| Revision as of 09:48, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Saving copy of the {{chembox}} taken from revid 474177210 of page Sinistrin for the Chem/Drugbox validation project (updated: 'DrugBank', 'UNII', 'CASNo'). |
Latest revision as of 07:18, 11 March 2024 edit 2a02:a473:fe0c:1:9ba2:9992:f55a:2599 (talk) →Medical |
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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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| verifiedrevid = 477858029 |
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| ImageFile = Sinistrin.svg |
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| ImageFile = Sinistrin.svg |
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| ImageCaption = Example chemical structure of sinistrin |
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| ImageCaption = Example chemical structure of sinistrin |
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| OtherNames = {{bulletedlist|Polyfructosan|Polyfructosan-S|Inulin analogue|Inutest}} |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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Polyfructosan |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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* Polyfructosan-S |
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| DrugBank = DB00638 |
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* Inulin analogue |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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* Inutest |
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| UNII = Y83V3FE29B |
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| Section1 = {{Chembox Identifiers |
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| PubChem = |
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| DrugBank = <!-- blanked - oldvalue: DB00638 --> |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| UNII = <!-- blanked - oldvalue: JOS53KRJ01 --> |
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| PubChem = |
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| ChEMBL = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChEMBL = |
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| CASNo = <!-- blanked - oldvalue: 37311-25-4 --> |
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| CASNo = 37311-25-4 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = NA |
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| ChemSpiderID = none |
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| ATC-Code = {{ATC|V04|CH01}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = (C<sub>6</sub>H<sub>10</sub>O<sub>6</sub>)<sub>n</sub> |
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| Formula = (C<sub>6</sub>H<sub>10</sub>O<sub>6</sub>)<sub>n</sub> |
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| MolarMass= Variable |
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| Solubility= |
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| Solubility= Good<ref name="Hoppe-Seyler"/> |
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| SolubleOther = Insoluble<ref name="Schmiedeberg">{{cite journal | author = O. Schmiedeberg | url = http://plosjournal.deepdyve.com/lp/de-gruyter/ueber-ein-neues-kohlehydrat-2045AvXaH0 | title = Ueber ein neues Kohlehydrat | journal = Hoppe-Seyler's Zeitschrift für physiologische Chemie | volume = 3 | issue = 1–2 | date = 1879 | pages = 112–133 | doi = 10.1515/bchm1.1879.3.1-2.112 }}</ref> |
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good in water<ref name="Hoppe-Seyler"/> |
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| Solvent = ] |
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* not soluble in ]<ref name="Schmiedeberg">O. Schmiedeberg: '''' Hoppe-Seyler´s Zeitschrift für physiologische Chemie, Band 3 (1-2), 1879. {{doi|10.1515/bchm1.1879.3.1-2.112}}.</ref> |
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| BoilingPt= <!-- 160–170 °C<ref name="Hoppe-Seyler"/> This boiling point is dubious. Should it be the melting point? --> |
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| BoilingPt= <!-- 160–170 °C<ref name="Hoppe-Seyler"/> This boiling point is dubious. Should it be the melting point? --> |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = V04 |
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| ATCCode_suffix = CH01 |
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'''Sinistrin''' is a naturally occurring sugar polymer or ], also known as polyfructosane. It belongs to the ] group, like inulin. As it is the case with similar substances, such as fructans or ], sinistrin acts as an energy storage molecule in plants. |
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== Discovery, history, and manufacture == |
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In 1879, ] isolated sinistrin from the bulb of the ] (''Urginea maritima'').<ref name="Schmiedeberg"/><ref name="r8">''Biopolymers, Polysaccharides II'', Wiley-VCH, 2002, {{ISBN|3-527-30227-1}}.</ref> He named the substance ’sinistrin’, from the Latin word 'sinister' for left, according to its ] activities. in 1885, Hammarsten found sinistrin in ]s of '']''.<ref name="Hoppe-Seyler">M. Geldmacher-Mallinckrodt und F. May: '''' Hoppe-Seyler's Zeitschrift für physiologische Chemie. Band 307, Heft 1-2, S. 191–201, ISSN (Online) 1437-4315, ISSN (Print) 0018-4888. {{doi|10.1515/bchm2.1957.307.1-2.191}}.</ref> |
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Today sinistrin is industrially manufactured out of the bulb of red squill by various extraction and purification steps.{{cn|date=April 2022}} In 2018, the French pharmacovigilance agency withdrew sinistrin-based products from the market after some patients experienced hypersensitivity reactions including a fatal outcome.<ref name="Bui">Bui TV, Prot-Bertoye C, Ayari H, Baron S, Bertocchio JP, Bureau C, Davis P, Blanchard A, Houillier P, Prie D, Lillo-Le Louet A, Courbebaisse M. Safety of Inulin and Sinistrin: Combining Several Sources for Pharmacovigilance Purposes. Front Pharmacol. 2021 Nov 18;12:725417.{{doi|10.3389/fphar.2021.725417}}.</ref> |
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==Biochemistry== |
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Sinistrin is an inulin-type β–<small>D</small>-fructan with branches on position 6. It belongs to the group of ]s and is partly counted among the ]s (''FOS'').<ref name="r8"/><ref name="r2">E. Nitsch, W. Iwanov und K. Lederer: ''Molecular characterization of Sinistrin''. Carbohydrate Research 72 (1979) 1-12.</ref> Sinistrin is composed out of ] units (97%) and ] units (3%, approximately), building a chain of fructose molecules with a terminal glucose unit. The ] (dp) of sinistrin is in average at 15, the molecular weight is at 3500 ] with a range from 2000 to 6000 Da.<ref name="r8"/><ref name="r3">T. Spies, W. Praznik, A. Hofinger, F. Altmann, E. Nitsch, R. Wutka: ''Carbohydr. Res.'' 235 (1992) 221–230.</ref> The main differences between sinistrin and inulin are the higher alkali-resistance and the better water solubility (even in cold water) of sinistrin compared to inulin. |
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==Uses== |
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===Medical=== |
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Like ], the polymer sinistrin is not metabolized in human blood and passes the kidneys unchanged. Both inulin and sinistrin are therefore frequently used for the diagnosis of ]s. An important measure of kidney function is the ] (GFR). GFR is the volume of fluid filtered from the renal (kidney) ] capillaries into the ] per time unit.<ref>{{cite book| title= Essentials of Human Physiology| first= Thomas M. |last= Nosek| chapter=Section 7/7ch04/7ch04p11 |chapter-url=http://humanphysiology.tuars.com/program/section7/7ch04/7ch04p11.htm |archive-url=https://web.archive.org/web/20160324124828/http://humanphysiology.tuars.com/program/section7/7ch04/7ch04p11.htm|archive-date=2016-03-24}} - "Glomerular Filtration Rate"</ref> To measure this parameter, a marker substance is injected into the blood stream, and its rate of excretion in urine is compared to the plasma concentration. Such a marker substance needs to be non-toxic, not ] in the circulation, neither reabsorbed nor secreted in the kidney, and measurable. |
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The measurement of the sinistrin-] is used to exactly determine the GFR in humans.<ref name="r5">B. Watschinger und I. Kobinger: ''Wiener Zeitschrift für Innere Medizin'' 45 (1964) 219-228.</ref><ref name="r6">T. Buclin, A. Pechere-Bertschi, R. Sechaud et al.: ''Sinistrin clearance for determination of glomerular filtration rate: a reappraisal of various approaches using a new analytical method''. J Clin Pharmacol 1997;37:679–92. 204–211.</ref> The assays to determine sinistrin in urine or plasma are identical to that used for inulin. However, sinistrin is often preferred to the alternative, inulin, because it is highly soluble in water and easier to handle. For the application as a renal diagnostic an aqueous solution of sinistrin is approved under the trade name „Inutest“.<ref> bei pharmazie.com, accessed on June 7th 2011.</ref> |
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==Notes== |
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{{reflist}} |
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==References== |
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* D.P. Mertz und H. Sarre: ''Polyfructosan-S: Eine neue inulinartige Substanz zur Bestimmung des Glomerulusfiltrates und des physiologisch aktiven extracellulären Flüssigkeitsvolumens beim Menschen''. Klin Wochenschrift 1963;41:868-72. |
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{{Carbohydrates}} |
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{{Diagnostic agents}} |
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] |
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] |