Flurbiprofen

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 461102463

| image = Flurbiprofen enantiomers labelled.svg

| image_class = skin-invert-image

| width = 300px

| image2 = Flurbiprofen enantiomers ball-and-stick models from xtal.png

| width2 = 300px

| chirality = Racemic mixture

| tradename = Ansaid, Ocufen, Strepfen

| Drugs.com = {{drugs.com|monograph|flurbiprofen}}

| MedlinePlus = a687005

| pregnancy_AU = B2

| pregnancy_category =

| routes_of_administration = By mouth

| legal_AU = S2

| legal_AU_comment = /S4

| legal_BR =

| legal_BR_comment =

| legal_CA = Rx-only

| legal_CA_comment =

| legal_DE =

| legal_DE_comment =

| legal_NZ =

| legal_NZ_comment =

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| legal_UK_comment =

| legal_US =

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| bioavailability =

| protein_bound = > 99%

| metabolism = Liver (CYP2C9)

| elimination_half-life = 4.7-5.7 hours

| excretion = Kidney

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 5104-49-4

| ATC_prefix = M01

| ATC_suffix = AE09

| ATC_supplemental = , {{ATC|M02|AA19}}, {{ATC|R02|AX01}}, {{ATC|S01|BC04}}

| PubChem = 3394

| IUPHAR_ligand = 4194

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00712

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3277

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5GRO578KLP

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00330

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 5130

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 563

| PDB_ligand = FLP

| IUPAC_name = (RS)-2-(2-fluorobiphenyl-4-yl)propanoic acid

| C = 15

| H = 13

| F = 1

| O = 2

| SMILES = Fc2cc(ccc2c1ccccc1)C(C(=O)O)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SYTBZMRGLBWNTM-UHFFFAOYSA-N

| synonyms = (±)-2-fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid

| melting_point = 117

}}

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.{{cite web|title=Lexicomp: Flurbiprofen|url=http://online.lexi.com/lco/action/doc/retrieve/docid/patch_f/1797302|website=Lexicomp|publisher=Wolters Kluwer|access-date=25 September 2015}}

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.{{cite journal | vauthors = Rainsford KD | title = Fifty years since the discovery of ibuprofen | journal = Inflammopharmacology | volume = 19 | issue = 6 | pages = 293–297 | date = December 2011 | pmid = 22120888 | doi = 10.1007/s10787-011-0103-7 | doi-access = free }}{{cite book | vauthors = Fischer J, Ganellin CR | title = Analogue-based Drug Discovery II. | publisher = John Wiley & Sons | date = 2010 | isbn = 9783527632121 }}{{rp|34}}

It was patented in 1964 by Boots UK and approved for medical use in 1987.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=520 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA520 |language=en}} It was approved in the US in 1988; the first generic was approved in 1994.{{cite book|title=Approved Drug Products with Therapeutic Equivalence Evaluations|date=2014|publisher=FDA|edition=36th|url=http://www.nber.org/fda/orange-book/pdf/UCM071436.pdf}}{{rp|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. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.{{cite press release | title=FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications | website=U.S. Food and Drug Administration (FDA) | date=15 October 2020 | url=https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | access-date=15 October 2020}}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}} {{PD-notice}}{{cite web | title=NSAIDs may cause rare kidney problems in unborn babies | website=U.S. Food and Drug Administration | date=21 July 2017 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic | access-date=15 October 2020}} {{PD-notice}}

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.{{cite web|title=Flurbiprofen - International Brand Names|url=https://www.drugs.com/international/flurbiprofen.html|publisher=Drugs.com|access-date=14 November 2016}}

Flurbiprofen

Adverse effects

Society and culture

=Brand names=

References

Further reading