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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:45:11 UTC
Update Date2021-09-14 15:20:37 UTC
HMDB IDHMDB0041873
Secondary Accession Numbers
  • HMDB41873
Metabolite Identification
Common NameDexketoprofen
DescriptionDexketoprofen belongs to a class of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the action of a substance in the body called cyclo-oxygenase. Cyclo-oxygenase 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 is a non-steroidal anti-inflammatory drug. It is manufactured by Menarini, under the tradename Keral. It is available in the UK, as dexketoprofen trometamol, as a prescription-only drug and in Latin America as Miracox, produced by Stein in Costa Rica. In Italy it is available as an over the counter-drug under the tradename Enantyum. In Lithuania it is available as over the counter-drug uder tradename Dolmen.
Structure
Data?1563863710
Synonyms
ValueSource
(+)-(S)-m-Benzoylhydratropic acidChEBI
(+)-3-Benzoylhydratropic acidChEBI
(+)-KetoprofenChEBI
(S)-3-Benzoyl-alpha-methylbenzeneacetic acidChEBI
(S)-KetoprofenChEBI
(+)-(S)-m-BenzoylhydratropateGenerator
(+)-3-BenzoylhydratropateGenerator
(S)-3-Benzoyl-a-methylbenzeneacetateGenerator
(S)-3-Benzoyl-a-methylbenzeneacetic acidGenerator
(S)-3-Benzoyl-alpha-methylbenzeneacetateGenerator
(S)-3-Benzoyl-α-methylbenzeneacetateGenerator
(S)-3-Benzoyl-α-methylbenzeneacetic acidGenerator
BadyketMeSH
QuiralamMeSH
KeralMeSH
SympalMeSH
KetesseMeSH
EnangelMeSH
EnantyumMeSH
AdolquirMeSH
QuirgelMeSH
Dexketoprofen trometamolMeSH
Chemical FormulaC16H14O3
Average Molecular Weight254.2806
Monoisotopic Molecular Weight254.094294314
IUPAC Name(2S)-2-(3-benzoylphenyl)propanoic acid
Traditional Name(+)-ketoprofen
CAS Registry Number22161-81-5
SMILES
[H][C@@](C)(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1
InChI Identifier
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
InChI KeyDKYWVDODHFEZIM-NSHDSACASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Aryl-phenylketone
  • Diphenylmethane
  • 2-phenylpropanoic-acid
  • Benzoyl
  • Aryl ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.52 m³·mol⁻¹ChemAxon
Polarizability26.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1940000000-f7bd8f8c00db90255ec42017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9852000000-3751805b2d0db496fd232017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-1950000000-ac8717c49fa2236f95d52021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-3910000000-1bfe148d4ab6af381e802017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3910000000-1bfe148d4ab6af381e802017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-4768d924931af7c455442017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0960000000-15decdbeb8a53d876f132017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-1900000000-d495168bad218af121c32017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-308307494d5069767ed62017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0290000000-2f3d07212d1e75aaeec32017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kcr-5920000000-b52dbdf1eacfc9bd9a6a2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-01427ffe174426164dca2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0980000000-6adc02672decadc11a7f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-057i-4900000000-246c2457778cde32361d2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09214
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID154933
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDexketoprofen
METLIN IDNot Available
PubChem Compound177976
PDB IDNot Available
ChEBI ID76128
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Miranda HF, Romero MA, Puig MM: Antinociceptive and anti-exudative synergism between dexketoprofen and tramadol in a model of inflammatory pain in mice. Fundam Clin Pharmacol. 2012 Jun;26(3):373-82. doi: 10.1111/j.1472-8206.2010.00922.x. Epub 2011 Jan 25. [PubMed:22081874 ]
  2. Vera P, Zapata L, Gich I, Mancebo J, Betbese AJ: [Hemodynamic and antipyretic effects of paracetamol, metamizol and dexketoprofen in critical patients]. Med Intensiva. 2012 Dec;36(9):619-25. doi: 10.1016/j.medin.2012.02.003. Epub 2012 Mar 16. [PubMed:22425338 ]
  3. Porwal A, Mahajan AD, Oswal DS, Erram SS, Sheth DN, Balamurugan S, Kamat V, Enadle RP, Badadare A, Bhatnagar SK, Walvekar RS, Dhorepatil S, Naik RC, Basu I, Kshirsagar SN, Keny JV, Sengupta S: Efficacy and tolerability of fixed-dose combination of dexketoprofen and dicyclomine injection in acute renal colic. Pain Res Treat. 2012;2012:295926. doi: 10.1155/2012/295926. Epub 2012 Apr 23. [PubMed:22577544 ]
  4. Ozer AB, Erhan OL, Keles E, Demirel I, Bestas A, Gunduz G: Comparison of the effects of preoperative and intraoperative intravenous application of dexketoprofen on postoperative analgesia in septorhinoplasty patients: randomised double blind clinical trial. Eur Rev Med Pharmacol Sci. 2012 Nov;16(13):1828-33. [PubMed:23208967 ]
  5. Tunali Y, Akcil EF, Dilmen OK, Tutuncu AC, Koksal GM, Akbas S, Vehid H, Yentur E: Efficacy of intravenous paracetamol and dexketoprofen on postoperative pain and morphine consumption after a lumbar disk surgery. J Neurosurg Anesthesiol. 2013 Apr;25(2):143-7. doi: 10.1097/ANA.0b013e31827464af. [PubMed:23360885 ]
  6. Eken C, Serinken M, Elicabuk H, Uyanik E, Erdal M: Intravenous paracetamol versus dexketoprofen versus morphine in acute mechanical low back pain in the emergency department: a randomised double-blind controlled trial. Emerg Med J. 2014 Mar;31(3):177-81. doi: 10.1136/emermed-2012-201670. Epub 2013 Feb 13. [PubMed:23407378 ]
  7. Salman AE, Yetisir F, Yurekli B, Aksoy M, Yildirim M, Kilic M: The efficacy of the semi-blind approach of transversus abdominis plane block on postoperative analgesia in patients undergoing inguinal hernia repair: a prospective randomized double-blind study. Local Reg Anesth. 2013 Jan 18;6:1-7. doi: 10.2147/LRA.S38359. Print 2013. [PubMed:23630432 ]
  8. Allais G, Rolando S, Schiapparelli P, Airola G, Borgogno P, Mana O, Benedetto C: Frovatriptan plus dexketoprofen in the treatment of menstrually related migraine: an open study. Neurol Sci. 2013 May;34 Suppl 1:S179-81. doi: 10.1007/s10072-013-1390-0. [PubMed:23695075 ]