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Naratriptan

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Naratriptan
Clinical data
Trade namesAmerge, Naramig, others
AHFS/Drugs.comMonograph
MedlinePlusa601083
Pregnancy
category
  • AU: B3
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability74%
MetabolismHepatic
Elimination half-life5-8 hours
ExcretionRenal
Identifiers
  • N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.121.501 Edit this at Wikidata
Chemical and physical data
FormulaC17H25N3O2S
Molar mass335.47 g·mol−1
3D model (JSmol)
  • O=S(=O)(NC)CCc3ccc1c(c(c[nH]1)C2CCN(C)CC2)c3
  • InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3 checkY
  • Key:AMKVXSZCKVJAGH-UHFFFAOYSA-N checkY
  (verify)

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

It was patented in 1987 and approved for medical use in 1997.[1]

Medical uses

[edit]

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.[2]

Efficacy

[edit]

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[3] and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment.[4]

Side effects

[edit]

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.[5][6] The risk of triptan side effects is also in general low, according to a systematic review.[7] Side effects include: sensations of warmth/heat, dizziness, drowsiness, tingling of the hands or feet, nausea, dry mouth and unsteadiness, chest pain/pressure, throat pain/pressure, unusually fast/slow/irregular pulse, and mental/mood changes.[6] The tingling and heaviness and sensation of warmth/heat is characteristic of selective 5-HT1 agonists.[6]

Mechanism of action

[edit]
Further information: Serotonin receptor agonist and 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 5-HT (serotonin) agonists. The biological and pharmacokinetic profile of naratriptan differs significantly from sumatriptan.[6]

Society and culture

[edit]

In the United States, the Food and Drug Administration (FDA) approved naratriptan on February 11, 1998.[8] It was covered by U.S. Patent no. 4997841; the FDA lists the patent as expiring on July 7, 2010.[8][9]

In July 2010, in the wake of the patent expiration, several drug manufacturers, including Roxane Labs,[10] Sandoz[11] and Teva Pharmaceuticals,[12] 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,[13] and by Australian patent 611469 in Australia through June 17, 2013.[13] 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.[13]

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.[14][15] 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.[16]

Following the Canadian quarantine, the United Arab Emirates' Ministry of Health also imposed a similar quarantine.[16][17]

References

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  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 978-3-527-60749-5.
  2. ^ "Naratriptan". Medline Plus Drug Information. U.S. National Library of Medicine. Retrieved 6 August 2009.
  3. ^ Ferrari MD, Goadsby PJ, Roon KI, Lipton RB (October 2002). "Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials". Cephalalgia: An International Journal of Headache. 22 (8): 633–58. doi:10.1046/j.1468-2982.2002.00404.x. PMID 12383060. S2CID 2368571.
  4. ^ Havanka H, Dahlöf C, Pop PH, Diener HC, Winter P, Whitehouse H, et al. (S2WB2004 Study Group) (August 2000). "Efficacy of naratriptan tablets in the acute treatment of migraine: a dose-ranging study". Clinical Therapeutics. 22 (8): 970–80. doi:10.1016/S0149-2918(00)80068-5. PMID 10972633.
  5. ^ Massiou H (2001). "Naratriptan". Current Medical Research and Opinion. 17 (1): 51–53. doi:10.1185/0300799039117016. ISSN 1473-4877. PMID 12463278. S2CID 219185675.
  6. ^ a b c d Mathew NT (May 1999). "Naratriptan: a review". Expert Opinion on Investigational Drugs. 8 (5): 687–695. doi:10.1517/13543784.8.5.687. ISSN 1354-3784. PMID 15992123.
  7. ^ Pascual J, Mateos V, Roig C, Sanchez-Del-Rio M, Jiménez D (2007). "Marketed oral triptans in the acute treatment of migraine: a systematic review on efficacy and tolerability". Headache. 47 (8): 1152–68. doi:10.1111/j.1526-4610.2007.00849.x. PMID 17883520.
  8. ^ a b "Naratriptan Hydrochloride". Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations. U.S. Food and Drug Administration. Archived from the original on 3 March 2016. Retrieved 8 September 2008.
  9. ^ US 4997841, Oxford AW, Sutina D, Owen MR, "Indole derivatives", issued 5 March 1991, assigned to Glaxo Group Ltd 
  10. ^ DeArment A (2010-07-09). "Roxane launches generic Amerge, Arimidex". Drug Store News. Retrieved 2010-07-23.
  11. ^ DeArment A (2010-07-12). "Sandoz launches generic Amerge". Drug Store News. Retrieved 2010-07-23.
  12. ^ DeArment A (2010-07-14). "Teva launches generic Amerge". Drug Store News. Retrieved 2010-07-23.
  13. ^ a b c Oh D (June 2010). "Drug In Focus: Naratriptan". GenericsWeb. Archived from the original on 2017-01-06. Retrieved 2010-12-15.
  14. ^ "Health products quarantined from two India sites". Health Canada. Government of Canada. December 24, 2014. Retrieved September 14, 2017.
  15. ^ "Health products quarantined from two sites in India as Health Canada assesses data integrity concerns". Recalls and safety alerts. Health Canada. December 23, 2014. Retrieved September 14, 2017.
  16. ^ a b "Dr. Reddy's largest API Facility Maybe the Next to Get Banned from Exporting to the United States". PharmaCompass. LePro PharmaCompass OPC Private Limited. March 30, 2015. Retrieved September 14, 2017.
  17. ^ "Stop the importation and distribution of Medical Products manufactured by Dr. Reddy's Laboratories in Srikakulam, India & IPCA Laboratories in Pithampur". Health Authority – Abu Dhabi (HAAD). Circular no. HRD/017/15. United Arab Emirates Ministry of Health. 19 February 2015. Archived from the original on 15 September 2017. Retrieved 14 September 2017.
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