Acipimox

Base Information

• Chemical Name: Acipimox
• CAS No.: 51037-30-0
• Molecular Formula: C6H6N2O3
• Molecular Weight: 154.125
• Hs Code.: 2942000000
• European Community (EC) Number: 256-928-3
• NSC Number: 759818
• UNII: K9AY9IR2SD
• DSSTox Substance ID: DTXSID2046202
• Nikkaji Number: J10.290C
• Wikipedia: Acipimox
• Wikidata: Q2342544
• NCI Thesaurus Code: C72982
• Pharos Ligand ID: WSDMUZKL64Z3
• Metabolomics Workbench ID: 152113
• ChEMBL ID: CHEMBL345714
• Mol file: 51037-30-0.mol

Synonyms:5-methylpyrazine-2-carboxylic acid 4-oxide;5-methylpyrazinecarboxylic acid 4-oxide;acipimox;Nedios;Olbemox;Olbetam

Chemical Property of Acipimox

Chemical Property:

• Appearance/Colour: low yellow liquid or crystalline
• Vapor Pressure: 1.88E-12mmHg at 25°C
• Melting Point: 177-180 °C
• Refractive Index: 1.608
• Boiling Point: 539 °C at 760 mmHg
• PKA: 2.80±0.10(Predicted)
• Flash Point: 279.8 °C
• PSA: 75.65000
• Density: 1.44 g/cm³
• LogP: 0.51670
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol, water (100 mM), DMSO (100 mM), ethanol (<1 mg/ml at 25° C), and 1 M NH4OH (1 mg/ml).
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 154.03784206
• Heavy Atom Count: 11
• Complexity: 162

Purity/Quality:

99.0%min. ^*data from raw suppliers

5-Methylpyrazine-2-carboxylic acid 4-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C=[N+]1[O-])C(=O)O
• Recent ClinicalTrials: The Impact of Free Fatty Acid Reduction on Vascular Function in the Metabolic Syndrome
• Recent EU Clinical Trials: Randomised, double-blinded, placebo-controlled, adaptive design trial of the efficacy of acipimox in patients with Mitochondrial Myopathy
• Description: Acipimox is a nicotinic acid derivate that structurally related to nicotinic acid. Like nicotinic acid, lowers lipids effectively, but unlike nicotinic acid, acipimox is longer acting and therefore much less prone to produce free fatty acid rebounding. It is usually employed in man in the therapy of hypertriglyceridemia. In addition to its lipid lowering activity, it produces a beneficial elevation of the anti-atherogenic high density lipoprotein subfraction, HDL2. Acipimox is recommended as a lipid-lowering agent to treat hyperlipidemia in patients with noninsulin dependent diabetes mellitus.
• Uses: Acipimox is a long-acting antilipemic agent and used for the treatment of hyperlipoproteinemias, in particular hypertriglyceridemias, and as adjunctive therapy for affecting cholesterol metabolism.
• Clinical Use: Acipimox was introduced in Europe to treat hyperlipidemia in 1985. Acipimox is a weak agonist of GPR109A with micromolar binding and functional activity.Like niacin, acipimox raises HDL-C and triggers vasodilation in humans.However, it remains unclear whether acipimox causes mild hyperglycemia as is observed with niacin.
• Drug interactions: Potentially hazardous interactions with other drugs. It can be combined with powerful hypolipidemic drugs such as fenofibrate and lovastatin to enhance the efficacy and reduce the dose and side effects of the drug. Acyclolimus can improve the efficacy of hypoglycemic drugs, so it is necessary to reduce the dose of hypoglycemic drugs and adjust the dose according to the patient's blood sugar. In antioxidant therapy, it can be used in combination with probucol.

Technology Process of Acipimox

There total 10 articles about Acipimox 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: 98.5%

2-methylpyrazin-5-carboxylic acid (5521-55-1) → acipimox (51037-30-0)

Guidance literature:

2-methylpyrazin-5-carboxylic acid; With hydrogenchloride; In water; for 0.5h;

With peracetic acid; In water; at 20 ℃; for 3h; Reagent/catalyst; Temperature;

Reference yield: 92.0%

5-methyl-pyrazine-2,3-dicarboxylic acid (5521-60-8) → acipimox (51037-30-0)

Guidance literature:

5-methyl-pyrazine-2,3-dicarboxylic acid; With sulfuric acid; at 60 ℃; for 1h;

With sodium tungstate (VI) dihydrate; dihydrogen peroxide; In water; for 8h; Reagent/catalyst; Temperature;

Reference yield:

2-methylquinoxaline (7251-61-8) → acipimox (51037-30-0)

Guidance literature:

2-methylquinoxaline; With potassium permanganate; In water; at 80 - 105.5 ℃; for 0.75h;

With sulfuric acid; In water; at 80 - 110 ℃; for 1h;

With potassium tungstate; dihydrogen peroxide; In water; at 45 - 70 ℃; for 3h;

upstream raw materials:

5-methyl-pyrazin-2-carboxamide-4-oxide

5‐methylpyrazine-2-carboxamide

2-methylpyrazin-5-carboxylic acid

dihydrogen peroxide

Downstream raw materials:

5-Methyl-4-oxy-pyrazine-2-carboxylic acid 2,2-dimethyl-6-[4-(4-phenyl-butyl)-phenoxy]-hexyl ester

2-methoxymethyl-5-methylpyrazine-4-oxide

Refernces

• 1、 -. "1-2 - di (4 - pyridyl) ethane - acyclomox eutectic". Paragraph 0060-0061. . Retrieved 2021/10/13.
• 2、 -. "4,4'-dipyridylmethylpyrazine derivative eutectic crystal". Paragraph 0065-0078. . Retrieved 2020/09/09.