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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- 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
Structure for Ketoprofen (DB01009)
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Ketoprofen sodium 5R10M39KS7 57495-14-4 OAPDLBHLMVYMCW-UHFFFAOYSA-M - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataKetophene Kit 33.5 g/33.5g Topical California Pharmaceuticals, Llc 2016-01-01 Not applicable 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 Capsule 50 mg/1 Oral Mylan Pharmaceuticals Inc. 2006-11-27 2006-11-27 US Ketoprofen SR Tablet, extended release Oral Aa Pharma Inc 1995-12-31 Not applicable Canada Ketoprofen Suppositories Suppository Rectal Pharmel Inc 1998-06-04 1998-06-04 Canada Ketoprofen Suppositories Suppository Rectal Pharmel Inc Not applicable Not applicable Canada Ketoprofen-E Tablet, delayed release Oral Aa Pharma Inc 1989-12-31 Not applicable Canada Ketoprofen-E Tablet, delayed release Oral Aa Pharma Inc 1989-12-31 Not applicable Canada Ketoprofen-E Ect 100mg Tablet, delayed release Oral Pro Doc Limitee 1996-12-31 2009-07-23 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataKetoprofen Capsule 50 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1993-01-01 Not applicable US Ketoprofen Capsule 75 mg/1 Oral Stat Rx USA 2011-01-18 Not applicable US Ketoprofen Capsule, extended release 100 mg/1 Oral Actavis Pharma Company 1999-03-24 2001-03-30 US Ketoprofen Capsule 50 mg/1 Oral Avera McKennan Hospital 2015-10-28 2018-07-05 US Ketoprofen Capsule 75 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1993-01-01 2018-08-28 US Ketoprofen Capsule 50 mg/1 Oral Stat Rx USA 2011-01-18 Not applicable US Ketoprofen Capsule 50 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1997-01-15 2018-08-02 US Ketoprofen Capsule 50 mg/1 Oral Aidarex Pharmaceuticals LLC 1993-01-01 Not applicable US Ketoprofen Capsule 75 mg/1 Oral Rebel Distributors 2010-04-20 Not applicable US Ketoprofen Capsule 75 mg/1 Oral Preferred Pharmaceuticals, Inc. 2011-01-18 Not applicable US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 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 - 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)
- Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- 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
- Central Nervous System 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 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
- Propionates
- Sensory System Agents
- Topical Products for Joint and Muscular Pain
- UGT1A1 Substrates
- 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.
Target Actions Organism UProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 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.
- 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
Pathway Category Ketoprofen Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- 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 Unlock Additional Data(R)-warfarin The risk or severity of bleeding and hemorrhage can be increased when Ketoprofen is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding and hemorrhage can be increased when Ketoprofen is combined with (S)-Warfarin. 1-benzylimidazole The risk or severity of hypertension can be increased when Ketoprofen is combined with 1-benzylimidazole. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of hypertension can be increased when Ketoprofen is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of hypertension can be increased when Ketoprofen is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of hypertension can be increased when Ketoprofen is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-hydroxycoumarin The risk or severity of bleeding and hemorrhage can be increased when Ketoprofen is combined with 4-hydroxycoumarin. 4-Methoxyamphetamine The risk or severity of hypertension can be increased when Ketoprofen is combined with 4-Methoxyamphetamine. 5-(2-methylpiperazine-1-sulfonyl)isoquinoline The risk or severity of adverse effects can be increased when Ketoprofen is combined with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline. 5-methoxy-N,N-dimethyltryptamine The risk or severity of hypertension can be increased when Ketoprofen is combined with 5-methoxy-N,N-dimethyltryptamine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
References
- Synthesis Reference
Attilio Citterio, Daniele Fancelli, "Method of preparing ketoprofen." U.S. Patent US4845281, issued December, 1982.
US4845281- General References
- Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. [PubMed:3526298]
- 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
- RxNav
- 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
- 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
- AHFS Codes
- 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
- FDA label
- Download (160 KB)
- MSDS
- Download (75.9 KB)
Clinical Trials
- Clinical Trials
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 Kit Topical 33.5 g/33.5g Capsule Oral 50 mg Tablet Oral 75 mg/1 Tablet, extended release Oral Tablet, delayed release Oral Capsule Oral Capsule Oral 25 mg/1 Capsule Oral 50 mg/1 Capsule Oral 75 mg/1 Capsule, extended release Oral Capsule, extended release Oral 100 mg/1 Capsule, extended release Oral 150 mg/1 Capsule, extended release Oral 200 mg/1 Suppository Rectal Kit Topical 5.525 g/11.05g - 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
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
- 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. [PubMed:10929089]
- 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]
- 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]
- 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]
- 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
- 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. [PubMed:10895904]
- 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]
- 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]
- 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]
- 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]
- 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
- 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. [PubMed:15974585]
- 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]
- 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
- 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. [PubMed:19515014]
- 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. [PubMed:21516380]
- 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. [PubMed:26721703]
- 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. [PubMed:21516380]
- 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. [PubMed:11400191]
- 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]
- 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]
- 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
- 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. [PubMed:12835412]
- 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. [PubMed:11883641]
- 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. [PubMed:10929807]
- 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]
- 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]
- 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]
- 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
- 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. [PubMed:12130730]
- 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
- 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. [PubMed:12130730]
- 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. [PubMed:9650585]
- 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]
- 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]
- 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 April 06, 2020 22:10
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