The comparison researches of cis/trans-butenedioic acids in regulating solid crystalline forms and improving pharmaceutical properties of antifungal drug econazole

Journal of Molecular Structure - Tập 1263 - Trang 133183 - 2022
Meng-Yao Wu1, Fan-Zhi Bu1,2, Yu Yu3, Yue-Ming Yu1, Zhi-Yong Wu1,2, Cui-Wei Yan1, Yan-Tuan Li1,2
1School of Medicine and Pharmacy and College of Marine Life Science, Ocean University of China, Qingdao, Shandong 266003, China
2Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, 266003, China
3Qingdao Institute for Food and Drug Control, Qingdao, Shandong 266071, China

Tài liệu tham khảo

Chen, 2020, Comparison of the next-generation sequencing (NGS) technology with culture methods in the diagnosis of bacterial and fungal infections, J. Thorac. Dis., 12, 4924, 10.21037/jtd-20-930 Brown, 2012, Hidden killers: human fungal infections, Sci. Transl. Med., 4, 165rv13, 10.1126/scitranslmed.3004404 Pereira, 2021, A review of recent research on antifungal agents against dermatophyte biofilms, Med. Mycol., 59, 313, 10.1093/mmy/myaa114 Maksimov, 2021, Organic antifungal drugs and targets of their action, Curr. Top. Med. Chem., 21, 705, 10.2174/1568026621666210108122622 Milne, 1982, A clinical study of econazole cream in the treatment of fungal skin infections, J. R. Coll. Gen. Pract., 32, 360 Prajna, 2003, A randomised clinical trial comparing 2% econazole and 5% natamycin for the treatment of fungal keratitis, Brit. J. Ophthalmol., 87, 1235, 10.1136/bjo.87.10.1235 Osser, 1991, Treatment of candidal vaginitis: a prospective randomized investigator- blind multicenter study comparing topically applied econazole with oral fluconazole, Acta Obstet. Gyn. Scan., 70, 73, 10.3109/00016349109006182 Mura, 2001, Multicomponent systems of econazole with hydroxyacids and cyclodextrins, J. Incl. Phenom. Macrocycl., 39, 131, 10.1023/A:1008114411503 Al-Marzouqi, 2008, Influence of the preparation method on the physico- chemical properties of econazole-β-cyclodextrin complexes, J. Incl. Phenom. Macro., 60, 85, 10.1007/s10847-007-9356-6 Srivastava, 2021, Formulation development, in vitro and in vivo evaluation of topical hydrogel formulation of econazole nitrate-loaded β-cyclodextrin nanosponges, J. Pharm. Sci. U. S. A., 110, 3702, 10.1016/j.xphs.2021.07.008 Sudhakar, 2021, Ultraflexible liposome nanocargo as a dermal and transdermal drug delivery system, Nanomater. Basel, 11, 2557, 10.3390/nano11102557 Díaz-Tomé, 2018, Ophthalmic econazole hydrogels for the treatment of fungal keratitis, J. Pharm. Sci. U. S. A., 107, 1342, 10.1016/j.xphs.2017.12.028 Kim, 2012, Design and synthesis of 1H-1, 2, 3-triazoles derived from econazole as antitubercular agents, Bioorg. Med. Chem. Lett., 22, 6844, 10.1016/j.bmcl.2012.09.041 Davis, 1998, Azolidene carbenes derived from biologically relevant molecules. Synthesis and characterization of iridium complexes of imidazolidene ligands based upon the antifungal drugs econazole and miconazole, Inorg. Chem., 37, 5412, 10.1021/ic9806277 Wang, 2021, A novel crystalline molecular salt of sulfamethoxazole and amantadine hybridizing antiviral-antibacterial dual drugs with optimal in vitro/vivo pharmaceutical properties, Eur. J. Pharm. Sci., 163, 10.1016/j.ejps.2021.105883 Karimi-Jafari, 2018, Creating cocrystals: a review of pharmaceutical cocrystal preparation routes and applications, Cryst. Growth Des., 18, 6370, 10.1021/acs.cgd.8b00933 Tullio, 1990, In vitro antifungal activities of new imidazole salts towards dermatophytes, Mycoses, 33, 257, 10.1111/myc.1990.33.5.257 Wyler, 1979, An imidazole derivative (econazole) as an antifungal agent in cell culture systems, In Vitro, 15, 745, 10.1007/BF02618300 Burke, 2002, Escitalopram, Expert Opin. Inv. Drug., 11, 1477, 10.1517/13543784.11.10.1477 van Harten, 1993, Pharmacokinetics of fluvoxamine maleate in patients with liver cirrhosis after single-dose oral administration, Clin. Pharmacokinet., 24, 177, 10.2165/00003088-199324020-00006 Akhlaq, 2018, Pharmacokinetic evaluation of quetiapine fumarate controlled release hybrid hydrogel: a healthier treatment of schizophrenia, Drug Deliv., 25, 916, 10.1080/10717544.2018.1458922 Tsutsumi, 2011, Characterization and evaluation of miconazole salts and cocrystals for improved physicochemical properties, Int. J. Pharmaceut., 421, 230, 10.1016/j.ijpharm.2011.09.034 Évora, 2019, Energetics of glycine cocrystal or salt formation with two regioisomers: fumaric acid and maleic acid, Cryst. Growth Des., 19, 5054, 10.1021/acs.cgd.9b00379 Li, 2019, Mechanism and impact of excipient incompatibility: cross-linking of xanthan gum in pediatric powder-for-suspension formulations, J. Pharm. Sci. U. S. A., 108, 3609, 10.1016/j.xphs.2019.07.005 Aguirre, 2012, An assessment of the ocular safety of excipient maleic acid following intravitreal injection in rabbits, Toxicol. Pathol., 40, 797, 10.1177/0192623312441400 Sheldrick, 2015, Crystal structure refinement with SHELXL, Acta Crystallogr. C, 71, 3, 10.1107/S2053229614024218 Karabacak, 2012, The spectroscopic (FT-Raman, FT-IR, UV and NMR), molecular electrostaticpotential, polarizability and hyperpolarizability, NBO and HOMO-LUMO analysis of monomeric and dimeric structures of 4-chloro-3,5-dinitrobenzoic acid, Spectrochim. Acta A, 93, 33, 10.1016/j.saa.2012.02.110 Lu, 2012, Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem., 33, 580, 10.1002/jcc.22885 Spackman, 2009, Hirshfeld surface analysis, CrystEngComm, 11, 19, 10.1039/B818330A Patil, 2019, Development and validation of RP-HPLC and UV spectroscopic method of econazole in bulk and pharmaceutical dosage form, World J. Pharm. Pharm. Sci., 8, 1037 Heel, 1978, Econazole: a review of its antifungal activity and therapeutic efficacy, Drugs, 16, 177, 10.2165/00003495-197816030-00001 Schär, 1976, Antimicrobial activity of econazole and miconazole in vitro and in experimental candidiasis and aspergillosis, Chemotherapy, 22, 211, 10.1159/000221928 Drago, 2000, Antimycotic activity and phagocytosis effects of econazole in combination with ibuprofen isobuthanol ammonium against vaginal strains, Chemotherapy, 12, 509, 10.1179/joc.2000.12.6.509 Carrillo-Munoz, 1995, In-vitro antifungal activity of sertaconazole, econazole, and bifonazole against candida spp, J. Antimicrob. Chemoth., 36, 713, 10.1093/jac/36.4.713 Aitipamula, 2014, Crystal engineering of tegafur cocrystals: structural analysis and physicochemical properties, Cryst. Growth Des., 14, 6557, 10.1021/cg501469r Albertini, 2009, Polymer-lipid based mucoadhesive microspheres prepared by spray-congealing for the vaginal delivery of econazole nitrate, Eur. J. Pharm. Sci., 36, 591, 10.1016/j.ejps.2008.12.009 Ab Rahman, 2017, Carbamazepine-fumaric acid and carbamazepine-succinic acid co-crystal screening using solution based method, Int. J. Chem. Eng. Appl., 8, 136 Mittapalli, 2015, Soluble salts and cocrystals of clotrimazole, Cryst. Growth Des., 15, 2493, 10.1021/acs.cgd.5b00268 Zhang, 2019, The comparative study of cocrystal/salt in simultaneously improving solubility and permeability of acetazolamide, J. Mol. Struct., 1184, 225, 10.1016/j.molstruc.2019.01.090 Goud, 2012, Fast dissolving eutectic compositions of curcumin, Int. J. Pharmaceut., 439, 63, 10.1016/j.ijpharm.2012.09.045 Lange, 1930, The solubility, specific gravity and index of refraction of aqueous solutions of fumaric, maleic and i-malic acids, J. Am. Chem. Soc., 52, 2602, 10.1021/ja01370a003 Chun, 2013, Characteristics of indomethacin-saccharin (IMC-SAC) co-crystals prepared by an anti-solvent crystallization process, Eur. J. Pharm. Biopharm., 85, 854, 10.1016/j.ejpb.2013.02.007 Fleming, 1977 Hussain, 2018, Crystal engineering of naturally occurring seselin to obtain cocrystal with enhanced anti-leishmanial activity, Hirshfeld surface analysis, and computational insight, Cryst. Growth Des., 18, 4628, 10.1021/acs.cgd.8b00602 Luque, 1990, Comparative study of the molecular electrostatic potential obtained from different wavefunctions. Reliability of the semiempirical MNDO wavefunction, J. Comput. Chem., 11, 416, 10.1002/jcc.540110403 Mckinnon, 2007, Comparison of polymorphic molecular crystal structures through Hirshfeld surface analysis, Cryst. Growth Des., 7, 755, 10.1021/cg060773k Bommaka, 2021, Entacapone polymorphs: crystal structures, dissolution, permeability, and stability, Cryst. Growth Des., 21, 5573, 10.1021/acs.cgd.1c00381 Good, 2009, Solubility advantage of pharmaceutical cocrystals, Cryst. Growth Des., 9, 2252, 10.1021/cg801039j Pescina, 2019, Ex vivo conjunctival retention and transconjunctival transport of poorly soluble drugs using polymeric micelles, Pharmaceutics, 11, 476, 10.3390/pharmaceutics11090476 Chen, 2018, Cocrystals mitigate negative effects of high pH on solubility and dissolution of a basic drug, Cryst. Growth Des., 18, 1355, 10.1021/acs.cgd.7b01206 Júnior, 2020, A new ferulic acid- nicotinamide cocrystal with improved solubility and dissolution performance, J. Pharm. Sci., 109, 1330, 10.1016/j.xphs.2019.12.002 Gopi, 2016, A drug-drug salt-hydrate of norfloxacin and sulfathiazole: enhancement of in vitro biological properties via improved physicochemical properties, Mol. Pharmaceut., 13, 3590, 10.1021/acs.molpharmaceut.6b00320 Baba, 2017, Quantitative prediction of ionization effect on human skin permeability, Int. J. Pharmaceut., 522, 222, 10.1016/j.ijpharm.2017.03.009 Wang, 2020, A sulfathiazole-amantadine hydrochloride cocrystal: the first codrug simultaneously comprising antiviral and antibacterial components, Cryst. Growth Des., 20, 3236, 10.1021/acs.cgd.0c00075