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- W2014131719 abstract "The feasibility of providing transdermal delivery of the tripeptide TRH (pGlu-His-Pro-NH2) was examined using the prodrug approach. The prodrugs studied were the N-isobutyloxycarbonyl and N-octyloxycarbonyl derivatives formed by reacting TRH with the appropriate chloroformates at its imidazole moiety. These derivatives are quantitatively converted to TRH by spontaneous or non-specific esterase-catalyzed hydrolysis, but are resistant towards degradation by the TRH-specific pyroglutamyl aminopeptidase serum enzyme. Diffusion experiments in vitro using human skin samples showed that, whereas TRH and N-isobutyloxycarbonyl-TRH did not penetrate the skin to any measurable extent, the N-octyloxycarbonyl derivative showed a high penetrating capacity. By applying this prodrug derivative in an aqueous solution (pH 6.0) at a concentration of 5%, a steady-state flux of 16 μg TRH/h per cm2 was observed while a 5% solution in propylene glycol gave a flux of 3.6 μg TRH/h per cm2. Essentially all of the prodrug penetrated was present in the receptor phase as TRH. The study demonstrates the feasibility of achieving transdermal delivery of TRH based on the favourable skin penetration properties of the N-octyloxycarbonyl-TRH prodrug which in turn are attributed to its combination of high water solubility and lipophilicity." @default.
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- W2014131719 date "1990-12-01" @default.
- W2014131719 modified "2023-09-27" @default.
- W2014131719 title "Prodrugs of peptides. 7. Transdermal delivery of thyrotropin-releasing hormone (TRH) via prodrugs" @default.
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- W2014131719 doi "https://doi.org/10.1016/0378-5173(90)90382-e" @default.
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