Fenbufen

Identification

Generic Name
Fenbufen
DrugBank Accession Number
DB08981
Background

Fenbufen is a non-steroidal anti-inflammatory drug used primarily to treat inflammation in osteoarthritis, ankylosing spondylitis, and tendinitis. It can also be used to relieve backaches, sprains, and fractures. Fenbufen is available as a capsule or tablet sold with the brand names Cepal, Cinopal, Cybufen, Lederfen, and Reugast. Fenbufen acts by preventing cyclooxygenase from producing prostaglandins which can cause inflammation.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 254.2806
Monoisotopic: 254.094294314
Chemical Formula
C16H14O3
Synonyms
  • 3-(4-Biphenylylcarbonyl)propionic acid
  • 3-(4-Phenylbenzoyl)propionic acid
  • 4-(4-Biphenylyl)-4-oxobutyric acid
  • Fenbufen
  • Fenbufén
  • Fenbufène
  • Fenbufenum
  • gamma-oxo(1,1'-biphenyl)-4-butanoic acid
External IDs
  • CL 82,204
  • CL-82204

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirFenbufen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Fenbufen is combined with Abciximab.
AcebutololFenbufen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Fenbufen.
AcemetacinThe risk or severity of adverse effects can be increased when Fenbufen is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Fenbufen is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Fenbufen.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Fenbufen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Fenbufen.
AclidiniumFenbufen may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
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Food Interactions
Not Available

Products

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Categories

ATC Codes
M01AE05 — Fenbufen
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Biphenyls and derivatives / Butyrophenones / Gamma-keto acids and derivatives / Benzoyl derivatives / Aryl alkyl ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Alkyl-phenylketone / Aromatic homomonocyclic compound / Aryl alkyl ketone / Benzenoid / Benzoyl / Biphenyl / Butyrophenone / Carboxylic acid / Carboxylic acid derivative / Gamma-keto acid
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
biphenyls, 4-oxo monocarboxylic acid (CHEBI:31599)
Affected organisms
Not Available

Chemical Identifiers

UNII
9815R1WR9B
CAS number
36330-85-5
InChI Key
ZPAKPRAICRBAOD-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-oxo-4-(4-phenylphenyl)butanoic acid
SMILES
OC(=O)CCC(=O)C1=CC=C(C=C1)C1=CC=CC=C1

References

Synthesis Reference

U.S. Patent 3,784,701.

General References
Not Available
KEGG Drug
D01344
PubChem Compound
3335
PubChem Substance
310264942
ChemSpider
3218
BindingDB
50240374
RxNav
24830
ChEBI
31599
ChEMBL
CHEMBL277522
ZINC
ZINC000000001427
PharmGKB
PA166049176
Wikipedia
Fenbufen

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Capsule300 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)185-187U.S. Patent 3,784,701.
Predicted Properties
PropertyValueSource
Water Solubility0.0121 mg/mLALOGPS
logP3.07ALOGPS
logP3ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.49 m3·mol-1ChemAxon
Polarizability27.47 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f89-2900000000-b30afcea40626e90c194

Drug created on June 10, 2014 15:46 / Updated on June 12, 2020 16:52