paracetamol   Click here for help

GtoPdb Ligand ID: 5239

Synonyms: acetaminophen | N-Acetyl-p-aminophenol | Panadol® | Tylenol®
Approved drug PDB Ligand
paracetamol is an approved drug (FDA (1968))
Compound class: Synthetic organic
Comment: Paracetamol is approved by the US FDA as acetaminophen. It is a widely used analgesic and antipyretic drug. Despite its widespread use the mechanism of action of paracetamol is incompletely understood [2].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: paracetamol

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 49.33
Molecular weight 151.06
XLogP 0.87
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CC(=O)Nc1ccc(cc1)O
Isomeric SMILES CC(=O)Nc1ccc(cc1)O
InChI InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
No information available.
Summary of Clinical Use Click here for help
Used to relieve pain and reduce fever. The therapeutic effects of paracetamol are similar to those of the aspirin-like compounds, but it does not have any anti-inflammatory or antiplatelet effects and does not irritate the lining of the stomach.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Paracetamol inhibits the activity of both isoforms of cyclooxygenase in vitro [1]. However, the favourable risk profile of paracetamol compared to COX inhibiting NSAIDs is perhaps indicative of some selectivity towards COX-2 in vivo [1], since COX-1 inhibition has been linked to the adverse gastrointestinal effects of non-selective COX inhibitors. COX inhibition may not fully explain the clinical efficacy of paracetamol, and the contribution of an indirect mechanism cannot be ruled out.
External links Click here for help