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
Synonyms
  • (+-)-2-(3-Phenoxyphenyl)propionic acid
  • (+/-)-fenoprofen
  • (+/-)-m-phenoxyhydratropic acid
  • 2-(3-phenoxyphenyl)propionic acid
  • 2-(m-phenoxyphenyl)propionic acid
  • 3-phenoxyhydratropic acid
  • alpha-(m-Phenoxyphenyl)propionic acid
  • alpha-Methyl-3-phenoxybenzeneacetic acid
  • DL-2-(3-phenoxyphenyl)propionic acid
  • Fenoprofen
  • Fénoprofène
  • Fenoprofeno
  • Fenoprofenum
External IDs
69323 / Lilly 53858 / LILLY-53858
Product Ingredients
IngredientUNIICASInChI Key
Fenoprofen calcium0X2CW1QABJ53746-45-5LZPBLUATTGKZBH-UHFFFAOYSA-L
Fenoprofen sodium869607J16Q34691-31-1WVKIYGXHDKTNFO-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FenoprofenCapsule200 mg/1OralBelcher Pharmaceuticals, LLC2017-04-19Not applicableUs
FenoprofenCapsule400 mg/1OralKLE 2, Inc.2014-07-142015-11-05Us
FenoprofenCapsule400 mg/1Oralbryant ranch prepack2014-07-14Not applicableUs
FenoprofenCapsule400 mg/1OralMesource Pharmaceuticals2014-07-142016-06-30Us
FenoprofenCapsule400 mg/1OralPreferreed Pharmaceuticals Inc.2014-08-202017-08-09Us
Fenoprofen CalciumCapsule400 mg/1OralBurke Therapeutics, LLC2017-07-03Not applicableUs
Fenoprofen CalciumCapsule400 mg/1OralBpi Labs Llc2016-07-06Not applicableUs
Fenoprofen CalciumCapsule200 mg/1OralBpi Labs Llc2016-07-06Not applicableUs
Fenoprofen CalciumCapsule200 mg/1OralSterling Knight Pharmaceuticals2016-07-06Not applicableUs
FenorthoCapsule400 mg/1OralBpi Labs Llc2016-06-142017-03-21Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fenoprofen CalciumTablet, film coated600 mg/1OralPhysicians Total Care, Inc.2009-11-232012-06-30Us
Fenoprofen CalciumTablet, film coated600 mg/1OralXspire Pharma, Llc2018-02-12Not applicableUs
Fenoprofen CalciumCapsule400 mg/1OralXspire Pharma2016-05-19Not applicableUs
Fenoprofen CalciumCapsule400 mg/1OralA-S Medication Solutions2016-05-19Not applicableUs
Fenoprofen CalciumCapsule400 mg/1Oralbryant ranch prepack2016-05-19Not applicableUs
Fenoprofen CalciumCapsule400 mg/1OralAidarex Pharmaceuticals LLC2016-05-19Not applicableUs
Fenoprofen CalciumTablet, film coated600 mg/1OralMylan Pharmaceuticals2012-11-14Not applicableUs
Fenoprofen CalciumCapsule400 mg/1OralGentex Pharma2018-06-28Not applicableUs
Fenoprofen CalciumTablet, film coated600 mg/1OralPd Rx Pharmaceuticals, Inc.2012-11-14Not applicableUs
FenorthoCapsule200 mg/1OralSterling Knight Pharmaceuticals, Llc2017-03-21Not applicableUs
International/Other Brands
Feilin (Hengshan Pharmaceutical) / Fenopron (Typharm) / Fepron (Sheng Chung Tang) / Kimpron (Daewoong) / Nalgésic (Sciencex) / Nonsic (Hasan) / Noprofen (Panion & BF) / Trandor (Biolab)
Categories
UNII
RA33EAC7KY
CAS number
29679-58-1
Weight
Average: 242.2699
Monoisotopic: 242.094294314
Chemical Formula
C15H14O3
InChI Key
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)
IUPAC Name
2-(3-phenoxyphenyl)propanoic acid
SMILES
CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1

Pharmacology

Indication

For relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.

Associated Conditions
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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
UProstaglandin G/H synthase 1
inhibitor
Human
UPeroxisome proliferator-activated receptor alpha
activator
Human
UPeroxisome proliferator-activated receptor gammaNot AvailableHuman
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
PathwayCategory
Fenoprofen Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Fenoprofen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Fenoprofen is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Fenoprofen is combined with 4-hydroxycoumarin.
AbacavirFenoprofen 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 Fenoprofen is combined with Abciximab.
AcarboseFenoprofen may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololFenoprofen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Acemetacin.
AcenocoumarolThe risk or severity of gastrointestinal bleeding can be increased when Fenoprofen is combined with Acenocoumarol.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

References

Synthesis Reference

Marshall, W.S.; U.S. Patent 3,600,437; August 17, 1971; assigned to Eli Lilly and Company.

General References
Not Available
External Links
Human Metabolome Database
HMDB0014713
KEGG Drug
D00968
KEGG Compound
C06997
PubChem Compound
3342
PubChem Substance
46504597
ChemSpider
3225
BindingDB
54705
ChEBI
5004
ChEMBL
CHEMBL1297
Therapeutic Targets Database
DAP000619
PharmGKB
PA449597
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fenoprofen
ATC Codes
M01AE04 — Fenoprofen
FDA label
Download (141 KB)

Clinical Trials

Clinical Trials
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
  • A-S Medication Solutions LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Eli Lilly & Co.
  • H.J. Harkins Co. Inc.
  • Ivax Pharmaceuticals
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • PEDiNOL
  • Pharmedix
  • Physicians Total Care Inc.
  • Prescript Pharmaceuticals
  • Professional Co.
  • Ranbaxy Laboratories
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
Dosage forms
FormRouteStrength
CapsuleOral400 mg/1
Tablet, film coatedOral600 mg/1
CapsuleOral200 mg/1
CapsuleOral300 mg/1
CapsuleOral300 mg
TabletOral600 mg
Prices
Unit descriptionCostUnit
Fenoprofen calcium powder1.59USD g
Fenoprofen Calcium 600 mg tablet1.01USD tablet
Nalfon 200 mg capsule0.91USD capsule
Fenoprofen 600 mg tablet0.88USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)168-171Marshall, W.S.; U.S. Patent 3,600,437; August 17, 1971; assigned to Eli Lilly and Company.
water solubilitySlight (calcium salt)Not Available
logP3.1Not Available
pKa4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0811 mg/mLALOGPS
logP3.87ALOGPS
logP3.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.18 m3·mol-1ChemAxon
Polarizability25.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.8373
Caco-2 permeable+0.8876
P-glycoprotein substrateNon-substrate0.6587
P-glycoprotein inhibitor INon-inhibitor0.8897
P-glycoprotein inhibitor IINon-inhibitor0.9357
Renal organic cation transporterNon-inhibitor0.8521
CYP450 2C9 substrateNon-substrate0.6883
CYP450 2D6 substrateNon-substrate0.9354
CYP450 3A4 substrateNon-substrate0.6779
CYP450 1A2 substrateInhibitor0.5871
CYP450 2C9 inhibitorNon-inhibitor0.8382
CYP450 2D6 inhibitorNon-inhibitor0.9769
CYP450 2C19 inhibitorNon-inhibitor0.7675
CYP450 3A4 inhibitorNon-inhibitor0.938
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8169
Ames testNon AMES toxic0.9558
CarcinogenicityNon-carcinogens0.7885
BiodegradationReady biodegradable0.5267
Rat acute toxicity1.9985 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9517
hERG inhibition (predictor II)Non-inhibitor0.9414
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0900000000-0b8ab61fb369335a1792
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0900000000-0a6fe356f953cf25a938

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Phenylpropanoic acids / Diarylethers / Phenoxy compounds / Phenol ethers / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Diphenylether / 2-phenylpropanoic-acid / Diaryl ether / Phenoxy compound / Phenol ether / Monocarboxylic acid or derivatives / Ether / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:5004)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
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:17050798]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
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:17050798]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [PubMed:9013583]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Curator comments
activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [PubMed:9013583]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. [PubMed:9275312]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 16:44