Nicotinamide

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Nicotinamide
Nicotinamid.svg
Nicotinamide-from-xtal-2011-Mercury-3D-sf.png
Clinical data
Pronunciation /ˌnɪkəˈtɪnəmd/
AHFS/Drugs.com Consumer Drug Information
Pregnancy
category
Routes of
administration
by mouth, topical
ATC code A11HA01 (WHO)
Identifiers
Synonyms 3-pyridinecarboxamide
niacinamide
nicotinic acid amide
vitamin PP
nicotinic amide
CAS Number 98-92-0  YesY
PubChem (CID) 936
DrugBank DB02701
ChemSpider 911
UNII 25X51I8RD4
KEGG D00036
ChEBI CHEBI:17154
ChEMBL CHEMBL1140
ECHA InfoCard 100.002.467
Chemical and physical data
Formula C6H6N2O
Molar mass 122.13 g·mol−1
3D model (Jmol) Interactive image
Density 1.40 g/cm3[2] g/cm3
Melting point 129.5 °C (265.1 °F)
Boiling point 334 °C (633 °F)

Nicotinamide (NAA), also known as niacinamide, is a vitamin found in food, used as a dietary supplement, and used as a medication.[3][4][5] As a supplement it is used by mouth to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used nicotinamide has the benefit of not causing skin flushing.[4] As a cream it is used to treat acne.[5]

Side effects are minimal.[6][7] At high doses liver problems may occur.[6] Normal amounts are safe for use during pregnancy.[1] Nicotinamide is in the vitamin B family of medications.[8] It is an amide of nicotinic acid.[6] Foods that contain nicotinamide include yeast, meat, milk, and green vegetables.[9]

Nicotinamide was discovered between 1935 and 1937.[10][11] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[12] Nicotinamide is available as a generic medication and over the counter.[8] In the United Kingdom a 60 gm tube costs the NHS about 7.10 pounds.[5] Commercially nicotinamide is made from either nicotinic acid or 3-cyanopyridine. In a number of countries grains have nicotinamide added to them.[11]

Medical uses[edit]

Niacin deficiency[edit]

Nicotinamide is the preferred treatment for niacin deficiency (pellagra).[4]

Small intestinal bacterial overgrowth is one known cause of nicotinamide deficiency.

Acne[edit]

Nicotinamide in the form of a cream is used as a treatment for acne.[5]

It has anti-inflammatory actions. These may be of benefit to people with inflammatory skin conditions.[13]

Nicotinamide increases the biosynthesis of ceramides in human keratinocytes in vitro and improves the epidermal permeability barrier in vivo.[14] The application of 2% topical nicotinamide for 2 and 4 weeks has been found to be effective in lowering the sebum excretion rate in study participants.[15] Nictotinamide has been shown to prevent Propionibacterium acnes-induced activation of toll-like receptor (TLR)-2, which ultimately results in the down-regulation of pro-inflammatory IL-8 production.[16]

Side effects[edit]

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 g/day and unsupervised use should be discouraged.[6] Overall, however, it rarely causes side effects, and is considered generally safe as a food additive, and as a component in cosmetics and medication.[17]

Mechanism[edit]

In cells, niacin is incorporated into nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP), although the pathways for nicotinic acid amide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction reactions.[18]

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.[19]

Some countries require fortification with nicotinamide of some foods. For example, the UK requires fortification of flour and bread with nicotinamide.

Nicotinamide is an ingredient in some energy shots such as 5-hour Energy.[20][21]

Production[edit]

In 2014 31,000 tones of nicotinamide were sold.[11]

Compendial status[edit]

Research[edit]

There is tentative evidence that it may reduce the risk of skin cancer.

[24] There is also tentative evidence for bullous pemphigoid.[24]

Nicotinamide may aid chemotherapy-and-radiation therapy by acting as a sensitizing agent/cancer-growth-promoter resulting in enhanced blood flow to tumors and thus increased oxygen supply to tumors, 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.[25]

See also[edit]

Notes and references[edit]

  1. ^ a b "Niacinamide Use During Pregnancy | Drugs.com". www.drugs.com. Retrieved 29 December 2016. 
  2. ^ Record in the GESTIS Substance Database of the IFA
  3. ^ Bender, David A. (2003). Nutritional Biochemistry of the Vitamins. Cambridge University Press. p. 203. ISBN 9781139437738. 
  4. ^ a b c WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 496, 500. ISBN 9789241547659. Retrieved 8 December 2016. 
  5. ^ a b c d British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 822. ISBN 9780857111562. 
  6. ^ a b c d Knip, M; Douek, IF; Moore, WP; Gillmor, HA; McLean, AE; Bingley, PJ; Gale, EA; European Nicotinamide Diabetes Intervention Trial, Group. (November 2000). "Safety of high-dose nicotinamide: a review.". Diabetologia. 43 (11): 1337–45. PMID 11126400. 
  7. ^ MacKay, D; Hathcock, J; Guarneri, E (June 2012). "Niacin: chemical forms, bioavailability, and health effects.". Nutrition reviews. 70 (6): 357–66. PMID 22646128. 
  8. ^ a b "Niacinamide: Indications, Side Effects, Warnings - Drugs.com". www.drugs.com. Retrieved 29 December 2016. 
  9. ^ Burtis, Carl A.; Ashwood, Edward R.; Bruns, David E. (2012). Tietz Textbook of Clinical Chemistry and Molecular Diagnostics (5 ed.). Elsevier Health Sciences. p. 934. ISBN 1455759422. 
  10. ^ Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 231. ISBN 9780470015520. 
  11. ^ a b c "Vitamins, 11. Niacin (Nicotinic Acid, Nicotinamide)". Ullmann's encyclopedia of industrial chemistry. (6 ed.). Weinheim: Wiley-VCH. 2015. ISBN 9783527303854. 
  12. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016. 
  13. ^ Niren NM (2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis. 77 (1 Suppl): 11–6. PMID 16871774. 
  14. ^ Tanno, O.; Ota, Y.; Kitamura, N.; Katsube, T.; Inoue, S. (2000-09-01). "Nicotinamide increases biosynthesis of ceramides as well as other stratum corneum lipids to improve the epidermal permeability barrier". British Journal of Dermatology. 143 (3): 524–531. doi:10.1111/j.1365-2133.2000.03705.x. ISSN 1365-2133. 
  15. ^ Draelos, Zoe Diana; Matsubara, Akira; Smiles, Kenneth (2006-01-01). "The effect of 2% niacinamide on facial sebum production". Journal of Cosmetic and Laser Therapy. 8 (2): 96–101. doi:10.1080/14764170600717704. ISSN 1476-4172. 
  16. ^ Kim, Jenny; Ochoa, Maria-Teresa; Krutzik, Stephan R.; Takeuchi, Osamu; Uematsu, Satoshi; Legaspi, Annaliza J.; Brightbill, Hans D.; Holland, Diana; Cunliffe, William J. (2002-08-01). "Activation of Toll-Like Receptor 2 in Acne Triggers Inflammatory Cytokine Responses". The Journal of Immunology. 169 (3): 1535–1541. doi:10.4049/jimmunol.169.3.1535. ISSN 0022-1767. PMID 12133981. 
  17. ^ Cosmetic Ingredient Review Expert Panel (2005). "Final report of the safety assessment of niacinamide and niacin". Int. J. Toxicol. 24 Suppl 5: 1–31. doi:10.1080/10915810500434183. PMID 16596767. 
  18. ^ Belenky P; Bogan KL; Brenner C (2007). "NAD+ metabolism in health and disease" (PDF). Trends Biochem. Sci. 32 (1): 12–9. doi:10.1016/j.tibs.2006.11.006. PMID 17161604. Retrieved 2007-12-23. 
  19. ^ Rolfe, Heidi M (2014-12-01). "A review of nicotinamide: treatment of skin diseases and potential side effects". Journal of Cosmetic Dermatology. 13 (4): 324–328. doi:10.1111/jocd.12119. ISSN 1473-2165. PMID 25399625. 
  20. ^ "5-hour Energy Shot Ingredients". 
  21. ^ http://theomegareview.com/home/wp-content/uploads/2015/08/5-Hour-Energy-Nutrition-Label.jpg
  22. ^ British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 4 February 2010. 
  23. ^ "Japanese Pharmacopoeia, Fifteenth Edition" (PDF). 2006. Retrieved 4 February 2010. 
  24. ^ a b Chen, AC; Damian, DL (August 2014). "Nicotinamide and the skin.". The Australasian journal of dermatology. 55 (3): 169–75. PMID 24635573. 
  25. ^ Definition of niacinamide, National Cancer Institute

External links[edit]