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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 of FENBUFEN

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 Fenbufen was found to cause skin rash and liver toxicity and was withdrawn from the market.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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin G/H synthase 1
30
Target ID: P23219|||Q5T7T7
Gene ID: 5742.0
Gene Symbol: PTGS1
Target Organism: Homo sapiens (Human)
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)
Inhibitor
8504
 8.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Withdrawn
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Aplastic anaemia associated with a non-steroidal anti-inflammatory drug: relapse after exposure to another such drug.
1990 Jul 7
Assessment of temafloxacin neurotoxicity in rodents.
1991 Dec 30
Hippocampus and frontal cortex are the potential mediatory sites for convulsions induced by new quinolones and non-steroidal anti-inflammatory drugs.
1991 Jun
Interaction of the new quinolone antibacterial agent levofloxacin with fenbufen in mice.
1992 Mar
[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
Circadian variation in enoxacin-induced convulsions in mice coadministered with fenbufen.
1997 Feb
Role of nitric oxide in the convulsions following the coadministration of enoxacin with fenbufen in mice.
1998 Apr
[Colitis enhances the colorectal carcinogenesis in rats: correlation between the incidence of aberrant crypt foci and the incidence of tumors].
2001 May
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
Evaluation of the malignant potential of aberrant crypt foci by immunohistochemical staining for beta-catenin in inflammation-induced rat colon carcinogenesis.
2002 Apr
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
[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].
2003 Aug
Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system.
2003 Feb
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.
2003 Jun 2
The stereospecificity of flobufen metabolism in isolated guinea pig hepatocytes.
2003 Jun 5
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.
2004 Aug 2
Enteric-coated layered double hydroxides as a controlled release drug delivery system.
2004 Dec 9
In vitro reactivity of carboxylic acid-CoA thioesters with glutathione.
2004 Jan
Inclusion complex of fenbufen with beta-cyclodextrin.
2004 Mar
Practical synthesis of fenbufen ethanolamide.
2004 Oct
1H-NMR study of the inclusion processes for alpha- and gamma-cyclodextrin with fenbufen.
2005 Apr 15
Celecoxib does not induce convulsions nor does it affect GABAA receptor binding activity in the presence of new quinolones in mice.
2005 Jan 10
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
Applications of derivative UV spectrophotometry for the determinations of fenbufen and ketoprofen in pharmaceutical preparations.
2005 May-Jun
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.
2005 Nov 29
Determination of dissociation constants of cyclodextrin-ligand inclusion complexes by electrospray ionization mass spectrometry.
2006
Antioxidant activity and inhibition of human neutrophil oxidative burst mediated by arylpropionic acid non-steroidal anti-inflammatory drugs.
2006 Aug
Changes in brain interleukin-1beta following the coadministration of norfloxacin with biphenylacetic acid in rats.
2006 Aug 14
Contribution of solid-state properties to the aqueous solubility of drugs.
2006 Nov
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.
2007 Dec
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction?
2007 May
6-aryl-4-oxohexanoic acids: synthesis, effects on eicosanoid biosynthesis, and anti-inflammatory in vivo-activities.
2007 Sep
Ionic liquid-based dynamic liquid-phase microextraction: application to the determination of anti-inflammatory drugs in urine samples.
2008 Aug 15
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
Thermodynamic studies of Fenbufen, Diflunisal, and Flurbiprofen: sublimation, solution and solvation of biphenyl substituted drugs.
2008 Jun 5
A seizure attributed to ofloxacine in a woman undergoing detoxification for alcohol dependence.
2009
Effects of nonsteroidal anti-inflammatory drugs on the expression and function of P-glycoprotein/MDR1 in Caco-2 cells.
2009
Phenylacetic acids and the structurally related non-steroidal anti-inflammatory drug diclofenac bind to specific gamma-hydroxybutyric acid sites in rat brain.
2009 Apr
Combining a solution-phase derived library with in-situ cellular bioassay: prompt screening of amide-forming minilibraries using MTT assay.
2009 Jul
Photoreactivity of biologically active compounds. XIX: excited states and free radicals from the antimalarial drug primaquine.
2009 Mar 3
In vitro genotoxic assessment of xenobiotic diacylglycerols in an in vitro micronucleus assay.
2009 May
Differences in the interaction between aryl propionic acid derivatives and poly(vinylpyrrolidone) K30: A multi-methodological approach.
2009 Nov
Single dose oral fenbufen for acute postoperative pain in adults.
2009 Oct 7
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
Risk of Upper Gastrointestinal Bleeding in a Cohort of New Users of Low-Dose ASA for Secondary Prevention of Cardiovascular Outcomes.
2010
Inclusion and release of fenbufen in mesoporous silica.
2010 Aug
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Synthesis and structure-activity relationships of fenbufen amide analogs.
2010 Dec 2
Bismuth(III) complexes derived from non-steroidal anti-inflammatory drugs and their activity against Helicobacter pylori.
2010 Mar 21
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
Patents

Patents

04014907
1
JP2006524634A
46
JPS61254521A
1

Sample Use Guides

In Vivo Use Guide
900 mg daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
FENBUFEN
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
WHO-ATC M01AE05
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
WHO-VATC QM01AE05
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID9023043
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL277522
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
CHEBI
31599
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
MERCK INDEX
m5266
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY Merck Index
CAS
36330-85-5
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
SMS_ID
100000081264
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
FDA UNII
9815R1WR9B
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
DRUG CENTRAL
1145
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
EVMPD
SUB07543MIG
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
MESH
C010725
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
NSC
757812
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
INN
3439
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
DRUG BANK
DB08981
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
WIKIPEDIA
Fenbufen
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
PUBCHEM
3335
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
ECHA (EC/EINECS)
252-979-0
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
RXCUI
24830
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C80548
Created by admin on Mon Mar 31 17:57:09 GMT 2025 , Edited by admin on Mon Mar 31 17:57:09 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of FENBUFEN
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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