3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]-
nicorandil
CAS: 65141-46-0
Molecular Formula: C8H9N3O4
3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]- - Names and Identifiers
3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]- - Physico-chemical Properties
| Molecular Formula | C8H9N3O4 |
| Molar Mass | 211.17 |
| Density | 1.4271 (rough estimate) |
| Melting Point | 92°C |
| Boling Point | 350.85°C (rough estimate) |
| Flash Point | 230°C |
| Solubility | DMSO: >10 mg/mL. Soluble in methanol, ethanol, acetone or glacial acetic acid, slightly soluble in chloroform or water, almost insoluble in ether or benzene. |
| Vapor Presure | 1.58E-08mmHg at 25°C |
| Appearance | White to white-like crystalline powder |
| Color | white to off-white |
| Merck | 14,6521 |
| Storage Condition | 2-8°C |
| Refractive Index | 1.7400 (estimate) |
| MDL | MFCD00186520 |
| Physical and Chemical Properties | White crystalline powder, odorless or slightly odorous, bitter. Soluble in methanol, ethanol, acetone or acetic acid, slightly soluble in chloroform or water, a few do not dissolve in ether or benzene. Melting point 88.5-93.5 °c. Acute toxicity LD50 rats (mg/kg):1200-1300 oral, 800-1000 intravenous. |
| Use | For the prevention of coronary heart disease, angina pectoris |
| In vitro study | Nicorandil (100 mM) increased flavoprotein oxidation, but did not affect membrane current, restoring mitoK(ATP) and surfaceK(ATP) channels at concentrations higher than 10-fold. Nicorandil reduces cell death in an ischemic granulation model, a cardioprotective effect that is blocked by the mitoK(ATP) channel blocker 5-hydroxydecanoic acid but not by surfaceK(ATP). Effect of channel blocker HMR1098. Nicorandil (100 mM) inhibits the loss of TUNEL positivity, cytochrome C translocation, caspase-3 activation, and mitochondrial membrane potential (Delta(Psi)(m)). Analysis of cells stained with fluorescence Delta(Psi)(m)-indicator, tetramethylrhodamine ethyl ester (TMRE) by fluorescence activated cell sorter showed that, nicorandil prevents Delta(Psi)(m) depolarization in a concentration-dependent manner (EC(50) approximately 40 mM, saturation 100 mM). In both transfected cells, Nicorandil activated a weakly inwardly rectifying, glibenclamide-sensitive 80 pS K channel. In HEK293T cells, Nicorandil preferentially activates the K(ATP) channel containing SUR2B. Nicorandil (100 mM) significantly inhibited the number of cells in TUNEL-positive nuclei and increased 20 mM h2o2-induced caspase-3 activity. Nicorandil concentration-dependently prevents the loss of DeltaPsim induced by H2O2. |
| In vivo study | Nicorandil (2.5 mg/kg daily, p.o.) in combination with Amlodipine (5.0 mg/kg daily, p.o.) three days of action significantly prevented changes and restored enzyme activity to levels close to those of normal rats. |
3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]- - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R41 - Risk of serious damage to eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. |
| WGK Germany | 3 |
| RTECS | US4667600 |
| HS Code | 29333990 |
| Toxicity | LD50 in rats (mg/kg): 1200-1300 orally; 800-1000 i.v. (Nagano) |
3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]- - Reference
| Reference Show more | 1. Zhang, Jianqiang, Chunjuan Huang, and Renjie Xu. "Solubility Determination and Mathematical Modeling of Nicorandil in Several Aqueous Cosolvent Systems at Temperature Ranges of 278.15–323.15 K." Journal of Chemical & Engineering Data 65.8 (2020): 4063-4070 2. Xu, Kexin, et al. "Glibenclamide Targets Sulfonylurea Receptor 1 to Inhibit p70S6K Activity and Upregulate KLF4 Expression to Suppress Non-Small Cell Lung Carcinoma." Molecular cancer therapeutics 18.11 (2019): 2085-2096. |
3-Pyridinecarboxamide, N-[2-(nitrooxy)ethyl]- - Reference Information
| biological activity | Nicorandil (SG-75) is a potastium channel activator, and ornithine cyclase is activated to increase the formation of cyclic ornithine. |
| Target | Value |
| Use | anti-anginal agent. Selective expansion of coronary artery, continuous increase in coronary flow, inhibition of coronary spasm. For various angina pectoris. for the prevention of coronary heart disease and angina pectoris |
| production method | 1.6g of ethyl ammonium nitrate is dissolved in aqueous Tetrahydrofuran, and after adding 3g of potassium carbonate solution in water, 3g of nicotinoyl chloride hydrochloride are then added at 0-5 °c. After completion of the reaction, the tetrahydrofuran layer was separated, treated and concentrated, and then nitric acid was added to obtain 1.5g of nicorandil nitrate. Or nicotinyl chloride hydrochloride and amino ethyl nitrate, in Pyridine at 5 deg C reaction, nicorandil. Methyl nicotinate or its acid chloride first reacts with aminoethanol, and then forms an ester with concentrated nitric acid at 0~5 ° C., and nicorandil nitrate can be obtained. |
Last Update：2024-04-09 15:16:52
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