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Flurbiprofen

April 11, 2024

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]

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		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding> 99%
MetabolismLiver (CYP2C9)
Elimination half-life4.7-5.7 hours
ExcretionKidney
Identifiers
  • (RS)-2-(2-fluorobiphenyl-4-yl)propanoic acid
CAS Number
  • 5104-49-4 Y
PubChem CID
  • 3394
IUPHAR/BPS
  • 4194
DrugBank
  • DB00712 Y
ChemSpider
  • 3277 Y
UNII
  • 5GRO578KLP
KEGG
  • D00330 Y
ChEBI
  • CHEBI:5130 Y
ChEMBL
  • ChEMBL563 Y
PDB ligand
  • FLP (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID0037231
ECHA InfoCard100.023.479
Chemical and physical data
FormulaC15H13FO2
Molar mass244.265 g·mol−1
3D model (JSmol)
  • Interactive image
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) Y
  • Key:SYTBZMRGLBWNTM-UHFFFAOYSA-N Y
  (verify)

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 

Adverse effects edit

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.[7][8] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[7][8]

Society and culture edit

Brand names edit

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.[9]

References edit

  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): 293–297. doi:10.1007/s10787-011-0103-7. PMID 22120888.
  4. ^ Fischer J, Ganellin CR (2010). Analogue-based Drug Discovery II. John Wiley & Sons. ISBN 9783527632121.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 520. ISBN 9783527607495.
  6. ^ Approved Drug Products with Therapeutic Equivalence Evaluations (PDF) (36th ed.). FDA. 2014.
  7. ^ a b "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.
  8. ^ a b "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.
  9. ^ "Flurbiprofen - International Brand Names". Drugs.com. Retrieved 14 November 2016.

Further reading edit


 

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April 11, 2024
flurbiprofen, member, phenylalkanoic, acid, derivative, family, nonsteroidal, anti, inflammatory, drugs, nsaids, primarily, indicated, operative, anti, miotic, ophthalmic, solution, well, orally, arthritis, dental, pain, side, effects, analogous, those, ibupro. 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 FlurbiprofenClinical dataTrade namesAnsaid Ocufen StrepfenOther names 2 fluoro a methyl 1 1 biphenyl 4 acetic acidAHFS Drugs comMonographMedlinePlusa687005PregnancycategoryAU B2Routes ofadministrationBy mouthATC codeM01AE09 WHO M02AA19 WHO R02AX01 WHO S01BC04 WHO Legal statusLegal statusAU S2 Pharmacy medicine S4 CA only US WARNING 1 Pharmacokinetic dataProtein binding gt 99 MetabolismLiver CYP2C9 Elimination half life4 7 5 7 hoursExcretionKidneyIdentifiersIUPAC name RS 2 2 fluorobiphenyl 4 yl propanoic acidCAS Number5104 49 4 YPubChem CID3394IUPHAR BPS4194DrugBankDB00712 YChemSpider3277 YUNII5GRO578KLPKEGGD00330 YChEBICHEBI 5130 YChEMBLChEMBL563 YPDB ligandFLP PDBe RCSB PDB CompTox Dashboard EPA DTXSID0037231ECHA InfoCard100 023 479Chemical and physical dataFormulaC 15H 13F O 2Molar mass244 265 g mol 13D model JSmol Interactive imageChiralityRacemic mixtureMelting point117 C 243 F SMILES Fc2cc ccc2c1ccccc1 C C O O CInChI 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 YKey SYTBZMRGLBWNTM UHFFFAOYSA N Y verify 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 Contents 1 Adverse effects 2 Society and culture 2 1 Brand names 3 References 4 Further readingAdverse effects editIn 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 7 8 They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy 7 8 Society and culture editBrand names edit 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 Flurbiprofene 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 9 References edit 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 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 amp Sons ISBN 9783527632121 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 520 ISBN 9783527607495 Approved Drug Products with Therapeutic Equivalence Evaluations PDF 36th ed FDA 2014 a b 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 nbsp This article incorporates text from this source which is in the public domain a b NSAIDs may cause rare kidney problems in unborn babies U S Food and Drug Administration 21 July 2017 Retrieved 15 October 2020 nbsp This article incorporates text from this source which is in the public domain Flurbiprofen International Brand Names Drugs com Retrieved 14 November 2016 Further reading editDean 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 Portal nbsp Medicine nbsp This drug article relating to the respiratory system is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the musculoskeletal system is a stub You can help Wikipedia by expanding it vte nbsp This analgesic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Flurbiprofen amp oldid 1204969628, wikipedia, wiki, book, books, library,

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