Details
Stereochemistry | EPIMERIC |
Molecular Formula | C16H14O3.C6H14N2O2 |
Molecular Weight | 400.4681 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC[C@H](N)C(O)=O.CC(C(O)=O)C1=CC=CC(=C1)C(=O)C2=CC=CC=C2
InChI
InChIKey=VHIORVCHBUEWEP-ZSCHJXSPSA-N
InChI=1S/C16H14O3.C6H14N2O2/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12;7-4-2-1-3-5(8)6(9)10/h2-11H,1H3,(H,18,19);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21052564https://www.drugs.com/international/dexketoprofen.htmlCurator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02159547 | https://www.ncbi.nlm.nih.gov/pubmed/28540716 | https://clinicaltrials.gov/ct2/show/NCT03122314 | https://www.ncbi.nlm.nih.gov/pubmed/28326850 | https://clinicaltrials.gov/ct2/show/NCT02092012
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21052564https://www.drugs.com/international/dexketoprofen.html
Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02159547 | https://www.ncbi.nlm.nih.gov/pubmed/28540716 | https://clinicaltrials.gov/ct2/show/NCT03122314 | https://www.ncbi.nlm.nih.gov/pubmed/28326850 | https://clinicaltrials.gov/ct2/show/NCT02092012
Dexketoprofen is a nonsteroidal anti-inflammatory drug (NSAID), manufactured by Menarini under the tradename Keral. Dexketoprofen is indicated for short-term treatment of mild to moderate pain, including dysmenorrhoea. Dexketoprofen works by blocking the action of a substance in the body called cyclo-oxygenase, which is involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would otherwise go on to cause swelling, inflammation, and pain. By blocking cyclo-oxygenase, dexketoprofen prevents the production of prostaglandins and therefore reduces inflammation and pain. Along with peripheral analgesic action, it possesses central analgesic action. Dexketoprofen may cause dizziness, and patients should not, therefore, drive or operate heavy machinery or vehicles until they are familiar with how dexketoprofen affects them. Concomitant use of alcohol and other sedatives may potentiate this effect. In a small subset of individuals, the dizziness may be intolerable and require the transition to an alternative treatment.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4076328
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/9176993
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3526298ZA6800524
Curator's Comment: 1967
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807 |
1.9 nM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807 |
27.0 nM [IC50] | ||
Target ID: CHEMBL2096909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15974585 |
50.0 nM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637 |
0.52 µM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637 |
0.019 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Keral Approved UseUnknown |
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Primary | Keral Approved UseUnknown |
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Primary | Keral Approved UseUnknown |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.91 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
12.5 mg single, oral Dose: 12.5 mg Route: oral Route: single Dose: 12.5 mg Sources: Page: p. 34 |
unhealthy, 36.8 years (range: 18 - 65 years) n = 90 Health Status: unhealthy Age Group: 36.8 years (range: 18 - 65 years) Sex: M+F Population Size: 90 Sources: Page: p. 34 |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (mild, 1 patient) Sources: Page: p. 34 |
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: |
Other AEs: Epigastric pain... Other AEs: Epigastric pain (mild, 1 patient) Sources: |
100 mg 1 times / day multiple, topical Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult n = 172 Health Status: unhealthy Condition: tendinitis Age Group: adult Population Size: 172 Sources: |
|
100 ug 3 times / day steady, oral (max) Dose: 100 ug, 3 times / day Route: oral Route: steady Dose: 100 ug, 3 times / day Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: Lymphedema Population Size: 50 Sources: |
Other AEs: Cellulitis... Other AEs: Cellulitis (below serious, 3 patients) Sources: |
75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 19 Health Status: unhealthy Condition: Lymphedema Population Size: 19 Sources: |
Other AEs: Rash... |
75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 23 Health Status: unhealthy Condition: Lymphedema Population Size: 23 Sources: |
Other AEs: Cellulitis... Other AEs: Cellulitis (below serious, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Rash | mild, 1 patient Disc. AE |
12.5 mg single, oral Dose: 12.5 mg Route: oral Route: single Dose: 12.5 mg Sources: Page: p. 34 |
unhealthy, 36.8 years (range: 18 - 65 years) n = 90 Health Status: unhealthy Age Group: 36.8 years (range: 18 - 65 years) Sex: M+F Population Size: 90 Sources: Page: p. 34 |
Epigastric pain | mild, 1 patient | 2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: |
Cellulitis | below serious, 3 patients | 100 ug 3 times / day steady, oral (max) Dose: 100 ug, 3 times / day Route: oral Route: steady Dose: 100 ug, 3 times / day Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: Lymphedema Population Size: 50 Sources: |
Rash | below serious, 1 patient | 75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 19 Health Status: unhealthy Condition: Lymphedema Population Size: 19 Sources: |
Cellulitis | below serious, 1 patient | 75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 23 Health Status: unhealthy Condition: Lymphedema Population Size: 23 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 1.3 uM] | ||||
yes [IC50 1.4 uM] | ||||
yes [IC50 11.9 uM] | ||||
yes [IC50 400 uM] | ||||
yes [IC50 5.98 uM] | ||||
yes [IC50 70.3 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/19422321/ Page: 2.0 |
minor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Iatrogenic cost factors incorporating mild and moderate adverse events in the economic comparison of aceclofenac and other NSAIDs. | 2001 |
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Aceclofenac: a reappraisal of its use in the management of pain and rheumatic disease. | 2001 |
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Use of continuous fluid drainage for severe polyhydramnios due to twin to twin transfusion syndrome. | 2001 |
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[Two complex suicidal poisonings with drugs and their medicolegal aspects]. | 2001 |
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Early-morning administration of dexketoprofen-trometamol in morning stiffness induced by nodal osteoarthritis of the hands. | 2001 |
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Release behavior of ketoprofen from poly(acryloyl-L-proline methyl ester) gels having different crosslinked networks. | 2001 |
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Clinical pharmacokinetics of dexketoprofen. | 2001 |
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Overdose of ketoprofen could be dangerous. | 2001 Apr |
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Interaction between the antinociceptive effect of ketoprofen and adrenergic modulatory systems. | 2001 Aug |
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Simultaneous optimization based on artificial neural networks in ketoprofen hydrogel formula containing O-ethyl-3-butylcyclohexanol as percutaneous absorption enhancer. | 2001 Aug |
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Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis. | 2001 Aug |
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Investigation of the utility of an in vitro release test for optimizing semisolid dosage forms. | 2001 Aug |
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Sustained release ketoprofen microparticles with ethylcellulose and carboxymethylethylcellulose. | 2001 Aug 10 |
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In vitro distribution of ketoprofen enantiomers in articular tissues of osteoarthritic patients. | 2001 Dec |
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Oral ketoprofen in children--could it have been done differently? | 2001 Jan |
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Cytokines and cytokine inducers stimulate prostaglandin E2 entry into the brain. | 2001 Jul |
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Comparison of tissue concentrations after intramuscular and topical administration of ketoprofen. | 2001 Jul |
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[Enantiomeric separation of drugs based on macrocyclic antibiotics]. | 2001 Jul |
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Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study. | 2001 Jul 17 |
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Stereoselective pharmacokinetics of ketoprofen in llamas following intravenous administration. | 2001 Jun |
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Enantiospecific pharmacokinetics of ketoprofen in plasma and synovial fluid of horses with acute synovitis. | 2001 Jun |
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Safety and efficacy of preoperative administration of meloxicam, compared with that of ketoprofen and butorphanol in dogs undergoing abdominal surgery. | 2001 Jun |
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Simultaneous photocontact sensitivity to ketoprofen and oxybenzone. | 2001 Jun |
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Selective inhibition of interleukin-8-induced neutrophil chemotaxis by ketoprofen isomers. | 2001 Jun 1 |
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Intercalation compounds of hydrotalcite-like anionic clays with antiinflammatory agents--I. Intercalation and in vitro release of ibuprofen. | 2001 Jun 4 |
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Preparation and evaluation of ketoprofen floating oral delivery system. | 2001 Jun 4 |
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[Acute pancreatitis and ketoprofen]. | 2001 Jun-Jul |
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[Ketoprofen-induced acute hepatitis]. | 2001 Jun-Jul |
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I.v. ketoprofen for analgesia after tonsillectomy: comparison of pre- and post-operative administration. | 2001 Mar |
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Thoracoscopy as a nonpharmacotherapeutic research modification for limiting postoperative chest pain. | 2001 Mar-Apr |
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Effect of oxidative stress on the structure and function of human serum albumin. | 2001 May |
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Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee. | 2001 May |
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An oral controlled release matrix pellet formulation containing nanocrystalline ketoprofen. | 2001 May 21 |
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Onset of analgesia for liquigel ibuprofen 400 mg, acetaminophen 1000 mg, ketoprofen 25 mg, and placebo in the treatment of postoperative dental pain. | 2001 Nov |
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Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry. | 2001 Oct |
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Influence of betacyclodextrin on the release of poorly soluble drugs from inert and hydrophilic heterogeneous polymeric matrices. | 2001 Oct |
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Lipopolysaccharide-induced increase of prostaglandin E(2) is mediated by inducible nitric oxide synthase activation of the constitutive cyclooxygenase and induction of membrane-associated prostaglandin E synthase. | 2001 Oct 1 |
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Effects of diclofenac and ketoprofen on nerve conduction velocity in experimental nerve root compression. | 2001 Oct 15 |
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Optimized conditions of bio-mimetic artificial membrane permeation assay. | 2001 Oct 9 |
|
Transdermal delivery of ketoprofen using microemulsions. | 2001 Oct 9 |
|
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility]. | 2001 Sep |
|
Efficacy and safety of ketoprofen lysine salt mouthwash versus benzydamine hydrochloride mouthwash in acute pharyngeal inflammation: a randomized, single-blind study. | 2001 Sep |
|
Comparison of the effects of ketoprofen on platelet function in the presence and absence of aspirin. | 2001 Sep |
|
Promoting mechanism of menthol derivative, 1-O-ethyl-3-buthylcyclohexanol, on the percutaneous absorption of ketoprofen. | 2001 Sep |
|
Incompatibility of prochlorperizine and ketoprofen. | 2001 Sep |
|
Photocontact dermatitis to ketoprofen. | 2001 Sep |
|
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats. | 2001 Sep |
|
Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells. | 2001 Sep |
|
In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac. | 2001 Sep |
|
Enhancement of the activity of doxorubicin by inhibition of glutamate transporter. | 2001 Sep 15 |
Patents
Sample Use Guides
Rheumatoid Arthritis and Osteoarthritis: 75 mg three times or 50 mg four times a day. The recommended maximum daily dose of ketoprofen capsules is 300 mg/day.
Pain and Dysmenorrhea: 25 to 50 mg every 6 to 8 hours as necessary.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18565185
Curator's Comment: In cultivation of freshly isolated epidermal cells, 5 mM Ketoprofen inhibited the culture-promoted expression of PCl-augmented expression of major histocompatibility complex class II and CD86 on Langerhans cells
5 mM Ketoprofen (mouse isolated epidermal cells)
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100000092575
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SUB02834MIG
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m6622
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DTXSID40972999
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5WD00E3D4C
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28199
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9822313
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD