WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"
any organic compound containing the group -CONH2

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
アミド[基化物]
…の中に;…のまっさい中に

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/02/23 20:47:53」(JST)

wiki en

Nicotinamide, 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] It's produced by the aqueous aminolysis of 3-cyanopyridine (nicotinonitrile) and subsequent crystallization.

Use in medicine[edit]

Skin conditions[edit]

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.

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.^[5] 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 develop any 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]

Anxiety[edit]

Studies show that nicotinamide has anxiolytic (anti-anxiety) properties. It may work in a way similar to benzodiazepines.^[9]^[10]^[11]

Alzheimer's Disease[edit]

It is an activator of sirtuins (but inhibits at higher doses) and has been reported to restore cognition in Alzheimer's disease transgenic mice.^[12] A safety study of niacinamide for the treatment of Alzheimer's disease is currently underway at the University of California, Irvine.^[13]

Cancer[edit]

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.^[14] PARP-1 appears to be an important target for triple negative breast cancers because the cells are sensitive to inhibition of PARP-1.^[15] Niacinamide is also used by some patients in combination with intravenous vitamin C therapy for cancer.^[16] It has also been seen to prevent immunosuppression caused by UVA and UVB radiation (so it could potentially be added to sunscreen).^[17]

Apoptosis[edit]

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,^[18] and in Jurkat (human T-cell lymphoma cells) when oxidative stress is induced by sodium deoxycholate.^[19]

Other[edit]

Nicotinamide reportedly increases the endurance of mice.^[20]

Toxicity[edit]

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.^[21]

Compendial status[edit]

British Pharmacopoeia^[22]
Japanese Pharmacopoeia^[23]

Notes and references[edit]

^ 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. Cite uses deprecated parameters (help)
^ Niren NM (2006). "Pharmacologic doses of nicotinamide in the treatment of inflammatory skin conditions: a review". Cutis 77 (1 Suppl): 11–6. PMID 16871774.
^ http://eloracpharma.com/products/nicazel-forte/
^ 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.
^ 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.
^ 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. 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[edit]

DrugBank.ca Drug Card for Nicotinamide

UpToDate Contents

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1. スタチン系およびフィブラート系以外の薬剤による脂質低下 lipid lowering with drugs other than statins and fibrates
2. 水溶性ビタミンの概要 overview of water soluble vitamins
3. 成人の顔面紅潮に対するアプローチ approach to flushing in adults
4. 高トリグリセリド血症患者に対するアプローチ approach to the patient with hypertriglyceridemia
5. 心血管疾患または糖尿病患者におけるコレステロール低下に関する臨床試験 clinical trials of cholesterol lowering in patients with cardiovascular disease or diabetes

English Journal

The expression of CG9940 affects the adaptation of cardiac function, mobility, and lifespan to exercise in aging Drosophila.

Wen DT1, Zheng L2, Ni L1, Wang H1, Feng Y1, Zhang M1.
Experimental gerontology.Exp Gerontol.2016 Oct;83:6-14. doi: 10.1016/j.exger.2016.07.006. Epub 2016 Jul 19.
The CG9940 gene, which encodes the NAD(+) synthase protein in Drosophila, is conserved in human, zebra fish, and mosquito. NAD(+) synthase is a homodimer, which catalyzes the final step in de novo nicotinamide adenine dinucleotide (NAD(+)) biosynthesis, an amide transfer from either ammonia or gluta
PMID 27448710

Mucous membrane pemphigoid in dogs: a retrospective study of 16 new cases.

Tham HL1, Olivry T1,2, Linder KE2,3, Bizikova P4,5.
Veterinary dermatology.Vet Dermatol.2016 Oct;27(5):376-e94. doi: 10.1111/vde.12344. Epub 2016 Jun 28.
BACKGROUND: Mucous membrane pemphigoid (MMP) is a chronic autoimmune subepidermal blistering disease of dogs, cats and humans.OBJECTIVES: The goal of this study was to describe the clinical, histological and immunological features and treatment outcomes of canine MMP.ANIMALS: Sixteen dogs were diagn
PMID 27353951

1H NMR-Linked Metabolomics Analysis of Liver from a Mouse Model of NP-C1 Disease.

Ruiz-Rodado V1, Nicoli ER2, Probert F1, Smith DA2, Morris L2, Wassif CA2,3, Platt FM2, Grootveld M1.
Journal of proteome research.J Proteome Res.2016 Aug 30. [Epub ahead of print]
Clinical manifestations of Niemann-Pick type C1 (NP-C1) disease include neonatal hepatosplenomegaly and in some patients progressive liver dysfunction and failure. This study involved a 1H NMR-linked metabolomics analysis of liver samples collected from a NP-C1 disease mutant mouse model in order to
PMID 27503774

Japanese Journal

微生物によるビタミン類の製造研究

清水昌
ビタミン 73(12), 713-720, 1999-12-25
… A new optical resolution process for racemic pantolactone, a chiral building block for the commer cial production of D-pantothenic acid, has been developed. … Thus, DL-pantolactone is easily separated into D-pantoic acid and L-pantolactone. … 3-Cyanopyridine, a starting substance for the commercial production of nicotinamide, is also efficiently converted to the corresponding amide, nicotinamide by the enzyme. …
NAID 110002843662

The Effects of Niacin on DNA Repair after N-Methyl-N'-nitro-N-nitrosoguanidine Treatment in Normal Human Lymphocytes

Ogata Shin,Okumura Katsuzumi,Taguchi Hiroshi
Bioscience, biotechnology, and biochemistry 61(12), 2116-2118, 1997-12-23
… When lymphocytes were incubated in culture medium with various concentrations of niacin, incubation of lymphocytes with nicotinic acid at 5μM or nicotin-amide at 10 mM caused a 2-3 fold increase in NAD content. … Under these conditions lymphocytes were treated with N-methyl-N'-nitro-N-nitrosoguanidine (MNNG), Interestingly, the rejoining of DNA strand breaks was promoted by nicotinic acid but nicotinamide inhibited the rejoining. …
NAID 110002678892

キャピラリー電気泳動分析のための電気浸透流による試料の吸引注入法

呉行正 [他],笹木幸司,小林英吾,保母敏行
分析化学 43(8), 609-613, 1994-08-05
キャピラリー電気泳動分析における試料注入法としてよく使用されている電気泳動注入法は, 試料を注入するとき電気浸透流と電気泳動現象を利用するので, 試料の組成を変化させずにそのまま注入することができない.本報告では作製が容易, 操作が簡便なナフィオン膜ジョイントを利用する従来の電気泳動注入法の欠点を改善できる電気浸透流による試料の吸引注入法を報告する.ナフィオン膜ジョイントの使用により, 試料を注入 …
NAID 110002906807

「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
Density	1.4463g/cm3
Melting point	129.5 °C (265.1 °F)
Boiling point	334 °C (633 °F)
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
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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。

「nicotinic」

　　[★]

ニコチン性の、ニコチンの

関: nicotine、nicotine sulfate

[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. Cite uses deprecated parameters (help)

[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] ttp://eloracpharma.com/products/nicazel-forte/

[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] 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.

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

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

[12] 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. .

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

[14] Definition of niacinamide, National Cancer Institute

[15] 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.

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

[17] 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.

[18] 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

[19] 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

[20] 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.

[21] 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.

[ib29-22] British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009". Retrieved 4 February 2010.

[jp15-23] "Japanese Pharmacopoeia, Fifteenth Edition". 2006. Retrieved 4 Februally 2010.

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案内

nicotinic acid amide