2-(pyridin-3-ylformamido)ethyl nitrate

• ChemBase ID: 72829
• Molecular Formular: C8H9N3O4
• Molecular Mass: 211.17476
• Monoisotopic Mass: 211.05930578
• SMILES: c1cncc(c1)C(=O)NCCO[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)OCCNC(=O)c1cccnc1
• InChI: InChI=1S/C8H9N3O4/c12-8(7-2-1-3-9-6-7)10-4-5-15-11(13)14/h1-3,6H,4-5H2,(H,10,12)
• InChIKey: LBHIOVVIQHSOQN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(pyridin-3-ylformamido)ethyl nitrate
• IUPAC Traditional name: 2-(pyridin-3-ylformamido)ethyl nitrate; nicorandil
• Synonyms: N-(2-Nitrooxyethyl)nicotinamide; Adancor; Perisalol; N -[2-(Nitrooxy)ethyl]-3-pyridinecarboxamide; N -(2-Hydroxyethyl)nicotinamide nitrate; Siomart; 2-(Pyridine-3-carbonylamino)ethyl nitrate; 2-Nicotinamidoethyl nitrate; N-[2-(Nitrooxy)ethyl]-3-pyridinecarboxamide; SG-75; Sigmart; Zynicor; Nicorandil; Ikorel; Dancor; Nikoran; Aprior; Nitorubin; Nicorandil

Database IDs

• CAS Number: 65141-46-0
• EC Number: 265-514-1
• MDL Number: MFCD00186520
• PubChem SID: 162037750
• PubChem CID: 47528

CALCULATED PROPERTIES

• Acid pKa: 13.81437
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.059642516
• LogD (pH = 7.4): 0.06467452
• Log P: 0.064739294
• Molar Refractivity: 50.8625 cm^3
• Polarizability: 18.730612 Å^3
• Polar Surface Area: 97.04 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; Ethanol; Ether; Methanol
• Apperance: White solid; white to off-white powder
• Melting Point: 92-93°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: US4667600
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Antioxidant; Guanylate cyclase stimulator; May act as an indirect calcium antagonist; Potassium channel activator; Reported deoxyribose breakdown inhibitor; Reported potassium agonist; Reported vasodilador

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Application(s): Antioxidant; Cardiant; Smooth muscle relaxant
• Empirical Formula (Hill Notation): C8H9N3O4

DETAILS

Selleck Chemicals - S1971

Research Area: Inflammation
Biological Activity:
Nicorandil(Ikorel)is potassium channel activator. It acts by relaxing the smooth muscle of the blood vessels, especially those of the venous system. It does this through two methods. Firstly, by activating potassium channels, and secondly by donating nitric oxide to activate the enzyme guanylate cyclase. Guanylate cyclase causes activation of cGMP leading to both arterial and venous vasodilatation by de-phosphorylation of the myosin light chain. [1]

Sigma Aldrich - N3539

Biochem/physiol Actions
Nicorandil is a hybrid ATP-sensitive K+ (KATP) channel opener and nicotinamide nitrate NO donor. Nicorandil selectively activates SUR2B- versus SUR2A-containing KATP channels. It enhances endothelial NO synthase expression and protects against ischemic ventricular arrhythmias. By activating potassium channels, and donating nitric oxide to activate the enzyme guanylate cyclase, Nicorandil causes activation of GMP leading to both arterial and venous vasodilatation. Nicorandil is selective for vascular potassium channels, but has no significant action on cardiac contractility and conduction.

Toronto Research Chemicals - N398500

An antianginal.

REFERENCES

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