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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/04 19:18:12」(JST)

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Nicotinamide, (ni-kə-tē-nə-mīd) also known as niacinamide and nicotinic amide, is the amide of nicotinic acid (vitamin B₃ / niacin). Nicotinamide is a water-soluble vitamin and is part of the vitamin B group. Nicotinic acid, also known as niacin, is converted to nicotinamide in vivo, and, though the two are identical in their vitamin functions, nicotinamide does not have the same pharmacological and toxic effects of niacin, which occur incidental to niacin's conversion. Thus nicotinamide does not reduce cholesterol or cause flushing,^[1] although nicotinamide may be toxic to the liver at doses exceeding 3 g/day for adults.^[2] 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.^[3] Commercial production of niacin and niacinamide (several thousand tons annually) is by hydrolysis or aminolysis of 3-cyanopyridine (nicotinonitrile).^[4]

Use in medicine

Skin conditions

Nicotinamide has demonstrated anti-inflammatory actions that may be of benefit to patients with inflammatory skin conditions.^[5] These conditions include acne vulgaris, and the compound can suppress antigen-induced, lymphocytic transformation and inhibit 3',5'-cyclic-AMP phosphodiesterase. Nicotinamide has demonstrated the ability to block the inflammatory actions of iodides known to precipitate or exacerbate inflammatory acne.

NicAzel and Nicomide are the names of oral acne medications that include nicotinamide as their most predominant ingredient, based on this area of research. Nicotinamide is also found as part of a new adjunct supplement combination called, Azerizin^TM. According to the makers of Azerizin, this adjunct is part of their prescription dietary supplement product, which they claim helps manage inflammatory skin conditions. Nicotinamide is also used topically as a 4% or 5% gel or cream - as effective as topical 1% clindamycin (8-week double-blind trial) performed at the New York University College of Medicine.^[6] Unlike topical Erythromycin or Clindamycin it does not precipitate bacterial resistance in treating inflammatory acne. Nicotinamide acne treatment is also available as Nicotinamide pads and cream.

Nicotinamide is also reported to be an effective skin whitener in topical application.^[7]^[8]

Skin cancer

In a double-blind study of over 380 patients (average age 66) with at least two non-melanoma skin cancers in the last 5 years, the rates of new non-melanoma skin cancer diagnoses were 23% lower in the nicotinamide group (500mg bd) compared to the placebo group. The appearance of actinic keratoses were reduced in the supplement group as well by 11% at 3 months of treatment and by 20% at nine months. There was no effect beyond the 12-month treatment period, suggesting a rebound effect after the drug is stopped. There were no differences between the groups with regard to adverse events.^[9]

Anxiety

Studies show that nicotinamide has anxiolytic (anti-anxiety) properties. It may work in a way similar to benzodiazepines.^[10]^[11]^[12]

Alzheimer's disease

It is an activator of sirtuins (but inhibits at higher doses) and has been reported to restore cognition in Alzheimer's disease transgenic mice.^[13] A safety study of niacinamide for the treatment of Alzheimer's disease was begun in 2007^[update] at the University of California, Irvine.^[14]

Cancer

Nicotinamide conflicts as a chemo- and radio-sensitizing agent/cancer-growth-promoter by enhancing tumor blood flow, thus 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.^[15] PARP-1 appears to be an important target for triple negative breast cancers because the cells are sensitive to inhibition of PARP-1.^[16] Niacinamide is also used by some patients in combination with the popular but entirely unproven "intravenous vitamin C" treatment for cancer.^[17] It has also been seen to prevent immunosuppression caused by UVA and UVB radiation (so it could potentially be added to sunscreen).^[18]

Apoptosis

Nicotinamide can prevent apoptosis (programmed cell death) in cells exposed to agents that induce oxidative stress. Thus nicotinamide prevents apoptosis in human cortical neuronal cells when oxidative stress is induced by tertiary butylhydroperoxide,^[19] and in Jurkat (human T-cell lymphoma cells) when oxidative stress is induced by sodium deoxycholate.^[20]

Other

Nicotinamide reportedly increases the endurance of mice.^[21]

Food sources

Nicotinamide occurs in trace amounts mainly in meat, fish, nuts, and mushrooms, as well as to a lesser extent in some vegetables.

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

Toxicity

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.^[2] Overall, however, it rarely causes side effects, and is considered generally safe as a food additive, and as a component in cosmetics and medication.^[22]

Compendial status

British Pharmacopoeia^[23]
Japanese Pharmacopoeia^[24]

Notes and references

^ Jacenollo, P. (1992). Niacin versus niacinamide
^ ^a ^b Knip M; Douek IF; Moore WP et al. (2000). "Safety of high-dose nicotinamide: a review". Diabetologia 43 (11): 1337–45. doi:10.1007/s001250051536. PMID 11126400.
^ 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.
^ Manfred Eggersdorfer et al. (2000). "Vitamins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_443.
^ Niren NM (2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis 77 (1 Suppl): 11–6. PMID 16871774.
^ Shalita AR, Smith JG, Parish LC, Sofman MS, Chalker DK (June 1995). "Topical nicotinamide compared with clindamycin gel in the treatment of inflammatory acne vulgaris". International Journal of Dermatology 34 (6): 434–7. doi:10.1111/j.1365-4362.1995.tb04449.x. PMID 7657446.
^ Hakozaki T; Minwalla L; Zhuang J et al. (July 2002). "The effect of niacinamide on reducing cutaneous pigmentation and suppression of melanosome transfer". Br. J. Dermatol. 147 (1): 20–31. doi:10.1046/j.1365-2133.2002.04834.x. PMID 12100180.
^ Navarrete-Solís J; Castanedo-Cázares JP; Torres-Álvarez B et al. (July 2011). "A Double-Blind, Randomized Clinical Trial of Niacinamide 4% versus Hydroquinone 4% in the Treatment of Melasma". Dermatol Res Pract. 2011 (379173): 1. doi:10.1155/2011/379173. PMC 3142702. PMID 21822427.
^ Andrew James Martin; Andrew Chen; Bonita Choy; Pablo Fernandez Penas; Gary Halliday; Robyn Dalziell; Catriona McKenzie; Richard A Scolyer; Haryana M. Dhillon; Janette L. Vardy; Gaya St George; Nira Chinniah; Diona Damian (2015). "Oral nicotinamide to reduce actinic cancer: A phase 3 double-blind randomized controlled trial.". American Society of Clinical Oncology Annual Meeting, Chicago, 30 May 2015. J Clin Oncol 33, 2015 (suppl; abstr 9000).
^ Tallman JF, Paul SM, Skolnick P, Gallager DW (1980). "Receptors for the age of anxiety: pharmacology of the benzodiazepines". Science 207 (4428): 274–81. doi:10.1126/science.6101294. PMID 6101294.
^ Paul, SM; Marangos, PJ; Skolnick, P; Goodwin, FK (1982). "Biological substrates of anxiety: benzodiazepine receptors and endogenous ligands.". L'Encephale 8 (2): 131–44. PMID 6125374.
^ Akhundov, RA; Sultanov, AA; Gadzhily, RA; Sadykhov, RV (May 1993). "[Psychoregulating role of nicotinamide].". Biulleten' eksperimental'noi biologii i meditsiny 115 (5): 487–91. PMID 7913840.
^ Green KN, Steffan JS, Martinez-Coria H, Sun X, Schreiber SS, Thompson LM, LaFerla FM (2008-11-05). "Journal of Neuroscience - Nicotinamide Restores Cognition in Alzheimer's Disease Transgenic Mice via a Mechanism Involving Sirtuin Inhibition and Selective Reduction of Thr231-Phosphotau". Retrieved 2008-11-05. .
^ Safety Study of Nicotinamide to Treat Alzheimer's Disease, clinicaltrials.gov
^ Definition of niacinamide, National Cancer Institute
^ Efficacy of BSI-201, a poly (ADP-ribose) polymerase-1 (PARP1) inhibitor, in combination with gemcitabine/carboplatin (G/C) in patients with metastatic triple-negative breast cancer (TNBC): Results of a randomized phase II trial.
^ Intravenously administered vitamin C as cancer therapy: three cases
^ Damian DL, Patterson CR, Stapelberg M, Park J, Barnetson RS, Halliday GM (February 2008). "UV radiation-induced immunosuppression is greater in men and prevented by topical nicotinamide". J. Invest. Dermatol. 128 (2): 447–54. doi:10.1038/sj.jid.5701058. PMID 17882270.
^ Bhansali SG, Brazeau DA, Sonee M, Mukherjee SK. (2006). Nicotinamide prevents apoptosis in human cortical neuronal cells. Toxicol Mech Methods 16(4):173-180. doi: 10.1080/15376520500194726. PMID 20021043
^ Crowley CL, Payne CM, Bernstein H, Bernstein C, Roe D. (2000). The NAD+ precursors, nicotinic acid and nicotinamide protect cells against apoptosis induced by a multiple stress inducer, deoxycholate. Cell Death Differ 7(3):314-326. PMID 10745276
^ Fukuwatari T, Shibata K, Ishihara K, Fushiki T, Sugimoto E (April 2001). "Elevation of blood NAD level after moderate exercise in young women and mice". J. Nutr. Sci. Vitaminol. 47 (2): 177–9. doi:10.3177/jnsv.47.177. PMID 11508711.
^ 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.
^ British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 4 February 2010.
^ "Japanese Pharmacopoeia, Fifteenth Edition" (PDF). 2006. Retrieved 4 February 2010.

External links

DrugBank.ca Drug Card for Nicotinamide

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A robust amperometric sensor for β-nicotinamide adenine dinucleotide (NADH) detection was developed through the organic complex formation with ethylenediaminetetraacetic acid (EDTA) bonded on the polyethylenimine (PEI)/activated graphene oxide (AGO) layer. The EDTA immobilized sensor probe (GCE/AGO
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, , , , , , ,
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… Oligonol was able to improve diabetic indices, prevent the development of diabetic renal disease, and preserve renal cells and the renal morphological structure via the attenuation of reduced nicotinamide adenine dinucleotide phosphate (NADPH) oxidase-induced oxidative stress, inhibition of advanced glycation endproduct (AGE) generation, and prevention of apoptosis-induced cell death in db/db mice, being independent of changes in the body weight or serum glucose levels. …
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Related Pictures

★リンクテーブル★

リンク元	「ナイアシン」「ニコチン酸アミド」「ニコチンアミド」「niacinamide」
拡張検索	「nicotinamide phosphoribosyltransferase」「reduced nicotinamideadenine dinucleotide」「nicotinamide adenine dinucleotide」「N‐methylnicotinamide」

「ナイアシン」

Nicotinamide
Names
	IUPAC name pyridine-3-carboxamide
	Other names 3-pyridinecarboxamide; niacinamide; nicotinamide; nicotinic acid amide; Vitamin PP
Identifiers
CAS Registry Number	98-92-0
ATC code	A11HA01
ChEBI	CHEBI:17154
ChEMBL	ChEMBL1140
ChemSpider	911
DrugBank	DB02701
EC number	202-713-4
	InChI InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9) ; Key: DFPAKSUCGFBDDF-UHFFFAOYSA-N ; InChI=1/C6H6N2O/c7-6(9)5-2-1-3-8- 4-5/h1-4H,(H2,7,9)/f/h7H2 ; InChI=1/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9); Key: DFPAKSUCGFBDDF-UHFFFAOYAZ ;
Jmol-3D images	Image
KEGG	D00036
PubChem	936
	SMILES c1cc(cnc1)C(=O)N ;
UNII	25X51I8RD4
Properties
Chemical formula	C6H6N2O
Molar mass	122.13 g·mol−1
Density	1.4463g/cm3
Melting point	129.5 °C (265.1 °F; 402.6 K)
Boiling point	334 °C (633 °F; 607 K)
log P	-.37
Vapor pressure	1.3*10−4mmHg
Hazards
NFPA 704	0 1 0
Flash point	69 °C; 156 °F; 342 K
Autoignition; temperature	249 °C; 480 °F; 522 K
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

英: niacin
同: ビタミンB3？
関: nicotinamide, ニコチン酸 nicotinic acid nicotinic acid、ビタミン; Nicobid？

ビタミンB複合体の一つ。ニコチン酸とニコチン酸アミドがある。
ナイアシンはニコチン酸、ニコチンアミド、および生体内で活性を持つこれらの誘導体を総称していう(HIM.442)

⇔FB.196ではナイアシン = ニコチン酸、ナイアシンアミド = ニコチン酸アミドとしている。

厳密に言えば、生体内でトロプトファンから合成できる(その際にビタミンB6とriboflavinが必要)ので、ビタミンではない。トリプトファン60mgでナイアシン1mgに換算できる。ナイアシンはNADとなって、生体内で、酸化還元酵素の補酵素として機能するが、その他に、蛋白のADPリボシル化におけるADPリボースの供給源として、またDNA修復機構に関与するnucleoproteinのポリADPリボシル化にも関与している。(HBC.498)

臨床関連

ペラグラ：ナイアシン欠乏症
過剰摂取：(1-6g/dayのナイアシン服用は高脂血症治療のために用いられる)血管拡張・紅潮、皮膚の刺激感。(500mg/day以上の摂取)肝障害。(HBC.498)

「ニコチン酸アミド」

　　[★]

英: nicotinic acid amide, NAA
ラ: nicotinamidum
同: ニコチンアミド nicotinamide、ナイアシンアミド niacinamide、3-ピリジンカルボン酸アミド 3-pyridinecarboxylic acid amide
商: M.V.I.、Ｍ.Ｖ.Ｉ.-12、アミノレバンEN配合、エルネオパ1号、エレンタールP乳幼児用配合、エレンタール配合、エンシュア・リキッド、オーツカMV、シーパラ、ストミンA配合、ダイメジン・マルチ、ツインラインNF配合、ツインライン配合、ネオM.V.I.-9、ネオパレン1号、ネオラミン・マルチV、バンコマイシン塩酸塩、パンビタン、ビタジェクト、フェニルアラニン除去ミルク配合、フルカリック1号、ヘパンED配合、マルタミン、ラコールNF配合、ラコール配合、ロイシン・イソロイシン・バリン除去ミルク配合、ワッサーV配合
関: ナイアシン

ビタミン複合体の1つ。
NADやNADPの材料である。
治療のためには「ニコチン酸アミド散10%」を単独で使用する。

「ニコチンアミド」

　　[★]

英: nicotinamide
関: ニコチン酸アミド、ナイアシン。ビタミンB、vitamin B3、Nicobid

ビタミンB群の一種

「niacinamide」

　　[★] ナイアシンアミド

関: ニコチン酸アミド nicotinamide、vitamin B3

ビタミンB群の補酵素

「nicotinamide phosphoribosyltransferase」

　　[★]

ニコチンアミドホスホリボシルトランスフェラーゼ

「reduced nicotinamideadenine dinucleotide」

　　[★] 還元型ニコチンアミドアデニンジヌクレオチド

「nicotinamide adenine dinucleotide」

　　[★]

関: nADHcytochrome b5 reductase

同: NAD+

「N‐methylnicotinamide」

　　[★] N-メチルニコチンアミド

[1] Jacenollo, P. (1992). Niacin versus niacinamide

[Knip_M.2C_Douek_IF.2C_Moore_WP.2C_et_al._2000_1337.E2.80.9345-2] Knip M; Douek IF; Moore WP et al. (2000). "Safety of high-dose nicotinamide: a review". Diabetologia 43 (11): 1337–45. doi:10.1007/s001250051536. PMID 11126400.

[Belenky-3] 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.

[Ullmann-4] Manfred Eggersdorfer et al. (2000). "Vitamins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_443.

[5] Niren NM (2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis 77 (1 Suppl): 11–6. PMID 16871774.

[6] Shalita AR, Smith JG, Parish LC, Sofman MS, Chalker DK (June 1995). "Topical nicotinamide compared with clindamycin gel in the treatment of inflammatory acne vulgaris". International Journal of Dermatology 34 (6): 434–7. doi:10.1111/j.1365-4362.1995.tb04449.x. PMID 7657446.

[7] Hakozaki T; Minwalla L; Zhuang J et al. (July 2002). "The effect of niacinamide on reducing cutaneous pigmentation and suppression of melanosome transfer". Br. J. Dermatol. 147 (1): 20–31. doi:10.1046/j.1365-2133.2002.04834.x. PMID 12100180.

[8] Navarrete-Solís J; Castanedo-Cázares JP; Torres-Álvarez B et al. (July 2011). "A Double-Blind, Randomized Clinical Trial of Niacinamide 4% versus Hydroquinone 4% in the Treatment of Melasma". Dermatol Res Pract. 2011 (379173): 1. doi:10.1155/2011/379173. PMC 3142702. PMID 21822427.

[9] Andrew James Martin; Andrew Chen; Bonita Choy; Pablo Fernandez Penas; Gary Halliday; Robyn Dalziell; Catriona McKenzie; Richard A Scolyer; Haryana M. Dhillon; Janette L. Vardy; Gaya St George; Nira Chinniah; Diona Damian (2015). "Oral nicotinamide to reduce actinic cancer: A phase 3 double-blind randomized controlled trial.". American Society of Clinical Oncology Annual Meeting, Chicago, 30 May 2015. J Clin Oncol 33, 2015 (suppl; abstr 9000).

[10] Tallman JF, Paul SM, Skolnick P, Gallager DW (1980). "Receptors for the age of anxiety: pharmacology of the benzodiazepines". Science 207 (4428): 274–81. doi:10.1126/science.6101294. PMID 6101294.

[11] Paul, SM; Marangos, PJ; Skolnick, P; Goodwin, FK (1982). "Biological substrates of anxiety: benzodiazepine receptors and endogenous ligands.". L'Encephale 8 (2): 131–44. PMID 6125374.

[12] Akhundov, RA; Sultanov, AA; Gadzhily, RA; Sadykhov, RV (May 1993). "[Psychoregulating role of nicotinamide].". Biulleten' eksperimental'noi biologii i meditsiny 115 (5): 487–91. PMID 7913840.

[13] Green KN, Steffan JS, Martinez-Coria H, Sun X, Schreiber SS, Thompson LM, LaFerla FM (2008-11-05). "Journal of Neuroscience - Nicotinamide Restores Cognition in Alzheimer's Disease Transgenic Mice via a Mechanism Involving Sirtuin Inhibition and Selective Reduction of Thr231-Phosphotau". Retrieved 2008-11-05. .

[14] Safety Study of Nicotinamide to Treat Alzheimer's Disease, clinicaltrials.gov

[15] Definition of niacinamide, National Cancer Institute

[16] Efficacy of BSI-201, a poly (ADP-ribose) polymerase-1 (PARP1) inhibitor, in combination with gemcitabine/carboplatin (G/C) in patients with metastatic triple-negative breast cancer (TNBC): Results of a randomized phase II trial.

[17] Intravenously administered vitamin C as cancer therapy: three cases

[18] Damian DL, Patterson CR, Stapelberg M, Park J, Barnetson RS, Halliday GM (February 2008). "UV radiation-induced immunosuppression is greater in men and prevented by topical nicotinamide". J. Invest. Dermatol. 128 (2): 447–54. doi:10.1038/sj.jid.5701058. PMID 17882270.

[19] Bhansali SG, Brazeau DA, Sonee M, Mukherjee SK. (2006). Nicotinamide prevents apoptosis in human cortical neuronal cells. Toxicol Mech Methods 16(4):173-180. doi: 10.1080/15376520500194726. PMID 20021043

[20] Crowley CL, Payne CM, Bernstein H, Bernstein C, Roe D. (2000). The NAD+ precursors, nicotinic acid and nicotinamide protect cells against apoptosis induced by a multiple stress inducer, deoxycholate. Cell Death Differ 7(3):314-326. PMID 10745276

[21] Fukuwatari T, Shibata K, Ishihara K, Fushiki T, Sugimoto E (April 2001). "Elevation of blood NAD level after moderate exercise in young women and mice". J. Nutr. Sci. Vitaminol. 47 (2): 177–9. doi:10.3177/jnsv.47.177. PMID 11508711.

[22] 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.

[ib29-23] British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 4 February 2010.

[jp15-24] "Japanese Pharmacopoeia, Fifteenth Edition" (PDF). 2006. Retrieved 4 February 2010.

匿名

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案内

案内

nicotinamide