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

Molecular Formula	C16H14O3
Molecular Weight	254.2806
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 Fenbufen was found to cause skin rash and liver toxicity and was withdrawn from the market.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Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/800381	Palliative		Withdrawn	Unknown Approved Use Unknown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
Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.	1991 Jun	1651287
[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
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
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
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
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
Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.	2005 Jan 10	15659296
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
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction?	2007 May	17518513
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
Combining a solution-phase derived library with in-situ cellular bioassay: prompt screening of amide-forming minilibraries using MTT assay.	2009 Jul	19571417
Differences in the interaction between aryl propionic acid derivatives and poly(vinylpyrrolidone) K30: A multi-methodological approach.	2009 Nov	19645003
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

Patents

Sample Use Guides

In Vivo Use Guide

900 mg daily

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:23 UTC 2023` Edited by `admin` on `Fri Dec 15 15:25:23 UTC 2023`
Record UNII	9815R1WR9B
Record Status	`Validated (UNII)`
Record Version

Download

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