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Revision as of 07:58, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit		Latest revision as of 20:12, 14 November 2024 edit undoCitation bot (talk | contribs)Bots5,391,401 edits Altered volume. Added issue. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Thioxanthene antipsychotics | #UCB_Category 5/5
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			{{Short description|Typical antipsychotic drug of the thioxanthene class}}
			{{cs1 config|name-list-style=vanc}}
	{{Drugbox		{{Drugbox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 407230655
			| verifiedrevid = 457784839
	| IUPAC_name = (''EZ'')-2-propyl]piperazin-1-yl]ethanol
			| IUPAC_name = ''(EZ)''-2-propyl]piperazin-1-yl]ethanol
	| image = E-Z-Isomers of Flupentixol.png
			| image = Flupentixol structure.svg
			| width = 250
	<!--Clinical data-->		<!--Clinical data-->
	| tradename =		| tradename = Depixol, Fluanxol
	| Drugs.com = {{drugs.com|CONS|flupentixol}}		| Drugs.com = {{drugs.com|CONS|flupentixol}}
	| pregnancy_category =		| pregnancy_AU = C
			| legal_AU = S4
			| legal_BR = C1
			| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
			| legal_UK = POM
			| legal_CA = Rx-only
	| legal_status = Rx-only		| legal_status = Rx-only
	| routes_of_administration = Oral, IM		| routes_of_administration = Oral, ] (including a ])
			| class = ]
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| bioavailability =		| bioavailability = 40–55% (oral)<ref name = EMC/>
	| protein_bound =		| protein_bound =
			| metabolism = Gut wall, ]<ref>{{cite journal | vauthors = Jann MW, Ereshefsky L, Saklad SR | title = Clinical pharmacokinetics of the depot antipsychotics | journal = Clinical Pharmacokinetics | volume = 10 | issue = 4 | pages = 315–333 | date = July–August 1985 | pmid = 2864156 | doi = 10.2165/00003088-198510040-00003 | s2cid = 12848774 }}</ref>
	| metabolism =
			| elimination_half-life = 35 hours<ref name = EMC>{{cite web|title=Depixol Tablets 3mg - Summary of Product Characteristics (SPC)|date=27 December 2012|work=electronic Medicines Compendium|publisher = Lundbeck Ltd|access-date=20 October 2013|url=http://www.medicines.org.uk/emc/medicine/1076/SPC/Depixol+Tablets+3mg/}}</ref>
	| elimination_half-life = 19-39 hours
			| excretion = ] (negligible)<ref>{{cite journal | vauthors = Balant-Gorgia AE, Balant L | title = Antipsychotic drugs. Clinical pharmacokinetics of potential candidates for plasma concentration monitoring | journal = Clinical Pharmacokinetics | volume = 13 | issue = 2 | pages = 65–90 | date = August 1987 | pmid = 2887326 | doi = 10.2165/00003088-198713020-00001 | s2cid = 24707620 }}</ref>
	| excretion =
	<!--Identifiers-->		<!--Identifiers-->
	| CASNo_Ref = {{cascite|correct|CAS}}		| CAS_number_Ref = {{cascite|correct|CAS}}
	| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 2709-56-0		| CAS_number = 2709-56-0
	| ATC_prefix = N05		| ATC_prefix = N05
	| ATC_suffix = AF01		| ATC_suffix = AF01
	| PubChem = 5281881		| PubChem = 5281881
			| IUPHAR_ligand = 968
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
	| DrugBank = <!-- blanked - oldvalue: APRD00388 -->
			| DrugBank = DB00875
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4445173		| ChemSpiderID = 4445173
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|changed|FDA}}
	| UNII = FA0UYH6QUO		| UNII = 21HMQ851IS
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D01044		| KEGG = D01044
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 42055 -->		| ChEMBL = 42055
	| chemical_formula = C<sub>23</sub>H<sub>25</sub>F<sub>3</sub>N<sub>2</sub>OS
			<!--Chemical data-->
	| molecular_weight = 434.5219 g/mol
			| C=23 | H=25 | F=3 | N=2 | O=1 | S=1
	| smiles = FC(F)(F)c2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN4CCN(CCO)CC4		| smiles = FC(F)(F)c2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN4CCN(CCO)CC4
	| InChI = 1/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5-
	| InChIKey = NJMYODHXAKYRHW-DVZOWYKEBC
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5-		| StdInChI = 1S/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5-
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	}}		}}
	'''Flupentixol''' (]), also known as '''flupenthixol''' (former ]), marketed under brand names such as '''Depixol''' and '''Fluanxol''', is a ] ] of the ] class. In addition to single drug preparations, it is also available as Anxiset, Deanxit, Mixit, a combination product containing both ] and flupentixol.		'''Flupentixol''' (]), also known as '''flupenthixol''' (former ]), marketed under brand names such as '''Depixol''' and '''Fluanxol''' is a ] ] of the ] class. It was introduced in 1965 by ]. In addition to single drug preparations, it is also available as ]—a ] containing both ] (a ]) and flupentixol (marketed as Deanxit).
			Flupentixol is not approved for use in the United States. It is, however, approved for use in the ],<ref name="BNF">{{cite book | isbn = 978-0-85711-084-8 | title = British National Formulary (BNF) | last1 = Joint Formulary Committee | year = 2013 | publisher = Pharmaceutical Press | location = London, UK | edition = 65 | url-access = registration | url = https://archive.org/details/bnf65britishnati0000unse }}</ref> ],<ref name="AMH">{{cite book | editor = Rossi, S | isbn = 978-0-9805790-9-3 | title = Australian Medicines Handbook | place = Adelaide | publisher = The Australian Medicines Handbook Unit Trust | year = 2013 | edition = 2013 }}</ref> ], ],<ref>{{cite web|title=Fluanxol® (flupentixol) Tablets Registration Certificate|url=http://grls.rosminzdrav.ru/Grls_View.aspx?idReg=5644&isOld=1&t=|publisher=Russian State Register of Medicinal Products|access-date=29 July 2014}}</ref> ], ], ], ], ], and various other countries.
	== Indications ==		== Medical uses ==
			Flupentixol's main use is as a long-acting injection given once in every two or three weeks to individuals with ] who have poor compliance with medication and have frequent relapses of illness, though it is also commonly given as a tablet. There is little formal evidence to support its use for this indication but it has been in use for over fifty years.<ref name = BNF/><ref>{{cite journal | vauthors = Shen X, Xia J, Adams CE | title = Flupenthixol versus placebo for schizophrenia | journal = The Cochrane Database of Systematic Reviews | volume = 2012 | pages = CD009777 | date = November 2012 | issue = 11 | pmid = 23152280 | doi = 10.1002/14651858.CD009777.pub2 | editor1-last = Shen | editor1-first = Xiaohong | pmc = 11531908 }}</ref>
			Flupentixol is also used in low doses as an ].<ref name = BNF/><ref name="pmid7291129">{{cite journal | vauthors = Robertson MM, Trimble MR | title = The antidepressant action of flupenthixol | journal = The Practitioner | volume = 225 | issue = 1355 | pages = 761–763 | date = May 1981 | pmid = 7291129 }}</ref><ref name="pmid6674820">{{cite journal | vauthors = Pöldinger W, Sieberns S | title = Depression-inducing and antidepressive effects of neuroleptics. Experiences with flupenthixol and flupenthixol decanoate | journal = Neuropsychobiology | volume = 10 | issue = 2–3 | pages = 131–136 | year = 1983 | pmid = 6674820 | doi = 10.1159/000117999 }}</ref><ref name="pmid369298">{{cite journal | vauthors = Johnson DA | title = A double-blind comparison of flupenthixol, nortriptyline and diazepam in neurotic depression | journal = Acta Psychiatrica Scandinavica | volume = 59 | issue = 1 | pages = 1–8 | date = January 1979 | pmid = 369298 | doi = 10.1111/j.1600-0447.1979.tb06940.x | s2cid = 144717662 }}</ref><ref name="pmid773506">{{cite journal | vauthors = Young JP, Hughes WC, Lader MH | title = A controlled comparison of flupenthixol and amitriptyline in depressed outpatients | journal = British Medical Journal | volume = 1 | issue = 6018 | pages = 1116–1118 | date = May 1976 | pmid = 773506 | pmc = 1639983 | doi = 10.1136/bmj.1.6018.1116 }}</ref><ref name="pmid961463">{{cite journal | vauthors = Fujiwara J, Ishino H, Baba O, Hanaoka M, Sasaki K | title = Effect of flupenthixol on depression with special reference to combination use with tricyclic antidepressants. An uncontrolled pilot study with 45 patients | journal = Acta Psychiatrica Scandinavica | volume = 54 | issue = 2 | pages = 99–105 | date = August 1976 | pmid = 961463 | doi = 10.1111/j.1600-0447.1976.tb00101.x | s2cid = 25364795 }}</ref><ref name="pmid7093597">{{cite journal | vauthors = Tam W, Young JP, John G, Lader MH | title = A controlled comparison of flupenthixol decanoate injections and oral amitriptyline in depressed out-patients | journal = The British Journal of Psychiatry | volume = 140 | issue = 3 | pages = 287–291 | date = March 1982 | pmid = 7093597 | doi = 10.1192/bjp.140.3.287 | s2cid = 30537435 }}</ref> There is tentative evidence that it reduces the rate of deliberate ], among those who self-harm repeatedly.<ref>{{cite journal | vauthors = Hawton K, Witt KG, Taylor Salisbury TL, Arensman E, Gunnell D, Hazell P, Townsend E, van Heeringen K | display-authors = 6 | title = Pharmacological interventions for self-harm in adults | journal = The Cochrane Database of Systematic Reviews | volume = 2015 | issue = 7 | pages = CD011777 | date = July 2015 | pmid = 26147958 | pmc = 8637297 | doi = 10.1002/14651858.CD011777 | hdl-access = free | hdl = 10536/DRO/DU:30080508 }}</ref>
	Flupentixol's main use is as a long-acting injection given two or three times weekly to individuals with ] who have poor compliance with medication and suffer frequent relapses of illness.
			== Adverse effects ==
	Flupentixol is also used in low doses as an ].<ref name="pmid7291129">{{cite journal | author = Robertson MM, Trimble MR | title = The antidepressant action of flupenthixol | journal = The Practitioner | volume = 225 | issue = 1355 | pages = 761–3 | year = 1981 | month = May | pmid = 7291129 | doi = | url = }}</ref><ref name="pmid6674820">{{cite journal | author = Pöldinger W, Sieberns S | title = Depression-inducing and antidepressive effects of neuroleptics. Experiences with flupenthixol and flupenthixol decanoate | journal = Neuropsychobiology | volume = 10 | issue = 2-3 | pages = 131–6 | year = 1983 | pmid = 6674820 | doi = | url = }}</ref><ref name="pmid369298">{{cite journal | author = Johnson DA | title = A double-blind comparison of flupenthixol, nortriptyline and diazepam in neurotic depression | journal = Acta Psychiatrica Scandinavica | volume = 59 | issue = 1 | pages = 1–8 | year = 1979 | month = January | pmid = 369298 | doi = | url = }}</ref><ref name="pmid773506">{{cite journal | author = Young JP, Hughes WC, Lader MH | title = A controlled comparison of flupenthixol and amitriptyline in depressed outpatients | journal = British Medical Journal | volume = 1 | issue = 6018 | pages = 1116–8 | year = 1976 | month = May | pmid = 773506 | pmc = 1639983 | doi = | url = }}</ref><ref name="pmid961463">{{cite journal | author = Fujiwara J, Ishino H, Baba O, Hanaoka M, Sasaki K | title = Effect of flupenthixol on depression with special reference to combination use with tricyclic antidepressants. An uncontrolled pilot study with 45 patients | journal = Acta Psychiatrica Scandinavica | volume = 54 | issue = 2 | pages = 99–105 | year = 1976 | month = August | pmid = 961463 | doi = | url = }}</ref><ref name="pmid7093597">{{cite journal | author = Tam W, Young JP, John G, Lader MH | title = A controlled comparison of flupenthixol decanoate injections and oral amitriptyline in depressed out-patients | journal = The British Journal of Psychiatry : the Journal of Mental Science | volume = 140 | issue = | pages = 287–91 | year = 1982 | month = March | pmid = 7093597 | doi = | url = }}</ref>
			'''Adverse effect incidence'''<ref name = EMC/><ref name = BNF/><ref name = AMH/><ref>{{cite journal | vauthors = Bostwick JR, Guthrie SK, Ellingrod VL | title = Antipsychotic-induced hyperprolactinemia | journal = Pharmacotherapy | volume = 29 | issue = 1 | pages = 64–73 | date = January 2009 | pmid = 19113797 | doi = 10.1592/phco.29.1.64 | hdl-access = free | s2cid = 25981099 | hdl = 2027.42/90238 }}</ref><ref name = FLUANXOL>{{cite web|title=FLUANXOL® DEPOT FLUANXOL® CONCENTRATED DEPOT|work = TGA eBusiness Services|publisher = Lundbeck Australia Pty Ltd|date=28 June 2013|access-date=20 October 2013|url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-05706-3}}</ref>
			;Common (>1% incidence) adverse effects include:
			* Extrapyramidal side effects such as: (which ''usually'' become apparent soon after therapy is begun or soon after an increase in dose is made)
			** ]
			** ]
			** ]
			** ]
			** Tremor
			** ]
			** ]
			* Dry mouth
			* Constipation
			* Hypersalivation – excessive salivation
			* Blurred vision
			* Diaphoresis – excessive sweating
			* Nausea
			* Dizziness
			* ]
			* Restlessness
			* Insomnia
			* Overactivity
			* Headache
			* Nervousness
			* ]
			* ]
			* ] and its complications such as: (''acutely'')
			** Sexual dysfunction
			** Amenorrhea – cessation of menstrual cycles
			** Gynecomastia – enlargement of breast tissue in males
			** Galactorrhea – the expulsion of breast milk that's not related to breastfeeding or pregnancy
			: and if the hyperprolactinemia persists ''chronically'', the following adverse effects may be seen:
			:* Reduced bone mineral density leading to ] (brittle bones)
			:* Infertility
			* Dyspepsia – indigestion
			* Abdominal pain
			* Flatulence
			* Nasal congestion
			* Polyuria – passing more urine than usual
			;Uncommon (0.1–1% incidence) adverse effects include:
			* Fainting
			* Palpitations
			;Rare (<0.1% incidence) adverse effects include:
			* Blood dyscrasias (abnormalities in the cell composition of blood), such as:
			** ] – a drop in white blood cell counts that leaves one open to potentially life-threatening infections
			** ] – a drop in the number of ] (white blood cells that specifically fight bacteria) in one's blood
			** ] – a less severe drop in white blood cell counts than agranulocytosis
			** ] – a drop in the number of platelets in the blood. Platelets are responsible for blood clotting and hence this leads to an increased risk of bruising and other bleeds
			* ] – a potentially fatal condition that appear to result from central ] blockade. The symptoms include:
			** ]
			** Muscle rigidity
			** ]
			** Autonomic instability (e.g., ], diarrhea, diaphoresis, etc.)
			** Mental status changes (e.g., coma, agitation, anxiety, confusion, etc.)
			;Unknown incidence adverse effects include:
			* Jaundice
			* Abnormal liver function test results
			* ] – an often incurable movement disorder that usually results from years of continuous treatment with antipsychotic drugs, especially ] like flupenthixol. It presents with repetitive, involuntary, purposeless and slow movements; TD can be triggered by a fast dose reduction in any antipsychotic.
			* Hypotension
			* Confusional state
			* Seizures
			* ]
			* ]
			* ]
			* Hot flush
			* Anergia
			* Appetite changes
			* Weight changes
			* Hyperglycemia – high blood glucose (sugar) levels
			* Abnormal glucose tolerance
			* Pruritus – itchiness
			* Rash
			* Dermatitis
			* Photosensitivity – sensitivity to light
			* Oculogyric crisis
			* Accommodation disorder
			* Sleep disorder
			* Impaired concentration
			* Tachycardia
			* ] prolongation – an abnormality in the ] that can lead to potentially fatal changes in heart rhythm (only in ] or <10&nbsp;ms increases in QTc)<ref>{{Cite web|title=Guidelines for the Management of QTc Prolongation in Adults Prescribed Antipsychotics|url=https://www.england.nhs.uk/north/wp-content/uploads/sites/5/2018/12/QTc-flow-diagram-with-medications-final-Dec-17-A3-with-logos.pdf |website=nhs.uk}}</ref><ref>{{cite journal | vauthors = Lambiase PD, de Bono JP, Schilling RJ, Lowe M, Turley A, Slade A, Collinson J, Rajappan K, Harris S, Collison J, Carpenter V, Daw H, Hall A, Roberts E, Holding S, Paisey J, Sopher M, Wright I, Wiles B, Murgatroyd F, Taylor D | display-authors = 6 | title = British Heart Rhythm Society Clinical Practice Guidelines on the Management of Patients Developing QT Prolongation on Antipsychotic Medication | journal = Arrhythmia & Electrophysiology Review | volume = 8 | issue = 3 | pages = 161–165 | date = July 2019 | pmid = 31463053 | pmc = 6702465 | doi = 10.15420/aer.2019.8.3.G1 }}</ref>
			* ]
			* Miosis – constriction of the pupil of the eye
			* Paralytic ] – paralysis of the bowel muscles leading to severe constipation, inability to pass wind, etc.
			* Mydriasis
			* ]
			=== Interactions ===
			It should not be used concomitantly with medications known to prolong the QTc interval (e.g., ]s, ], ], etc.) as this may lead to an increased risk of QTc interval prolongation.<ref name = "
			FLUANXOL"/><ref name = EMC/> Neither should it be given concurrently with ] as it may increase the risk of lithium toxicity and ].<ref name = BNF/><ref name = AMH/><ref name = FLUANXOL/> It should not be given concurrently with other antipsychotics due to the potential for this to increase the risk of side effects, especially neurological side effects such as ].<ref name = BNF/><ref name = AMH/><ref name = FLUANXOL/> It should be avoided in patients on CNS depressants such as opioids, alcohol and barbiturates.<ref name = FLUANXOL/>
			===Contraindications===
			It should not be given in the following disease states:<ref name = EMC/><ref name = BNF/><ref name = AMH/><ref name = FLUANXOL/>
			* ]
			* Prolactin-dependent tumors such as pituitary ]s and ]
			* ]
			* Coma
			* Circulatory collapse
			* Subcortical brain damage
			* ]
			* Parkinson's disease
			* ]
	== Pharmacology ==		== Pharmacology ==
			===Pharmacodynamics===
	Flupentixol acts as an ] at various ] (]-]), ] (]), ] (]), and ] (]) ]s,<ref name="urlPDSP Database - UNC">{{cite web | url = http://pdsp.med.unc.edu/pdsp.php | title = PDSP Database - UNC}}</ref> without affecting the ]s.<ref name="pmid7052344">{{cite journal | author = Golds PR, Przyslo FR, Strange PG | title = The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors | journal = British Journal of Pharmacology | volume = 68 | issue = 3 | pages = 541–9 | year = 1980 | month = March | pmid = 7052344 | pmc = 2044199 | doi = | url = }}</ref>
			'''Binding profile'''<ref>{{cite web|title=PDSP K<sub>i</sub> Database |work=Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth |author1=Roth, BL |author2=Driscol, J |url=http://pdsp.med.unc.edu/pdsp.php |publisher=University of North Carolina at Chapel Hill and the United States National Institute of Mental Health |date=12 January 2011 |access-date=20 October 2013 |url-status=dead |archive-url=https://web.archive.org/web/20131108013656/http://pdsp.med.unc.edu/pdsp.php |archive-date=8 November 2013 }}</ref>
			{| class="wikitable"
	Its antipsychotic effects are likely caused by D<sub>2</sub> and/or 5-HT<sub>2A</sub> antagonism, whereas its antidepressant effects at lower doses may be mediated by preferential D<sub>2</sub>/D<sub>3</sub> ] blockade, resulting in increased postsynaptic activation.
			|-
			! Protein !! ''cis''-flupentixol !! ''trans''-flupentixol
			|-
			| ] || 8028 || —
			|-
			| ] || 87.5 (HFC) || —
			|-
			| ] || 102.2 (RC) || —
			|-
			| ]<ref name="pmid7052344">{{cite journal | vauthors = Golds PR, Przyslo FR, Strange PG | title = The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors | journal = British Journal of Pharmacology | volume = 68 | issue = 3 | pages = 541–549 | date = March 1980 | pmid = 7052344 | pmc = 2044199 | doi = 10.1111/j.1476-5381.1980.tb14570.x }}</ref> || Neg. || Neg.
			|-
			| ] || 3.5 || 474 (MB)
			|-
			| ] || 0.35 || 120
			|-
			| ] || 1.75 || 162.5
			|-
			| ] || 66.3 || >1000
			|-
			| ] || 0.86 || 5.73
			|}
			'''Acronyms used:'''<br />
	== Side effects ==
			HFC – Human frontal cortex receptor<br />
			MB – Mouse brain receptor<br />
			RC – Cloned rat receptor
			A study measuring the ] receptor occupancies of 13 schizophrenic patients treated with 5.7 ± 1.4&nbsp;mg/day of flupentixol found 50-70% receptor occupancy for D2, 20 ± 5% for D1, and 20 ± 10% for 5-HT2A.<ref>{{cite journal | vauthors = Reimold M, Solbach C, Noda S, Schaefer JE, Bartels M, Beneke M, Machulla HJ, Bares R, Glaser T, Wormstall H | display-authors = 6 | title = Occupancy of dopamine D(1), D (2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol | journal = Psychopharmacology | volume = 190 | issue = 2 | pages = 241–249 | date = February 2007 | pmid = 17111172 | doi = 10.1007/s00213-006-0611-0 | s2cid = 2231884 }}</ref>
	The side effects of flupentixol are similar to most other typical antipsychotics, namely ] symptoms of ], ]s, and ] and ] effects like ] and ]. However, it lacks ] adverse effects. But seizures have been reported in some users, and long-term use may even inflict ] on some takers.
			Its antipsychotic effects are predominantly a function of D<sub>2</sub> antagonism.
	== See also ==
	* ]
	* ]
			Its antidepressant effects at lower doses are not well understood; however, it may be mediated by ] and/or preferentially binding to D<sub>2</sub> ]s at low doses, resulting in increased postsynaptic activation via higher dopamine levels. Flupentixol's demonstrated ability to raise dopamine levels in mice<ref>{{cite journal | vauthors = Hyttel J | title = Changes in dopamine synthesis rate in the supersensitivity phase after treatment with a single dose of neuroleptics | journal = Psychopharmacology | volume = 51 | issue = 2 | pages = 205–207 | date = January 1977 | pmid = 14353 | doi = 10.1007/BF00431742 | s2cid = 22801301 }}</ref> and flies<ref>{{cite journal | vauthors = Vickrey TL, Venton BJ | title = Drosophila Dopamine2-like receptors function as autoreceptors | journal = ACS Chemical Neuroscience | volume = 2 | issue = 12 | pages = 723–729 | date = December 2011 | pmid = 22308204 | pmc = 3269839 | doi = 10.1021/cn200057k | author2-link = Jill Venton }}</ref> lends credibility to the supposition of autoreceptor bias. Functional selectivity may be responsible through causing preferential autoreceptor binding or other means. The effective dosage guideline for an antipsychotic is very closely related to its receptor residency time (i.e., where drugs like aripiprazole take several minutes or more to disassociate from a receptor while drugs like quetiapine and clozapine—with guideline dosages in the hundreds of milligrams—take under 30s)<ref>{{cite journal | vauthors = Kapur S, Seeman P | title = Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?: A new hypothesis | journal = The American Journal of Psychiatry | volume = 158 | issue = 3 | pages = 360–369 | date = March 2001 | pmid = 11229973 | doi = 10.1176/appi.ajp.158.3.360 }}</ref><ref>{{cite journal | vauthors = Kapur S, Seeman P | title = Antipsychotic agents differ in how fast they come off the dopamine D2 receptors. Implications for atypical antipsychotic action | journal = Journal of Psychiatry & Neuroscience | volume = 25 | issue = 2 | pages = 161–166 | date = March 2000 | pmid = 10740989 | pmc = 1408069 }}</ref><ref>{{cite journal | vauthors = Carboni L, Negri M, Michielin F, Bertani S, Fratte SD, Oliosi B, Cavanni P | title = Slow dissociation of partial agonists from the D₂ receptor is linked to reduced prolactin release | journal = The International Journal of Neuropsychopharmacology | volume = 15 | issue = 5 | pages = 645–656 | date = June 2012 | pmid = 21733233 | doi = 10.1017/S1461145711000824 | s2cid = 31885144 }}</ref> and long receptor residency time is strongly correlated with likehood of pronounced functional selectivity;<ref>{{cite journal | vauthors = Klein Herenbrink C, Sykes DA, Donthamsetti P, Canals M, Coudrat T, Shonberg J, Scammells PJ, Capuano B, Sexton PM, Charlton SJ, Javitch JA, Christopoulos A, Lane JR | display-authors = 6 | title = The role of kinetic context in apparent biased agonism at GPCRs | journal = Nature Communications | volume = 7 | pages = 10842 | date = February 2016 | pmid = 26905976 | pmc = 4770093 | doi = 10.1038/ncomms10842 | bibcode = 2016NatCo...710842K }}</ref> thus, with a maximum guideline dose of only 18&nbsp;mg/day for schizophrenia, there is a significant possibility of this drug possessing unique signalling characteristics that permit counterintuitive dopaminergic action at low doses.
	== References ==
	{{Reflist|2}}
			===Pharmacokinetics===
			{{Pharmacokinetics of long-acting injectable antipsychotics}}
			==History==
			In March 1963 the Danish pharmaceutical company Lundbeck began research into further agents for schizophrenia, having already developed the thioxanthene derivatives clopenthixol and chlorprothixene. By 1965 the promising agent flupenthixol had been developed and trialled in two hospitals in Vienna by Austrian psychiatrist ].<ref>{{cite journal | vauthors = Gross H, Kaltenbäck E |doi=10.1111/j.1600-0447.1965.tb04969.x|title=Flupenthixol (Fluanxol®), ein Neues Neuroleptikum aus der Thiaxanthenreihe (Klinische Erfahrungen bei Einem Psychiatrischen Krankengut)|year=1965 |journal=Acta Psychiatrica Scandinavica|volume=41|pages=42–56|s2cid=145021607}}</ref> The long- acting decanoate preparation was synthesised in 1967 and introduced into hospital practice in Sweden in 1968, with a reduction in relapses among patients who were put on the depot.<ref>{{cite journal | vauthors = Gottfries CG, Green L | title = Flupenthixol decanoate--in treatment of out-patients | journal = Acta Psychiatrica Scandinavica. Supplementum | volume = 255 | pages = 15–24 | year = 1974 | pmid = 4533707 | doi = 10.1111/j.1600-0447.1974.tb08890.x | s2cid = 42657501 }}</ref>
			== References ==
			{{reflist|30em}}
	{{Antipsychotics}}		{{Antipsychotics}}
	{{Antidepressants}}		{{Antidepressants}}
	{{Anxiolytics}}		{{Anxiolytics}}
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	{{Adrenergics}}
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	{{Dopaminergics}}
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	{{Histaminergics}}
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	{{Serotonergics}}
			{{Adrenergic receptor modulators}}
	{{Piperazines}}
			{{Dopamine receptor modulators}}
			{{Histamine receptor modulators}}
			{{Serotonin receptor modulators}}
			}}
	{{Tricyclics}}		{{Tricyclics}}
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