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Propranolol
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{{Short description|Beta blocker drug}} {{Distinguish|Propanol|Propofol}} {{Use dmy dates|date=February 2024}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Watchedfields = changed | verifiedrevid = 464216937 | image = Propranolol.svg | image_class = skin-invert-image | width = 250 | alt = | caption = | image2 = Propranolol-from-1977-crystal-structure-3D-balls-side.png | width2 = 250 | alt2 = | chirality = [[Racemic mixture]] <!--Clinical data-->| pronounce = {{IPAc-en|p|r|oΚ|Λ|p|r|Γ¦|n|Ι|Λ|l|Ι|l}} | tradename = Inderal, others | Drugs.com = {{drugs.com|monograph|propranolol-hydrochloride}} | DailyMedID = Propranolol | MedlinePlus = | pregnancy_AU = C | pregnancy_category = | routes_of_administration = [[Oral administration|By mouth]], [[rectal administration|rectal]], [[intravenous therapy|intravenous]] | ATC_prefix = C07 | ATC_suffix = AA05 | legal_AU = S4 | legal_UK = POM | legal_US = Rx-only | legal_EU = Rx-only | legal_CA = Rx-only | legal_status = <!--Pharmacokinetic data--> | bioavailability = 26% | protein_bound = 90% | metabolism = [[Liver]] (extensive) [[CYP1A2]], [[CYP2D6]]; minor: [[CYP2C19]], [[CYP3A4]] | metabolites = N-desisopropylpropranolol, 4'-hydroxypropanolol | elimination_half-life = 4β5 hours | excretion = [[Kidney]] (<1%) <!--Identifiers-->| class = [[Beta blocker]] | index2_label = as HCl | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 525-66-6 | PubChem = 4946 | IUPHAR_ligand = 564 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00571 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4777 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9Y8NXQ24VQ | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D08443 | KEGG2_Ref = {{keggcite|correct|kegg}} | KEGG2 = D00483 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 8499 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 27 <!--Chemical data-->| IUPAC_name = (''RS'')-1-(propan-2-ylamino)-3-(1-naphthyloxy)propan-2-ol | C = 16 | H = 21 | N = 1 | O = 2 | SMILES = OC(COC1=C2C=CC=CC2=CC=C1)CNC(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = AQHHHDLHHXJYJD-UHFFFAOYSA-N | melting_point = 96 }} <!-- Definition and medical uses --> '''Propranolol''' is a medication of the [[beta blocker]] class.<ref name="AHFS2015" /> It is used to treat [[hypertension|high blood pressure]], some types of [[cardiac dysrhythmia|irregular heart rate]], [[thyrotoxicosis]], [[capillary hemangioma]]s, [[akathisia]], [[performance anxiety]], and [[essential tremor]]s,<ref name="AHFS2015" /><ref name="Dav2006">{{cite journal | vauthors = Davidson JR | title = Pharmacotherapy of social anxiety disorder: what does the evidence tell us? | journal = The Journal of Clinical Psychiatry | volume = 67 | issue = Suppl 12 | pages = 20β26 | date = 2006 | pmid = 17092192 | doi = 10.1016/j.genhosppsych.2005.07.002 }}</ref><ref name="Chinnadurai2016">{{cite journal | vauthors = Chinnadurai S, Fonnesbeck C, Snyder KM, Sathe NA, Morad A, Likis FE, McPheeters ML | title = Pharmacologic Interventions for Infantile Hemangioma: A Meta-analysis | journal = Pediatrics | volume = 137 | issue = 2 | pages = e20153896 | date = February 2016 | pmid = 26772662 | doi = 10.1542/peds.2015-3896 | s2cid = 30459652 | url = http://pediatrics.aappublications.org/content/pediatrics/137/2/e20153896.full.pdf | doi-access = free }}</ref><ref>{{Cite journal |last=Blaisdell |first=G. D. |date=July 1994 |title=Akathisia: A Comprehensive Review and Treatment Summary |url=https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-2007-1014294 |journal=Pharmacopsychiatry |language=en |volume=27 |issue=4 |pages=139β146 |doi=10.1055/s-2007-1014294 |pmid=7972345 |issn=0176-3679|url-access=subscription }}</ref> as well to prevent [[migraine headaches]], and to prevent further heart problems in those with [[angina]] or previous [[myocardial infarction|heart attacks]].<ref name="AHFS2015">{{cite web | title = Propranolol hydrochloride | work = Monograph | url = https://www.drugs.com/monograph/propranolol-hydrochloride.html | publisher = The American Society of Health-System Pharmacists | access-date = 1 January 2015 | url-status = live | archive-url = https://web.archive.org/web/20150101152631/http://www.drugs.com/monograph/propranolol-hydrochloride.html | archive-date = 1 January 2015 | df = dmy-all }}</ref> It can be taken [[oral administration|orally]] or by [[intravenous injection]].<ref name="AHFS2015" /> The formulation that is taken orally comes in short-acting and long-acting versions.<ref name="AHFS2015" /> Propranolol appears in the blood after 30 minutes and has a maximum effect between 60 and 90 minutes when taken orally.<ref name="AHFS2015" /><ref>{{cite book| vauthors = Bryson PD |title=Comprehensive review in toxicology for emergency clinicians|date=1997|publisher=Taylor & Francis|location=Washington, DC|isbn=9781560326120|page=167|edition=3|url=https://books.google.com/books?id=f7009NkJv70C&pg=PA167|url-status=live|archive-url=https://web.archive.org/web/20170324020627/https://books.google.com/books?id=f7009NkJv70C&pg=PA167|archive-date=24 March 2017}}</ref> <!-- Side effects and mechanism--> Common [[side effect]]s include [[nausea]], [[abdominal pain]], and [[constipation]].<ref name=AHFS2015/> It may worsen the symptoms of [[asthma]].<ref name=AHFS2015/> Propranolol may cause [[teratogen|harmful effect]]s for the baby if taken during [[pregnancy]];<ref>{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm|work=Australian Government|access-date=22 April 2014|date=3 March 2014|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|archive-date=8 April 2014}}</ref> however, its use during [[breastfeeding]] is generally considered to be safe.<ref>{{cite book| vauthors = Briggs GG, Freeman RK, Yaffe SJ |title=Drugs in pregnancy and lactation: a reference guide to fetal and neonatal risk|date=2011|publisher=Wolters Kluwer Health/Lippincott Williams & Wilkins |location=Philadelphia |isbn=9781608317080 |page=1226|edition=9th|url=https://books.google.com/books?id=OIgTE4aynrMC&pg=PA1226|url-status=live|archive-url=https://web.archive.org/web/20170214212837/https://books.google.ca/books?id=OIgTE4aynrMC&pg=PA1226|archive-date=14 February 2017}}</ref> It is a non-selective beta blocker which works by blocking [[Ξ²-adrenergic receptors]].<ref name=AHFS2015/> <!-- History, society and culture --> Propranolol was patented in 1962 and approved for medical use in 1964.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=460 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA460 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO }}</ref> Propranolol is available as a [[generic medication]].<ref name=AHFS2015/> In 2022, it was the 77th most commonly prescribed medication in the United States, with more than 8{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Propranolol Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Propranolol | access-date = 30 August 2024 }}</ref>
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