ibuprofen   

GtoPdb Ligand ID: 2713

Synonyms: Advil® | Brufen® | ibuprofen lysine | ibuprofen sodium | Motrin® | Nurofen® | U-18573
ibuprofen is an approved drug (FDA (1974), EMA (2004))
Compound class: Synthetic organic
Comment: Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID).

The approved drug is a racemic mixture of the (R)- and (S)-stereoisomers. The (S)-enantiomer is more active, and the (R)-enantiomer is converted in the body to the (S)-enantiomer. We show the non-isomeric molecule to represent the mixture.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 37.3
Molecular weight 206.13
XLogP 3.64
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(Cc1ccc(cc1)C(C(=O)O)C)C
Isomeric SMILES CC(Cc1ccc(cc1)C(C(=O)O)C)C
InChI InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
InChI Key HEFNNWSXXWATRW-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Ibuprofen is used widely for its analgesic and antipyretic actions.
Mechanism Of Action and Pharmacodynamic Effects
Ibuprofen reversibly inhibits cyclooxygenase (COX) enzymes 1 and 2, causing a reduction in synthesis of pro-inflammatory prostaglandins.
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