Synthesis and evaluation of N-acetylprolinate esters — novel skin penetration enhancers

Tenjarla, Srini; Kasina, Ram; Puranajoti, Porranee; Omar, Mehboob S.; Harris, Wayne T.

doi:10.1016/s0378-5173(99)00300-2

Cited by 55 publications

(34 citation statements)

References 10 publications

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“…Saturated drug solutions in propylene glycol with or without enhancers (5% (w/v)) have been used as the donor phase [9] and the enhancement ratios for permeability coefficients were reported (Table 3). …”

Section: C) N-acetylprolinate Estersmentioning

confidence: 99%

“…This could be due to the methods used for skin permeation studies using this enhancer. Unlike other enhancers, HDNAP was not soluble in propylene glycol, and therefore ethanol was used as a cosolvent [9]. Although a different control containing the same amount of ethanol was used for ER calculation, The correlation between log ER (k p ) and log P is:…”

Section: Enhancement Activities Of N-acetylprolinate Esters Towards Hcmentioning

confidence: 99%

“…N-acetylprolinate esters have been synthesized by Tenjarla et al. [9] and have been characterised as novel penetration enhancers.…”

Section: Introductionmentioning

confidence: 99%

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The effect of penetration enhancers on drug delivery through skin: a QSAR study

Ghafourian

Zandasrar

Hamishekar

et al. 2004

Journal of Controlled Release

109

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Skin penetration enhancers are used to allow formulation of transdermal delivery systems for drugs that are otherwise insufficiently skin permeable. A full understanding of the mode of action could be beneficial for the design of potent enhancers and for the choice of the enhancer to be used in topical formulation of a special drug. In this study, the structural requirements of penetration enhancers have been investigated using the Quantitative Structure-Activity Relationship (QSAR) technique. Activities of naturally occurring terpenes, pyrrolidinone and Nacetylprolinate derivatives on the skin penetration of 5-fluorouracil, diclofenac sodium, hydrocortisone, estradiol, and benazepril have been considered. The resulting QSARs indicated that for 5-fluorouracil and diclofenac sodium less hydrophobic enhancers were the most active. More precisely, molecular descriptors in the corresponding QSARs indicated the possible involvement of intermolecular electron donor-acceptor interactions. This was in contrast to the skin permeation promotion of hydrocortisone, estradiol, and benazepril by enhancers, where a linear relationship between enhancement activity and n-octanol/water partition coefficients of enhancers was evident. The possible mechanisms of penetration enhancement as suggested by the QSARs will be discussed.3

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Section: C) N-acetylprolinate Estersmentioning

confidence: 99%

Section: Enhancement Activities Of N-acetylprolinate Esters Towards Hcmentioning

confidence: 99%

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The effect of penetration enhancers on drug delivery through skin: a QSAR study

Ghafourian

Zandasrar

Hamishekar

et al. 2004

Journal of Controlled Release

109

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“…For example, a study by Tenjarla et al found the penetration of corticosteroids was considerably increased in haired skin compared to hairless skin [12]. It has been suggested that the size of a particle determines the depth of follicular penetration [13].…”

Section: Follicular Targeting With Nanoparticlesmentioning

confidence: 99%

Nanotechnology-Based Cosmetics for Hair Care

2015

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Abstract:Hair is a significant indicator of health and can have a major impact on an individual's cosmetic appearance. Research within the cosmetics industry has revealed that when nanomaterials are engineered into hair care, they can enhance the benefits of active ingredients in order to improve hair cosmesis. Within the cosmetics arena, the unique size and intrinsic properties of nanoparticles can be tailored to target the hair follicle and shaft. This review aims to provide an overview of cosmetic nanocarriers that can be employed to improve the appearance of hair.

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“…Also, studies by a number of researchers have shown higher absorption rates in skin areas with higher follicle density (207), (208). Previous studies of the transfollicular route were mostly qualitative and histological studies depended on stain and dye localisation within the hair follicle.…”

Section: Introductionmentioning

confidence: 99%

Targeted skin delivery of topically applied drugs by optimised formulation design

Abd¹

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Early research concentrated on the relationship between a solute's physicochemical properties and its skin permeation, mostly from simple solutions. Relatively less is known about how vehicles, particularly complex ones, might also affect skin permeation by altering the properties of the skin, although this is an area that has attracted much interest. Key requirements for topical delivery is understanding the relationships between drug-vehicle, drug-skin or drug -vehicle -skin interaction. In this project, understanding this relationship was crucial to designing novel formulations able to deliver drugs with different lipophilicity topically or systemically. The first aim was to explore the impact of various solution compositions on skin permeation of some model drugs. I compared in vitro maximum penetration fluxes (Jmax) and solubilities of the vehicles (Sv) and of the stratum corneum (SSC) and derived diffusivities (D*) for four drugs (caffeine, minoxidil, lidocaine and naproxen) having a range of lipophilicities. I used a range of solvent vehicles that were hypothesised to affect the skin to differing degrees to evaluate vehicle effects on permeability parameters.If neither the vehicle nor the solute alters the properties of the skin, maximum (or saturated) solute flux is independent of both the vehicle composition and the solute's saturated solubility in that vehicle. These findings were confirmed in this study for all four drugs used.The permeation of caffeine, minoxidil, lidocaine and naproxen were found to be selectively enhanced by vehicles containing specific excipients that were hypothesised to alter the properties of the skin. The greatest effects were seen on flux and diffusivity by the eucalyptol (EU) and oleic acid (OA) vehicles on the more hydrophilic compounds, caffeine and minoxidil. We concluded that enhanced solute fluxes were mainly driven by increased diffusivity in the stratum corneum.I also examined the extent of skin permeation enhancement of the hydrophilic drug caffeine and lipophilic drug naproxen applied in nanoemulsions incorporating skin penetration enhancers. Infinite doses of fully characterised oil-in-water nanoemulsions containing the skin penetration enhancers oleic acid or eucalyptol as oil phases and caffeine (3%) or naproxen (2%) were applied to full-thickness skin and human epidermal membranes in Franz diffusion cells, along with aqueous control solutions. Caffeine and naproxen fluxes were determined over 8 h. Solute solubility in the formulations and in the stratum corneum, as well as the uptake of product components into the stratum corneum were measured.The nanoemulsions significantly enhanced the skin penetration of caffeine and naproxen compared to aqueous control solutions. The maximum flux enhancement of caffeine was III associated with a synergistic increase in both its solubility in the stratum corneum and skin diffusivity. Enhanced skin penetration in these systems is largely driven by uptake of formulation excipients containing the active compounds into th...

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Synthesis and evaluation of N-acetylprolinate esters — novel skin penetration enhancers

Cited by 55 publications

References 10 publications

The effect of penetration enhancers on drug delivery through skin: a QSAR study

The effect of penetration enhancers on drug delivery through skin: a QSAR study

Nanotechnology-Based Cosmetics for Hair Care

Targeted skin delivery of topically applied drugs by optimised formulation design

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