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Meier-Davis et al., J Pharm Drug Deliv Res 2012, 1:1
http://dx.doi.org/10.4172/2325-9604.1000102
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Technology and Medicine
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Journal of Pharmaceutics &
Drug Delivery Research
Enhancing the Skin Flux of
Tolnaftate Utilizing the Novel
Excipient, Dodecyl-2-N,N-
Dimethylaminopropionate
(DDAIP)
Susan R. Meier-Davis
1
*, Salma Debar
1
, Richard Martin
1
,
Mohamed Hachicha
1
and Bassam Damaj
1
Abstract
Penetration of drug through the stratum corneum to reach
the underlying epidermal and dermal layers is a critical step for
effective therapy by the topical route. To enhance permeation,
various penetration enhancers have been utilized in combination
with active drugs. The novel excipient, dodecyl-2-N,N-
dimethylaminopropionate (DDAIP), was utilized to assess the
epidermal penetration of tolnaftate. Tolnaftate, an anti-fungal
agent, is approved as an over-the-counter (OTC) product for the
treatment of superfcial fungal infections including, athlete’s foot,
ringworm and jock itch. Utilizing human cadaver skin mounted on
Franz cells, tolnaftate skin fux was evaluated with and without
the presence of DDAIP. Over a 24-hour period, DDAIP at a
concentration of 0.5% enhanced tolnaftate permeation through
human cadaver skin relative to the marketed tolnaftate formulation
(1%). Increased tolnaftate penetration may decrease the number
of applications and treatment duration required for dermatophyte
therapy.
Keywords: Tolnafate; Permeation; Excipient;, Dermatophyte;
DDAIP
Introduction
Causative organisms responsible for fungal infections of the skin,
classifed as dermatophytes include Microsporum, Trichophyton, and
Epidermophyton spp [1,2]. Dermatophytosis is generally limited to
keratin-producing cells of the skin but may become more invasive
due to trauma, moisture, secondary infection or patient status [2-4].
Te superfcial nature of the infection allows the fungus to be easily
transmissible on contact. Terefore, early diagnosis and treatment
initiation not only limit the primary infection but also transmission
[1,2]. Te treatment regimen frequently employed to treat these
superfcial epidermal fungal infections is topical application of
tolnafate [3]. Tolnafate, a thiocarbamate, is fungicidal at its
marketed concentration of 1%. Te customary treatment regimen is
topical application of the 1% cream on the afected area, twice daily
*Corresponding author: S. Meier-Davis, c/o NexMed Inc., 11975 El Camino
Real, Suite 300, San Diego, CA 92130, USA, Tel: 858-222-8041; Fax: 858-587-
2131; E-mail:- smeierdavis@apricusbio.com
Received: July 03, 2012 Accepted: August 09, 2012 Published: August 13,
2012
[1,5]. Tolnafate is poorly absorbed and, hence, a good candidate
for topical treatment of superfcial infections. However, increased
penetration of the anti-fungal may reduce the number of applications
and the overall treatment duration necessary to clear the infection [6].
Resistance to anti-fungal therapy increases with duration of therapy
[7]. Consequently, development of a tolnafate formulation with
increased epidermal penetrance could not only decrease the treatment
duration but also decrease the potential for organism resistance.
Efcient permeation of pharmaceutical agents through the
stratum corneum is dependent upon permeation enhancers.
Permeation enhancers are thought to enhance delivery of topically
applied drugs by increasing the thermodynamic activity of the
stratum corneum or traversing between the intercalated lipid layers
[8,9]. A number of permeation enhancers have been used to enhance
topical drug delivery including isopropyl myristate, capric acid, lauric
acid, myristic acid, oleic acid, Tween 20, Tween 80, sodium lauryl
sulfate and Span 80 [10,11]. DDAIP is a novel excipient that also may
act as a permeation enhancer in combination with pharmaceutical
agents. Te putative mechanism for enhanced permeation by DDAIP
is due to the temporary changes of the lipid bi-layer permeation
dynamics including loosening of the tight junctions between skin
cells [12]. Additionally, at the pH of skin, DDAIP remains stable for
>100 hours, potentially allowing prolonged permeation (unpublished
data). Te objective of this study was to determine whether DDAIP
enhances the permeation of the marketed formulation of tolnafate.
Increased permeation of tolnafate may contribute to enhanced cure
rates of superfcial dermatophyte infections.
Materials and Methods
All reagents used in this study were analytical reagent grade
or better. Tolnafate was commercially available (Lot 14007) and
contains 1% tolnafate, butylated hydroxytoluene, cetanol, liquid
parafn, methylparaben, polyoxyethylene cetylether, propylene
glycol, propylparaben, purifed water, sorbitan monostearate and
stearyl alcohol. A tolnafate formulation was developed with the
novel excipient, dodecyl-2-N,N- dimethylaminopropionate (DDAIP,
lot number R1050) and evaluated for skin penetration against the
OTC product, both consisting of a fnal tolnafate concentration
of 1%. Human cadaver skin was obtained from the University of
California, San Diego Skin Bank and stored at -80°C. Te skin was
thawed by immersing in 0.9% sodium chloride for 30 minutes prior
to the experiment. In vitro skin fux was conducted by mounting the
human cadaver skin sections (US Tissue & Cells-lots 118122127 and
118235129) onto Franz difusion cells (Permegear, Model # VC9).
Each experiment comprised either 6 or 9 samples derived from
two cadaver skin donors. Te receptor compartment contained a
solution of phosphate-bufered isotonic saline (PBS), pH 7.4 ± 0.1
with 20% ethanol, 0.1% gentamicin sulfate and 0.05% thio-urea,
maintained at 32.0 ± 0.5°C. Te test formulations (100 µL) were
applied directly onto the cadaver epidermis (0.64 cm
2
). Samples were
collected at specifed times from the receptor compartment and the
skin was homogenized for determination of tolnafate levels. Te skin