Misplaced Pages

Fenbufen

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Nonsteroidal anti-inflammatory drug, now withdrawn Pharmaceutical compound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
  • UK: POM (Prescription only)
Identifiers
IUPAC name
  • 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
3D model (JSmol)
Melting point186 °C (367 °F)
SMILES
  • O=C(O)CCC(=O)c2ccc(c1ccccc1)cc2
InChI
  • 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)
  • Key:ZPAKPRAICRBAOD-UHFFFAOYSA-N
  (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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.

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.
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
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.
Prostanoid signaling modulators
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 (F2α)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 synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators

Stub icon

This drug article relating to the musculoskeletal system is a stub. You can help Misplaced Pages by expanding it.

Categories: