Paracetamol

Paracetamol

Clinical data
Pronunciation	Paracetamol: /ˌpærəˈsiːtəmɒl/ Acetaminophen: /əˌsiːtəˈmɪnəfɪn/ (listen)
Trade names	Tylenol, Panadol, others[2]
Synonyms	N-acetyl-para-aminophenol (APAP), acetaminophen (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a681004
License data	US DailyMed: Acetaminophen US FDA: Acetaminophen
Pregnancy category	AU: A[1]
Routes of administration	By mouth, rectal, intravenous (IV)
Drug class	Analgesics and antipyretics
ATC code	N02BE01 (WHO) N02BE51 (WHO) N02BE71 (WHO)
Legal status
Legal status	AU: S4 (Rx), OTC, and unscheduled UK: General sales list (GSL, OTC) US: OTC / Rx-only
Pharmacokinetic data
Bioavailability	63–89%[4]: 73
Protein binding	negligible to 10–25% in overdose[5]
Metabolism	Predominantly in the liver[3]
Metabolites	APAP gluc, APAP sulfate, APAP GSH, APAP cys, AM404, NAPQI[6]
Onset of action	Pain relief onset by route: By mouth – 37 minutes[7] Intravenous – 8 minutes[7]
Elimination half-life	1.9–2.5 hours[5]
Excretion	Urine[5]
Identifiers
IUPAC name N-(4-hydroxyphenyl)acetamide
CAS Number	103-90-2 Y
PubChem CID	1983
PubChem SID	46506142
IUPHAR/BPS	5239
DrugBank	DB00316 Y
ChemSpider	1906 Y
UNII	362O9ITL9D
KEGG	D00217 Y C06804
ChEBI	CHEBI:46195 Y
ChEMBL	ChEMBL112 Y
PDB ligand	TYL (PDBe, RCSB PDB)
ECHA InfoCard	100.002.870
Chemical and physical data
Formula	C8H9NO2
Molar mass	151.17 g·mol−1
3D model (JSmol)	Interactive image
Density	1.263 g/cm3
Melting point	169 °C (336 °F) [9][10]
Solubility in water	7.21 g/kg (0 °C)[8] 8.21 g/kg (5 °C)[8] 9.44 g/kg (10 °C)[8] 10.97 g/kg (15 °C)[8] 12.78 g/kg (20 °C)[8] ~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) Y Key:RZVAJINKPMORJF-UHFFFAOYSA-N Y
(verify)

Paracetamol (or acetaminophen) is a common analgesic, a drug that is used to relieve pain. It can also be used to reduce fever, and some kinds of headache. This makes it an antipyretic, something that reduces fevers. It is used in many drugs that treat the flu and colds.

The IUPAC (International Union of Pure and Applied Chemistry) name for paracetamol is Acetaminophen.^[11] The words 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 to APAP, for N-acetyl-para-aminophenol.

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.

1. ↑ "Acetaminophen Use During Pregnancy". Drugs.com. 14 June 2019. Archived from the original on 9 March 2020. Retrieved 25 February 2020.
2. ↑ International Drug Names
3. ↑ "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.
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). ISBN 978-0-9873236-7-5. Archived from the original (PDF) on 31 July 2019. Retrieved 28 October 2019.
5. ↑ ^{5.0 5.1 5.2} Forrest JA, Clements JA, Prescott LF (1982). "Clinical pharmacokinetics of paracetamol". Clin Pharmacokinet. 7 (2): 93–107. doi:10.2165/00003088-198207020-00001. PMID 7039926. S2CID 20946160.
6. ↑ "Acetaminophen Pathway (therapeutic doses), Pharmacokinetics". Archived from the original on 4 March 2016. Retrieved 13 January 2016.
7. ↑ ^{7.0 7.1} Pickering 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. 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.
8. ↑ ^{8.0 8.1 8.2 8.3 8.4} Granberg 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. PMID 15921448.
10. ↑ "melting point data for paracetamol". Lxsrv7.oru.edu. Archived from the original on 30 June 2012. Retrieved 19 March 2011.
11. ↑ "Paracetamol Indications, Uses, Dosage, Drugs Interactions, Side effects". medicaldialogues.in. 31 May 2023. Retrieved 8 November 2024.