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 Fenbufen was found to cause skin rash and liver toxicity and was withdrawn from the market.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Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/800381	Palliative		Withdrawn	Unknown Approved Use Unknown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
Assessment of temafloxacin neurotoxicity in rodents.	1991 Dec 30	1662895
[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
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
[Colitis enhances the colorectal carcinogenesis in rats: correlation between the incidence of aberrant crypt foci and the incidence of tumors].	2001 May	11400280
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
Evaluation of the malignant potential of aberrant crypt foci by immunohistochemical staining for beta-catenin in inflammation-induced rat colon carcinogenesis.	2002 Apr	11891526
Syntheses and reactions of some new 2-arylidene-4-(biphenyl-4-yl)-but-3-en-4-olides with a study of their biological activity.	2002 Jul	12168522
[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
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.	2004 Aug 2	15226764
In vitro reactivity of carboxylic acid-CoA thioesters with glutathione.	2004 Jan	14727921
Inclusion complex of fenbufen with beta-cyclodextrin.	2004 Mar	14991662
Practical synthesis of fenbufen ethanolamide.	2004 Oct	15476286
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
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.	2005 Nov 29	16316472
Antioxidant activity and inhibition of human neutrophil oxidative burst mediated by arylpropionic acid non-steroidal anti-inflammatory drugs.	2006 Aug	16880623
Changes in brain interleukin-1beta following the coadministration of norfloxacin with biphenylacetic acid in rats.	2006 Aug 14	16824509
Contribution of solid-state properties to the aqueous solubility of drugs.	2006 Nov	16949802
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
Effects of nonsteroidal anti-inflammatory drugs on the expression and function of P-glycoprotein/MDR1 in Caco-2 cells.	2009	19793025
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
Risk of Upper Gastrointestinal Bleeding in a Cohort of New Users of Low-Dose ASA for Secondary Prevention of Cardiovascular Outcomes.	2010	21811460
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443

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