Efficiency of fatty acids as chemical penetration enhancers: Mechanisms and structure enhancement relationship

Pharmaceutical Research

Volumn 27, Issue 1, 2010, Pages 115-125

  Ibrahim, Sarah A ^a   Li, S Kevin ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

Chemical penetration enhancers; Corticosterone; Emax; Estradiol; Fatty acids; Skin

Indexed keywords

CORTICOSTERONE; ESTRADIOL; FATTY ACID DERIVATIVE; LAURIC ACID; LINOLEIC ACID; MYRISTIC ACID; OLEIC ACID; PALMITIC ACID; PENETRATION ENHANCING AGENT; PENTADECANOIC ACID; RICINOLEIC ACID; SEBACIC ACID; SILASTIC; STEARIC ACID; TRIDECANOIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG PENETRATION; DRUG SOLUBILITY; EPIDERMIS; HUMAN; LIPOPHILICITY; MELTING POINT; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SKIN PENETRATION; SOLVENT EFFECT; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, CUTANEOUS; ESTRADIOL; FATTY ACIDS; HUMANS; PERMEABILITY; SILICONE ELASTOMERS; SKIN ABSORPTION; SOLVENTS;

EID: 72949090585     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-009-9985-0     Document Type: Article

References (27)

1. B Al-Qallaf DB Das D Mori Z Cui 2007 Modelling transdermal delivery of high molecular weight drugs from microneedle systems Philosophical Transactions of the Royal Society a-Mathematical Physical and Engineering Sciences. 365 2951 67 10.1098/rsta.2007.0003 1:CAS:528:DC%2BD2sXhsVyjurnM
2. P Karande A Jain K Ergun V Kispersky S Mitragotri 2005 Design principles of chemical penetration enhancers for transdermal drug delivery Proc Natl Acad Sci U S A. 102 4688 93 10.1073/pnas.0501176102 1:CAS:528:DC%2BD2MXjt1Oiurc%3D 15774584 (Pubitemid 40471515)
3. Ansel HC, Allen LV, Popovich NG. Pharmaceutical dosage forms and drug delivery systems. Philadelphia: Lippincott-Williams & Wilkins; 1999.
4. I El-Gibaly FA Mohamed M Shehata 1998 Effect of some penetration enhancers on release of clotrimazole from different gel formulations and histological changes of rabbit skin Pharmazeutische Industrie. 60 1088 95 1:CAS:528:DyaK1MXitlKhsg%3D%3D
5. BC Finnin TM Morgan 1999 Transdermal penetration enhancers: applications, limitations, and potential J Pharm Sci. 88 955 8 10.1021/js990154g 1:CAS:528:DyaK1MXlvVeqsb8%3D 10514338 (Pubitemid 29480582)
6. D Chantasart P Sa-Nguandeekul S Prakongpan SK Li WI Higuchi 2007 Comparison of the effects of chemical permeation enhancers on the lipoidal pathways of human epidermal membrane and hairless mouse skin and the mechanism of enhancer action J Pharm Sci. 96 2310 26 10.1002/jps.20865 1:CAS:528:DC%2BD2sXhtVWntLbI 17387696 (Pubitemid 47477889)
7. T Ogiso T Paku M Iwaki T Tanino 1995 Percutaneous penetration of fluorescein isothiocyanate-dextrans and the mechanism for enhancement effect of enhancers on the intercellular penetration Biol Pharm Bull 18 1566 71 1:CAS:528:DyaK2MXps1Gltrk%3D 8593481
8. CY Goates K Knutson 1993 Enhanced permeation and stratum corneum structural alterations in the presence of dithiothreitol Biochim Biophys Acta 1153 289 98 10.1016/0005-2736(93)90418-Y 1:CAS:528:DyaK2cXnsVWlsQ%3D%3D 8274500 (Pubitemid 24028301)
9. EM Niazy 1991 Influence of oleic-acid and other permeation promoters on transdermal delivery of dihydroergotamine through rabbit skin Int J Pharm. 67 97 100 10.1016/0378-5173(91)90269-T 1:CAS:528:DyaK3MXovVGmsw%3D%3D
10. D Chantasart SK Li N He KS Warner S Prakongpan WI Higuchi 2004 Mechanistic studies of branched-chain alkanols as skin permeation enhancers J Pharm Sci. 93 762 79 10.1002/jps.10550 1:CAS:528:DC%2BD2cXitV2ltr4%3D 14762914 (Pubitemid 38332308)
11. SA Ibrahim SK Li 2009 Effects of chemical enhancers on human epidermal membrane: Structure-enhancement relationship based on maximum enhancement Emax J Pharm Sci. 98 926 44 10.1002/jps.21476 1:CAS:528:DC%2BD1MXjt1Wltr0%3D 18623209
12. P Karande A Jain S Mitragotri 2006 Insights into synergistic interactions in binary mixtures of chemical permeation enhancers for transdermal drug delivery J Control Release. 115 85 93 10.1016/j.jconrel.2006.07.001 1:CAS:528:DC%2BD28XpvVOhtLo%3D 16935378 (Pubitemid 44415077)
13. TM Morgan RA Parr BL Reed BC Finnin 1998 Enhanced transdermal delivery of sex hormones in swine with a novel topical aerosol J Pharm Sci. 87 1219 25 10.1021/js980026c 1:CAS:528:DyaK1cXlsFKgsbs%3D 9758680 (Pubitemid 28455612)
14. SA Ibrahim SK Li 2009 Effects of solvent deposited enhancers on transdermal permeation and their relationship with Emax J Control Release. 136 117 24 10.1016/j.jconrel.2009.01.023 1:CAS:528:DC%2BD1MXlvFGrt7c%3D 19331847
15. ER Cooper 1984 Increased skin permeability for lipophilic molecules J Pharm Sci. 73 1153 6 10.1002/jps.2600730831 1:CAS:528:DyaL2cXlslOgurY%3D 6491922
16. BW Barry SL Bennett 1987 Effect of penetration enhancers on the permeation of mannitol, hydrocortisone and progesterone through human skin J Pharm Pharmacol. 39 535 46 1:CAS:528:DyaL2sXkvVersrg%3D 2886623
17. K Kandimalla N Kanikkannan S Andega M Singh 1999 Effect of fatty acids on the permeation of melatonin across rat and pig skin in-vitro and on the transepidermal water loss in rats in-vivo J Pharm Pharmacol. 51 783 90 10.1211/0022357991773140 1:CAS:528:DyaK1MXlt1Kisb4%3D 10467952 (Pubitemid 29377949)
18. BJ Aungst 1989 Structure/effect studies of fatty acid isomers as skin penetration enhancers and skin irritants Pharm Res 6 244 7 10.1023/A: 1015921702258 1:CAS:528:DyaL1MXitFyqsrc%3D 2726682
19. BJ Aungst NJ Rogers E Shefter 1986 Enhancement of naloxone penetration through human skin in vitro using fatty-acids, fatty alcohols, surfactants. sulfoxides and amides Sulfoxides and Amides. Int J Pharm. 33 225 34 10.1016/0378-5173(86)90057-8 1:CAS:528:DyaL2sXjvVeksA%3D%3D (Pubitemid 17197807)
20. B Ongpipattanakul RR Burnette RO Potts ML Francoeur 1991 Evidence that oleic acid exists in a separate phase within stratum corneum lipids Pharm Res 8 350 4 10.1023/A:1015845632280 1:CAS:528:DyaK3MXitFChtbo%3D 2052523
21. GR Nanayakkara A Bartlett B Forbes C Marriott PJ Whitfield MB Brown 2005 The effect of unsaturated fatty acids in benzyl alcohol on the percutaneous permeation of three model penetrants Int J Pharm. 301 129 39 10.1016/j.ijpharm.2005.05.024 1:CAS:528:DC%2BD2MXptVWhsbs%3D 16019171 (Pubitemid 41206598)
22. Y Yokomizo H Sagitani 1996 The effects of phospholipids on the percutaneous penetration of indomethacin through the dorsal skin of guinea pig in vitro.2. The effects of the hydrophobic group in phospholipids and a comparison with general enhancers J Control Release 42 37 46 10.1016/0168-3659(96)01349-1 1:CAS:528:DyaK28Xltlyis7w%3D (Pubitemid 26297874)
23. GB Kasting LA Bowman 1990 Electrical analysis of fresh, excised human skin: a comparison with frozen skin Pharm Res 7 1141 6 10.1023/A:1015928225089 1:CAS:528:DyaK3cXmt1ylsL4%3D 2293212
24. KS Warner SK Li N He TM Suhonen D Chantasart D Bolikal WI Higuchi 2003 Structure-activity relationship for chemical skin permeation enhancers: probing the chemical microenvironment of the site of action J Pharm Sci. 92 1305 22 10.1002/jps.10367 1:CAS:528:DC%2BD3sXks1Kisbg%3D 12761819 (Pubitemid 36676475)
25. S.A. Ibrahim and S.K. Li. Chemical enhancer solubility in human stratum corneum lipids and enhancer mechanism of action on stratum corneum lipid domain. Int J Pharm. In Press (2009).
26. S.H. Yalkowsky and R.M. Dannenfelser. Aquasol Database of Aqueous Solubility., Version 5, 1992.
27. VB Nair R Panchagnula 2003 Effect of iontophoresis and fatty acids on permeation of arginine vasopressin through rat skin Pharmacol Res 47 563 9 10.1016/S1043-6618(03)00016-1 1:CAS:528:DC%2BD3sXjsVeis7g%3D 12742012 (Pubitemid 36542937)