Esters of 6-aminohexanoic acid as skin permeation enhancers: The effect of branching in the alkanol moiety

Journal of Pharmaceutical Sciences

Volumn 94, Issue 7, 2005, Pages 1494-1499

  Hrabálek, Alexandr ^a   Vávrová, Kateřina ^a   Doležal, Pavel ^a   Macháček, Miloš ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

Author keywords

6 aminohexanoic acid derivatives; Branched alkyl chain; Human skin in vitro; Permeation enhancement; Transdermal drug delivery

Indexed keywords

6 AMINOHEXANOIC ACID CYCLODODECYL ESTER; 6 AMINOHEXANOIC ACID DODECAN 1 YL ESTER; 6 AMINOHEXANOIC ACID DODECAN 2 YL ESTER; 6 AMINOHEXANOIC ACID DODECAN 4 YL ESTER; ALKANOL; AMINOCAPROIC ACID; AROMATIC COMPOUND; ESTER DERIVATIVE; LIPID; THEOPHYLLINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; EVALUATION; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; MOLECULAR INTERACTION; SKIN PERMEABILITY; STRATUM CORNEUM; STRUCTURE ACTIVITY RELATION;

EID: 23844541304     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20376     Document Type: Article

References (13)

1. Williams AC, Barry BW. 2004. Penetration enhancers. Adv Drug Deliv Rev 56:603-618.
2. Barry BW. 1983. Dermatological formulations: Percutaneous absorption, New York: Marcel Dekker.
3. Vávrová K, Hrabálek A, Doležal P, Šámalová L, Palát K, Zbytovská J, Holas T, Klimentová J. 2003. Synthetic ceramide analogues as skin permeation enhancers: Structure-activity relationships. Bioorg Med Chem 11:5381-5390.
4. Vávrová K, Hrabálek A, Doležal P, Holas T, Zbytovská J. 2003. L-Serine and glycine based ceramide analogues as transdermal permeation enhancers: Polar head size and hydrogen bonding. Bioorg Med Chem Lett 13:2351-2353.
5. Kanikkannan N, Kandimalla K, Lamba SS, Singh M. 2000. Structure-activity relationship of chemical penetration enhancers in transdermal drug delivery. Curr Med Chem 7:593-608.
6. Aungst BJ. 1989. Structure/effect studies of fatty acid isomers as skin penetration enhancers and skin irritants. Pharm Res 6:244-247.
7. Chantasart D, Li SK, He N, Warner KS, Prakongpan S, Higuchi WI. 2004. Mechanistic studies of branchedchain alkanols as skin permeation enhancers. J Pharm Sci 93:762-779.
8. Sinha VR, Kaur MP. 2000. Permeation enhancers for transdermal drug delivery. Drug Dev Ind Pharm 26:1131-1140.
9. Houben-Weyl. 1980. Methoden der Organischen Chemie, VI/1a/2, Alkohole II, Stuttgart: Georg Thieme Verlag. 948p.
10. Doležal P, Hrabálek A, Semecký V. 1993. ε-aminocaproic acid esters as transdermal penetration enhancing agents. Pharm Res 10:1015-1019.
11. Mguni R. 1996. Diploma Thesis, Charles University, Faculty of Pharmacy.
12. Hrabálek A, Doležal P, Macháček M. 2001. 7-aminoheptanoic and 8-aminooctanoic acid esters. Russ J Appl Chem 74:1066-1067.
13. Hrabálek A, Doležal P, Roman M, Macháček M, Šklubalová Z. 1994. Esters of ω-amino acids as flexible penetration enhancers. Pharmazie 49:325-328.