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
Classification
Compound class Synthetic organic
Ligand families/groups Non-steroidal anti-inflammatory ligands
Approved drug? Yes (FDA (1974), EMA (2004))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
2-[4-(2-methylpropyl)phenyl]propanoic acid
International Nonproprietary Names
INN number INN
2118 ibuprofen
Synonyms
Advil® | Brufen® | ibuprofen lysine | ibuprofen sodium | Motrin® | Nurofen® | U-18573
Database Links
BindingDB Ligand 50009859
CAS Registry No. 15687-27-1 (source: ChEBI)
ChEBI CHEBI:5855
ChEMBL Ligand CHEMBL521
DrugBank Ligand DB01050
DrugCentral Ligand 1407
GtoPdb PubChem SID 135650365
Immunopaedia Search ibuprofen
PubChem CID 3672
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Wikipedia Ibuprofen