Antiinflammatory drugs, nonsteroidal selection

M. Hudson, E. Rahme, H. Richard and L. Pilote, Risk of congestive heart failure with nonsteroidal antiinflammatory drugs and selective cyclooxygenase 2 inhibitors a class effect , Arthritis Rheum., 2007, 57, 516-523. 

The outstanding influence of the anionic component on the activity and selectivity of enzymes was demonstrated in the Candida rugosa lipase-catalyzed kinetic resolution of ibuprofen, a nonsteroidal antiinflammatory drug with sales of USD 183 million in 2006 (Scheme 5.15) [63]. 

Mobic is the proprietary preparation of meloxicam, a non-steroidal antiinflammatory drug, which is also a selective inhibitor of cyclo-oxygenase-2. It is therefore less likely to cause gastrointestinal side-effects than other nonsteroidal anti-inflammatory drugs. However, it is still best to administer meloxicam after food. 

Kalgutkar, A. S., Crews, B. C., Rowlinson, S. W., Marnett, A. B., Kozak, K. R., Remmel, R. P., Marnett, L. J. Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors, Proc. Natl. Acad. Sci. USA 2000, 97, 925-930. 

Willkens RF. The selection of a nonsteroidal antiinflammatory drug is there a difference ] Rheumatol. 1992 19(suppl 36) 9-12. 

This conversion of a 1,2-diol to an epoxide has been used as an approach to 2-arylpropanoic acids, members of the nonsteroidal antiinflammatory drugs (NSAIDS) family of drugs.163 However, the sequence can be shortened by a selective hydrogenolysis, as illustrated for naproxen (20) (Scheme 9.24).164... 

Giachetti et al. [60] compared the performance of mass selective detector (MSD), electron capture detector (ECD) and nitrogen-phosphorus detector (NPD) of gas chromatography systems in the assay of six nonsteroidal antiinflammatory drugs in the plasma samples. As a practical test, six NSAIDs (mefenamic, flufenamic, meclofenamic and niflumic acids, diclofenac and clonixin) added to plasma samples were detected and quantified. The analyses were carried out after solvent extraction from an acidic medium and subsequent methylation. The linearity of response was tested for all the detection systems in the range of 1-25 ng/mL. Precision and accuracy were detected at 1, 5 and 10 ng/mL. The minimum quantifiable level for the six drugs was about 1 ng/mL with each of the three detection systems. 

Pugsley TA, Spencer C, Boctor AM, Gluckman MI (1985) Selective inhibition of the cyclooxygenase pathway of the arachidonic acid cascade by the nonsteroidal antiinflammatory drug isoxicam. Drug Dev Res 5 171-178... 

Naproxen and ibuprofen are nonsteroidal antiinflammatory drugs (NSAIDs) widely available as and OTC medications. In both cases the active (S)-enantiomer is far more potent. Selective hydrolysis of racemic esters of these drugs enables the production of both (S)-naproxen and (S)-ibuprofen. A number of... 

Mitchell JA, Akarasereenont P, Thiemermann C, Flower RJ, Vane JR. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci USA 1993 90(24) 11693-7. 

Schneider V, Levesque LE, Zhang B, Hutchinson T, and Brophy JM. 2006. Association of selective and conventional nonsteroidal antiinflammatory drugs with acute renal failure A population-based, nested case-control analysis. Am J Epidemiol 164 881-889. 

Gislason GH, Jacobsen S, Rasmussen JN et al. Risk of death or reinfarction associated with the use of selective cyclooxygenase-2 inhibitors and nonselective nonsteroidal antiinflammatory drugs after acute myocardial infarction. Circulation 2006 13 2906-2913... 

The coxibs, including celecoxib (Celebrex), are a recently developed class of nonsteroidal antiinflammatory drugs (NSAIDs). The coxibs show antiinflammatory actions without affecting platelet function. These effects of the coxibs are best attributed to selective inhibition of which of the following ... 

Herzfeldt CD and Kiimmel R, Dissociation constants, solubilities, and dissolution rates of some selected nonsteroidal antiinflammatories. Drug Dev. Ind. Pharm., 9(5), 767-793 (1983). NB See Ibuprofen for furdier details. 

---