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

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.[1]

References

  1. Synthesis and transdermal permeation-enhancing activity of ketone, amide, and alkane analogs of Transkarbam 12. Holas, T., Vávrová, K., Klimentová, J., Hrabálek, A. Bioorg. Med. Chem. (2006) [Pubmed]
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