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QuickView for naratriptan (compound)

Summary
General Info

PubChem

PubChem Compound 10545065

Name:	naratriptan
PubChem Compound ID:	10545065
Molecular formula:	C₁₇H₂₅N₃O₂S
Molecular weight:	339.477 g/mol

DrugBank

Identification

Name:	naratriptan
Name (isomeric):	DB00952
Drug Type:	small molecule
Brand:	Naramig, Amerge
Category:	Serotonin Agonists, Selective Serotonin Agonists, Vasoconstrictor Agents
CAS number:	121679-13-8

Pharmacology

Indication:	For the acute treatment of migraine attacks with or without aura in adults.
Pharmacology:	Naratriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonist. Naratriptan has only a weak affinity for 5-HT_1A, 5-HT_5A, and 5-HT₇ receptors and no significant affinity or pharmacolog... show more » Naratriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonist. Naratriptan has only a weak affinity for 5-HT_1A, 5-HT_5A, and 5-HT₇ receptors and no significant affinity or pharmacological activity at 5-HT₂, 5-HT₃ or 5-HT₄ receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Naratriptan also activates 5-HT₁ receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Naratriptan in humans. show less «
Mechanism of Action:	Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstricti... show more » Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism. show less «
Absorption:	Well absorbed (74% oral biovaility), absorption is rapid with peak plasma concentrations after 2-5 hours. The rate of absorption is slower during a migraine attack.
Protein binding:	28%-31% (over the concentration range of 50 to 1000 ng/mL)
Biotransformation:	Primarily hepatic. In vitro, naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.
Half Life:	5-8 hours
Clearance:	6.6 mL/min/kg
Toxicity:	Symptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Fluvoxamine	Increased risk of CNS adverse effects
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Vilazodone	Increased risk of serotonin syndrome
Ergonovine	Possible severe and prolonged vasocontriction
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.

Fluvoxamine	Increased risk of CNS adverse effects
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Vilazodone	Increased risk of serotonin syndrome
Ergonovine	Possible severe and prolonged vasocontriction
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Sibutramine	Increased risk of CNS adverse effects
Nefazodone	Increased risk of CNS adverse effects
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Escitalopram	Increased risk of CNS adverse effects
Dihydroergotamine	Naratriptan, a serotonin 5-HT1D receptor agonists, may increase the vasoconstricting effect of dihydroergotamine. Concomitant use of these two agents within 24 hours is contraindicated.
Phenelzine	The use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Sertraline	Increased risk of CNS adverse effects
Dihydroergotoxine	Possible severe and prolonged vasocontriction
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Ergotamine	Possible severe and prolonged vasoconstriction.
Isocarboxazid	The use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Citalopram	Increased risk of CNS adverse effects
Methylergonovine	Possible severe and prolonged vasocontriction
Fluoxetine	Increased risk of CNS adverse effects
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Methysergide	Possible severe and prolonged vasoconstriction.
Desvenlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Zolmitriptan	Concomitant use of two serotonin 5-HT1D receptor agonists, such as zolmitriptan and naratriptan, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
Paroxetine	Increased risk of CNS adverse effects

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Targets

5-hydroxytryptamine 1D receptor

This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity

UniProt ID:

P28221

Gene:

HTR1D

Actions:

agonist

References:

Hargreaves RJ, Shepheard SL: Pathophysiology of migraine--new insights. Can J Neurol Sci. 1999 Nov;26 Suppl 3:S12-9.
View Article

Donaldson C, Boers PM, Hoskin KL, Zagami AS, Lambert GA: The role of 5-HT1B and 5-HT1D receptors in the selective inhibitory effect of naratriptan on trigeminovascular neurons. Neuropharmacology. 2002 Mar;42(3):374-85.
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Pauwels PJ, Colpaert FC: Selective antagonism of human 5-HT1D and 5-HT1B receptor-mediated responses in stably transfected C6-glial cells by ketanserin and GR 127,935. Eur J Pharmacol. 1996 Apr 4;300(1-2):141-5.
View Article

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
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Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6.
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Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9.
View Article

Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109.
View Article

Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18.
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Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11.
View Article

Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87.
View Article

Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3.
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Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316.
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5-hydroxytryptamine 1B receptor

5-hydroxytryptamine 1F receptor

5-hydroxytryptamine 1A receptor