Mechanistic insights of the controlled release capacity of polar functional group in transdermal drug delivery system: the relationship of hydrogen bonding strength and controlled release capacity was written by Zheng, Luoy;Chao, Liuy;Quan, Peng;Yang, Degong;Zhao, Hanqing;Wan, Xiaocao;Fang, Liang. And the article was included in Acta Pharmaceutica Sinica B in 2020.Name: (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one This article mentions the following:
Hydrogen bonding interaction was considered to play a critical role in controlling drug release from transdermal patch. However, the quant. evaluation of hydrogen bonding strength between drug and polar functional group was rarely reported, and the relationship between hydrogen bonding strength and controlled release capacity of pressure sensitive adhesive (PSA) was not well understood. The present study shed light on this relationship. Acrylate PSAs with amide group were synthesized by a free radical-initiated solution polymerization Six drugs, i.e., etodolac, ketoprofen, gemfibrozil, zolmitriptan, propranolol and lidocaine, were selected as model drugs. In vitro drug release and skin permeation experiments and in vivo pharmacokinetic experiment were performed. Partial correlation anal., fourier-transform IR spectroscopy and mol. simulation were conducted to provide mol. details of drug-PSA interactions. Mech. test, rheol. study, and modulated differential scanning calorimetry study were performed to scrutinize the free volume and mol. mobility of PSAs. Release rate of all six drugs from amide PSAs decreased with the increase of amide group concentrations; however, only zolmitriptan and propranolol showed decreased skin permeation rate. It was found that drug release was controlled by amide group through hydrogen bonding, and controlled release extent was pos. correlated with hydrogen bonding strength. From these results, we concluded that drugs with strong hydrogen bond forming ability and high skin permeation were suitable to use amide PSAs to regulate their release rate from patch. In the experiment, the researchers used many compounds, for example, (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one (cas: 139264-17-8Name: (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one).
(S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one (cas: 139264-17-8) belongs to oxazolidine derivatives. Oxazolidines are commonly obtained by reaction of strained heterocycles, mainly aziridines. Oxazolidines are well known as key portions of bioactive molecules or precursors of chiral molecules, as well as established chiral auxiliaries.Name: (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem