Flurbiprofen

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]

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)
Pharmacokinetic data
Protein binding	> 99%
Metabolism	Hepatic (CYP2C9)
Elimination half-life	4.7-5.7 hours
Excretion	Renal
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
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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

Adverse effects

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.[6][7] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[6][7]

Society and culture

Brand names

As of 2016 the drug was available worldwide as drops for ophthalmic use and as tablets, both in various strengths, under many brand names which include: Acustop Cataplasma, Adofeed, Anazin, Anflupin, Anorcid, Ansaid, Antadys, Antafen, Antipain, Baenazin, Benactiv, Biprofin, Biprotec, Bro-Z, Brufen, Brufoz, Cebutid, Clinadol, Coryfin, Dispain, Edolfene, Eyeflur, Falken, Fiera, Flu Ro Fen, Flubifix, Flufen, Flugalin, Flupe, Flur di fen, Fluractive, Fluran, Flurbi Pap, Flurbic, Flurbiprofen, Flurbiprofène, Flurbiprofeno, Flurflex, Flurofen, Fluroptic, Fo Bi Pu Luo Fun, Forphen, Fortine, Froben, Frolix, Fubifen, Fubiprofen, Fubofen, Fukon, Fulruban, Furofen, Kai Fen, Kavoflog, Kotton, Lefenine, Majezik, Maprofen, Maxaljin, Maximus, Meiprofen, Neliacan, Nibelon, Nirolex Gola, Ocufen, Ocuflur, Optifen, Orofaringeo, Painil, Profen, Projezik, Ropion, Sigmaprofen, Stayban, Strefen, Strepfen, Strepflam, Strepsils (various formulations), Sulan, Tie Shr Shu, TransAct, Upnon, Urbifen, Yakuban, Zepolas, Zeralgo, Zero-P, and Zeton.[8]

See also

• Flurizan

References

1. "Lexicomp: Flurbiprofen". Lexicomp. Wolters Kluwer. Retrieved 25 September 2015.
2. Rainsford KD (December 2011). "Fifty years since the discovery of ibuprofen". Inflammopharmacology. 19 (6): 293–7. 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.
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.
6. "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.
7. "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.
8. "Flurbiprofen - International Brand Names". Drugs.com. Retrieved 14 November 2016.

Further reading

• Dean L (2019). "Flurbiprofen Therapy and CYP2C9 Genotype". In Pratt VM, McLeod HL, Rubinstein WS, et al. (eds.). Medical Genetics Summaries. National Center for Biotechnology Information (NCBI). PMID 30742399. Bookshelf ID: NBK537365.