Synthesis and transdermal penetration-enhancing activity of carbonic and carbamic acid esters—Comparison with transkarbam 12

Series of carbamic and carbonic acid esters has been prepared as analogues of transkarbam 12 and their transdermal penetration-enhancing activity has been evaluated in vitro. Transkarbam 12 (T12) is a novel transdermal penetration enhancer with high activity. Its polar head group is formed by carbam...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2006-04, Vol.16 (7), p.1981-1984
Main Authors: Klimentová, Jana, Hrabálek, Alexandr, Vávrová, Kateřina, Holas, Tomáš, Kroutil, Aleš
Format: Article
Language:English
Subjects:
Administration, Cutaneous
Animals
Biological and medical sciences
Carbamate
Carbamates - chemical synthesis
Carbamates - chemistry
Carbamates - pharmacology
Carbon dioxide
Carbonate
Carbonic Acid - chemical synthesis
Carbonic Acid - chemistry
Carbonic Acid - pharmacology
Chromatography, High Pressure Liquid
Esters
General pharmacology
Medical sciences
Penetration enhancers
Percutaneous absorption
Permeability
Pharmaceutical technology. Pharmaceutical industry
Pharmacology. Drug treatments
Rats
Swine
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Summary:Series of carbamic and carbonic acid esters has been prepared as analogues of transkarbam 12 and their transdermal penetration-enhancing activity has been evaluated in vitro. Transkarbam 12 (T12) is a novel transdermal penetration enhancer with high activity. Its polar head group is formed by carbamic acid salt that is unstable in acidic environment and releases CO 2. To find out whether this property influences its high activity, two series of compounds with CO 2 stronger bound in the polar head have been prepared—carbonic and carbamic acid esters. The carbamate salt in the polar head was found to be essential for the enhancing activity and its decomposition in an acidic environment suggested relating to the mode of action of T12.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.12.086