Piroxicam: Difference between revisions

| legal_EU_comment = <ref>{{cite web | title = Active substance: piroxicam | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 10 December 2020 | url = https://www.ema.europa.eu/documents/psusa/piroxicam-list-nationally-authorised-medicinal-products-psusa/00002438/202004_en.pdf}}</ref>

| smilesSMILES = OC=2c1ccccc1S(=O)(=O)N(C)C=2C(=O)Nc3ccccn3

'''Piroxicam''' is a [[nonsteroidal anti-inflammatory drug]] (NSAID) of the [[oxicam]] class used to relieve the symptoms of painful inflammatory conditions like [[arthritis]].<ref name = MD/><ref>{{cite journalweb | title=TGA Approved Terminology for Medicines, Section 1 – Chemical Substances | date=July 1999 | publisherwork = Therapeutic Goods Administration, Department of Health and Ageing, | publisher = Australian Government | page=97 | url=http://www.tga.gov.au/pdf/medicines-approved-terminology-chemical.pdf }}</ref> Piroxicam works by preventing the production of endogenous [[prostaglandins]] which are involved in the mediation of pain, stiffness, tenderness and swelling.<ref name = MD/> The medicine is available as [[capsule (pharmacy)|capsules]], [[tablet (pharmacy)|tablets]] and (not, in allsome countries), as a prescription-free [[gel]] 0.5%.<ref name = BNF/> It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract.<ref name = MD>{{cite web|title=Piroxicam|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|date=14 January 2014|access-date=24 June 2014|url=http://www.medicinescomplete.com/mc/martindale/current/ms-2692-v.htm|editorveditors=Brayfield, A|location=London, UK|archive-date=28 August 2021|archive-url=https://web.archive.org/web/20210828225223/https://about.medicinescomplete.com/wp-content/plugins/revslider/public/assets/js/jquery.themepunch.revolution.min.js?ver=5.4.5.2|url-status=dead}}</ref> Piroxicam is one of the few NSAIDs that can be given parenteral routes.{{cn|date=September 2022}}

It was patented in 1968 by [[Pfizer]] and approved for medical use in 1979.<ref name=Fis2006>{{cite book |last1 vauthors = Fischer |first1=JnosJ, |last2=Ganellin |first2=C. RobinCR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=519 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA519 |language=en}}</ref> It became generic in 1992,<ref name=NRDD/> and is marketed worldwide under many brandnames.<ref name=drugsInternat/>

It is used in the treatment of certain inflammatory conditions like [[rheumatoid arthritis|rheumatoid]] and [[osteoarthritis]], primary [[dysmenorrhoea]], and postoperative pain; andit actacts as an [[analgesic]], especially where there is an [[inflammation|inflammatory]] component.<ref name = MD/> The [[European Medicines Agency]] issued a review of its use in 2007 and recommended that its use be limited to the treatment of chronic inflammatory conditions, as it is only in these circumstances that its risk-benefit ratio proves to be favourable.<ref name = BNF/><ref name = EMA>{{cite web|title=COMMITTEECommittee FORfor MEDICINALmedicinal PRODUCTSproducts FORfor HUMANhuman USEuse (CHMP) OPINIONopinion FOLLOWINGfollowing ANan ARTICLEArticle 31(2) REFERRALreferral PIROXICAMfor CONTAININGPiroxicam MEDICINALcontaining PRODUCTSmedicinal products|work=European Medicines Agency|publisher=European Medicines Agency|date=20 September 2007|location=London, UK|access-date=24 June 2014|url=http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Piroxicam_31/WC500011770.pdf}}</ref>

As with other NSAIDs the principal side effects include: digestive complaints like [[nausea]], discomfort, [[diarrhoea]] and bleeds or ulceration of the [[stomach]], as well as [[headache]], dizziness, nervousness, [[depression (mood)|depression]], drowsiness, [[insomnia]], vertigo, hearing disturbances (such as [[tinnitus]]), [[hypertension|high blood pressure]], [[oedema]], light sensitivity, skin reactions (including, albeit rarely, [[Stevens–Johnson syndrome]] and [[toxic epidermal necrolysis]]) and rarely, [[kidney failure]], [[pancreatitis]], [[liver]] damage, visual disturbances, pulmonary [[eosinophilia]] and [[fibrosing alveolitis]].<ref name="BNF">{{cite book | isbn = 978-0-85711-084-8 | title = British National Formulary (BNF) | last1 = Joint Formulary Committee | year = 2013 | publisher = Pharmaceutical Press | location = London, UK | edition = 65 | pages = [https://archive.org/details/bnf65britishnati0000unse/page/665 665, 673–674] | url = https://archive.org/details/bnf65britishnati0000unse/page/665 }}</ref> Compared to other NSAIDs it is more prone to causing gastrointestinal disturbances and serious skin reactions.<ref name = BNF/>

Piroxicam is an NSAID and, as such, is a non-selective [[cyclooxygenase|COX]] [[COX-2 inhibitor|inhibitor]] possessing both analgesic and [[antipyretic]] properties.<ref name = BNF/>

Piroxicam exists as [[Enol|alkenol]] [[tautomer]] in organic solvents and as [[zwitterion]]ic form in water.<ref>{{cite journal |vauthors=Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L | title = Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study | journal = RSC Advances | volume = 5 | issue = 40 | pages = 31852–31860 | year = 2015 | doi=10.1039/c5ra03653d| bibcode = 2015RSCAd...531852I | doi-access = free }}</ref>

The project that produced piroxicam began in 1962 at [[Pfizer]]; the first clinical trial results were reported in 1977, and the product launched in 1980 under the brand name "Feldene".<ref name=NRDD>{{cite journal | pmidvauthors = 15459676Lombardino |JG, doi=10.1038/nrd1523Lowe | volume=3JA | title = The role of the medicinal chemist in drug discovery--then and now | year=2004 | journal =Nat RevNature Reviews. Drug DiscovDiscovery | pagesvolume =853–62 3 | last1issue = Lombardino10 | first1pages = JG853–862 | last2date = LoweOctober 2004 | first2pmid = JA15459676 3rd| issuedoi = 10.1038/nrd1523 | s2cid = 11225541 | doi-access = free }}. See: [http://www.nature.com/nrd/journal/v3/n10/box/nrd1523_BX1.html] Box 1: Discovery of piroxicam (1962–1980)</ref><ref>{{cite journal | vauthors = Weintraub M, Jacox RF, Angevine CD, Atwater EC | title = Piroxicam (CP 16171) in rheumatoid arthritis: a controlled clinical trial with novel assessment techniques | journal = The Journal of Rheumatology | volume = 4 | issue = 4 | pages = 393–404 | year = 1977 | pmid = 342691 }}</ref> Major patents expired in 1992<ref name=NRDD/> and the drug is marketed worldwide under many brandnames.<ref name=drugsInternat>{{cite web | work = Drugs.com [| url = https://www.drugs.com/international/piroxicam.html Drugs.com| internationaltitle = International listings for piroxicam] Page| accessedaccess-date July= 3, July 2015 }}</ref>

== See also ==

* [[Meloxicam]]

* [[Isoxicam]]

* [[Lornoxicam]]

== References ==

{{reflistReflist}}

== Further reading ==

[[Category:Pyridines2-Pyridyl compounds]]

[[Category:PfizerDrugs brandsdeveloped by Pfizer]]