Wiki Loves Monuments: Photograph a

monument, help Wikipedia and win!

Learn more

Paracetamol
Article Talk

Paracetamol (acetaminophen[a] or para-

hydroxyacetanilide) is a non-opioid analgesic and
antipyretic agent used to treat fever and mild to
moderate pain.[12][13][14] It is a widely used over the
counter medication and common brand names include
Tylenol and Panadol.

Paracetamol

Clinical data

Pronunciation Paracetamol: /ˌpærǝ

ˈsiːtǝmɒl/
Acetaminophen: /ǝˌsiːtǝ
i
ˈmɪnǝfɪn/

Trade names Tylenol, Panadol, others[1]

Other names N-acetyl-para-

aminophenol (APAP),
acetaminophen (USAN US)

AHFS/Drugs.com Monograph

MedlinePlus a681004

License data US DailyMed: Acetaminophen

US FDA: Acetaminophen

Pregnancy AU: A[2]

category

Routes of Oral (by mouth), rectal,

administration
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
CA: OTC / Rx-only[3]
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[8]

Metabolites APAP gluc, APAP sulfate,

APAP GSH, APAP cys,
AM404, NAPQI[6]

Onset of action Pain relief onset by route:

oral – 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

PubChem CID 1983

PubChem SID 46506142

IUPHAR/BPS 5239

DrugBank DB00316

ChemSpider 1906

UNII 362O9ITL9D

KEGG D00217
C06804

ChEBI CHEBI:46195

ChEMBL ChEMBL112

PDB ligand TYL (PDBe ,

RCSB PDB )

CompTox Dashboard DTXSID2020006

(EPA)

ECHA InfoCard 100.002.870

Chemical and physical data

Formula C8H9NO2

Molar mass 151.165 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)[11]

8.21 g/kg (5 °C)[11]
9.44 g/kg (10 °C)[11]
10.97 g/kg (15 °C)[11]
12.78 g/kg (20 °C)[11]
~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/h2-5,1
1H,1H3,(H,9,10)
Key:RZVAJINKPMORJF-UHFFFAOYSA-N

(verify)

At a standard dose, paracetamol only slightly

decreases body temperature;[13][15][16] it is inferior to
ibuprofen in that respect,[17] and the benefits of its use
for fever are unclear.[13][18][19] Paracetamol may relieve
pain in acute mild migraine but only slightly in episodic
tension headache.[20][21] However, the
aspirin/paracetamol/caffeine combination helps with
both conditions where the pain is mild and is
recommended as a first-line treatment for them.[22][23]
Paracetamol is effective for post-surgical pain, but it is
inferior to ibuprofen.[24] The paracetamol/ibuprofen
combination provides further increase in potency and is
superior to either drug alone.[24][25] The pain relief
paracetamol provides in osteoarthritis is small and
clinically insignificant.[14][26][27] The evidence in its
favor for the use in low back pain, cancer pain, and
neuropathic pain is insufficient.[14][28][26][29][30][31]

In the short term, paracetamol is safe and effective

when used as directed.[32] Short term adverse effects
are uncommon and similar to ibuprofen,[33] but
paracetamol is typically safer than non-steroidal anti-
inflammatory drugs (NSAID) for long term use.[34]
Paracetamol is also often used in patients who cannot
tolerate NSAIDs like ibuprofen.[35][36] Chronic
consumption of paracetamol may result in a drop in
hemoglobin level, indicating possible gastrointestinal
bleeding,[37] and abnormal liver function tests. Some
epidemiological studies have linked paracetamol to
cardiovascular, renal, and gastrointestinal diseases, but
are largely due to confounding biases and of
insignificant relevance with short-term use of
paracetamol.[38][39][37][36][40] Paracetamol may slightly
increase systolic blood pressure in hypertensive
patients at a dose of 4 grams a day.[41][42] Elevated
frequency of asthma and developmental and
reproductive disorders is observed in the offspring of
women with prolonged use of paracetamol during
pregnancy, although whether paracetamol is the true
cause of this increase is unclear.[41] Some studies
suggest that there is evidence for an association
between paracetamol during pregnancy and autism
spectrum disorder and attention deficit hyperactivity
disorder, while making clear further research is
required to establish any causal link,[43][44] which has
prompted some calls to limit its use in pregnancy to the
lowest effective dosage for the shortest possible time.
[41][45][46]

The recommended maximum daily dose for an adult is

three to four grams.[47][48][26] Higher doses may lead
to toxicity, including liver failure.[49] 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.[50][51][52]

Paracetamol was first made in 1878 by Harmon

Northrop Morse or possibly 1852 by Charles Frédéric
Gerhardt.[53][54][55] It is the most commonly used
medication for pain and fever in both the United States
and Europe.[56] It is on the World Health Organization's
List of Essential Medicines.[57] Paracetamol is available
as a generic medication, with brand names including
Tylenol and Panadol among others.[58] In 2020, it was
the 118th most commonly prescribed medication in the
United States, with more than 5 million prescriptions.
[59][60]

Etymology

Medical uses

Adverse effects

Overdose

Interactions

Pharmacology

Chemistry

History

Society and culture

Veterinary use

Notes

References

External links

Last edited 5 days ago by Uniqjdev7

Content is available under CC BY-SA 4.0 unless otherwise

noted.

Terms of Use • Privacy policy • Desktop