(S)-Ketoprofen - CAS 22161-81-5
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
(S)-Ketoprofen
Catalog Number:
22161-81-5
Synonyms:
(S)-2-(3-benzoylphenyl)Propionic Acid Dexketoprofen; (S)-3-benzoyl-α-methyl-benzeneacetic acid
CAS Number:
22161-81-5
Description:
A potent inhibitor of COX-1 and COX-2
Molecular Weight:
254.3
Molecular Formula:
C16H14O3
Quantity:
Grams-Kilos
Quality Standard:
In-house
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
O=C(C1=CC=CC([C@H](C)C(O)=O)=C1)C2=CC=CC=C2
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
InChIKey:
DKYWVDODHFEZIM-NSHDSACASA-N
Targets:
Cox-2
Chemical Structure
CAS 22161-81-5 (S)-Ketoprofen

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Reference Reading


1.Analgesic Effect of the Newly Developed S(+)-Flurbiprofen Plaster on Inflammatory Pain in a Rat Adjuvant-Induced Arthritis Model.
Sugimoto M1, Toda Y1, Hori M1, Mitani A1, Ichihara T1, Sekine S1, Hirose T2, Endo H1, Futaki N3, Kaku S1, Otsuka N2, Matsumoto H4. Drug Dev Res. 2016 Feb;77(1):20-8. doi: 10.1002/ddr.21288. Epub 2016 Jan 13.
Preclinical Research This article describes the properties of a novel topical NSAID (Nonsteroidal anti-inflammatory drug) patch, SFPP (S(+)-flurbiprofen plaster), containing the potent cyclooxygenase (COX) inhibitor, S(+)-flurbiprofen (SFP). The present studies were conducted to confirm human COX inhibition and absorption of SFP and to evaluate the analgesic efficacy of SFPP in a rat adjuvant-induced arthritis (AIA) model. COX inhibition by SFP, ketoprofen and loxoprofen was evaluated using human recombinant COX proteins. Absorption of SFPP, ketoprofen and loxoprofen from patches through rat skin was assessed 24 h after application. The AIA model was induced by injecting Mycobacterium tuberculosis followed 20 days later by the evaluation of the prostaglandin PGE2 content of the inflamed paw and the pain threshold. SFP exhibited more potent inhibitory activity against COX-1 (IC50  = 8.97 nM) and COX-2 (IC50  = 2.94 nM) than the other NSAIDs evaluated.
2.Pharmacological Characterization of the Edema Caused by Vitalius dubius (Theraphosidae, Mygalomorphae) Spider Venom in Rats.
Rocha-E-Silva TA1, Linardi A2, Antunes E2, Hyslop S2. J Pharmacol Exp Ther. 2016 Jan;356(1):13-9. doi: 10.1124/jpet.115.226787. Epub 2015 Oct 15.
Bites by tarantulas (Theraphosidae, Mygalomorphae) in humans can result in mild clinical manifestations such as local pain, erythema, and edema. Vitalius dubius is a medium-sized, nonaggressive theraphosid found in southeastern Brazil. In this work, we investigated the mediators involved in the plasma extravasation caused by V. dubius venom in rats. The venom caused dose-dependent (0.1-100 μg/site) edema in rat dorsal skin. This edema was significantly inhibited by ((S)1-{2-[3(3-4-dichlorophenyl)-1-(3-iso-propoxyphenylacetyl)piperidine-3-yl]ethyl}-4-phenyl-1-azoniabicyclo[2.2.2]octone, chloride) (SR140333, a neurokinin NK1 receptor antagonist), indomethacin [a nonselective cyclooxygenase (COX) inhibitor], cyproheptadine (a serotonin 5-hydroxytryptamine1/2 and histamine H1 receptor antagonist), and N(ω)-nitro-L-arginine methyl ester (a nitric oxide synthase inhibitor). In contrast, mepyramine (a histamine H1 receptor antagonist), D-Arg-[Hyp(3),Thi(5),D-Tic(7),Oic(8)-]-BK (JE 049, a bradykinin B2 receptor antagonist), and ((S)-N-methyl-N-[4-(4-acetylamino-4-phenylpiperidino)-2-(3,4-di-chlorophenyl)butyl]benzamide) (SR48968, a neurokinin NK2 receptor antagonist) had no effect on the venom-induced increase in vascular permeability.
3.Preparation and Pharmacological Evaluation of Novel Orally Active Ester Prodrugs of Ketoprofen with Non-Ulcerogenic Property.
Dhakane VD1, Thakare VN2, Dongare SB1, Bhale PS1, Mule YB1, Bandgar BP1, Bandgar HV3. Chem Biol Drug Des. 2015 Dec 30. doi: 10.1111/cbdd.12719. [Epub ahead of print]
The present study investigates anti-inflammatory activity with improved pharmacokinetic and non-ulcerogenic properties of various novel synthesized prodrugs of Ketoprofen in experimental animals. Prodrugs 3a, 3f and 3k were found to possess significant anti-inflammatory activity with almost non-ulcerogenic potential than standard drug Ketoprofen (1) in both normal and inflammation induced rats. The experimental findings elicited higher AUC and plasma concentration at 1h and 2h indicating improved oral bioavailability as compared to parent drug Ketoprofen. These prodrugs are found to have no gastric ulceration with retained anti-inflammatory activity. Therefore, present experimental findings demonstrated significant improvement of various pharmacokinetic properties with non-ulcerogenic potential of ester prodrugs of Ketoprofen. This article is protected by copyright. All rights reserved.
4.Simultaneous high-throughput determination of interaction kinetics for drugs and cyclodextrins by high performance affinity chromatography with mass spectrometry detection.
Wang C1, Wang X2, Xu X1, Liu B3, Xu X3, Sun L4, Li H5, Zhang J6. Anal Chim Acta. 2016 Feb 25;909:75-83. doi: 10.1016/j.aca.2015.12.026. Epub 2016 Jan 4.
The individual determination of the apparent dissociation rate constant (kd,app) using high performance affinity chromatography (HPAC) is a tedious process requiring numerous separate tests and massive data fitting, unable to provide the apparent association rate constant (ka) and equilibrium binding constant (Ka). In this study, a HPAC with mass spectrometry detection (HPAC-MS/MS) was employed to determine the drug-cyclodextrin (CD) interaction kinetics with low sample loading quantity (<10 ng per injection for single compound) and high-throughput yield as twenty drugs determined in one injection. The kd,app measured by HPAC-MS/MS approach were 0.89 ± 0.07, 4.34 ± 0.01, 1.48 ± 0.01 and 7.77 ± 0.04 s(-1) for ketoprofen, trimethoprim, indapamide and acetaminophen, with kd,app for acetaminophen consistent with that from the HPAC method with UV detector in our previous studies. For twenty drugs with diverse structures and chemical properties, good correlationship was found between kd,app measured by single compound analysis method and high-throughput HPAC-MS/MS approach, with the correlation coefficient of 0.