ketoprofen   Click here for help

GtoPdb Ligand ID: 4795

Synonyms: Actron® | Orudis®
Approved drug Immunopharmacology Ligand
ketoprofen is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: The approved drug ketoprofen is a mixture of two stereoisomers; an (R)-enantiomer (see PubChem CID 180540), and an (S)-enantiomer (see PubChem CID 667550), with only the (S)-enantiomer possessing biological activity. The structure shown here does not specify stereochemistry and represents the mixture of isomers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 54.37
Molecular weight 254.09
XLogP 3.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)C
Isomeric SMILES OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)C
InChI InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
InChI Key DKYWVDODHFEZIM-UHFFFAOYSA-N
References
1. Bézière N, Goossens L, Pommery J, Vezin H, Touati N, Hénichart JP, Pommery N. (2008)
New NSAIDs-NO hybrid molecules with antiproliferative properties on human prostatic cancer cell lines.
Bioorg. Med. Chem. Lett., 18 (16): 4655-7. [PMID:18667313]
2. 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]