Permeation, stability and acute dermal irritation of miroestrol and deoxymiroestrol from Pueraria candollei var. mirifica crude extract loaded transdermal gels

References

• Aliyar H, Huber R, Loubert G, Schalau G. 2014. Efficient ibuprofen delivery from anhydrous semisolid formulation based on a novel cross-linked silicone polymer network: an in vitro and in vivo study. J Pharm Sci. 103(7):2005–2011.
   PubMed Web of Science ®Google Scholar
• Aliyar H, Schalau G. 2015. Recent developments in silicones for topical and transdermal drug delivery. Ther Deliv. 6(7):827–839.
   PubMed Web of Science ®Google Scholar
• Anusarnsoondhorn S. 1931. The remedy pamphlet of Kwao Krua tuber of Luang Anusornsuntarakromkarnpiset. Chiang Mai: Upatipongsa Press.
   Google Scholar
• Aqil M, Ahad A, Sultana Y, Ali A. 2007. Status of terpenes as skin penetration enhancers. Drug Discov Today. 12(23–24):1061–1067.
   PubMed Web of Science ®Google Scholar
• Baboota S, Al-Azaki A, Kohli K, Ali J, Dixit N, Shakeel F. 2007. Development and evaluation of a microemulsion formulation for transdermal delivery of terbinafine. PDA J Pharm Sci Technol. 61(4):276–285.
   PubMedGoogle Scholar
• Bali V, Ali M, Ali J. 2010. Study of surfactant combinations and development of a novel nanoemulsion for minimising variations in bioavailability of ezetimibe. Colloids Surf B Biointerfaces. 76(2):410–420.
   PubMed Web of Science ®Google Scholar
• Barry BW. 1991. Lipid-protein-partitioning theory of skin penetration enhancement. J Control Release. 15(3):237–248.
   Web of Science ®Google Scholar
• Bhatia KS, Gao S, Singh J. 1997. Effect of penetration enhancers and iontophoresis on the FT-IR spectroscopy and LHRH permeability through porcine skin. J Control Release. 47(1):81–89.
   Web of Science ®Google Scholar
• Brown MB, Hanpanitcharoen M, Martin GP. 2001. An in vitro investigation into the effect of glycosaminoglycans on the skin partitioning and deposition of NSAIDs. Int J Pharm. 225(1–2):113–121.
   PubMedGoogle Scholar
• Butani D, Yewale C, Misra A. 2014. Amphotericin B topical microemulsion: formulation, characterization and evaluation. Colloids Surf B Biointerfaces. 116:351–358.
   PubMed Web of Science ®Google Scholar
• Carroll N. 2010. A review of transdermal nonpatch estrogen therapy for the management of menopausal symptoms. J Womens Health. 19(1):47–55.
   Web of Science ®Google Scholar
• Chansakaow S, Ishikawa T, Seki H, Sekine K, Okada M, Chaichantipyuth C. 2000. Identification of deoxymiroestrol as the actual rejuvenating principle of “Kwao Keur”, Pueraria mirifica. The known miroestrol may be an artifact. J Nat Prod. 63(2):173–175.
   PubMed Web of Science ®Google Scholar
• Cherdshewasart W, Panriansaen R, Picha P. 2007. Pretreatment with phytoestrogen-rich plant decreases breast tumor incidence and exhibits lower profile of mammary ERalpha and ERbeta. Maturitas. 58(2):174–181.
   PubMed Web of Science ®Google Scholar
• Cherdshewasart W, Sriwatcharakul S, Malaivijitnond S. 2008. Variance of estrogenic activity of the phytoestrogen-rich plant. Maturitas. 61(4):350–357.
   PubMed Web of Science ®Google Scholar
• Cherdshewasart W, Sutjit W, Pulcharoen K, Chulasiri K. 2009. The mutagenic and antimutagenic effects of the traditional phytoestrogen-rich herbs, Pueraria mirifica and Pueraria lobata. Braz J Med Biol Res. 42(9):816–823.
   PubMed Web of Science ®Google Scholar
• Chien YW. 1992. Novel drug delivery systems. 2nd ed. New York: Marcel Dekker, Transdermal drug delivery and delivery systems; p. 301–380.
   Google Scholar
• Csizmazia E, Erős G, Berkesi O, Berkó S, Szabó-Révész P, Csányi E. 2011. Pénétration enhancer effect of sucrose laurate and Transcutol on ibuprofen. J Drug Deliv Sci Technol. 21(5):411–415.
   Web of Science ®Google Scholar
• Da Silva VV, Ropke CD, de Almeida RL, Miranda DV, Kera CZ, Rivelli DP, Sawada TCH, Barros SBM. 2005. Chemical stability and SPF determination of Pothomorphe umbellata extract gel and photostability of 4-nerolidylcathecol. Int J Pharm. 303(1–2):125–131.
   PubMedGoogle Scholar
• Dua K, Pabreja K, Ramana M. 2010. Aceclofenac topical dosage forms: in vitro and in vivo characterization. Acta Pharm. 60(4):467–478.
   PubMed Web of Science ®Google Scholar
• El Gendy AM, Jun HW, Kassem AA. 2002. In vitro release studies of flurbiprofen from different topical formulations. Drug Dev Ind Pharm. 28(7):823–831.
   PubMed Web of Science ®Google Scholar
• Engelbrecht TN, Demé B, Dobner B, Neubert RHH. 2012. Study of the influence of the penetration enhancer isopropyl myristate on the nanostructure of Stratum corneum lipid model membranes using neutron diffraction and deuterium labelling. Skin Pharmacol Physiol. 25(4):200–207.
   PubMed Web of Science ®Google Scholar
• Femenía-Font A, Balaguer-Fernández C, Merino V, Rodilla V, López-Castellano A. 2005. Effect of chemical enhancers on the in vitro percutaneous absorption of sumatriptan succinate. Eur J Pharm Biopharm. 61(1-2):50–55.
   PubMed Web of Science ®Google Scholar
• Fetih G. 2010. Meloxicam formulations for transdermal delivery: hydrogels versus organogels. J Drug Deliv Sci Technol. 20(6):451–456.
   Web of Science ®Google Scholar
• Forbes CJ, Lowry D, Geer L, Veazey RS, Shattock RJ, Klasse PJ, Mitchnick M, Goldman L, Doyle LA, Muldoon BCO, et al. 2011. Non-aqueous silicone elastomer gels as a vaginal microbicide delivery system for the HIV-1 entry inhibitor maraviroc. J Control Release. 156(2):161–169.
   PubMed Web of Science ®Google Scholar
• International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use. 2003. ICH harmonised tripartite guideline: stability testing of new drug substances and products Q1A(R2). Available from https://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q1A_R2/Step4/Q1A_R2__Guideline.pdf/.
   Google Scholar
• Jantharaprapap R, Stagni G. 2007. Effects of penetration enhancers on in vitro permeability of meloxicam gels. Int J Pharm. 343(1–2):26–33.
   PubMed Web of Science ®Google Scholar
• Jones HEM, Waynforth HB, Pope GSJ. 1961. The effect of miroestrol on vaginal cornification, pituitary function and pregnancy in the rat. J Endocrinol. 22(3):293–302.
   PubMed Web of Science ®Google Scholar
• Kaur D, Singh R. 2015. A novel approach: transdermal gel. Int J Pharm Res Rev. 4(10):41–50.
   Google Scholar
• Lawrence MJ, Rees GD. 2000. Microemulsion-based media as novel drug delivery systems. Adv Drug Deliv Rev. 45(1):89–121.
   PubMed Web of Science ®Google Scholar
• Leopold CS, Lippold BC. 1995. An attempt to clarify the mechanism of the penetration enhancing effects of lipophilic vehicles with differential scanning calorimetry (DSC). J Pharm Pharmacol. 47(4):276–281.
   PubMed Web of Science ®Google Scholar
• Liu C-H, Chang F-Y, Hung D-K. 2011. Terpene microemulsions for transdermal curcumin delivery: effects of terpenes and cosurfactants. Colloids Surf B Biointerfaces. 82(1):63–70.
   PubMed Web of Science ®Google Scholar
• Malaivijitnond S, Chansri K, Kijkuokul P, Urasopon N, Cherdshewasart W. 2006. Using vaginal cytology to assess the estrogenic activity of phytoestrogen-rich herb. J Ethnopharmacol. 107(3):354–360.
   PubMed Web of Science ®Google Scholar
• Malladi R, Stahlman J, inventors. 2005. Besins Healthcare Luxembourg SARL Unimed Pharmaceuticals LLC, assignee. Oct 12. Testosterone gel and method of use. United States patent US 8,754,070B2.
   Google Scholar
• Maske PP, Lokapure SG, Nimbalkar D, Malavi S, D'souza JI. 2013. In vitro determination of sun protection factor and chemical stability of Rosa kordesii extract gel. J Pharm Res. 7(6):520–524.
   Google Scholar
• Matsumura A, Ghosh A, Pope GS, Darbre PD. 2005. Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. J Steroid Biochem Mol Biol. 94(5):431–443.
   PubMed Web of Science ®Google Scholar
• Megrab NA, Williams AC, Barry BW. 1995. Oestradiol permeation through human skin and silastic membrane: effects of propylene glycol and supersaturation. J Control Release. 36(3):277–294.
   Web of Science ®Google Scholar
• Mishra R, Prabhavalkar KS, Bhatt LK. 2016. Preparation, optimization, and evaluation of zaltoprofen-loaded microemulsion and microemulsion-based gel for transdermal delivery. J Liposome Res. 26(4):297–306.
   PubMed Web of Science ®Google Scholar
• Mitragotri S, Anissimov YG, Bunge AL, Frasch HF, Guy RH, Hadgraft J, Kasting GB, Lane ME, Roberts MS. 2011. Mathematical models of skin permeability: an overview. Int J Pharm. 418(1):115–129.
   PubMedGoogle Scholar
• Naik A, Kalia YN, Guy RH. 2000. Transdermal drug delivery: overcoming the skin’s barrier function. Pharm Sci Technol Today. 3(9):318–326.
   PubMedGoogle Scholar
• Narang A, Delmarre D, Gao D. 2007. Stable drug encapsulation in micelles and microemulsions. Int J Pharm. 345(1–2):9–25.
   PubMed Web of Science ®Google Scholar
• OECD. 2002. OECD guideline for testing of chemicals, test no. 404: acute dermal irritation/corrosion. Available from: https://ntp.niehs.nih.gov/iccvam/suppdocs/feddocs/oecd/oecdtg404.pdf.
   Google Scholar
• Özsoy Y, Güngör S, Cevher E. 2004. Vehicle effects on in vitro release of tiaprofenic acid from different topical formulations. Farmaco. 59(7):563–566.
   PubMedGoogle Scholar
• Peltola S, Saarinen-Savolainen P, Kiesvaara J, Suhonen T, Urtti A. 2003. Microemulsions for topical delivery of estradiol. Int J Pharm. 254(2):99–107.
   PubMed Web of Science ®Google Scholar
• Prasanthi D, Lakshmi PK. 2013. Optimisation of transdermal gel formulations of tolterodine tartrate by experimental design. Turk J Pharm Sci. 10(2):273–286.
   Google Scholar
• Rehman K, Zulfakar MH. 2014. Recent advances in gel technologies for topical and transdermal drug delivery. Drug Dev Ind Pharm. 40(4):433–440.
   PubMed Web of Science ®Google Scholar
• Rowe RC, Sheskey PJ, Quinn ME. 2009. Handbook of pharmaceutical excipients. 6th ed. London: Pharmaceutical Press.
   Google Scholar
• Rozman B, Gosenca M, Gasperlin M, Padois K, Falson F. 2010. Dual influence of colloidal silica on skin deposition of vitamins C and E simultaneously incorporated in topical microemulsions. Drug Dev Ind Pharm. 36(7):852–860.
   PubMed Web of Science ®Google Scholar
• Shukla T, Upmanyu N, Agrawal M, Saraf S, Saraf S, Alexander A. 2018. Biomedical applications of microemulsion through dermal and transdermal route. Biomed Pharmacother. 108:1477–1494.
   PubMed Web of Science ®Google Scholar
• Sookvanichsilp N, Soonthornchareonnon N, Boonleang C. 2008. Estrogenic activity of the dichloromethane extract from Pueraria mirifica. Fitoterapia. 79(7-8):509–514.
   PubMed Web of Science ®Google Scholar
• Sucontphunt A, De-Eknamkul W, Nimmannit U, Dan Dimitrijevich S, Gracy RW. 2011. Protection of HT22 neuronal cells against glutamate toxicity mediated by the antioxidant activity of Pueraria candollei var. mirifica extracts. J Nat Med. 65(1):1–8.
   PubMed Web of Science ®Google Scholar
• Udomsin O, Juengwatanatrakul T, Yusakul G, Putalun W. 2015. Chromene stability: the most potent estrogenic compounds in White Kwao Krua (Pueraria candollei var mirifica) crude extract. J Funct Foods. 19(Part A):269–277.
   Google Scholar
• Udomsuk L, Juengwatanatrakul T, Putalun W, Jarukamjorn K. 2012. Bimodal action of miroestrol and deoxymiroestrol, phytoestrogens from Pueraria candollei var. mirifica, on hepatic CYP2B9 and CYP1A2 expressions and antilipid peroxidation in mice. Nutr Res. 32(1):45–51.
   PubMed Web of Science ®Google Scholar
• Urasopon N, Hamada Y, Asaoka K, Cherdshewasart W, Malaivijitnond S. 2007. Pueraria mirifica, a phytoestrogen-rich herb, prevents bone loss in orchidectomized rats. Maturitas. 56(3):322–331.
   PubMed Web of Science ®Google Scholar
• Urasopon N, Hamada Y, Cherdshewasart W, Malaivijitnond S. 2008. Preventive effects of Pueraria mirifica on bone loss in ovariectomized rats. Maturitas. 59(2):137–148.
   PubMed Web of Science ®Google Scholar
• US EPA 2012. Estimation Programs Interface Suite™ for Microsoft^® Windows, v 4.11. Washington (DC): United States Environmental Protection Agency.
   Google Scholar
• Wang J, Li Z, Sun F, Tang S, Zhang S, Lv P, Li J, Cao X. 2017. Evaluation of dermal irritation and skin sensitization due to vitacoxib. Toxicol Rep. 4:287–290.
   PubMed Web of Science ®Google Scholar
• Wattanapitayakul SK, Chularojmontri L, Srichirat S. 2005. Effects of Pueraria mirifica on vascular function of ovariectomized rabbits. J Med Assoc Thai. 88(Suppl 1):S21–S29.
   PubMedGoogle Scholar
• Williams AC, Barry BW. 2004. Penetration enhancers. Adv Drug Deliv Rev. 56(5):603–618.
   PubMed Web of Science ®Google Scholar
• You J, Meng S, Ning Y-K, Yang L-Q, Zhang XW, Wang H-N, Li J-J, Yin F-M, Liu J, Zhai Z-Y, et al. 2019. Development and application of an osthole microemulsion hydrogel for external drug evaluation. J Drug Deliv Sci Technol. 54:101331.
   Web of Science ®Google Scholar
• Yusakul G, Putalun W, Udomsin O, Juengwatanatrakul T, Chaichantipyuth C. 2011. Comparative analysis of the chemical constituents of two varieties of Pueraria candollei. Fitoterapia. 82(2):203–207.
   PubMed Web of Science ®Google Scholar
• Yusakul G, Udomsin O, Juengwatanatrakul T, Tanaka H, Chaichantipyuth C, Putalun W. 2013. High performance enzyme-linked immunosorbent assay for determination of miroestrol, a potent phytoestrogen from Pueraria candollei. Anal Chim Acta. 785:104–110.
   PubMed Web of Science ®Google Scholar
• Zhang X, Wu Y, Hong Y, Zhu X, Lin L, Lin Q. 2015. Preparation and evaluation of dl-praeruptorin A microemulsion based hydrogel for dermal delivery. Drug Deliv. 22(6):757–764.
   PubMed Web of Science ®Google Scholar
• Zidan AS, Kamal N, Alayoubi A, Seggel M, Ibrahim S, Rahman Z, Cruz CN, Ashraf M. 2017. Effect of isopropyl myristate on transdermal permeation of testosterone from carbopol gel. J Pharm Sci. 106(7):1805–1813.
   PubMed Web of Science ®Google Scholar