Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Naratriptan: Difference between pages

{{Short description|Chemical compound}}

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| image2 = Naratriptan 3D ball-and-stick.png

| tradename = Amerge, Naramig, others

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| C=17 | H=25 | N=3 | O=2 | S=1

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'''Naratriptan''' (trade names include '''Amerge''') is a [[triptan]] [[medication|drug]] marketed by [[GlaxoSmithKline]] and is used for the treatment of [[migraine]] [[headaches]]. It is a selective [[5-HT1|5-HT₁]] receptor subtype [[agonist]].

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It was patented in 1987 and approved for medical use in 1997.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=531 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA531 |language=en}}</ref>

==Medical uses==

Naratriptan is used for the treatment of the acute migraine attacks and the symptoms of migraine, including severe, throbbing headaches that sometimes are accompanied by nausea and sensitivity to sound or light.<ref name=medline>{{cite web | work = Medline Plus Drug Information | publisher = U.S. National Library of Medicine | url = https://www.nlm.nih.gov/medlineplus/druginfo/meds/a601083.html | title = Naratriptan | access-date = 6 August 2009 }}</ref>

===Efficacy===

A meta-analysis of 53 clinical trials has shown that all triptans are effective for treating migraine at marketed doses and that naratriptan, although less effective than [[sumatriptan]] and [[rizatriptan]] was more effective than placebo in reducing migraine symptoms at two hours<ref name=ferrari>{{cite journal | vauthors = Ferrari MD, Goadsby PJ, Roon KI, Lipton RB | s2cid = 2368571 | title = Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials | journal = Cephalalgia: An International Journal of Headache | volume = 22 | issue = 8 | pages = 633–58 | date = October 2002 | pmid = 12383060 | doi = 10.1046/j.1468-2982.2002.00404.x }}</ref> and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment.<ref name=havanka>{{cite journal | vauthors = Havanka H, Dahlöf C, Pop PH, Diener HC, Winter P, Whitehouse H, Hassani H, Naratriptan | display-authors = 6 | collaboration = S2WB2004 Study Group | title = Efficacy of naratriptan tablets in the acute treatment of migraine: a dose-ranging study. | journal = Clinical Therapeutics | date = August 2000 | volume = 22 | issue = 8 | pages = 970–80 | doi = 10.1016/S0149-2918(00)80068-5 | pmid = 10972633 }}</ref>

==Side effects==

Side effects are similar to other triptan medications, with the incidence of side effects reportedly being lower than sumatriptan, and side effects occurring rarely except when above 2.5mg.<ref>{{Cite journal |last=Massiou |first=H |date=2001 |title=Naratriptan |url=https://doi.org/10.1185/0300799039117016 |journal=[[Current Medical Research and Opinion]] |volume=17 |issue=1 |pages=51–53 |doi=10.1185/0300799039117016 |pmid=12463278 |s2cid=219185675 |issn=1473-4877}}</ref><ref name=":0">{{Cite journal |last=Mathew |first=Ninan T |date=May 1999 |title=Naratriptan: a review |url=http://www.tandfonline.com/doi/full/10.1517/13543784.8.5.687 |journal=Expert Opinion on Investigational Drugs |language=en |volume=8 |issue=5 |pages=687–695 |doi=10.1517/13543784.8.5.687 |pmid=15992123 |issn=1354-3784}}</ref> The risk of triptan side effects is also in general low, according to a systematic review.<ref name="pmid17883520">{{cite journal |vauthors=Pascual J, Mateos V, Roig C, Sanchez-Del-Rio M, Jiménez D |year=2007 |title=Marketed oral triptans in the acute treatment of migraine: a systematic review on efficacy and tolerability |journal=Headache |volume=47 |issue=8 |pages=1152–68 |doi=10.1111/j.1526-4610.2007.00849.x |pmid=17883520 |doi-access=free}}</ref> Side effects include: sensations of warmth/heat, dizziness, [[lethargy|drowsiness]], [[paresthesia|tingling of the hands or feet]], nausea, [[xerostomia|dry mouth]] and unsteadiness, chest pain/pressure, throat pain/pressure, unusually fast/slow/irregular pulse, and mental/mood changes.<ref name=":0" /> The tingling and heaviness and sensation of warmth/heat is characteristic of selective [[5-HT1|5-HT₁]] agonists.<ref name=":0" />

==Mechanism of action==

{{further|Serotonin receptor agonist|Triptan#Mechanism of action}}

The causes of migraine are not clearly understood; however, the efficacy of naratriptans and other triptans is believed to be due to their activity as [[Triptans#Mechanism of action|5-HT (serotonin) agonists]]. The biological and pharmacokinetic profile of naratriptan differs significantly from sumatriptan.<ref name=":0" />

==Society and culture==

In the United States, the [[Food and Drug Administration]] (FDA) approved naratriptan on February 11, 1998.<ref name=accessdata>{{cite web | work = Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations | url = http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=020763&TABLE1=OB_Rx | archive-url = https://web.archive.org/web/20160303214857/http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=020763&TABLE1=OB_Rx | archive-date = 3 March 2016 | title = Naratriptan Hydrochloride | access-date = 8 September 2008 | publisher = U.S. Food and Drug Administration }}</ref> It was covered by {{US patent|4997841|U.S. Patent no. 4997841}}; the FDA lists the patent as expiring on July 7, 2010.<ref name=accessdata/><ref>{{cite patent | number = 4997841 | country = US | inventor = Oxford AW, Sutina D, Owen MR | title = Indole derivatives | assign1= Glaxo Group Ltd | gdate = 5 March 1991 }}</ref>

In July 2010, in the wake of the patent expiration, several drug manufacturers, including [[Roxane Labs]],<ref>{{cite news |url=https://drugstorenews.com/pharmacy/roxane-launches-generic-amerge-arimidex |title=Roxane launches generic Amerge, Arimidex | vauthors = DeArment A |work=Drug Store News |date=2010-07-09 |access-date=2010-07-23 }}</ref> [[Sandoz]]<ref>{{cite news |url=https://drugstorenews.com/pharmacy/sandoz-launches-generic-amerge |title=Sandoz launches generic Amerge | vauthors = DeArment A |work=Drug Store News |date=2010-07-12 |access-date=2010-07-23 }}</ref> and [[Teva Pharmaceuticals]],<ref>{{cite news |url=https://drugstorenews.com/pharmacy/teva-launches-generic-amerge |title=Teva launches generic Amerge | vauthors = DeArment A |work=Drug Store News |date=2010-07-14 |access-date=2010-07-23 }}</ref> announced that they were launching generic Naratriptan medications.

The drug continued to be covered by European patent 0303507 in Germany, Spain, France and the United Kingdom through March 10, 2012,<ref name=GenericsWeb>{{cite news |url=http://www.genericsweb.com/druginfocus/Naratriptan_press_release |title=Drug In Focus: Naratriptan |vauthors=Oh D |work=GenericsWeb |date=June 2010 |access-date=2010-12-15 |archive-date=2017-01-06 |archive-url=https://web.archive.org/web/20170106182925/http://www.genericsweb.com/druginfocus/Naratriptan_press_release |url-status=dead }}</ref> and by Australian patent 611469 in Australia through June 17, 2013.<ref name=GenericsWeb/> It had previously been covered by Canadian patent 1210968; but both Sandoz and Teva (formerly Novopharm) have offered generic equivalents in Canada since that patent's expiration December 1, 2009.<ref name=GenericsWeb/>

On December 23, 2014, in response to a request from [[Health Canada]], importers in Canada agreed to [[quarantine]] the importation of health products, including generic Naratriptan manufactured for both Sandoz and Teva, from [[Dr. Reddy's Laboratories]] in [[Srikakulam]], [[India]].<ref>{{cite web |title=Health products quarantined from two India sites |url=http://www.hc-sc.gc.ca/dhp-mps/compli-conform/info-prod/drugs-drogues/advisory-avis-drreddys_ipca-eng.php |website=Health Canada |publisher=Government of Canada |access-date=September 14, 2017 |date=December 24, 2014}}</ref><ref>{{cite web |title=Health products quarantined from two sites in India as Health Canada assesses data integrity concerns |url=http://www.healthycanadians.gc.ca/recall-alert-rappel-avis/hc-sc/2014/43061a-eng.php |website=Recalls and safety alerts |publisher=Health Canada |access-date=September 14, 2017 |date=December 23, 2014}}</ref> Because Teva and Sandoz are the only approved suppliers of generic Naratriptan in Canada, the quarantine resulted in Naratriptan being placed on the Canadian drug shortage list.<ref name="pharmacompass">{{cite news |title=Dr. Reddy's largest API Facility Maybe the Next to Get Banned from Exporting to the United States |url=https://www.pharmacompass.com/radio-compass-blog/dr-reddy-s-largest-api-facility-maybe-the-next-to-get-banned-from-exporting-to-the-united-states |access-date=September 14, 2017 |work=PharmaCompass | publisher = LePro PharmaCompass OPC Private Limited |date=March 30, 2015 |language=en-gb}}</ref>

Following the Canadian quarantine, the [[United Arab Emirates]]' [[Ministry of Health (United Arab Emirates)|Ministry of Health]] also imposed a similar quarantine.<ref name="pharmacompass"/><ref>{{cite web | title = Stop the importation and distribution of Medical Products manufactured by Dr. Reddy's Laboratories in Srikakulam, India & IPCA Laboratories in Pithampur |url=https://www.haad.ae/HAAD/LinkClick.aspx?fileticket=KDlNvA7PC0s%3d&tabid=207 | archive-url = https://web.archive.org/web/20170915071335/https://www.haad.ae/HAAD/LinkClick.aspx?fileticket=KDlNvA7PC0s%3d&tabid=207 | archive-date = 15 September 2017 | series = Circular no. HRD/017/15 | work = Health Authority – Abu Dhabi (HAAD) |publisher=United Arab Emirates Ministry of Health |access-date= 14 September 2017 | date = 19 February 2015 }}</ref>

== References ==

{{Reflist|30em}}

{{Triptans}}

{{Serotonergics}}

{{Tryptamines}}

{{GlaxoSmithKline}}

[[Category:Triptans]]

[[Category:Piperidines]]

[[Category:Sulfonamides]]

[[Category:Drugs developed by GSK plc]]

[[Category:5-HT1D agonists]]

[[Category:5-HT1F agonists]]