Naratriptan

CAS No:
121679-13-8 Categories: , ,
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Product Details:

  • CAS No: 121679-13-8
  • AHFC code: 28:32.3
  • Synonyms:
  • ATC Code: N02CC02
  • Chemical Formula: C22H25F2NO4
  • Molecular Weight: 335.464
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00952 (APRD00220)
  • SMILES: CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1
  • InChl: AMKVXSZCKVJAGH-UHFFFAOYSA-N
  • PubChem: 4440
  • IUPAC: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide

Additional Details

Indication:
For the acute treatment of migraine attacks with or without aura in adults.
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.
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.
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.
General Reference:
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
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