Niacin Nicotinic Acid

Nicotinic acid (niacin, 2-yridine-3-carboxylic acid) [59-67-6] M 123.1, m 232-234 , pKj 2.00, pK2 4.82. Crystd from benzene. 

Nicotinic acid (niacin) Liver, lean meats, cereals, legumes Energy metabolism... 

Oxidation of nicotine with chromic acid led to the isolation of pyridine-3-carboxylic acid, which was given the trivial name nicotinic acid. We now find that nicotinic acid derivatives, especially nicotinamide, are biochemically important. Nicotinic acid (niacin) is termed vitamin B3, though nicotinamide is also included under the umbrella term vitamin B3 and is the preferred material for dietary supplements. It is common practice to enrich many foodstuffs, including bread, flour, corn, and rice products. Deficiency in nicotinamide leads to pellagra, which manifests itself in diarrhoea, dermatitis, and dementia. 

Pharmacology Niacinamide is synonymous with nicotinamide, 3-pyridine carboxamide, and nicotinic acid amide. Niacinamide is the amide of nicotinic acid (niacin, vitamin B3). Although nicotinic acid and nicotinamide function identically as vitamins, their pharmacologic effects differ. Nicotinamide does not have the hypolipidemic or vasodilating effects characteristic of niacin (nicotinic acid). 

Nicotinic acid (niacin) Yes Reduces LDL Reduces VLDL Raises HDL IV Ik with fibrates severe IV with fibrates Cutaneous flush, GI distress, liver dysfunction, hyperglycemia, hyperuricemia... 

Nicotinic acid (niacin) Nicotinamide adenine dinucleotide Dehydrogenation of proteins in cellular respiration... 

N. americanus—Necator americanus N. gonorrhoeae—Neisseria gonorrhoeae NA—nicotinic acid (niacin)... 

Two vitamins, nicotinamide and pyridoxine (vitamin B6), are pyridine derivatives. Nicotinamide participates in two coenzymes, coenzyme I (65 R = H) which is known variously as nicotinamide adenine dinucleotide (NAD) or diphosphopyridine nucleotide (DPN), and coenzyme II (65 R = P03H2) also called triphosphopyridine nucleotide (TPN) or nicotinamide adenine dinucleotide phosphate (NADP). These are involved in many oxidation-reduction processes, the quaternized pyridine system acting as a hydrogen acceptor and hydrogen donor. Deficiency of nicotinamide causes pellagra, a disease associated with an inadequately supplemented maize diet. Nicotinic acid (niacin) and its amide are... 

The beneficial and adverse effects of nicotinic acid (niacin) have been reviewed (12). Standard nicotinic acid from an immediate-release formulation is metabolized primarily by conjugation, which results in a high frequency of flushing. Long-acting nicotinic acid is metabolized through the nicotinamide pathway, which results in less flushing but increases the risk of hepatotoxicity. Modified-release nicotinic acid, on the other hand, has a more balanced metabolism and causes fewer of both types of adverse effects. 

Callanan D, Blodi BA, Martin DF. J Macular edema with nicotinic acid (niacin). J Am Med Assoc 1998 279 1702. 

Carlson LA. Niaspan, the prolonged release preparation of nicotinic acid (niacin), the broad-spectrum lipid drug. IntJ Clin Pract. 2004 58 706-713. 

The fat-soluble vitamins are A, D, E, and K. The water-soluble vitamins are thiamine (vitamin Bj), riboflavin, nicotinic acid (niacin) and nicotinamide, pyridoxine (vitamin B6), pantothenic acid, biotin, para-aminobenzoic acid, choline, inositol, and other lipotropic agents, ascorbic acid (vitamin C), the riboflavonoids, folate, and vitamin B12 (see Figure 66.1 and Figure 66.2, and Table 66.1). 

There are exceptions to the above. Most or all vitamins can be synthesized chemically. Vitamin D can be synthesized in the skin of animals by exposure to ultraviolet irradiation, and nicotinic acid (niacin) can be synthesized in the body from the AA tryptophan. 

Prior to 1987, the lipid-lowering armamentarium was limited essentially to dietary changes (reductions in saturated fats and cholesterol), the bile acid sequestrants (cholestyramine and colestipol), nicotinic acid (niacin), the fibrates, and probucol. Unfortunately, all of these treatments have limited efficacy or tolerability or both. Substantial reductions in LDL cholesterol (up to 47%) accompanied by increases in HDL cholesterol of up to 32% could be achieved by the combination of a lipid-lowering diet, a bile acid sequestrant, and the subsequent addition of nicotinic acid (Illingworth et al., 1981). However, this therapy is not easy to administer or tolerate and was therefore often unsuc-... 

NAD A Coenzyme Nicotinamide adenine dinucleotide (NAD) is one of the principal oxidation-reduction reagents in biological systems. This nucleotide has the structure of two D-ribose rings (a dmucleotide) linked by their 5 phosphates. The aglycone of one ribose is nicotinamide, and the aglycone of the other is adenine. A dietary deficiency of nicotinic acid (niacin) leads to the disease called pellagra, caused by the inability to synthesize enough nicotinamide adenine dinucleotide. 

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