Naratriptan Hydrochloride

121679-13-8 Categories: , ,
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Product Details:

  • Product Name: Naratriptan Hydrochloride
  • CAS #: 121679-13-8
  • Mode 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) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.

  • Pharmacodynamics:

    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-HT1A, 5-HT5A, 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.

  • Metabolism:

    Primarily hepatic. In vitro, naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.

  • Toxicity:

    Symptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.

  • IUPAC: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
  • ATC: N02CC02
  • PubChem: 4440
  • DrugBank: DB00952 (APRD00220)
  • Formula: C17H25N3O2
  • Molecular Mass: 335.465
  • Synonyms: 143388-64-1, Amerge, GR 85548A, N-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide monohydrochloride, Naratriptan HCl, Naratriptan hydrochloride, UNII-10X8X4P12Z
  • SMILES: Cl.CNS(=O)(=O)CCc1ccc2[nH]cc(C3CCN(C)CC3)c2c1
  • AHFS Code: 28:32.3
  • InChl: 1S/C17H25N3O2S.ClH/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;1H
  • General Reference:
    1. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
    2. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]
    3. 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:15320857 ]
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