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Identification
Name Fenoprofen
Accession Number DB00573 (APRD00970)
Type small molecule
Groups approved
Description

An anti-inflammatory analgesic and antipyretic highly bound to plasma proteins. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Feneprofen calcium salt dihydrate
  • Fenoprofen calcium
  • Fenoprofen calcium hydrate
Brand names
  • Nalfon
Brand name mixtures Not Available
Categories
  • Cyclooxygenase Inhibitors
  • Propionic acid derivatives
CAS number 34597-40-5
Weight Average: 242.2699
Monoisotopic: 242.094294314
Chemical Formula C15H14O3
InChI Key InChIKey=RDJGLLICXDHJDY-UHFFFAOYSA-N
InChI
InChI=1S/C15H14O3/c1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13/h2-11H,1H3,(H,16,17)
Plain Text
IUPAC Name
2-(3-phenoxyphenyl)propanoic acid
SMILES
CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
Substructures
  • Hydroxy Compounds
  • Acetates
  • Phenols and Derivatives
  • Carboxylic Acids and Derivatives
  • Phenylacetates
  • Ethers
  • Benzene and Derivatives
  • Aromatic compounds
  • Anisoles
  • Phenyl Esters
Pharmacology
Indication For relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.
Pharmacodynamics Fenoprofen is a propionic acid derivative with analgesic, antiinflammatory and antipyretic properties. Fenoprofen inhibits prostaglandin synthesis by decreasing the enzyme needed for biosynthesis. In patients with rheumatoid arthritis, the anti-inflammatory action of fenoprofen has been evidenced by relief of pain, increase in grip strength, and reductions in joint swelling, duration of morning stiffness, and disease activity (as assessed by both the investigator and the patient). In patients with osteoarthritis, the anti-inflammatory and analgesic effects of fenoprofen have been demonstrated by reduction in tenderness as a response to pressure and reductions in night pain, stiffness, swelling, and overall disease activity (as assessed by both the patient and the investigator). These effects have also been demonstrated by relief of pain with motion and at rest and increased range of motion in involved joints. In patients with rheumatoid arthritis and osteoarthritis, clinical studies have shown fenoprofen to be comparable to aspirin in controlling the aforementioned measures of disease activity, but mild gastrointestinal reactions (nausea, dyspepsia) and tinnitus occurred less frequently in patients treated with fenoprofen than in aspirin-treated patients. It is not known whether fenoprofen causes less peptic ulceration than does aspirin. In patients with pain, the analgesic action of fenoprofen has produced a reduction in pain intensity, an increase in pain relief, improvement in total analgesia scores, and a sustained analgesic effect.
Mechanism of action Fenoprofen's exact mode of action is unknown, but it is thought that prostaglandin synthetase inhibition is involved. Fenoprofen has been shown to inhibit prostaglandin synthetase isolated from bovine seminal vesicles.
Absorption Rapidly absorbed under fasting conditions, and peak plasma levels of 50 µg/mL are achieved within 2 hours after oral administration of 600 mg doses.
Volume of distribution Not Available
Protein binding 99% to albumin.
Metabolism

About 90% of a single oral dose is eliminated within 24 hours as fenoprofen glucuronide and 4'-hydroxyfenoprofen glucuronide, the major urinary metabolites of fenoprofen.
Route of elimination Not Available
Half life Plasma half-life is approximately 3 hours.
Clearance Not Available
Toxicity Symptoms of overdose appear within several hours and generally involve the gastrointestinal and central nervous systems. They include dyspepsia, nausea, vomiting, abdominal pain, dizziness, headache, ataxia, tinnitus, tremor, drowsiness, and confusion. Hyperpyrexia, tachycardia, hypotension, and acute renal failure may occur rarely following overdose. Respiratory depression and metabolic acidosis have also been reported following overdose with certain NSAIDs.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • American therapeutics inc
  • Halsey drug co inc
  • Par pharmaceutical inc
  • Quantum pharmics ltd
  • Sandoz inc
  • Warner chilcott div warner lambert co
  • Watson laboratories inc
  • Pedinol pharmacal inc
  • Actavis elizabeth llc
  • Clonmel healthcare ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Usl pharma inc
  • Dista products co div eli lilly and co
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Prices
Unit description Cost Unit
Fenoprofen calcium powder 1.59 USD g
Fenoprofen Calcium 600 mg tablet 1.01 USD tablet
Nalfon 200 mg capsule 0.91 USD capsule
Fenoprofen 600 mg tablet 0.88 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Slight (calcium salt) PhysProp
logP 3.1 PhysProp
pKa 4.5 Various sources
Predicted Properties
Property Value Source
water solubility 8.11e-02 g/l ALOGPS
logP 3.87 ALOGPS
logP 3.65 ChemAxon Molconvert
logS -3.48 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 46.53 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 68.18 ChemAxon Molconvert
polarizability 25.30 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00968 Link_out
PubChem Compound 3342 Link_out
PubChem Substance 46504597 Link_out
ChemSpider 3225 Link_out
ChEBI 5004 Link_out
ChEMBL 5004 Link_out
Therapeutic Targets Database DAP000619 Link_out
PharmGKB PA449598 Link_out
Drug Product Database 345504 Link_out
RxList http://www.rxlist.com/cgi/generic2/fenoprofen.htm Link_out
Drugs.com http://www.drugs.com/cdi/fenoprofen.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Fenoprofen Link_out
ATC Codes
  • M01AE04
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (140.8 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.
Targets

1. Prostaglandin G/H synthase 2

Pharmacological action: yes
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Poggi JC, Barissa GR, Donadi EA, Foss MC, Cunha FQ, Lanchote VL, dos Reis ML: Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus. J Clin Pharmacol. 2006 Nov;46(11):1328-36. Pubmed

2. Prostaglandin G/H synthase 1

Pharmacological action: unknown
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Poggi JC, Barissa GR, Donadi EA, Foss MC, Cunha FQ, Lanchote VL, dos Reis ML: Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus. J Clin Pharmacol. 2006 Nov;46(11):1328-36. Pubmed
Carriers

1. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.