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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
SynonymLanguageCode
2-(3-Benzoylphenyl)propionic acidNot AvailableNot Available
3-Benzoyl-alpha-methylbenzeneacetic acidNot AvailableNot Available
3-Benzoyl-α-methylbenzeneacetic acidNot AvailableNot Available
3-Benzoylhydratropic acidNot AvailableNot Available
KetoprofenNot AvailableNot Available
L'Acide (benzoyl-3-phenyl)-2-propioniqueNot AvailableNot Available
m-Benzoylhydratropic acidNot AvailableNot Available
Orudis (tn)Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ketoprofencapsule50 mgoralTeva Pharmaceuticals USA Inc1993-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralTeva Pharmaceuticals USA Inc1993-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralMylan Pharmaceuticals Inc.1997-01-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralMylan Pharmaceuticals Inc.1997-01-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule, extended release200 mgoralMylan Pharmaceuticals Inc.2003-09-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralSTAT Rx USA LLC2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralSTAT Rx USA LLC2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralRebel Distributors Corp2010-04-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralRebel Distributors Corp2010-04-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralAidarex Pharmaceuticals LLC1993-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralRebel Distributors Corp2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralAv Kare, Inc.2013-07-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralAv Kare, Inc.2013-07-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralH.J. Harkins Company, Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralA S Medication Solutions Llc1993-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralPhysicians Total Care, Inc.1997-02-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralPhysicians Total Care, Inc.2005-08-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule, extended release200 mgoralPhysicians Total Care, Inc.2009-06-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralPd Rx Pharmaceuticals, Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralPd Rx Pharmaceuticals, Inc.2010-04-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralProficient Rx LP1993-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralbryant ranch prepack2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralbryant ranch prepack2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofentablet75 mgoralRed Pharm Drug Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule75 mgoralPreferred Pharmaceuticals, Inc.2011-01-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Ketoprofencapsule50 mgoralAa Pharma IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
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 KeyDKYWVDODHFEZIM-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 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.9604
CYP450 2C19 substrateNon-inhibitor0.9465
CYP450 3A4 substrateNon-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
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
Capsuleoral75 mg
Capsule, extended releaseoral200 mg
Tabletoral75 mg
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 Reference
  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
AbciximabAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
AcenocoumarolAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
Acetylsalicylic acidNSAID (Nonselective) may enhance the adverse/toxic effect of Salicylates. An increased risk of bleeding may be associated with use of this combination. NSAID (Nonselective) may diminish the cardioprotective effect of Salicylates. Salicylates may decrease the serum concentration of NSAID (Nonselective). Exceptions: Choline Magnesium Trisalicylate.
AliskirenNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of Aliskiren. Nonsteroidal Anti-Inflammatory Agents may enhance the nephrotoxic effect of Aliskiren.
AlteplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
AmikacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
AnistreplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
ApixabanAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Apixaban. Specifically, the risk for bleeding may be increased.
ArbekacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
Citric AcidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
ColesevelamMay decrease the absorption of Nonsteroidal Anti-Inflammatory Agents.
Dabigatran etexilateAgents with Antiplatelet Properties may enhance the anticoagulant effect of Dabigatran Etexilate. Agents with Antiplatelet Properties may increase the serum concentration of Dabigatran Etexilate. This mechanism applies specifically to clopidogrel.
DalteparinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DasatinibMay enhance the anticoagulant effect of Agents with Antiplatelet Properties.
DeferasiroxNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
Deoxycholic AcidAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Deoxycholic Acid. Specifically, the risk for bleeding or bruising in the treatment area may be increased.
DesmopressinNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Desmopressin.
DicoumarolAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
DigoxinNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Digoxin.
Edetic AcidAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EnoxaparinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
EplerenoneNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of Eplerenone. Nonsteroidal Anti-Inflammatory Agents may enhance the hyperkalemic effect of Eplerenone.
Ethyl biscoumacetateAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FloctafenineMay enhance the adverse/toxic effect of Nonsteroidal Anti-Inflammatory Agents.
Fondaparinux sodiumAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
FramycetinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
GentamicinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
GlucosamineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
HaloperidolNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Haloperidol. Specifically including drowsiness and confusion.
HeparinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
HydralazineNonsteroidal Anti-Inflammatory Agents may diminish the antihypertensive effect of HydrALAZINE.
IbritumomabAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Ibritumomab. Both agents may contribute to impaired platelet function and an increased risk of bleeding.
KanamycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
LithiumNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Lithium.
MethotrexateNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Methotrexate.
NeomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NetilmicinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
ObinutuzumabAgents with Antiplatelet Properties may enhance the adverse/toxic effect of Obinutuzumab. Specifically, the risk of serious bleeding-related events may be increased.
PemetrexedNSAID (Nonselective) may increase the serum concentration of PEMEtrexed.
PentoxifyllineMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
PhenindioneAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
PhenprocoumonAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
PorfimerPhotosensitizing Agents may enhance the photosensitizing effect of Porfimer.
PralatrexateNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of PRALAtrexate. More specifically, NSAIDS may decrease the renal excretion of pralatrexate.
ProbenecidMay increase the serum concentration of Ketoprofen.
ReteplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
RibostamycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
RidogrelAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
RivaroxabanAgents with Antiplatelet Properties may enhance the anticoagulant effect of Rivaroxaban.
Salicylate-sodiumNSAID (Nonselective) may enhance the adverse/toxic effect of Salicylates. An increased risk of bleeding may be associated with use of this combination. NSAID (Nonselective) may diminish the cardioprotective effect of Salicylates. Salicylates may decrease the serum concentration of NSAID (Nonselective). Exceptions: Choline Magnesium Trisalicylate.
SpectinomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
StreptokinaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
StreptomycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
SulodexideAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
TenecteplaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
TenofovirNonsteroidal Anti-Inflammatory Agents may enhance the adverse/toxic effect of Tenofovir.
TeriflunomideMay increase the serum concentration of OAT3 Substrates.
TipranavirMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
TobramycinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TreprostinilAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
UrokinaseAgents with Antiplatelet Properties may enhance the anticoagulant effect of Thrombolytic Agents.
VancomycinNonsteroidal Anti-Inflammatory Agents may increase the serum concentration of Vancomycin.
VerteporfinPhotosensitizing Agents may enhance the photosensitizing effect of Verteporfin.
Vitamin EMay enhance the antiplatelet effect of Agents with Antiplatelet Properties.
WarfarinAgents with Antiplatelet Properties may enhance the anticoagulant effect of Anticoagulants.
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