fbpx
Wikipedia

Nicotinamide

January 01, 1970

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.

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
Routes of
administration		oral, topical
ATC code
Legal status
Legal status
Identifiers
  • pyridine-3-carboxamide
CAS Number
  • 98-92-0  Y
PubChem CID
  • 936
DrugBank
  • DB02701
ChemSpider
  • 911
UNII
  • 25X51I8RD4
KEGG
  • D00036
ChEBI
  • CHEBI:17154
ChEMBL
  • ChEMBL1140
CompTox Dashboard (EPA)
  • DTXSID2020929
ECHA InfoCard100.002.467
Chemical and physical data
FormulaC6H6N2O
Molar mass122.127 g·mol−1
3D model (JSmol)
  • Interactive image
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

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 edit

Niacin deficiency edit

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

Acne edit

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 edit

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 edit

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 edit

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]

 

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)

Industrial production edit

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 edit

 
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 edit

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 edit

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 edit

Research edit

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 edit

  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. from the original on 30 December 2016.
  3. ^ a b c d 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. ^ a b c 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. ^ a b c d e f 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. (PDF) from the original on 22 September 2017. Retrieved 20 April 2018.
  7. ^ a b 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. ^ a b "Niacinamide Use During Pregnancy". Drugs.com. 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. from the original on 5 August 2017. Retrieved 30 June 2017.
  10. ^ a b 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. 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. 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. from the original on 30 December 2016.
  13. ^ a b c d 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. ^ a b 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. 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. 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. 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. from the original on 5 November 2017.
  31. ^ a b 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. (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. ^ 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. 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. from the original on 25 March 2017. Retrieved 30 June 2017.
  36. ^ British Pharmacopoeia Commission Secretariat (2009). (PDF). Archived from the original (PDF) on 22 July 2011. Retrieved 4 February 2010.
  37. ^ (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. ^ a b 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. 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. from the original on 23 September 2020. Retrieved 22 September 2020.

January 01, 1970
nicotinamide, niacinamide, nicotinamide, form, vitamin, found, food, used, dietary, supplement, medication, supplement, used, orally, swallowed, mouth, prevent, treat, pellagra, niacin, deficiency, while, nicotinic, acid, niacin, used, this, purpose, niacinami. 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 NicotinamideClinical dataPronunciation ˌ n aɪ e ˈ s ɪ n e m aɪ d ˌ n ɪ k e ˈ t ɪ n e m aɪ d Other namesNAM 3 pyridinecarboxamideniacinamidenicotinic acid amidevitamin PPnicotinic amidevitamin B3AHFS Drugs comConsumer Drug InformationLicense dataUS DailyMed NiacinamideRoutes ofadministrationoral topicalATC codeA11HA01 WHO Legal statusLegal statusUS OTCIdentifiersIUPAC name pyridine 3 carboxamideCAS Number98 92 0 YPubChem CID936DrugBankDB02701ChemSpider911UNII25X51I8RD4KEGGD00036ChEBICHEBI 17154ChEMBLChEMBL1140CompTox Dashboard EPA DTXSID2020929ECHA InfoCard100 002 467Chemical and physical dataFormulaC 6H 6N 2OMolar mass122 127 g mol 13D model JSmol Interactive imageDensity1 40 g cm3 g cm3 1 Melting point129 5 C 265 1 F Boiling point334 C 633 F SMILES c1cc cnc1 C O NInChI InChI 1S C6H6N2O c7 6 9 5 2 1 3 8 4 5 h1 4H H2 7 9 Key DFPAKSUCGFBDDF UHFFFAOYSA N 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 Contents 1 Medical uses 1 1 Niacin deficiency 1 2 Acne 1 3 Skin cancer 2 Side effects 3 Chemistry 3 1 Industrial production 3 2 Biochemistry 3 3 Biological role 4 Food sources 5 Compendial status 6 Research 7 ReferencesMedical uses editNiacin deficiency edit Niacinamide is the preferred treatment for pellagra caused by niacin deficiency 3 Acne edit 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 edit 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 editNiacinamide 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 editThe 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 nbsp 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 nbsp NAD the oxidized form of NADH contains the nicotinamide moiety highlighted in red Industrial production edit 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 edit nbsp 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 edit 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 editNiacinamide 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 editBritish Pharmacopoeia 36 Japanese Pharmacopoeia 37 Research editA 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 edit Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health 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 a b c d 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 a b c British National Formulary BNF 69 69th ed British Medical Association 2015 p 822 ISBN 978 0 85711 156 2 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 a b c d e f 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 a b 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 a b Niacinamide Use During Pregnancy Drugs com Archived from the original on 30 December 2016 Retrieved 29 December 2016 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 a b Krutmann J Humbert P 2010 Nutrition for Healthy Skin Strategies for Clinical and Cosmetic Practice Springer Science amp Business Media p 153 ISBN 978 3 642 12264 4 Archived from the original on 10 April 2017 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 Sneader W 2005 Drug Discovery A History John Wiley amp Sons p 231 ISBN 978 0 470 01552 0 Archived from the original on 30 December 2016 a b c d 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 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 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 a b 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 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 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 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 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 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 Taylor EC Crovetti AJ 1957 Nicotinamide 1 oxide Organic Syntheses 37 63 doi 10 15227 orgsyn 037 0063 Collected Volumes vol 4 p 704 Taylor EC Crovetti AJ 1957 2 Chloronicitinonitrile Organic Syntheses 37 12 doi 10 15227 orgsyn 037 0012 Collected Volumes vol 4 p 166 Teague PC Short WA 1953 Nicotinonitrile Organic Syntheses 33 52 doi 10 15227 orgsyn 033 0052 Collected Volumes vol 4 p 706 Allen CF Wolf CN 1950 3 Aminopyridine Organic Syntheses 30 3 doi 10 15227 orgsyn 030 0003 Collected Volumes vol 4 p 45 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 Hilterhaus L Liese A 2007 Building Blocks In Ulber R Sell D eds White Biotechnology Advances in Biochemical Engineering Biotechnology Vol 105 Springer Science amp 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 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 Petersen M Kiener A 1999 Biocatalysis Green Chem 1 2 99 106 doi 10 1039 A809538H 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 a b 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 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 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 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 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 British Pharmacopoeia Commission Secretariat 2009 Index BP 2009 PDF Archived from the original PDF on 22 July 2011 Retrieved 4 February 2010 Japanese Pharmacopoeia PDF 15th ed 2006 Archived from the original PDF on 22 July 2011 Retrieved 4 February 2010 Minocha R Damian DL Halliday GM January 2018 Melanoma and nonmelanoma skin cancer chemoprevention A role for nicotinamide Photodermatology Photoimmunology amp Photomedicine 34 1 5 12 doi 10 1111 phpp 12328 PMID 28681504 a b 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 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 Definition of niacinamide NCI Drug Dictionary National Cancer Institute 2 February 2011 Archived from the original on 28 April 2015 Retrieved 30 June 2017 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 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 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Nicotinamide amp oldid 1220213859, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.