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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/30 20:30:22」(JST)

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Allantoin is a chemical compound with formula C₄H₆N₄O₃. It is also called 5-ureidohydantoin or glyoxyldiureide.^[1]^[2] It is a diureide of glyoxylic acid.^{[citation needed]}

Named after the allantois (an amniote embryonic excretory organ in which it concentrates during development in most mammals except humans and higher apes^[vague]), it is a product of oxidation of uric acid by purine catabolism. After birth, it is the predominant means by which nitrogenous waste is excreted in the urine of these animals.^[3] In humans and higher apes, the metabolic pathway for conversion of uric acid to allantoin is not present, so the former is excreted. Recombinant rasburicase is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ammonia) before excretion.^[4] Allantoin is a major metabolic intermediate in many other organisms including plants and bacteria.

Applications[edit]

Allantoin is present in botanical extracts of the comfrey plant and in the urine of most mammals. Chemically synthesized bulk allantoin, which is chemically equivalent to natural allantoin, is safe, non-toxic, compatible with cosmetic raw materials and meets CTFA and JSCI requirements. Over 10,000 patents reference allantoin.^[5] Manufacturers cite several beneficial effects for allantoin as an active ingredient in over-the-counter cosmetics, including: a moisturizing and keratolytic effect, increasing the water content of the extracellular matrix and enhancing the desquamation of upper layers of dead skin cells, increasing the smoothness of the skin; promoting cell proliferation and wound healing; and a soothing, anti-irritant, and skin protectant effect by forming complexes with irritant and sensitizing agents. A study published in 2009 reported the treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent containing allantoin.^[6]

It is frequently present in toothpaste, mouthwash, and other oral hygiene products, in shampoos, lipsticks, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.^[7]

Since uric acid is the end product of the purine metabolism in humans, only non-enzymatic processes with reactive oxygen species will give rise to allantoin, which is thus a suitable biomarker to measure oxidative stress in chronic illnesses and senescence.^[8]^[9]

References[edit]

^ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204
^ http://www.chemblink.com/products/97-59-6.htm
^ Young E. G., Wentworth H. P., Hawkins W. W. (1944). "The absorption and excretion of allantoin in mammals". J. Pharmacol. Experi. Therapeutics 81 (1): 1–9.
^ Fujiwara, S; Noguchi T (1995). "Degradation of purines: only ureidoglycollate lyase out of four allantoin-degrading enzymes is present in mammals". The Biochemical Journal 312 (Pt 1): 315–8. PMC 1136261. PMID 7492331.
^ Patent Lens search
^ Veraldi, S; De Micheli, P; Schianchi, R; Lunardon, L (2009). "Treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent". Journal of drugs in dermatology : JDD 8 (6): 537–9. PMID 19537379.
^ Thornfeldt, C (2005). "Cosmeceuticals containing herbs: fact, fiction, and future". Dermatologic Surgery 31 (7 Pt 2): 873–80. doi:10.1111/j.1524-4725.2005.31734. PMID 16029681.
^ Kand'ár R, Záková P. (2008). "Allantoin as a marker of oxidative stress in human erythrocytes". Clinical chemistry and laboratory medicine : CCLM / FESCC 46 (9): 1270–4. doi:10.1515/CCLM.2008.244. PMID 18636793.
^ Zitnanová I, Korytár P, Aruoma OI, Sustrová M, Garaiová I, Muchová J, Kalnovicová T, Pueschel S, Duracková Z (2004). "Uric acid and allantoin levels in Down syndrome: Antioxidant and oxidative stress mechanisms?". Clinica chimica acta; international journal of clinical chemistry 341 (1–2): 139–46. doi:10.1016/j.cccn.2003.11.020. PMID 14967170.

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English Journal

Activation of Imidazoline I-2B Receptors by Allantoin to Increase Glucose Uptake into C2C12 Cells.

Chen MF, Yang TT, Yeh LR, Chung HH, Wen YJ, Lee WJ, Cheng JT.SourceDepartment of Nursing and Biotechnology, Chung Hwa University of Medical Technology, Jen-Te, Tainan City, Taiwan.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.Horm Metab Res.2012 Feb 20. [Epub ahead of print]
Allantoin, an active principle of the yam, belongs to the group of guanidinium derivatives and has been reported to lower plasma glucose in diabetic animals. Recent evidence indicates that activation of the imidazoline I2B receptor (I2BR) by guanidinium derivatives also increases glucose uptake; how
PMID 22351479

Rasburicase for the treatment of tumor lysis in hematological malignancies.

Malaguarnera G, Giordano M, Malaguarnera M.SourceDepartment of Internal Medicine & Systemic Pathologies, Ospedale Cannizzaro, Viale Messina, 829-95125 Catania, Italy.
Expert review of hematology.Expert Rev Hematol.2012 Feb;5(1):27-38.
Tumor lysis syndrome (TLS) is a common oncologic emergency in patients with hematological malignancies sensitive to cytotoxic treatment that present a high proliferative rate. High proliferative cancer rate, high sensitivity of cytotoxic treatment and renal failure represent risk factors for develop
PMID 22272702

Japanese Journal

Potassium-oxonateを用いた運動性高尿酸血症の動物モデルに関する検討

清野哲也,坂田洋満,桧垣靖樹
木更津工業高等専門学校紀要 44, 25-32, 2011-02
… Plasma allantoin concentration was suppressed by K-oxonate in both the exercise and control groups. …
NAID 110008005770

サポーティブペリオドンタルセラピー期における塗布用ブラシ一体型一般用歯周病薬の臨床的および細菌学的な効果

犬伏順也,畑中加珠,安田多賀子,成石浩司,大槻秀彦,高柴正悟
日本歯周病学会会誌 52(3), 225-238, 2010-09-03
サポーティブペリオドンタルセラピー(SPT)期における歯周組織の安定には, 定期的な専門的管理に加え, 患者自身の日々のプラークコントロールが重要である。今回我々は, 患者によるプラークコントロールを強化する目的で, 殺菌作用のある塩化セチルピリジニウム, 抗炎症効果のあるグリチルリチン酸二カリウムおよび組織創傷治癒効果をもつアラントインの3種の薬効成分を配合した薬剤をタフトブラシと一体化した塗布 …
NAID 10027096396

「アラントイン」

Allantoin
	IUPAC name (2,5-Dioxo-4-imidazolidinyl) urea
	Other names •Glyoxyldiureide; • 5-Ureidohydantoin
Identifiers
CAS number	97-59-6
PubChem	204
ChemSpider	199
UNII	344S277G0Z
EC number	202-592-8
KEGG	D00121
ChEBI	CHEBI:15676
ChEMBL	CHEMBL593429
RTECS number	YT1600000
Jmol-3D images	Image 1; Image 2
	SMILES O=C1NC(=O)NC1NC(=O)N C1(C(=O)NC(=O)N1)NC(=O)N ;
	InChI InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) ; Key: POJWUDADGALRAB-UHFFFAOYSA-N InChI=1/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11); Key: POJWUDADGALRAB-UHFFFAOYAE ;
Properties
Molecular formula	C4H6N4O3
Molar mass	158.12 g mol−1
Appearance	colourless crystalline powder
Odor	odorless
Density	1.45 g/cm3
Melting point	230 °C; 446 °F; 503 K (decomp.)
Boiling point	478 °C; 892 °F; 751 K
Solubility in water	0.57 g/100 mL (25 °C); 4.0 g/100 mL (75 °C)
Solubility	soluble in alcohol, pyridine, NaOH; insoluble in ethyl ether
log P	-3.14
Acidity (pKa)	8.48
Hazards
MSDS	Allantoin MSDS
NFPA 704	1 2 0
LD50	> 5000 mg/kg (oral, rat)
	(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: allantoin
同: グリオキシルジウレイド glyoxyldiureide、5-ウレイドヒダントイン 5-ureidohydantoin
関

「aluminum chlorohydroxy allantoinate」

　　[★]

クロロヒドロキシアラントイン酸アルミニウム、アルミニウムクロロヒドロキシアラントイネート、アルクロキサ

「dihydroxyaluminum allantoinate」

　　[★] アルジオキサ。ジヒドロキシアルミニウムアラントイナート

[1] ttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204

[2] ttp://www.chemblink.com/products/97-59-6.htm

[3] Young E. G., Wentworth H. P., Hawkins W. W. (1944). "The absorption and excretion of allantoin in mammals". J. Pharmacol. Experi. Therapeutics 81 (1): 1–9.

[4] Fujiwara, S; Noguchi T (1995). "Degradation of purines: only ureidoglycollate lyase out of four allantoin-degrading enzymes is present in mammals". The Biochemical Journal 312 (Pt 1): 315–8. PMC 1136261. PMID 7492331.

[5] Patent Lens search

[6] Veraldi, S; De Micheli, P; Schianchi, R; Lunardon, L (2009). "Treatment of pruritus in mild-to-moderate atopic dermatitis with a topical non-steroidal agent". Journal of drugs in dermatology : JDD 8 (6): 537–9. PMID 19537379.

[7] Thornfeldt, C (2005). "Cosmeceuticals containing herbs: fact, fiction, and future". Dermatologic Surgery 31 (7 Pt 2): 873–80. doi:10.1111/j.1524-4725.2005.31734. PMID 16029681.

[8] Kand'ár R, Záková P. (2008). "Allantoin as a marker of oxidative stress in human erythrocytes". Clinical chemistry and laboratory medicine : CCLM / FESCC 46 (9): 1270–4. doi:10.1515/CCLM.2008.244. PMID 18636793.

[9] Zitnanová I, Korytár P, Aruoma OI, Sustrová M, Garaiová I, Muchová J, Kalnovicová T, Pueschel S, Duracková Z (2004). "Uric acid and allantoin levels in Down syndrome: Antioxidant and oxidative stress mechanisms?". Clinica chimica acta; international journal of clinical chemistry 341 (1–2): 139–46. doi:10.1016/j.cccn.2003.11.020. PMID 14967170.

リンク元	「アラントイン」
拡張検索	「aluminum chlorohydroxy allantoinate」「dihydroxyaluminum allantoinate」

匿名

検索

案内

案内

allantoin