science

Naratriptan

Naratriptan is a science topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Naratriptan rather than just read about it. In short: Naratriptan, sold under the brand names Amerge and Naramig among others, is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. It is a selective serotonin 5-HT1 receptor family agonist.

Key takeaways

Naratriptan belongs to science; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Naratriptan to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Naratriptan from memory before moving on to harder problems.

Reference excerpt

Naratriptan, sold under the brand names Amerge and Naramig among others, is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. It is a selective serotonin 5-HT1 receptor family agonist. It was patented in 1987 and approved for medical use in 1997.

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.

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 and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment.

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. The risk of triptan side effects is also in general low, according to a systematic review. 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. The tingling and heaviness and sensation of warmth/heat is characteristic of selective 5-HT1 agonists.

Pharmacology

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.

Chemistry Naratriptan is a triptan and a modified analogue of tryptamines like the psychedelic drug dimethyltryptamine (DMT). However, naratriptan itself is not technically a tryptamine as it features a (1-methylpiperidin-4-yl) side chain instead of the ethylamine side chain present in tryptamines. Besides this difference, naratriptan is substituted at the 5 position of the indole ring system and the amine moiety has been cyclized. Instead of being a tryptamine, naratriptan is a piperidinylindole. The experimental log P of naratriptan is 1.6 to 2.16 and its predicted log P is 0.28 to 2.16.

History Naratriptan was patented in 1987 and was introduced for medical use in 1997.

Society and culture In the United States, the Food and Drug Administration (FDA) approved naratriptan on February 11, 1998. It was covered by U.S. Patent no. 4997841; the FDA lists the patent as expiring on July 7, 2010. In July 2010, in the wake of the patent expiration, several drug manufacturers, including Roxane Labs, Sandoz and Teva Pharmaceuticals, 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, and by Australian patent 611469 in Australia through June 17, 2013. 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. 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. 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. Following the Canadian quarantine, the United Arab Emirates' Ministry of Health also imposed a similar quarantine.

See also Triptan Piperidinylindole Substituted tryptamine § Related compounds

References

Illustrations

Worked examples

Example 1 — a first encounter with Naratriptan

Start with the simplest possible case. Write down what Naratriptan claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Naratriptan before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Naratriptan ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Naratriptan

In research: Naratriptan appears in science research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Naratriptan in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Naratriptan is common in secondary-school and first-year university syllabi. It links to neighbouring topics 5-HT1B agonists, 5-HT1D agonists, 5-HT1E agonists, so understanding it makes those chapters shorter.
In everyday life: Look for Naratriptan outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Naratriptan in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Naratriptan means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Naratriptan out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Naratriptan in simple terms?

Why does Naratriptan matter?

Because it connects several science ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Naratriptan?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Naratriptan.