Fenbufen

Fenbufen is a nonsteroidal anti-inflammatory drug used to treat pain.^[1]

Fenbufen

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	M01AE05 (WHO)
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	36330-85-5^Y
PubChem CID	3335
DrugBank	DB08981^Y
ChemSpider	3218^Y
UNII	9815R1WR9B
KEGG	D01344^Y
ChEBI	CHEBI:31599^Y
ChEMBL	ChEMBL277522^Y
CompTox Dashboard (EPA)	DTXSID9023043
ECHA InfoCard	100.048.148
Chemical and physical data
Formula	C16H14O3
Molar mass	254.285 g·mol^−1
3D model (JSmol)	Interactive image
Melting point	186 °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)^Y Key:ZPAKPRAICRBAOD-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.^{[3][4]: 370, 383–384}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 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.