Chemistry:Fenbufen

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Short description: Nonsteroidal anti-inflammatory drug, now withdrawn
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC16H14O3
Molar mass254.285 g·mol−1
3D model (JSmol)
Melting point186 °C (367 °F)
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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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.[3][4]:370, 383-384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. "Single dose oral fenbufen for acute postoperative pain in adults". The Cochrane Database of Systematic Reviews 2009 (4): CD007547. October 2009. doi:10.1002/14651858.CD007547.pub2. PMID 19821427. 
  2. "Non-steroidal anti-inflammatory analgesics other than salicylates". Drugs 32 (Suppl 4): 27–45. 1986. doi:10.2165/00003495-198600324-00004. PMID 3552584. 
  3. "Deleted products 2010". Monthly Index of Medical Specialities (MIMS). Haymarket Media Group Ltd.. http://www.mims.co.uk/deleted-products-2010/article/978347. 
  4. "Nonsteroidal Antiinflammatory Drugs and Leukotriene Receptor Antagonists. Chapter 22". Drug-Induced Liver Disease (3rd ed.). Academic Press. 2013. ISBN 978-0-12-387818-2. 
  5. "International listings for fenbufen". Drugs.com. https://www.drugs.com/international/fenbufen.html. 
  6. "An Improved Synthesis of Fenbulen". Organic Preparations and Procedures International 27 (5): 550–552. October 1995. doi:10.1080/00304949509458497.