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 254.2854 g·mol−1
3D model (JSmol)
  • 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
Properties
Melting point 186 °C (367 °F; 459 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.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]

Related Research Articles

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<span class="mw-page-title-main">Mofezolac</span>

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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.