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Nicotinamide

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(Redirected fromNiacinamide)
Dietary supplement and medication

Pharmaceutical compound
Nicotinamide
Clinical data
Pronunciation/ˌnaɪəˈsɪnəmaɪd/,/ˌnɪkəˈtɪnəmaɪd/
Other namesNAM, 3-pyridinecarboxamide
niacinamide (USANUS)
nicotinic acid amide
vitamin PP
nicotinic amide
vitamin B3
AHFS/Drugs.comConsumer Drug Information
License data
Routes of
administration		oral,topical
ATC code
Legal status
Legal status
Identifiers
  • pyridine-3-carboxamide
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.002.467Edit this at Wikidata
Chemical and physical data
FormulaC6H6N2O
Molar mass122.127 g·mol−1
3D model (JSmol)
Density1.40 g/cm3 g/cm3[1]
Melting point129.5 °C (265.1 °F)
Boiling point334 °C (633 °F)
  • c1cc(cnc1)C(=O)N
  • InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
  • Key:DFPAKSUCGFBDDF-UHFFFAOYSA-N

Nicotinamide (INN,BANUK[2]) orniacinamide (USANUS) is a form ofvitamin B3 found in food and used as adietary supplement and medication.[3][4][5] As a supplement, it is usedorally (swallowed by mouth) to prevent and treatpellagra (niacin deficiency).[4] Whilenicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causingskin flushing.[4] As a cream, it is used to treatacne, and has been observed in clinical studies to improve the appearance of aging skin by reducinghyperpigmentation and redness.[5][6] It is awater-soluble vitamin.

Side effects are minimal.[7][8] At high doses,liver problems may occur.[7] Normal amounts are safe for use duringpregnancy.[9] Nicotinamide is in thevitamin B family of medications, specifically thevitamin B3 complex.[10][11] It is anamide of nicotinic acid.[7] Foods that contain nicotinamide includeyeast,meat, milk, andgreen vegetables.[12]

Nicotinamide was discovered between 1935 and 1937.[13][14] It is on theWorld Health Organization's List of Essential Medicines.[15][16] Nicotinamide is available as ageneric medication andover the counter.[10] Commercially, nicotinamide is made from eithernicotinic acid (niacin) ornicotinonitrile.[14][17] In some countries,grains have nicotinamide added to them.[14]

Extra-terrestrial nicotinamide has been found incarbonaceous chondrite meteorites.[18]

Medical uses

[edit]

Niacin deficiency

[edit]

Nicotinamide is the preferred treatment forpellagra, caused by niacin deficiency.[4]

Acne

[edit]

Nicotinamidecream is used as a treatment foracne.[5] It has anti-inflammatory actions, which may benefit people with inflammatory skin conditions.[19]

Nicotinamide increases the biosynthesis ofceramides in humankeratinocytes in vitro and improves the epidermal permeability barrier in vivo.[20] The application of 2% topical nicotinamide for 2 and 4 weeks has been found to be effective in lowering thesebum excretion rate.[21] Nicotinamide has been shown to preventCutibacterium acnes-induced activation oftoll-like receptor 2, which ultimately results in the down-regulation of pro-inflammatoryinterleukin-8 production.[22]

Skin cancer

[edit]

Nicotinamide at doses of 500 to 1000 mg a day decreases the risk ofskin cancers, other thanmelanoma, in those at high risk.[23]

Side effects

[edit]

Nicotinamide has minimal side effects.[7][8] At very high doses above 3 g per day acuteliver toxicity has been documented in at least one case.[7] Normal doses are safe duringpregnancy.[9]

Chemistry

[edit]

The structure of nicotinamide consists of apyridine ring to which aprimary amide group is attached in themeta position. It is anamide ofnicotinic acid.[7] As anaromatic compound, it undergoeselectrophilic substitution reactions and transformations of its twofunctional groups. Examples of these reactions reported inOrganic Syntheses include the preparation of2-chloronicotinonitrile by a two-step process via theN-oxide,[24][25]

fromnicotinonitrile by reaction withphosphorus pentoxide,[26] and from3-aminopyridine by reaction with a solution ofsodium hypobromite, preparedin situ frombromine andsodium hydroxide.[27]

NAD+, the oxidized form ofNADH, contains the nicotinamidemoiety (highlighted in red)

Industrial production

[edit]

The hydrolysis ofnicotinonitrile is catalysed by the enzymenitrile hydratase fromRhodococcus rhodochrous J1,[28][29][17] producing 3500 tons per annum of nicotinamide for use in animal feed.[30] The enzyme allows for a more selective synthesis as further hydrolysis of the amide tonicotinic acid is avoided.[31][32] Nicotinamide can also be made from nicotinic acid. According toUllmann's Encyclopedia of Industrial Chemistry, worldwide 31,000 tons of nicotinamide were sold in 2014.[14]

Biochemistry

[edit]
The active Nicotinamide group on the molecule NAD+ undergoes oxidation in many metabolic pathways.

Nicotinamide, as a part of the cofactornicotinamide adenine dinucleotide (NADH / NAD+) is crucial to life. In cells, nicotinamide is incorporated into NAD+ andnicotinamide adenine dinucleotide phosphate (NADP+). NAD+ and NADP+ arecofactors in a wide variety of enzymaticoxidation-reduction reactions, most notablyglycolysis, thecitric acid cycle, and theelectron transport chain.[33] If humans ingest nicotinamide, it will likely undergo a series of reactions that transform it into NAD, which can then undergo a transformation to form NADP+. This method of creation of NAD+ is called asalvage pathway. However, the human body can produce NAD+ from the amino acidtryptophan and niacin without our ingestion of nicotinamide.[34]

NAD+ acts as an electron carrier that mediates the interconversion of energy between nutrients and the cell's energy currency,adenosine triphosphate (ATP). In oxidation-reduction reactions, the active part of the cofactor is the nicotinamide. In NAD+, the nitrogen in the aromatic nicotinamide ring is covalently bonded to adenine dinucleotide. The formal charge on the nitrogen is stabilized by the shared electrons of the other carbon atoms in the aromatic ring. When a hydride atom is added onto NAD+ to form NADH, the molecule loses its aromaticity, and therefore a good amount of stability. This higher energy product later releases its energy with the release of a hydride, and in the case of the electron transport chain, it assists in formingadenosine triphosphate.[35]

When one mole of NADH is oxidized, 158.2 kJ of energy will be released.[35]

Biological role

[edit]

Nicotinamide occurs as a component of a variety of biological systems, including within thevitamin B family and specifically thevitamin B3 complex.[10][11] It is also a critically important part of the structures ofNADH and NAD+, where theN-substituted aromatic ring in the oxidised NAD+ form undergoes reduction with hydride attack to form NADH.[33] TheNADPH/NADP+ structures have the same ring, and are involved in similar biochemical reactions.

Nicotinamide can be methylated in the liver to biologically inactive1-Methylnicotinamide when there are sufficient methyl donors.

Food sources

[edit]

Nicotinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables.[36] It is commonly added to cereals and other foods. Many multivitamins contain 20–30 mg ofvitamin B3 and it is also available in higher doses.[37]

Compendial status

[edit]

Research

[edit]

A 2015 trial found nicotinamide to reduce the rate of new nonmelanoma skin cancers and actinic keratoses in a group of people at high risk for the conditions.[40]

Nicotinamide has been investigated for many additional disorders, including treatment ofbullous pemphigoid and nonmelanoma skin cancers.[41]

Nicotinamide may be beneficial in treating psoriasis.[42]

There is tentative evidence for a potential role of nicotinamide in treating acne, rosacea, autoimmune blistering disorders, ageing skin, and atopic dermatitis.[41] Nicotinamide also inhibits poly(ADP-ribose)polymerases (PARP-1), enzymes involved in the rejoining of DNA strand breaks induced by radiation or chemotherapy.[43] ARCON (accelerated radiotherapy plus carbogen inhalation and nicotinamide) has been studied in cancer.[44]

Research has suggested nicotinamide may play a role in the treatment ofHIV.[45]

Extra-terrestrial occurrence

[edit]

Extra-terrestrial nicotinamide has been found in carbonaceous chondrite meteorites.

Vitamin B3 vitamers from extra-terrestrial sources
MeteoriteNicotinic acidNicotinamide
Orgueil[46]715 ppb214 ppb
Murray[18]626 ppb65 ppb
Murchison2.4 nmol/g[47] 190 ppb[18]16 ppb[18]
Tagish Lake[18]108 ppb5 ppb

References

[edit]
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