Basic information
- CAS
143388-64-1- Standard SMILES
CNS(=O)(=O)CCc1ccc2[nH]cc(C3CCN(C)CC3)c2c1.Cl- InChIKey
AWEZYKMQFAUBTD-UHFFFAOYSA-N- Molecular formula
- C17H26ClN3O2S
- Average molar mass
- 371.9 g/mol
- Monoisotopic mass
- 371.1434259
Overview
Naratriptan Hydrochloride is the hydrochloride salt form of naratriptan, a sulfonamide with selective serotonin (5-HT) 1 receptor agonistic activity and anti-migraine property. Naratriptan hydrochloride binds selectively and with high affinity to the 5-HT1D and 5-HT1B receptor subtypes. Activation of these 5-HT1D/B receptors located on intracranial blood vessels leads to vasoconstriction and provides relief of migraine headaches. Naratriptan hydrochloride may also exerts its effect by stimulation of 5-HT1D/1B receptors on sensory nerve endings in the trigeminal system thereby decreasing the release of pro-inflammatory neuropeptides.
Names & identifiers
- Preferred name
- Naratriptan Hydrochloride
- IUPAC
- N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide;hydrochloride
- English name
- Naratriptan Hydrochloride
- Molecular formula
- C17H25N3O2S.ClH
- Molecular weight
- 371.93
Names & synonyms
NARATRIPTAN HYDROCHLORIDE143388-64-1Naratriptan HClGR-85548AGR 85548ADTXSID604906410X8X4P12ZN-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide monohydrochlorideDTXCID10289901H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, monohydrochlorideCHEBI:7479RefChem:57989
Show more names
NaramigAmerge.Nariptan HydrochlorideGR-85548A hydrochlorideNaratriptan Nitrate USPNaratryptan hydrochlorideNaratriptan monohydrochlorideNaratriptan HCl (GR-85548A HCl)
1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1)N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide Monohydrochloride662-728-0AmergeNaratriptan (hydrochloride)MFCD08141821s1488N-Methyl-2-(3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)ethane-1-sulfonamide hydrochloride
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 73.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 483
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 234 · 234-236°C
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- 2 O: · H2O: ≥10mg/mL
- form
- powder
- color
- white to off-white
- Water Solubility
- 2 O: · H2O: ≥10mg/mL
- InChI
- 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
- InChIKey
- AWEZYKMQFAUBTD-UHFFFAOYSA-N
- SMILES
- Cl.CNS(=O)(=O)CCc1ccc2[nH]cc(C3CCN(C)CC3)c2c1
- FDA UNII
- 10 X8X4P12Z · 10X8X4P12Z
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (95.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesEye Irrit. 2 (95.7%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Naratriptan hydrochloride
Ambiguous-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- hs_code
- 2935904000
- risk_code
- 36
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs used to cause constriction of the blood vessels.
Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes.
Applications
DescriptionNaramig was launched in Germany, Sweden and the UK for use in migraine. It is chemically available via a number of related synthetic routes all having about three steps starting from 5-bromoindole. It is a new serotonin 5-HT1B/1D receptor antagonist with modest affinity for 5-HT1a, and very weak affinity for 5-HT3 receptors. It has little or no affinity for a wide range of non-serotonin receptors including a- and padrenoceptors, dopamine, neurokinin NK1, and opiate receptors. It mediates vasoconstriction in cerebral vasculature (extra cerebral intracranial vessels), reduces neurogenic inflammation, and inhibits responses mediated by the trigeminal nerves. It has a 6- and 3-fold greater affinity for 5-HT1B, and 5-HT1D, receptors, respectively, than sumatriptan which translates to a 2-3 fold increase in potency. The reoccurance of headache was less compared to sumatriptan, zolmitriptan and rizatriptan. Naramig had no clinical effects on blood pressure or heart rate, had a long duration of action with very good tolerability, and has high oral bioavailability.
UsesNaratriptan Hydrochloride is a triptan drug that is used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist
UsesNaratriptan Hydrochloride is a triptan drug and is used for the treatment of migraine headaches
Useslaxative
Upstream & downstream products
Upstream raw materials
Related reactions
11 records
Compound notes
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