Dexketoprofen

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
UProstaglandin G/H synthase 1
antagonist
Humans
UProstaglandin G/H synthase 2
antagonist
Humans
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 [L1204]

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
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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
Not Available

Interactions

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.
DrugInteraction
AbacavirDexketoprofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Dexketoprofen is combined with Abciximab.
AcebutololDexketoprofen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Dexketoprofen.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Dexketoprofen.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Dexketoprofen is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Acetazolamide.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Dexketoprofen.
Acetyl sulfisoxazoleThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe risk or severity of bleeding and gastrointestinal bleeding can be increased when Acetylsalicylic acid is combined with Dexketoprofen.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dexketoprofen trometamolN674F7L21E156604-79-4QUZMDHVOUNDEKW-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
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ASEKET 25 MG/500 MG FILM TABLET,TABLET, 20 ADETDexketoprofen (25 mg) + Acetaminophen (500 mg)Tablet, film coatedOralBERKO İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
DEKSİT 12,5 MG/ML + 2,5 MG/ML DERİYE UYGULANACAK SPREY, ÇÖZELTİ 50 MLDexketoprofen trometamol (1.25 %) + Thiocolchicoside (0.25 %)SprayTopicalDROGSAN İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
DEKSİT 25 MG/4 MG TABLETDexketoprofen (25 mg) + Thiocolchicoside (4 mg)TabletDROGSAN İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
DEKSİT 25 MG/8 MG TABLETDexketoprofen (25 mg) + Thiocolchicoside (8 mg)TabletDROGSAN İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
DETROİTS 25 MG/4 MG FİLM KAPLI TABLET, 15 TABLETDexketoprofen trometamol (25 mg) + Thiocolchicoside (4 mg)Tablet, coatedOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
DETROİTS 25 MG/4 MG FİLM KAPLI TABLET, 20 TABLETDexketoprofen trometamol (25 mg) + Thiocolchicoside (4 mg)Tablet, coatedOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
DETROİTS 25 MG/8 MG FİLM KAPLI TABLET, 14 TABLETDexketoprofen trometamol (25 mg) + Thiocolchicoside (8 mg)Tablet, coatedOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
DEXAPHEN 25 MG/500 MG FİLM KAPLI TABLET, 20 ADETDexketoprofen trometamol (25 mg) + Acetaminophen (500 mg)Tablet, coatedOralBERAT BERAN İLAÇ SAN. VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
DEXCORIL 25/4 MG EFERVESAN TABLET ,15 EFERVESAN TABLETDexketoprofen trometamol (25 mg) + Thiocolchicoside (4 mg)Tablet, effervescentOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
DEXCORIL 25/4 MG EFERVESAN TABLET ,EFERVESAN TABLET, 20 ADETDexketoprofen trometamol (25 mg) + Thiocolchicoside (4 mg)Tablet, effervescentOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DEXOFEN 25 MG FILM TABLET, 20 ADETDexketoprofen (25 mg)Tablet, film coatedOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
DEXPRO 25 MG FILM TABLET, 20 ADETDexketoprofen (25 mg)Tablet, film coatedOralAKAR FARMA MEDİKAL İLAÇ KOZMETİK GIDA TARIM SAN. VE TİC. İTH. İHR. LTD. ŞTİ.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
M02AA27 — DexketoprofenN02AJ14 — Tramadol and dexketoprofenM01AE17 — Dexketoprofen
Drug Categories
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
  1. 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]
  2. Dexketoprofen [Link]
  3. Concise info Dexketoprofen [Link]
  4. DEXKETOPROFEN [Link]
  5. PRECLINICAL AND CLINCIAL DEVELOPMENT OF DEXOKETOPROFEN [Link]
  6. Dexktoprofen drug insert [Link]
  7. Dexketoprofen information [Link]
  8. Analgesic properties of dexketoprofen trometamol [Link]
Human Metabolome Database
HMDB0041873
KEGG Drug
D07269
PubChem Compound
667550
PubChem Substance
310265121
ChemSpider
580922
BindingDB
50088570
RxNav
237162
ChEBI
76128
ChEMBL
CHEMBL75435
ZINC
ZINC000000005560
PharmGKB
PA166049175
PDBe Ligand
9KL
Wikipedia
Dexketoprofen
PDB Entries
5zwr / 6ock / 6u4r / 7jwn

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentMigraine1
4CompletedPreventionInjection Pain1
4CompletedPreventionPain, Acute1
4CompletedSupportive CareThird Molar Surgery1
4CompletedTreatmentAcute Migraine1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentIrreversible Pulpitis1
4CompletedTreatmentLow Back Pain, Mechanical1
4CompletedTreatmentMigraine1
4CompletedTreatmentMusculoskeletal Pain2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous
Injection, solutionParenteral
Tablet, coatedOral
Tablet, coatedOral25 mg
Tablet, orally disintegratingOral
SprayTopical
Tablet
Tablet, coatedOral
Tablet, effervescentOral
Tablet, effervescentOral
PowderOral
SolutionOral25 mg
Tablet, effervescentOral25 mg/8mg
Capsule, liquid filledOral25 mg
GelTopical
TabletOral
Injection, solution
Injection, powder, lyophilized, for solutionIntravenous500 IU
InjectionIntramuscular; Intravenous
Tablet, film coatedOral
Granule, for solutionOral
SolutionOral
SolutionIntramuscular; Intravenous
SolutionIntramuscular; Intravenous50 mg
Tablet, extended releaseOral
Tablet, film coatedOral
Granule, for solutionOral
PowderOral
GelTopical
InjectionIntramuscular; Intravenous25 MG/ML
Tablet, film coatedOral25 mg
Granule, for solutionOral25 mg/1sachet
Solution50 mg/2ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75[L1300]
boiling point (°C)431.32[L1300]
Predicted Properties
PropertyValueSource
Water Solubility0.0213 mg/mLALOGPS
logP3.29ALOGPS
logP3.61ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.52 m3·mol-1ChemAxon
Polarizability26.88 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-3910000000-1bfe148d4ab6af381e80

Targets

Drugtargets
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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
  1. 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
  1. 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 on October 21, 2015 15:57 / Updated on May 05, 2021 20:31