Fluphenazine
Fluphenazine
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Clinical data |
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Trade names |
Prolixin, Modecate, Moditen others |
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AHFS/Drugs.com |
Monograph |
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MedlinePlus |
a682172 |
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Pregnancy category |
- AU: C
- US: C (Risk not ruled out)
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Routes of administration |
by mouth, IM, depot injection (fluphenazine decanoate) |
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ATC code |
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Legal status |
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Legal status |
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Pharmacokinetic data |
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Bioavailability |
2.7% (by mouth) |
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Metabolism |
unclear[1] |
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Biological half-life |
IM 15 hours (HCL), 7-10 days (decanoate)[1] |
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Excretion |
Urine, faeces |
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Identifiers |
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- 2-[4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol
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CAS Number |
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PubChem CID |
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IUPHAR/BPS |
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DrugBank |
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ChemSpider |
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UNII |
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KEGG |
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ChEBI |
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ChEMBL |
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ECHA InfoCard |
100.000.639 |
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Chemical and physical data |
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Formula |
C22H26F3N3OS |
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Molar mass |
437.523 g/mol |
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3D model (JSmol) |
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FC(F)(F)c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(CCO)CC4
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InChI=1S/C22H26F3N3OS/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/h1-2,4-7,16,29H,3,8-15H2 YKey:PLDUPXSUYLZYBN-UHFFFAOYSA-N Y
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Fluphenazine, sold under the brand names Prolixin among others, is an antipsychotic medication.[1] It is used in the treatment of chronic psychoses such as schizophrenia,[1][2] and appears to be about equal in effectiveness to low-potency antipsychotics like chlorpromazine.[3] It is given by mouth, injection into a muscle, or just under the skin.[1] There is also a long acting injectable version that may last for up to four weeks.[1]
Common side effects include movement problems, sleepiness, depression and increased weight.[1] Serious side effects may include neuroleptic malignant syndrome, low white blood cell levels, and the potentially permanent movement disorder tardive dyskinesia.[1] In older people with psychosis as a result of dementia it may increase the risk of dying.[1] It may also increase prolactin levels which may result in milk production, enlarged breasts in males, impotence, and the absence of menstrual periods.[1] It is unclear if it is safe for use in pregnancy.[1] Fluphenazine is a typical antipsychotic of the phenothiazine class.[1] Its mechanism of action is not entirely clear but believed to be related to its ability to block dopamine receptors.[1]
Fluphenazine came into use in 1959.[4] The injectable form is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[5] It is available as a generic medication.[1] In the United States the tablets costs between 0.22 and 0.42 USD per day for a typical dose.[1] The wholesale cost in the developing world of the long acting form is between 0.20 and 6.20 USD per injection as of 2014.[6] It was discontinued in Australia around mid 2017.[7]
Other animals
In horses, it is sometimes given by injection as an anxiety-relieving medication, though there are many negative common side effects and it is forbidden by many equestrian competition organizations.[8]
References
- 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 "fluphenazine decanoate". The American Society of Health-System Pharmacists. Retrieved Dec 1, 2015.
- ↑ "Product Information: Modecate (Fluphenazine Decanoate Oily Injection)" (PDF). TGA eBusiness Services. Bristol-Myers Squibb Australia Pty Ltd. 1 November 2012. Retrieved 9 December 2013.
- ↑ Tardy, M; Huhn, M; Engel, RR; Leucht, S (Aug 3, 2014). "Fluphenazine versus low-potency first-generation antipsychotic drugs for schizophrenia.". The Cochrane database of systematic reviews. 8: CD009230. PMID 25087165. doi:10.1002/14651858.CD009230.pub2.
- ↑ McPherson, Edwin M. (2007). Pharmaceutical Manufacturing Encyclopedia. (3rd ed.). Burlington: Elsevier. p. 1680. ISBN 9780815518563.
- ↑ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016.
- ↑ "Fluphenazine Decanoate". International Drug Price Indicator Guide. Retrieved 2 December 2015.
- ↑ Rossi, S, ed. (July 2017). "Fluphenazine - Australian Medicines Handbook". Australian Medicines Handbook. Adelaide, Australia: Australian Medicines Handbook Pty Ltd. Retrieved 8 August 2017.
- ↑ Loving, DVM, Nancy S. (31 March 2012). "Effects of Behavior-Modifying Drug Investigated (AAEP 2011)". TheHorse.com. The Horse Media Group. Retrieved 13 December 2016.
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mACh |
- Antagonists: 3-Quinuclidinyl benzilate
- 4-DAMP
- Aclidinium bromide
- Anisodamine
- Anisodine
- Antihistamines (first-generation) (e.g., brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine (pyrilamine), phenindamine, pheniramine, promethazine, tripelennamine, triprolidine)
- Atropine
- Atropine methonitrate
- Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, zotepine)
- Benactyzine
- Benzatropine (benztropine)
- Benzilylcholine mustard
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Caramiphen
- Cloperastine
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine (dicycloverine)
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine (ethybenztropine)
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba toxin 3
- Mamba toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-piperidyl benzilate
- N-Methyl-3-piperidyl benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pipenzolate bromide
- Piperidolate
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- Revefenacin
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine (hyoscine)
- Sofpironium bromide
- Solifenacin
- Telenzepine
- Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
- Timepidium bromide
- Tiotropium bromide
- Tolterodine
- Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nortriptyline, protriptyline, trimipramine)
- Trihexyphenidyl
- Tripitamine
- Tropacine
- Tropatepine
- Tropicamide
- Typical antipsychotics (e.g., chlorpromazine, loxapine, thioridazine)
- WIN-2299
- Xanomeline
- Zamifenacin
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nACh |
- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Choline
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Ivermectin
- Levamisole
- Lobeline
- MEM-63,908 (RG-3487)
- Morantel
- Nicotine (tobacco)
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- RJR-2429
- Sazetidine A
- SB-206553
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberyldicholine
- Suxamethonium (succinylcholine)
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
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ChAT |
- Inhibitors: 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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AChE | |
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BChE |
- Inhibitors: Cymserine
- Many of the AChE inhibitors listed above
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See also: Receptor/signaling modulators |
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D1-like | |
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D2-like | |
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- See also: Receptor/signaling modulators
- Adrenergics
- Serotonergics
- Monoamine reuptake inhibitors
- Monoamine releasing agents
- Monoamine metabolism modulators
- Monoamine neurotoxins
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H1 |
- Non-generational: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, RP-5063, ziprasidone, zotepine)
- Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline)
- Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine)
- Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene)
- Unknown/unsorted: Belarizine
- Elbanizine
- Flotrenizine
- Napactadine
- Tagorizine
- Trelnarizine
- Trenizine
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H2 | |
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H3 | |
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H4 | |
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See also: Receptor/signaling modulators • Monoamine metabolism modulators • Monoamine reuptake and release modulators |
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Simple piperazines (no additional rings) | |
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Phenylpiperazines |
- Acaprazine
- Antrafenine
- Aripiprazole
- Batoprazine
- Bifeprunox
- BRL-15,572
- Ciprofloxacin
- CSP-2503
- Dapiprazole
- DCPP
- DMPP
- Diphenylpiperazine
- Dropropizine
- EGIS-12,233
- Elopiprazole
- Eltoprazine
- Enpiprazole
- Ensaculin
- Etoperidone
- Flesinoxan
- Flibanserin
- Fluprazine
- Itraconazole
- Ketoconazole
- Levodropropizine
- Lorpiprazole
- mCPP
- Mefway
- MeOPP
- Mepiprazole
- Naftopidil
- Naluzotan
- Naphthylpiperazine
- Nefazodone
- Niaprazine
- Oxypertine
- Pardoprunox
- pCPP
- pFPP
- Posaconazole
- S-14,506
- S-14,671
- S-15,535
- SB-258,585
- SB-271,046
- SB-357,134
- SB-399,885
- Sonepiprazole
- TFMPP
- Tolpiprazole
- Trazodone
- Urapidil
- Vesnarinone
- Vilazodone
- Vortioxetine
- WAY-100,135
- WAY-100,635
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Benzylpiperazines | |
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Diphenylalkylpiperazines (benzhydrylalkylpiperazines) | |
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Pyrimidinylpiperazines | |
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Pyridinylpiperazines | |
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Benzo(iso)thiazolylpiperazines | |
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Tricyclics (piperazine attached via side chain) | |
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Others/Uncategorized | |
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