Drug class
Piroxicam , the most popular drug of the oxicam class.[ 1]
Oxicam is a class of non-steroidal anti-inflammatory drugs (NSAIDs),[ 2] meaning that they have anti-inflammatory , analgesic , and antipyretic therapeutic effects. Oxicams bind closely to plasma proteins .[ 1] Most oxicams are unselective inhibitors of the cyclooxygenase (COX) enzymes. The exception is meloxicam with a slight (10:1) preference for COX-2 , which, however, is only clinically relevant at low doses.[ 3]
The most popular drug of the oxicam class is piroxicam .[ 1] Other examples include: ampiroxicam , droxicam , pivoxicam , tenoxicam , lornoxicam ,[ 1] and meloxicam .
Isoxicam has been suspended as a result of fatal skin reactions.[ 1]
Chemistry
The physico-chemical characteristics of these molecules vary greatly depending upon the environment.[ 4]
In contrast to most other NSAIDs, oxicams are not carboxylic acids . They are tautomeric , and can exist as a number of tautomers (keto-enol tautomerism ), here exemplified by piroxicam:[ 2]
Side effects
The oxicams are associated with drug-related erythema multiforme (EM), Stevens–Johnson syndrome , and toxic epidermal necrolysis (TEN). This association is one of the reasons oxicams are not regularly prescribed.
References
^ 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