5-carboxy-2-methylpyrazin-1-ium-1-olate

• ChemBase编号: 70507
• 分子式: C6H6N2O3
• 平均质量: 154.12344
• 单一同位素质量: 154.03784206
• SMILES: c1(cnc(c[n+]1[O-])C(=O)O)C
• Canonical SMILES: [O-][n+]1cc(ncc1C)C(=O)O
• InChI: InChI=1S/C6H6N2O3/c1-4-2-7-5(6(9)10)3-8(4)11/h2-3H,1H3,(H,9,10)
• InChIKey: DJQOOSBJCLSSEY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-carboxy-2-methylpyrazin-1-ium-1-olate
• IUPAC传统名: acipimox; 5-carboxy-2-methylpyrazin-1-ium-1-olate
• 别名: 5-Carboxy-2-methylpyrazine 1-oxide; Acipimox; 5-Methyl-2-pyrazinecarboxylic Acid 4-Oxide; 5-Methylpyrazinecarboxylic Acid 4-Oxide; K 9321; K-9321; Olbemox; Olbetam; Acipimox

登记号

• CAS号: 51037-30-0
• PubChem SID: 162036222
• PubChem CID: 5310993

理论计算性质

• Acid pKa: 3.2699058
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -3.1730733
• LogD (pH = 7.4): -4.3939824
• Log P: -0.96167445
• 摩尔折射率: 37.4361 cm^3
• 极化性: 13.274692 Å^3
• 极化表面积: 75.65 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol; Water
• 外观: Yellow Solid
• 熔点: 179-181°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 生物活性机理: Appears to reduce apoprotein-B-synthesis; Reductor of Apoprotein-B levels; Reductor of plasma VLDL levels; Reported adipose-tissue lipolysis-inhibitor

产品相关信息

• 纯度: 95+%
• 成盐信息: Free Base
• 应用领域: Antihyperlipidaemic agent

详细说明

Selleck Chemicals - S1806

Research Area: Metabolic Disease, Cardiovascular Disease
Biological Activity:
Acipimox is a niacin derivative used as a hypolipidemic agent. It is used in low doses and may have less marked adverse effects, although it is unclear whether the recommended dose is as effective as those standard doses of nicotinic acid. These drugs inhibit hepatic triglyceride production and VLDL secretions, which lead indirectly to a modest reduction in LDL and increase in HDL. Long-term administration is associated with reduced mortality, but unwanted effects limit it’s clinical use. Adverse effects include flushing (associated with Prostaglandin D2), palpitations, and GIT distrubances. Flushing can be reduced by taking aspirin 20-30 min before. High doses can cause disorders of liver function, impair glucose tolerance and precipitate gout. [1]

Toronto Research Chemicals - A189850

Antilipemic.

参考文献

• http://en.wikipedia.org/wiki/Acipimox
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• Boatman, P., et al.: J. Med. Chem., 51, 7653 (1980)
• Rigazio, S., et
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 409A, (nmr)
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• Felder, E. et al., Chem. Ber., 1967, 100, 555, (synth)
• Musatti, L. et al., J. Int. Med. Res., 1981, 9, 381, (pharmacol)
• Aktories, K. et al., Arzneim.-Forsch., 1983, 33, 1525, (activity)
• Orsini, G. et al., Pharmacol. Res. Commun., 1985, 17, 927, (tox)
• Borsotti, G.P. et al., Synthesis, 1990, 207, (synth, pmr, ms)
• Iovel, I. et al., Org. Prep. Proced. Int., 1991, 23, 188, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 983