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	C (U.S.), B2 (Au);
Routes of; administration	Oral
ATC code	M01AE09 (WHO) , M02AA19 (WHO), R02AX01 (WHO), S01BC04 (WHO);
Legal status
Legal status	US: WARNING; POD;
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	244.261 g/mol 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 non-steroidal 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.^[2] It is generic and is marketed under brand names worldwide, including "Ansaid" and "Froben".^[3]

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.^[4]^[5]^[6]^: 34

Side effects are analogous to those of ibuprofen. As of 2015 the cost for a typical month of medication in the United States is 50 to 100 USD.^[7]

References

^ "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.
^ Drugs.com Flurbiprofen listings at drugs.com Page accessed July 3, 2015
^ Halford, GM; Lordkipanidzé, M; Watson, SP (2012). "50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams". Platelets. 23 (6): 415–22. doi:10.3109/09537104.2011.632032. PMID 22098129.
^ Rainsford KD. Fifty years since the discovery of ibuprofen. Inflammopharmacology. 2011 Dec;19(6):293-7. PMID 22120888
^ Janos Fischer and C. Robin Ganellin. Analogue-based Drug Discovery II. John Wiley & Sons, 2010 ISBN 9783527632121
^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 8. ISBN 9781284057560.

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[FDA-AllBoxedWarnings-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] Drugs.com Flurbiprofen listings at drugs.com Page accessed July 3, 2015

[plat12-4] Halford, GM; Lordkipanidzé, M; Watson, SP (2012). "50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams". Platelets. 23 (6): 415–22. doi:10.3109/09537104.2011.632032. PMID 22098129.

[5] Rainsford KD. Fifty years since the discovery of ibuprofen. Inflammopharmacology. 2011 Dec;19(6):293-7. PMID 22120888

[6] Janos Fischer and C. Robin Ganellin. Analogue-based Drug Discovery II. John Wiley & Sons, 2010 ISBN 9783527632121

[Ric2015-7] Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 8. ISBN 9781284057560.

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v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal

v t e Throat preparations (R02)
Antiseptics	Acriflavinium chloride Ambazone Amylmetacresol Benzalkonium Benzethonium Cetrimonium (bromide/chloride) Cetylpyridinium Chlorhexidine Chlorquinaldol Dequalinium Dichlorobenzyl alcohol Hexamidine Hexetidine Hexylresorcinol Myristyl-benzalkonium Oxyquinoline Phenol Povidone-iodine
Antibiotics	Bacitracin Fusafungine Gramicidin Neomycin Tyrothricin
Local anesthetics	Benzocaine Cocaine Dyclonine Lidocaine
Other	Flurbiprofen