Nicotinamide

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Nicotinamide
Clinical data
Pronunciation/ˌnaɪəˈsɪnəmaɪd/, /ˌnɪkəˈtɪnəmaɪd/
Other namesNAM, 3-pyridinecarboxamide
niacinamide
nicotinic acid amide
vitamin PP
nicotinic amide
vitamin B3
AHFS/Drugs.comConsumer Drug Information
License data
topical
ATC code
Legal status
Legal status
Identifiers
  • pyridine-3-carboxamide
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

Niacinamide or nicotinamide is a form of

water-soluble vitamin
. Niacinamide is the supplement name, while nicotinamide is the scientific name.

Side effects are minimal.

green vegetables.[11]

Niacinamide was discovered between 1935 and 1937.

grains have niacinamide added to them.[13]

Medical uses

Niacin deficiency

Niacinamide is the preferred treatment for pellagra, caused by niacin deficiency.[3]

Acne

Niacinamide

cream is used as a treatment for acne.[4] It has anti-inflammatory actions, which may benefit people with inflammatory skin conditions.[17]

Niacinamide increases the biosynthesis of

toll-like receptor 2, which ultimately results in the down-regulation of pro-inflammatory interleukin-8 production.[20]

Skin cancer

Niacinamide at doses of 500 to 1000 mg a day decreases the risk of skin cancers, other than melanoma, in those at high risk.[21]

Side effects

Niacinamide has minimal side effects.

liver toxicity has been documented in at least one case.[6] Normal doses are safe during pregnancy.[8]

Chemistry

The structure of nicotinamide consists of a

N-oxide,[22][23]

from

3-aminopyridine by reaction with a solution of sodium hypobromite, prepared in situ from bromine and sodium hydroxide.[25]

NAD+, the oxidized form of NADH, contains the nicotinamide moiety (highlighted in red)

Industrial production

The hydrolysis of

nicotinic acid is avoided.[29][30] Nicotinamide can also be made from nicotinic acid. According to Ullmann's Encyclopedia of Industrial Chemistry, worldwide 31,000 tons of nicotinamide were sold in 2014.[13]

Biochemistry

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

Nicotinamide, as a part of the cofactor

salvage pathway. However, the human body can produce NAD+ from the amino acid tryptophan and niacin without our ingestion of nicotinamide.[32]

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 forming adenosine triphosphate.[33]

When one mole of NADH is oxidized, 158.2 kJ of energy will be released.[33]

Biological role

Nicotinamide occurs as a component of a variety of biological systems, including within the

vitamin B3 complex.[9][10] It is also a critically important part of the structures of NADH and NAD+, where the N-substituted aromatic ring in the oxidised NAD+ form undergoes reduction with hydride attack to form NADH.[31] The NADPH/NADP+
structures have the same ring, and are involved in similar biochemical reactions.

Nicotinamide can be methylated in the liver to biologically active 1-Methylnicotinamide when there are sufficient methyl donors.

Food sources

Niacinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables.[34] It is commonly added to cereals and other foods. Many multivitamins contain 20–30 mg of vitamin B3 and it is also available in higher doses.[35]

Compendial status

Research

A 2015 trial found niacinamide to reduce the rate of new nonmelanoma skin cancers and actinic keratoses in a group of people at high risk for the conditions.[38]

Niacinamide has been investigated for many additional disorders, including treatment of bullous pemphigoid nonmelanoma skin cancers.[39]

Niacinamide may be beneficial in treating psoriasis.[40]

There is tentative evidence for a potential role of niacinamide in treating acne, rosacea, autoimmune blistering disorders, ageing skin, and atopic dermatitis.[39] Niacinamide also inhibits poly(ADP-ribose) polymerases (PARP-1), enzymes involved in the rejoining of DNA strand breaks induced by radiation or chemotherapy.[41] ARCON (accelerated radiotherapy plus carbogen inhalation and nicotinamide) has been studied in cancer.[42]

Research has suggested niacinamide may play a role in the treatment of HIV.[43]

References

  1. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ISBN 978-1-139-43773-8. Archived
    from the original on 30 December 2016.
  3. ^
    ISBN 978-92-4-154765-9
    .
  4. ^
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  8. ^ a b "Niacinamide Use During Pregnancy". Drugs.com. Archived from the original on 30 December 2016. Retrieved 29 December 2016.
  9. ^ a b c "Niacinamide: Indications, Side Effects, Warnings". Drugs.com. 6 June 2017. Archived from the original on 5 August 2017. Retrieved 30 June 2017.
  10. ^
    ISBN 978-3-642-12264-4. Archived
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  12. ISBN 978-0-470-01552-0. Archived
    from the original on 30 December 2016.
  13. ^
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    .
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    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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    . WHO/MHP/HPS/EML/2021.02.
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  32. PMID 15728403
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  33. ^ a b Casiday R, Herman C, Frey R (5 September 2008). "Energy for the Body: Oxidative Phosphorylation". www.chemistry.wustl.edu. Department of Chemistry, Washington University in St. Louis. Archived from the original on 22 November 2016. Retrieved 14 March 2017.
  34. S2CID 28160151
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  35. ^ Ranaweera A (2017). "Nicotinamide". DermNet New Zealand (www.dermnetnz.org). DermNet New Zealand Trust. Archived from the original on 25 March 2017. Retrieved 30 June 2017.
  36. ^ British Pharmacopoeia Commission Secretariat (2009). Index, BP 2009 (PDF). Archived from the original (PDF) on 22 July 2011. Retrieved 4 February 2010.
  37. ^ Japanese Pharmacopoeia (PDF) (15th ed.). 2006. Archived from the original (PDF) on 22 July 2011. Retrieved 4 February 2010.
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  41. ^ "Definition of niacinamide". NCI Drug Dictionary. National Cancer Institute. 2 February 2011. Archived from the original on 28 April 2015. Retrieved 30 June 2017.
  42. PMID 12473514
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  43. ^ Mandavilli A (7 July 2020). "Patient Is Reported Free of H.I.V., but Scientists Urge Caution". The New York Times. Archived from the original on 23 September 2020. Retrieved 22 September 2020.
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