Revision as of 12:02, 23 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456723306 of page Lisofylline for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 01:35, 4 December 2023 edit Buidhe (talk | contribs)Autopatrolled, Extended confirmed users, Page movers, File movers, Mass message senders, New page reviewers, Pending changes reviewers, Template editors136,059 edits added Category:Anti-interleukin drugs using HotCat |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Infobox drug |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 462092166 |
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| verifiedrevid = 411545702 |
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| IUPAC_name = 1--3,7-dimethyl-3,7-dihydro-1''H''-purine-2,6-dione |
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| IUPAC_name = 1--3,7-dimethyl-3,7-dihydro-1''H''-purine-2,6-dione |
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| image = lisofylline.svg |
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| image = lisofylline.svg |
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| alt = |
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| alt = Skeletal formula of lisofylline |
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| image2 = Lisofylline 3D spacefill.png |
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| alt2 = Space-filling model of the lisofylline molecule |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 100324-81-0 --> |
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| CAS_number = 100324-81-0 |
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| ATCvet = |
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| ATCvet = |
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| ATC_prefix = <!-- 'none' if uncategorised --> |
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| ATC_prefix = <!-- 'none' if uncategorised --> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 438549 |
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| ChemSpiderID = 438549 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = L1F2Q2X956 |
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| UNII = L1F2Q2X956 |
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| ChEBI = 143527 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1411 |
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| ChEMBL = 1411 |
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| synonyms = 1-(5-Hydroxyhexyl)-3,7-dimethylxanthine (HDX) |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=13 | H=20 | N=4 | O=3 |
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| C=13 | H=20 | N=4 | O=3 |
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| molecular_weight = 280.32 g/mol |
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| smiles = O=C2N(c1ncn(c1C(=O)N2CCCC(O)C)C)C |
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| smiles = O=C2N(c1ncn(c1C(=O)N2CCCC(O)C)C)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NSMXQKNUPPXBRG-SECBINFHSA-N |
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| StdInChIKey = NSMXQKNUPPXBRG-SECBINFHSA-N |
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}} |
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}} |
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'''Lisofylline''' (LSF) is a synthetic small molecule with novel anti-] properties. LSF can effectively prevent ] in preclinical models and improves the function and viability of isolated or transplanted ] islets. It is a ] of ]. |
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As well, LSF improves cellular ]l function and blocks ] (IL-12) signaling and ] activation in target cells and tissues. IL-12 and STAT-4 activation are important pathways linked to inflammation and autoimmune damage to ] producing cells. Therefore, LSF and related analogs could provide a new therapeutic approach to prevent or reverse ]. LSF also directly reduces ]-induced changes in human kidney cells suggesting that LSF and analogs have the potential to treat the complications associated with diabetes. |
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==Synthesis== |
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The ''R'' enantiomer of the pentoxyfylline analogue in which the ketone has been reduced to an alcohol shows enhanced activity as an inhibitor of ] over the parent drug. |
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] |
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For analogs see:<ref>{{cite journal | vauthors = Cui P, Macdonald TL, Chen M, Nadler JL | title = Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes | journal = Bioorganic & Medicinal Chemistry Letters | volume = 16 | issue = 13 | pages = 3401–5 | date = July 2006 | pmid = 16650991 | doi = 10.1016/j.bmcl.2006.04.036 }}</ref> |
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==Further reading== |
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*{{Cite patent|country=DE|number=3942872|title=Verfahren zur enantioselektiven Darstellung von (ω-1)-Hydroxyalkylxanthinen |pubdate=1991-06-27 |
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|assign=]|inventor1-last=Aretz |inventor1-first=Werner|inventor2-last=Furrer |inventor2-first=Harald|inventor3-last=Gebert |inventor3-first=Ulrich|inventor4-last=Hinze |inventor4-first=Heinz-Joachim}} |
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*{{cite patent|country=US|number=5310666|title=Process for the enantioselective preparation of (β-1)-hydroxyalkylxanthines by reduction using ''Rhodotorula rubra''|pubdate=1994-05-10|assign=]|inventor1-last=Aretz |inventor1-first=Werner|inventor2-last=Furrer |inventor2-first=Harald|inventor3-last=Gebert |inventor3-first=Ulrich|inventor4-last=Hinze |inventor4-first=Heinz-Joachim}} |
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*{{Cite patent|country=WO|number=9531450|title=Asymmetric synthesis of chiral secondary alcohols|pubdate=1995-11-23|assign=Cell Therapeutics Inc.|inventor1-last=Klein |inventor1-first=J. Peter|inventor2-last=Leigh |inventor2-first=Alistair J.|inventor3-last=Michnick |inventor3-first=John|inventor4=KUMAR ANIL M.; UNDERINER GAIL E.}} |
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== References == |
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{{reflist}} |
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== External links == |
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