Fenoprofen

Identification

Summary

Fenoprofen is an anti-inflammatory analgesic used to treat mild to moderate pain in addition to the signs and symptoms of rheumatoid arthritis and osteoarthritis.

Brand Names
Fenortho, Nalfon
Generic Name
Fenoprofen
DrugBank Accession Number
DB00573
Background

An anti-inflammatory analgesic and antipyretic highly bound to plasma proteins. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 242.2699
Monoisotopic: 242.094294314
Chemical Formula
C15H14O3
Synonyms
  • (+/-)-fenoprofen
  • (+/-)-m-phenoxyhydratropic acid
  • (±)-2-(3-phenoxyphenyl)propionic acid
  • 2-(3-phenoxyphenyl)propionic acid
  • 2-(m-phenoxyphenyl)propionic acid
  • 3-phenoxyhydratropic acid
  • DL-2-(3-phenoxyphenyl)propionic acid
  • Fenoprofen
  • Fénoprofène
  • Fenoprofeno
  • Fenoprofenum
  • α-(m-phenoxyphenyl)propionic acid
  • α-methyl-3-phenoxybenzeneacetic acid
External IDs
  • 69323
  • Lilly 53858
  • LILLY-53858

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofOsteoarthritis••••••••••••
Symptomatic treatment ofRheumatoid arthritis••••••••••••
Management ofMild pain•••••••••••••••••
Management ofModerate pain•••••••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
UPeroxisome proliferator-activated receptor alpha
activator
Humans
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
UProstaglandin G/H synthase 1
inhibitor
Humans
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.

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Plasma half-life is approximately 3 hours.

Clearance

Not Available

Adverse Effects
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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.

Pathways
PathwayCategory
Fenoprofen Action PathwayDrug action
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
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.
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.
Food Interactions
  • Avoid alcohol.
  • Take with food. Food reduces irritation.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fenoprofen calcium0X2CW1QABJ53746-45-5LZPBLUATTGKZBH-UHFFFAOYSA-L
Fenoprofen sodium869607J16Q34691-31-1WVKIYGXHDKTNFO-UHFFFAOYSA-M
International/Other Brands
Feilin (Hengshan Pharmaceutical) / Fenopron (Typharm) / Fepron (Sheng Chung Tang) / Kimpron (Daewoong) / Nalgésic (Sciencex) / Nonsic (Hasan) / Noprofen (Panion & BF) / Trandor (Biolab)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FenoprofenCapsule400 mg/1OralMesource Pharmaceuticals2014-07-142016-06-30US flag
FenoprofenCapsule400 mg/1OralPreferreed Pharmaceuticals Inc.2014-08-202017-08-09US flag
FenoprofenCapsule400 mg/1OralKLE 2, Inc.2014-07-142015-11-05US flag
FenoprofenCapsule400 mg/1Oralbryant ranch prepack2014-07-14Not applicableUS flag
FenoprofenCapsule200 mg/1OralBelcher Pharmaceuticals, LLC2017-04-19Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Fenoprofen CalciumCapsule400 mg/1OralA-S Medication Solutions2016-05-19Not applicableUS flag
Fenoprofen CalciumTablet, film coated600 mg/1OralMylan Pharmaceuticals Inc.2012-11-142020-08-31US flag
Fenoprofen CalciumCapsule400 mg/1OralProficient Rx LP2022-08-01Not applicableUS flag
Fenoprofen CalciumCapsule400 mg/1OralXspire Pharma2016-05-19Not applicableUS flag
Fenoprofen CalciumTablet, film coated600 mg/1OralPD-Rx Pharmaceuticals, Inc.2012-11-142019-09-09US flag

Categories

ATC Codes
M01AE04 — Fenoprofen
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-phenylpropanoic-acid / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diaryl ether / Diphenylether / Ether / Hydrocarbon derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:5004)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
RA33EAC7KY
CAS number
29679-58-1
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

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
Human Metabolome Database
HMDB0014713
KEGG Drug
D00968
KEGG Compound
C06997
PubChem Compound
3342
PubChem Substance
46504597
ChemSpider
3225
BindingDB
54705
RxNav
4331
ChEBI
5004
ChEMBL
CHEMBL1297
Therapeutic Targets Database
DAP000619
PharmGKB
PA449597
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fenoprofen
FDA label
Download (141 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
TabletOral
CapsuleOral200 mg/1
CapsuleOral300 mg/1
CapsuleOral300 mg / cap
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)-3.7Chemaxon
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-MSsplash10-0002-4920000000-d5b009ac51d1a009654f
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-0900000000-856a8aff822346800d28
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-0900000000-856a8aff822346800d28
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-0900000000-856a8aff822346800d28
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0900000000-0b8ab61fb369335a1792
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0900000000-0a6fe356f953cf25a938
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0690000000-d65342079ecbf4b70b51
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-0900000000-aa0799628128ceb62124
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-0920000000-dacb70383c91032fd89e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udj-1900000000-836b64b9362c3a54bfcb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2900000000-dc55225bc01b02a09ffe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3900000000-ae1160f5e3aa8cfb9615
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-167.1304103
predicted
DarkChem Lite v0.1.0
[M-H]-152.32225
predicted
DeepCCS 1.0 (2019)
[M+H]+167.4328103
predicted
DarkChem Lite v0.1.0
[M+H]+154.71782
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.3009103
predicted
DarkChem Lite v0.1.0
[M+Na]+160.76186
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Carriers

Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:00