Nicotinamide

Last updated

Nicotinamide
Nicotinamid.svg
Nicotinamide-from-xtal-2011-Mercury-3D-sf.png
Clinical data
Pronunciation /ˌnaɪəˈsɪnəmaɪd/ , /ˌnɪkəˈtɪnəmaɪd/
Other namesNAM, 3-pyridinecarboxamide
niacinamide
nicotinic acid amide
vitamin PP
nicotinic amide
vitamin B3
AHFS/Drugs.com Consumer Drug Information
License data
Routes of
administration 		oral, topical
ATC code
Legal status
Legal status
Identifiers
  • pyridine-3-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.002.467 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C6H6N2O
Molar mass 122.127 g·mol−1
3D model (JSmol)
Density 1.40 g/cm3 g/cm3 [1]
Melting point 129.5 °C (265.1 °F)
Boiling point 334 °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 vitamin B3 found in food and used as a dietary supplement and medication. [2] [3] [4] As a supplement, it is used orally (swallowed by mouth) to prevent and treat pellagra (niacin deficiency). [3] While nicotinic acid (niacin) may be used for this purpose, niacinamide has the benefit of not causing skin flushing. [3] As a cream, it is used to treat acne, and has been observed in clinical studies to improve the appearance of aging skin by reducing hyperpigmentation and redness. [4] [5] It is a water-soluble vitamin. Niacinamide is the supplement name, while nicotinamide is the scientific name.

Contents

Side effects are minimal. [6] [7] At high doses, liver problems may occur. [6] Normal amounts are safe for use during pregnancy. [8] Niacinamide is in the vitamin B family of medications, specifically the vitamin B3 complex. [9] [10] It is an amide of nicotinic acid. [6] Foods that contain niacinamide include yeast, meat, milk, and green vegetables. [11]

Niacinamide was discovered between 1935 and 1937. [12] [13] It is on the World Health Organization's List of Essential Medicines. [14] [15] Niacinamide is available as a generic medication and over the counter. [9] Commercially, niacinamide is made from either nicotinic acid (niacin) or nicotinonitrile. [13] [16] In some countries, 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 ceramides in human keratinocytes in vitro and improves the epidermal permeability barrier in vivo. [18] The application of 2% topical niacinamide for 2 and 4 weeks has been found to be effective in lowering the sebum excretion rate. [19] Niacinamide has been shown to prevent Cutibacterium acnes -induced activation 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. [6] [7] At very high doses above 3g/ day acute 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 pyridine ring to which a primary amide group is attached in the meta position. It is an amide of nicotinic acid. [6] As an aromatic compound, it undergoes electrophilic substitution reactions and transformations of its two functional groups. Examples of these reactions reported in Organic Syntheses include the preparation of 2-chloronicotinonitrile by a two-step process via the N-oxide, [22] [23]

Nicotinamide to 2-chloronicotinonitrile.png

from nicotinonitrile by reaction with phosphorus pentoxide, [24] and 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) Nicotinamide highlighted in NAD+.svg
NAD , the oxidized form of NADH, contains the nicotinamide moiety (highlighted in red)

Industrial production

The hydrolysis of nicotinonitrile is catalysed by the enzyme nitrile hydratase from Rhodococcus rhodochrous J1, [26] [27] [16] producing 3500 tons per annum of nicotinamide for use in animal feed. [28] The enzyme allows for a more selective synthesis as further hydrolysis of the amide to 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. NAD+ Oxidation and Reduction.png
The active Nicotinamide group on the molecule NAD undergoes oxidation in many metabolic pathways.

Nicotinamide, as a part of the cofactor nicotinamide adenine dinucleotide (NADH / NAD+) is crucial to life. In cells, nicotinamide is incorporated into NAD+ and nicotinamide adenine dinucleotide phosphate (NADP+). NAD+ and NADP+ are cofactors in a wide variety of enzymatic oxidation-reduction reactions, most notably glycolysis, the citric acid cycle, and the electron transport chain. [31] 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 a 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 B family and specifically 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]

Related Research Articles

<span class="mw-page-title-main">Niacin</span> Organic compound and a form of vitamin B3

Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds. Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness. Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated as MeCHO. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

<span class="mw-page-title-main">Pellagra</span> Human disease caused by a lack of vitamin niacin

Pellagra is a disease caused by a lack of the vitamin niacin (vitamin B3). Symptoms include inflamed skin, diarrhea, dementia, and sores in the mouth. Areas of the skin exposed to friction and radiation are typically affected first. Over time affected skin may become darker, stiffen, peel, or bleed.

<span class="mw-page-title-main">Nicotinamide adenine dinucleotide</span> Chemical compound which is reduced and oxidized

Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other, nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen), respectively.

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base. An alternative name is chlorhydrate, which comes from French. An archaic alternative name is muriate, derived from hydrochloric acid's ancient name: muriatic acid.

<span class="mw-page-title-main">Nicotinamide adenine dinucleotide phosphate</span> Chemical compound

Nicotinamide adenine dinucleotide phosphate, abbreviated NADP+ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NADPH as a reducing agent ('hydrogen source'). NADPH is the reduced form, whereas NADP+ is the oxidized form. NADP+ is used by all forms of cellular life.

<span class="mw-page-title-main">Hyperpigmentation</span> Skin condition

Hyperpigmentation is the darkening of an area of skin or nails caused by increased melanin.

The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one less carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate. The reaction can form a wide range of products, including alkyl and aryl amines.

<span class="mw-page-title-main">Hartnup disease</span> Metabolic disorder

Hartnup disease is an autosomal recessive metabolic disorder affecting the absorption of nonpolar amino acids. Niacin is a precursor to nicotinamide, a necessary component of NAD+.

<span class="mw-page-title-main">Cyclopropanation</span> Chemical process which generates cyclopropane rings

In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics. However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner.

<span class="mw-page-title-main">Heterocyclic amine</span> Any heterocyclic compound having at least one nitrogen heteroatom

Heterocyclic amines, also sometimes referred to as HCAs, are chemical compounds containing at least one heterocyclic ring, which by definition has atoms of at least two different elements, as well as at least one amine (nitrogen-containing) group. Typically it is a nitrogen atom of an amine group that also makes the ring heterocyclic, though compounds exist in which this is not the case. The biological functions of heterocyclic amines vary, including vitamins and carcinogens. Carcinogenic heterocyclic amines are created by high temperature cooking of meat and smoking of plant matter like tobacco. Some well known heterocyclic amines are niacin, nicotine, and the nucleobases that encode genetic information in DNA.

Carboxylation is a chemical reaction in which a carboxylic acid is produced by treating a substrate with carbon dioxide. The opposite reaction is decarboxylation. In chemistry, the term carbonation is sometimes used synonymously with carboxylation, especially when applied to the reaction of carbanionic reagents with CO2. More generally, carbonation usually describes the production of carbonates.

<span class="mw-page-title-main">Benzyl cyanide</span> Chemical compound

Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. It is also an important pheromone in certain species.

Vitamins occur in a variety of related forms known as vitamers. A vitamer of a particular vitamin is one of several related compounds that performs the functions of said vitamin and prevents the symptoms of deficiency of said vitamin.

<span class="mw-page-title-main">Propionaldehyde</span> Chemical compound

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a pungent and fruity odour. It is produced on a large scale industrially.

<span class="mw-page-title-main">Nicotinamide riboside</span> Chemical compound

Nicotinamide riboside (NR, SR647) is a pyridine-nucleoside and a form of vitamin B3. It functions as a precursor to nicotinamide adenine dinucleotide, or NAD+, through a two-step and a three-step pathway.

Vitamin B<sub>3</sub> Class of chemically related vitamers

Vitamin B3, colloquially referred to as niacin, is a vitamin family that includes three forms, or vitamers: niacin (nicotinic acid), nicotinamide (niacinamide), and nicotinamide riboside. All three forms of vitamin B3 are converted within the body to nicotinamide adenine dinucleotide (NAD). NAD is required for human life and people are unable to make it within their bodies without either vitamin B3 or tryptophan. Nicotinamide riboside was identified as a form of vitamin B3 in 2004.

<span class="mw-page-title-main">Nicotinonitrile</span> Chemical compound

Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC5H4N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine:

<span class="mw-page-title-main">Menthyl nicotinate</span> Chemical compound

Menthyl nicotinate is an organic compound with the formula C16H23NO2. It is the ester of nicotinic acid (niacin, vitamin B3) and menthol. At room temperature, menthyl nicotinate is a colorless, odorless, viscous liquid.

References

  1. ↑ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ↑ Bender DA (2003). Nutritional Biochemistry of the Vitamins. Cambridge University Press. p. 203. ISBN   978-1-139-43773-8. Archived from the original on 30 December 2016.
  3. 1 2 3 4 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 496, 500. hdl: 10665/44053 . ISBN   978-92-4-154765-9.
  4. 1 2 3 British National Formulary: BNF 69 (69th ed.). British Medical Association. 2015. p. 822. ISBN   978-0-85711-156-2.
  5. ↑ Bissett DL, Oblong JE, Berge CA (July 2005). "Niacinamide: A B vitamin that improves aging facial skin appearance". Dermatologic Surgery. 31 (7 Pt 2): 860–5, discussion 865. doi:10.1111/j.1524-4725.2005.31732. PMID   16029679.
  6. 1 2 3 4 5 6 Knip M, Douek IF, Moore WP, Gillmor HA, McLean AE, Bingley PJ, et al. (November 2000). "Safety of high-dose nicotinamide: a review" (PDF). Diabetologia. 43 (11): 1337–45. doi: 10.1007/s001250051536 . PMID   11126400. S2CID   24763480. Archived (PDF) from the original on 22 September 2017. Retrieved 20 April 2018.
  7. 1 2 MacKay D, Hathcock J, Guarneri E (June 2012). "Niacin: chemical forms, bioavailability, and health effects". Nutrition Reviews. 70 (6): 357–66. doi: 10.1111/j.1753-4887.2012.00479.x . PMID   22646128.
  8. 1 2 "Niacinamide Use During Pregnancy". Drugs.com . Archived from the original on 30 December 2016. Retrieved 29 December 2016.
  9. 1 2 3 "Niacinamide: Indications, Side Effects, Warnings". Drugs.com . 6 June 2017. Archived from the original on 5 August 2017. Retrieved 30 June 2017.
  10. 1 2 Krutmann J, Humbert P (2010). Nutrition for Healthy Skin: Strategies for Clinical and Cosmetic Practice. Springer Science & Business Media. p. 153. ISBN   978-3-642-12264-4. Archived from the original on 10 April 2017.
  11. ↑ Burtis CA, Ashwood ER, Bruns DE (2012). Tietz Textbook of Clinical Chemistry and Molecular Diagnostics (5th ed.). Elsevier Health Sciences. p. 934. ISBN   978-1-4557-5942-2. Archived from the original on 30 December 2016.
  12. ↑ Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 231. ISBN   978-0-470-01552-0. Archived from the original on 30 December 2016.
  13. 1 2 3 4 Blum R (2015). "Vitamins, 11. Niacin (Nicotinic Acid, Nicotinamide)". Vitamins, 11. Niacin (Nicotinic Acid, Nicotinamide. Ullmann's Encyclopedia of Industrial Chemistry (6th ed.). Weinheim: Wiley-VCH. pp. 1–9. doi:10.1002/14356007.o27_o14.pub2. ISBN   978-3-527-30385-4.
  14. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  15. ↑ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl: 10665/345533 . WHO/MHP/HPS/EML/2021.02.
  16. 1 2 Schmidberger JW, Hepworth LJ, Green AP, Flitsch SL (2015). "Enzymatic Synthesis of Amides". In Faber K, Fessner WD, Turner NJ (eds.). Biocatalysis in Organic Synthesis 1. Science of Synthesis. Georg Thieme Verlag. pp. 329–372. ISBN   978-3-13-176611-3. Archived from the original on 5 November 2017.
  17. ↑ Niren NM (January 2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis. 77 (1 Suppl): 11–6. PMID   16871774.
  18. ↑ Tanno O, Ota Y, Kitamura N, Katsube T, Inoue S (September 2000). "Nicotinamide increases biosynthesis of ceramides as well as other stratum corneum lipids to improve the epidermal permeability barrier". The British Journal of Dermatology. 143 (3): 524–31. doi:10.1111/j.1365-2133.2000.03705.x. PMID   10971324. S2CID   21874670.
  19. ↑ Draelos ZD, Matsubara A, Smiles K (June 2006). "The effect of 2% niacinamide on facial sebum production". Journal of Cosmetic and Laser Therapy. 8 (2): 96–101. doi:10.1080/14764170600717704. PMID   16766489. S2CID   36713665.
  20. ↑ Kim J, Ochoa MT, Krutzik SR, Takeuchi O, Uematsu S, Legaspi AJ, et al. (August 2002). "Activation of toll-like receptor 2 in acne triggers inflammatory cytokine responses". Journal of Immunology. 169 (3): 1535–41. doi:10.4049/jimmunol.169.3.1535. PMC   4636337 . PMID   12133981.
  21. ↑ Snaidr VA, Damian DL, Halliday GM (February 2019). "Nicotinamide for photoprotection and skin cancer chemoprevention: A review of efficacy and safety". Experimental Dermatology. 28 (Suppl 1): 15–22. doi: 10.1111/exd.13819 . PMID   30698874.
  22. ↑ Taylor EC, Crovetti AJ (1957). "Nicotinamide-1-oxide". Organic Syntheses . 37: 63. doi:10.15227/orgsyn.037.0063 ; Collected Volumes, vol. 4, p. 704.
  23. ↑ Taylor EC, Crovetti AJ (1957). "2-Chloronicitinonitrile". Organic Syntheses . 37: 12. doi:10.15227/orgsyn.037.0012 ; Collected Volumes, vol. 4, p. 166.
  24. ↑ Teague PC, Short WA (1953). "Nicotinonitrile". Organic Syntheses . 33: 52. doi:10.15227/orgsyn.033.0052 ; Collected Volumes, vol. 4, p. 706.
  25. ↑ Allen CF, Wolf CN (1950). "3-Aminopyridine". Organic Syntheses . 30: 3. doi:10.15227/orgsyn.030.0003 ; Collected Volumes, vol. 4, p. 45.
  26. ↑ Nagasawa T, Mathew CD, Mauger J, Yamada H (July 1988). "Nitrile Hydratase-Catalyzed Production of Nicotinamide from 3-Cyanopyridine in Rhodococcus rhodochrous J1". Applied and Environmental Microbiology. 54 (7): 1766–1769. Bibcode:1988ApEnM..54.1766N. doi:10.1128/AEM.54.7.1766-1769.1988. PMC   202743 . PMID   16347686.
  27. ↑ Hilterhaus L, Liese A (2007). "Building Blocks". In Ulber R, Sell D (eds.). White Biotechnology. Advances in Biochemical Engineering / Biotechnology. Vol. 105. Springer Science & Business Media. pp. 133–173. doi:10.1007/10_033. ISBN   978-3-540-45695-7. PMID   17408083. S2CID   34552222. Archived from the original on 5 November 2017.
  28. ↑ Asano Y (2015). "Hydrolysis of Nitriles to Amides". In Faber K, Fessner WD, Turner NJ (eds.). Biocatalysis in Organic Synthesis 1. Science of Synthesis. Georg Thieme Verlag. pp. 255–276. ISBN   978-3-13-176611-3. Archived from the original on 5 November 2017.
  29. ↑ Petersen M, Kiener A (1999). "Biocatalysis". Green Chem. 1 (2): 99–106. doi:10.1039/A809538H.
  30. ↑ Servi S, Tessaro D, Hollmann F (2015). "Historical Perspectives: Paving the Way for the Future". In Faber NJ, Fessner WD, Turner K (eds.). Biocatalysis in Organic Synthesis 1. Science of Synthesis. Georg Thieme Verlag. pp. 1–39. ISBN   978-3-13-176611-3. Archived from the original on 5 November 2017.
  31. 1 2 Belenky P, Bogan KL, Brenner C (January 2007). "NAD+ metabolism in health and disease" (PDF). Trends in Biochemical Sciences. 32 (1): 12–9. doi:10.1016/j.tibs.2006.11.006. PMID   17161604. Archived (PDF) from the original on 27 September 2007.
  32. ↑ Williams AC, Cartwright LS, Ramsden DB (March 2005). "Parkinson's disease: the first common neurological disease due to auto-intoxication?". QJM. 98 (3): 215–26. doi: 10.1093/qjmed/hci027 . PMID   15728403.
  33. 1 2 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. ↑ Rolfe HM (December 2014). "A review of nicotinamide: treatment of skin diseases and potential side effects". Journal of Cosmetic Dermatology. 13 (4): 324–8. doi:10.1111/jocd.12119. PMID   25399625. S2CID   28160151.
  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.
  38. ↑ Minocha R, Damian DL, Halliday GM (January 2018). "Melanoma and nonmelanoma skin cancer chemoprevention: A role for nicotinamide?". Photodermatology, Photoimmunology & Photomedicine. 34 (1): 5–12. doi: 10.1111/phpp.12328 . PMID   28681504.
  39. 1 2 Chen AC, Damian DL (August 2014). "Nicotinamide and the skin". The Australasian Journal of Dermatology. 55 (3): 169–75. doi:10.1111/ajd.12163. PMID   24635573. S2CID   45745255.
  40. ↑ Namazi MR (August 2003). "Nicotinamide: a potential addition to the anti-psoriatic weaponry". FASEB Journal. 17 (11): 1377–9. doi: 10.1096/fj.03-0002hyp . PMID   12890690. S2CID   39752891.
  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. ↑ Kaanders JH, Bussink J, van der Kogel AJ (December 2002). "ARCON: a novel biology-based approach in radiotherapy". The Lancet. Oncology. 3 (12): 728–37. doi:10.1016/s1470-2045(02)00929-4. PMID   12473514.
  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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.