2-(pyridin-3-ylformamido)ethyl nitrate

• ChemBase编号: 72829
• 分子式: C8H9N3O4
• 平均质量: 211.17476
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-(pyridin-3-ylformamido)ethyl nitrate
• IUPAC传统名: 2-(pyridin-3-ylformamido)ethyl nitrate; nicorandil
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 13.81437
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 0.059642516
• LogD (pH = 7.4): 0.06467452
• Log P: 0.064739294
• 摩尔折射率: 50.8625 cm^3
• 极化性: 18.730612 Å^3
• 极化表面积: 97.04 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: >10 mg/mL; Ethanol; Ether; Methanol
• 外观: White solid; white to off-white powder
• 熔点: 92-93°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: US4667600
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-41
• 安全公开号: 26-39
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H302-H318
• GHS警示性声明: P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: room temp

药理学性质

• 生物活性机理: Antioxidant; Guanylate cyclase stimulator; May act as an indirect calcium antagonist; Potassium channel activator; Reported deoxyribose breakdown inhibitor; Reported potassium agonist; Reported vasodilador

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• 应用领域: Antioxidant; Cardiant; Smooth muscle relaxant
• Empirical Formula (Hill Notation): C8H9N3O4

详细说明

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.

参考文献

• http://en.wikipedia.org/wiki/Nicorandil
• Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2008)
• Sudo, H., et al.: Biol. Pharm. Bull., 31, 2079 (2008)
• Iida, S., et al.: Brit. J. Clin. Pharmacol., 66, 352 (2008)
• Eguchi, Y., et al.: Ther. Res., 29, 316 (2008)
• Ger. Pat., 1977, Chugai Pharm, 2 714 713; CA, 88, 22652, (synth, pharmacol)
• Taira, N. et al., Clin. Exp. Pharmacol. Physiol., 1979, 6, 301, (pharmacol)
• Frydman, A.M. et al., Am. J. Cardiol., 1989, 63, 25J, (pharmacokinet)
• Frampton, J. et al., Drugs, 1992, 44, 625, (rev)
• Purcell, H. et al., Br. J. Clin. Pract., 1993, 47, 150, (rev)
• Kato, K. et al., Eur. Heart J., Suppl. B, 1993, 14, (rev)
• Tanikawa, M. et al., J. Chromatogr., 1993, 617, 163, (hplc)
• Bachert, E.L. et al., J. Chromatogr., 1993, 619, 336, (hplc)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1025
• Matsui, T. et al., Acta Neurochir. (Vienna), 1994, 126, 165, (pharmacol)
• Jaraki, O. et al., J. Cardiovasc. Pharmacol., 1994, 23, 24, (pharmacol)
• Naito, A. et al., Jpn. J. Pharmacol., 1994, 65, 209, (pharmacol)
• Markham, A. et al., Drugs, 2000, 60, 955-974, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NDL800