Paracetamol

(Redirected from Acetaminophen)

Paracetamol (or acetaminophen) is a common drug for relieving pain. It can also be used to reduce fever, or headache, caused by a cold or a flu.

Paracetamol
Systematic (IUPAC) name
N-(4-hydroxyphenyl)acetamide
Identifiers
CAS number 103-90-2
ATC code N02BE01 N02BE51 N02BE71
PubChem 1983
DrugBank DB00316
ChemSpider 1906
Chemical data
Formula C8H9Template:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxNTemplate:OrganicBoxO2Template:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox 
Mol. mass ?
Synonyms N-acetyl-para-aminophenol (APAP)
Physical data
Density 1.263 g/cm³
Melt. point 169 °C (336 °F) [1][2]
Solubility in water
  • 7.21 g/kg (0 °C)[3]
  • 8.21 g/kg (5 °C)[3]
  • 9.44 g/kg (10 °C)[3]
  • 10.97 g/kg (15 °C)[3]
  • 12.78 g/kg (20 °C)[3]
  • ~14 mg/ml (20 °C)
 mg/mL (20 °C)
Pharmacokinetic data
Bioavailability 63–89%[4]: Script error: The function "hyphen2dash" does not exist. 
Protein binding negligible to 10–25% in overdose[5]
Metabolism Predominantly in the liver[6]
Half life 1.9–2.5 hours[5]
Excretion Urine[5]
Therapeutic considerations
Licence data

US Daily Med:link

Pregnancy cat.

A(AU)

Legal status

?(AU) GSL(UK) OTC(US)

Routes Mouth, rectal, intravenous (IV)

Overview

Synthesis of paracetamol from phenol.
Final step of the synthesis of paracetamol from phenol.

The IUPAC name for paracetamol is acetaminophen.[7] Both acetaminophen and paracetamol both come from the names of the chemicals used in the compound: N-acetyl-para-aminophenol and para-acetyl-amino-phenol. Sometimes, it is shortened as APAP, for N-acetyl-para-aminophenol.

History

Harmon Northrop Morse was the first to make paracetamol, in the year 1878. Drugs made with paracetamol became common in the 1950s. Today, these drugs are some of the most used, together with those containing salicylic acid, Ibuprofen or Diclofenac. Unlike these, paracetamol has no anti-inflammatory properties. In the year 1977, paracetamol was added to the List of Essential Medicines of the WHO.

Safety

Paracetamol is considered safe for use. The drug is easily available without a prescription. Patients sometimes take too much paracetamol, when they do not know how much should be taken. The recommended dose may not work for some people. Other times, it is because they are trying to commit suicide. Very often, a person's liver can be hurt when they take too much paracetamol.[8]

A dose of 150 milligrams (mg) for every kilogram (kg) of the person's weight (about 10 grams for most adults) will lead to permanent liver damage, and may cause the liver to fail. For people whose livers have already been damaged, such as alcoholics, and for those with a limited secretion of paracetamol, this amount can be much smaller.[9]

United Kingdom

In England and Wales, about 30,000 people per year go to the hospital after taking too much paracetamol (called paracetamol poisoning), with about 150 dying of the poisoning. Since a law was passed saying that paracetamol packets cannot be too large, fewer people have been committing suicide with paracetamol.[10] In Great Britain[11] and the United States Paracetamol is the main reason for acute liver failure. About half of the cases are because of an "unintentional overdose".[8]

Mass poisoning incident in 1982

In 1982, there was a case of sabotage.[12][13] Packets of paracetamol had been tampered with: Seven people died, because they had taken poisoned samples. As a result, the FDA made stricter regulations. Also, paracetamol-products worth 100 million US dollars were called back.

Paracetamol Media

References

  1. General Melting Point Prediction Based on a Diverse Compound Data Set and Artificial Neural Networks. Journal of Chemical Information and Modeling 45 (3) (2005). p. 581–590. doi:10.1021/ci0500132.
  2. melting point data for paracetamolLxsrv7.oru.edu. Retrieved 19 March 2011.
  3. 3.0 3.1 3.2 3.3 3.4 Solubility of paracetamol in pure solvents. Journal of Chemical & Engineering Data 44 (6) (1999). p. 1391–95. doi:10.1021/je990124v.
  4. Acute Pain Management: Scientific Evidence (2015). Melbourne: Australian and New Zealand College of Anaesthetists (ANZCA), Faculty of Pain Medicine (FPM). ISBN 978-0-9873236-7-5. Retrieved 28 October 2019.
  5. 5.0 5.1 5.2 Clinical pharmacokinetics of paracetamol. Clin Pharmacokinet 7 (2) (1982). p. 93–107. doi:10.2165/00003088-198207020-00001.
  6. Codapane Forte Paracetamol and codeine phosphate product information. TGA eBusiness Services (29 April 2013)Alphapharm Pty Limited. Retrieved 10 May 2014.
  7. Paracetamol Indications, Uses, Dosage, Drugs Interactions, Side effects. medicaldialogues.in (31 May 2023). Retrieved 8 November 2024.
  8. 8.0 8.1 Larson A. M.. Acetaminophen-induced acute liver failure: results of a United States multicenter, prospective study. Hepatology 42 (6) (2005). p. 1364–1372. doi:10.1002/hep.20948.
  9. Morgan OW, Griffiths C, Majeed A. Interrupted time-series analysis of regulations to reduce paracetamol (acetaminophen) poisoning. PLOS Med. 4 (4) (April 2007). p. e105. doi:10.1371/journal.pmed.0040105.
  10. Chun, L. J.. Acetaminophen hepatotoxicity and acute liver failure.. J Clin Gastroenterol. 43 (4) (2009). p. 342–349. doi:10.1097/MCG.0b013e31818a3854.
  11. G. Dunea: Death over the counter. In: Br Med J. 1983, 286, pp. 211–212. PMID 6401533; Template:PMC.
  12. 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.