Drug class
Piroxicam , the most popular drug of the oxicam class.[ 1] Oxicam is a class ofnon-steroidal anti-inflammatory drugs (NSAIDs),[ 2] meaning that they haveanti-inflammatory ,analgesic , and antipyretic therapeutic effects. Oxicams bind closely toplasma proteins .[ 1] Most oxicams are unselective inhibitors of thecyclooxygenase (COX) enzymes. The exception ismeloxicam with a slight (10:1) preference forCOX-2 , which, however, is only clinically relevant at low doses.[ 3]
The most popular drug of the oxicam class ispiroxicam .[ 1] Other examples include:ampiroxicam ,droxicam ,pivoxicam ,tenoxicam ,lornoxicam ,[ 1] andmeloxicam .
Isoxicam has been suspended as a result of fatal skin reactions.[ 1]
The physico-chemical characteristics of these molecules vary greatly depending upon the environment.[ 4]
In contrast to most other NSAIDs, oxicams are notcarboxylic acids . They aretautomeric , and can exist as a number of tautomers (keto-enol tautomerism ), here exemplified by piroxicam:[ 2]
The oxicams are associated with drug-relatederythema multiforme (EM),Stevens–Johnson syndrome , andtoxic epidermal necrolysis (TEN). This association is one of the reasons oxicams are not regularly prescribed.
^a b c d e Olkkola KT, Brunetto AV, Mattila MJ (February 1994). "Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents".Clinical Pharmacokinetics .26 (2):107– 20.doi :10.2165/00003088-199426020-00004 .PMID 8162655 .S2CID 13300943 . ^a b Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L (March 2015)."Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study" .RSC Advances .5 (40). England, UK:Royal Society of Chemistry :31852– 31860.Bibcode :2015RSCAd...531852I .doi :10.1039/c5ra03653d . ^ Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001).Mutschler Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie; mit einführenden Kapiteln in die Anatomie, Physiologie und Pathophysiologie [Mutster medicine effects: Textbook of pharmacology and toxicology; with introductory chapters in anatomy, physiology and pathophysiology ] (in German) (8 ed.).Stuttgart , Germany:Wissenschaftliche Verlagsgesellschaft . p. 233.ISBN 3-8047-1763-2 .OCLC 48723029 .OL 12928661M . ^ Banerjee R, Chakraborty H, Sarkar M (April 2003). "Photophysical studies of oxicam group of NSAIDs: piroxicam, meloxicam and tenoxicam".Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy .59 (6).Elsevier :1213– 22.Bibcode :2003AcSpA..59.1213B .doi :10.1016/S1386-1425(02)00300-1 .PMID 12659890 .
Receptor (ligands )
DP (D2 ) Tooltip Prostaglandin D2 receptor
DP1 Tooltip Prostaglandin D2 receptor 1 DP2 Tooltip Prostaglandin D2 receptor 2
EP (E2 ) Tooltip Prostaglandin E2 receptor
EP1 Tooltip Prostaglandin EP1 receptor EP2 Tooltip Prostaglandin EP2 receptor EP3 Tooltip Prostaglandin EP3 receptor EP4 Tooltip Prostaglandin EP4 receptor Unsorted
FP (F2α ) Tooltip Prostaglandin F receptor IP (I2 ) Tooltip Prostacyclin receptor TP (TXA2 ) Tooltip Thromboxane receptor Unsorted
Enzyme (inhibitors )
COX ( PTGS) PGD2 S Tooltip Prostaglandin D synthase PGES Tooltip Prostaglandin E synthase PGFS Tooltip Prostaglandin F synthase PGI2 S Tooltip Prostacyclin synthase TXAS Tooltip Thromboxane A synthase
Others