Flurbiprofen

Flurbiprofen

Systematic (IUPAC) name
(RS)-2-(2-fluorobiphenyl-4-yl)propanoic acid
Clinical data
Trade names	Ansaid, Ocufen, Strepfen
AHFS/Drugs.com	monograph
MedlinePlus	a687005
Pregnancy category	C (U.S.), B2 (Au)
Routes of administration	Oral
Legal status
Legal status	POD
Pharmacokinetic data
Protein binding	> 99%
Metabolism	Hepatic (CYP2C9)
Biological half-life	4.7-5.7 hours
Excretion	Renal
Identifiers
CAS Number	5104-49-4
ATC code	M01AE09 (WHO) , M02AA19 (WHO), R02AX01 (WHO), S01BC04 (WHO)
PubChem	CID 3394
IUPHAR/BPS	4194
DrugBank	DB00712
ChemSpider	3277
UNII	5GRO578KLP
KEGG	D00330
ChEBI	CHEBI:5130
ChEMBL	CHEMBL563
Synonyms	(±)-2-fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid
PDB ligand ID	FLP (PDBe, RCSB PDB)
Chemical data
Formula	C15H13FO2
Molar mass	244.261 g/mol
Chirality	Racemic mixture
SMILES Fc2cc(ccc2c1ccccc1)C(C(=O)O)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) Key:SYTBZMRGLBWNTM-UHFFFAOYSA-N
Physical data
Melting point	117 °C (243 °F)
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Flurbiprofen is a member of the phenylalkanoic acid derivative family of non-steroidal anti-inflammatory drugs (NSAIDs). It is primarily indicated as a pre-operative anti-miotic (in an ophthalmic solution) as well as orally for arthritis or dental pain.^[1] It is generic and is marketed under brand names worldwide, including "Ansaid" and "Froben".^[2]

It was derived from propionic acid by the research arm of Boots UK during the 1960s, a period which also included the discovery of ibuprofen, indometacin, diclofenac, naproxen, ketoprofen, and sulindac.^[3][4][5]:34

Side effects are analogous to those of ibuprofen. As of 2015 the cost for a typical month of medication in the United States is 50 to 100 USD.^[6]

References

1. "Lexicomp: Flurbiprofen". Lexicomp. Wolters Kluwer. Retrieved 25 September 2015.
2. Drugs.com Flurbiprofen listings at drugs.com Page accessed July 3, 2015
3. Halford, GM; Lordkipanidzé, M; Watson, SP (2012). "50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams.". Platelets 23 (6): 415–22. doi:10.3109/09537104.2011.632032. PMID 22098129.
4. Rainsford KD. Fifty years since the discovery of ibuprofen. Inflammopharmacology. 2011 Dec;19(6):293-7. PMID 22120888
5. Janos Fischer and C. Robin Ganellin. Analogue-based Drug Discovery II. John Wiley & Sons, 2010 ISBN 9783527632121
6. Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 8. ISBN 9781284057560.