Fenbufen

Fenbufen
Clinical data
AHFS/Drugs.comInternational 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 InfoCard100.048.148 Edit this at Wikidata
Chemical and physical data
FormulaC16H14O3
Molar mass254.285 g·mol−1
3D model (JSmol)
Melting point186 °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) checkY
  • Key:ZPAKPRAICRBAOD-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

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

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

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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.: 370, 383–384 

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

Preparation

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

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.