Naratriptan

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Naratriptan
Naratriptan.svg
Naratriptan-3d-sticks.png
Systematic (IUPAC) name
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Clinical data
Trade names Amerge
AHFS/Drugs.com monograph
MedlinePlus a601083
Pregnancy cat.
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 74%
Metabolism Hepatic
Half-life 5-8 hours
Excretion Renal
Identifiers
CAS number 121679-13-8 YesY
ATC code N02CC02
PubChem CID 4440
IUPHAR ligand 45
DrugBank DB00952
ChemSpider 4287 YesY
UNII QX3KXL1ZA2 YesY
KEGG D08255 YesY
ChEBI CHEBI:7478 YesY
ChEMBL CHEMBL1278 YesY
Chemical data
Formula C17H25N3O2S 
Mol. mass 335.465 g/mol
 YesY (what is this?)  (verify)

Naratriptan (trade names include Amerge and Naramig) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. Naratriptan is available in 2.5 mg tablets. It is a selective 5-HT1 receptor subtype agonist.

Indication[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.[1]

Mechanism of action[edit]

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 5HT (serotonin) agonists.

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

Side effects[edit]

Side effects include: dizziness, drowsiness, tingling of the hands or feet, nausea, dry mouth and unsteadiness. If these effects persist or worsen, notify your doctor promptly. Side-effects which are unlikely and which should be promptly reported include: chest pain/pressure, throat pain/pressure, unusually fast/slow/irregular pulse, one-sided muscle weakness, vision problems, cold/bluish hands or feet, stomach pain, bloody diarrhea, mental/mood changes, and fainting. In the unlikely event you have a serious allergic reaction to this drug, seek immediate medical attention. Symptoms of a serious allergic reaction include: rash, itching, swelling, severe dizziness, trouble breathing (swelling of the throat).

The use of naratriptan with MAOIs and serotonergic drugs may result in the life threatening serotonin syndrome. Make sure your doctor/pharmacist is aware of all your current medications (including as needed medications) before taking this drug. [4]

Exclusivity[edit]

In the United States, the Food and Drug Administration (FDA) approved naratriptan on February 11, 1998.[5] It was covered by U.S. Patent no. 4997841; the FDA lists the patent as expiring on July 7, 2010.[5][6]

In July 2010, in the wake of the patent expiration, several drug manufacturers, including Roxane Labs,[7] Sandoz[8] and Teva Pharmaceuticals,[9] announced that they were launching generic Naratriptan medications.

The drug continues to be covered by European patent 0303507 in Germany, Spain, France and the United Kingdom through March 10, 2012,[10] and by Australian patent 611469 in Australia through June 17, 2013.[10] It had previously been covered by Canadian patent 1210968; but both Sandoz and Novopharm have offered generic equivalents in Canada since that patent's expiration December 1, 2009.[10]

Synthesis[edit]

Naratriptan synthesis: U.S. Patent 4,997,841

References[edit]

  1. ^ Medline Plus Drug Information for Naratriptan Accessed 6 August 2009
  2. ^ Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials. Cephalalgia 2002 Oct;22(8):633-58.
  3. ^ Efficacy of naratriptan tablets in the acute treatment of migraine: A dose-ranging study. Clin Ther 2000 Aug;22(8):970-80.
  4. ^ (( cite web | url = http://www.drugs.com/cdi/naratriptan.html ))
  5. ^ a b FDA AccessData entry for Naratriptan Hydrochloride, accessed September 8, 2008
  6. ^ U.S. Patent no. 4997841, Alexander W. Oxford, et al., Indole Derivatives, March 5, 1991
  7. ^ DeArment, Alaric (2010-07-09). "Roxane launches generic Amerge, Arimidex". Drug Store News. Retrieved 2010-07-23. 
  8. ^ DeArment, Alaric (2010-07-12). "Sandoz launches generic Amerge". Drug Store News. Retrieved 2010-07-23. 
  9. ^ DeArment, Alaric (2010-07-14). "Teva launches generic Amerge". Drug Store News. Retrieved 2010-07-23. 
  10. ^ a b c Oh, Dae (June 2010). "Drug In Focus: Naratriptan". GenericsWeb. Retrieved 2010-12-15.