Fenbufen
Fenbufen.svg
Fenbufen-from-xtal-1988-3D-balls.png
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
 ☒NcheckY (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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.[3][4]: 370, 383–384 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, R. A.; Derry, S.; McQuay, H. J. (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.
  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, Rafael; Suárez-Herrera, Margarita; Aparicio, Mayra; Hernández-Lui, Francisco; Hernández, Alicia (1995). "An Improved Synthesis of Fenbulen". Organic Preparations and Procedures International. 27 (5): 550–552. doi:10.1080/00304949509458497.


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