Naratriptan: Difference between revisions

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{{Drugbox
| verifiedrevid = 462258702
| IUPAC_name = ''N''-methyl-2-[3-(1-methylpiperidin-4-yl)-1''H''-indol-5-yl]ethanesulfonamide
| image = Naratriptan.svg
| image2 = Naratriptan-3d-sticks.png
<!--Clinical data-->
| tradename = Amerge
| Drugs.com = {{drugs.com|monograph|naratriptan-hydrochloride}}
| MedlinePlus = a601083
| pregnancy_AU = B3
| pregnancy_US = C
| legal_status = Rx-only
| routes_of_administration = [[Mouth|Oral]]
<!--Pharmacokinetic data-->
| bioavailability = 74%
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 5-8 hours
| excretion = [[Kidney|Renal]]
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 121679-13-8
| ATC_prefix = N02
| ATC_suffix = CC02
| PubChem = 4440
| IUPHAR_ligand = 45
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00952
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4287
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QX3KXL1ZA2
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08255
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 7478
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1278
<!--Chemical data-->
| C=17 | H=25 | N=3 | O=2 | S=1
| molecular_weight = 335.465 [[gram|g]]/[[mole (unit)|mol]]
| smiles = O=S(=O)(NC)CCc3ccc1c(c(cn1)C2CCN(C)CC2)c3
| InChI = 1/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
| InChIKey = AMKVXSZCKVJAGH-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AMKVXSZCKVJAGH-UHFFFAOYSA-N
}}
__NOTOC__
__NOTOC__
{{Naratriptan}}
{{Naratriptan}}
{{CMG}}; {{AE}} {{SS}}
{{CMG}}; {{AE}} {{SS}}
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==Overview==
==Overview==
'''Naratriptan''' (trade names include '''Amerge''' and '''Naramig''') is a [[triptan]] [[medication|drug]] marketed by [[GlaxoSmithKline]] and is used for the treatment of [[migraine]] [[headaches]]. Naratriptan is available in 2.5&nbsp;mg tablets. It is a selective [[5-HT1|5-HT<sub>1</sub>]] receptor subtype [[agonist]].


==Category==
==Category==
Serotonin Receptor Agonists; Antimigraine Agents


==FDA Package Insert==
==FDA Package Insert==
Line 30: Line 89:
'''| [[Naratriptan labels and packages|Labels and Packages]]'''
'''| [[Naratriptan labels and packages|Labels and Packages]]'''


==Mechanism of Action==
==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.<ref name=medline>Medline Plus Drug Information  for [http://www.nlm.nih.gov/medlineplus/druginfo/meds/a601083.html Naratriptan] Accessed 6 August 2009</ref>
 
==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 [[Triptans#Mechanism_of_action|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 [[sumatriptan]] and [[rizatriptan]] was more effective than placebo in reducing migraine symptoms at two hours<ref name=ferrari>Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials. [http://dx.doi.org/10.1016/S0149-2918(00)80068-5 Cephalalgia 2002 Oct;22(8):633-58.]</ref> and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment.<ref name=havanka>Efficacy of naratriptan tablets in the acute treatment of migraine: A dose-ranging study. [http://dx.doi.org/10.1016/S0149-2918(00)80068-5 Clin Ther 2000 Aug;22(8):970-80.]</ref>
 
==Side effects==
 
Side effects include: dizziness, [[lethargy | drowsiness]], [[paresthesia | tingling of the hands or feet]], nausea, [[xerostomia | 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, [[Raynaud's phenomenon | cold/bluish hands or feet]], stomach pain, bloody diarrhea, mental/mood changes, and [[Syncope (medicine)| fainting]]. In the unlikely event you have a serious allergic reaction to this drug, seek immediate medical attention. Symptoms of a [[anaphylaxis | serious allergic reaction]] include: rash, itching, swelling, severe dizziness, trouble breathing (swelling of the throat).
 
The use of naratriptan with [[MAOI]]s and [[serotonergic]] drugs may result in the life threatening [[serotonin syndrome]]. Make sure your doctor/pharmacist is aware of all your current medications (including [[pro re nata | as needed medications]]) before taking this drug. <ref>(( cite web | url = http://www.drugs.com/cdi/naratriptan.html ))</ref>


==Exclusivity==
In the United States, the [[Food and Drug Administration]] (FDA) approved naratriptan on February 11, 1998.<ref name=accessdata>FDA AccessData entry for [http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=020763&TABLE1=OB_Rx Naratriptan Hydrochloride], accessed September 8, 2008</ref>  It was covered by {{US patent|4997841|U.S. Patent no. 4997841}}; the FDA lists the patent as expiring on July 7, 2010.<ref name=accessdata/><ref>{{US patent|4997841|U.S. Patent no. 4997841}}, Alexander W. Oxford, ''et al.'', ''Indole Derivatives'', March 5, 1991</ref>
In July 2010, in the wake of the patent expiration, several drug manufacturers, including [[Roxane Labs]],<ref>{{cite news |url=http://drugstorenews.com/story.aspx?id=145645 |title=Roxane launches generic Amerge, Arimidex |first=Alaric |last=DeArment |work=Drug Store News |date=2010-07-09 |accessdate=2010-07-23}}</ref> [[Sandoz]]<ref>{{cite news |url=http://drugstorenews.com/story.aspx?id=145817 |title=Sandoz launches generic Amerge |first=Alaric |last=DeArment |work=Drug Store News |date=2010-07-12 |accessdate=2010-07-23}}</ref> and [[Teva Pharmaceuticals]],<ref>{{cite news |url=http://drugstorenews.com/story.aspx?id=146081 |title=Teva launches generic Amerge |first=Alaric |last=DeArment |work=Drug Store News |date=2010-07-14 |accessdate=2010-07-23}}</ref> 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,<ref name=GenericsWeb>{{cite news |url=http://www.genericsweb.com/druginfocus/Naratriptan_press_release |title=Drug In Focus: Naratriptan |first=Dae |last=Oh |work=GenericsWeb |date=June 2010 |accessdate=2010-12-15}}</ref> and by Australian patent 611469 in Australia through June 17, 2013.<ref name=GenericsWeb/>  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.<ref name=GenericsWeb/>
==References==
==References==


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{{Antimigraine preparations}}
{{Antimigraine preparations}}
[[Category:Drugs]]
[[Category:Drugs]]
[[Category:Piperidines]]
[[Category:Sulfonamides]]
[[Category:Triptans]]

Revision as of 19:51, 3 February 2014

Naratriptan
File:Naratriptan.svg
Clinical data
Trade namesAmerge
AHFS/Drugs.comMonograph
MedlinePlusa601083
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability74%
MetabolismHepatic
Elimination half-life5-8 hours
ExcretionRenal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC17H25N3O2S
Molar mass335.465 g/mol
3D model (JSmol)
  (verify)


Naratriptan
NARATRIPTAN tablet® FDA Package Insert
Indications and Usage
Dosage and Administration
Dosage Forms and Strengths
Contraindications
Warnings and Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Overdosage
Description
Clinical Pharmacology
Nonclinical Toxicology
Clinical Studies
How Supplied/Storage and Handling
Patient Counseling Information
Labels and Packages
Clinical Trials on Naratriptan
ClinicalTrials.gov

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Sheng Shi, M.D. [2]

For patient information about Naratriptan, click here

Synonyms / Brand Names:

Overview

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.

Category

Serotonin Receptor Agonists; Antimigraine Agents

FDA Package Insert

Indications and Usage | Dosage and Administration | Dosage Forms and Strengths | Contraindications | Warnings and Precautions | Adverse Reactions | Drug Interactions | Use in Specific Populations | Overdosage | Description | Clinical Pharmacology | Nonclinical Toxicology | Clinical Studies | How Supplied/Storage and Handling | Patient Counseling Information | Labels and Packages

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 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

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

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]

References

  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. ↑ 5.0 5.1 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. ↑ 10.0 10.1 10.2 Oh, Dae (June 2010). "Drug In Focus: Naratriptan". GenericsWeb. Retrieved 2010-12-15.

Template:Antimigraine preparations

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