Nicotinamide
Encyclopedia
Nicotinamide, also known as niacinamide and nicotinic acid amide, is the amide
of nicotinic acid (vitamin B3 / niacin). Nicotinamide is a water-soluble vitamin
and is part of the vitamin B
group. Nicotinic acid, also known as niacin
, is converted to nicotinamide in vivo
, and, though the two are identical in their vitamin functions, nicotinamide does not have the same pharmacologic and toxic effects of niacin
, which occur incidental to niacin's conversion. Thus nicotinamide does not reduce cholesterol or cause flushing, although nicotinamide may be toxic to the liver at doses exceeding 3 g/day for adults. In cells, niacin is incorporated into nicotinamide adenine dinucleotide
(NAD) and nicotinamide adenine dinucleotide phosphate
(NADP), although the pathways for nicotinamide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction
reactions.
, and the compound can suppress antigen-induced, lymphocytic transformation and inhibit 3'-5' cyclic AMP phosphodiesterase. Nicotinamide has demonstrated the ability to block the inflammatory actions of iodides known to precipitate or exacerbate inflammatory acne.
Nicomide
is the name of an acne medication and, in its vitamin supplement form, the most predominant ingredient is 750 mg of nicotinamide, based on this area of research. Also, it is used topically as a 4% or 5% gel or cream - as effective as topical 1% clindamycin (8-week double-blind trial) performed at the New York University College of Medicine. Nicotinamide acne treatment is also available as Nicotinamide pads and cream.
Animal studies show that nicotinamide has anti-anxiety (anxiolytic
) properties. It may work in a way similar to benzodiazepines.
Nicotinamide lacks the vasodilator, gastrointestinal, hepatic, and hypolipidemic actions of nicotinic acid. As such, nicotinamide has not been shown to produce the flushing, itching, and burning sensations of the skin as is commonly seen when large doses of nicotinic acid are administered orally. High-dose nicotinamide should still, however, be considered as a drug with toxic potential at adult doses in excess of 3 gm/day and unsupervised use should be discouraged. In overall, it rarely causes side effects, and is considered generally safe as a food additive, and as a component in cosmetics and medication.
Nicotinamide is produced by the aqueous aminolysis
of 3-cyanopyridine (nicotinonitrile) and subsequent crystallization.
Nicotinamide is an activator of sirtuins (but inhibits at higher doses) and has been reported to restore cognition in Alzheimer's disease
transgenic mice. A safety study of niacinamide for the treatment of Alzheimer's disease is currently underway at the University of California, Irvine.
Nicotinamide has been reported to increase the endurance of mice.
Nicotinamide prevents immunosuppression
caused by UVA and UVB radiation, and could be added to sunscreen.
Nicotinamide has been reported to be an effective skin whitener in topical application.
Niacinamide acts as a chemo- and radio-sensitizing agent by enhancing tumor blood flow, thereby reducing tumor hypoxia. Niacinamide also inhibits poly(ADP-ribose) polymerases (PARP-1), enzymes involved in the rejoining of DNA strand breaks induced by radiation or chemotherapy. PARP-1 appears to be an important target for triple negative breast cancers because the cells are sensitive to inhibition of PARP-1. Niacinamide is also used by some patients in combination with intravenous vitamin C therapy for cancer.
Amide
In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
of nicotinic acid (vitamin B3 / niacin). Nicotinamide is a water-soluble vitamin
Vitamin
A vitamin is an organic compound required as a nutrient in tiny amounts by an organism. In other words, an organic chemical compound is called a vitamin when it cannot be synthesized in sufficient quantities by an organism, and must be obtained from the diet. Thus, the term is conditional both on...
and is part of the vitamin B
B vitamins
B vitamins are a group of water-soluble vitamins that play important roles in cell metabolism. The B vitamins were once thought to be a single vitamin, referred to as vitamin B . Later research showed that they are chemically distinct vitamins that often coexist in the same foods...
group. Nicotinic acid, also known as niacin
Niacin
"Niacin" redirects here. For the neo-fusion band, see Niacin .Niacin is an organic compound with the formula and, depending on the definition used, one of the forty to eighty essential human nutrients.Niacin is one of five vitamins associated with a pandemic deficiency disease: niacin deficiency...
, is converted to nicotinamide in vivo
In vivo
In vivo is experimentation using a whole, living organism as opposed to a partial or dead organism, or an in vitro controlled environment. Animal testing and clinical trials are two forms of in vivo research...
, and, though the two are identical in their vitamin functions, nicotinamide does not have the same pharmacologic and toxic effects of niacin
Niacin
"Niacin" redirects here. For the neo-fusion band, see Niacin .Niacin is an organic compound with the formula and, depending on the definition used, one of the forty to eighty essential human nutrients.Niacin is one of five vitamins associated with a pandemic deficiency disease: niacin deficiency...
, which occur incidental to niacin's conversion. Thus nicotinamide does not reduce cholesterol or cause flushing, although nicotinamide may be toxic to the liver at doses exceeding 3 g/day for adults. In cells, niacin is incorporated into nicotinamide adenine dinucleotide
Nicotinamide adenine dinucleotide
Nicotinamide adenine dinucleotide, abbreviated NAD, is a coenzyme found in all living cells. The compound is a dinucleotide, since it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine base and the other nicotinamide.In metabolism, NAD is involved...
(NAD) and nicotinamide adenine dinucleotide phosphate
Nicotinamide adenine dinucleotide phosphate
Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or TPN in older notation , is a coenzyme used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent....
(NADP), although the pathways for nicotinamide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
reactions.
Use in medicine
Nicotinamide has demonstrated anti-inflammatory actions that may be of benefit to patients with inflammatory skin conditions. These conditions include acne vulgarisAcne vulgaris
Acne vulgaris is a common human skin disease, characterized by areas of skin with seborrhea , comedones , papules , pustules , Nodules and possibly scarring...
, and the compound can suppress antigen-induced, lymphocytic transformation and inhibit 3'-5' cyclic AMP phosphodiesterase. Nicotinamide has demonstrated the ability to block the inflammatory actions of iodides known to precipitate or exacerbate inflammatory acne.
Nicomide
Nicomide
Nicomide is an acne medication available in topical cream, topical gel and vitamin supplement form . Tablets available by prescription only and contain the active ingredients nicotinamide, zinc, copper, and folic acid. The topical cream and topical gel are formulated into a 4% nicotinamide mixture...
is the name of an acne medication and, in its vitamin supplement form, the most predominant ingredient is 750 mg of nicotinamide, based on this area of research. Also, it is used topically as a 4% or 5% gel or cream - as effective as topical 1% clindamycin (8-week double-blind trial) performed at the New York University College of Medicine. Nicotinamide acne treatment is also available as Nicotinamide pads and cream.
Animal studies show that nicotinamide has anti-anxiety (anxiolytic
Anxiolytic
An anxiolytic is a drug used for the treatment of anxiety, and its related psychological and physical symptoms...
) properties. It may work in a way similar to benzodiazepines.
Nicotinamide lacks the vasodilator, gastrointestinal, hepatic, and hypolipidemic actions of nicotinic acid. As such, nicotinamide has not been shown to produce the flushing, itching, and burning sensations of the skin as is commonly seen when large doses of nicotinic acid are administered orally. High-dose nicotinamide should still, however, be considered as a drug with toxic potential at adult doses in excess of 3 gm/day and unsupervised use should be discouraged. In overall, it rarely causes side effects, and is considered generally safe as a food additive, and as a component in cosmetics and medication.
Nicotinamide is produced by the aqueous aminolysis
Aminolysis
Aminolysis is any chemical reaction in which a molecule is split into two parts by reacting with a molecule of ammonia or an amine.An example of an aminolysis reaction is the replacement of a halogen in an alkyl group by an amine and the elimination of hydrogen halide .Another common example is...
of 3-cyanopyridine (nicotinonitrile) and subsequent crystallization.
Nicotinamide is an activator of sirtuins (but inhibits at higher doses) and has been reported to restore cognition in Alzheimer's disease
Alzheimer's disease
Alzheimer's disease also known in medical literature as Alzheimer disease is the most common form of dementia. There is no cure for the disease, which worsens as it progresses, and eventually leads to death...
transgenic mice. A safety study of niacinamide for the treatment of Alzheimer's disease is currently underway at the University of California, Irvine.
Nicotinamide has been reported to increase the endurance of mice.
Nicotinamide prevents immunosuppression
Immunosuppression
Immunosuppression involves an act that reduces the activation or efficacy of the immune system. Some portions of the immune system itself have immuno-suppressive effects on other parts of the immune system, and immunosuppression may occur as an adverse reaction to treatment of other...
caused by UVA and UVB radiation, and could be added to sunscreen.
Nicotinamide has been reported to be an effective skin whitener in topical application.
Niacinamide acts as a chemo- and radio-sensitizing agent by enhancing tumor blood flow, thereby reducing tumor hypoxia. Niacinamide also inhibits poly(ADP-ribose) polymerases (PARP-1), enzymes involved in the rejoining of DNA strand breaks induced by radiation or chemotherapy. PARP-1 appears to be an important target for triple negative breast cancers because the cells are sensitive to inhibition of PARP-1. Niacinamide is also used by some patients in combination with intravenous vitamin C therapy for cancer.