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  • Synthesis and transdermal permeation-enhancing activity of ketone, amide, and alkane analogs of Transkarbam 12.

Synthesis and transdermal permeation-enhancing activity of ketone, amide, and alkane analogs of Transkarbam 12.

Bioorganic & medicinal chemistry (2005-12-27)
Tomás Holas, Katerina Vávrová, Jana Klimentová, Alexandr Hrabálek
ABSTRACT

Transkarbam 12 (5-(dodecyloxycarbonyl)pentylammonium-5-(dodecyloxycarbonyl)pentylcarbamate, T12) is a highly active transdermal permeation enhancer. In this study, ketone, amide, and alkane analogs of T12 have been synthesized and evaluated for their permeation-enhancing activity using porcine skin and theophylline as a model drug. Replacement of ester by methylene and ketone, respectively, led to a significant decrease of activity. Amide analogs displayed lower activity in 60% propylene glycol and were comparable to T12 in isopropyl myristate. An intramolecular H-bond between ester and ammonium-carbamate group was suggested to be important for the permeation-enhancing activity of T12.

MATERIALS
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Sigma-Aldrich
6-Bromohexanoyl chloride, 97%