Editing Prochlorperazine

{{Short description|Medication for nausea, psychosis, and anxiety}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 464214968
| image = Prochlorperazine.svg
| image_class = skin-invert-image
| width = 250

<!--Clinical data-->
| tradename =  Compazine, Stemetil, others
| Drugs.com = {{drugs.com|monograph|prochlorperazine}}
| MedlinePlus = a682116
| DailyMedID = Prochlorperazine
| pregnancy_AU = C
| pregnancy_category = 
| legal_AU = S4
| legal_AU_comment = /&nbsp;S3
| 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=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US = Rx-only
| legal_UK = POM
| legal_UK_comment = /&nbsp;P<ref>{{cite web | title=Prochlorperazine 3 mg Buccal Tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=9 December 2019 | url=https://www.medicines.org.uk/emc/product/5227/smpc | access-date=30 December 2022}}</ref><ref>{{cite web | title=Buccastem M Buccal Tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=9 December 2019 | url=https://www.medicines.org.uk/emc/product/478/smpc | access-date=30 December 2022}}</ref>
| routes_of_administration = [[Oral administration]], [[rectal administration]], [[intramuscular injection]], [[intravenous injection]] (IV)
| class = [[Typical antipsychotic]]

<!--Pharmacokinetic data-->
| bioavailability = Unknown, but presumed substantial
| protein_bound = 91–99%
| metabolism = Mainly [[Liver]] ([[CYP2D6]] and/or [[CYP3A4]])
| elimination_half-life = 4–8 hours, differs with the method of administration
| excretion = [[Bile duct]], (colored) inactive metabolites in urine

<!--Identifiers-->
| IUPHAR_ligand = 7279
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 58-38-8
| ATC_prefix = N05
| ATC_suffix = AB04
| PubChem = 4917
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00433
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4748
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YHP6YLT61T
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00493
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8435
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 728

<!--Chemical data-->
| IUPAC_name = 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-10''H''-phenothiazine
| C=20 | H=24 | Cl=1 | N=3 | S=1
| SMILES = Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(C)CC4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WIKYUJGCLQQFNW-UHFFFAOYSA-N
}}

<!-- Definition and medical uses -->
'''Prochlorperazine''', formerly<ref>{{cite web |url=https://www.rxlist.com/compazine-side-effects-drug-center.htm |website=RX List |access-date=14 April 2021|title=Side Effects of Compazine (Prochlorperazine), Warnings, Uses }}</ref> sold under the brand name '''Compazine''' among others, is a medication used to treat [[nausea]], [[migraines]], [[schizophrenia]], [[psychosis]] and [[anxiety]].<ref name=AHFS2019/><ref name=BNF76>{{cite book|title=British national formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=385–386|edition=76}}</ref><ref name=AHS2016>{{cite journal | vauthors = Orr SL, Friedman BW, Christie S, Minen MT, Bamford C, Kelley NE, Tepper D | title = Management of Adults With Acute Migraine in the Emergency Department: The American Headache Society Evidence Assessment of Parenteral Pharmacotherapies | journal = Headache | volume = 56 | issue = 6 | pages = 911–940 | date = June 2016 | pmid = 27300483 | doi = 10.1111/head.12835 | doi-access = free }}</ref><ref name="pmid30725768">{{cite book | vauthors = Din L, Preuss CV | chapter = Prochlorperazine | date = March 2022 | title = StatPearls [Internet] | location = Treasure Island (FL) | publisher = StatPearls Publishing | pmid = 30725768 | chapter-url = https://www.ncbi.nlm.nih.gov/books/NBK537083/ }}</ref> It is a less preferred medication for anxiety.<ref name=AHFS2019/> It may be taken [[by mouth]], [[rectal administration|rectally]], [[intravenous|injection into a vein]], or [[intramuscular|injection into a muscle]].<ref name=AHFS2019/>

<!-- Side effects and mechanisms -->
Common side effects include sleepiness, blurry vision, [[Hypotension|low blood pressure]], and dizziness.<ref name=AHFS2019/> Serious side effects may include movement disorders including [[tardive dyskinesia]] and [[neuroleptic malignant syndrome]].<ref name=AHFS2019/> Use in [[pregnancy]] and [[breastfeeding]] is generally not recommended.<ref name=Preg2019>{{cite web |title=Prochlorperazine Use During Pregnancy |url=https://www.drugs.com/pregnancy/prochlorperazine.html |website=Drugs.com |access-date=3 March 2019 }}</ref> It is a [[typical antipsychotic]] which is believed to work by reducing the action of [[dopamine]] in the brain.<ref name=AHFS2019>{{cite web |title=Prochlorperazine Monograph for Professionals |url=https://www.drugs.com/monograph/prochlorperazine.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 }}</ref>

<!-- History and culture -->
Prochlorperazine was approved for medical use in the United States in 1956.<ref name=AHFS2019/> It is available as a [[generic medication]].<ref name=BNF76/> In 2020, it was the 355th most commonly prescribed medication in the United States, with more than 600{{nbsp}}thousand prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Prochlorperazine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Prochlorperazine | access-date = 7 October 2022}}</ref>

== Medical uses ==
===Vomiting===
Prochlorperazine is used to [[antiemetic|prevent vomiting]] caused by [[chemotherapy]], [[radiation therapy]] and [[Postoperative nausea and vomiting|in the pre- and postoperative setting]].<ref name=Lin2016>{{cite journal | vauthors = Lau Moon Lin M, Robinson PD, Flank J, Sung L, Dupuis LL | title = The Safety of Prochlorperazine in Children: A Systematic Review and Meta-Analysis | journal = Drug Safety | volume = 39 | issue = 6 | pages = 509–516 | date = June 2016 | pmid = 26884326 | doi = 10.1007/s40264-016-0398-9 | s2cid = 39349233 }}</ref> A 2015 Cochrane review found no differences in efficacy among drugs commonly used for this purpose in emergency rooms.<ref>{{cite journal | vauthors = Furyk JS, Meek RA, Egerton-Warburton D | title = Drugs for the treatment of nausea and vomiting in adults in the emergency department setting | journal = The Cochrane Database of Systematic Reviews | issue = 9 | pages = CD010106 | date = September 2015 | volume = 2018 | pmid = 26411330 | pmc = 6517141 | doi = 10.1002/14651858.CD010106.pub2 }}</ref>

===Migraine===
Prochlorperazine, generally by intravenous, is used to treat [[migraine]].<ref name="somestats">{{cite journal | vauthors = Golikhatir I, Cheraghmakani H, Bozorgi F, Jahanian F, Sazgar M, Montazer SH | title = The Efficacy and Safety of Prochlorperazine in Patients With Acute Migraine: A Systematic Review and Meta-Analysis | journal = Headache | volume = 59 | issue = 5 | pages = 682–700 | date = May 2019 | pmid = 30990883 | doi = 10.1111/head.13527 | s2cid = 119544256 }}</ref><ref>{{cite journal | vauthors = Patniyot IR, Gelfand AA | title = Acute Treatment Therapies for Pediatric Migraine: A Qualitative Systematic Review | journal = Headache | volume = 56 | issue = 1 | pages = 49–70 | date = January 2016 | pmid = 26790849 | doi = 10.1111/head.12746 | s2cid = 25893066 }}</ref> Such use is recommended by The American Headache Society.<ref name=AHS2016/> A 2019 systematic review found prochlorperazine was nearly three times more likely than [[metoclopramide]] to relieve headache within 60 minutes of administration.<ref name="somestats"/>

===Labyrinthitis===
In the UK prochlorperazine maleate has been used for [[labyrinthitis]], which includes nausea and [[vertigo]].<ref>{{cite journal | vauthors = Coatesworth AP | title = Assessment and treatment of dizziness | journal = Journal of Neurology, Neurosurgery, and Psychiatry | volume = 69 | issue = 5 | pages = 706–707 | date = November 2000 | pmid = 11184241 | pmc = 1763384 | doi = 10.1136/jnnp.69.5.706 }}</ref>

== Side effects ==
Sedation is very common, and [[Extrapyramidal symptoms|extrapyramidal side effects]] are common and include restlessness, [[dystonic]] reactions, [[pseudoparkinsonism]], and [[akathisia]]; the extrapyramidal symptoms can affect 2% of people at low doses, whereas higher doses may affect as many as 40% of people.<ref name=Brown1998>{{cite book | vauthors = Brown TM, Stoudemire A | title = Psychiatric Side Effects of Prescription and Over-The-Counter Medications | chapter = Antipsychotics | publisher = American Psychiatric Publishing | year = 1998 | pages = 1946 | chapter-url = https://books.google.com/books?id=K7kevbILCuQC&pg=PA1946| isbn = 9780880488686 }}</ref><ref>{{cite web|url=https://www.drugs.com/sfx/procot-side-effects.html|title=Procot Side Effects in Detail|website=Drugs.com}}</ref>

Prochlorperazine can also cause a life-threatening condition called [[neuroleptic malignant syndrome]] (NMS). Some symptoms of NMS include high fever, stiff muscles, neck muscle spasms, confusion, irregular pulse or blood pressure, fast heart rate (tachycardia), sweating, and abnormal heart rhythms (arrhythmias). Research from the Veterans Administration and the United States [[Food and Drug Administration]] show injection site reactions. Adverse effects are similar in children.<ref name=Lin2016/>

=== Warning ===
The FDA-approved label for prochlorperazine includes a warning for increased risk of mortality in elderly patients with dementia-related psychosis.<ref>{{Cite web|title=Prochlorperazine Maleate Tablets, USP|url=https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=2fd7803f-fb1f-4f00-86ad-c2436b569e6d&type=display#:~:text=WARNINGS-,Increased%20Mortality%20in%20Elderly%20Patients%20with%20Dementia-Related%20Psychosis,psychosis%20(see%20BOXED%20WARNING).|access-date=2022-02-02|website=dailymed.nlm.nih.gov}}</ref> 

===Discontinuation===
The [[British National Formulary]] recommends a gradual withdrawal when [[discontinuing antipsychotics]] to avoid acute withdrawal syndrome or rapid relapse.<ref name="Group 2009 192">{{cite book |editor1-first=BMJ | editor =  Joint Formulary Committee  | title = British National Formulary | edition = 57 | date = March 2009 |publisher=Royal Pharmaceutical Society of Great Britain |location=United Kingdom |isbn=978-0-85369-845-6 |page=192 |chapter=4.2.1 |quote=Withdrawal of antipsychotic drugs after long-term therapy should always be gradual and closely monitored to avoid the risk of acute withdrawal syndromes or rapid relapse.}}</ref> Symptoms of withdrawal commonly include nausea, vomiting, and loss of appetite.<ref name=Had2004>{{cite book | vauthors = Haddad P, Haddad PM, Dursun S, Deakin B |title=Adverse Syndromes and Psychiatric Drugs: A Clinical Guide |date=2004 |publisher=OUP Oxford |isbn=9780198527480 |pages=207–216 |url=https://books.google.com/books?id=CWR7DwAAQBAJ&pg=PA207 }}</ref> Other symptoms may include restlessness, increased sweating, and trouble sleeping.<ref name=Had2004/> Less commonly there may be a feeling of the world spinning, numbness, or muscle pains.<ref name=Had2004/> Symptoms generally resolve after a short period of time.<ref name=Had2004/>

There is tentative evidence that discontinuation of antipsychotics can result in psychosis.<ref>{{cite journal | vauthors = Moncrieff J | title = Does antipsychotic withdrawal provoke psychosis? Review of the literature on rapid onset psychosis (supersensitivity psychosis) and withdrawal-related relapse | journal = Acta Psychiatrica Scandinavica | volume = 114 | issue = 1 | pages = 3–13 | date = July 2006 | pmid = 16774655 | doi = 10.1111/j.1600-0447.2006.00787.x | s2cid = 6267180 }}</ref> It may also result in reoccurrence of the condition that is being treated.<ref>{{cite book | vauthors = Sacchetti E, Vita A, Siracusano A, Fleischhacker W |title=Adherence to Antipsychotics in Sc |date=2013 |publisher=Springer Science & Business Media |isbn=9788847026797 |page=85 |url=https://books.google.com/books?id=odE-AgAAQBAJ&pg=PA85 }}</ref> Rarely tardive dyskinesia can occur when the medication is stopped.<ref name=Had2004/>

== Pharmacology ==
{| class="wikitable" style = "float: right; margin-left:15px; text-align:center"
|+Prochlorperazine
!Site
![[Ligand (biochemistry)#binding affinity|Ki]] (nM)
!Species
!Ref
|-
|[[5-HT1A receptor|5-HT<sub>1A</sub>]]
|5,888
|Human
|<ref name=":0">{{cite journal | vauthors = Silvestre JS, Prous J | title = Research on adverse drug events. I. Muscarinic M3 receptor binding affinity could predict the risk of antipsychotics to induce type 2 diabetes | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 27 | issue = 5 | pages = 289–304 | date = June 2005 | pmid = 16082416 | doi = 10.1358/mf.2005.27.5.908643 }}</ref>
|-
|[[5-HT2A receptor|5-HT<sub>2A</sub>]]
|7.24
|Human
|<ref name=":0" />
|-
|[[5-HT2C receptor|5-HT<sub>2C</sub>]]
|123
|Human
|<ref name=":0" />
|-
|[[5-HT3 receptor|5-HT<sub>3</sub>]]
|1349
|Human
|<ref name=":0" />
|-
|[[5-HT6 receptor|5-HT<sub>6</sub>]]
|148
|Human
|<ref name=":0" />
|-
|[[5-HT7 receptor|5-HT<sub>7</sub>]]
|6,760
|Human
|<ref name=":0" />
|-
|[[Alpha-1 adrenergic receptor|α<sub>1</sub>]]
|24
|Human
|<ref name=":1">{{cite journal | vauthors = Richelson E, Nelson A | title = Antagonism by neuroleptics of neurotransmitter receptors of normal human brain in vitro | journal = European Journal of Pharmacology | volume = 103 | issue = 3–4 | pages = 197–204 | date = August 1984 | pmid = 6149136 | doi = 10.1016/0014-2999(84)90478-3 }}</ref>
|-
|[[Alpha-2 adrenergic receptor|α<sub>2</sub>]]
|1700
|Human
|<ref name=":1" />
|-
|[[Muscarinic acetylcholine receptor M1|M<sub>1</sub>]]
|776
|Human
|<ref name=":0" />
|-
|[[Muscarinic acetylcholine receptor M2|M<sub>2</sub>]]
|1413
|Human
|<ref name=":0" />
|-
|[[Dopamine receptor D1|D<sub>1</sub>]]
|251
|Human
|<ref name=":0" />
|-
|[[Dopamine receptor D2|D<sub>2</sub>]]
|2.24
|Human
|<ref name=":0" />
|-
|[[Dopamine receptor D3|D<sub>3</sub>]]
|1.82
|Human
|<ref name=":0" />
|-
|[[Dopamine receptor D4|D<sub>4</sub>]]
|5.37
|Human
|<ref name=":0" />
|-
|[[Histamine H1 receptor|H<sub>1</sub>]]
|6.03
|Human
|<ref name=":2">{{cite journal | vauthors = Appl H, Holzammer T, Dove S, Haen E, Strasser A, Seifert R | title = Interactions of recombinant human histamine H<sub>1</sub>R, H<sub>2</sub>R, H<sub>3</sub>R, and H<sub>4</sub>R receptors with 34 antidepressants and antipsychotics | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 385 | issue = 2 | pages = 145–170 | date = February 2012 | pmid = 22033803 | doi = 10.1007/s00210-011-0704-0 | s2cid = 14274150 }}</ref>
|-
|[[Histamine H3 receptor|H<sub>3</sub>]]
|17,378
|Human
|<ref name=":2" />
|-
|[[Histamine H4 receptor|H<sub>4</sub>]]
|17783
|Human
|<ref name=":2" />
|-
|[[Dopamine transporter|DAT]]
|589
|Human
|<ref name=":0" />
|-
|[[Norepinephrine transporter|NET]]
|600
|Rat
|<ref>{{cite journal | vauthors = Richelson E, Pfenning M | title = Blockade by antidepressants and related compounds of biogenic amine uptake into rat brain synaptosomes: most antidepressants selectively block norepinephrine uptake | journal = European Journal of Pharmacology | volume = 104 | issue = 3–4 | pages = 277–286 | date = September 1984 | pmid = 6499924 | doi = 10.1016/0014-2999(84)90403-5 }}</ref>
|}

Prochlorperazine is thought to exert its [[antipsychotic]] effects by blocking [[dopamine receptor]]s.<ref>{{cite book | vauthors = Ebadi MS | title = Desk Reference of Clinical Pharmacology | date = 2007 }}</ref>

Prochlorperazine is analogous to [[chlorpromazine]]; both of these agents antagonize dopaminergic [[dopamine receptor D2|D<sub>2</sub> receptor]]s in various pathways of the [[central nervous system]]. This D<sub>2</sub> blockade results in antipsychotic, [[antiemetic]] and other effects. [[Hyperprolactinemia]] is a side effect of [[dopamine antagonist]]s as blockade of D<sub>2</sub> receptors within the [[tuberoinfundibular pathway]] results in increased plasma levels of [[prolactin]] due to increased secretion by lactotrophs in the anterior pituitary.

Following intramuscular injection, the antiemetic action is evident within 5 to 10 minutes and lasts for three to four hours. Rapid action is also noted after buccal treatment. With oral dosing, the start of action is delayed but the duration is somewhat longer (approximately six hours).

==Society and culture==
In the United Kingdom, prochlorperazine is available for the treatment of nausea caused by migraine as a [[Buccal administration|tablet dissolved in the mouth]], and in Australia as a tablet swallowed whole. In the UK, it is available via a prescription and as a [[pharmacy medicine]], meaning it does not require a prescription but is only available after talking with a [[pharmacist]].<ref>{{cite web|title=Buccastem M - Summary of Product Characteristics (SPC) - (eMC)|url=https://www.medicines.org.uk/emc/medicine/22797|publisher=UK Electronic Medicines Compendium|access-date=19 September 2017|date=16 February 2016}}</ref><ref>{{cite web|title=Medicines information|url=http://www.nhs.uk/conditions/Medicinesinfo/Pages/Introduction.aspx|publisher=NHS Choices|access-date=19 September 2017|archive-date=22 October 2017|archive-url=https://web.archive.org/web/20171022015130/https://www.nhs.uk/conditions/medicinesinfo/pages/introduction.aspx|url-status=dead}}</ref>

===Marketing===
Prochlorperazine is available as tablets, suppositories, and in an injectable form.<ref name=brands/>

As of September 2017 it was marketed under the trade names Ametil, Antinaus, Buccastem, Bukatel, Chlormeprazine, Chloropernazine, Compazine, Compro, Daolin, Dhaperazine, Emedrotec, Emetiral, Eminorm, Lotamin, Mitil, Mormal, Nautisol, Novamin, Novomit, Proazine, Procalm, Prochlorperazin, Prochlorperazine, Prochlorpérazine, Prochlorperazinum, Prochlozine, Proclorperazina, Promat, Promin, Promtil, Roumin, Scripto-metic, Seratil, Stemetil, Steremal, Vergon, Vestil, and Volimin.<ref name=brands>{{cite web|title=Prochlorperazine international brands|url=https://www.drugs.com/international/prochlorperazine.html|publisher=Drugs.com|access-date=19 September 2017}}</ref><ref>{{cite web|url=https://www.rxlist.com/compazine-drug/patient-images-side-effects.htm|title=Compazine (Prochlorperazine) Patient Information: Side Effects and Drug Images at RxList|website=RxList}}</ref>

===Historical Formulations===
Prochlorperazine was combined with [[paracetamol]] and marketed{{When?|date=April 2025}} for humans as the [[combination drug]] Vestil-A; it was combined with [[isopropamide]] (brand name Darbazine) as a combination drug for veterinary use.<ref name=brands/> 

Until 1981, a combination [[anorectic|diet pill]] composed of prochlorperazine and [[dextroamphetamine]] was marketed as [[Eskatrol]] in the [[United States]] by [[Smith, Kline & French]] Laboratories.

==Research==
Alexza Pharmaceuticals studied an inhaled form of prochlorperazine for the treatment of migraine through Phase II trials under the development name AT-001; development was discontinued in 2011.<ref>{{cite journal | vauthors = Chua AL, Silberstein S | title = Inhaled drug therapy development for the treatment of migraine | journal = Expert Opinion on Pharmacotherapy | volume = 17 | issue = 13 | pages = 1733–1743 | date = September 2016 | pmid = 27416108 | doi = 10.1080/14656566.2016.1203901 | s2cid = 11724776 }}</ref>
==Synthesis==
[[File:Prochlorperazine synthesis.svg|class=skin-invert-image|thumb|center|500px|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0197 Thieme] Synthesis:<ref>J. Gen. Chem. USSR (Engl. Transl.), vol. 32, p. 1915 - 1919,1892 – 1895.</ref> Patent:<ref>GB780193 idem Horclois Raymond Jacques, {{US patent|2902484}} (1959 to Rhone Poulenc Sa).</ref>]]
The alkylation of 2-chlorophenothiazine ('''1''') and 1-(3-Chloropropyl)-4-methylpiperazine [104-16-5] ('''2''') in the presence of sodamide gives Prochlorperazine ('''3'''); or by alkylation of 2-Chloro-10-(3-chloropropyl)phenothiazine [2765-59-5] ('''4''') and 1-methylpiperazine ('''5''').

== References ==
{{Reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/prochlorperazine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Prochlorperazine }}

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