212069-94-8

Basic information

• Product Name: SuMatriptan N-Oxide
• Synonyms: SuMatriptan N-Oxide;3-[2-(DiMethyloxidoaMino)ethyl]-N-Methyl-1H-indole-5-MethanesulfonaMide;GR 112504;SuMatriptan Succinate IMpurity – D (EP/BP);SuMatriptan EP IMpurity D;N,N-Dimethyl-2-[5-[(methylsulphamoyl)methyl]-1H-indol-3-yl] ethanamine N-oxide
• CAS NO: 212069-94-8
• Molecular Formula: C14H20N3O3S
• Molecular Weight: 310.3919
• Product Categories: Amines;Aromatics;Heteroycles;Impurities;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 212069-94-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 190-193 °C(Solv: acetone (67-64-1))
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Very Slightly, Heated), Methanol (Very Slightly, Heated), Water (Slightly)
• PKA: 11.28±0.40(Predicted)
• Stability: Hygroscopic, Unstable in DMSO
• CAS DataBase Reference: SuMatriptan N-Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: SuMatriptan N-Oxide(212069-94-8)
• EPA Substance Registry System: SuMatriptan N-Oxide(212069-94-8)

Safety Data

• Hazardous Substances Data: 212069-94-8(Hazardous Substances Data)

Usage

Description

SuMatriptan N-Oxide, also known as Sumatriptan EP Impurity D, is a degradation product of the antimigraine drug Sumatriptan (S810000). It is formed as a result of the breakdown of the original drug, which is commonly used to treat migraine headaches.

Uses

Used in Pharmaceutical Industry:
SuMatriptan N-Oxide is used as a degradation product for the antimigraine drug Sumatriptan (S810000). Its presence is significant in the pharmaceutical industry as it helps in understanding the stability and shelf life of the original drug, Sumatriptan. This knowledge aids in ensuring the safety and efficacy of the medication for patients suffering from migraines.

Upstream product

• 103628-46-2 sumatripan 

Relevant articles and documents

Identification and characterization of stress degradation products of sumatriptan succinate by using LC/Q-TOF-ESI-MS/MS and NMR: Toxicity evaluation of degradation products

Sumatriptan succinate, a selective 5-HT1B receptor agonist, was subjected to forced degradation studies as per to International Conference on Harmonization-specified conditions. The drug exclusively showed its degradation under basic, photolytic, and oxidative stress conditions, whereas it was found to be stable under acidic, thermal, and neutral conditions. Eight (DP-1 to DP-8) degradation products were identified and characterized by UPLC-ESI/MS/MS experiments combined with accurate mass measurements. The effective chromatographic separation was achieved on Hibar Purospher STAR, C18 (250?×?4.6?mm, 5?μm) column using mobile phase consisting of 0.1% formic acid and methanol at a flow rate of 0.6?mL/minute in gradient elution method. It is noteworthy that 2 major degradation products DP-3 and DP-7 were isolated using preparative HPLC and characterized by advanced NMR experiments. The degradation pathway of the sumatriptan was established, which was duly justified by mechanistic explanation. In vitro cytotoxicity of isolated DPs was tested on normal human cells such as HEK 293 (embryonic kidney cells) and RWPE-1 (normal prostate epithelial cells). This study revealed that they were nontoxic up to 100?μm concentration. Further, in silico toxicity of the drug and its degradation products was determined using ProTox-II prediction tool. This study revealed that DP-4 and DP-8 are predicted for immune toxicity. Amine oxidase A and prostaglandin G/H synthase 1 are predicted as toxicity targets for DP-3, DP-4, and DP-6 whereas DP-1 and DP-2 are predicted for amine oxidase A target.