Identification
- Summary
Dexketoprofen is an NSAID that is the R(-)-enantiomer of racemic ketoprofen with analgesic and anti-inflammatory properties used for the treatment of mild to moderate pain.
- Generic Name
- Dexketoprofen
- DrugBank Accession Number
- DB09214
- Background
Dexketoprofen is a non-steroidal anti-inflammatory drug. It is available in the various countries in Europe, Asia and Latin America. It has analgesic, antipyretic and anti-inflammatory properties 2.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Dexketoprofen (DB09214)
- Weight
- Average: 254.2806
Monoisotopic: 254.094294314 - Chemical Formula
- C16H14O3
- Synonyms
- Dexketoprofen
- Dexketoprofeno
Pharmacology
- Indication
For short-term treatment of mild to moderate pain, including dysmenorrhoea, musculoskeletal pain and toothache 6.
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 Treatment of Ankylosing spondylitis (as) •••••••••••• Used in combination to treat Extra-articular rheumatism Combination Product in combination with: Thiocolchicoside (DB11582) •••••••••••• ••••••• •••••• Treatment of Gouty arthritis •••••••••••• Treatment of Inflammatory reaction •••••••••••• Used in combination to manage Local pain Combination Product in combination with: Thiocolchicoside (DB11582) •••••••••••• ••••••••••••••• •••••••••• ••••••••• ••••••••• •••• •••••• •••••• ••••• - 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
This drug is an isomer of ketoprofen. Dexketoprofen a propionic acid derivative with analgesic, anti-inflammatory, and antipyretic properties 3.
- Mechanism of action
It is a non-steroidal anti-inflammatory drug (NSAID) that reduces prostaglandin synthesis via inhibition of cyclooxygenase pathway (both COX-1 and COX-2) activity 3.
Target Actions Organism UProstaglandin G/H synthase 1 antagonistHumans UProstaglandin G/H synthase 2 antagonistHumans - Absorption
After oral ingestion, the Dexketoprofen onset of action is within 30 minutes. The plasma half-life of Dexketoprofen is about 4-6 hours. The Cmax is about 30 minutes 7
- Volume of distribution
<0.25 L/kg 3
- Protein binding
Highly protein bound 3.
- Metabolism
Dexketoprofen is highly lipophilic, and is metabolized in the liver by glucuronidation 7. In one study, after oral administration of 25 mg of dexketoprofen to young healthy adults, Tmax was approximately 30 min for a Cmax of 3.7 ± 0.72 mg/l 8. Dexketoprofen trometamol is metabolized by the hepatic cytochrome P450 enzymes (CYP2C8 and CYP2C9) 8.
Dexketoprofen trometamol has a number of metabolites, with hydroxyl derivatives making up the greatest volume 8. In humans, hydroxylation plays a minor role.
Dexketoprofen is primarily conjugated to an acyl-glucuronide 8
- Route of elimination
Approximately 70 to 80% of the ingested dose is recovered in the urine during the first 12 hours post-ingestion, mainly as the acyl-conjugated form of the drug 5.
- Half-life
1.65 h 3
- Clearance
Mainly cleared via glucuronide conjugation and followed by renal excretion, mainly unchanged 3.
- 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
Nausea and/or vomiting, stomach pain, diarrhea, digestive problems (dyspepsia) are the most common symptoms of toxicity. More toxicity symptoms include dizziness, sleepiness, disturbed sleep, nervousness, headache, palpitations, flushing, stomach problems, constipation, dry mouth, flatulence, skin rash, tiredness, pain, feeling feverish and shivering, and malaise.
Severe toxicity can lead to thrombocytopenia and anemia with bleeding episodes. Dexketoprofen is associated with a small increased risk of myocardial infarction 6.
- Pathways
- Not Available
- 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 Dexketoprofen 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 Dexketoprofen is combined with Abciximab. Acebutolol Dexketoprofen may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Dexketoprofen. Acemetacin The risk or severity of adverse effects can be increased when Dexketoprofen is combined with Acemetacin. - Food Interactions
- Not Available
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 Dexketoprofen trometamol N674F7L21E 156604-79-4 QUZMDHVOUNDEKW-MERQFXBCSA-N - International/Other Brands
- ACTIDEX / DESKETO / DEXADOL / DEXAK / DEXALGIN / DEXAROM / DEXOFEN / DEXOKET / DEXOMEN / DEXPRO / DEXTANOL / DEXTRAFAST / DKTROM / ELEKTRA / ENANGEL / ENANTYUM / FEN LI / INFEN / KERAL / KETRON D / KITESSE / KITEX / QUIRALAM / QUIRGEL / ROTALFEN / ROTALGIN / STADIUM / SYMPAL / TOFEDEX / VIAXAL / YOUBAIFEN
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ASEKET 25 MG/500 MG FILM TABLET,TABLET, 20 ADET Dexketoprofen (25 mg) + Acetaminophen (500 mg) Tablet, film coated Oral BERKO İLAÇ VE KİMYA SAN. A.Ş. 2015-02-19 Not applicable Turkey 
DEKSİT 12,5 MG/ML + 2,5 MG/ML DERİYE UYGULANACAK SPREY, ÇÖZELTİ 50 ML Dexketoprofen trometamol (1.25 %) + Thiocolchicoside (0.25 %) Spray Topical DROGSAN İLAÇLARI SAN. VE TİC. A.Ş. 2020-08-14 2021-10-04 Turkey DEKSİT 25 MG/4 MG TABLET Dexketoprofen (25 mg) + Thiocolchicoside (4 mg) Tablet DROGSAN İLAÇLARI SAN. VE TİC. A.Ş. 2017-12-21 Not applicable Turkey DEKSİT 25 MG/8 MG TABLET Dexketoprofen (25 mg) + Thiocolchicoside (8 mg) Tablet DROGSAN İLAÇLARI SAN. VE TİC. A.Ş. 2017-12-21 Not applicable Turkey DETROİTS 25 MG/4 MG FİLM KAPLI TABLET, 15 TABLET Dexketoprofen trometamol (25 mg) + Thiocolchicoside (4 mg) Tablet, coated Oral NEUTEC İLAÇ SAN. TİC. A.Ş. 2014-09-26 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image DEXOFEN 25 MG FILM TABLET, 20 ADET Dexketoprofen (25 mg) Tablet, film coated Oral ATABAY KİMYA SAN. VE TİC. A.Ş. 2013-01-29 Not applicable Turkey DEXPRO 25 MG FILM TABLET, 20 ADET Dexketoprofen (25 mg) Tablet, film coated Oral AKAR FARMA MEDİKAL İLAÇ KOZMETİK GIDA TARIM SAN. VE TİC. İTH. İHR. LTD. ŞTİ. 2013-01-29 Not applicable Turkey
Categories
- ATC Codes
- M02AA27 — Dexketoprofen
- 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
- N02AJ — Opioids in combination with non-opioid analgesics
- N02A — OPIOIDS
- N02 — ANALGESICS
- N — NERVOUS SYSTEM
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Alcohols
- 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
- Drugs that are Mainly Renally Excreted
- Glycols
- Musculo-Skeletal System
- Nephrotoxic agents
- Nervous System
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Phenylpropionates
- Propionates
- Propylene Glycols
- Sensory System Agents
- Topical Products for Joint and Muscular Pain
- 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, monocarboxylic acid (CHEBI:76128)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6KD9E78X68
- CAS number
- 22161-81-5
- InChI Key
- DKYWVDODHFEZIM-NSHDSACASA-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)/t11-/m0/s1
- IUPAC Name
- (2S)-2-(3-benzoylphenyl)propanoic acid
- SMILES
- [H][C@@](C)(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1
References
- General References
- Valles J, Artigas R, Crea A, Muller F, Paredes I, Zapata A, Capriati A: Clinical pharmacokinetics of parenteral dexketoprofen trometamol in healthy subjects. Methods Find Exp Clin Pharmacol. 2006 Jun;28 Suppl A:7-12. [Article]
- Dexketoprofen [Link]
- Concise info Dexketoprofen [Link]
- DEXKETOPROFEN [Link]
- PRECLINICAL AND CLINCIAL DEVELOPMENT OF DEXOKETOPROFEN [Link]
- Dexktoprofen drug insert [Link]
- Dexketoprofen information [Link]
- Analgesic properties of dexketoprofen trometamol [Link]
- External Links
- Human Metabolome Database
- HMDB0041873
- KEGG Drug
- D07269
- PubChem Compound
- 667550
- PubChem Substance
- 310265121
- ChemSpider
- 580922
- BindingDB
- 50088570
- 237162
- ChEBI
- 76128
- ChEMBL
- CHEMBL75435
- ZINC
- ZINC000000005560
- PharmGKB
- PA166049175
- PDBe Ligand
- 9KL
- Wikipedia
- Dexketoprofen
- PDB Entries
- 5zwr / 6ock / 6u4r / 7jwn
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 Prevention Acute Pain 1 4 Completed Prevention Injection Pain 1 4 Completed Supportive Care Third Molar Surgery 1 4 Completed Treatment Acute Migraine 1 4 Completed Treatment Acute Pain 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intramuscular; Intravenous Injection Intramuscular; Intravenous 50 mg/2ml Injection, solution Parenteral 50 mg/2ml Tablet, coated Oral 25 mg Tablet, orally disintegrating Oral 25 mg Spray Topical Tablet Solution Intravenous 50.000 mg Tablet, coated Oral Tablet, coated Oral 50 mg Tablet, effervescent Oral Tablet, effervescent Oral 50 mg Powder Oral 12.5 mg Powder Oral 25 mg Tablet, film coated Oral 75 mg Solution Oral Tablet, coated Oral 2500000 mg Tablet, effervescent Oral 12.5 mg Tablet, effervescent Oral 25 mg Tablet, effervescent Oral 25 mg/8mg Tablet, film coated Oral 36.9 MG Capsule, liquid filled Oral 25 mg Tablet Oral 36.900 mg Gel Topical 12.5 mg/g Tablet, film coated Oral 50 mg Granule, for solution Oral 12.5 MG Injection, solution 50 MG/2ML Tablet Oral 12.5 MG Tablet Oral 25 MG Injection, solution Tablet Oral Injection, solution Intramuscular; Intravenous 73.8 mg/2ml Injection, powder, lyophilized, for solution Intravenous 500 IU Solution 36.90 mg Solution Parenteral 73.800 mg Injection Intramuscular; Intravenous Gel Topical 1.85 % Tablet, film coated Oral 73.8 mg Granule 25 MG Granule, for solution Oral 25 MG Solution Oral 25 MG Tablet, film coated Oral 12.5 MG Tablet, film coated Oral 20 MG Tablet, film coated Oral Granule, for solution Oral Solution Intramuscular; Intravenous 73.8 mg/2ml Solution Intramuscular; Intravenous Granule, for solution Oral 25.00 mg Solution Intramuscular; Intravenous 50 mg Solution Intramuscular; Intravenous 5000000 mg Granule, for solution Oral Tablet, film coated Oral Gel Topical 1.25 % Gel Topical Tablet, extended release Oral 75 mg Tablet, effervescent Oral Tablet Oral Tablet, coated Oral Tablet, film coated Oral 25 mg Solution Parenteral 50.00 mg Tablet Oral 12.500 mg Powder Oral Gel Topical 12.5 mg/1g Injection, solution Intramuscular; Intravenous 50 mg/2ml Solution Intramuscular; Intravenous 50 mg/2ml Injection Intramuscular; Intravenous 25 MG/ML Tablet, coated Oral 12.5 mg Solution Intravenous 73.820 mg Solution Oral 36.900 mg Capsule Oral 0.50 mg Tablet, film coated Oral 25 mg Granule, for solution Oral 25 mg/1sachet Solution 50 mg/2ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 75 [L1300] boiling point (°C) 431.32 [L1300] - 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 26.88 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.8306043 predictedDarkChem Lite v0.1.0 [M-H]- 158.88155 predictedDeepCCS 1.0 (2019) [M+H]+ 175.2270043 predictedDarkChem Lite v0.1.0 [M+H]+ 161.23955 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.1489043 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.06346 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
- Analgesic properties of dexketoprofen trometamol [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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
- Analgesic properties of dexketoprofen trometamol [Link]
Enzymes
- 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
- 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. 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
Drug created at October 21, 2015 15:57 / Updated at February 03, 2022 21:01