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Paracetamol information


Paracetamol
Clinical data
PronunciationParacetamol: /ˌpærəˈstəmɒl/
Acetaminophen: /əˌstəˈmɪnəfɪn/
Trade namesTylenol, Panadol, others[1]
Other namesN-acetyl-para-aminophenol (APAP), acetaminophen (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa681004
License data
  • US DailyMed: Acetaminophen
Pregnancy
category
  • AU: A[2]
Routes of
administration
Oral (by mouth), rectal, intravenous (IV)
Drug classAnalgesics and antipyretics
ATC code
  • N02BE01 (WHO) N02BE51 (WHO) N02BE71 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only) OTC, and unscheduled
  • CA: OTC / Rx-only[4]
  • UK: General sales list (GSL, OTC)
  • US: WARNING[3]OTC / Rx-only
Pharmacokinetic data
Bioavailability63–89%[5]: 73 
Protein bindingnegligible to 10–25% in overdose[6]
MetabolismPredominantly in the liver[9]
MetabolitesAPAP gluc, APAP sulfate, APAP GSH, APAP cys, AM404, NAPQI[7]
Onset of actionPain relief onset by route:
oral – 37 minutes[8]
Intravenous – 8 minutes[8]
Elimination half-life1.9–2.5 hours[6]
ExcretionKidney[6]
Identifiers
IUPAC name
  • N-(4-hydroxyphenyl)ethanamide
CAS Number
  • 103-90-2 checkY
PubChem CID
  • 1983
PubChem SID
  • 46506142
IUPHAR/BPS
  • 5239
DrugBank
  • DB00316 checkY
ChemSpider
  • 1906 checkY
UNII
  • 362O9ITL9D
KEGG
  • D00217 checkY
  • C06804
ChEBI
  • CHEBI:46195 checkY
ChEMBL
  • ChEMBL112 checkY
PDB ligand
  • TYL (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID2020006 Edit this at Wikidata
ECHA InfoCard100.002.870 Edit this at Wikidata
Chemical and physical data
FormulaC8H9NO2
Molar mass151.165 g·mol−1
3D model (JSmol)
  • Interactive image
Density1.263 g/cm3
Melting point169 °C (336 °F) [10][11]
Solubility in water
  • 7.21 g/kg (0 °C)[12]
  • 8.21 g/kg (5 °C)[12]
  • 9.44 g/kg (10 °C)[12]
  • 10.97 g/kg (15 °C)[12]
  • 12.78 g/kg (20 °C)[12]
  • ~14 mg/ml (20 °C)
SMILES
  • CC(=O)Nc1ccc(O)cc1
InChI
  • InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10) checkY
  • Key:RZVAJINKPMORJF-UHFFFAOYSA-N checkY
  (verify)

Paracetamol (acetaminophen[a]) is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain.[13][14][15] It is a widely used over the counter medication. Common brand names include Tylenol and Panadol.

At a standard dose, paracetamol slightly decreases body temperature;[14][16][17] it is inferior to ibuprofen in that respect,[18] and the benefits of its use for fever are unclear, particularly in the context of fever of viral origins.[14][19][20] Paracetamol relieves pain in both acute mild migraine and episodic tension headache.[21][22] The aspirin/paracetamol/caffeine combination also helps with both conditions where the pain is mild and is recommended as a first-line treatment for them.[23][24] Paracetamol is effective for post-surgical pain, but it is inferior to ibuprofen.[25] The paracetamol/ibuprofen combination provides further increase in potency and is superior to either drug alone.[25][26] The pain relief paracetamol provides in osteoarthritis is small and clinically insignificant.[15][27][28] The evidence in its favor for the use in low back pain, cancer pain, and neuropathic pain is insufficient.[15][29][27][30][31][32]

In the short term, paracetamol is safe and effective when used as directed.[33] Short term adverse effects are uncommon and similar to ibuprofen,[34] but paracetamol is typically safer than non-steroidal anti-inflammatory drugs (NSAID) for long term use.[35] Paracetamol is also often used in patients who cannot tolerate NSAIDs like ibuprofen.[36][37] Chronic consumption of paracetamol may result in a drop in hemoglobin level, indicating possible gastrointestinal bleeding,[38] and abnormal liver function tests. The recommended maximum daily dose for an adult is three to four grams.[39][40][27] Higher doses may lead to toxicity, including liver failure.[41] Paracetamol poisoning is the foremost cause of acute liver failure in the Western world, and accounts for most drug overdoses in the United States, the United Kingdom, Australia, and New Zealand.[42][43][44]

Paracetamol was first made in 1878 by Harmon Northrop Morse or possibly 1852 by Charles Frédéric Gerhardt.[45][46][47] It is the most commonly used medication for pain and fever in both the United States and Europe.[48] It is on the World Health Organization's List of Essential Medicines.[49] Paracetamol is available as a generic medication, with brand names including Tylenol and Panadol among others.[50] In 2021, it was the 113th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[51][52]

  1. ^ International Drug Names
  2. ^ "Acetaminophen Use During Pregnancy". Drugs.com. 14 June 2019. Archived from the original on 9 March 2020. Retrieved 25 February 2020.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "Regulatory Decision Summary – Acetaminophen Injection". Health Canada. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  5. ^ Working Group of the Australian and New Zealand College of Anaesthetists and Faculty of Pain Medicine (2015). Schug SA, Palmer GM, Scott DA, Halliwell R, Trinca J (eds.). Acute Pain Management: Scientific Evidence (4th ed.). Melbourne: Australian and New Zealand College of Anaesthetists (ANZCA), Faculty of Pain Medicine (FPM). ISBN 978-0-9873236-7-5. Archived from the original (PDF) on 31 July 2019. Retrieved 28 October 2019.
  6. ^ a b c Cite error: The named reference pmid7039926 was invoked but never defined (see the help page).
  7. ^ "Acetaminophen Pathway (therapeutic doses), Pharmacokinetics". Archived from the original on 4 March 2016. Retrieved 13 January 2016.
  8. ^ a b Pickering G, Macian N, Libert F, Cardot JM, Coissard S, Perovitch P, et al. (September 2014). "Buccal acetaminophen provides fast analgesia: two randomized clinical trials in healthy volunteers". Drug Design, Development and Therapy. 8: 1621–1627. doi:10.2147/DDDT.S63476. PMC 4189711. PMID 25302017. 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.
  9. ^ "Codapane Forte Paracetamol and codeine phosphate product information" (PDF). TGA eBusiness Services. Alphapharm Pty Limited. 29 April 2013. Archived from the original on 6 February 2016. Retrieved 10 May 2014.
  10. ^ Karthikeyan M, Glen RC, Bender A (2005). "General Melting Point Prediction Based on a Diverse Compound Data Set and Artificial Neural Networks". Journal of Chemical Information and Modeling. 45 (3): 581–590. doi:10.1021/ci0500132. PMID 15921448. S2CID 13017241.
  11. ^ "melting point data for paracetamol". Lxsrv7.oru.edu. Archived from the original on 30 June 2012. Retrieved 19 March 2011.
  12. ^ a b c d e Granberg RA, Rasmuson AC (1999). "Solubility of paracetamol in pure solvents". Journal of Chemical & Engineering Data. 44 (6): 1391–95. doi:10.1021/je990124v.
  13. ^ Prescott LF (March 2000). "Paracetamol: past, present, and future". American Journal of Therapeutics. 7 (2): 143–147. doi:10.1097/00045391-200007020-00011. PMID 11319582. S2CID 7754908.
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  15. ^ a b c Cite error: The named reference pmid31892511 was invoked but never defined (see the help page).
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  19. ^ Meremikwu M, Oyo-Ita A (2002). "Paracetamol for treating fever in children". Cochrane Database Syst Rev. 2002 (2): CD003676. doi:10.1002/14651858.CD003676. PMC 6532671. PMID 12076499.
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  25. ^ a b Cite error: The named reference pmid24338830 was invoked but never defined (see the help page).
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  27. ^ a b c Cite error: The named reference BMJ2015 was invoked but never defined (see the help page).
  28. ^ Cite error: The named reference pmid31908149 was invoked but never defined (see the help page).
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  32. ^ Cite error: The named reference pmid28027389 was invoked but never defined (see the help page).
  33. ^ "Acetaminophen". Health Canada. 11 October 2012. Archived from the original on 3 November 2022. Retrieved 22 September 2022.
  34. ^ Southey ER, Soares-Weiser K, Kleijnen J (September 2009). "Systematic review and meta-analysis of the clinical safety and tolerability of ibuprofen compared with paracetamol in paediatric pain and fever". Current Medical Research and Opinion. 25 (9): 2207–2222. doi:10.1185/03007990903116255. PMID 19606950. S2CID 31653539. Archived from the original on 3 January 2023. Retrieved 2 December 2022.
  35. ^ "Acetaminophen vs Ibuprofen: Which is better?". Drugs.com. Archived from the original on 19 February 2023. Retrieved 22 September 2022.
  36. ^ Moore RA, Moore N (July 2016). "Paracetamol and pain: the kiloton problem". European Journal of Hospital Pharmacy. 23 (4): 187–188. doi:10.1136/ejhpharm-2016-000952. PMC 6451482. PMID 31156845.
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  39. ^ "Paracetamol for adults: painkiller to treat aches, pains and fever". National Health Service. Archived from the original on 22 August 2017. Retrieved 22 August 2017.
  40. ^ "What are the recommended maximum daily dosages of acetaminophen in adults and children?". Medscape. Archived from the original on 21 December 2018. Retrieved 19 December 2018.
  41. ^ "Acetaminophen". The American Society of Health-System Pharmacists. Archived from the original on 5 June 2016. Retrieved 16 September 2016.
  42. ^ Daly FF, Fountain JS, Murray L, Graudins A, Buckley NA (March 2008). "Guidelines for the management of paracetamol poisoning in Australia and New Zealand—explanation and elaboration. A consensus statement from clinical toxicologists consulting to the Australasian poisons information centres". The Medical Journal of Australia. 188 (5): 296–301. doi:10.5694/j.1326-5377.2008.tb01625.x. PMID 18312195. S2CID 9505802.
  43. ^ Hawkins LC, Edwards JN, Dargan PI (2007). "Impact of restricting paracetamol pack sizes on paracetamol poisoning in the United Kingdom: a review of the literature". Drug Saf. 30 (6): 465–79. doi:10.2165/00002018-200730060-00002. PMID 17536874. S2CID 36435353.
  44. ^ Larson AM, Polson J, Fontana RJ, Davern TJ, Lalani E, Hynan LS, et al. (2005). "Acetaminophen-induced acute liver failure: results of a United States multicenter, prospective study". Hepatology. 42 (6): 1364–72. doi:10.1002/hep.20948. PMID 16317692. S2CID 24758491.
  45. ^ Mangus BC, Miller MG (2005). Pharmacology application in athletic training. Philadelphia, Pennsylvania: F.A. Davis. p. 39. ISBN 9780803620278. Archived from the original on 8 September 2017. Retrieved 7 September 2017.
  46. ^ Eyers SJ (April 2012). The effect of regular paracetamol on bronchial responsiveness and asthma control in mild to moderate asthma (Ph.D. thesis). University of Otago). Archived from the original on 24 August 2021. Retrieved 24 August 2021.
  47. ^ Roy J (2011). "Paracetamol – the best selling antipyretic analgesic in the world". An introduction to pharmaceutical sciences: production, chemistry, techniques and technology. Oxford: Biohealthcare. p. 270. ISBN 978-1-908818-04-1. Archived from the original on 24 August 2021. Retrieved 24 August 2021.
  48. ^ Aghababian RV (22 October 2010). Essentials of emergency medicine. Jones & Bartlett Publishers. p. 814. ISBN 978-1-4496-1846-9. Archived from the original on 17 August 2016.
  49. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  50. ^ Hamilton RJ (2013). Tarascon pocket pharmacopoeia : 2013 classic shirt-pocket edition (27th ed.). Burlington, Massachusetts: Jones & Bartlett Learning. p. 12. ISBN 9781449665869. Archived from the original on 8 September 2017.
  51. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  52. ^ "Acetaminophen - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.


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Paracetamol

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Paracetamol (acetaminophen) is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely used over the...

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Paracetamol poisoning

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Paracetamol poisoning, also known as acetaminophen poisoning, is caused by excessive use of the medication paracetamol (acetaminophen). Most people have...

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List of paracetamol brand names

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The medication paracetamol (INN) (/ˌpærəˈsiːtəmɒl/ or /ˌpærəˈsɛtəmɒl/), also known as acetaminophen (USAN) (/əˌsiːtəˈmɪnəfɪn/ ), is sold around the world...

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Dextropropoxyphene

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dextropropoxyphene and paracetamol). The British approved name (i.e. the generic name of the active ingredient) of the paracetamol/dextropropoxyphene preparation...

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Acetylcysteine

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known as N-acetylcysteine (NAC), is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals with chronic bronchopulmonary...

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Ibuprofen

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with risk of progression to hypertension in women, though less than for paracetamol (acetaminophen), and myocardial infarction (heart attack), particularly...

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Analgesic

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Analgesics are typically classified based on their mechanism of action. Paracetamol, also known as acetaminophen or APAP, is a medication used to treat pain...

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Codeine

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pain.[failed verification] Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such...

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International nonproprietary name

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spelling or pronunciation differences, for example: paracetamol (en) paracetamolum (la), paracétamol (fr) and парацетамол (ru). An established INN is known...

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PICO process

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headaches; keywords = children + headache Intervention = Paracetamol; keyword = paracetamol Compared with = Placebo; keyword = placebo Outcome of interest...

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Cold water extraction

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with codeine/paracetamol, hydrocodone/paracetamol and oxycodone/paracetamol medications, it is not effective at removing all of the paracetamol. The cold...

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Antipyretic

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analgesics (pain relievers), but which also have antipyretic properties; and paracetamol (acetaminophen), an analgesic without anti-inflammatory properties. There...

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Solpadeine

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name of a range of analgesic medication containing various amounts of paracetamol, ibuprofen, caffeine and codeine, made by Omega Pharma. The range was...

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Pleurisy

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electrocardiogram (ECG), and blood tests. Treatment depends on the underlying cause. Paracetamol (acetaminophen) and ibuprofen may be used to decrease pain. Incentive...

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Phenacetin

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non-opioid analgesics without anti-inflammatory properties. Although paracetamol (acetaminophen) was produced earlier, a historical accident saw it ignored...

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Propyphenazone

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in 1931, propyphenazone is marketed as a combination formulation with paracetamol and caffeine for treatment of primary headache disorder. Case reports...

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Dihydrocodeine

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severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) (as in co-dydramol) or aspirin. It was developed in Germany...

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Butalbital

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action. Butalbital is often combined with other medications, such as paracetamol (acetaminophen) (as Butalbital/acetaminophen) or aspirin, for the treatment...

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Acetanilide

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classes, but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially...

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