Oxicam is a class of non-steroidal anti-inflammatory drugs (NSAIDs), meaning that they have anti-inflammatory, analgesic, and antipyretic therapeutic effects. Oxicams bind closely to plasma proteins. 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.
The most popular drug of the oxicam class is piroxicam. Other examples include: ampiroxicam, droxicam, pivoxicam, tenoxicam, lornoxicam, and meloxicam.
Isoxicam has been suspended as a result of fatal skin reactions.
Chemistry
The physico-chemical characteristics of these molecules vary greatly depending upon the environment.
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:
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
- ^ 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.
- ^ 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.
| Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA) | |
|---|---|
| pyrazolones / pyrazolidines | |
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
| Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use. | |
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