Naratriptan

Last updated
Naratriptan
Naratriptan.svg
Naratriptan 3D ball-and-stick.png
Clinical data
Trade names Amerge, Naramig, others
AHFS/Drugs.com Monograph
MedlinePlus a601083
Pregnancy
category
  • AU:B3
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 74%
Metabolism Hepatic
Elimination half-life 5-8 hours
Excretion Renal
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 InfoCard 100.121.501 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H25N3O2S
Molar mass 335.47 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 Yes check.svgY
  • Key:AMKVXSZCKVJAGH-UHFFFAOYSA-N Yes check.svgY
   (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.

Contents

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

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. [2]

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

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. [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

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

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]

Related Research Articles

<span class="mw-page-title-main">Sumatriptan</span> 5-HT receptor agonist medication used for migraines & cluster headaches

Sumatriptan, sold commonly under brand names Imitrex and Treximet among others, is a medication used to treat migraine headaches and cluster headaches. It is taken orally, intranasally, or by subcutaneous injection. Therapeutic effects generally occur within three hours.

<span class="mw-page-title-main">Ergotamine</span> Chemical compound in the ergot family of alkaloids

Ergotamine, sold under the brand names Cafergot and Ergomar among others, is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.

<span class="mw-page-title-main">Frovatriptan</span> Chemical compound

Frovatriptan, sold under the brand name Frova, is a triptan drug developed by Vernalis for the treatment of migraine headaches and for short term prevention of menstrual migraine. The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.

<span class="mw-page-title-main">Triptan</span> Class of pharmaceutical drugs

Triptans are a family of tryptamine-based drugs used as abortive medication in the treatment of migraines and cluster headaches. This drug class was first commercially introduced in the 1990s. While effective at treating individual headaches, they do not provide preventive treatment and are not considered a cure. They are not effective for the treatment of tension–type headache, except in persons who also experience migraines. Triptans do not relieve other kinds of pain.

<span class="mw-page-title-main">Rizatriptan</span> Medication used for the treatment of migraine headaches

Rizatriptan, sold under the brand name Maxalt among others, is a medication used for the treatment of migraine headaches. It is taken by mouth.

<span class="mw-page-title-main">Zolmitriptan</span> Medication used in treatment of migraines

Zolmitriptan, sold under the brand name Zomig among others, is a triptan used in the acute treatment of migraine attacks with or without aura and cluster headaches. It is a selective serotonin receptor agonist of the 1B and 1D subtypes.

<span class="mw-page-title-main">Dihydroergotamine</span> An ergot alkaloid used to treat migraines

Dihydroergotamine (DHE), sold under the brand names D.H.E. 45 and Migranal among others, is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy similar to that of sumatriptan. Nausea is a common side effect.

Caffeine/ergotamine is the proprietary name of a medication consisting of ergotamine tartrate and caffeine. This combination is used for the treatment of headaches, such as migraine headache.

<span class="mw-page-title-main">Methysergide</span> Chemical compound

Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to adverse effects. It is taken by mouth.

<span class="mw-page-title-main">Almotriptan</span> Chemical compound

Almotriptan is a triptan medication discovered and developed by Almirall for the treatment of heavy migraine headache.

<span class="mw-page-title-main">Eletriptan</span> Chemical compound

Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">Glatiramer acetate</span> Medication

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<span class="mw-page-title-main">Antimigraine drug</span> Medication intended to reduce the effects or intensity of migraine headache

Antimigraine drugs are medications intended to reduce the effects or intensity of migraine headache. They include drugs for the treatment of acute migraine symptoms as well as drugs for the prevention of migraine attacks.

Sumatriptan/naproxen, sold under the brand name Treximet among others, is a fixed-dose combination medication used to treat migraines. It is taken by mouth. It contains sumatriptan, as the succinate, a serotonin 5-hydroxytryptamine (5-HT) 1b/1d receptor agonist (triptan); and naproxen as the sodium salt, a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs).

Triptans is a word commonly used for a class of anti-migraine drugs that are selective 5-hydroxytryptamine/serotonin1B/1D (5-HT1B/1D) agonists. Migraine is a complex disease which affects about 15% of the population and can be highly disabling. Triptans have advantages over ergotamine and dihydroergotamine, such as selective pharmacology, well established safety record and evidence-based prescribing instructions. Triptans are therefore often preferred treatment in migraine.

<span class="mw-page-title-main">Lasmiditan</span> Chemical compound

Lasmiditan, sold under the brand name Reyvow, is a medication used for the acute treatment of migraine with or without aura in adults. It is not useful for prevention. It is taken by mouth.

<span class="mw-page-title-main">Donitriptan</span> Chemical compound

Donitriptan (INN) is a triptan drug which was investigated as an antimigraine agent but ultimately was never marketed. It acts as a high-affinity, high-efficacy/near-full agonist of the 5-HT1B and 5-HT1D receptors, and is among the most potent of the triptan series of drugs. Donitriptan was being developed in France by bioMérieux-Pierre Fabre and made it to phase II clinical trials in Europe before development was discontinued.

<span class="mw-page-title-main">CP-122,288</span> Chemical compound

CP-122,288 is a drug which acts as a potent and selective agonist for the 5-HT1B, 5-HT1D and 5-HT1F serotonin receptor subtypes. It is a derivative of the migraine medication sumatriptan, but while CP-122,288 is 40,000 times more potent than sumatriptan as an inhibitor of neurogenic inflammation and plasma protein extravasation, it is only twice as potent as a constrictor of blood vessels. In human trials, CP-122,288 was not found to be effective as a treatment for migraine, but its selectivity for neurogenic anti-inflammatory action over vasoconstriction has made it useful for research into the underlying causes of migraine.

Fremanezumab, sold under the brand name Ajovy, is a medication used to prevent migraines in adults. It is given by injection under the skin.

References

  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.
  6. 1 2 3 4 Mathew, Ninan T (May 1999). "Naratriptan: a review". Expert Opinion on Investigational Drugs. 8 (5): 687–695. doi:10.1517/13543784.8.5.687. ISSN   1354-3784.
  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. 1 2 "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. 1 2 3 Oh D (June 2010). "Drug In Focus: Naratriptan". GenericsWeb. 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. 1 2 "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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