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 Fenbufen was found to cause skin rash and liver toxicity and was withdrawn from the market.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 8504		3.9 µM [IC50]
Prostaglandin G/H synthase 2 51 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 8504		8.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/800381	Palliative		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis and structure-activity relationships of fenbufen amide analogs.	2010-12-02	21127465
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Influence of relative humidity on the interaction between different aryl propionic acid derivatives and poly(vinylpyrrolydone) K30: evaluation of the effect on drug bioavailability.	2010-10-15	20655373
Inclusion and release of fenbufen in mesoporous silica.	2010-08	20232455
Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori.	2010-03-21	20200713
Risk of Upper Gastrointestinal Bleeding in a Cohort of New Users of Low-Dose ASA for Secondary Prevention of Cardiovascular Outcomes.	2010	21811460
Differences in the interaction between aryl propionic acid derivatives and poly(vinylpyrrolidone) K30: A multi-methodological approach.	2009-11	19645003
Single dose oral fenbufen for acute postoperative pain in adults.	2009-10-07	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.	2009-09	19457595
Combining a solution-phase derived library with in-situ cellular bioassay: prompt screening of amide-forming minilibraries using MTT assay.	2009-07	19571417
In vitro genotoxic assessment of xenobiotic diacylglycerols in an in vitro micronucleus assay.	2009-05	19177498
Phenylacetic acids and the structurally related non-steroidal anti-inflammatory drug diclofenac bind to specific gamma-hydroxybutyric acid sites in rat brain.	2009-04	19645815
Photoreactivity of biologically active compounds. XIX: excited states and free radicals from the antimalarial drug primaquine.	2009-03-03	19114311
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
Ionic liquid-based dynamic liquid-phase microextraction: application to the determination of anti-inflammatory drugs in urine samples.	2008-08-15	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.	2008-07	18655057
Thermodynamic studies of Fenbufen, Diflunisal, and Flurbiprofen: sublimation, solution and solvation of biphenyl substituted drugs.	2008-06-05	18343061
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.	2007-12	19305740
6-aryl-4-oxohexanoic acids: synthesis, effects on eicosanoid biosynthesis, and anti-inflammatory in vivo-activities.	2007-09	17897067
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction?	2007-05	17518513
Contribution of solid-state properties to the aqueous solubility of drugs.	2006-11	16949802
Changes in brain interleukin-1beta following the coadministration of norfloxacin with biphenylacetic acid in rats.	2006-08-14	16824509
Antioxidant activity and inhibition of human neutrophil oxidative burst mediated by arylpropionic acid non-steroidal anti-inflammatory drugs.	2006-08	16880623
Determination of dissociation constants of cyclodextrin-ligand inclusion complexes by electrospray ionization mass spectrometry.	2006	17404419
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.	2005-11-29	16316472
Applications of derivative UV spectrophotometry for the determinations of fenbufen and ketoprofen in pharmaceutical preparations.	2005-10-01	16193808
1H-NMR study of the inclusion processes for alpha- and gamma-cyclodextrin with fenbufen.	2005-04-15	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.	2005-01-15	18969772
Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.	2005-01-10	15659296
Enteric-coated layered double hydroxides as a controlled release drug delivery system.	2004-12-09	15541916
Practical synthesis of fenbufen ethanolamide.	2004-10	15476286
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.	2004-08-02	15226764
Inclusion complex of fenbufen with beta-cyclodextrin.	2004-03	14991662
In vitro reactivity of carboxylic acid-CoA thioesters with glutathione.	2004-01	14727921
[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].	2003-08	14567251
The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes.	2003-06-05	12791169
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.	2003-06-02	12771981
Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system.	2003-02	12696183
Syntheses and reactions of some new 2-arylidene-4-(biphenyl-4-yl)-but-3-en-4-olides with a study of their biological activity.	2002-07	12168522
Evaluation of the malignant potential of aberrant crypt foci by immunohistochemical staining for beta-catenin in inflammation-induced rat colon carcinogenesis.	2002-04	11891526
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.	2001-06-02	11386636
[Colitis enhances the colorectal carcinogenesis in rats: correlation between the incidence of aberrant crypt foci and the incidence of tumors].	2001-05	11400280
Role of nitric oxide in the convulsions following the coadministration of enoxacin with fenbufen in mice.	1998-04	9623721
Circadian variation in enoxacin-induced convulsions in mice coadministered with fenbufen.	1997-02	9074952
[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].	1992-10	1446880
Interaction of the new quinolone antibacterial agent levofloxacin with fenbufen in mice.	1992-03	1622442
Assessment of temafloxacin neurotoxicity in rodents.	1991-12-30	1662895
Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.	1991-06	1651287
Aplastic anaemia associated with a non-steroidal anti-inflammatory drug: relapse after exposure to another such drug.	1990-07-07	2383708

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 `Mon Mar 31 17:57:09 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:09 GMT 2025`
Record UNII	9815R1WR9B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENBUFEN

Official Name

English

CL 82,204

Preferred 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

FENBUFEN [USAN]

Common Name

English

NSC-757812

Code

English

fenbufen [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257