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'''Flurbiprofen''' is a member of the [[phenylalkanoic acid]] derivative family of [[nonsteroidal anti-inflammatory drug]]s (NSAIDs). It is primarily indicated as a pre-operative [[miosis|anti-miotic]] (in an [[eye drop|ophthalmic solution]]) as well as orally for [[arthritis]] or dental pain. Side effects are analogous to those of ibuprofen.<ref>{{cite web|title=Lexicomp: Flurbiprofen|url=http://online.lexi.com/lco/action/doc/retrieve/docid/patch_f/1797302|website=Lexicomp|publisher=Wolters Kluwer|accessdate=25 September 2015}}</ref>
'''Flurbiprofen''' is a member of the [[phenylalkanoic acid]] derivative family of [[nonsteroidal anti-inflammatory drug]]s (NSAIDs). It is primarily indicated as a pre-operative [[miosis|anti-miotic]] (in an [[eye drop|ophthalmic solution]]) as well as orally for [[arthritis]] or dental pain. Side effects are analogous to those of ibuprofen.<ref>{{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}}</ref>


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]].<ref name = plat12>{{cite journal|last1=Halford|first1=GM|last2=Lordkipanidzé|first2=M|last3=Watson|first3=SP|title=50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams.|journal=Platelets|date=2012|volume=23|issue=6|pages=415–22|doi=10.3109/09537104.2011.632032|pmid=22098129}}</ref><ref>Rainsford KD. [http://paperity.org/p/6515758/fifty-years-since-the-discovery-of-ibuprofen Fifty years since the discovery of ibuprofen]. Inflammopharmacology. 2011 Dec;19(6):293-7. {{PMID|22120888}}</ref><ref>Janos Fischer and C. Robin Ganellin. Analogue-based Drug Discovery II. John Wiley & Sons, 2010 {{ISBN|9783527632121}}</ref>{{rp|34}}
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]].<ref name = plat12>{{cite journal | vauthors = Rainsford KD | title = Fifty years since the discovery of ibuprofen | journal = Inflammopharmacology | volume = 19 | issue = 6 | pages = 293–7 | date = December 2011 | pmid = 22120888 | doi = 10.1007/s10787-011-0103-7 }}</ref><ref>{{cite book | first1 = Janos | last1 = Fischer | first2 = C. Robin | last2 = Ganellin | name-list-format = vanc | title = Analogue-based Drug Discovery II. | publisher = John Wiley & Sons | date = 2010 | isbn = 9783527632121 }}</ref>{{rp|34}}


<!-- Society and culture -->
<!-- Society and culture -->
It was patented in 1964 by [[Boots UK]] and approved for medical use in 1987.<ref name=Fis2006>{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=520 |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA520 |language=en}}</ref> It was approved in the US in 1988; the first [[generic drug|generic]] was approved in 1994.<ref>{{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}}</ref>{{rp|158}}
It was patented in 1964 by [[Boots UK]] and approved for medical use in 1987.<ref name=Fis2006>{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin | name-list-format = vanc |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=520 |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA520 |language=en}}</ref> It was approved in the US in 1988; the first [[generic drug|generic]] was approved in 1994.<ref>{{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}}</ref>{{rp|158}}


==Society and culture==
==Society and culture==
===Brand names===
===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.<ref>{{cite web|title=Flurbiprofen - International Brand Names|url=https://www.drugs.com/international/flurbiprofen.html|publisher=Drugs.com|accessdate=14 November 2016}}</ref>
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.<ref>{{cite web|title=Flurbiprofen - International Brand Names|url=https://www.drugs.com/international/flurbiprofen.html|publisher=Drugs.com|access-date=14 November 2016}}</ref>


===Cost===
===Cost===
As of 2015 the cost for a typical month of medication in the United States is 50 to US$100.<ref name=Ric2015>{{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=8}}</ref>
As of 2015 the cost for a typical month of medication in the United States is 50 to US$100.<ref name=Ric2015>{{cite book|last1=Hamilton|first1=Richart | name-list-format = vanc |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=8}}</ref>


==See also==
== See also ==


*[[Flurizan]]
*[[Flurizan]]


==References==
== References ==
{{reflist}}
{{reflist}}


==Further reading==
== Further reading ==
U.S. National Center for Biotechnology Information: [https://www.ncbi.nlm.nih.gov/books/NBK537365/ Medical Genetics Summaries - Flurbiprofen Therapy and CYP2C9 Genotype]
U.S. National Center for Biotechnology Information: [https://www.ncbi.nlm.nih.gov/books/NBK537365/ Medical Genetics Summaries - Flurbiprofen Therapy and CYP2C9 Genotype]


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[[Category:Phenyl alkanoic acids]]
[[Category:Phenyl alkanoic acids]]
[[Category:Propionic acids]]
[[Category:Propionic acids]]



{{respiratory-system-drug-stub}}
{{respiratory-system-drug-stub}}

Revision as of 04:51, 19 September 2019

Flurbiprofen
Clinical data
Trade namesAnsaid, Ocufen, Strepfen
Other names(±)-2-fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid
AHFS/Drugs.comMonograph
MedlinePlusa687005
Pregnancy
category
  • AU: B2
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding> 99%
MetabolismHepatic (CYP2C9)
Elimination half-life4.7-5.7 hours
ExcretionRenal
Identifiers
  • (RS)-2-(2-fluorobiphenyl-4-yl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.023.479 Edit this at Wikidata
Chemical and physical data
FormulaC15H13FO2
Molar mass244.261 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point117 °C (243 °F)
  • Fc2cc(ccc2c1ccccc1)C(C(=O)O)C
  • 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) checkY
  • Key:SYTBZMRGLBWNTM-UHFFFAOYSA-N checkY
  (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.[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]: 34 

It was patented in 1964 by Boots UK and approved for medical use in 1987.[5] It was approved in the US in 1988; the first generic was approved in 1994.[6]: 158 

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.[7]

Cost

As of 2015 the cost for a typical month of medication in the United States is 50 to US$100.[8]

See also

References

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ "Lexicomp: Flurbiprofen". Lexicomp. Wolters Kluwer. Retrieved 25 September 2015.
  3. ^ 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.
  4. ^ Fischer, Janos; Ganellin, C. Robin (2010). Analogue-based Drug Discovery II. John Wiley & Sons. ISBN 9783527632121. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  5. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  6. ^ Approved Drug Products with Therapeutic Equivalence Evaluations (PDF) (36th ed.). FDA. 2014.
  7. ^ "Flurbiprofen - International Brand Names". Drugs.com. Retrieved 14 November 2016.
  8. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 8. ISBN 9781284057560. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)

Further reading

U.S. National Center for Biotechnology Information: Medical Genetics Summaries - Flurbiprofen Therapy and CYP2C9 Genotype

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