ناراتریپتان

Also known as Amerge®, GR-85548A, N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide, N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide, N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide, Naratriptan, Naratriptanum, N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide

Naratriptan, sold under the brand names Amerge and Naramig among others, is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. It is a selective serotonin 5-HT1 receptor family agonist.

Chemical data

Formula: C17H25N3O2S
Molecular weight: 335.5 g/mol
IUPAC name: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
InChIKey: AMKVXSZCKVJAGH-UHFFFAOYSA-N
XLogP: 2
Polar surface area: 73.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1998
Admin. routes: oral
Indications: Headache, migraine disorder

via ChEMBL · EBI

Research

364 papers

Naratriptan.2006
Naratriptan is as effective as sumatriptan for the treatment of migraine attacks when used properly. A mini-review.Cephalalgia : an international journal of headache · 2021
Naratriptan.Current medical research and opinion · 2001
Naratriptan.International journal of clinical practice · 1999
Preclinical neuropharmacology of naratriptan.CNS drug reviews · 2005

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 335.166748
Has use: medication

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chemical formula: C₁₇H₂₅N₃O₂S
canonical SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
Commons category: Naratriptan
World Health Organisation international non-proprietary name: naratriptan
defined daily dose: 2.5
medical condition treated: migraine
significant drug interaction: linezolid

Sources (3)

via Wikidata · CC0

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via Wikidata sitelinks · CC0