Identification
- Summary
Ketoprofen is an NSAID used to treat rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, dysmenorrhea, mild to moderate muscle pain, postoperative pain, and postpartum pain.
- Generic Name
- Ketoprofen
- DrugBank Accession Number
- DB01009
- Background
Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Ketoprofen (DB01009)
- Weight
- Average: 254.2806
Monoisotopic: 254.094294314 - Chemical Formula
- C16H14O3
- 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
- External IDs
- IDEA-033
- R.P. 19,583
- R.P. 19583
- RP-19583
- RU-4733
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Ankylosing spondylitis •••••••••••• •••••••• •••••• Prophylaxis of Migraine ••• ••••• Treatment of Mild pain •••••••••••• •••••••• •••••• Treatment of Mild pain •••••••••••• •••••••• •••••• Symptomatic treatment of Osteoarthritis •••••••••••• •••••••• •••••••• •••••••• •••••••• ••••••• ••••••• •••••••• ••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans UProstaglandin G/H synthase 1 inhibitorHumans UC-X-C chemokine receptor type 1 otherHumans - 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.
Hover over products below to view reaction partners
- 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]
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- Pathways
Pathway Category Ketoprofen Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Ketoprofen may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Ketoprofen is combined with Abciximab. Acamprosate The excretion of Acamprosate can be decreased when combined with Ketoprofen. Acebutolol Ketoprofen may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Ketoprofen is combined with Aceclofenac. - Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ketoprofen lysine 5WD00E3D4C 57469-78-0 VHIORVCHBUEWEP-ZSCHJXSPSA-N Ketoprofen sodium 5R10M39KS7 57495-14-4 OAPDLBHLMVYMCW-UHFFFAOYSA-M - Product Images
- International/Other Brands
- Actron / Alrheumun (Teofarma) / Capisten (Kissei) / Epatec (Zeria Shinyaku) / Fastum (Menarini) / Menamin (Daiko Seiyaku) / Orudis (Abbott) / Orudis KT (Sanofi) / Orugesic (Sanofi) / Oscorel (Sanofi) / Profenid (Sanofi) / Toprec (Sanofi)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ketophene Kit 33.5 g/33.5g Topical California Pharmaceuticals, Llc 2016-01-01 Not applicable US 
Ketoprofen Capsule 50 mg/1 Oral Mylan Pharmaceuticals Inc. 2006-11-27 2006-11-27 US Ketoprofen Capsule 50 mg Oral Aa Pharma Inc 1989-12-31 Not applicable Canada 
Ketoprofen Capsule 75 mg/1 Oral Mylan Pharmaceuticals Inc. 2006-11-27 2006-11-27 US Ketoprofen SR Tablet, extended release 200 mg Oral Aa Pharma Inc 1995-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ketoprofen Capsule, extended release 150 mg/1 Oral Actavis Pharma Company 1999-03-24 2001-03-30 US Ketoprofen Capsule 50 mg/1 Oral Heritage Pharma Labs Inc. d/b/a Avet Pharmaceuticals Labs Inc. 2020-01-28 2022-01-31 US Ketoprofen Capsule 75 mg/1 Oral Av Kare, Inc. 2013-07-08 2016-02-02 US Ketoprofen Capsule 75 mg/1 Oral Preferred Pharmaceuticals, Inc. 2011-01-18 2019-10-09 US 
Ketoprofen Capsule 75 mg/1 Oral A S Medication Solutions 1993-01-01 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ALKETO PLASTER 30 MG Plaster 30.000 mg Topical LOTUS INTERNATIONAL PTE. LTD. 2016-04-15 Not applicable Singapore 
FASTUM GEL 2.5% Gel 2.5 g/100g Topical A. MENARINI SINGAPORE PTE. LTD. 1992-04-01 Not applicable Singapore FASTUM GEL MAX 2.5% Gel 2.5 g/100g Topical A. MENARINI SINGAPORE PTE. LTD. 2018-11-07 Not applicable Singapore KEFENTECH AIR 30 MG/SHEET Plaster 30 MG/SHEET Topical PHARMAFORTE SINGAPORE PTE LTD 2017-04-18 Not applicable Singapore KEFENTECH PLASTER 30 mg/sheet Plaster 30 mg Topical PHARMAFORTE SINGAPORE PTE LTD 1999-02-25 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BI-PROFENID Ketoprofen (75 mg) + Ketoprofen (75 mg) Tablet, extended release Oral SANOFI MEDLEY FARMACEUTICA LTDA. 2007-02-05 Not applicable Colombia 
BI-PROFENID Ketoprofen (75 mg) + Ketoprofen (75 mg) Tablet, extended release Oral SANOFI MEDLEY FARMACEUTICA LTDA. 2007-02-05 Not applicable Colombia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ketophene Ketoprofen (33.5 g/33.5g) Kit Topical California Pharmaceuticals, Llc 2016-01-01 Not applicable US Vopac - Ketoprofen, Lidocaine Hydrochloride Pac Ketoprofen (5.525 g/11.05g) Kit Topical Sircle Laboratories, Llc 2015-03-01 2015-06-30 US
Categories
- ATC Codes
- M01AE03 — Ketoprofen
- M01AE — Propionic acid derivatives
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- M02AA — Antiinflammatory preparations, non-steroids for topical use
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amino Acids
- Amino Acids, Basic
- Amino Acids, Diamino
- Amino Acids, Peptides, and Proteins
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antirheumatic Agents
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (weak)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Other Nonsteroidal Anti-inflammatory Agents
- Peripheral Nervous System Agents
- Phenylpropionates
- Photosensitizing Agents
- Propionates
- Sensory System Agents
- Topical Products for Joint and Muscular Pain
- UGT1A1 Substrates
- Chemical TaxonomyProvided by Classyfire
- 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
- 2-phenylpropanoic-acid / Aromatic homomonocyclic compound / Aryl ketone / Aryl-phenylketone / Benzophenone / Benzoyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Diphenylmethane
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzophenones, oxo monocarboxylic acid (CHEBI:6128)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 90Y4QC304K
- CAS number
- 22071-15-4
- 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
References
- Synthesis Reference
Attilio Citterio, Daniele Fancelli, "Method of preparing ketoprofen." U.S. Patent US4845281, issued December, 1982.
US4845281- General References
- External Links
- Human Metabolome Database
- HMDB0015144
- KEGG Drug
- D00132
- KEGG Compound
- C01716
- PubChem Compound
- 3825
- PubChem Substance
- 46505715
- ChemSpider
- 3693
- BindingDB
- 50022271
- 6142
- 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
- FDA label
- Download (160 KB)
- MSDS
- Download (75.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Supportive Care Other Surgical Procedures / Pain 1 4 Completed Treatment Ankle Sprains 1 4 Completed Treatment Back Pain Lower Back / Gonarthrosis 1 4 Completed Treatment Caesarian Section 1 4 Completed Treatment Cesarean Sections / Neuropathic Pain / Pain Management 1
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
Form Route Strength Granule, for solution Oral Plaster Topical 30.000 mg Aerosol, foam Topical 15 % Capsule Oral 160 MG Capsule Oral 320 mg Gel Topical 30 G Injection, powder, lyophilized, for solution Intramuscular 80 mg Injection, solution 160 MG/2ML Injection, solution Intramuscular; Intravenous 160 mg/2ml Tablet Oral 75.00 mg Tablet, extended release Oral Tablet Oral 150 mg Solution Intravenous 100.00 ml Suspension Oral Solution Intramuscular Capsule, extended release Oral 100 MG Injection, solution Intramuscular 100 MG/2ML Solution Oral Solution Parenteral 100.000 mg Solution Intramuscular; Intravenous 20 mg Gel Topical 25 mg Gel Cutaneous 2.500 g Capsule Oral 60 MG Injection, solution Intramuscular 50 mg/3ml Spray Cutaneous 25 MG/G Tablet Oral 25 MG Gel Topical Gel Topical 2.5 g/100g Solution Topical Injection, powder, for solution Intramuscular; Parenteral 100 MG/2.5ML Injection, powder, for solution Intravenous; Parenteral 100 MG Injection, solution Intramuscular 100 mg/5ml Injection, solution Intramuscular 50 mg/5ml Suppository Rectal 200 MG Capsule Oral 100 MG Capsule Oral 200 MG Cream Topical 1 % Gel Topical 50 MG/ML Granule, effervescent Oral 50 mg Injection, solution Intramuscular 100 MG/2.5ML Injection, solution Intramuscular 100 mg Injection, solution Intravenous 100 mg Injection, solution Intravenous 100 MG/5ML Solution Topical 5 % Solution Topical 50 mg Solution / drops Oral 25 MG/ML Suppository Rectal 75 MG Spray Oral Capsule, extended release Oral Dressing Topical Plaster Topical 30 MG/SHEET Plaster Transdermal 30 MG Solution Oral 40 MG Patch Topical Patch Topical 20 MG Injection, powder, for solution Intramuscular Injection, powder, for solution Intravenous Spray Topical 0.16 % Rinse Oral 1.6 % Tablet, extended release Oral 100 MG Tablet Oral Gel Topical 2.50 %w/w Kit Topical 33.5 g/33.5g Gel Topical 2.5 % W/W Capsule Oral 50 mg Tablet Oral 75 mg/1 Injection Intramuscular 50 MG/ML Tablet, extended release Oral 200 mg Suppository Rectal 50 mg / sup Tablet, delayed release Oral 100 mg Tablet, delayed release Oral 50 mg Tablet, extended release Oral 200 mg / tab Gel Topical 5 % Injection, solution Intramuscular; Parenteral 100 MG/2.5ML Spray Cutaneous 10 % Injection Intramuscular 100 MG Injection, powder, for solution 100 MG Tablet, effervescent 25 MG Tablet, orally disintegrating 40 MG Powder, for solution Oral 80 MG Cream Topical 5 % Suppository Rectal 120 MG Tablet Oral 80 MG Injection, solution Intramuscular; Parenteral 100 MG/2ML Capsule, liquid filled Oral 100 mg Capsule, liquid filled Oral 10000000 mg Solution Intramuscular; Intravenous 100 mg Solution Intravenous 100 mg Solution Intramuscular 100 mg Aerosol Topical 2.5 g Capsule, coated Oral 100 mg Gel Topical 2.5 g Injection Parenteral 100 mg Solution Parenteral 100 mg Tablet, coated Oral 10000000 mg Injection, solution Intramuscular; Intravenous Spray Topical Plaster Topical 30 mg Plaster Transdermal Gel Topical 250000 g Tablet, delayed release Oral Solution / drops Oral Tablet, coated Oral Gel Topical 2.500 g Suppository Rectal Solution Intramuscular 100 mg/2mL Tablet, delayed release Oral 100 mg / tab Tablet, delayed release Oral 50 mg / tab Tablet, delayed release Oral 100 mg / ect Tablet, delayed release Oral 50 mg / ect Aerosol, foam Topical 50 ML Capsule, extended release Oral 320 MG Gel Topical 15 % Granule, for solution Oral 40 MG Granule, for solution Oral 80 MG Injection, solution Intramuscular 160 MG/2ML Mouthwash Oral 1.6 % Solution Vaginal 500 MG Solution / drops Oral 80 MG/ML Spray Oral 0.16 % Suppository Rectal 160 MG Suppository Rectal 30 MG Suppository Rectal 60 MG Tablet, coated Oral 80 MG Granule Oral 80.000 mg Solution Oral 8.00 g Tablet, effervescent Granule Oral Granule Oral 40 mg Tablet, film coated Oral Granule Oral 25 mg Tablet, film coated Oral 25 mg Suppository Rectal 100 mg / sup Capsule Oral 150 MG Cream Topical 2.5 % Gel Topical 2.5 % Injection, powder, for solution Intramuscular 100 MG/2.5ML Injection, powder, for solution Intravenous 100 MG/5ML Tablet Oral 100 mg Suppository Rectal 50 mg Capsule Oral 25 mg/1 Capsule Oral 50 mg/1 Capsule Oral 75 mg/1 Capsule, extended release Oral 150 mg / cap Capsule, extended release Oral 200 mg / cap Capsule, extended release Oral 100 mg/1 Capsule, extended release Oral 150 mg/1 Capsule, extended release Oral 200 mg/1 Capsule Oral 100.000 mg Suppository Rectal 100 mg Tablet, delayed release Oral 10000000 mg Syrup Oral 1 mg/ml Injection, solution Intramuscular Capsule Oral Tablet Oral 200 mg Injection, solution, concentrate Parenteral Tablet, delayed release Oral 200 mg Powder, for suspension Oral 100 mg Granule Oral 50 mg Capsule, liquid filled Oral 50 mg Tablet Oral 200.000 mg Suppository Rectal 0.1 g Syrup Oral 100 mg Injection, powder, lyophilized, for solution Intravenous 100 mg Tablet, coated Oral 100 mg Tablet, coated Oral 50 mg Solution 100.00 mg Injection Intramuscular Tablet Oral 250.000 mg Injection, powder, for solution Gel Topical 25 MG/G Capsule Oral 50 mg / cap Tablet, extended release Oral 200 mg / srt Capsule, extended release Oral 150 mg Capsule, extended release Oral 200 mg Mouthwash Oral Spray Oral 16 MG/ML Capsule, coated Oral 50 mg Cream Topical Powder, for solution Oral Tablet Oral Solution Parenteral 100.000 mg Kit Topical 5.525 g/11.05g Solution Intramuscular 100.000 mg Spray Cutaneous 100 MG/G Gel Topical 2.5 %w/w Powder 100 mg/1ampoule Solution 50 mg/1ml - Prices
Unit description Cost Unit Ketoprofen powder 43.74USD g Ketoprofen micronized powder 3.84USD g Ketoprofen CR 200 mg 24 Hour Capsule 2.8USD capsule Orudis 75 mg capsule 1.58USD capsule Apo-Keto Sr 200 mg Sustained-Release Tablet 1.46USD tablet Ketoprofen 75 mg capsule 1.12USD capsule Pms-Ketoprofen 100 mg Suppository 1.1USD suppository Ketoprofen 50 mg capsule 1.0USD capsule Apo-Keto-E 100 mg Enteric-Coated Tablet 0.71USD tablet Apo-Keto 50 mg Capsule 0.35USD capsule Apo-Keto-E 50 mg Enteric-Coated Tablet 0.35USD tablet Orudis kt 12.5 mg tablet 0.3USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 94 °C U.S. Patent 3,641,127. water solubility 51 mg/L (at 22 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.12 SANGSTER (1993) logS -3.7 ADME Research, USCD pKa 4.45 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0213 mg/mL ALOGPS logP 3.29 ALOGPS logP 3.61 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 3.88 Chemaxon pKa (Strongest Basic) -7.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 54.37 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 72.52 m3·mol-1 Chemaxon Polarizability 26.56 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9928 Blood Brain Barrier + 0.9382 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.7132 P-glycoprotein inhibitor I Non-inhibitor 0.9168 P-glycoprotein inhibitor II Non-inhibitor 0.9589 Renal organic cation transporter Non-inhibitor 0.8818 CYP450 2C9 substrate Non-substrate 0.7183 CYP450 2D6 substrate Non-substrate 0.9598 CYP450 3A4 substrate Non-substrate 0.7685 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9604 CYP450 2C19 inhibitor Non-inhibitor 0.9465 CYP450 3A4 inhibitor Non-inhibitor 0.9598 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9438 Ames test Non AMES toxic 0.9801 Carcinogenicity Non-carcinogens 0.6299 Biodegradation Ready biodegradable 0.6701 Rat acute toxicity 2.2378 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9661 hERG inhibition (predictor II) Non-inhibitor 0.9595
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.7400043 predictedDarkChem Lite v0.1.0 [M-H]- 157.23738 predictedDeepCCS 1.0 (2019) [M+H]+ 175.7465043 predictedDarkChem Lite v0.1.0 [M+H]+ 159.63298 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.2417043 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.68735 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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. [Article]
- Glowka F, Karazniewicz-Lada M, Grzeskowiak E, Rogozinska D, Romanowski W: Clinical pharmacokinetics of ketoprofen enantiomers in wild type of Cyp 2c8 and Cyp 2c9 patients with rheumatoid arthritis. Eur J Drug Metab Pharmacokinet. 2011 Sep;36(3):167-73. doi: 10.1007/s13318-011-0041-1. Epub 2011 Apr 24. [Article]
- EMA Withdrawal Assessment Report for Direction (Ketoprofen Gel) [File]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Glowka F, Karazniewicz-Lada M, Grzeskowiak E, Rogozinska D, Romanowski W: Clinical pharmacokinetics of ketoprofen enantiomers in wild type of Cyp 2c8 and Cyp 2c9 patients with rheumatoid arthritis. Eur J Drug Metab Pharmacokinet. 2011 Sep;36(3):167-73. doi: 10.1007/s13318-011-0041-1. Epub 2011 Apr 24. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Dancygier H. (2010). Clinical Hepatology. Springer-Verlag. [ISBN:978-3-642-04509-7]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Bertucci C: Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate. Chirality. 2001 Jul;13(7):372-8. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55