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

• ChemBase ID: 70507
• Molecular Formular: C6H6N2O3
• Molecular Mass: 154.12344
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-carboxy-2-methylpyrazin-1-ium-1-olate
• IUPAC Traditional name: acipimox; 5-carboxy-2-methylpyrazin-1-ium-1-olate
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.2699058
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -3.1730733
• LogD (pH = 7.4): -4.3939824
• Log P: -0.96167445
• Molar Refractivity: 37.4361 cm^3
• Polarizability: 13.274692 Å^3
• Polar Surface Area: 75.65 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 179-181°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: Appears to reduce apoprotein-B-synthesis; Reductor of Apoprotein-B levels; Reductor of plasma VLDL levels; Reported adipose-tissue lipolysis-inhibitor

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Application(s): Antihyperlipidaemic agent

DETAILS

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.

REFERENCES

• http://en.wikipedia.org/wiki/Acipimox
• Fuccella, L.M., et al.: Clin. Pharmacol. Ther., 28, 790 (1980)
• Lovisolo, P.P., et al.: Pharmacol. Res. Commun., 13, 151 (1980)
• Aktories, K., et al.: Arzneim.-Forsch., 33, 1525 (1980)
• 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)
• Pitr, D. et al., Chem. Ber., 1966, 99, 9745
• 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