Acetaminophen

Paracetamol

Clinical data
Pronunciation	Paracetamol: /ˌpærəˈsitəmɒl/ Acetaminophen: i/əˌsiːtəˈmɪnəfᵻn/
Trade names	Tylenol, Panadol, others
AHFS/Drugs.com	Monograph
MedlinePlus	a681004
License data	US FDA: Acetaminophen
Pregnancy category	AU: A US: C (Risk not ruled out) Not tested but seems to be safe
Routes of administration	By mouth, through the cheek, rectal, intravenous (IV)
ATC code	N02BE01 (WHO)
Legal status
Legal status	AU: Unscheduled UK: General sales list (GSL, OTC) US: OTC
Pharmacokinetic data
Bioavailability	63–89%
Protein binding	10–25%
Metabolism	Predominantly in the liver
Metabolites	APAP gluc, APAP sulfate, APAP GSH, APAP cys, NAPQI
Onset of action	Pain relief onset by route: By mouth – 37 minutes Buccal – 15 minutes Intravenous – 8 minutes
Biological half-life	1–4 hours
Excretion	Urine (85–90%)
Identifiers
IUPAC name N-(4-hydroxyphenyl)ethanamide N-(4-hydroxyphenyl)acetamide
Synonyms	N-acetyl-para-aminophenol (APAP)
CAS Number	103-90-2 Y
PubChem CID	1983
IUPHAR/BPS	5239
DrugBank	DB00316 Y
ChemSpider	1906 Y
UNII	362O9ITL9D
KEGG	D00217 Y
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	151.163 g/mol
3D model (Jmol)	Interactive image
Density	1.263 g/cm3
Melting point	169 °C (336 °F)
Boiling point	420 °C (788 °F)
Solubility in water	7.21 g/kg (0 °C) 8.21 g/kg (5 °C) 9.44 g/kg (10 °C) 10.97 g/kg (15 °C) 12.78 g/kg (20 °C) ~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

7.21 g/kg (0 °C)
8.21 g/kg (5 °C)
9.44 g/kg (10 °C)
10.97 g/kg (15 °C)
12.78 g/kg (20 °C)

Paracetamol, also known as acetaminophen or APAP, is a medication used to treat pain and fever. It is typically used for mild to moderate pain. There is poor evidence for fever relief in children. It is often sold in combination with other ingredients such as in many cold medications. In combination with opioid pain medication, paracetamol is used for more severe pain such as cancer pain and after surgery. It is typically used either by mouth or rectally but is also available intravenously. Effects last between two and four hours.

Paracetamol is generally safe at recommended doses. Serious skin rashes may rarely occur, and too high a dose can result in liver failure. It appears to be safe during pregnancy and when breastfeeding. In those with liver disease, it may still be used, but lower doses should be taken. Paracetamol is classified as a mild analgesic. It does not have significant anti-inflammatory activity and how it works is not entirely clear.

Paracetamol was discovered in 1877. It is the most commonly used medication for pain and fever in both the United States and Europe. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Paracetamol is available as a generic medication with trade names including Tylenol and Panadol among others. The wholesale price in the developing world is less than 0.01 USD per dose. In the United States it costs about 0.04 USD per dose.