Egyszerű nézet

dc.contributor.author Fejős, Ida
dc.contributor.author He Y
dc.contributor.author Völgyi, Gergely
dc.contributor.author Kazsoki, Adrienn
dc.contributor.author Sun J
dc.contributor.author Chen W
dc.contributor.author Sohajda, Tamás
dc.contributor.author Szente, Lajos
dc.contributor.author Jiang X
dc.contributor.author Béni, Szabolcs
dc.date.accessioned 2014-11-24T19:35:16Z
dc.date.available 2014-11-24T19:35:16Z
dc.date.issued 2014
dc.identifier 84887399226
dc.identifier.citation pagination=594-601; journalVolume=88; journalTitle=JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS;
dc.identifier.uri http://repo.lib.semmelweis.hu//handle/123456789/582
dc.identifier.uri doi:10.1016/j.jpba.2013.10.005
dc.description.abstract The complete physico-chemical characterization of the single enantiomer analgesic drug R,R-tapentadol was quantitated in terms of protonation macro- and microconstants and octanol-water partition coefficient using pH-potentiometry, UV-pH and 1H NMR-pH titrations. The protonation macroconstants were found to be logK1=10.59+/-0.01 and logK2=9.44+/-0.01, while the individual basicity of each protonation site was found to be logkO=9.94 and logkN=10.48 for the phenolate and tertiary amine functions, respectively. As a consequence, the zwitterionic form of tapentadol predominates in aqueous solutions. The potential optical impurity (S,S-tapentadol) was synthesized for the first time in a seven-step chiral synthetic procedure. The enantiomers of tapentadol were separated by cyclodextrin modified capillary zone electrophoresis. Over 15 cyclodextrins were investigated in terms of apparent complex stability and screened as chiral selectors, and the sulfated alpha-cyclodextrin was found to resolve the enantiomers with excellent resolution (Rs=16.2 and 9.1) at pH 4.75 and pH 9.0, respectively. The system containing 12mM selector in a 50mM TRIS-acetate buffer was amenable to detect S,S-tapentadol potential optical impurity at 0.1% concentration level.
dc.relation.ispartof urn:issn:0731-7085
dc.title Tapentadol enantiomers: Synthesis, physico-chemical characterization and cyclodextrin interactions.
dc.type Journal Article
dc.date.updated 2014-11-24T19:34:41Z
dc.language.rfc3066 en
dc.identifier.mtmt 2460892
dc.identifier.wos 000329532800078
dc.identifier.pubmed 24211722
dc.contributor.department SE/GYTK/Gyógyszerészi Kémiai Intézet
dc.contributor.institution Semmelweis Egyetem


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