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Naratriptan
Systematic (IUPAC) name
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1 H-indol-5-yl]ethanesulfonamide
Identifiers
CAS number 121679-13-8
ATC code N02CC02
PubChem 4440
DrugBank APRD00220
Chemical data
Formula C 17H25N3O2S 
Mol. mass 335.465 g/mol
Pharmacokinetic data
Bioavailability 74%
Metabolism Hepatic
Half life 5-8 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat. B3(AU) C(US)
Legal status Prescription only
Routes Oral
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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-hydroxytryptamine1 receptor subtype agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-( 1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide.

Contents

Indication

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

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

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 sumpatriptan 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

Side effects include: dizziness, drowsiness, tingling of the hands or feet, unusual tiredness, 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.

The U.S. Food and Drug Administration (FDA) approved naratriptan on February 11, 1998.[4] It is covered by U.S. Patent no. 4997841; the FDA lists the patent as scheduled for expiration on July 7, 2010.[5][4]

References

  1. ^ Medline Plus Drug Information for Naratriptan Accessed 6th 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. ^ a b FDA AccessData entry for Naratriptan Hydrochloride, accessed September 8, 2008
  5. ^ U.S. Patent no. 4997841, Alexander W. Oxford, et al., Indole Derivatives, March 5, 1991







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