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Nicotinamide information


Nicotinamide
Clinical data
Pronunciation/ˌnəˈsɪnəmd/, /ˌnɪkəˈtɪnəmd/
Other namesNAM, 3-pyridinecarboxamide
niacinamide
nicotinic acid amide
vitamin PP
nicotinic amide
vitamin B3
AHFS/Drugs.comConsumer Drug Information
License data
  • US DailyMed: Niacinamide
Routes of
administration
oral, topical
ATC code
  • A11HA01 (WHO)
Legal status
Legal status
  • US: OTC
Identifiers
IUPAC name
  • pyridine-3-carboxamide
CAS Number
  • 98-92-0  checkY
PubChem CID
  • 936
DrugBank
  • DB02701
ChemSpider
  • 911
UNII
  • 25X51I8RD4
KEGG
  • D00036
ChEBI
  • CHEBI:17154
ChEMBL
  • ChEMBL1140
CompTox Dashboard (EPA)
  • DTXSID2020929 Edit this at Wikidata
ECHA InfoCard100.002.467 Edit this at Wikidata
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)
SMILES
  • c1cc(cnc1)C(=O)N
InChI
  • 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.

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]

  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. ^ 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.
  4. ^ a b 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 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. ^ 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. ^ "Niacinamide Use During Pregnancy". Drugs.com. Archived from the original on 30 December 2016. Retrieved 29 December 2016.
  9. ^ a b "Niacinamide: Indications, Side Effects, Warnings". Drugs.com. 6 June 2017. Archived from the original on 5 August 2017. Retrieved 30 June 2017.
  10. ^ 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. ^ 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.
  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. ^ Cite error: The named reference Synthesis2015 was invoked but never defined (see the help page).

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Nicotinamide

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Niacinamide or nicotinamide is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used orally (swallowed...

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Nicotinamide adenine dinucleotide

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Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists...

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Nicotinamide mononucleotide

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Nicotinamide mononucleotide ("NMN" and "β-NMN") is a nucleotide derived from ribose, nicotinamide, nicotinamide riboside and niacin. In humans, several...

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Nicotinamide riboside

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Nicotinamide riboside (NR, SR647) is a pyridine-nucleoside and a form of vitamin B3. It functions as a precursor to nicotinamide adenine dinucleotide,...

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Niacin

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amide derivative nicotinamide (niacinamide) is a component of the coenzymes nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide...

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Nicotinamide phosphoribosyltransferase

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Nicotinamide phosphoribosyltransferase (NAmPRTase or NAMPT), formerly known as pre-B-cell colony-enhancing factor 1 (PBEF1) or visfatin for its extracellular...

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Nicotinamide adenine dinucleotide phosphate

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Nicotinamide adenine dinucleotide phosphate, abbreviated NADP+ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic...

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Vitamin B3

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(nicotinic acid), nicotinamide (niacinamide), and nicotinamide riboside. All three forms of vitamin B3 are converted within the body to nicotinamide adenine dinucleotide...

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NMN nucleosidase

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the chemical reaction nicotinamide D-ribonucleotide + H2O ⇌ {\displaystyle \rightleftharpoons } D-ribose 5-phosphate + nicotinamide Thus, the two substrates...

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NMNAT1

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Nicotinamide mononucleotide adenylyltransferase 1 (NMNAT1) is an enzyme that in humans is encoded by the nmnat1 gene. It is a member of the nicotinamide-nucleotide...

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Nicotinamidase

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reaction nicotinamide + H2O ⇌ {\displaystyle \rightleftharpoons } nicotinate + NH3 Thus, the two substrates of this enzyme are nicotinamide and H2O, whereas...

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Dehydrogenase

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the other is nicotinamide. In order to reduce this molecule, a hydrogen and two electrons must be added to the 6-carbon ring of nicotinamide; one electron...

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Nicotinamide cofactor analogues

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Nicotinamide cofactor analogues (mNADs), also called nicotinamide coenzyme biomimetics (NCBs), are artificial compounds that mimic the natural nicotinamide...

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Nicotinamide nucleotide transhydrogenase

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Nicotinamide nucleotide transhydrogenase may stand for NAD(P)+ transhydrogenase (Re/Si-specific) NAD(P)+ transhydrogenase (Si-specific) NNT_(gene) This...

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Ribosylnicotinamide kinase

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+ N-ribosylnicotinamide ⇌ {\displaystyle \rightleftharpoons } ADP + nicotinamide ribonucleotide Thus, the two substrates of this enzyme are ATP and...

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Pimple

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skin irritation that may present similar as a mild allergy. Recently, nicotinamide (vitamin B3), applied topically, has been shown to be more effective...

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NNMT

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Nicotinamide N-methyltransferase (NNMT) is an enzyme that in humans is encoded by the NNMT gene. NNMT catalyzes the methylation of nicotinamide and similar...

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Redox

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intermediate steps, the reduced carbon compounds are used to reduce nicotinamide adenine dinucleotide (NAD+) to NADH, which then contributes to the creation...

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Pellagra

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may be assisted by urine testing. Treatment is with either niacin or nicotinamide supplementation. Improvements typically begin within a couple of days...

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Black Black

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and nicotinamide. A persistent urban legend holds that the gum contains nicotine, the misconception stemming from confusion with nicotinamide, a different...

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PP

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company pp, Papa Pontifex, post-nominal used by popes Vitamin PP or nicotinamide Paliperidone palmitate, an antipsychotic medication Pancreatic polypeptide...

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Biochemistry

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reducing equivalents of converting NAD+ (nicotinamide adenine dinucleotide: oxidized form) to NADH (nicotinamide adenine dinucleotide: reduced form). This...

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Metabolism

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phosphorylated or are coupled to nucleotides when they are used in cells. Nicotinamide adenine dinucleotide (NAD+), a derivative of vitamin B3 (niacin), is...

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Nicomide

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active ingredients nicotinamide, zinc, copper, and folic acid. The topical cream and topical gel are formulated into a 4% nicotinamide mixture. Dermatologists...

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