Flurbiprofen

Flurbiprofen
Clinical data
Trade names	Ansaid, Ocufen, Strepfen
Other names	(±)-2-fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid
AHFS/Drugs.com	Monograph
MedlinePlus	a687005
Pregnancy; category	AU: B2;
Routes of; administration	By mouth
ATC code	M01AE09 (WHO) , M02AA19 (WHO), R02AX01 (WHO), S01BC04 (WHO);
Legal status
Legal status	AU: S2 (Pharmacy medicine) /S4; CA: ℞-only;
Pharmacokinetic data
Protein binding	> 99%
Metabolism	Liver (CYP2C9)
Elimination half-life	4.7-5.7 hours
Excretion	Kidney
Identifiers
	IUPAC name (RS)-2-(2-fluorobiphenyl-4-yl)propanoic acid;
CAS Number	5104-49-4 ;
PubChem CID	3394;
IUPHAR/BPS	4194;
DrugBank	DB00712 ;
ChemSpider	3277 ;
UNII	5GRO578KLP;
KEGG	D00330 ;
ChEBI	CHEBI:5130 ;
ChEMBL	ChEMBL563 ;
PDB ligand	FLP (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID0037231 ;
ECHA InfoCard	100.023.479
Chemical and physical data
Formula	C15H13FO2
Molar mass	244.265 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	117 °C (243 °F)
	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 ;
	(verify)

Flurbiprofen is a member of the phenylalkanoic acid derivative family of nonsteroidal 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. Side effects are analogous to those of ibuprofen.^[1]

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.^[2]^[3]^: 34

It was patented in 1964 by Boots UK and approved for medical use in 1987.^[4] It was approved in the US in 1988; the first generic was approved in 1994.^[5]^: 158

^ "Lexicomp: Flurbiprofen". Lexicomp. Wolters Kluwer. Retrieved 25 September 2015.
^ Rainsford KD (December 2011). "Fifty years since the discovery of ibuprofen". Inflammopharmacology. 19 (6): 293–297. doi:10.1007/s10787-011-0103-7. PMID 22120888.
^ Fischer J, Ganellin CR (2010). Analogue-based Drug Discovery II. John Wiley & Sons. ISBN 9783527632121.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.
^ Approved Drug Products with Therapeutic Equivalence Evaluations (PDF) (36th ed.). FDA. 2014.

[1] "Lexicomp: Flurbiprofen". Lexicomp. Wolters Kluwer. Retrieved 25 September 2015.

[plat12-2] Rainsford KD (December 2011). "Fifty years since the discovery of ibuprofen". Inflammopharmacology. 19 (6): 293–297. doi:10.1007/s10787-011-0103-7. PMID 22120888.

[3] Fischer J, Ganellin CR (2010). Analogue-based Drug Discovery II. John Wiley & Sons. ISBN 9783527632121.

[Fis2006-4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.

[5] Approved Drug Products with Therapeutic Equivalence Evaluations (PDF) (36th ed.). FDA. 2014.

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