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Identification
NameFenoprofen
Accession NumberDB00573  (APRD00970)
TypeSmall Molecule
GroupsApproved
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 Identifiers
  • 69323
  • Lilly 53858
  • LILLY-53858
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fenoprofencapsule400 mg/1oralKLE 2, Inc.2014-07-142015-12-29Us
Fenoprofencapsule400 mg/1oralPreferred Pharmaceuticals, Inc.2014-08-20Not applicableUs
Fenoprofencapsule400 mg/1oralbryant ranch prepack2014-07-14Not applicableUs
Fenoprofencapsule400 mg/1oralMedsource Pharmaceuticals2014-07-14Not applicableUs
Fenoprofen Calciumcapsule400 mg/1oralXspire Pharma Llc2015-08-05Not applicableUs
Nalfoncapsule200 mg/1oralXspire Pharma2012-08-27Not applicableUs
Nalfoncapsule400 mg/1oralXspire Pharma2012-08-27Not applicableUs
Nalfon Cap 300mgcapsule300 mgoralEli Lilly Canada Inc1975-12-312002-07-26Canada
Nalfon Tab 600mgtablet600 mgoralEli Lilly Canada Inc1975-12-312002-07-26Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fenoprofen Calciumtablet, film coated600 mg/1oralMylan Pharmaceuticals Inc.2012-11-14Not applicableUs
Fenoprofen Calciumtablet, film coated600 mg/1oralPd Rx Pharmaceuticals, Inc.2009-11-23Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
FeilinHengshan Pharmaceutical
FenopronTypharm
FepronSheng Chung Tang
KimpronDaewoong
NalgésicSciencex
NonsicHasan
NoprofenPanion & BF
TrandorBiolab
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Fenoprofen calcium
53746-45-5
Thumb
  • InChI Key: LZPBLUATTGKZBH-UHFFFAOYSA-L
  • Monoisotopic Mass: 558.1566588
  • Average Mass: 558.64
DBSALT001038
Fenoprofen sodium
34691-31-1
Thumb
  • InChI Key: WVKIYGXHDKTNFO-UHFFFAOYSA-M
  • Monoisotopic Mass: 264.07623856
  • Average Mass: 264.256
DBSALT001848
Categories
UNIIRA33EAC7KY
CAS number29679-58-1
WeightAverage: 242.2699
Monoisotopic: 242.094294314
Chemical FormulaC15H14O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • 2-phenylpropanoic-acid
  • Diaryl ether
  • Phenylacetate
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.
PharmacodynamicsFenoprofen 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 actionFenoprofen'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.
Related Articles
AbsorptionRapidly 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 distributionNot Available
Protein binding99% 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.

SubstrateEnzymesProduct
Fenoprofen
Not Available
4'-hydroxyfenoprofen glucuronideDetails
Fenoprofen
Not Available
Fenoprofen glucuronideDetails
Route of eliminationNot Available
Half lifePlasma half-life is approximately 3 hours.
ClearanceNot Available
ToxicitySymptoms 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
PathwayCategorySMPDB ID
Fenoprofen Action PathwayDrug actionSMP00696
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
FormRouteStrength
Capsuleoral400 mg/1
Tablet, film coatedoral600 mg/1
Capsuleoral200 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point168-171Marshall, 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

General ReferencesNot Available
External Links
ATC CodesM01AE04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (141 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabFenoprofen may increase the anticoagulant activities of Abciximab.
AcenocoumarolFenoprofen may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Acetylsalicylic acid.
AliskirenFenoprofen may decrease the antihypertensive activities of Aliskiren.
AlteplaseFenoprofen may increase the anticoagulant activities of Alteplase.
AmikacinFenoprofen may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAmitriptyline may increase the antiplatelet activities of Fenoprofen.
AnistreplaseFenoprofen may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Apixaban.
ArbekacinFenoprofen may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazideFenoprofen may increase the nephrotoxic activities of Balsalazide.
Citric AcidFenoprofen may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Fenoprofen resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Collagenase.
CyclosporineFenoprofen may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilateFenoprofen may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinFenoprofen may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Fenoprofen.
DeferasiroxThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Fenoprofen.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Fenoprofen.
DicoumarolFenoprofen may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Fenoprofen.
DrospirenoneFenoprofen may increase the hyperkalemic activities of Drospirenone.
Edetic AcidFenoprofen may increase the anticoagulant activities of Edetic Acid.
EnoxaparinFenoprofen may increase the anticoagulant activities of Enoxaparin.
EplerenoneFenoprofen may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetateFenoprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Fenoprofen.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Fenoprofen.
Fondaparinux sodiumFenoprofen may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinFenoprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinFenoprofen may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
GlucosamineGlucosamine may increase the antiplatelet activities of Fenoprofen.
HaloperidolThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Haloperidol.
HeparinFenoprofen may increase the anticoagulant activities of Heparin.
HomoharringtonineThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Homoharringtonine.
HydralazineFenoprofen may decrease the antihypertensive activities of Hydralazine.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fenoprofen.
IcosapentThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Fenoprofen.
KanamycinFenoprofen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Fenoprofen.
LimaprostLimaprost may increase the antiplatelet activities of Fenoprofen.
LithiumThe serum concentration of Lithium can be increased when it is combined with Fenoprofen.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Fenoprofen.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Fenoprofen.
NadololFenoprofen may decrease the antihypertensive activities of Nadolol.
NeomycinFenoprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinFenoprofen may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
ObinutuzumabThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Fenoprofen.
PamidronateThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Fenoprofen.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Fenoprofen.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Fenoprofen.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Fenoprofen.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Fenoprofen.
PhenindioneFenoprofen may increase the anticoagulant activities of Phenindione.
PhenprocoumonFenoprofen may increase the anticoagulant activities of Phenprocoumon.
PorfimerFenoprofen may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Fenoprofen.
ProbenecidThe serum concentration of Fenoprofen can be increased when it is combined with Probenecid.
ReteplaseFenoprofen may increase the anticoagulant activities of Reteplase.
RibostamycinFenoprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelFenoprofen may increase the anticoagulant activities of Ridogrel.
RivaroxabanFenoprofen may increase the anticoagulant activities of Rivaroxaban.
SparfloxacinFenoprofen may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinFenoprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinaseFenoprofen may increase the anticoagulant activities of Streptokinase.
StreptomycinFenoprofen may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulodexideFenoprofen may increase the anticoagulant activities of Sulodexide.
TacrolimusFenoprofen may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Fenoprofen.
TenecteplaseFenoprofen may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Tenofovir.
TipranavirTipranavir may increase the antiplatelet activities of Fenoprofen.
TobramycinFenoprofen may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideFenoprofen may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Fenoprofen.
TriamtereneFenoprofen may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Fenoprofen.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Fenoprofen.
UrokinaseFenoprofen may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Fenoprofen.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Fenoprofen.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Fenoprofen.
VerteporfinFenoprofen may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Fenoprofen.
WarfarinFenoprofen may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

Targets

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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
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
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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
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 ]

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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 04, 2016 17:03