関: ニコチン酸アミド nicotinamide、vitamin B3

ビタミンB群の補酵素

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/26 15:02:57」(JST)

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Nicotinamide, also known as niacinamide and nicotinic acid 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 nicotinamide and nicotinic acid are very similar. NAD+ and NADP+ are coenzymes in a wide variety of enzymatic oxidation-reduction reactions.^[3] It's produced by the aqueous aminolysis of 3-cyanopyridine (nicotinonitrile) and subsequent crystallization.

Use in medicine

Skin conditions

Nicotinamide has demonstrated anti-inflammatory actions that may be of benefit to patients with inflammatory skin conditions.^[4] 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.

Nicomide is the name of an acne medication and, in its vitamin supplement form, the most predominant ingredient is 750 mg of nicotinamide, based on this area of research. Also, it is 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.^[5] Nicotinamide acne treatment is also available as Nicotinamide pads and cream.

Nicotinamide is also reported to be an effective skin whitener in topical application.^[6]^[7]

Anxiety

Studies show that nicotinamide has anxiolytic (anti-anxiety) properties. It may work in a way similar to benzodiazepines.^[8]^[9]^[10]

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.^[11] A safety study of niacinamide for the treatment of Alzheimer's disease is currently underway at the University of California, Irvine.^[12]

Cancer

Nicotinamide acts as a chemo- and radio-sensitizing agent by enhancing tumor blood flow, thereby 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.^[13] PARP-1 appears to be an important target for triple negative breast cancers because the cells are sensitive to inhibition of PARP-1.^[14] Niacinamide is also used by some patients in combination with intravenous vitamin C therapy for cancer.^[15] It has also been seen to prevent immunosuppression caused by UVA and UVB radiation (so it could potentially be added to sunscreen).^[16]

Other

Nicotinamide reportedly increases the endurance of mice.^[17]

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.^[18]

Compendial status

British Pharmacopoeia^[19]
Japanese Pharmacopoeia^[20]

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". Trends Biochem. Sci. 32 (1): 12–9. doi:10.1016/j.tibs.2006.11.006. PMID 17161604. Retrieved 2007-12-23.
^ 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). doi:10.1155/2011/379173. PMID 21822427.
^ 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.
^ http://www.ncbi.nlm.nih.gov/pubmed/6125374
^ http://www.ncbi.nlm.nih.gov/pubmed/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.
^ 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. PMID 16596767.
^ British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009". Retrieved 4 February 2010.
^ "Japanese Pharmacopoeia, Fifteenth Edition". 2006. Retrieved 4 Februally 2010.

External links

DrugBank.ca Drug Card for Nicotinamide

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 水疱性類天疱瘡のマネージメントおよび予後 management and prognosis of bullous pemphigoid
2. 1型糖尿病の予防 prevention of type 1 diabetes mellitus
3. シェーグレン・ラルソン症候群 sjogren larsson syndrome
4. 光による老化 photoaging
5. 難治性の尋常性天疱瘡および落葉状天疱瘡のマネージメント management of refractory pemphigus vulgaris and pemphigus foliaceus

English Journal

Radiofrequency ablation suppresses distant tumour growth in a novel rat model of multifocal hepatocellular carcinoma.

Erös de Bethlenfalva-Hora C, Mertens JC, Piguet AC, Kettenbach J, Schmitt J, Terracciano L, Weimann R, Dufour JF, Geier A.Author information *Hepatology, Department of Clinical Research, University of Bern, Bern, Switzerland.AbstractRFA (radiofrequency ablation) is an established therapy for HCC (hepatocellular carcinoma). The multikinase inhibitor sorafenib prolongs survival in advanced HCC. We examined the effects of RFA alone and in combination with sorafenib on a bystanding tumour in a two-tumour rat model of HCC. A total of 80 rats were implanted with two liver tumours and randomized to four treatment groups: vehicle and sham operation (control), sorafenib and sham operation (Sora/Sham), vehicle and RFA (Vh/RFA), and sorafenib and RFA (Sora/RFA) (n=10/group per time point). RFA or sham-operation was performed on the left lobe tumour on day 15. Animals were killed at day 18 and day 30. Non-RFA-targeted right lobe tumours were analysed for angiogenesis, growth factors [HGF (hepatocyte growth factor), EGF (epidermal growth factor) and VEGF (vascular endothelial growth factor)] and infiltrating immune cells (CD3 and CD68). At day 30, the non-RFA-targeted tumours were significantly smaller in all three treatment groups compared with control (Sora/Sham P≤0.0001, Vh/RFA P=0.005 and Sora/RFA P≤0.0001). The smallest tumours were observed in animals treated with a combination of sorafenib and RFA, whereas the size reduction seen in the RFA-only group indicated an RFA-mediated distant suppression of tumour growth. Growth factor measurement revealed transiently decreased EGF levels after RFA (P=0.008), whereas sorafenib treatment decreased HGF levels (P=0.001). MVD (microvessel density) was reduced by sorafenib (P=0.002) despite increased VEGF levels (P≤0.0001). The immune parameters revealed augmented T-cells and IL-10 (interleukin 10) levels in all three treatment groups; sorafenib additionally increased macrophage numbers (P≤0.0001). RFA and sorafenib alone resulted in significant volume reduction of the non-RFA-targeted tumour; this effect was enhanced when both modalities were combined.
Clinical science (London, England : 1979).Clin Sci (Lond).2014 Feb;126(3):243-52. doi: 10.1042/CS20130089.
RFA (radiofrequency ablation) is an established therapy for HCC (hepatocellular carcinoma). The multikinase inhibitor sorafenib prolongs survival in advanced HCC. We examined the effects of RFA alone and in combination with sorafenib on a bystanding tumour in a two-tumour rat model of HCC. A total o
PMID 23822114

Synthesis, spectral characterization and catalytic activity of Co(II) complexes of drugs: crystal structure of Co(II)-trimethoprim complex.

Madhupriya S, Elango KP.Author information Department of Chemistry, Gandhigram Rural Institute, Deemed University, Gandhigram 624 302, India.AbstractNew Co(II) complexes with drugs such as trimethoprim (TMP), cimetidine (CTD), niacinamide (NAM) and ofloxacin (OFL) as ligands were synthesized. The complexes were characterized by analytical analysis, various spectral techniques such as FT-IR, UV-Vis, magnetic measurements and molar conductivity. The magnetic susceptibility results coupled with the electronic spectra suggested a tetrahedral geometry for the complexes. The coordination mode of trimethoprim ligand and geometry of the complex were confirmed by single crystal X-ray studies. In this complex the metal ion possesses a tetrahedral geometry with two nitrogen atom from two TMP ligands and two chloride ions coordinated to it. The catalytic activity of the complexes in aryl-aryl coupling reaction was screened and the results indicated that among the four complexes [Co(OFL)Cl(H2O)] exhibited excellent catalytic activity.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Jan 24;118:337-42. doi: 10.1016/j.saa.2013.08.085. Epub 2013 Aug 29.
New Co(II) complexes with drugs such as trimethoprim (TMP), cimetidine (CTD), niacinamide (NAM) and ofloxacin (OFL) as ligands were synthesized. The complexes were characterized by analytical analysis, various spectral techniques such as FT-IR, UV-Vis, magnetic measurements and molar conductivity. T
PMID 24060479

Hydrosoluble vitamins.

Chawla J1, Kvarnberg D2.Author information 1Department of Neurology, Hines VA Hospital, Hines, IL, USA; Department of Neurology, Loyola University Medical Center, Maywood, IL, USA. Electronic address: Jasvinder.chawla2@va.gov.2Department of Neurology, Loyola University Medical Center, Maywood, IL, USA.AbstractThe hydrosoluble vitamins are a group of organic substances that are required by humans in small amounts to prevent disorders of metabolism. Significant progress has been made in our understanding of the biochemical, physiologic and nutritional aspects of the water-soluble vitamins. Deficiency of these particular vitamins, most commonly due to inadequate nutrition, can result in disorders of the nervous system. Many of these disorders have been successfully prevented in developed countries; however, they are still common in developing countries. Of the hydrosoluble vitamins, the nervous system depends the most on vitamins B and C (ascorbic acid) for proper functioning. The B group vitamins include thiamin (vitamin B1), riboflavin (vitamin B2), niacin or niacinamide (vitamin B3), pantothenic acid (vitamin B5), pyridoxine or pyridoxal (vitamin B6) and cobalamin (vitamin B12). Clinical findings depend upon the deficiency of the underlying vitamin; generally, deficiency symptoms are seen from a combination rather than an isolated vitamin deficiency. True hereditary metabolic disorders and serious deficiency-associated diseases are rare and in general limited to particular geographic regions and high-risk groups. Their recognition is truly important as that determines the appropriate therapeutic management. The general availability of vitamins to practically everyone and several national health programs have saved many lives and prevented complications. However, there has been some apprehension for several decades about how harmless generous dosages of these vitamins are. Overt overdosages can cause vitamin toxicity affecting various body systems including the nervous system. Systemically, vitamin toxicity is associated with nonspecific symptoms, such as nausea, vomiting, diarrhea, and skin rash which are common with any acute or chronic vitamin overdose. At a national level, recommended daily allowances for vitamins become policy statements. Nutrition policy has far reaching implications in the food industry, in agriculture, and in food provision programs. Overall, water-soluble vitamins are complex molecular structures and even today, many areas of vitamin biochemistry still need to be explored. Many readers might be of the opinion that the classic forms of nutritional deficiency diseases have faded into the background of interesting history. This has caused their diverse symptoms to be neglected by most modern physicians since vitamin enrichment of many foods automatically erases them from their consideration in differential diagnosis. Vitamin B12 and folic acid deficiencies are discussed in other chapters.
Handbook of clinical neurology.Handb Clin Neurol.2014;120:891-914. doi: 10.1016/B978-0-7020-4087-0.00059-0.
The hydrosoluble vitamins are a group of organic substances that are required by humans in small amounts to prevent disorders of metabolism. Significant progress has been made in our understanding of the biochemical, physiologic and nutritional aspects of the water-soluble vitamins. Deficiency of th
PMID 24365359

Japanese Journal

Tetracycline and niacinamide control bullous pemphigoid but not pemphigus foliaceus when these conditions coexist

SHIOHARA Junko,YOSHIDA Kanako,HASEGAWA Junichi,UHARA Hisashi,TAKATA Minoru,SAIDA Toshiaki,OYAMA Bungo,HASHIMOTO Takashi
Journal of dermatology 37(7), 657-661, 2010-07-01
NAID 10026637402

プロピオン酸クロベタゾール軟膏外用とニコチン酸アミド内服を試みた水疱性類天疱瘡の2例 (特集水疱症)

柳下幹男,河畑知穂,西島千博 [他]
皮膚科の臨床 51(3), 295-299, 2009-03
NAID 40016535876

Effects of Vitamin A, Vitamin A plus Iron and Multiple Micronutrient-Fortified Seasoning Powder on Preschool Children in a Suburb of Chongqing, China

Chen Ke,Li Ting-Yu,Chen Li [他],QU Ping,LIU You-Xue
Journal of nutritional science and vitaminology 54(6), 440-447, 2008-12
… groups II and III were fortified with vitamin A plus iron and vitamin A plus iron, thiamine, riboflavin, folic acid, niacinamide, zinc and calcium, respectively. …
NAID 110007007841

Related Pictures

★リンクテーブル★

リンク元	「ニコチン酸アミド」「ナイアシンアミド」

「ニコチン酸アミド」

Nicotinamide
	IUPAC name pyridine-3-carboxamide
	Other names 3-pyridinecarboxamide; niacinamide; nicotinamide; nicotinic acid amide; Vitamin PP
Identifiers
CAS number	98-92-0
PubChem	936
ChemSpider	911
UNII	25X51I8RD4
EC number	202-713-4
DrugBank	DB02701
KEGG	D00036
ChEBI	CHEBI:17154
ChEMBL	CHEMBL1140
ATC code	A11HA01
Jmol-3D images	Image 1
	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 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 ;
Properties
Molecular formula	C6H6N2O
Molar mass	122.12 g mol−1
Melting point	128-131 °C
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

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。

「ナイアシンアミド」

　　[★]

英: niacinamide
関: ニコチンアミド、ビタミンB3、ニコチン酸アミド

[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". Trends Biochem. Sci. 32 (1): 12–9. doi:10.1016/j.tibs.2006.11.006. PMID 17161604. Retrieved 2007-12-23.

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

[5] 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.

[6] 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.

[7] 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). doi:10.1155/2011/379173. PMID 21822427.

[8] 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.

[9] ttp://www.ncbi.nlm.nih.gov/pubmed/6125374

[10] ttp://www.ncbi.nlm.nih.gov/pubmed/7913840

[11] 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. .

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

[13] Definition of niacinamide, National Cancer Institute

[14] 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.

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

[16] 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.

[17] 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.

[18] Cosmetic Ingredient Review Expert Panel (2005). "Final report of the safety assessment of niacinamide and niacin". Int. J. Toxicol. 24 Suppl 5: 1–31. PMID 16596767.

[ib29-19] British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009". Retrieved 4 February 2010.

[jp15-20] "Japanese Pharmacopoeia, Fifteenth Edition". 2006. Retrieved 4 Februally 2010.

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案内

niacinamide