Nicorandil

Base Information

• Chemical Name: Nicorandil
• CAS No.: 65141-46-0
• Molecular Formula: C8H9N3O4
• Molecular Weight: 211.177
• Hs Code.: 29333990
• European Community (EC) Number: 265-514-1
• UNII: 260456HAM0
• DSSTox Substance ID: DTXSID8045692
• Wikipedia: Nicorandil
• Wikidata: Q862989
• NCI Thesaurus Code: C84012
• Metabolomics Workbench ID: 67756
• ChEMBL ID: CHEMBL284906
• Mol file: 65141-46-0.mol

Synonyms:2 Nicotinamidethyl Nitrate;2 Nicotinamidoethyl Nitrate;2-Nicotinamidethyl Nitrate;2-Nicotinamidoethyl Nitrate;Adancor;Dancor;Ikorel;Nicorandil;Nitrate, 2-Nicotinamidethyl;Nitrate, 2-Nicotinamidoethyl;SG 75;SG-75;SG75

Chemical Property of Nicorandil

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.58E-08mmHg at 25°C
• Melting Point: 92 °C
• Refractive Index: 1.547
• Boiling Point: 456.7 °C at 760 mmHg
• PKA: pKa 空 (Uncertain)
• Flash Point: 230 °C
• PSA: 97.04000
• Density: 1.331 g/cm³
• LogP: 0.93380
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 211.05930578
• Heavy Atom Count: 15
• Complexity: 228

Purity/Quality:

99% ^*data from raw suppliers

Nicorandil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CN=C1)C(=O)NCCO[N+](=O)[O-]
• Recent ClinicalTrials: A Study to Evaluate the Impact of Pre-procedural Intracoronary Nicorandil Injection to PREVENT reductioN Of decREased TIMI FLOW in Patients Who Undergoing Percutaneous Coronary Intervention for the Coronary Artery Disease
• Recent EU Clinical Trials: The bioavailability of nicorandil in humans: A pilot study to investigate the variability of its pharmacokinetic parameters in healthy volunteers.
• Recent NIPH Clinical Trials: The Utility of Exercise-induced Hyperemia for the Measurement of Fractional Flow Reserve in Patients With Intermediate Coronary Stenosis
• Uses: Nicorandil is a vasodilator used for the prophylaxis and treatment of angina. This medication widens blood vessels thus increasing the blood and oxygen flow to the heart. It is not currently available in the US.Nicorandil is a nitric oxide donor and ATP-sensitive potassium channel opener. A study showed that Nicorandil is able to protect against stress-induced cell death in dystrophin-deficient cardiomyocytes and also preserve cardiac function in the mdx mouse heart subjected to ischemia and reperfusion injury.
• Clinical Use: Nicorandil is used for the prevention and treatment of chronic stable angina. It is usually used when angina becomes difficult to control by other drugs and is given as an additional treatment.
• Drug interactions: Potentially hazardous interactions with other drugs Avanafil, sildenafil, tadalafil and vardenafil: enhanced hypotensive effect - avoid. Riociguat: possible enhanced hypotensive effect - avoid.

Technology Process of Nicorandil

There total 9 articles about Nicorandil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

N-(2-hydroxyethyl)nicotinamide (6265-73-2) → N-(2-nitroxyethyl)nicotinamide (65141-46-0)

Guidance literature:

With nitric acid; urea; europium(III) trifluoromethanesulfonate; at 70 ℃; for 6h; Schlenk technique;

DOI:10.1039/d0ob01519a

Reference yield: 80.0%

2-(pyridin-3-yl)-4,5-dihydrooxazole (40055-37-6) + isopentyl nitrite (110-46-3) → N-(2-nitroxyethyl)nicotinamide (65141-46-0)

Guidance literature:

In 1,4-dioxane; at 100 ℃; for 5h;

Reference yield: 73.0%

2-(pyridin-3-yl)-4,5-dihydrooxazole (40055-37-6) → N-(2-nitroxyethyl)nicotinamide (65141-46-0)

Guidance literature:

With tert.-butylnitrite; oxygen; In 1,4-dioxane; at 60 ℃; Sealed tube; Green chemistry;

DOI:10.1039/c7gc02682j

upstream raw materials:

pyridine-3-carbonyl chloride hydrochloride

2-nitroxyethylammonium nitrate

N-(2-hydroxyethyl)nicotinamide

3-pyridinecarboxylic acid ethyl ester

Downstream raw materials:

nicorandil hydrochloride

2-(pyridin-3-yl)-4,5-dihydrooxazole

Refernces

• 1、 An, Jichao,He, Pan,Li, Wenhao,Liu, Peipei,Si, Mengyuan,Yang, Bo,Yang, Guanyu. "Practical catalytic nitration directly with commercial nitric acid for the preparation of aliphatic nitroesters". supporting information. p. 6612 - 6616. Retrieved 2020/09/21.
• 2、 -. "Nicorandil preparation method". . . Retrieved 2020/04/06.