The enhancing effect and promoting mechanisms of the stereoisomeric monoterpene alcohol esters as enhancers for drugs with different physicochemical properties

Rai, 2016, Novel drug delivery system: an immense hope for diabetics, Drug Deliv, 23, 2371, 10.3109/10717544.2014.991001 Serpe, 2016, Influence of salivary washout on drug delivery to the oral cavity using coated microneedles: an in vitro evaluation, Eur J Pharm Sci, 93, 215, 10.1016/j.ejps.2016.08.023 Strasinger, 2016, Navigating sticky areas in transdermal product development, J Control Release, 233, 1, 10.1016/j.jconrel.2016.04.032 Gratieri, 2013, Next generation intra- and transdermal therapeutic systems: using non- and minimally-invasive technologies to increase drug delivery into and across the skin, Eur J Pharm Sci, 50, 609, 10.1016/j.ejps.2013.03.019 Karande, 2009, Enhancement of transdermal drug delivery via synergistic action of chemicals, Biochim Biophys Acta, 1788, 2362, 10.1016/j.bbamem.2009.08.015 Vaddi, 2002, Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry, J Pharm Sci, 91, 1639, 10.1002/jps.10160 Aqil, 2007, Status of terpenes as skin penetration enhancers, Drug Discov Today, 12, 1061, 10.1016/j.drudis.2007.09.001 Kanikkannan, 2000, Structure-activity relationship of chemical penetration enhancers in transdermal drug delivery, Curr Med Chem, 7, 593, 10.2174/0929867003374840 Arellano, 1996, Enhancing effect of terpenes on the in vitro percutaneous absorption of diclofenac sodium, Int J Pharm, 130 Godwin, 1999, Influence of drug lipophilicity on terpenes as transdermal penetration enhancers, Drug Dev Ind Pharm, 25, 905, 10.1081/DDC-100102251 Charoo, 2005, Transdermal delivery of flurbiprofen: permeation enhancement, design, pharmacokinetic, and pharmacodynamic studies in albino rats, Pharm Dev Technol, 10, 343, 10.1081/PDT-65661 Choi, 2012, Effect of fatty acids on the transdermal delivery of donepezil: in vitro and in vivo evaluation, Int J Pharm, 422, 83, 10.1016/j.ijpharm.2011.10.031 Zhao, 2007, A novel transdermal patch incorporating isosorbide dinitrate with bisoprolol: in vitro and in vivo characterization, Int J Pharm, 337, 88, 10.1016/j.ijpharm.2006.12.030 Sun, 2012, Formulation and in vitro/in vivo correlation of a drug-in-adhesive transdermal patch containing azasetron, J Pharm Sci, 101, 4540, 10.1002/jps.23317 Nielsen, 2006, Natural oils affect the human skin integrity and the percutaneous penetration of benzoic acid dose-dependently, Basic Clin Pharmacol Toxicol, 98, 575, 10.1111/j.1742-7843.2006.pto_388.x Ibrahim, 2010, Chemical enhancer solubility in human stratum corneum lipids and enhancer mechanism of action on stratum corneum lipid domain, Int J Pharm, 383, 89, 10.1016/j.ijpharm.2009.09.014 Vávrová, 2005, Amphiphilic transdermal permeation enhancers: structure-activity relationships, Curr Med Chem, 12, 2273, 10.2174/0929867054864822 Kunta, 1997, Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin, J Pharm Sci, 86, 1369, 10.1021/js970161+ Warner, 2001, Influences of alkyl group chain length and polar head group on chemical skin permeation enhancement, J Pharm Sci, 90, 1143, 10.1002/jps.1068 He, 2003, Mechanistic study of alkyl azacycloheptanones as skin permeation enhancers by permeation and partition experiments with hairless mouse skin, J Pharm Sci, 92, 297, 10.1002/jps.10269 Riviere, 2001, Potential and problems of developing transdermal patches for veterinary applications, Adv Drug Deliv Rev, 50, 175, 10.1016/S0169-409X(01)00157-0 Uppoor, 2001, Regulatory perspectives on in vitro (dissolution)/in vivo (bioavailability) correlations, J Control Release, 72, 127, 10.1016/S0168-3659(01)00268-1 Yang, 2015, Development and validation of in vitro-in vivo correlation (IVIVC) for estradiol transdermal drug delivery systems, J Control Release, 210, 58, 10.1016/j.jconrel.2015.05.263 Chu, 2020, Chiral 4-O-acylterpineol as transdermal permeation enhancers: insights of the enhancement mechanisms of a transdermal enantioselective delivery system for flurbiprofen, Drug Deliv, 27, 723, 10.1080/10717544.2020.1760403 Zhao, 2018, Molecular mechanism of ion-pair releasing from acrylic pressure sensitive adhesive containing carboxyl group: roles of doubly ionic hydrogen bond in the controlled release process of bisoprolol ion-pair, J Control Release, 289, 146, 10.1016/j.jconrel.2018.09.024 Liu, 2019, Transdermal enhancement strategy of ketoprofen and teriflunomide: the effect of enhanced drug-drug intermolecular interaction by permeation enhancer on drug release of compound transdermal patch, Int J Pharm, 572, 10.1016/j.ijpharm.2019.118800 Song, 2016, Probing the role of chemical enhancers in facilitating drug release from patches: mechanistic insights based on FT-IR spectroscopy, molecular modeling and thermal analysis, J Control Release, 227, 13, 10.1016/j.jconrel.2016.02.027 Jain, 2002, Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes, J Control Release, 79, 93, 10.1016/S0168-3659(01)00524-7 Imura, 2001, Preparation of liposomes containing Ceramide 3 and their membrane characteristics, Colloids Surf B, 20, 1, 10.1016/S0927-7765(00)00149-1 Rerek, 2005, FTIR spectroscopic studies of lipid dynamics in phytosphingosine ceramide models of the stratum corneum lipid matrix, Chem Phys Lipids, 134, 51, 10.1016/j.chemphyslip.2004.12.002 Liu, 2017, A systemic evaluation of drug in acrylic pressure sensitive adhesive patch in vitro and in vivo: the roles of intermolecular interaction and adhesive mobility variation in drug controlled release, J Control Release, 252, 83, 10.1016/j.jconrel.2017.03.003 Wu, 2001, Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study, Int J Pharm, 222, 225, 10.1016/S0378-5173(01)00707-4 Boncheva, 2008, Molecular organization of the lipid matrix in intact Stratum corneum using ATR-FTIR spectroscopy, Biochim Biophys Acta, 1778, 1344, 10.1016/j.bbamem.2008.01.022 Mendelsohn, 2006, Determination of molecular conformation and permeation in skin via IR spectroscopy, microscopy, and imaging, Biochim Biophys Acta, 1758, 923, 10.1016/j.bbamem.2006.04.009 Tatulian, 2019, FTIR analysis of proteins and protein-membrane interactions, Methods Mol Biol, 2003, 281, 10.1007/978-1-4939-9512-7_13 Ibrahim, 2009, Effects of chemical enhancers on human epidermal membrane: structure-enhancement relationship based on maximum enhancement (E(max)), J Pharm Sci, 98, 926, 10.1002/jps.21476 Ahad, 2016, The application of anethole, menthone, and eugenol in transdermal penetration of valsartan: enhancement and mechanistic investigation, Pharm Biol, 54, 1042, 10.3109/13880209.2015.1100639 Li, 2019, Permeation-enhancing effects and mechanisms of O-acylterpineol on isosorbide dinitrate: mechanistic insights based on ATR-FTIR spectroscopy, molecular modeling, and CLSM images, Drug Deliv, 26, 107, 10.1080/10717544.2018.1561764 Chen, 2014, Saturated long-chain esters of isopulegol as novel permeation enhancers for transdermal drug delivery, Pharm Res, 31, 1907, 10.1007/s11095-013-1292-0 Li, 2017, Mechanistic insights of the enhancement effect of sorbitan monooleate on olanzapine transdermal patch both in release and percutaneous absorption processes, Eur J Pharm Sci, 107, 138, 10.1016/j.ejps.2017.07.006 Zhao, 2017, Mechanism study on ion-pair complexes controlling skin permeability: effect of ion-pair dissociation in the viable epidermis on transdermal permeation of bisoprolol, Int J Pharm, 532, 29, 10.1016/j.ijpharm.2017.08.080 Prasad, 2007, Effect of DC/mDC iontophoresis and terpenes on transdermal permeation of methotrexate: in vitro study, Int J Pharm, 333, 70, 10.1016/j.ijpharm.2006.09.058 Amin, 2008, Mechanism of in vitro percutaneous absorption enhancement of carvedilol by penetration enhancers, Pharm Dev Technol, 13, 533, 10.1080/10837450802309646