Ketoprofen - CAS 22071-15-4
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Not Intended for Therapeutic Use. For research use only.
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Ketoprofen, (RS)2-(3-benzoylphenyl)-propionic acid (chemical formula C16H14O3) is one of the propionic acid class of nonsteroidal anti-inflammatory drugs (NSAID) with analgesic and antipyretic effects. It acts by inhibiting the body's production of prostaglandin.
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1.Ecotoxicological potential of non-steroidal anti-inflammatory drugs (NSAIDs) in marine organisms: Bioavailability, biomarkers and natural occurrence in Mytilus galloprovincialis.
Mezzelani M1, Gorbi S1, Da Ros Z1, Fattorini D1, d'Errico G1, Milan M2, Bargelloni L2, Regoli F3. Mar Environ Res. 2016 Mar 22. pii: S0141-1136(16)30030-7. doi: 10.1016/j.marenvres.2016.03.005. [Epub ahead of print]
Pharmaceuticals represent a major environmental concern since the knowledge on their occurrence, distribution and ecotoxicological potential is still limited particularly in coastal areas. In this study, bioaccumulation and cellular effects of various non steroidal anti-inflammatory drugs (NSAIDs) were investigated in mussels Mytilus galloprovincialis to reveal whether common molecules belonging to the same therapeutic class might cause different effects on non target organisms. Organisms exposed to environmental concentrations of acetaminophen (AMP), diclofenac (DIC), ibuprofen (IBU), ketoprofen (KET) and nimesulide (NIM) revealed a significant accumulation of DIC, IBU and NIM, while AMP and KET were always below detection limit. Nonetheless, for all tested NSAIDs, measurement of a large panel of ecotoxicological biomarkers highlighted impairment of immunological parameters, onset of genotoxicity and modulation of lipid metabolism, oxidative and neurotoxic effects.
2.Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives.
Pawełczyk A1, Olender D2, Sowa-Kasprzak K3, Zaprutko L4. Molecules. 2016 Apr 12;21(4). pii: E420. doi: 10.3390/molecules21040420.
The current study focuses on the synthesis of several hybrid individuals combining a natural oleanolic acid skeleton and synthetic nonsteroidal anti-inflammatory drug moieties (NSAIDs). It studied structural modifications of the oleanolic acid structure by use of the direct reactivity of hydroxyl or hydroxyimino groups at position C-3 of the triterpenoid skeleton with the carboxylic function of anti-inflammatory drugs leading to new perspective compounds with high potential pharmacological activities. Novel ester- and iminoester-type derivatives of oleanolic unit with the different NSAIDs, such as ibuprofen, aspirin, naproxen, and ketoprofen, were obtained and characterized. Moreover, preliminary research of compounds obtaining structure stability under acidic conditions was examined and the PASS method of prediction of activity spectra for substances was used to estimate the potential biological activity of these compounds.
3.Occurrence of pharmaceuticals and UV filters in swimming pools and spas.
Ekowati Y1, Buttiglieri G2, Ferrero G3, Valle-Sistac J4, Diaz-Cruz MS4, Barceló D2,4, Petrovic M2,5, Villagrasa M2, Kennedy MD1,6, Rodríguez-Roda I2,7. Environ Sci Pollut Res Int. 2016 Apr 11. [Epub ahead of print]
The occurrence of 32 pharmaceuticals and 14 UV filters in swimming pools and spas was studied. Fifty-one water samples were collected from 17 pools located in sport centres and hotels in Catalonia, Spain. The samples were analysed by liquid chromatography-tandem mass spectrometry. The pharmaceuticals atenolol, carbamazepine, hydrochlorothiazide, metronidazole, ofloxacin, sulfamethoxazole, acetaminophen, ibuprofen, ketoprofen and phenazone were measured in water samples at concentrations higher than their limit of quantification (LOQ). The highest concentration of any individual pharmaceutical was measured for the diuretic hydrochlorothiazide (904 ng/L). The most frequently detected pharmaceutical was carbamazepine, as it was observed in more than half of all the water samples measured (53 %, 27/51). The UV filters at concentrations higher than LOQ in water samples were BP1, BP2, BP3, BP8, THB, 4DHB, 4MBC, OD-PABA, 1HBT, MeBT and DMeBT. The highest concentration of UV filter observed was 4MBC (69.
4.The effect of hydrogen bonding propensity and enantiomeric composition on the dynamics of supercooled ketoprofen - dielectric, rheological and NMR studies.
Adrjanowicz K1, Kaminski K, Tarnacka M, Szutkowski K, Popenda L, Bartkowiak G, Paluch M. Phys Chem Chem Phys. 2016 Apr 21;18(15):10585-93. doi: 10.1039/c6cp00578k. Epub 2016 Apr 1.
The aim of this work is to analyze in detail the effect of small hydrogen bonding (HB) structures and enantiomeric composition on the dynamics of glass-forming liquid ketoprofen. For that purpose dielectric relaxation, rheological and NMR studies were performed. Investigated samples are racemic ketoprofen, a single enantiomer of ketoprofen and a racemic ketoprofen methyl ester with no tendency to form HB dimers. The combination of complementary experimental techniques enables us to show that macroscopic viscosity η and α-relaxation time τα have nearly the same temperature dependencies, whereas the relation between the viscosity (or molecular reorientation) and the translational self-diffusion coefficient violates Stokes-Einstein law already at high temperature. Additionally, based on dielectric relaxation studies performed on increased pressure we were able to identify similarities and key differences in the supercooled liquid dynamics of investigated materials affected by their tendency to form intermolecular hydrogen bonds.
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