Naratriptan

• Catalog No.: DB00952
• CAS Number: 121679-13-8
• M. F.: C17H25N3O2S
• M. W.: 335.4643

SYNONYMS

• IUPAC name: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
• IUPAC Traditional name: naratriptan
• Brand Name: Naramig; Amerge
• Synonyms: naratriptan

DATABASE IDS

• CAS Number: 121679-13-8
• PubChem CID: 4440
• PubChem SID: 46507243

PROPERTIES

• Hydrophobicity(logP): 1.6
• Solubility: 35 mg/mL

DETAILS

Description (English)

• Drug Groups: approved; investigational
• Description: Naratriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.
• 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 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.
• Toxicity: Symptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. In vitro, naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.
• 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.
• Half Life: 5-8 hours
• Protein Binding: 28%-31% (over the concentration range of 50 to 1000 ng/mL)
• Distribution: * 170 L
• Clearance: * 6.6 mL/min/kg
• References: Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [Pubmed] ; Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [Pubmed] ; Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. Pubmed
• Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. Pubmed
• Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. Pubmed