Oxicam

{{Short description|Drug class}} [[File:Piroxicam.svg|class=skin-invert-image|thumb|Piroxicam, the most popular drug of the oxicam class.<ref name=pmid8162655/>]]

'''Oxicam''' is a class of non-steroidal anti-inflammatory drugs (NSAIDs),<ref name=RSC>{{Cite journal|vauthors=Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L|date=March 2015|title=Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study|journal=RSC Advances|publisher=Royal Society of Chemistry|location=England, UK|volume=5|pages=31852–31860|issue=40|doi=10.1039/c5ra03653d|bibcode=2015RSCAd...531852I |doi-access=free}}</ref> meaning that they have anti-inflammatory, analgesic, and antipyretic therapeutic effects. Oxicams bind closely to plasma proteins.<ref name=pmid8162655>{{Cite journal|vauthors=Olkkola KT, Brunetto AV, Mattila MJ|date=February 1994|title=Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents|journal=Clinical Pharmacokinetics|volume=26|issue=2|pages=107–20|pmid=8162655|doi=10.2165/00003088-199426020-00004|s2cid=13300943 }}</ref> 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.<ref name=Mutschler>{{Cite book|last=Mutschler|first=Ernst|author2=Gerd Geisslinger|author3=Heyo K. Kroemer|author4=Monika Schäfer-Korting|date=2001|title=Mutschler Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie; mit einführenden Kapiteln in die Anatomie, Physiologie und Pathophysiologie|language=German|trans-title=Mutster medicine effects: Textbook of pharmacology and toxicology; with introductory chapters in anatomy, physiology and pathophysiology|publisher=Wissenschaftliche Verlagsgesellschaft|location=Stuttgart, Germany|edition=8|page=233|isbn=3-8047-1763-2|ol=12928661M|oclc=48723029}}</ref>

The most popular drug of the oxicam class is piroxicam.<ref name=pmid8162655/> Other examples include: ampiroxicam, droxicam, pivoxicam, tenoxicam, lornoxicam,<ref name=pmid8162655/> and meloxicam.

Isoxicam has been suspended as a result of fatal skin reactions.<ref name=pmid8162655/>

==Chemistry== The physico-chemical characteristics of these molecules vary greatly depending upon the environment.<ref name=pmid12659890>{{Cite journal|vauthors=Banerjee R, Chakraborty H, Sarkar M|date=April 2003|title=Photophysical studies of oxicam group of NSAIDs: piroxicam, meloxicam and tenoxicam|journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy|publisher=Elsevier|volume=59|issue=6|pages=1213–22|bibcode=2003AcSpA..59.1213B|doi=10.1016/S1386-1425(02)00300-1|pmid=12659890}}</ref>

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:<ref name=RSC/> class=skin-invert-image|850px

==Side effects== {{Unreferenced medical section|date=February 2022}} The use of NSAIDs can, rarely, trigger severe cutaneous adverse reactions such as Stevens–Johnson syndrome (SJS) and toxic epidermal necrolysis (TEN).<ref>{{Cite journal |last1=Ward |first1=Kristina E. |last2=Archambault |first2=Raoul |last3=Mersfelder |first3=Tracey L. |date=2010-02-01 |title=Severe adverse skin reactions to nonsteroidal antiinflammatory drugs: A review of the literature |journal=American Journal of Health-System Pharmacy |volume=67 |issue=3 |pages=206–213 |doi=10.2146/ajhp080603 |issn=1535-2900 |pmid=20101062}}</ref> Epidemiologic studies and reviews have reported that, among NSAIDs, the oxicam derivatives (e.g., piroxicam, tenoxicam, meloxicam) are associated with a comparatively higher risk of SJS/TEN, particularly early after starting treatment, although the absolute risk remains low.<ref>{{Cite journal |last1=Mockenhaupt |first1=Maja |last2=Kelly |first2=Judith Parsells |last3=Kaufman |first3=David |last4=Stern |first4=Robert S. |last5=SCAR Study Group |date=|title=The risk of Stevens-Johnson syndrome and toxic epidermal necrolysis associated with nonsteroidal antiinflammatory drugs: a multinational perspective |journal=The Journal of Rheumatology |volume=30 |issue=10 |pages=2234–2240 |issn=0315-162X |pmid=14528522}}</ref><ref name="Harr2010">{{cite journal |last1=Harr |first1=T. |last2=French |first2=L. E. |year=2010 |title=Toxic epidermal necrolysis and Stevens-Johnson syndrome |journal=Orphanet Journal of Rare Diseases |volume=5 |article-number=39 |doi=10.1186/1750-1172-5-39 |doi-access=free |pmc=3021447 |pmid=21162721}}</ref>

Isoxicam was withdrawn/suspended from marketing after reports of fatal skin reactions.<ref name="Olkkola1994">{{cite journal |last1=Olkkola |first1=K. T. |last2=Brunetto |first2=A. V. |last3=Mattila |first3=M. J. |year=1994 |title=Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents |journal=Clinical Pharmacokinetics |volume=26 |issue=2 |pages=107–120 |doi=10.2165/00003088-199426020-00004 |pmid=8162655}}</ref>

==References== <references/>

Category:Dermatoxins Category:Nonsteroidal anti-inflammatory drugs Category:Sultams