Fenbufen

Identification

Name
Fenbufen
Accession Number
DB08981
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
3D
Similar Structures
Synonyms
  • 3-(4-Biphenylylcarbonyl)propionic acid
  • 3-(4-Phenylbenzoyl)propionic acid
  • 4-(4-Biphenylyl)-4-oxobutyric acid
  • 4-Biphenyl-4-yl-4-oxobutanoic acid
  • Fenbufen
  • gamma-oxo(1,1'-Biphenyl)-4-butanoic acid
External IDs
CL 82,204
Categories
UNII
9815R1WR9B
CAS number
36330-85-5
Weight
Average: 254.2806
Monoisotopic: 254.094294314
Chemical Formula
C16H14O3
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Fenbufen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Fenbufen is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fenbufen is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Fenbufen.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Fenbufen.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Fenbufen is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of hypertension can be increased when 3,4-Methylenedioxyamphetamine is combined with Fenbufen.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Fenbufen.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Fenbufen is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Fenbufen.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,784,701.

General References
Not Available
External Links
KEGG Drug
D01344
PubChem Compound
3335
PubChem Substance
310264942
ChemSpider
3218
BindingDB
50240374
ChEBI
31599
ChEMBL
CHEMBL277522
PharmGKB
PA166049176
Wikipedia
Fenbufen
ATC Codes
M01AE05 — Fenbufen

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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 / Biphenyl / Butyrophenone / Aryl alkyl ketone / Gamma-keto acid / Benzoyl / Benzenoid / Keto acid / Monocyclic benzene moiety / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
biphenyls, 4-oxo monocarboxylic acid (CHEBI:31599)

Drug created on June 10, 2014 09:46 / Updated on November 02, 2018 06:56