Abstract
Surfactants are widely used excipients in topical formulations, not only for their solubilizing and emulsifying properties but also for their well-known capacity to enhance drug permeation. Although nonionic surfactants are frequently chosen because of their mild effect on the skin, they share a low efficacy as permeation enhancers. Among nonionic surfactants, sucrose fatty acid esters (SEs) have awoken the interest of different research groups due to their interesting properties, such as biodegradability, nontoxicity, low irritation to the skin, and their ability to form liquid crystals and microemulsions (among other systems). Furthermore, as described in this chapter, SEs have shown a good capacity to enhance the transcutaneous transport of drugs. Their enhancing ability depends on different factors such as the physicochemical properties of the drug, the type of SEs, and the characteristics of the vehicle or the delivery system. This chapter gathers information about the studies related to SEs as transdermal penetration enhancers.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Abdel-Mageed HM, El-Laithy HM, Mahran LG, Fahmy AS, Mader K, Mohamed SA (2012) Development of novel flexible sugar ester vesicles as carrier systems for the antioxidant enzyme catalase for wound healing applications. Process Biochem 47:1155–1162
Ahsan F, Arnold JJ, Meezan E, Pillion DJ (2003) Sucrose cocoate, a component of cosmetic preparations, enhances nasal and ocular peptide absorption. Int J Pharm 251:195–203
Ayala-Bravo H, Quintanar-Guerrero D, Naik A, Kalia NY, Cornejo-Bravo JM, Ganem-Quintanar A (2003) Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res 47:1267–1273
Bolzinger MA, Thevenin, Carduner C, Poelman MC (1998) Bicontinuous sucrose ester microemulsion: a new vehicle for topical delivery of niflumic acid. Int J Pharm 176:39–45
Bouwstra JA (1998) Inventor; Rijksuniversiteit Leiden assignee. Phospholipid-and cholesterol-free aqueous composition for topical application to the skin. US Patent US 5,830,499
Calderilla-Fajardo SB, Cázares-Delgadillo J, Villalobos-García R, Quintanar-Guerrero D, Ganem-Quintanar A (2006) Influence of sucrose esters on the in vivo percutaneous penetration of octyl methoxycinnamate formulated in nanocapsules, nanoemulsion, and emulsion. Drug Dev Ind Pharm 32:107–113
Cázares-Delgadillo J, Naik A, Kalia YN, Quintanar-Guerrero D, Ganem-Quintanar A (2005) Skin permeation enhancement by sucrose esters: a pH-dependent phenomenon. Int J Pharm 297:204–212
Chang Y (1990) Inventor; Paco Pharmaceutical Services, Inc, assignee. Transdermal drug delivery device containing a dual permeation enhancer. US Patent US 4,956,171 A
Chantasart D, Li SK (2012) Structure enhancement relationship of chemical penetration enhancers in drug transport across the stratum corneum. Pharmaceutics 4:71–92
Chen H, Chang X, Du D, Li J, Xu H, Yang X (2006) Microemulsion-based hydrogel formulation of ibuprofen for topical delivery. Int J Pharm 315:52–58
Cheng YL, Gale RM, Sugihara E, Sanders HF (1988) Inventors; ALZA Corporation, assignee. Transdermal delivery devices containing sucrose coconut fatty esters as skin permeation enhancers. European Patent EP 280413 A1
Cruces MA, Plou FJ, Ferrer M, Bernabé M, Ballesteros A (2001) Improved synthesis of sucrose fatty acid monoesters. J Am Oil Chem Soc 78(5):541–546
Csizmazia E (2011) Drug permeation study through biological membrane barriers. PhD thesis, University of Szeged, Szeged
Csizmazia E, Erős G, Berkesi O, Berkó S, Szabó-Révész P, Csányi E (2011) Penetration enhancer effect of sucrose laurate and transcutol on ibuprofen. J Drug Deliv Sci Technol 21(5):411–415
Csizmazia E, Erős G, Berkesi O, Berkó S, Szabó-Révész P, Csányi E (2012) Ibuprofen penetration enhance by sucrose ester examined by ATR-FTIR in vivo. Pharm Dev Technol 17(1):125–128
Csóka G, Marton S, Zelko R, Otomo N, Antal I (2007) Application of sucrose fatty acid esters in transdermal therapeutic systems. Eur J Pharm Biopharm 65:233–237
Ding Z, Bivas-Benita M, Hirschberg H, Kersten GFA, Jiskoot W, Bouwstra JA (2008) Preparation and characterization of diphtheria toxoid-loaded elastic vesicles for transcutaneous immunization. J Drug Target 16(7–8):555–563
El-Laithy HM (2009) Novel transdermal delivery of Timolol maleate using sugar esters: preclinical and clinical studies. Eur J Pharm Biopharm 72(1):239–245
El-Laithy HM, Shoukry O, Mahran LG (2011) Novel sugar esters proniosomes for transdermal delivery of vinpocetine: preclinical and clinical studies. Eur J Pharm Biopharm 77:43–55
Fang JY, Hwang TL, Fang CL, Chiu HC (2003) In vitro and in vivo evaluations of the efficacy and safety of skin permeation enhancers using flurbiprofen as a model drug. Int J Pharm 255:153–166
Gale RM, Nelson M, Enscore DJ, Cheng YL, Nedberge DE, Libicki SB (1988) Inventors; ALZA Corporation, assignee. Transdermal delivery system and permeation enhancers for administration of progesterone and/or estradiol esters. European Patent EP 279977 A2
Ganem-Quintanar A, Quintanar-Guerrero D, Falson-Rieg F, Buri P (1998) Ex vivo oral mucosal permeation of lidocaine hydrochloride with sucrose fatty acid esters as absorption enhancers. Int J Pharm 173:203–210
Gutiérrez JM, González C, Maestro A, Solè I, Pey CM, Nolla J (2008) Nano-emulsions: new applications and optimization of their preparation. Curr Opin Colloid Interface Sci 13(4):245–251
Huang D, Jiang X, Zhu H, Fu X, Zhong K, Gao W (2010) Improved synthesis of sucrose fatty acid monoesters under ultrasonic irradiation. Ultrason Sonochem 17:352–355
Höller S (2008) Cubic gels, microemulsions and nanoemulsions for optimized skin penetration/permeation of active molecules and improved chemical stability. PhD thesis, Universität Wien, Wien
Honeywell-Nguyen PL, Frederik PM, Bomans PHH, Junginger HE, Bouwstra JA (2002a) Transdermal delivery of pergolide from surfactant-based elastic and rigid vesicles: characterization and in vitro transport studies. Pharm Res 19(7):991–997
Honeywell-Nguyen PL, Van den Bussche MH, Junginger HE, Bouwstra JA (2002b) The effect of surfactant-based elastic and rigid vesicles on the penetration of lidocaine across human skin. STP Pharma Sci 12(4):257–262
Hoo-Kyun C, Je-Phil R (2010) Inventors; Transdermal triptan delivery system. Patent application publication. US Patent 20,100,209,484 A1
Husband FA, Sarney DB, Barnard MJ, Wilde PJ (1998) Comparison of foaming and interfacial properties of pure sucrose monolaurates, dilaurate and commercial preparations. Food Hydrocoll 12:237–244
Klang V, Matsko N, Zimmermann AM, Vojnikovic E, Valenta C (2010) Enhancement of stability and skin permeation by sucrose stearate and cyclodextrins in progesterone nanoemulsions. Int J Pharm 393:152–160
Klang V, Schwarz JC, Matsko N, Rezvani E, El-Hagin N, Wirth M, Valenta C (2011) Semi-solid sucrose stearate-based emulsions as dermal drug delivery systems. Pharmaceutics 3:275–306. http://www.mdpi.com/1999-4923/3/2/275
Kreilgaard M, Pedersen EJ, Jaroszewski JW (2000) NMR characterisation and transdermal drug delivery potential of microemulsion systems. J Control Release 69:421–433
Kumar GP, Rajeshwarrao P (2011) Nonionic surfactant vesicular systems for effective drug delivery-an overview. Acta Pharmaceutica Sinica B 1(4):208–219
Kürti L, Veszelka S, Bocsik A, Khue Dung NT, Ózsvári B, Puskás LG, Kittel A, Szabó-Révész P, Deli MA (2012) The effect of sucrose esters on a culture model of the nasal barrier. Toxicol In Vitro 26:445–454
Lehmann L, Keipert S, Gloor M (2001) Effects of microemulsions on the stratum corneum and hydrocortisone penetration. Eur J Pharm Biopharm 52:129–136
Lerk PC, Sucker H (1993) Application of sucrose laurate in topical preparations of cyclosporine A. Int J Pharm 92(1–3):203–210
Lerk PC (1991) Characterisation and pharmaceutical application of new polyoxyethyleneglycol free surfactants in particular sucrose laurate. PhD Thesis, Basel, Switzerland
Lerk PC, Sucker H (1993) Application of sucrose laurate in topical preparations of cyclosporine A. Int J Pharm 92: 203-210.
Li GL, Danhof M, Bouwstra JA (2001) Effect of elastic liquid-state vesicle on apomorphine iontophoresis transport through human skin in vitro. Pharm Res 18(11):1627–1630
Maggio ET, Meezan E, Pillion DJ, Morgan SL, Baggott JE (2009) Inventors; Aegis Therapeutics, Llc, assignee. Controlled release stable, self-assembling, biocompatible and biodegradable therapeutic hydrogel formulations. Patent Application WO 2009029543 A1
Marjukka Suhonen T, Bouwsra JA, Urtti A (1999) Chemical enhancement of percutaneous absorption in relation to stratum corneum structural alterations. J Control Release 59:149–161
Mitsubishi-Kagaku Foods Corporation [Internet] (2012) Ryoto Sugar Ester Technical Information. SURFHOPE™SE COSME; [cited 2012 Dec 13]. Available from: http://www.mfc.co.jp/english/se_cosme/secosme.htm
Muzzalupo R, Tavano L, Cassano R, Trombino S, Ferrarelli T, Picci N (2011) A new approach for the evaluation of niosomes as effective transdermal drug delivery systems. Eur J Pharm Biopharm 79:28–35
Ogiso T, Iwaki M, Tsuji S (1991) Percutaneous absorption of bromhexine in rats. Chem Pharm Bull 39(6):1609–1611
Okamoto H, Sakai T, Danjo K (2005) Effect of sucrose fatty acid esters on transdermal permeation of lidocaine and ketoprofen. Biol Pharm Bull 28(9):1689–1694
Okamoto H, Sakai T, Tokuyama C, Danjo K (2011) Sugar ester J-1216 enhances percutaneous permeation of ionized lidocaine. J Pharm Sci 100(10):4482–4490
Otto A, Wiechers JW, Kelly CL, Dederen JC, Hadgraft J, du Plessis J (2010) Effect of emulsifiers and their liquid crystalline structures in emulsions on dermal and transdermal delivery of hydroquinone, salicylic acid and octadecenedioic acid. Skin Pharmacol Physiol 23:273–282
Papp J (2012) Preparation and evaluation of metoprolol tartrate patches containing different polymer components. PhD thesis, University of Semmelweis, Budapest
Peltola S, Saarinen-Savolainen P, Kiesvaara J, Suhonen TM, Urtti A (2003) Microemulsions for topical delivery of estradiol. Int J Pharm 254:99–107
Piao H, Kamiya N, Hirata A, Fijiii T, Goto M (2008) A novel solid-in-oil nanosuspension for transdermal delivery of diclofenac sodium. Pharm Res 25(4):896–901
Podlogar F, Bester Rogac M, Gasperlin M (2005) The effect of internal structure of selected water-Tween 40-Imwitor-IPM microemulsions on ketoprofene release. Int J Pharm 302:68–77
Polat T, Linhardt RJ (2001) Syntheses and applications of sucrose-based esters. J Surfact Deterg 4(4):415–421
Quintanar-Guerrero D, Ganem-Rondero FA, Cazares-Delgadillo J, Ayala-Bravo HA (2005) Inventors; FES-Cuautitlan UNAM, assignee. Sucrose-fatty acid ester-based drug penetration promoter. PCT Int. Appl. WO 2005079855
Smith DE (1977) Inventor; The Procter and Gamble Company, assignee. Dermatological compositions. US Patent US 4,046,886
Spernath A, Aserin A, Sintov AC, Garti N (2008) Phosphatidylcholine embedded micellar systems: enhanced permeability through rat skin. J Colloid Interface Sci 318:421–429
Soultani S, Ognier S, Engasser JM, Ghoul M (2003) Comparative study of some surface active properties of fructose esters and commercial sucrose esters. Colloids Surf A 227:35–44
Tamarkin D, Friedman D, Meir E (2008) Inventors, Foamix Ltd. assignee. Alcohol-free cosmetic and pharmaceutical foam carrier comprising hydrophobic solvent such as mineral/silicone/vegetable oil, triglycerides, isopropyl myristate, octyl dodecanol, foam adjuvant agent, surfactant and gelling agent. US Patent Appl. US 20,080,031,907
Tahara Y, Honda S, Kamiya N, Piao H, Hirata A, Hayakawa E, Fujii T, Goto M (2008) A solid-in-oil nanodispersion for transcutaneous protein delivery. J Control Release 131(1):14–18
Tavano L, Muzzalupo R, Cassano R, Trombino S, Ferrarelli T, Picci N (2010) New sucrose cocoate based vesicles: preparation characterization and skin permeation studies. Colloids Surf B Biointerfaces 75:319–322
Toro C, Sanchez SA, Zanocco A, Lemp E, Gratton E, Gunther G (2009) Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size. Chem Phys Lipids 157(2):104–112
Thevenin MA, Grossiord JL, Poelman MC (1996) Sucrose esters/cosurfactant microemulsion systems for transdermal delivery: assessment of bicontinuous structures. Int J Pharm 137:177–186
Trommer H, Neubert RHH (2006) Overcoming the stratum corneum: the modulation of skin penetration. Skin Pharmacol Physiol 19:106–121
Szűts A, Pallagi E, Regdon G, Aigner Z, Szabó-Révész P (2007) Study of thermal behaviour of sugar esters. Int J Pharm 336:199–207
Szűts A, Szabó-Révész P (2012) Sucrose esters as natural surfactants in drug delivery systems—a mini-review. Int J Pharm 433:1–9
Vermeire A, De Muynck C, Vandenbossche G, Eechaute W, Geerts ML, Remon JP (1996) Sucrose laurate gels as a percutaneous delivery system for oestradiol in rabbits. J Pharm Pharmacol 48:463–467
Vučinić-Milanković M, Savić S, Vuleta G, Vučinić S (2007) The physicochemical characterization and in vitro/in vivo evaluation of natural surfactants-based emulsions as vehicles for diclofenac diethylamine. Drug Dev Ind Pharm 33:221–234
Williams AC, Barry BW (2004) Penetration enhancers. Adv Drug Deliv Rev 56:603–618
Yamato K, Takahashi Y, Akiyama H, Tsuji K, Onishi H, Machida Y (2009) Effect of penetration enhancers on transdermal delivery of propofol. Biol Pharm Bull 32(4):677–683
Yang F, Kamiya N, Goto M (2012) Transdermal delivery of the anti-rheumatic agent methotrexate using a solid-in-oil Nanocarrier. Eur J Pharm Biopharm 82:158–163
Yanke L, Shufen Z, Jinzong Y, Qinghui W (2004) Relationship of solubility parameters to interfacial properties of sucrose esters. Colloids Surf A 248:127–133
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Nava-Arzaluz, M.G., Piñón-Segundo, E., Ganem-Rondero, A. (2015). Sucrose Esters as Transdermal Permeation Enhancers. In: Dragicevic, N., Maibach, H. (eds) Percutaneous Penetration Enhancers Chemical Methods in Penetration Enhancement. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-47039-8_16
Download citation
DOI: https://doi.org/10.1007/978-3-662-47039-8_16
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-47038-1
Online ISBN: 978-3-662-47039-8
eBook Packages: MedicineMedicine (R0)