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Fenbufen

From Wikipedia, the free encyclopedia
Nonsteroidal anti-inflammatory drug, now withdrawn
Pharmaceutical compound
Fenbufen
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
  • 4-(4-Biphenylyl)-4-oxobutanoic acid
    or
    4-Oxo-4-(4-phenylphenyl)butanoic acid
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.048.148Edit 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 anonsteroidal anti-inflammatory drug used to treat pain.[1]

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

It was introduced byAmerican Cyanamid under the trade nameLederfen 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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.[3][4]: 370, 383–384 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

[edit]

Fenbufen can be synthesized by acylation ofbiphenyl withsuccinic anhydride underFriedel-Crafts conditions.[6]

References

[edit]
  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. Retrieved25 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.
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others

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