Identification

Name
Ketoprofen
Accession Number
DB01009  (APRD01059, DB05823, DB05335)
Type
Small Molecule
Groups
Approved, Vet approved
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
  • Ketoprofeno
  • L'Acide (benzoyl-3-phenyl)-2-propionique
  • m-Benzoylhydratropic acid
  • Orudis (tn)
Product Ingredients
IngredientUNIICASInChI Key
Ketoprofen sodium5R10M39KS757495-14-4OAPDLBHLMVYMCW-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
KetoprofenCapsule50 mgOralAa Pharma Inc1989-12-31Not applicableCanada
KetoprofenCapsule75 mg/1OralMylan Pharmaceuticals Inc.2006-11-272006-11-27Us
KetoprofenCapsule50 mg/1OralMylan Pharmaceuticals Inc.2006-11-272006-11-27Us
Ketoprofen SRTablet, extended release200 mgOralAa Pharma Inc1995-12-31Not applicableCanada
Ketoprofen SuppositoriesSuppository100 mgRectalPharmel Inc1998-06-04Not applicableCanada
Ketoprofen SuppositoriesSuppository50 mgRectalPharmel IncNot applicableNot applicableCanada
Ketoprofen-ETablet, delayed release100 mgOralAa Pharma Inc1989-12-31Not applicableCanada
Ketoprofen-ETablet, delayed release50 mgOralAa Pharma Inc1989-12-31Not applicableCanada
Ketoprofen-E Ect 100mgTablet, delayed release100 mgOralPro Doc Limitee1996-12-312009-07-23Canada
Ketoprofen-E Ect 50mgTablet, delayed release50 mgOralPro Doc Limitee1995-12-312009-07-23Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
KetoprofenCapsule75 mg/1OralAv Kare, Inc.2013-07-082016-02-02Us
KetoprofenCapsule, extended release200 mg/1OralActavis Pharma Company1999-03-242007-05-31Us
KetoprofenCapsule50 mg/1OralPhysicians Total Care, Inc.1997-02-14Not applicableUs
KetoprofenCapsule25 mg/1OralHeritage2018-06-14Not applicableUs
KetoprofenCapsule75 mg/1OralRebel Distributors2010-04-20Not applicableUs
KetoprofenCapsule75 mg/1OralPD-Rx Pharmaceuticals, Inc.1993-01-012018-08-28Us
KetoprofenCapsule, extended release200 mg/1OralPhysicians Total Care, Inc.2009-06-23Not applicableUs00378 8200 01 nlmimage10 183e8c44
KetoprofenCapsule50 mg/1OralMesource Pharmaceuticals1993-01-01Not applicableUs
KetoprofenCapsule75 mg/1OralStat Rx USA2011-01-18Not applicableUs
KetoprofenCapsule75 mg/1OralTeva Pharmaceuticals USA, Inc.1993-01-01Not applicableUs0093 319520180814 13942 1jsm6g0
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
KetopheneKetoprofen (33.5 g/33.5g)KitCalifornia Pharmaceuticals, Llc2016-01-01Not applicableUs
Vopac - Ketoprofen, Lidocaine Hydrochloride PacKetoprofen (5.525 g/11.05g)KitSircle Laboratories, Llc2015-03-012015-06-30Us
International/Other Brands
Actron / Alrheumun (Teofarma) / Capisten (Kissei) / Epatec (Zeria Shinyaku) / Fastum (Menarini) / Menamin (Daiko Seiyaku) / Orudis (Abbott) / Orudis KT (Sanofi) / Orugesic (Sanofi) / Oruvail (Wyeth) / Oscorel (Sanofi) / Profenid (Sanofi) / Toprec (Sanofi)
Categories
UNII
90Y4QC304K
CAS number
22071-15-4
Weight
Average: 254.2806
Monoisotopic: 254.094294314
Chemical Formula
C16H14O3
InChI Key
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

Pharmacology

Indication

For 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.

Associated Conditions
Pharmacodynamics

Ketoprofen 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 action

The 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.

TargetActionsOrganism
UProstaglandin G/H synthase 1
inhibitor
Human
AProstaglandin G/H synthase 2
inhibitor
Human
UC-X-C chemokine receptor type 1
other
Human
Absorption

Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.

Volume of distribution
Not Available
Protein binding

99% bound, primarily to albumin

Metabolism

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

Route of elimination

In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.

Half life

Conventional 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]
Toxicity

LD50=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
Pathways
PathwayCategory
Ketoprofen Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Ketoprofen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Ketoprofen is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Ketoprofen is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when Ketoprofen is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when Ketoprofen is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Ketoprofen is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of hypertension can be increased when Ketoprofen is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when Ketoprofen is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Ketoprofen is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when Ketoprofen is combined with 4-Methoxyamphetamine.
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.

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:3526298]
  2. Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. [PubMed:16274258]
External Links
Human Metabolome Database
HMDB0015144
KEGG Drug
D00132
KEGG Compound
C01716
PubChem Compound
3825
PubChem Substance
46505715
ChemSpider
3693
BindingDB
50022271
ChEBI
6128
ChEMBL
CHEMBL571
Therapeutic Targets Database
DAP000623
PharmGKB
PA450149
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ketoprofen
ATC Codes
M01AE53 — Ketoprofen, combinationsM02AA10 — KetoprofenM01AE03 — Ketoprofen
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
FDA label
Download (160 KB)
MSDS
Download (75.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentPainful musculoskeletal conditions1
1RecruitingTreatmentRenal Colic1
2CompletedNot AvailableKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentTendonitis of the Shoulder, Elbow, or Knee1
2RecruitingTreatmentNeoplasms, Upper Aerodigestive Tract / Uterine Cervical Cancer1
2Unknown StatusTreatmentPost-Operative Pain / Surgery, Cardiac1
2, 3CompletedTreatmentFemale Genital Diseases1
3CompletedNot AvailableAnkle Sprains1
3CompletedPreventionMigraines1
3CompletedPreventionPain Relief2
3CompletedTreatmentAcute Soft Tissue Injury / Muscle Strain / Sprains1
3CompletedTreatmentAnkle Sprains1
3CompletedTreatmentBack Pain Lower Back1
3CompletedTreatmentBursitis / Tendonitis1
3CompletedTreatmentKnee Osteoarthritis (Knee OA)1
3CompletedTreatmentMuscle Strain / Sprains1
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentPain NOS3
3Not Yet RecruitingTreatmentPainful musculoskeletal conditions2
3RecruitingTreatmentAcute Traumatic Pain1
3RecruitingTreatmentPost-Operative Nausea and Vomiting (PONV)1
3TerminatedTreatmentBursitis / Tendonitis1
3Unknown StatusTreatmentMuscular Atrophy / Sprains / Tendonitis1
3WithdrawnTreatmentAcute Pain (Flare) Associated With Osteoarthritis (OA) of the Knee1
3WithdrawnTreatmentMigraines1
3WithdrawnTreatmentSprains1
4CompletedSupportive CareOther Surgical Procedures / Pain NOS1
4CompletedTreatmentAnkle Sprains1
4CompletedTreatmentBack Pain Lower Back / Gonarthrosis1
4CompletedTreatmentCaesarian Section1
4CompletedTreatmentChildren / Postoperative pain / Recovery of Function1
4CompletedTreatmentGeneral Surgery1
4CompletedTreatmentPain NOS1
4CompletedTreatmentSciatica1
4CompletedTreatmentLymphedema of the extremities1
4Not Yet RecruitingTreatmentCesarean Section / Pain, Neuropathic / Postoperative pain1
4Not Yet RecruitingTreatmentCesarean Section / Postoperative pain1
4RecruitingTreatmentAnkle Sprains1
4RecruitingTreatmentCesarean Section / Pain Management / Pain, Neuropathic1
4RecruitingTreatmentMechanical Low Back Pain1
4SuspendedTreatmentAcute Renal Colic / Renal Colic1
4TerminatedTreatmentAnalgesia, Postoperative1
4TerminatedTreatmentPharyngotonsillitis1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1
Not AvailableCompletedTreatmentMigraines1
Not AvailableCompletedTreatmentPregnancy Termination1

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
  • Aidarex Pharmacuticals LLC
  • Apothecary Shop Wholesale
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Elan Pharmaceuticals Inc.
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Letco Medical Inc.
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharma Pac LLC
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prescription Dispensing Service Inc.
  • Professional Co.
  • Qualitest
  • Rebel Distributors Corp.
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
Kit33.5 g/33.5g
CapsuleOral50 mg
TabletOral75 mg/1
Tablet, extended releaseOral200 mg
Tablet, delayed releaseOral100 mg
Tablet, delayed releaseOral50 mg
SuppositoryRectal50 mg
CapsuleOral25 mg/1
CapsuleOral50 mg/1
CapsuleOral75 mg/1
Capsule, extended releaseOral150 mg
Capsule, extended releaseOral200 mg
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral150 mg/1
Capsule, extended releaseOral200 mg/1
SuppositoryRectal100 mg
Kit5.525 g/11.05g
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)94 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0390000000-a31eea165d399e00a838
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-520a79bdaf7ce3ec476c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-3aa1f85f9b6550cc9147
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-d582a4bd39cf003e73e3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-5a1b8d289986b0103991
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0390000000-66208a90d621bcbafe58
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0900000000-e3e8663a70e4a78219d3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-adc690db13d79d7e088b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-dc927e8f8991af0b9c62
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0090000000-2f4539685044ce030904
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0002-0900000000-ef4640dd80e9b12e93de
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-c153f6a533277453ee05
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-b4720ed0a7abab74acb0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0090000000-e4776b39ad9777a106d6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0190000000-cd73850fa213100eea4f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a6u-0940000000-b2b661b497cc37bb54d7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-60f88de41010fba22c8b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-8b462ef2178ab7ffdf4f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290000000-a6f4442004890a1099fa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0960000000-ea2a1b4ccfd466afd1d7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-ffa78d310365a0a9dd0e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-3f15ff6dad9be8084701
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a6r-5900000000-0e2bf00920a7e1627e89
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-4894675edf8eca790257
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0290000000-c4ff029474813952fb93
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0960000000-fd0fa1645957bec680d0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-1eb5023e779f64d2c54c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-e94235cda691beca3668
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a6r-5900000000-e7c564751c1ab453ec7d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-3c2483071b054192073e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0910000000-03f114a8dcdd26a59b2c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a6r-3900000000-456c7673c9f0423e5676
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-bfc6ecc839166fb81ec4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-9feded821a3159f1a9be
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0690000000-96f041a385b1f0080005
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0910000000-ad714bb911021f04971b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0pb9-0900000000-0c0d84c0eaff25680e89
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0490000000-39b45e31d0deb851ba88
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2490000000-437617eb0a03874b42b5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-3910000000-f7e3f020e942509b83e3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0890000000-abbc4b713cf8dac1afc9

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzophenones
Direct Parent
Benzophenones
Alternative Parents
Diphenylmethanes / Aryl-phenylketones / Phenylpropanoic acids / Benzoyl derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Benzophenone / Aryl-phenylketone / Diphenylmethane / 2-phenylpropanoic-acid / Benzoyl / Aryl ketone / Ketone / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzophenones, oxo monocarboxylic acid (CHEBI:6128)

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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
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:10929089]
  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:11811354]
  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:14513718]
  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:14987823]
  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:15476667]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. 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:10895904]
  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:11729362]
  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:11814865]
  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:14513718]
  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:15198222]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other
General Function
Interleukin-8 receptor activity
Specific Function
Receptor to interleukin-8, which is a powerful neutrophils chemotactic factor. Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activ...
Gene Name
CXCR1
Uniprot ID
P25024
Uniprot Name
C-X-C chemokine receptor type 1
Molecular Weight
39790.735 Da
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:15974585]
  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:11331079]
  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:9093816]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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:19515014]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. EMA Withdrawal Assessment Report for Direction (Ketoprofen Gel) [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Dancygier H. (2010). Clinical Hepatology. Springer-Verlag. [ISBN:978-3-642-04509-7]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bertucci C: Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. Chirality. 2001 Jul;13(7):372-8. [PubMed:11400191]
  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:11022905]
  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:12725696]
  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:15807110]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
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:12835412]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
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:11883641]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
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:10929807]
  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:10991954]
  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:12130730]
  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:11099697]
  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:10220563]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
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:12130730]
  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:12358729]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
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:12130730]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
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:9650585]
  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:11504818]
  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:10991954]
  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:12130730]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 17:08