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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}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Infobox drug
{{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 462092166
| Watchedfields = changed
| verifiedrevid = 411545702
| IUPAC_name = 1--3,7-dimethyl-3,7-dihydro-1''H''-purine-2,6-dione | IUPAC_name = 1--3,7-dimethyl-3,7-dihydro-1''H''-purine-2,6-dione
| image = lisofylline.svg | image = lisofylline.svg
| alt = | alt = Skeletal formula of lisofylline
| image2 = Lisofylline 3D spacefill.png
| alt2 = Space-filling model of the lisofylline molecule


<!--Clinical data--> <!--Clinical data-->
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 100324-81-0 --> | CAS_number = 100324-81-0
| ATCvet = | ATCvet =
| ATC_prefix = <!-- 'none' if uncategorised --> | ATC_prefix = <!-- 'none' if uncategorised -->
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 438549 | ChemSpiderID = 438549
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L1F2Q2X956 | UNII = L1F2Q2X956
| ChEBI = 143527
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1411 | ChEMBL = 1411
| synonyms = 1-(5-Hydroxyhexyl)-3,7-dimethylxanthine (HDX)


<!--Chemical data--> <!--Chemical data-->
| C=13 | H=20 | N=4 | O=3 | C=13 | H=20 | N=4 | O=3
| molecular_weight = 280.32 g/mol
| smiles = O=C2N(c1ncn(c1C(=O)N2CCCC(O)C)C)C | smiles = O=C2N(c1ncn(c1C(=O)N2CCCC(O)C)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey = NSMXQKNUPPXBRG-SECBINFHSA-N | StdInChIKey = NSMXQKNUPPXBRG-SECBINFHSA-N
}} }}

'''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 ].

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.

==Synthesis==
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.
]

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>

==Further reading==
*{{Cite patent|country=DE|number=3942872|title=Verfahren zur enantioselektiven Darstellung von (ω-1)-Hydroxyalkylxanthinen |pubdate=1991-06-27
|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}}
*{{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}}
*{{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.}}

== References ==
{{reflist}}

== External links ==
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]
]
]