N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide

• ChemBase ID: 828
• Molecular Formular: C17H25N3O2S
• Molecular Mass: 335.4643
• Monoisotopic Mass: 335.16674806
• SMILES: S(=O)(=O)(NC)CCc1cc2c(C3CCN(CC3)C)c[nH]c2cc1
• Canonical SMILES: CNS(=O)(=O)CCc1ccc2c(c1)c(c[nH]2)C1CCN(CC1)C
• 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
• InChIKey: AMKVXSZCKVJAGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 121679-13-8
• PubChem SID: 46507243; 160964291
• PubChem CID: 4440

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.549356
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.8418646
• LogD (pH = 7.4): -0.34287214
• Log P: 1.440625
• Molar Refractivity: 94.2572 cm^3
• Polarizability: 38.131832 Å^3
• Polar Surface Area: 65.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.16
• LOG S: -3.47
• Solubility (Water): 1.14e-01 g/l

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: 5-HT receptor

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00952

• 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

Selleck Chemicals - S1488

Research Area: Neurological Disease
Biological Activity:
Naratriptan(Amerge and Naramig) is a triptan drug that is used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist. [1]

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
• http://en.wikipedia.org/wiki/Naratriptan