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Line 5: \| Watchedfields = changed \| verifiedrevid = 456349142 \| image = ~~Paracetamol~~N-~~skeletal~~Acetyl-p-aminophenol.svg \| width = 210 \| alt = \| caption = \| ~~image2~~width2 = ~~Paracetamol-from-xtal-3D-balls.png~~ \| ~~width2~~alt2 = \| ~~alt2~~imageL = =Paracetamol-from-xtal-3D-balls.png \| imageR = Paracetamol-from-xtal-3D-vdW.png \| USAN = acetaminophen <!-- Clinical data -->\| pronounce = Paracetamol: {{IPAc-en\|ˌ\|p\|ær\|ə\|ˈ\|s\|iː\|t\|ə\|m\|ɒ\|l}}<br />Acetaminophen: {{IPAc-en\|audio=En-acetaminophen.oga\|ə\|ˌ\|s\|iː\|t\|ə\|ˈ\|m\|ɪ\|n\|ə\|f\|ɪ\|n}}▼ ~~<!-- Clinical data -->~~ ▲\| pronounce = Paracetamol: {{IPAc-en\|ˌ\|p\|ær\|ə\|ˈ\|s\|iː\|t\|ə\|m\|ɒ\|l}}<br />Acetaminophen: {{IPAc-en\|audio=En-acetaminophen.oga\|ə\|ˌ\|s\|iː\|t\|ə\|ˈ\|m\|ɪ\|n\|ə\|f\|ɪ\|n}} \| tradename = [[Tylenol (brand)\|Tylenol]], [[Panadol (brand)\|Panadol]], [[Paracetamol brand names\|others]]<ref name=drugs.com-internatl>{{drugs.com\|international\| acetaminophen}}</ref> \| Drugs.com = {{drugs.com\|monograph\|acetaminophen}} Line 22: \| pregnancy_AU = A \| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web \|title=Acetaminophen Use During Pregnancy \|website=Drugs.com \|date=14 June 2019 \|url=https://www.drugs.com/pregnancy/acetaminophen.html \|access-date=25 February 2020 \|archive-date=9 March 2020 \|archive-url=https://web.archive.org/web/20200309154313/https://www.drugs.com/pregnancy/acetaminophen.html \|url-status=live }}</ref> \| pregnancy_category = \| routes_of_administration = [[Oral administration\|Oral]] (by mouth), [[rectal administration\|rectal]], [[intravenous administration\|intravenous]] (IV) \| class = [[Analgesic]]s and [[antipyretic]]s Line 29: \| ATC_supplemental = {{ATC\|N02\|BE51}} {{ATC\|N02\|BE71}} <!-- Legal status -->\| legal_AU = S4 ~~\| legal_AU = S4~~ \| legal_AU_comment = OTC, and unscheduled \| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F--> \| legal_BR_comment = \| legal_CA = OTC \| legal_CA_comment = / Rx-only<ref>{{cite web \|url=https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00565 \|title=Regulatory Decision Summary – Acetaminophen Injection \|website=[[Health Canada]] \|date=23 October 2014 \|access-date=7 June 2022 \|archive-date=7 June 2022 \|archive-url=https://web.archive.org/web/20220607080419/https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00565 \|url-status=live }}</ref> \| legal_DE = <!-- Anlage I, II, III or Unscheduled--> \| legal_DE_comment = \| legal_NZ = <!-- Class A, B, C --> \| legal_NZ_comment = \| legal_UK = GSL \| legal_UK_comment = \| legal_US = OTC \| legal_US_comment = / Rx-only \| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV--> \| legal_UN_comment = \| legal_status = <!--For countries not listed above--> <!-- Pharmacokinetic data -->\| bioavailability = 63–89%<ref>{{cite book \|isbn=978-0-9873236-7-5 \|title=Acute Pain Management: Scientific Evidence \|veditors=Schug SA, Palmer GM, Scott DA, Halliwell R, Trinca J \|vauthors=((Working Group of the Australian and New Zealand College of Anaesthetists and Faculty of Pain Medicine)) \|year=2015 \|edition=4th \|publisher=Australian and New Zealand College of Anaesthetists (ANZCA), Faculty of Pain Medicine (FPM) \|location=Melbourne \|url=http://fpm.anzca.edu.au/documents/apmse4_2015_final \|format=PDF \|access-date=28 October 2019 \|archive-url=https://web.archive.org/web/20190731120330/http://fpm.anzca.edu.au/documents/apmse4_2015_final \|archive-date=31 July 2019 \|url-status=dead }}</ref>{{rp\|73}}▼ ~~<!-- Pharmacokinetic data -->~~ ▲\| bioavailability = 63–89%<ref>{{cite book \|isbn=978-0-9873236-7-5 \|title=Acute Pain Management: Scientific Evidence \|veditors=Schug SA, Palmer GM, Scott DA, Halliwell R, Trinca J \|vauthors=((Working Group of the Australian and New Zealand College of Anaesthetists and Faculty of Pain Medicine)) \|year=2015 \|edition=4th \|publisher=Australian and New Zealand College of Anaesthetists (ANZCA), Faculty of Pain Medicine (FPM) \|location=Melbourne \|url=http://fpm.anzca.edu.au/documents/apmse4_2015_final \|format=PDF \|access-date=28 October 2019 \|archive-url=https://web.archive.org/web/20190731120330/http://fpm.anzca.edu.au/documents/apmse4_2015_final \|archive-date=31 July 2019 \|url-status=dead }}</ref>{{rp\|73}} \| protein_bound = negligible to 10–25% in overdose<ref name="pmid7039926"/> \| metabolism = Predominantly in the [[liver]]<ref name = TGA>{{cite web\|title=Codapane Forte Paracetamol and codeine phosphate product information\|work=TGA eBusiness Services\|publisher=Alphapharm Pty Limited\|date=29 April 2013\|access-date=10 May 2014\|url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-05623-3\|format=PDF\|archive-date=6 February 2016\|archive-url=https://web.archive.org/web/20160206163239/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-05623-3\|url-status=live}}</ref> Line 55 ⟶ 53: \| onset = Pain relief onset by [[Route of administration\|route]]:<br />[[Oral administration\|oral]]{{nbsp}}– 37{{nbsp}}minutes<ref name="Buccal route">{{cite journal \|vauthors = Pickering G, Macian N, Libert F, Cardot JM, Coissard S, Perovitch P, Maury M, Dubray C \|title = Buccal acetaminophen provides fast analgesia: two randomized clinical trials in healthy volunteers \|journal = Drug Design, Development and Therapy\| volume = 8 \|pages = 1621–1627 \|date = September 2014 \|pmid = 25302017 \|pmc = 4189711 \|doi = 10.2147/DDDT.S63476 \|quote = In postoperative conditions for acute pain of mild to moderate intensity, the quickest reported time to onset of analgesia with APAP is 8 minutes9 for the iv route and 37 minutes6 for the oral route. \|doi-access = free }}</ref><br />[[Intravenous]]{{nbsp}}– 8{{nbsp}}minutes<ref name="Buccal route" /> \| elimination_half-life = 1.9–2.5 hours<ref name="pmid7039926"/> \| duration_of_action = \| excretion = [[Kidney]]<ref name="pmid7039926"/> <!-- Identifiers -->\| CAS_number_Ref = {{cascite\|correct\|??}} ~~\| CAS_number_Ref = {{cascite\|correct\|??}}~~ \| CAS_number = 103-90-2 \| CAS_supplemental = \| PubChem = 1983 \| PubChemSubstance = 46506142 Line 78 ⟶ 75: \| ChEMBL_Ref = {{ebicite\|correct\|EBI}} \| ChEMBL = 112 \| NIAID_ChemDB = \| PDB_ligand = TYL \| synonyms = ''N''-acetyl-''para''-aminophenol (APAP) <!-- Chemical and physical data -->\| IUPAC_name = ''N''-(4-hydroxyphenyl)ethanamide ~~\| IUPAC_name = ''N''-(4-hydroxyphenyl)ethanamide~~ \| C = 8 \| H = 9 Line 91 ⟶ 87: \| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}} \| StdInChI = 1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10) \| StdInChI_comment = \| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}} \| StdInChIKey = RZVAJINKPMORJF-UHFFFAOYSA-N \| density = 1.263 \| density_notes = \| melting_point = 169 \| melting_high = \| melting_notes = <ref>{{cite journal \|doi = 10.1021/ci0500132 \|title = General Melting Point Prediction Based on a Diverse Compound Data Set and Artificial Neural Networks \|year = 2005 \|vauthors=Karthikeyan M, Glen RC, Bender A \|journal = Journal of Chemical Information and Modeling \|volume = 45 \|issue = 3 \|pages = 581–590 \|pmid = 15921448\|s2cid = 13017241 }}</ref><ref>{{cite web \|url = http://lxsrv7.oru.edu/~alang/meltingpoints/meltingpointof.php?csid=1906 \|title = melting point data for paracetamol \|publisher = Lxsrv7.oru.edu \|access-date = 19 March 2011 \|url-status = dead \|archive-url = https://archive.today/20120630213835/http://lxsrv7.oru.edu/~alang/meltingpoints/meltingpointof.php?csid=1906 \|archive-date = 30 June 2012 }}</ref> \| boiling_point = \| boiling_notes = \| solubility = {{ubl\| 7.21{{nbsp}}g/kg (0{{nbsp}}°C)<ref name="paracetamol-solubility">{{cite journal\| doi = 10.1021/je990124v\| title = Solubility of paracetamol in pure solvents\| vauthors=Granberg RA, Rasmuson AC\| journal = [[Journal of Chemical & Engineering Data]]\| volume = 44 \|issue = 6 \|pages = 1391–95\| year = 1999}}</ref>\| 8.21{{nbsp}}g/kg (5{{nbsp}}°C)<ref name="paracetamol-solubility" />\| 9.44{{nbsp}}g/kg (10{{nbsp}}°C)<ref name="paracetamol-solubility" />\| 10.97{{nbsp}}g/kg (15{{nbsp}}°C)<ref name="paracetamol-solubility" />\| 12.78{{nbsp}}g/kg (20{{nbsp}}°C)<ref name="paracetamol-solubility" />\| ~14{{nbsp}}mg/ml (20{{nbsp}}°C)}} \| sol_units = \| specific_rotation = }} <!-- Definition and medical uses --> '''Paracetamol''' ('''acetaminophen'''{{Efn\|Commonly called "acetaminophen" in the US, Canada, Japan, South Korea, and Colombia{{cn\|date=April 2024}}}}) is a non-opioid [[analgesic]] and [[antipyretic]] agent used to treat [[fever]] and mild to moderate [[pain]].<ref name=":2">{{cite journal \| vauthors = Prescott LF \| title = Paracetamol: past, present, and future \| journal = American Journal of Therapeutics \| volume = 7 \| issue = 2 \| pages = 143–147 \| date = March 2000 \| pmid = 11319582 \| doi = 10.1097/00045391-200007020-00011 \| s2cid = 7754908 }}</ref><ref name="pmid19058473"/><ref name= "pmid31892511"/> It is a widely used [[over the counter]] [[medication]]. Common brand names include [[Tylenol (brand)\|Tylenol]] and [[Panadol (brand)\|Panadol]].

Paracetamol: Difference between revisions