocortical pathways, thereby reducing the hallucinations and delusions associated with schizophrenia. Fluphenazine decanoate is a high and continuous dopamine D2 receptor blocker, which contributes to its potent antipsychotic effects. It may also have some affinity for other receptors, but its primary therapeutic effect is mediated through D2 receptor antagonism.
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| ln Vitro |
In human fibroblast cells, fluphenazine decanoate exhibits action against Toxoplasma gondii, with an IC50 value of 1.7 mM[1].
In vitro, fluphenazine decanoate is a dopamine D2 receptor antagonist. As a prodrug, it is hydrolyzed to its active form, fluphenazine, which binds to and blocks dopamine D2 receptors. In receptor binding assays, fluphenazine displaces radiolabeled ligands from D2 receptors with high affinity. The compound's antipsychotic activity is correlated with its D2 receptor occupancy. In cell-based assays, fluphenazine can inhibit dopamine-stimulated cAMP accumulation in cells expressing D2 receptors, confirming its antagonist activity at the receptor level. |
| ln Vivo |
In monkey models, long-term treatment with the antipsychotic fluphenazine decanoate (0.22 mg/kg, then 0.33 mg/kg; IM; 8 times every 3 weeks) increases dopamine sensitivity [2]. In order to create a pharmacological model of human tardive dyskinesia, fluphenazine decanoate (25 mg/kg; intramuscular injection; six times every three weeks; 24 weeks) causes oral movements in rats [3]. In adult male rats, fluphenazine decanoate (1, 2, 3 mg/kg/d; SC; 60 days) causes hyperprolactinemia with gonadotropins and has antifertility effects[4].
In vivo, fluphenazine decanoate is used clinically as a long-acting antipsychotic for the management of schizophrenia. It is administered via deep intramuscular injection, where it is slowly released from the injection site and hydrolyzed to active fluphenazine. This provides sustained antipsychotic effect over several weeks, improving medication adherence in patients with chronic schizophrenia. By blocking dopamine D2 receptors, it reduces positive symptoms of schizophrenia such as hallucinations and delusions. It may also have effects on negative symptoms, though to a lesser extent. |
| Enzyme Assay |
Non-cellular in vitro assays for fluphenazine decanoate involve receptor binding studies. A standard protocol uses membrane preparations from cells expressing recombinant human dopamine D2 receptors. The membranes are incubated with a radiolabeled ligand, such as [³H]spiperone or [³H]raclopride, and varying concentrations of fluphenazine or its active metabolite. Non-specific binding is determined in the presence of an excess of unlabeled haloperidol. After incubation, the reaction is terminated by rapid filtration, and the radioactivity bound to the membranes is measured. The Ki or IC50 values are calculated from the competition curves.
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| Cell Assay |
Cellular assays for fluphenazine decanoate are performed using cell lines expressing dopamine D2 receptors, such as CHO cells or HEK293 cells stably transfected with the receptor. Cells are pre-incubated with fluphenazine at various concentrations and then stimulated with a dopamine agonist (e.g., quinpirole). The inhibition of agonist-stimulated cAMP accumulation is measured using a competitive ELISA or a homogeneous time-resolved fluorescence (HTRF) assay. The IC50 for antagonism is determined from the concentration-response curve.
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| Animal Protocol |
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) rat (250 g) [3]
Doses: 25 mg/kg Route of Administration: intramuscularinjection of hind limbs; 24-week Experimental Results: Result in spontaneous chewing movements and mandibular tremors. Animal/Disease Models: adult male rats [4] Doses: 1, 2, 3 mg/kg/d Route of Administration: 10:00-12:00 h subcutaneous injection; 60-day Experimental Results: On the 60th day, serum prolactin levels increased High, serum LH and FSH levels are suppressed. The level of hypothalamic tyrosine hydroxylase increases and chromatin decondensation is enhanced, leading to DNA denaturation. In vivo animal studies for fluphenazine decanoate are conducted in rodent models of antipsychotic activity, such as the apomorphine-induced climbing behavior test or the conditioned avoidance response test. Rats or mice are administered fluphenazine decanoate via intramuscular injection at doses such as 70.1 mg/kg. The inhibition of apomorphine-induced climbing behavior is measured as an indicator of D2 receptor antagonism. Catalepsy may also be assessed as a measure of extrapyramidal side effects. The duration of action is evaluated by testing at various time points post-injection. |
| ADME/Pharmacokinetics |
Fluphenazine decanoate has a molecular weight of 591.77 and a molecular formula of C32H44F3N3O2S. It is a lipophilic prodrug that is formulated in oil for intramuscular injection. After injection, it is slowly released from the oil depot and hydrolyzed by esterases to active fluphenazine. The elimination half-life of fluphenazine decanoate is prolonged, allowing for dosing every 2-4 weeks. It is extensively metabolized in the liver and excreted in urine and feces. The compound is stored as a powder at -20°C for up to 3 years.
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| Toxicity/Toxicokinetics |
Fluphenazine decanoate has a well-characterized toxicity profile as a typical antipsychotic. Common side effects include extrapyramidal symptoms (EPS) such as dystonia, parkinsonism, akathisia, and tardive dyskinesia. Other side effects include sedation, dry mouth, blurred vision, constipation, and orthostatic hypotension. Neuroleptic malignant syndrome (NMS) is a rare but serious adverse effect. The drug is contraindicated in patients with severe central nervous system depression, coma, or blood dyscrasias. It should be used with caution in elderly patients and those with cardiovascular disease.
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| References |
[1]. Goodwin DG, et al. Evaluation of five antischizophrenic agents against Toxoplasma gondii in human cell cultures. J Parasitol. 2011 Feb;97(1):148-51.
[2]. Lifshitz K, et al. Effects of dopamine agonists on Cebus apella monkeys with previous long-term exposure to fluphenazine. Biol Psychiatry. 1997 Mar 15;41(6):657-67. [3]. Stoessl AJ, et al. Chronic neuroleptic-induced mouth movements in the rat: suppression by CCK and selective dopamine D1 and D2 receptor antagonists. Psychopharmacology (Berl). 1989;98(3):372-9. [4]. Gill-Sharma MK, et al. Antifertility effects of fluphenazine in adult male rats. J Endocrinol Invest. 2003 Apr;26(4):316-26. |
| Additional Infomation |
Fluphenazine decanoate is a prodrug of fluphenazine, an antipsychotic drug used to treat psychotic symptoms in patients with schizophrenia. It is a phenothiazine antipsychotic, a prodrug, and a dopaminergic antagonist. It belongs to the phenothiazine class of compounds, decanoates, organofluorine compounds, and N-alkylpiperazines. Its function is related to that of fluphenazine. Fluphenazine decanoate is the decanoate form of fluphenazine, a phenothiazine drug with antipsychotic activity. Fluphenazine decanoate works by blocking postsynaptic dopamine D2 receptors in the limbic system, cortical system, and basal ganglia. This blocks the action of dopamine, thereby reducing hallucinations and delusions associated with schizophrenia.
Fluphenazine Decanoate is a clinically approved long-acting antipsychotic used for the management of schizophrenia. It is a high-potency typical antipsychotic that blocks postsynaptic dopamine D2 receptors. The decanoate ester formulation allows for depot intramuscular administration, providing sustained antipsychotic effect over several weeks. This improves medication adherence in patients with chronic schizophrenia. The drug is available in injectable formulations and is typically administered every 2-4 weeks. Fluphenazine decanoate is on the WHO Model List of Essential Medicines. |
| Molecular Formula |
C32H44F3N3O2S
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|---|---|
| Molecular Weight |
591.77
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| Exact Mass |
591.311
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| CAS # |
5002-47-1
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| Related CAS # |
Fluphenazine dihydrochloride;146-56-5;Fluphenazine decanoate dihydrochloride;2376-65-0
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| PubChem CID |
3388
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| Appearance |
Light yellow to yellow <30°C solid powder,>32°C liquid
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| Density |
1.149 g/cm3
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| Boiling Point |
658.1ºCat 760 mmHg
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| Melting Point |
30-32°
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| Flash Point |
351.8ºC
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| Index of Refraction |
1.537
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| LogP |
7.94
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
16
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| Heavy Atom Count |
41
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| Complexity |
765
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VIQCGTZFEYDQMR-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
2-[4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]piperazin-1-yl]ethyl decanoate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~211.23 mM)
Ethanol : ~50 mg/mL (~84.49 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.08 mg/mL (1.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.08 mg/mL (1.83 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.08 mg/mL (1.83 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6898 mL | 8.4492 mL | 16.8985 mL | |
| 5 mM | 0.3380 mL | 1.6898 mL | 3.3797 mL | |
| 10 mM | 0.1690 mL | 0.8449 mL | 1.6898 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00356200 | TERMINATEDWITH RESULTS | Drug: Fluphenazine Decanoate
Drug: Placebo |
Psoriasis | Tufts Medical Center | 2006-07 | Phase 2 |
| NCT05766007 | RECRUITING | Antipsychotic Agents Breastfeeding Drug Exposure Via Breast Milk Drug Exposure in Utero |
University of Liverpool | 2023-08-01 | ||
| NCT00014001 | COMPLETED | Drug: perphenazine Drug: olanzapine Drug: quetiapine |
Schizophrenia | National Institute of Mental Health (NIMH) | 2000-12 | Phase 4 |
| NCT02203786 | COMPLETEDWITH RESULTS | Drug: Haloperidol Drug: Fluphenazine Drug: Dexedrine |
Pathological Gambling | Centre for Addiction and Mental Health | 2009-09 | Phase 2 |
| NCT01323205 | COMPLETED | Drug: JNJ-40411813 Drug: JNJ-40411813 Drug: Placebo Drug: Antipsychotic medication |
Schizophrenia | Janssen Research & Development, LLC | 2011-05 | Phase 2 |
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