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Paracetamol

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Paracetamol
Clinical data
PronunciationParacetamol:/ˌpærəˈsiːtəmɒl/
Acetaminophen:/əˌsiːtəˈmɪnəfɪn/(audio speaker iconlisten)
Trade namesTylenol,Panadol,others[2]
SynonymsN-acetyl-para-aminophenol (APAP), acetaminophen (USANUS)
AHFS/DrugsMonograph
MedlinePlusa681004
License data
Pregnancy
category
Routes of
administration		By mouth,rectal,intravenous(IV)
Drug classAnalgesics and antipyretics
ATC code
Legal status
Legal status
Pharmacokineticdata
Bioavailability63–89%[4]: 73 
Protein bindingnegligible to 10–25% in overdose[5]
MetabolismPredominantly in the liver[3]
MetabolitesAPAPgluc,APAPsulfate,APAPGSH,APAPcys,AM404,NAPQI[6]
Onset of actionPain relief onset byroute:
By mouth– 37minutes[7]
Intravenous– 8minutes[7]
Eliminationhalf-life1.9–2.5 hours[5]
ExcretionUrine[5]
Identifiers
  • N-(4-hydroxyphenyl)acetamide
CAS Number
PubChemCID
PubChemSID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDBligand
ECHA InfoCard100.002.870Edit this at Wikidata
Chemical and physical data
FormulaC8H9NO2
Molar mass151.17 g·mol−1
3D model (JSmol)
Density1.263 g/cm3
Melting point169 °C (336 °F)[9][10]
Solubility in water
  • 7.21g/kg (0°C)[8]
  • 8.21g/kg (5°C)[8]
  • 9.44g/kg (10°C)[8]
  • 10.97g/kg (15°C)[8]
  • 12.78g/kg (20°C)[8]
  • ~14mg/ml (20°C)
  • CC(=O)Nc1ccc(O)cc1
  • 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-NcheckY
(verify)

Paracetamol(oracetaminophen) is a commonanalgesic,adrugthat is used to relievepain.It can also be used to reducefever,and some kinds ofheadache.This makes it anantipyretic,something that reduces fevers. It is used in many drugs that treatthe fluandcolds.

The wordsacetaminophenandparacetamolboth come from the names of the chemicals used in the compound: N-acetyl-para-aminophenol andpara-acetyl-amino-phenol.Sometimes, it is shortened toAPAP,for N-acetyl-para-aminophenol.

Harmon Northrop Morsewas the first to make Paracetamol, in the year1878.Drugs made with Paracetamol became common in the 1950s. Today, these drugs are some of the most used, together with those containingsalicylic acid,IbuprofenorDiclofenac.Unlike these, Paracetamol has noanti-inflammatoryproperties. In the year 1977, Paracetamol was added to theList of Essential Medicinesof theWHO.

Safety and dosage

[change|change source]

Paracetamol is considered safe for use. The drug is easily available without aprescription.People often take too much Paracetamol. Sometimes this is because people do not know how much they should take. The recommendeddosemay not work for some people. Other times it is because they are trying to commitsuicide.Very often, a person'slivercan be hurt when they take too much Paracetamol.[11]A dose of 150milligramsfor everykilogramof the person's weight (about 10gramsfor most adults) will lead to permanent liver damage, and may cause the liver tofail.For people whose livers have already been damaged, such asalcoholics,and for those with a limited secretion of Paracetamol, this amount can be much smaller.[12][13][14] InEnglandandWales,about 30.000 people per year go to the hospital after taking too much paracetamol (called paracetamol poisoning), and about 150 die of the poisoning. Since a law was passed saying that Paracetamol packets cannot be too large, fewer people have been committing suicide with Paracetamol.[15]InGreat Britain[16]and theUnited StatesParacetamol is the main reason for acuteliver failure.About half of the cases are because of an 'unintentional overdose'.[11]

In 1982, there was a case ofsabotage:[17][18]Packets of paracetamol had been tampered with: Seven peoppel died, because they had takenpoisonedsamples. As a result, theFDAmade stricter regulations. Also, Paracetamol-products worth 100 million US dollars were called back.

References

[change|change source]
  1. ↑"Acetaminophen Use During Pregnancy".Drugs.14 June 2019.Archivedfrom the original on 9 March 2020.Retrieved25 February2020.
  2. ↑International Drug Names
  3. ↑"Codapane Forte Paracetamol and codeine phosphate product information"(PDF).TGA eBusiness Services.Alphapharm Pty Limited. 29 April 2013.Archivedfrom the original on 6 February 2016.Retrieved10 May2014.
  4. ↑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).ISBN978-0-9873236-7-5.Archived fromthe original(PDF)on 31 July 2019.Retrieved28 October2019.
  5. ↑5.05.15.2Forrest JA, Clements JA, Prescott LF (1982). "Clinical pharmacokinetics of paracetamol".Clin Pharmacokinet.7(2): 93–107.doi:10.2165/00003088-198207020-00001.PMID7039926.S2CID20946160.
  6. ↑"Acetaminophen Pathway (therapeutic doses), Pharmacokinetics".Archived fromthe originalon 4 March 2016.Retrieved13 January2016.
  7. ↑7.07.1Pickering G, Macian N, Libert F, Cardot JM, Coissard S, Perovitch P, Maury M, Dubray C (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.PMC4189711.PMID25302017.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.
  8. ↑8.08.18.28.38.4Granberg RA, Rasmuson AC (1999). "Solubility of paracetamol in pure solvents".Journal of Chemical & Engineering Data.44(6): 1391–95.doi:10.1021/je990124v.
  9. ↑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.PMID15921448.
  10. ↑"melting point data for paracetamol".Lxsrv7.oru.edu. Archived fromthe originalon 30 June 2012.Retrieved19 March2011.
  11. ↑11.011.1Larson A. M.; et al. (2005)."Acetaminophen-induced acute liver failure: results of a United States multicenter, prospective study".Hepatology.42(6): 1364–1372.doi:10.1002/hep.20948.PMID16317692.S2CID24758491.
  12. ↑Roberts, L. Jackson; Morrow, Jason D. (2001). "Analgesic-antipyretic and antiinflammatory agents and drugs employed in the treatment of gout". In Gilman, Alfred; Goodman, Louis Sanford; Hardman, Joel G.; Limbird, Lee E. (ed.).Goodman & Gilman's the pharmacological basis of therapeutics.New York: McGraw-Hill. pp. 687–732.ISBN0-07-112432-2.{{cite book}}:CS1 maint: multiple names: authors list (link)
  13. ↑Williams, Roger Lawrence; Jean-Pierre Benhamou; Lee, William Thomas (1997).Acute liver failure.Cambridge, UK: Cambridge University Press.ISBN0-521-55381-4.{{cite book}}:CS1 maint: multiple names: authors list (link)
  14. ↑"8 Paracetamol Guidelines for Patients".PR Fire.Archived fromthe originalon 2021-01-24.Retrieved2021-02-12.
  15. ↑Morgan OW, Griffiths C, Majeed A (April 2007)."Interrupted time-series analysis of regulations to reduce paracetamol (acetaminophen) poisoning".PLOS Med.4(4): e105.doi:10.1371/journal.pmed.0040105.PMC1845154.PMID17407385.{{cite journal}}:CS1 maint: multiple names: authors list (link)
  16. ↑Chun, L. J.; et al. (2009). "Acetaminophen hepatotoxicity and acute liver failure".J Clin Gastroenterol.43(4): 342–349.doi:10.1097/MCG.0b013e31818a3854.PMID19169150.
  17. ↑G. Dunea:Death over the counter.In:Br Med J.1983, 286, pp. 211–212.PMID 6401533;PMC1546319.
  18. ↑K. A. Wolnik, F. L. Fricke, E. Bonnin, C. M. Gaston, R. D. Satzger:The Tylenol tampering incident – tracing the source.In:Anal. Chem.56, 1984, pp. 466A–470A, 474A.PMID 6711821.
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