FENBUFEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14O3
Molecular Weight	254.2806
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCC(=O)C1=CC=C(C=C1)C2=CC=CC=C2

InChI

InChIKey=ZPAKPRAICRBAOD-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: www.ncbi.nlm.nih.gov/pubmed/6356910
Curator's Comment: description was created based on several sources, including, http://scialert.net/fulltext/?doi=ajb.2007.50.57

Fenbufen is a nonsteroidal anti-inflammatory drug, developed for the treatment of symptoms associated with such disease as rheumatoid arthritis. Fenbufen acts through its active metabolite, 4-biphenylacetic acid which is a potent inhibitor of COX1 and COX2 enzymes. Fenbufen was found to cause skin rash and liver toxicity and was withdrawn from the market.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 1 30 Target ID: P23219\|\|\|Q5T7T7 Gene ID: 5742.0 Gene Symbol: PTGS1 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/6356910	Inhibitor 8297		3.9 µM [IC50]
Prostaglandin G/H synthase 2 48 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/6356910	Inhibitor 8297		8.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/800381	Palliative		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Aplastic anaemia associated with a non-steroidal anti-inflammatory drug: relapse after exposure to another such drug.	1990 Jul 7	2383708
Assessment of temafloxacin neurotoxicity in rodents.	1991 Dec 30	1662895
Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.	1991 Jun	1651287
Interaction of the new quinolone antibacterial agent levofloxacin with fenbufen in mice.	1992 Mar	1622442
[Effects of drugs on the convulsions induced by the combination of a new quinolone antimicrobial, enoxacin, and a nonsteroidal anti-inflammatory drug, fenbufen, in mice].	1992 Oct	1446880
Circadian variation in enoxacin-induced convulsions in mice coadministered with fenbufen.	1997 Feb	9074952
Role of nitric oxide in the convulsions following the coadministration of enoxacin with fenbufen in mice.	1998 Apr	9623721
Determination of nonsteroidal anti-inflammatory drugs in biological fluids by automatic on-line integration of solid-phase extraction and capillary electrophoresis.	2001 Feb	11258759
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation.	2001 May-Jun	11386636
[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].	2003 Aug	14567251
Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system.	2003 Feb	12696183
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.	2003 Jun 2	12771981
The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes.	2003 Jun 5	12791169
Practical synthesis of fenbufen ethanolamide.	2004 Oct	15476286
1H-NMR study of the inclusion processes for alpha- and gamma-cyclodextrin with fenbufen.	2005 Apr 15	15690411
In-tube solid phase microextraction using a beta-cyclodextrin coated capillary coupled to high performance liquid chromatography for determination of non-steroidal anti-inflammatory drugs in urine samples.	2005 Jan 15	18969772
Applications of derivative UV spectrophotometry for the determinations of fenbufen and ketoprofen in pharmaceutical preparations.	2005 May-Jun	16193808
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.	2005 Nov 29	16316472
Changes in brain interleukin-1beta following the coadministration of norfloxacin with biphenylacetic acid in rats.	2006 Aug 14	16824509
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.	2007 Dec	19305740
6-aryl-4-oxohexanoic acids: synthesis, effects on eicosanoid biosynthesis, and anti-inflammatory in vivo-activities.	2007 Sep	17897067
Ionic liquid-based dynamic liquid-phase microextraction: application to the determination of anti-inflammatory drugs in urine samples.	2008 Aug 15	18632109
Combination of solid-phase extraction and large-volume stacking with polarity switching in micellar electrokinetic capillary chromatography for the determination of traces of nonsteroidal anti-inflammatory drugs in saliva.	2008 Jul	18655057
Thermodynamic studies of Fenbufen, Diflunisal, and Flurbiprofen: sublimation, solution and solvation of biphenyl substituted drugs.	2008 Jun 5	18343061
A seizure attributed to ofloxacine in a woman undergoing detoxification for alcohol dependence.	2009	20145722
Effects of nonsteroidal anti-inflammatory drugs on the expression and function of P-glycoprotein/MDR1 in Caco-2 cells.	2009	19793025
Phenylacetic acids and the structurally related non-steroidal anti-inflammatory drug diclofenac bind to specific gamma-hydroxybutyric acid sites in rat brain.	2009 Apr	19645815
Combining a solution-phase derived library with in-situ cellular bioassay: prompt screening of amide-forming minilibraries using MTT assay.	2009 Jul	19571417
Photoreactivity of biologically active compounds. XIX: excited states and free radicals from the antimalarial drug primaquine.	2009 Mar 3	19114311
In vitro genotoxic assessment of xenobiotic diacylglycerols in an in vitro micronucleus assay.	2009 May	19177498
Differences in the interaction between aryl propionic acid derivatives and poly(vinylpyrrolidone) K30: A multi-methodological approach.	2009 Nov	19645003
Single dose oral fenbufen for acute postoperative pain in adults.	2009 Oct 7	19821427
Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents.	2009 Sep	19457595
Risk of Upper Gastrointestinal Bleeding in a Cohort of New Users of Low-Dose ASA for Secondary Prevention of Cardiovascular Outcomes.	2010	21811460
Inclusion and release of fenbufen in mesoporous silica.	2010 Aug	20232455
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Synthesis and structure-activity relationships of fenbufen amide analogs.	2010 Dec 2	21127465
Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori.	2010 Mar 21	20200713
Influence of relative humidity on the interaction between different aryl propionic acid derivatives and poly(vinylpyrrolydone) K30: evaluation of the effect on drug bioavailability.	2010 Oct 15	20655373

Patents

Sample Use Guides

In Vivo Use Guide

900 mg daily

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

FENBUFEN

Official Name

English

FENBUFEN [EP MONOGRAPH]

Common Name

English

Fenbufen [WHO-DD]

Common Name

English

(1,1'-BIPHENYL)-4-BUTANOIC ACID, .GAMMA.-OXO-

Common Name

English

FENBUFEN [MI]

Common Name

English

CL-82204

Code

English

FENBUFEN [MART.]

Common Name

English

FENBUFEN [JAN]

Common Name

English

3-(4-Biphenylylcarbonyl)propionic acid

Systematic Name

English

CL 82,204

Code

English

FENBUFEN [USAN]

Common Name

English

NSC-757812

Code

English

fenbufen [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257