Oxicam
Drug class
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.
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pyrazolidines
and related substances
- Ampiroxicam
- Droxicam
- Isoxicam
- Lornoxicam
- Meloxicam
- Piroxicam
- Pivoxicam
- Tenoxicam
derivatives (profens)
- Alminoprofen
- Benoxaprofen†
- Carprofen‡
- Dexibuprofen
- Dexketoprofen
- Fenbufen
- Fenoprofen
- Flunoxaprofen
- Flurbiprofen
- Ibuprofen#
- Ibuproxam
- Indoprofen†
- Ketoprofen
- Loxoprofen
- Miroprofen
- Naproxen
- Oxaprozin
- Pelubiprofen
- Piketoprofen
- Pirprofen
- Suprofen
- Tarenflurbil
- Tepoxalin‡
- Tiaprofenic acid
- Vedaprofen‡
- Zaltoprofen
- COX-inhibiting nitric oxide donator: Naproxcinod
acids (fenamates)
(coxibs)
combinations
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; †withdrawn drugs; ‡veterinary use.
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