ibuprofen   Click here for help

GtoPdb Ligand ID: 2713

Synonyms: Advil® | Brufen® | ibuprofen lysine | ibuprofen sodium | Motrin® | Nurofen® | U-18573
Approved drug Immunopharmacology Ligand
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: ibuprofen

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
1. Itagaki S, Gopal E, Zhuang L, Fei YJ, Miyauchi S, Prasad PD, Ganapathy V. (2006)
Interaction of ibuprofen and other structurally related NSAIDs with the sodium-coupled monocarboxylate transporter SMCT1 (SLC5A8).
Pharm Res, 23 (6): 1209-16. [PMID:16729224]
2. Janusz JM, Young PA, Scherz MW, Enzweiler K, Wu LI, Gan L, Pikul S, McDow-Dunham KL, Johnson CR, Senanayake CB et al.. (1998)
New cyclooxygenase-2/5-lipoxygenase inhibitors. 2. 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran derivatives as gastrointestinal safe antiinflammatory and analgesic agents: variations of the dihydrobenzofuran ring.
J Med Chem, 41 (7): 1124-37. [PMID:9544212]
3. Jaradat MS, Wongsud B, Phornchirasilp S, Rangwala SM, Shams G, Sutton M, Romstedt KJ, Noonan DJ, Feller DR. (2001)
Activation of peroxisome proliferator-activated receptor isoforms and inhibition of prostaglandin H(2) synthases by ibuprofen, naproxen, and indomethacin.
Biochem Pharmacol, 62 (12): 1587-95. [PMID:11755111]
4. Kojo H, Fukagawa M, Tajima K, Suzuki A, Fujimura T, Aramori I, Hayashi K, Nishimura S. (2003)
Evaluation of human peroxisome proliferator-activated receptor (PPAR) subtype selectivity of a variety of anti-inflammatory drugs based on a novel assay for PPAR delta(beta).
J Pharmacol Sci, 93 (3): 347-55. [PMID:14646253]
5. Lynagh T, Romero-Rojo JL, Lund C, Pless SA. (2017)
Molecular Basis for Allosteric Inhibition of Acid-Sensing Ion Channel 1a by Ibuprofen.
J Med Chem, 60 (19): 8192-8200. [PMID:28949138]
6. Viegas A, Manso J, Corvo MC, Marques MM, Cabrita EJ. (2011)
Binding of ibuprofen, ketorolac, and diclofenac to COX-1 and COX-2 studied by saturation transfer difference NMR.
J Med Chem, 54 (24): 8555-62. [PMID:22091869]
7. Voilley N, de Weille J, Mamet J, Lazdunski M. (2001)
Nonsteroid anti-inflammatory drugs inhibit both the activity and the inflammation-induced expression of acid-sensing ion channels in nociceptors.
J Neurosci, 21 (20): 8026-33. [PMID:11588175]