Identification

Name
Dexketoprofen
Accession Number
DB09214
Type
Small Molecule
Groups
Approved, Investigational
Description

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].

Structure
Thumb
Synonyms
  • Dexketoprofeno
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
Categories
UNII
6KD9E78X68
CAS number
22161-81-5
Weight
Average: 254.2806
Monoisotopic: 254.094294314
Chemical Formula
C16H14O3
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

Pharmacology

Indication

For short-term treatment of mild to moderate pain, including dysmenorrhoea, musculoskeletal pain and toothache [6].

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
Human
UProstaglandin G/H synthase 2
antagonist
Human
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].

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].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Dexketoprofen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Dexketoprofen is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Dexketoprofen is combined with 4-hydroxycoumarin.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
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.
AcarboseDexketoprofen may decrease the excretion rate of Acarbose which could result in a higher serum level.
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.
Food Interactions
Not Available

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. [PubMed:16801987]
  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]
External Links
Human Metabolome Database
HMDB0041873
KEGG Drug
D07269
PubChem Compound
667550
PubChem Substance
310265121
ChemSpider
580922
BindingDB
50088570
ChEBI
76128
ChEMBL
CHEMBL75435
PharmGKB
PA166049175
Wikipedia
Dexketoprofen
ATC Codes
M02AA27 — DexketoprofenM01AE17 — Dexketoprofen

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailablePain, Acute1
3Active Not RecruitingTreatmentPostoperative pain1
3CompletedTreatmentPain, Acute2
4CompletedPreventionInjection Pain1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentMigraine, Acute1
4CompletedTreatmentMigraines1
4CompletedTreatmentPostoperative pain2
4CompletedTreatmentPainful musculoskeletal conditions2
4Not Yet RecruitingTreatmentSupratentorial Neoplasms1
4RecruitingTreatmentNo Reconstructive Breast Surgery1
4Unknown StatusTreatmentDysmenorrhea1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

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, monocarboxylic acid (CHEBI:76128)

Targets

Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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 09:57 / Updated on November 05, 2018 17:49