Naratriptan

Naratriptan
Names
Trade namesAmerge, Naramig, others
IUPAC name
  • N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Clinical data
Drug classTriptan[1]
Main usesMigraine headaches[1]
Side effectsNumbness, nausea, sleepiness, tiredness[1]
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
    Routes of
    use    		By mouth
    Typical dose2.5 mg[2]
    External links
    AHFS/Drugs.comMonograph
    US NLMNaratriptan
    MedlinePlusa601083
    Legal
    Legal status
    • In general: ℞ (Prescription only)
    Pharmacokinetics
    Bioavailability74%
    MetabolismLiver
    Elimination half-life5-8 hours
    ExcretionKidney
    Chemical and physical data
    FormulaC17H25N3O2S
    Molar mass335.47 g·mol−1
    3D model (JSmol)
    SMILES
    • O=S(=O)(NC)CCc3ccc1c(c(c[nH]1)C2CCN(C)CC2)c3
    InChI
    • 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

    Naratriptan, sold under the brand name Amerge among others, is a medication used to treat migraine headaches.[1] It is not used preventatively.[1] It is taken by mouth.[1]

    Common side effects include numbness, nausea, sleepiness, and tiredness.[1] Other side effects may include coronary vasospasm, stroke, high blood pressure, serotonin syndrome, anaphylaxis, and medication overuse headache.[1] Safety in pregnancy is unclear.[3] It is a triptan which works as a selective 5-HT1 receptor agonist.[1]

    Naratriptan was patented in 1987 and approved for medical use in 1997.[4] It is available as a generic medication.[2] In the United Kingdom 6 tablets costs the NHS about £3 as of 2021.[2] This amount in the United States is about 11 USD.[5]

    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.[6]

    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[7] and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment.[8]

    Dosage

    It is generally taken as a dose of 2.5 mg.[2] A second dose can be take up to 4 hours later.[2]

    Side effects

    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).

    Those allergic to sulfonamides may also be allergic to naratriptan.[2]

    Mechanism of action

    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 5HT (serotonin) agonists.

    Society and culture

    In the United States, the Food and Drug Administration (FDA) approved naratriptan on February 11, 1998.[9] It was covered by U.S. Patent no. 4997841; the FDA lists the patent as expiring on July 7, 2010.[9][10]

    In July 2010, in the wake of the patent expiration, several drug manufacturers, including Roxane Labs,[11] Sandoz[12] and Teva Pharmaceuticals,[13] 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,[14] and by Australian patent 611469 in Australia through June 17, 2013.[14] 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.[14]

    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.[15][16] 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.[17]

    Following the Canadian quarantine, the United Arab Emirates' Ministry of Health also imposed a similar quarantine.[17][18]

    References

    1. 1 2 3 4 5 6 7 8 9 "Naratriptan Monograph for Professionals". Drugs.com. Archived from the original on 25 January 2021. Retrieved 11 November 2021.
    2. 1 2 3 4 5 6 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 501. ISBN 978-0857114105.
    3. ↑ "Naratriptan (Amerge) Use During Pregnancy". Drugs.com. Archived from the original on 25 November 2020. Retrieved 12 November 2021.
    4. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 531. ISBN 978-3-527-60749-5. Archived from the original on 2020-10-23. Retrieved 2021-10-24.
    5. ↑ "Naratriptan Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 31 October 2016. Retrieved 11 November 2021.
    6. ↑ "Naratriptan". Medline Plus Drug Information. U.S. National Library of Medicine. Archived from the original on 9 August 2009. Retrieved 6 August 2009.
    7. ↑ 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.
    8. ↑ 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.
    9. 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.
    10. ↑ US 4997841, Oxford AW, Sutina D, Owen MR, "Indole derivatives", issued 5 March 1991, assigned to Glaxo Group Ltd 
    11. ↑ DeArment A (2010-07-09). "Roxane launches generic Amerge, Arimidex". Drug Store News. Archived from the original on 2021-10-28. Retrieved 2010-07-23.
    12. ↑ DeArment A (2010-07-12). "Sandoz launches generic Amerge". Drug Store News. Archived from the original on 2021-10-28. Retrieved 2010-07-23.
    13. ↑ DeArment A (2010-07-14). "Teva launches generic Amerge". Drug Store News. Archived from the original on 2021-10-28. Retrieved 2010-07-23.
    14. 1 2 3 Oh D (June 2010). "Drug In Focus: Naratriptan". GenericsWeb. Archived from the original on 2017-01-06. Retrieved 2010-12-15.
    15. ↑ "Health products quarantined from two India sites". Health Canada. Government of Canada. December 24, 2014. Archived from the original on April 27, 2017. Retrieved September 14, 2017.
    16. ↑ "Health products quarantined from two sites in India as Health Canada assesses data integrity concerns". Recalls and safety alerts. Health Canada. December 23, 2014. Archived from the original on June 20, 2017. Retrieved September 14, 2017.
    17. 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. Archived from the original on September 15, 2017. Retrieved September 14, 2017.
    18. ↑ "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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