Editing Haloperidol (section)

{{Short description|Typical antipsychotic medication}}
{{Use American English|date=November 2017}}
{{Use dmy dates|date=November 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 464369120
| image = Haloperidol.svg
| image_class = skin-invert-image
| width = 200
| alt = 
| image2 = Haloperidol-from-xtal-3D-balls.png
| width2 = 200
| alt2 = 

<!-- Clinical data -->
| pronounce = {{IPAc-en|ˌ|h|æ|l|oʊ|ˈ|p|ɛ|r|ɪ|d|ɒ|l}}
| tradename = Haldol, others
| Drugs.com = {{drugs.com|monograph|haloperidol}}
| MedlinePlus = a682180
| DailyMedID = Haloperidol
| pregnancy_AU = C
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Haloperidol Use During Pregnancy | website=Drugs.com | date=10 February 2020 | url=https://www.drugs.com/pregnancy/haloperidol.html | access-date=13 September 2020}}</ref>
| routes_of_administration = [[Oral administration|By mouth]], [[Intramuscular injection|intramuscular]], [[Intravenous therapy|intravenous]], [[Depot injection|depot]] (as [[decanoate]] [[ester]])
| class = [[Typical antipsychotic]]
| ATC_prefix = N05
| ATC_suffix = AD01

| legal_AU = S4
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |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=3 August 2023 |access-date=16 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA = Rx-only
| legal_UK = POM
| legal_US = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = 60–70% (by mouth)<ref name = PK1999 />
| protein_bound = ~90%<ref name = PK1999 />
| metabolism = Liver-mediated<ref name = PK1999 />
| metabolites = • [[HPP+|HPP<sup>+</sup>]]<ref name="Kostrzewa2022" /><ref name="Igarashi1998" /><ref name="GórskaMarszałłSloderbach2015" />
| elimination_half-life = 14–26 hours (IV), 20.7 hours (IM), 14–37 hours (oral)<ref name=PK1999/>
| excretion = [[Bile duct|Biliary]] (hence in feces) and in urine<ref name = PK1999 /><ref name=TGA>{{cite web |title = Product Information Serenace |work = TGA eBusiness Services |publisher = Aspen Pharma Pty Ltd |date = 29 September 2011 |access-date = 29 May 2014 |url = https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2011-PI-03532-3 |format = PDF |url-status = live |archive-url = https://web.archive.org/web/20170314204106/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2011-PI-03532-3 |archive-date = 14 March 2017 }}</ref>

<!--Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 52-86-8
| PubChem = 3559
| IUPHAR_ligand = 86
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00502
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3438
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J6292F8L3D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00136
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 5613
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 54

<!-- Chemical data -->
| IUPAC_name = 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
| C=21 | H=23 | Cl=1 | F=1 | N=1 | O=2
| smiles = c1cc(ccc1C(=O)CCCN2CCC(CC2)(c3ccc(cc3)Cl)O)F
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LNEPOXFFQSENCJ-UHFFFAOYSA-N
}}

<!-- Definition and uses -->
'''Haloperidol''', sold under the brand name '''Haldol''' among others, is a [[typical antipsychotic]] medication.<ref name=AHFS2015 /> Haloperidol is used in the treatment of [[schizophrenia]], [[Tic|tics]] in [[Tourette syndrome]], [[mania]] in [[bipolar disorder]], [[delirium]], agitation, acute [[psychosis]], and [[hallucinations]] from [[alcohol withdrawal]].<ref name=AHFS2015 /><ref name= NEJM2014>{{cite journal | vauthors = Schuckit MA | title = Recognition and management of withdrawal delirium (delirium tremens) | journal = The New England Journal of Medicine | volume = 371 | issue = 22 | pages = 2109–2113 | date = November 2014 | pmid = 25427113 | doi =  10.1056/NEJMra1407298 | s2cid = 205116954 | url = https://escholarship.org/uc/item/08b9z9th }}</ref><ref>{{cite journal | vauthors = Plosker GL | title = Quetiapine: a pharmacoeconomic review of its use in bipolar disorder | journal = PharmacoEconomics | volume = 30 | issue = 7 | pages = 611–631 | date = July 2012 | pmid = 22559293 | doi = 10.2165/11208500-000000000-00000 }}</ref> It may be used by mouth or injection into a [[intramuscular injection|muscle]] or a [[intravenous|vein]].<ref name=AHFS2015 /> Haloperidol typically works within 30 to 60 minutes.<ref name=AHFS2015 /> A long-acting formulation may be used as an injection every four weeks for people with schizophrenia or related illnesses, who either forget or refuse to take the medication by mouth.<ref name= AHFS2015 />

<!-- Side effects -->
Haloperidol may result in movement disorders such as [[tardive dyskinesia]], and [[akathisia]], both of which may be permanent.<ref name=AHFS2015 /> [[Neuroleptic malignant syndrome]] and [[Drug-induced QT prolongation|QT interval prolongation]] may occur, the latter particularly with IV administration.<ref name=AHFS2015 /> In older people with psychosis due to [[dementia]] it results in an increased risk of death.<ref name= AHFS2015>{{cite web |title = Haloperidol |url = https://www.drugs.com/monograph/haloperidol.html |publisher = The American Society of Health-System Pharmacists |access-date = 2 January 2015 |url-status = live |archive-url = https://web.archive.org/web/20150102120426/http://www.drugs.com/monograph/haloperidol.html |archive-date = 2 January 2015 }}</ref> When taken during pregnancy it may result in problems in the infant.<ref name=AHFS2015 /><ref name=TGA2015>{{cite web |title = Prescribing medicines in pregnancy database |url = http://www.tga.gov.au/hp/medicines-pregnancy.htm |work = Australian Government |access-date = 2 January 2015 |date = 3 March 2014 |url-status = live |archive-url = https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm |archive-date = 8 April 2014 }}</ref> It should not be used by people with [[Parkinson's disease]].<ref name=AHFS2015 />

<!-- History, society and culture -->
Haloperidol was discovered in 1958 by the team of [[Paul Janssen]],<ref>{{cite book | vauthors = Sneader W |title = Drug discovery : a history |date = 2005 |publisher = Wiley |location = Chichester |isbn = 978-0-471-89979-2 |page = 124 |edition = Rev. and updated |url = https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA124 |url-status = live |archive-url = https://web.archive.org/web/20151208072014/https://books.google.ca/books?id=Cb6BOkj9fK4C&pg=PA124 |archive-date = 8 December 2015 }}</ref> prepared as part of a [[structure-activity relationship]] investigation into analogs of [[pethidine]] (meperidine).<ref>{{cite book | vauthors = Ravina E |title = The evolution of drug discovery: from traditional medicines to modern drugs |date = 2011 |publisher = Wiley-VCH |location = Weinheim |isbn = 978-3-527-32669-3 |page = 62 |edition = 1. Aufl. |url = https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA62 |url-status = live |archive-url = https://web.archive.org/web/20151208071857/https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA62 |archive-date = 8 December 2015 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> It is the most commonly used typical antipsychotic.<ref name=Ste2004>{{cite book | vauthors = Stevens A |title = Health care needs assessment: the epidemiologically based needs assessment reviews |date = 2004 |publisher = Radcliffe Medical |location = Abingdon |isbn = 978-1-85775-892-4 |page = 202 |edition = 2nd |url = https://books.google.com/books?id=HCLIeMG9WgoC&pg=PA202 |url-status = live |archive-url = https://web.archive.org/web/20151208072515/https://books.google.ca/books?id=HCLIeMG9WgoC&pg=PA202 |archive-date = 8 December 2015 }}</ref> In 2020, it was the 303rd most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title = Haloperidol - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Haloperidol | access-date = 7 October 2022}}</ref>