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Nicotinamide

Nicotinamide
Clinical data
Pronunciation/ˌnaɪəˈsɪnəmaɪd/, /ˌnɪkəˈtɪnəmaɪd/
Other namesNAM, 3-pyridinecarboxamide
niacinamide (USAN US)
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.467 Edit 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, BAN UK[2]) or niacinamide (USAN US) is a form of vitamin B3 found in food and used as a dietary supplement and medication.[3][4][5] As a supplement, it is used orally (swallowed by mouth) to prevent and treat pellagra (niacin deficiency).[4] While nicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causing skin flushing.[4] 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.[5][6] It is a water-soluble vitamin.

Side effects are minimal.[7][8] At high doses, liver problems may occur.[7] Normal amounts are safe for use during pregnancy.[9] Nicotinamide is in the vitamin B family of medications, specifically the vitamin B3 complex.[10][11] It is an amide of nicotinic acid.[7] Foods that contain nicotinamide include yeast, meat, milk, and green vegetables.[12]

Nicotinamide was discovered between 1935 and 1937.[13][14] It is on the World Health Organization's List of Essential Medicines.[15][16] Nicotinamide is available as a generic medication and over the counter.[10] Commercially, nicotinamide is made from either nicotinic acid (niacin) or nicotinonitrile.[14][17] In some countries, grains have nicotinamide added to them.[14]

  1. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ Sweetman SC (2011). Martindale: the complete drug reference. Martindale (37 ed.). London: Pharmaceutical press. p. 2117. ISBN 978-0-85369-933-0. OCLC 1256529676.
  3. ^ 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.
  4. ^ a b c 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.
  5. ^ a b British National Formulary: BNF 69 (69th ed.). British Medical Association. 2015. p. 822. ISBN 978-0-85711-156-2.
  6. ^ 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.
  7. ^ a b c 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.
  8. ^ 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.
  9. ^ "Niacinamide Use During Pregnancy". Drugs.com. Archived from the original on 30 December 2016. Retrieved 29 December 2016.
  10. ^ a b "Niacinamide: Indications, Side Effects, Warnings". Drugs.com. 6 June 2017. Archived from the original on 5 August 2017. Retrieved 30 June 2017.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ a b c 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.
  15. ^ 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.
  16. ^ 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.
  17. ^ Cite error: The named reference Synthesis2015 was invoked but never defined (see the help page).
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