Fenbufen

Last updated
Fenbufen
Fenbufen.svg
Fenbufen-from-xtal-1988-3D-balls.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Identifiers
  • 4-(4-Biphenylyl)-4-oxobutanoic acid
    or
    4-Oxo-4-(4-phenylphenyl)butanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.048.148 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H14O3
Molar mass 254.285 g·mol−1
3D model (JSmol)
Melting point 186 °C (367 °F)
  • O=C(O)CCC(=O)c2ccc(c1ccccc1)cc2
  • InChI=1S/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19) Yes check.svgY
  • Key:ZPAKPRAICRBAOD-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Fenbufen is a nonsteroidal anti-inflammatory drug used to treat pain. [1]

Fenbufen is a member of the propionic acid derivatives class of drugs. [2]

It was introduced by American Cyanamid under the trade name Lederfen in the 1980s. Due to liver toxicity, it was withdrawn from markets in the developed world in 2010. [3] [4] : 370, 383–384 

As of 2015 it was available in Taiwan and Thailand under several brand names. [5]

Preparation

Fenbufen can be synthesized by acylation of biphenyl with succinic anhydride under Friedel-Crafts conditions. [6]

References

  1. ↑ Moore RA, Derry S, McQuay HJ (October 2009). "Single dose oral fenbufen for acute postoperative pain in adults". The Cochrane Database of Systematic Reviews. 2009 (4) CD007547. doi:10.1002/14651858.CD007547.pub2. PMC   4175557 . PMID   19821427.
  2. ↑ Brogden RN (1986). "Non-steroidal anti-inflammatory analgesics other than salicylates". Drugs. 32 (Suppl 4): 27–45. doi:10.2165/00003495-198600324-00004. PMID   3552584. S2CID   25471102.
  3. ↑ "Deleted products 2010". Monthly Index of Medical Specialities (MIMS). Haymarket Media Group Ltd.
  4. ↑ Lewis JH, Stine JG (2013). "Nonsteroidal Antiinflammatory Drugs and Leukotriene Receptor Antagonists. Chapter 22". In Kaplowitz N, DeLeve LD (eds.). Drug-Induced Liver Disease (3rd ed.). Academic Press. ISBN   978-0-12-387818-2.
  5. ↑ "International listings for fenbufen". Drugs.com. Retrieved 25 June 2015.
  6. ↑ Castillo R, Suárez-Herrera M, Aparicio M, Hernández-Lui F, Hernández A (October 1995). "An Improved Synthesis of Fenbulen". Organic Preparations and Procedures International. 27 (5): 550–552. doi:10.1080/00304949509458497.

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