Oxicam

Oxicam is a class of nonsteroidal anti-inflammatory drugs (NSAIDs) that 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.[2]

Piroxicam

Examples include:

Chemistry

The physico-chemical characteristics of these molecules vary greatly depending upon the environment.[3]

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:[4]

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
  1. Olkkola KT, Brunetto AV, Mattila MJ (1994). "Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents". Clinical Pharmacokinetics. 26 (2): 107–20. doi:10.2165/00003088-199426020-00004. PMID 8162655.
  2. Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 233. ISBN 3-8047-1763-2.
  3. Banerjee R, Chakraborty H, Sarkar M (2003). "Photophysical studies of oxicam group of NSAIDs: piroxicam, meloxicam and tenoxicam". Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy. 59 (6): 1213–22. doi:10.1016/S1386-1425(02)00300-1. PMID 12659890.
  4. Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L (2015). "Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study". RSC Advances. 5: 31852–31860. doi:10.1039/c5ra03653d.


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