THC Science

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 ;
PubChem CID	3335;
DrugBank	DB08981 ;
ChemSpider	3218 ;
UNII	9815R1WR9B;
KEGG	D01344 ;
ChEBI	CHEBI:31599 ;
ChEMBL	ChEMBL277522 ;
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) ; Key:ZPAKPRAICRBAOD-UHFFFAOYSA-N ;
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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 Due to liver toxicity, it was withdrawn from markets in the developed world in 2010.^[3]^[4]^{: 370, 383–384}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[edit]

Fenbufen can be synthesized by acylation of biphenyl with succinic anhydride under Friedel-Crafts conditions.^[6]

References[edit]

^ 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.
^ 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.
^ "Deleted products 2010". Monthly Index of Medical Specialities (MIMS). Haymarket Media Group Ltd.
^ 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.
^ "International listings for fenbufen". Drugs.com. Retrieved 25 June 2015.
^ 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.

[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.

[pmid3552584-2] 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.

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Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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References[edit]

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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
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