flurbiprofen   

GtoPdb Ligand ID: 4194

Synonyms: Ansaid® | Froben®
flurbiprofen is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Flurbiprofen is member of the nonsteroidal anti-inflammatory drug (NSAID) family. It has antipyretic and analgesic activity.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 37.3
Molecular weight 244.09
XLogP 3.76
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)C(c1ccc(c(c1)F)c1ccccc1)C
Isomeric SMILES OC(=O)C(c1ccc(c(c1)F)c1ccccc1)C
InChI InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)
InChI Key SYTBZMRGLBWNTM-UHFFFAOYSA-N
References
1. Bayly CI, Black WC, Léger S, Ouimet N, Ouellet M, Percival MD. (1999)
Structure-based design of COX-2 selectivity into flurbiprofen.
Bioorg. Med. Chem. Lett., 9 (3): 307-12. [PMID:10091674]
2. 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]
3. Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR. (1999)
Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis.
Proc. Natl. Acad. Sci. U.S.A., 96 (13): 7563-8. [PMID:10377455]