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K2135

Sigma-Aldrich

(S)-(+)-Ketoprofen

Synonym(s):

(S)-(+)-3-Benzoyl-α-methylbenzeneacetic acid, (S)-2-(3-Benzoylphenyl)propionic acid

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About This Item

Linear Formula:
C6H5COC6H4CH(CH3)CO2H
CAS Number:
22161-81-5
Molecular Weight:
254.28
MDL number:
MFCD00673316
UNSPSC Code:
12352000
PubChem Substance ID:
24896218

mp

75-78 °C (lit.)

SMILES string

C[C@H](C(O)=O)c1cccc(c1)C(=O)c2ccccc2

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 key

DKYWVDODHFEZIM-NSHDSACASA-N

Gene Information

human ... IL8RA(3577) , PTGS1(5742) , PTGS2(5743)
mouse ... Ptgs2(19225)

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Biochem/physiol Actions

Non-steroidal anti-inflammatory agent; non-selective inhibitor of COX-1 and COX-2.

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Certificates of Analysis (COA)

Lot/Batch Number
068H4125

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A Carabaza et al.
Journal of clinical pharmacology, 36(6), 505-512 (1996-06-01)
The stereoselective inhibition of inducible cyclooxygenase (COX-2) by chiral nonsteroidal antiinflammatory drugs (NSAIDs)--ketoprofen, flurbiprofen, and ketorolac--has been investigated. The activity and inhibition of COX-2 was assessed in three different in vitro systems: guinea pig whole blood, lipopolysaccharide (LPS)-stimulated human monocytes
P Santicioli et al.
British journal of pharmacology, 114(6), 1149-1158 (1995-03-01)
1. The effects of the (S)- and (R)-enantiomers of the cyclo-oxygenase (COX) inhibitor, ketoprofen, have been investigated on the spontaneous activity of the guinea-pig isolated renal pelvis and on electrical field stimulation-(EFS) induced contractions of the guinea-pig ureter in comparison
S Meini et al.
The Journal of pharmacology and experimental therapeutics, 287(1), 137-143 (1998-10-09)
The contractile responses elicited by the selective kinin B1 and B2 receptor agonists [desArg9]-bradykinin ([desArg9]-BK) and [Hyp3, Tyr(Me)8]-bradykinin ([Hyp3, Tyr(Me)8]-BK) (1 nM-10 microM), respectively, were evaluated in control vs. inflamed (cyclophosphamide 150 mg kg-1 i.p., 48 h before the sacrifice)
Elvira Mennillo et al.
Environmental toxicology and chemistry, 37(1), 201-212 (2017-08-11)
The increased use of nonsteroidal anti-inflammatory drugs (NSAIDs) has resulted in their ubiquitous presence in the environment. The toxicological properties of these 2 widely prescribed NSAIDs, namely racemic ketoprofen and its enantiomer S(+)-ketoprofen (dexketoprofen), were evaluated, firstly, by acute and
Elvira Mennillo et al.
Environmental toxicology and pharmacology, 59, 199-207 (2018-04-08)
Pharmaceuticals such as racemate ketoprofen (RS-KP) and its enantiomer, dexketoprofen (S(+)-KP) are highly detectable non-steroidal anti-inflammatory drugs (NSAIDs) in the aquatic environment and therefore are designated as one of the most emerging groups of pollutants that can affect environmental and
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