Basic information
- CAS
121679-13-8- Standard SMILES
CNS(=O)(=O)CCc1ccc2[nH]cc(C3CCN(C)CC3)c2c1- InChIKey
AMKVXSZCKVJAGH-UHFFFAOYSA-N- Molecular formula
- C17H25N3O2S
- Average molar mass
- 335.5 g/mol
- Monoisotopic mass
- 335.16674804
Overview
Naratriptan is a member of tryptamines, a sulfonamide and a heteroarylpiperidine. It has a role as a serotonergic agonist and a vasoconstrictor agent.
Names & identifiers
- Preferred name
- Naratriptan
- IUPAC
- N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
- English name
- Naratriptan
- Molecular formula
- C17H25N3O2S
- Molecular weight
- 335.46
Names & synonyms
naratriptan121679-13-8NaramigN-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamidenaratriptanum1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamideQX3KXL1ZA2N-Methyl-2-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)ethanesulfonamideN-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamideCHEBI:7478DTXSID7023354
Show more names
Naratriptan1NaratriptaneNaratriptan(Amerge)Naratriptan, 10 mM in DMSOAMERGEGR-85548AN-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]ethanesulfonamideInhibitor,GR-85548A,5-hydroxytryptamine Receptor,inhibit,Serotonin Receptor,5-HT Receptor,Naratriptan
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamideN-methyl-2-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamideN-methyl-2-(3-(1-methyl-4-piperidyl)-1H-indol-5-yl)-ethanesulfonamideRefChem:57988DTXCID003354N02CC02N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide601-800-8
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 73.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 483
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
LogP1.6
Solubility1.14e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Serotonin Receptor Agonists; Serotonin 5-HT1 Receptor Agonists; Triptans; Vasoconstrictor Agents
Pharmaceuticals
Melting Point246 °C (hydrochloride salt)
Physical DescriptionSolid
Collision Cross Section174.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 170 · 170-171°
- Boiling point
- 541.3 · 541.3±60.0 °C(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Treatment
There is no specific antidote to naratriptan. Standard supportive treatment should be applied as required. If the patient presents with chest pain or other symptoms consistent with angina pectoris, ECG monitoring should be performed for evidence of ischemia. (L1712)
Exposure RoutesWell 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.
Toxicity Summary
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.
Signs and SymptomsSymptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
naratriptan
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
N02CC02
N - Nervous system
QN - Nervous system
Protein Binding28%-31% (over the concentration range of 50 to 1000 ng/mL)
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-HT<sub>1A</sub>, 5-HT<sub>5A</sub>, and 5-HT<sub>7</sub> receptors and no significant affinity or pharmacological activity at 5-HT<sub>2</sub>, 5-HT<sub>3</sub> or 5-HT<sub>4</sub> 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-HT<sub>1</sub> receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Naratriptan in humans.
Mechanism 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.
Biological Half-Life5-8 hours
Metabolism/Metabolites
Primarily hepatic. <i>In vitro,</i> naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.
Primarily hepatic. <i>In vitro,</i> naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites. Half Life: 5-8 hours
Related reactions
8 records
Compound notes
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