A molecular mechanism investigation of the transdermal/topical absorption classification system on the basis of drug skin permeation and skin retention was written by Tian, Qi;Quan, Peng;Fang, Liang;Xu, Hui;Liu, Chao. And the article was included in International Journal of Pharmaceutics (Amsterdam, Netherlands) in 2021.Category: oxazolidine This article mentions the following:
A transdermal/topical absorption classification system for the characterization of the systemic or local delivery of drugs is the theor. basis for the design and evaluation of transdermal/topical formulations. A classification system was established on the basis of the in vitro and in vivo skin permeation/retention behaviors of 12 model drugs. Drug skin penetration/retention exhibited a significant correlation with physicochem. parameters (log KO/W, mol. weight, polar surface area, and polarizability). Four representative model drugs were selected to clarify the mol. mechanisms of drug skin permeation/retention behaviors. The excellent lipid-disrupting effect and enhanced partitioning exhibited by propranolol (high permeation-high retention) and zolmitriptan (high permeation-low retention) via the formation of moderate H-bonds with skin lipids were proven by ATR-FTIR (ΔνasCH2 > 2 cm-1), Raman spectra (ΔLPP, SPP > 0.2 nm), and X-ray scattering (lipid crystallization) and were supported by 13C NMR results. The low lipid miscibility of zolmitriptan (ΔHzolmitriptan-lipid = 126.92 J/g) caused the low skin retention of this drug. High polarizabiltiy (α = 38.5 x 10-24 cm3) and low H-bond forming capability (EH-bond = 0 kcal/mol) restricted terbinafine (low permeation-high retention) in terms of partitioning (kD-SC = 0.09). Diclofenac (low permeation-low retention) stabilized skin lipids through the formation of strong H-bonds and exhibited excessive drug-lipid miscibility (ΔHdiclofenac-skin = -128.73 J/g), thus restricting its skin absorption. This classification system reflects the most essential drug skin absorption characteristics and provides a theor. basis for the design of transdermal/topical formulations. 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: 139264-17-8Category: oxazolidine).
(S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one (cas: 139264-17-8) belongs to oxazolidine derivatives. Oxazolidine-based compounds have started to attract attention also in the medicinal and materials chemistry fields. Some reports highlighted again the effectiveness of oxazolidine-based compounds in driving the stereo- or diastereotopic outcome of chemical reactions.Category: oxazolidine
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem