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Enantioselective Penetration Enhancing Effect of Carvone on the in Vitro Transdermal Permeation of Nicorandil

Enantioselective Penetration Enhancing Effect of Carvone on the in Vitro Transdermal Permeation of Nicorandil

Yellela S R Krishnaiah, Aly Nada

Pharm Dev Technol. Sep-Oct 2012;17(5):574-82.

PMID: 21428701

Abstract:

The objective was to investigate the difference in penetration enhancing effect of R-carvone, S-carvone and RS-carvone on the in vitro transdermal drug permeation. In vitro permeation studies were carried out across neonatal rat epidermis from 2%w/v HPMC (hydroxypropyl methylcellulose) gel containing 4%w/v of nicorandil (a model drug) and a selected concentration (12%w/v) of either R-carvone, S-carvone or RS-carvone against a control. The stratum corneum (SC) of rats was treated with vehicle (70%v/v ethanol-water) or ethanolic solutions of 12%w/v R-carvone, S-carvone or RS-carvone. The enhancement ratio (ER) of R-carvone, S-carvone and RS-carvone when compared to control was about 37.1, 31.2 and 29.9, respectively indicating enantioselective penetration enhancing effect of carvone enantiomers. Furthermore, there was a significant decrease in the lag time required to produce a steady-state flux of nicorandil with S-carvone when compared to R-carvone and RS-carvone. DSC and FT-IR studies indicate that the investigated enantiomers of carvone exhibit a difference in their ability to affect the cellular organization of SC lipids and proteins thereby showing enantioselective transdermal drug permeation. It was concluded that R-carvone exhibited a higher penetration enhancing activity on transdermal permeation of nicorandil when compared to its S-isomer or racemic mixture.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2244168	(+)-Carvone		2244-16-8	Price

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