Piroxicam, the most popular drug of the oxicam class.[1]
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]

Piroxicam tautomers.svg

Side effects

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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

  1. ^ 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.
  2. ^ 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. England, UK: Royal Society of Chemistry. 5 (40): 31852–31860. doi:10.1039/c5ra03653d.
  3. ^ 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.
  4. ^ 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. Elsevier. 59 (6): 1213–22. Bibcode:2003AcSpA..59.1213B. doi:10.1016/S1386-1425(02)00300-1. PMID 12659890.