| Revision as of 05:16, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468550293 of page Allantoin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 08:19, 21 December 2024 edit Preimage (talk | contribs)Extended confirmed users1,277 edits →Lede: Clarify: allantoin is not a (major) metabolic intermediate in humans |
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{{redirect2|Paxyl|udder cream|the antidepressant Paxil|Paroxetine|the ointment|Bag Balm}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 443375405 |
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| ImageFile = Allantoin_chemical_structure.png |
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| verifiedrevid = 477317673 |
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| ImageSize = 150px |
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| ImageFile = Allantoin.svg |
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| IUPACName = (2,5-Dioxo-4-imidazolidinyl) urea |
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| ImageSize = 180 |
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| OtherNames = • Alcloxa<br>• Aldioxa<br>• Ureidohydantoin<br>•Glyoxyldiureide<br>•Hemocane<br>• 5-Ureidohydantoin<br>• Vitamin U (formerly)<ref>{{cite book |title=Staying Healthy With Nutrition: The Complete Guide to Diet and Nutritional Medicine |last=Haas |first=Elson M. |year=1992 |publisher=Celestial Arts |isbn=0-89087-481-6 }}</ref> |
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| ImageAlt = Skeletal formula of allantoin |
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| Section1 = {{Chembox Identifiers |
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| ImageFile1 = Allantoïne.JPG |
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| ImageSize1 = 180 |
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| ImageAlt1 = Heap of white powder on a watch glass |
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| ImageFile2 = Allantoin-3D-balls.png |
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| ImageSize2 = 180 |
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| ImageAlt2 = Ball-and-stick model of the allantoin molecule |
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| IUPACName = ''N''-(2,5-Dioxoimidazolidin-4-yl)urea |
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| OtherNames = 1-(2,5-Dioxoimidazolidin-4-yl)urea<br>Glyoxyldiureide<br>5-Ureidohydantoin |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 199 |
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| ChemSpiderID = 199 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 97-59-6 |
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| CASNo = 97-59-6 |
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| PubChem = |
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| PubChem = 204 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15676 |
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| ChEBI = 15676 |
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| SMILES = O=C1NC(=O)NC1NC(=O)N |
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| SMILES = O=C1NC(=O)NC1NC(=O)N |
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| EINECS = 202-592-8 |
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}} |
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| RTECS = YT1600000 |
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| Section2 = {{Chembox Properties |
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}} |
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|C=4|H=6|N=4|O=3 |
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|Section2={{Chembox Properties |
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| C=4 | H=6 | N=4 | O=3 |
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| Appearance = colourless crystalline powder |
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| Appearance = colourless crystalline powder |
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| Density = 1.45g/cm3 |
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| Odor = odorless |
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| Density = 1.45 g/cm<sup>3</sup> |
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| MeltingPtC = 230 |
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| MeltingPtC = 230 |
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| MeltingPt_notes = (decomposes) |
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| BoilingPt = |
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| Solubility = 0.5% at 25 °C |
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| BoilingPtC = 478 |
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| BoilingPt_notes = {{Dubious|Decomposes before melting, then allegedly boils|date=November 2020|reason=Solids that decompose rather than melting rarely have a boiling point. Especially not a boiling point 200 degrees above decomposition.}} |
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}} |
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| Solubility = 0.57 g/100 mL (25 °C) <br /> 4.0 g/100 mL (75 °C) |
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| Section3 = {{Chembox Hazards |
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| SolubleOther = soluble in ], ], ] <br /> insoluble in ] |
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| ExternalMSDS = |
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| LogP = −3.14 |
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| pKa = 8.48 |
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}} |
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|Section3={{Chembox Hazards |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| ExternalSDS = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| LD50 = > 5000 mg/kg (oral, rat) |
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'''Allantoin''' is a chemical compound with formula C<sub>4</sub>H<sub>6</sub>N<sub>4</sub>O<sub>3</sub>. It is also called '''5-ureidohydantoin''' or '''glyoxyldiureide'''.<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=204 | title=Allantoin}}</ref><ref>{{Cite web | url=http://www.chemblink.com/products/97-59-6.htm | title=CAS # 97-59-6, Allantoin, 5-Ureidohydantoin, Glyoxyldiureide, Glyoxylic diureide, Cordianine, Glyoxyldiureid, (2,5-Dioxo-4-imidazolidinyl)urea}}</ref> It is a ] of ]. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria, though not humans. It is produced from ], which itself is a degradation product of ], by action of ] (uricase).<ref>{{Cite journal|last1=Pizzichini|first1=Maria|last2=Pandolfi|first2=Maria Luisa|last3=Arezzini|first3=Laura|last4=Terzuoli|first4=Lucia|last5=Fè|first5=Linda|last6=Bontemps|first6=Francois|last7=Van den Berghe|first7=Georges|last8=Marinello|first8=Enrico|date=1996-08-09|title=Labelling of uric acid and allantoin in different purine organs and urine of the rat|journal=Life Sciences|volume=59|issue=11|pages=893–899|doi=10.1016/0024-3205(96)00387-6|pmid=8795700}}</ref><ref>{{Cite journal|last1=Xi|first1=H.|last2=Schneider|first2=B. L.|last3=Reitzer|first3=L.|date=2000-10-01|title=Purine catabolism in ''Escherichia coli'' and function of xanthine dehydrogenase in purine salvage|journal=Journal of Bacteriology|volume=182|issue=19|pages=5332–5341|issn=0021-9193|pmc=110974|pmid=10986234|doi=10.1128/jb.182.19.5332-5341.2000}}</ref><ref>{{Cite journal|last1=Johnson|first1=Richard J.|last2=Sautin|first2=Yuri Y.|last3=Oliver|first3=William J.|last4=Roncal|first4=Carlos|last5=Mu|first5=Wei|last6=Gabriela Sanchez-Lozada|first6=L.|last7=Rodriguez-Iturbe|first7=Bernardo|last8=Nakagawa|first8=Takahiko|last9=Benner|first9=Steven A.|date=2009-01-01|title=Lessons from comparative physiology: could uric acid represent a physiologic alarm signal gone awry in western society?|journal=Journal of Comparative Physiology B|volume=179|issue=1|pages=67–76|doi=10.1007/s00360-008-0291-7|issn=1432-136X|pmc=2684327|pmid=18649082}}</ref> Allantoin also occurs as a natural mineral compound (] ] Aan<ref>{{Cite journal|last=Warr|first=L.N.|date=2021|title=IMA-CNMNC approved mineral symbols|journal=Mineralogical Magazine|volume=85|issue=3 |pages=291–320|doi=10.1180/mgm.2021.43 |bibcode=2021MinM...85..291W |s2cid=235729616 |doi-access=free}}</ref>). |
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== History == |
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Allantoin was first isolated in 1800 by the Italian physician Michele Francesco Buniva (1761–1834) and the French chemist ], who mistakenly believed it to be present in the ].<ref>See: |
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* Buniva and Vauquelin (1800) (On the amniotic fluid of women and cows), ''Annales de chimie'', '''33''' : 269-282. |
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* See also: Leopold Gmelin with Henry Watts, trans., ''Hand-book of Chemistry'' (London, England: The Cavendish Society, 1856), vol. 10, </ref> In 1821, the French chemist ] found it in the fluid of the ]; he called it ''"l'acide allantoique"''.<ref>Lassaigne (1821) (New investigations into the composition of the allantoic and amniotic fluids of the cow), ''Annales de chimie et de physique'', 2nd series, '''17''' : 295-305. On pp. 300 ff, Lassaigne names and characterizes "l'acide allantoique" (allantoic acid).</ref> In 1837, the German chemists ] and ] synthesized it from ] and renamed it "allantoïn".<ref>See: |
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* Liebig and Wöhler (1837) (On the nature of uric acid), ''Annalen der Physik und Chemie'', '''41''' (8) : 561-569. Allantoin is named on p. 563. ''"Sie sind ''Allantoïssäure'', oder dieselbe Substance, die man in der Allantoïsflussigkeit der Kühe gefunden hat; wir werden sie von nun an ''Allantoïn'' nennen."'' (They are allantois acid, or the same substance that one found in the allantois fluid of cows; we will call it "allantoin" from now on.) |
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* Reprinted in: F. Wöhler and J. Liebig (1838) (Investigations into the nature of uric acid), ''Annalen der Pharmacie'', '''26''' : 241-340.</ref> |
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==Animals== |
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Named after the ] (an ] embryonic excretory organ in which it concentrates during development in most ]s except humans and other hominids), it is a product of oxidation of ] by ] ]. After birth, it is the predominant means by which ] is excreted in the ] of these animals.<ref>{{cite journal |title= The absorption and excretion of allantoin in mammals|author1=Young E. G. |author2=Wentworth H. P. |author3=Hawkins W. W. | journal= J. Pharmacol. Exp. Ther. | volume= 81 | pages= 1–9| year= 1944 | url=http://jpet.aspetjournals.org/cgi/reprint/81/1/1 | issue=1}}</ref> In humans and other higher apes, the metabolic pathway for conversion of ] to allantoin is not present, so the former is excreted. Recombinant ] is sometimes used as a drug to catalyze this metabolic conversion in patients. In fish, allantoin is broken down further (into ]) before excretion.<ref>{{cite journal |last=Fujiwara |first=S |author2=Noguchi T |year=1995|title=Degradation of purines: only ureidoglycollate lyase out of four allantoin-degrading enzymes is present in mammals |journal=The Biochemical Journal |volume=312 |issue=Pt 1 |pages=315–8 |pmid=7492331 |pmc=1136261 |doi=10.1042/bj3120315 }}</ref> |
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Allantoin has been shown to improve insulin resistance when administered to rats and to increase lifespan when administered to the nematode worm '']''.<ref>{{cite journal|author1=Ko, W.C. |author2=Liu, I.M. |author3=Chung, H.H. |author4=Cheng, J.T.|title=Activation of I<sub>2</sub>-imidazoline receptors may ameliorate insulin resistance in fructose-rich chow-fed rats|journal=Neuroscience Letters|volume=448|issue=1|date=2008|pages=90–93|doi=10.1016/j.neulet.2008.10.002|pmid=18926881|s2cid=207127849 }}</ref><ref>{{cite journal|author1=Shaun Calvert |author2=Robi Tacutu |author3=Samim Sharifi |author4=Rute Teixeira |author5=Pratul Ghosh |author6=João Pedro de Magalhães|year=2016|title=A network pharmacology approach reveals new candidate caloric restriction mimetics in ''C. elegans''|journal=Aging Cell|volume=15 |issue=2|pages=256–266|doi= 10.1111/acel.12432|pmid=26676933|pmc=4783339}}</ref> |
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== Bacteria == |
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In bacteria, purines and their derivatives (such as allantoin) are used as secondary sources of nitrogen under nutrient-limiting conditions. Their degradation yields ammonia, which can then be utilized.<ref>{{Cite journal|last1=Ma|first1=Pikyee|last2=Patching|first2=Simon G.|last3=Ivanova|first3=Ekaterina|last4=Baldwin|first4=Jocelyn M.|last5=Sharples|first5=David|last6=Baldwin|first6=Stephen A.|last7=Henderson|first7=Peter J. F.|date=2016-05-01|title=Allantoin transport protein, PucI, from ''Bacillus subtilis'': evolutionary relationships, amplified expression, activity and specificity|journal=Microbiology|volume=162|issue=5|pages=823–836|doi=10.1099/mic.0.000266|doi-access=free |issn=1465-2080|pmc=4851255|pmid=26967546}}</ref> For instance, '']'' is able to utilize allantoin as its sole nitrogen source.<ref>{{Cite journal|last1=Goelzer|first1=Anne|last2=Bekkal Brikci|first2=Fadia|last3=Martin-Verstraete|first3=Isabelle|last4=Noirot|first4=Philippe|last5=Bessières|first5=Philippe|last6=Aymerich|first6=Stéphane|last7=Fromion|first7=Vincent|date=2008-02-26|title=Reconstruction and analysis of the genetic and metabolic regulatory networks of the central metabolism of Bacillus subtilis|journal=BMC Systems Biology|volume=2|pages=20|doi=10.1186/1752-0509-2-20|issn=1752-0509|pmc=2311275|pmid=18302748 |doi-access=free }}</ref> |
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Mutants in the ''B. subtilis'' ''pucI'' gene were unable to grow on allantoin, indicating that it encodes an allantoin transporter.<ref>{{Cite journal|last1=Schultz|first1=A. C.|last2=Nygaard|first2=P.|last3=Saxild|first3=H. H.|date=2001-06-01|title=Functional analysis of 14 genes that constitute the purine catabolic pathway in ''Bacillus subtilis'' and evidence for a novel regulon controlled by the PucR transcription activator|journal=Journal of Bacteriology|volume=183|issue=11|pages=3293–3302|doi=10.1128/JB.183.11.3293-3302.2001|issn=0021-9193|pmc=99626|pmid=11344136}}</ref> |
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In '']'', allantoinase (] 3.5.2.5) and allantoicase (EC 3.5.3.4) are essential for allantoin metabolism. In this species the catabolism of allantoin, and the subsequent release of ammonium, inhibits antibiotic production (''Streptomyces'' species synthesize about half of all known antibiotics of microbial origin).<ref>{{Cite journal|last1=Navone|first1=Laura|last2=Casati|first2=Paula|last3=Licona-Cassani|first3=Cuauhtémoc|last4=Marcellin|first4=Esteban|last5=Nielsen|first5=Lars K.|last6=Rodriguez|first6=Eduardo|last7=Gramajo|first7=Hugo|date=2013-11-29|title=Allantoin catabolism influences the production of antibiotics in ''Streptomyces coelicolor''|journal=Applied Microbiology and Biotechnology|language=en|volume=98|issue=1|pages=351–360|doi=10.1007/s00253-013-5372-1|issn=0175-7598|pmid=24292080|hdl=11336/7859|s2cid=216898|hdl-access=free}}</ref> |
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== Applications == |
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Allantoin is present in botanical ]s of the ] plant and in the ] 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 ] and ] requirements. Over 10,000 ]s reference allantoin.<ref>{{Dead link|date=May 2019 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> |
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===Cosmetics=== |
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Manufacturers may use allantoin as an ingredient in over-the-counter cosmetics.{{cn|date=March 2023}} |
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===Pharmaceuticals=== |
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It is frequently present in ], ], and other ] products, in ]s, ]s, anti-acne products, sun care products, and clarifying lotions, various cosmetic lotions and creams, and other cosmetic and pharmaceutical products.<ref>{{cite journal |doi=10.1111/j.1524-4725.2005.31734 |last=Thornfeldt |first=C |year=2005|title=Cosmeceuticals containing herbs: fact, fiction, and future |journal=Dermatologic Surgery |volume=31 |issue=7 Pt 2 |pages=873–80 |pmid=16029681 }}</ref> |
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===Biomarker of oxidative stress=== |
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Since ] is the end product of the ] in humans, only non-enzymatic processes with ] will give rise to allantoin, which is thus a suitable ] to measure ] in chronic illnesses and ].<ref>{{cite journal|vauthors=Kanďár R, Záková P |pmid=18636793|year=2008|title=Allantoin as a marker of oxidative stress in human erythrocytes|volume=46|issue=9|pages=1270–4|doi=10.1515/CCLM.2008.244|journal=Clinical Chemistry and Laboratory Medicine|s2cid=6420729}}</ref><ref>{{cite journal|vauthors=Zitnanová I, Korytár P, Aruoma OI, Sustrová M, Garaiová I, Muchová J, Kalnovicová T, Pueschel S, Duracková Z |pmid=14967170|year=2004|title=Uric acid and allantoin levels in Down syndrome: Antioxidant and oxidative stress mechanisms?|volume=341|issue=1–2|pages=139–46|doi=10.1016/j.cccn.2003.11.020|journal=Clinica Chimica Acta}}</ref> |
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== See also == |
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{{Portal|Biology|Medicine|Chemistry}} |
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* ] and ], are ] condensation products of allantoin with ]. |
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== References == |
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{{reflist}} |
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== External links == |
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* '']'' (AllB) in ] () |
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