関: naratriptan hydrochloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/08 14:24:31」(JST)

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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-HT₁ receptor subtype agonist.

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 continued 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]

Synthesis

Naratriptan synthesis: U.S. Patent 4,997,841

References

^ Medline Plus Drug Information for Naratriptan Accessed 6 August 2009
^ 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.
^ Efficacy of naratriptan tablets in the acute treatment of migraine: A dose-ranging study. Clin Ther 2000 Aug;22(8):970-80.
^ (( cite web | url = http://www.drugs.com/cdi/naratriptan.html ))
^ ^a ^b FDA AccessData entry for Naratriptan Hydrochloride, accessed September 8, 2008
^ U.S. Patent no. 4997841, Alexander W. Oxford, et al., Indole Derivatives, March 5, 1991
^ DeArment, Alaric (2010-07-09). "Roxane launches generic Amerge, Arimidex". Drug Store News. Retrieved 2010-07-23.
^ DeArment, Alaric (2010-07-12). "Sandoz launches generic Amerge". Drug Store News. Retrieved 2010-07-23.
^ DeArment, Alaric (2010-07-14). "Teva launches generic Amerge". Drug Store News. Retrieved 2010-07-23.
^ ^a ^b ^c Oh, Dae (June 2010). "Drug In Focus: Naratriptan". GenericsWeb. Retrieved 2010-12-15.

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English Journal

Optimal balance of efficacy and tolerability of oral triptans and telcagepant: a review and a clinical comment.

Tfelt-Hansen P.SourceDepartment of Neurology, Danish Headache Center, University of Copenhagen, Glostrup Hospital, Glostrup, Denmark, ptha@glo.regionh.dk.
The journal of headache and pain.2011 Jun;12(3):275-80. Epub 2011 Feb 25.
Dose-response curves for headaches relief and adverse events (AEs) are presented for five triptans: sumatriptan, zolmitriptan, naratriptan, almotriptan, and frovatriptan, and the CGRP antagonist telcagepant. The upper part of the efficacy curve of the triptans is generally flat, the so-called ceilin
PMID 21350792

Triptans attenuate capsaicin-induced CREB phosphorylation within the trigeminal nucleus caudalis: a mechanism to prevent central sensitization?

Mitsikostas DD, Knight YE, Lasalandra M, Kavantzas N, Goadsby PJ.SourceHeadache Group, Department of Neurology, University of California, San Francisco, San Francisco, CA, USA, dmitsikostas@ath.forthnet.gr.
The journal of headache and pain.2011 May 29. [Epub ahead of print]
The c-AMP-responsive element binding protein (CREB) and its phosphorylated product (P-CREB) are nuclear proteins expressed after stimulation of pain-producing areas of the spinal cord. There is evidence indicating that central sensitization within dorsal horn neurons is dependent on P-CREB transcrip
PMID 21626018

Japanese Journal

New Synthesis of Naratriptan

Poszavacz Laszlo,Simig Gyula,Fetter Jozsef [他]
Heterocycles 68(4), 713-719, 2006-04-01
NAID 40007204647

Synthesis of 5-Substituted Indole Derivatives, Part 4: Naratriptan from α-Anilinoacetaldehyde Dimethylacetal by TiCl4-Mediated Cyclisation

Pete Bela,Simig Gyula,Poszavacz Laszlo [他]
Heterocycles 60(11), 2441-2455, 2003-11-01
NAID 80016191746

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「ナラトリプタン」

Naratriptan
Systematic (IUPAC) name
	N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Clinical data
Trade names	Amerge
AHFS/Drugs.com	monograph
MedlinePlus	a601083
Pregnancy; category	AU: B3; US: C (Risk not ruled out);
Legal status	℞ (Prescription only);
Routes of; administration	Oral
Pharmacokinetic data
Bioavailability	74%
Metabolism	Hepatic
Biological half-life	5-8 hours
Excretion	Renal
Identifiers
CAS Registry Number	121679-13-8
ATC code	N02CC02
PubChem	CID: 4440
IUPHAR/BPS	45
DrugBank	DB00952
ChemSpider	4287
UNII	QX3KXL1ZA2
KEGG	D08255
ChEBI	CHEBI:7478
ChEMBL	CHEMBL1278
Chemical data
Formula	C17H25N3O2S
Molecular mass	335.465 g/mol
	SMILES O=S(=O)(NC)CCc3ccc1c(c(cn1)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 ; Key:AMKVXSZCKVJAGH-UHFFFAOYSA-N ;
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