Other Nitrogen-containing Compounds
1-dodecyl-hexahydro-azepin-2-one/2H-Azepin-2-one, 1-dodecylhexahydro-/tranzone/acecloguanosine/1-Dodecylazepan-2-one/Lauocapram/1 dodecylperhydroazepin 2 one/AZONE/N-Dodecyl-e-caprolactam/azon/1-Dodecyl-2-azepanone/1-dodecylhexahydro-2H-azepin-2-one/usafnd-72/Laurocapram/1-N-dodecylazacycloheptan-2-one
404.9±14.0 °C at 760 mmHg
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provides coniferyl ferulate(CAS#:59227-89-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
The aim of the study was to visualize the penetration modifying effect of laurocapram on the delivery of diazepam and codeine across buccal mucosa by MALDI Mass Spectrometry Imaging (MALDI-MSI). A qualitative ex vivo study was carried out by mounting porcine buccal mucosa in Ussing chamber sliders and applying a pre-treatment of phosphate buffered saline (PBS) or a 50% (v/v) laurocapram:ethanol solution apically before incubation for 1 or 3 h with a 0.1 M diazepam or 0.1 M codeine solution. MALDI-MSI analysis was performed on vertical cryo-sections of porcine buccal mucosa. The analysis provided detailed images of the localisation of the drugs, laurocapram and endogenous lipids in the epithelium and connective tissue. While diazepam in the absence of laurocapram was distributed with a steady concentration gradient through the connective tissue, indicating passive diffusion, pre-treatment with laurocapram fundamentally altered the penetration of diazepam through the buccal mucosa. In the presence of laurocapram, the distribution of diazepam was restricted to areas where laurocapram itself was present, in particular in the outer epithelial cell layers and in certain islands in the connective tissue. In contrast, the penetration of codeine was unaffected by the presence of laurocapram in similar experiments. The co-localization of laurocapram and diazepam indicates a reservoir effect, which has previously been found in diffusion experiments in Ussing chambers. The major difference in the penetration of codeine and diazepam through the buccal mucosa in presence of laurocapram was explained by the physicochemical properties of the drugs. Codeine is characterized by being more hydrophilic than diazepam and was partly charged under the given experimental conditions.
Copyright © 2018 Elsevier B.V. All rights reserved.
Buccal drug absorption; Chemical penetration enhancer; Drug delivery; MALDI-MSI; Mass spectrometry imaging, laurocapram, diazepam
Visualization of the penetration modifying mechanism of laurocapram by Mass Spectrometry Imaging in buccal drug delivery.
Handler AM1, Marxen E1, Jacobsen J1, Janfelt C2.
2019 Jan 15
Absorption enhancers are substances used for temporarily increasing a membrane’s permeability (e.g., the skin and mucosa), either by interacting with its components (lipids or proteins) or by increasing the membrane/vehicle partition coefficient. This article presents the results of biophysical and permeability studies performed with Laurocapram and its analogues. As shown, Laurocapram and its analogues present different enhancing efficacies, for most of both hydrophilic and lipophilic substances. The enhancing effect of Laurocapram (Azone) is attributed to different mechanisms, such as insertion of its dodecyl group into the intercellular lipidic bilayer, increase of the motion of the alkylic chains of lipids, and fluidization of the hydrophobic regions of the lamellate structure. Toxicological studies reveal a low toxicity for Laurocapram, and for some derivatives, a relationship exists between toxicity and the number of carbons in the alkylic chain. Very important, when applied to human skin, Laurocapram shows a minimal absorption, being quickly eliminated from circulation. However, although Laurocapram and its derivatives have been shown to provide enhancement, they have not been widely accepted because of their suspected pharmacological activity or questions about their safety.
Chemical enhancers for the absorption of substances through the skin: Laurocapram and its derivatives.
Lopez-Cervantes M1, Marquez-Mejia E, Cazares-Delgadillo J, Quintanar-Guerrero D, Ganem-Quintanar A, Angeles-Anguiano E.
The probability of simultaneous cutaneous exposure to surfactants and penetration enhancers could occur frequently during routine skin treatment. This study ascertains whether pre-exposure of skin to laurocapram would affect the penetration of a model surfactant, sodium lauryl sulfate (SLS). In vitro experiments with human skin were performed to compare the penetration of SLS after pretreatment with (1) different concentrations of laurocapram, (2) after repeated SLS treatments, (3) untreated controls, and (4) water-control. Pre-exposure to laurocapram enhanced penetration of SLS compared to all other treatments (p < 0.05). Since subsequent pre-exposure of skin to laurocapram increased SLS penetration, the chances of an elevated skin irritation reaction at the exposed site may therefore be possible. Pre-exposure of the skin with SLS did not increase the SLS flux values significantly, compared to the laurocapram pretreated skin. From these results it can be proposed that proper care and precautions may be necessary after exposure of skin to laurocapram and also to various other percutaneous enhancers. Further in vivo correlations are essential to define the clinical implications of this study, especially as related to irritant dermatitis.
Effect of topical laurocapram (Azone) on the in vitro percutaneous permeation of sodium lauryl sulfate using human skin.
Szolar-Platzer C1, Patil S, Maibach HI.