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Identification
NameKetoprofen
Accession NumberDB01009  (APRD01059, DB05823)
TypeSmall Molecule
GroupsApproved
Description

Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.

Structure
Thumb
Synonyms
2-(3-Benzoylphenyl)propionic acid
3-Benzoyl-alpha-methylbenzeneacetic acid
3-Benzoyl-α-methylbenzeneacetic acid
3-Benzoylhydratropic acid
Ketoprofen
L'Acide (benzoyl-3-phenyl)-2-propionique
m-Benzoylhydratropic acid
Orudis (tn)
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ketoprofencapsule50 mgoralAa Pharma Inc1989-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen SRtablet (extended-release)200 mgoralAa Pharma Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen Suppositoriessuppository100 mgrectalPharmel Inc1998-06-04Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen Suppositoriessuppository50 mgrectalPharmel IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen-Etablet (enteric-coated)50 mgoralAa Pharma Inc1989-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen-Etablet (enteric-coated)100 mgoralAa Pharma Inc1989-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen-E Ect 100mgtablet (enteric-coated)100 mgoralPro Doc Limitee1996-12-312009-07-23Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen-E Ect 50mgtablet (enteric-coated)50 mgoralPro Doc Limitee1995-12-312009-07-23Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ketoprofen-SR - Srt 200mgtablet (extended-release)200 mgoralPro Doc Limitee1997-09-182009-07-23Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-keto Suppositories 100mgsuppository100 mgrectalNovopharm Limited1996-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-keto-EC Tab 100mgtablet (enteric-coated)100 mgoralNovopharm Limited1992-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-keto-EC Tab 50mgtablet (enteric-coated)50 mgoralNovopharm Limited1992-12-312005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-ketoprofen Cap 50mgcapsule50 mgoralNu Pharm Inc1993-12-312012-09-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-ketoprofen-E Ect 100mgtablet (enteric-coated)100 mgoralNu Pharm Inc1994-12-312012-09-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-ketoprofen-E Ect 50mgtablet (enteric-coated)50 mgoralNu Pharm Inc1994-12-312012-09-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orafen - Sup RT 100mgsuppository100 mgrectalTechnilab Pharma Inc.1996-12-312004-08-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orudis 100suppository100 mgrectalAventis Pharma Inc1979-12-312003-07-22Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orudis 50suppository50 mgrectalAventis Pharma Inc1991-12-312003-07-22Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orudis Cap 50mgcapsule50 mgoralAventis Pharma Inc1979-12-312004-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orudis E-100tablet (enteric-coated)100 mgoralAventis Pharma Inc1987-12-312003-07-22Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orudis E-50tablet (enteric-coated)50 mgoralAventis Pharma Inc1983-12-312004-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Orudis SR-200tablet (extended-release)200 mgoralAventis Pharma Inc1988-12-312005-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Oruvail 150capsule (sustained-release)150 mgoralAventis Pharma Inc1991-12-312003-07-22Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Oruvail 200capsule (sustained-release)200 mgoralAventis Pharma Inc1991-12-312003-07-22Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS-ketoprofensuppository100 mgrectalPharmascience Inc1993-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS-ketoprofensuppository50 mgrectalPharmascience Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS-ketoprofen Capsulescapsule50 mgoralPharmascience Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS-ketoprofen E-100 - Ecttablet (enteric-coated)100 mgoralPharmascience Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS-ketoprofen E-50 - Ect 50mgtablet (enteric-coated)50 mgoralPharmascience Inc1995-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhodissuppository100 mgrectalSanofi Aventis Canada Inc1988-12-312006-07-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhodis Cap 50mgcapsule50 mgoralRhodiapharm Inc1988-12-312005-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhodis ECtablet (enteric-coated)100 mgoralSanofi Aventis Canada Inc1988-12-312007-01-11Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhodis ECtablet (enteric-coated)50 mgoralSanofi Aventis Canada Inc1988-12-312006-07-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhodis SR 200mgtablet (extended-release)200 mgoralRhodiapharm Inc1995-12-312005-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhovail 150capsule (sustained-release)150 mgoralRhodiapharm Inc1995-12-312005-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhovail 200capsule (sustained-release)200 mgoralRhodiapharm Inc1995-12-312005-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vopac - Ketoprofen, Lidocaine Hydrochloride PackitSircle Laboratories, Llc2015-03-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ketoprofencapsule50 mg/1oralTeva Pharmaceuticals USA Inc1993-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule, extended release200 mg/1oralPhysicians Total Care, Inc.2009-06-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralPreferred Pharmaceuticals, Inc.2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralRebel Distributors Corp2010-04-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralA S Medication Solutions Llc1993-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofentablet75 mg/1oralRed Pharm Drug Inc.2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralSTAT Rx USA LLC2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralH.J. Harkins Company, Inc.2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralbryant ranch prepack2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralSTAT Rx USA LLC2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralAv Kare, Inc.2013-07-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralbryant ranch prepack2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule, extended release200 mg/1oralMylan Pharmaceuticals Inc.2003-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralAv Kare, Inc.2013-07-08Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralProficient Rx LP1993-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralMylan Pharmaceuticals Inc.1997-01-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralRebel Distributors Corp2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralPd Rx Pharmaceuticals, Inc.2010-04-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralMylan Pharmaceuticals Inc.1997-01-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralAidarex Pharmaceuticals LLC1993-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralPhysicians Total Care, Inc.2005-08-15Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralPd Rx Pharmaceuticals, Inc.2011-01-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralTeva Pharmaceuticals USA Inc1993-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mg/1oralRebel Distributors Corp2010-04-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mg/1oralPhysicians Total Care, Inc.1997-02-14Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
ActronNot Available
AlrheumunTeofarma
CapistenKissei
EpatecZeria Shinyaku
FastumMenarini
MenaminDaiko Seiyaku
OrudisAbbott
Orudis KTSanofi
OrugesicSanofi
OruvailWyeth
OscorelSanofi
ProfenidSanofi
ToprecSanofi
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number22071-15-4
WeightAverage: 254.2806
Monoisotopic: 254.094294314
Chemical FormulaC16H14O3
InChI KeyInChIKey=DKYWVDODHFEZIM-UHFFFAOYSA-N
InChI
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
IUPAC Name
2-(3-benzoylphenyl)propanoic acid
SMILES
CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Diphenylmethane
  • 2-phenylpropanoic-acid
  • Phenylacetate
  • Acetophenone
  • Aryl ketone
  • Benzoyl
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain.
PharmacodynamicsKetoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.
Mechanism of actionThe anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.
AbsorptionKetoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.
Volume of distributionNot Available
Protein binding99% bound, primarily to albumin
Metabolism

Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.

SubstrateEnzymesProduct
Ketoprofen
Not Available
Ketoprofen glucuronideDetails
Route of eliminationIn a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.
Half lifeConventional capsules: 1.1-4 hours

Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)

Clearance
  • Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 × 50 mg)]
  • Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 × 200 mg)]
  • 0.08 L/kg/h
  • 0.7 L/kg/h [alcoholic cirrhosis patients]
ToxicityLD50=62.4 mg/kg (rat, oral).

Symptoms of overdose include drowsiness, vomiting and abdominal pain.

Side effects are usually mild and mainly involved the GI tract. Most common adverse GI effect is dyspepsia (11% of patients). May cause nausea, diarrhea, abdominal pain, constipation and flatulence in greater than 3% of patients.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.7132
P-glycoprotein inhibitor INon-inhibitor0.9168
P-glycoprotein inhibitor IINon-inhibitor0.9589
Renal organic cation transporterNon-inhibitor0.8818
CYP450 2C9 substrateNon-substrate0.7183
CYP450 2D6 substrateNon-substrate0.9598
CYP450 3A4 substrateNon-substrate0.7685
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9604
CYP450 2C19 inhibitorNon-inhibitor0.9465
CYP450 3A4 inhibitorNon-inhibitor0.9598
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9438
Ames testNon AMES toxic0.9801
CarcinogenicityNon-carcinogens0.6299
BiodegradationReady biodegradable0.6701
Rat acute toxicity2.2378 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9661
hERG inhibition (predictor II)Non-inhibitor0.9595
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Elan pharmaceutical research corp
  • Mylan pharmaceuticals inc
  • Watson laboratories inc florida
  • Wyeth pharmaceuticals inc
  • Heritage pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Wyeth ayerst laboratories
  • Novartis consumer health inc
  • Bayer healthcare llc
  • L perrigo co
  • Wyeth consumer healthcare
Packagers
Dosage forms
FormRouteStrength
Capsuleoral50 mg/1
Capsuleoral50 mg
Capsuleoral75 mg/1
Capsule, extended releaseoral200 mg/1
Tabletoral75 mg/1
Tablet (extended-release)oral200 mg
Tablet (enteric-coated)oral100 mg
Tablet (enteric-coated)oral50 mg
Capsule (sustained-release)oral150 mg
Capsule (sustained-release)oral200 mg
Suppositoryrectal100 mg
Suppositoryrectal50 mg
Kit
Prices
Unit descriptionCostUnit
Ketoprofen powder43.74USD g
Ketoprofen micronized powder3.84USD g
Ketoprofen CR 200 mg 24 Hour Capsule2.8USD capsule
Orudis 75 mg capsule1.58USD capsule
Apo-Keto Sr 200 mg Sustained-Release Tablet1.46USD tablet
Ketoprofen 75 mg capsule1.12USD capsule
Pms-Ketoprofen 100 mg Suppository1.1USD suppository
Ketoprofen 50 mg capsule1.0USD capsule
Apo-Keto-E 100 mg Enteric-Coated Tablet0.71USD tablet
Apo-Keto 50 mg Capsule0.35USD capsule
Apo-Keto-E 50 mg Enteric-Coated Tablet0.35USD tablet
Orudis kt 12.5 mg tablet0.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point94 °CU.S. Patent 3,641,127.
water solubility51 mg/L (at 22 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.12SANGSTER (1993)
logS-3.7ADME Research, USCD
pKa4.45SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0213 mg/mLALOGPS
logP3.29ALOGPS
logP3.61ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.52 m3·mol-1ChemAxon
Polarizability26.56 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

Attilio Citterio, Daniele Fancelli, “Method of preparing ketoprofen.” U.S. Patent US4845281, issued December, 1982.

US4845281
General References
  1. Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. Pubmed
  2. Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. Pubmed
External Links
ATC CodesM01AE03M02AA10
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelDownload (160 KB)
MSDSDownload (75.9 KB)
Interactions
Drug Interactions
Drug
AbciximabKetoprofen may increase the anticoagulant activities of Abciximab.
AcenocoumarolKetoprofen may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Acetylsalicylic acid.
AliskirenKetoprofen may decrease the antihypertensive activities of Aliskiren.
AlteplaseKetoprofen may increase the anticoagulant activities of Alteplase.
AmikacinKetoprofen 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 Ketoprofen.
AnistreplaseKetoprofen may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Apixaban.
ArbekacinKetoprofen may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazideKetoprofen may increase the nephrotoxic activities of Balsalazide.
Citric AcidKetoprofen may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Ketoprofen resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Collagenase.
CyclosporineKetoprofen may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilateKetoprofen may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinKetoprofen may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Ketoprofen.
DeferasiroxThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Ketoprofen.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Ketoprofen.
DicoumarolKetoprofen may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Ketoprofen.
DrospirenoneKetoprofen may increase the hyperkalemic activities of Drospirenone.
Edetic AcidKetoprofen may increase the anticoagulant activities of Edetic Acid.
EnoxaparinKetoprofen may increase the anticoagulant activities of Enoxaparin.
EplerenoneKetoprofen may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetateKetoprofen may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Ketoprofen.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Ketoprofen.
Fondaparinux sodiumKetoprofen may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinKetoprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinKetoprofen 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 Ketoprofen.
HaloperidolThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Haloperidol.
HeparinKetoprofen may increase the anticoagulant activities of Heparin.
HomoharringtonineThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Homoharringtonine.
HydralazineKetoprofen may decrease the antihypertensive activities of Hydralazine.
IbritumomabThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ketoprofen.
IcosapentThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Ketoprofen.
KanamycinKetoprofen 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 Ketoprofen.
LimaprostLimaprost may increase the antiplatelet activities of Ketoprofen.
LithiumThe serum concentration of Lithium can be increased when it is combined with Ketoprofen.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Ketoprofen.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Ketoprofen.
NadololKetoprofen may decrease the antihypertensive activities of Nadolol.
NeomycinKetoprofen may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinKetoprofen 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 Ketoprofen is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Ketoprofen.
PamidronateThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Ketoprofen.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Ketoprofen.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ketoprofen.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Ketoprofen.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Ketoprofen.
PhenindioneKetoprofen may increase the anticoagulant activities of Phenindione.
PhenprocoumonKetoprofen may increase the anticoagulant activities of Phenprocoumon.
PorfimerKetoprofen may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Ketoprofen.
ProbenecidThe serum concentration of Ketoprofen can be increased when it is combined with Probenecid.
ReteplaseKetoprofen may increase the anticoagulant activities of Reteplase.
RibostamycinKetoprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelKetoprofen may increase the anticoagulant activities of Ridogrel.
RivaroxabanKetoprofen may increase the anticoagulant activities of Rivaroxaban.
Salicylate-sodiumThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Salicylate-sodium.
SparfloxacinKetoprofen may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinKetoprofen may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinaseKetoprofen may increase the anticoagulant activities of Streptokinase.
StreptomycinKetoprofen may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulodexideKetoprofen may increase the anticoagulant activities of Sulodexide.
TacrolimusKetoprofen may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Ketoprofen.
TenecteplaseKetoprofen may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Tenofovir.
TeriflunomideThe serum concentration of Ketoprofen can be increased when it is combined with Teriflunomide.
TipranavirTipranavir may increase the antiplatelet activities of Ketoprofen.
TobramycinKetoprofen may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideKetoprofen may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ketoprofen.
TriamtereneKetoprofen may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Ketoprofen.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Ketoprofen.
UrokinaseKetoprofen may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Ketoprofen.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Ketoprofen.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Ketoprofen.
VerteporfinKetoprofen may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Ketoprofen.
WarfarinKetoprofen may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Avoid alcohol.
  • Food prolongs rate of absorption and decreases peak plasma concentration. Extent of absorption is not affected.
  • Take with food to reduce gastric irritation.

Targets

1. Prostaglandin G/H synthase 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Parsadaniantz SM, Lebeau A, Duval P, Grimaldi B, Terlain B, Kerdelhue B: Effects of the inhibition of cyclo-oxygenase 1 or 2 or 5-lipoxygenase on the activation of the hypothalamic-pituitary-adrenal axis induced by interleukin-1beta in the male Rat. J Neuroendocrinol. 2000 Aug;12(8):766-73. Pubmed
  2. Kurahashi K, Shirahase H, Nakamura S, Tarumi T, Koshino Y, Wang AM, Nishihashi T, Shimizu Y: Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites. J Cardiovasc Pharmacol. 2001 Oct;38 Suppl 1:S21-5. Pubmed
  3. Zuniga J, Fuenzalida M, Guerrero A, Illanes J, Dabancens A, Diaz E, Lemus D: Effects of steroidal and non steroidal drugs on the neovascularization response induced by tumoral TA3 supernatant on CAM from chick embryo. Biol Res. 2003;36(2):233-40. Pubmed
  4. Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. Pubmed
  5. Levoin N, Blondeau C, Guillaume C, Grandcolas L, Chretien F, Jouzeau JY, Benoit E, Chapleur Y, Netter P, Lapicque F: Elucidation of the mechanism of inhibition of cyclooxygenases by acyl-coenzyme A and acylglucuronic conjugates of ketoprofen. Biochem Pharmacol. 2004 Nov 15;68(10):1957-69. Pubmed

2. Prostaglandin G/H synthase 2

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Kay-Mugford P, Benn SJ, LaMarre J, Conlon P: In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. Pubmed
  2. Sommerauer M, Ates M, Guhring H, Brune K, Amann R, Peskar BA: Ketoprofen-induced cyclooxygenase inhibition in renal medulla and platelets of rats treated with caffeine. Pharmacology. 2001;63(4):234-9. Pubmed
  3. Levoin N, Chretien F, Lapicque F, Chapleur Y: Synthesis and biological testing of Acyl-CoA-ketoprofen conjugates as selective irreversible inhibitors of COX-2. Bioorg Med Chem. 2002 Mar;10(3):753-7. Pubmed
  4. Zuniga J, Fuenzalida M, Guerrero A, Illanes J, Dabancens A, Diaz E, Lemus D: Effects of steroidal and non steroidal drugs on the neovascularization response induced by tumoral TA3 supernatant on CAM from chick embryo. Biol Res. 2003;36(2):233-40. Pubmed
  5. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. C-X-C chemokine receptor type 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: other

Components

Name UniProt ID Details
C-X-C chemokine receptor type 1 P25024 Details

References:

  1. Allegretti M, Bertini R, Cesta MC, Bizzarri C, Di Bitondo R, Di Cioccio V, Galliera E, Berdini V, Topai A, Zampella G, Russo V, Di Bello N, Nano G, Nicolini L, Locati M, Fantucci P, Florio S, Colotta F: 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J Med Chem. 2005 Jun 30;48(13):4312-31. Pubmed
  2. Bizzarri C, Pagliei S, Brandolini L, Mascagni P, Caselli G, Transidico P, Sozzani S, Bertini R: Selective inhibition of interleukin-8-induced neutrophil chemotaxis by ketoprofen isomers. Biochem Pharmacol. 2001 Jun 1;61(11):1429-37. Pubmed
  3. Wang LM, Toyoshima A, Mineshita S, Wang XX, Yamamoto T, Nomura Y, Yang L, Koikei Y, Shiba K, Honda Y: The anti-inflammatory effects of ketoprofen in animal experiments. Drugs Exp Clin Res. 1997;23(1):1-6. Pubmed

Enzymes

1. Cytochrome P450 2C9

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Carriers

1. Serum albumin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bertucci C: Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. Chirality. 2001 Jul;13(7):372-8. Pubmed
  2. Lagrange F, Penhourcq F, Matoga M, Bannwarth B: Binding of ketoprofen enantiomers in various human albumin preparations. J Pharm Biomed Anal. 2000 Oct;23(5):793-802. Pubmed
  3. Li F, Zhou D, Guo X: Study on the protein binding of ketoprofen using capillary electrophoresis frontal analysis compared with liquid chromatography frontal analysis. J Chromatogr Sci. 2003 Mar;41(3):137-41. Pubmed
  4. Zhou D, Li F: [Study of protein binding in ketoprofen using liquid chromatography frontal analysis in comparison with capillary electrophoresis frontal analysis] Se Pu. 2004 Nov;22(6):601-4. Pubmed

Transporters

1. Multidrug resistance-associated protein 4

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 4 O15439 Details

References:

  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. Pubmed

2. Solute carrier organic anion transporter family member 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. Pubmed

3. Solute carrier family 22 member 6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. Pubmed
  2. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. Pubmed
  3. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. Pubmed
  4. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. Pubmed
  5. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. Pubmed

4. Solute carrier family 22 member 8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. Pubmed
  2. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. Pubmed

5. Solute carrier family 22 member 11

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 11 Q9NSA0 Details

References:

  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. Pubmed

6. Solute carrier family 22 member 7

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. Pubmed
  2. Morita N, Kusuhara H, Sekine T, Endou H, Sugiyama Y: Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1179-84. Pubmed
  3. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. Pubmed
  4. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12