Influencing Factors of Drug Crystal and its Screening Control Strategy
SHI Jun-feng1,2, WANG Dan2, TIAN Yang2, WANG Zeng-ming2, ZHENG Ai-ping2, ZHANG Hui2*, XIANG Mei-xian1*
1. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074,China; 2. Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences, Academy of Military Sciences, Beijing 100850,China
Abstract:Drug crystal is an important factor affecting drug properties, stability, quality controllability, clinical efficacy and safety. Drug crystal not only limits the clinical application of drugs, but also makes the clinical application of drugs more selective. Therefore, it is very important to know the influencing factors of drug crystal and master the control strategy of crystal. According to the forming process of crystal, the influencing factors of drug crystal and the strategy of controlling drug crystal were reviewed, hoping to provide guidance for the selection and quality control of drug crystal in drug research.
师军凤, 王丹, 田阳, 王增明, 郑爱萍, 张慧, 向梅先. 药物晶型的影响因素及其筛选控制策略[J]. 中国药学杂志, 2022, 57(22): 1873-1880.
SHI Jun-feng, WANG Dan, TIAN Yang, WANG Zeng-ming, ZHENG Ai-ping, ZHANG Hui, XIANG Mei-xian. Influencing Factors of Drug Crystal and its Screening Control Strategy. Chinese Pharmaceutical Journal, 2022, 57(22): 1873-1880.
MAO L, ZHENG Q T, LV Y. Progress on the study of solid drug polymorphism. Nat Prod Res Dev(天然产物研究与开发), 2005, 17(3): 371-375.
[2]
LV Y, DU G H. Crystalline drug(晶型药物).Beijing: People′s Medical Publishing House Co., LTD, 2009: 6-7.
[3]
ZHENG L L. Effect of drug polycrystalline on drug quality. China Pharm(中国药师), 2008,(3): 347-349.
[4]
YANG S Y, ZHOU J, ZHANG L, et al. Present situation and progress of the research for polymorphic chemical drugs in China. Her Med (医药导报), 2019, 38(2): 177-182.
[5]
MACHER A, CROKER D M, SEATON C C, et al. Solution-mediated polymorphic transformation: form Ⅱ to form Ⅲ piracetam in organic solvents . Cryst Growth Des, 2014, 14(8): 3967-3974.
[6]
LU M, GONG Y, DU W, et al. The effect of solvent on crystal transformation process of prasugrelhydrogen sulfate and its mechanism. Chin J New Drugs(中国新药杂志), 2021, 30(17): 1616-1620.
[7]
CHEN J. Research progress of drug polymorphic transformation factors. Tianjin Pharm (天津药学), 2018, 30(6): 44-48.
[8]
AN J H, CHOI G J, KIM W S. Polymorphic and kinetic investigation of adefovirdipivoxil during phase transformation. Int J Pharm, 2012, 422(1-2): 185-193.
[9]
PAISANA M C, WAHL M A, PINTO J F. Role of moisture on the physical stability of polymorphic olanzapine. Int J Pharm, 2016, 509(1-2): 135-148.
[10]
XIN C F, JING W L, YU L, et al. Optimization of crystallization conditions of lactitol. Food Res Dev(食品研究与开发), 2016, 37(3): 129-131.
[11]
LU H B, GENG L, WANG P, et al. Effects of cooling rates and stirring speeds on the crystalline form of febuxostat. Acta Acad Med Xuzhou(徐州医科大学学报),2015,(12):855-857.
[12]
BRITTAIN H G. Effects of mechanical processing on phase composition. J Pharm Sci, 2002, 91(7): 1573-1580.
[13]
WILLART J F, DESCAMPS M. Solid state amorphization of pharmaceuticals. Mol Pharmacol, 2008, 5(6): 905-920.
[14]
ZHANG P, YANG C H, LIU J H, et al. Advances in the studies on the drug polymorphs. Strait Pharm J(海峡药学), 2013, 25(12): 5-8.
[15]
LIN S Y, HSU C H, KE W T. Solid-state transformation of different gabapentin polymorphs upon milling and co-milling. Int J Pharm, 2010, 396(1-2): 83-90.
[16]
CHEN J X. Study on telmisartan polycrystalline and its crystallization and properties . Zhengzhou:Henan University of Technology, 2015.
[17]
SOMANI R H, HSIAO B S, NOGALES A, et al. Structure development during shear flow-induced crystallization of i-PP: in-situ small-angle X-ray scattering study. Macromolecules, 2000, 33(25): 9385-9394.
[18]
SYPEK K, BURNS I S, FLORENCE A J, et al. In situ monitoring of stirring effects on polymorphic transformations during cooling crystallization of carbamazepine. Cryst Growth Des, 2012, 12(10): 4821-4828.
[19]
GAO J, TENG Z J, SHU J H, et al. Drug polymorphic transformation during manufacturing process of solid dosage forms. Chin J New Drugs (中国新药杂志), 2018, 27(9): 1000-1005.
[20]
MARIA V R, JUAN Z D, PILAR J. Effect of pressure on the polymorphic forms of famotidine. Thermochim Acta, 2002, 394(1): 19-24.
[21]
MAZEL V, DELPLACE C, BUSIGNIS V, et al. Polymorphic transformation of anhydrous caffeine under compression and grinding: a re-evaluation. Drug Dev Ind Pharm, 2011, 37(7): 832-840.
[22]
JAMES J D Y, PUPA G, NICO S, et al. Crystallization by particle attachment in synthetic, biogenic, and geologic environments. Science, 2015, 349(6247): aaa6760. Doi: 10.1126/science.aaa6760.
[23]
WATANABE M, MIZOGUCHI M, AOKI H,et al. Saturated fatty acids andfatty acid esters promote the polymorphic transition of clarithromycinmetastable form I crystal.Int J Pharm, 2016, 512(1): 108-117.
[24]
TAKAKO I, FUMITOSHI H, DAISUKE I, et al. Crystallization and polymorphic transitions of chlorpropamide in aqueous 2-hydroxybutyl-β-cyclodextrin solution. Eur J Pharm Sci, 2009, 39(4): 248-255.
[25]
TAMURA R, MIZUTA M, YABUNAKA S, et al. Induction and inhibition of preferential enrichment by controlling the mode of the polymorphic transition with seed crystals. Chemistry, 2006, 12(13): 3515-3527.
[26]
WANG Z. Controllable preparations of polymorphic form of tolfenamic acid and the formation of salt between piperazine and tolfenamic acid. Jinan:Shandong University, 2020.
[27]
INSORN P, KITIYANAN B. Selective hydrogenation of concentrated vinylacetylene mixed C4 by modified Pd catalysts: effect of Cu. Catalysts, 2016, 6(12): 199-210.
[28]
YOUSEF M, VANGALA V. Pharmaceutical co-crystals: molecules, crystals, formulations, medicines. Cryst Growth Des, 2019, 19(12): 7420-7438.
[29]
SCHULTHEISS N, NEWMAN A. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des, 2009, 9(6): 2950-2967.
[30]
SAMIE A, DESIRAJU G, BANNIK M. Salts and cocrystals of antidiabetic drugs, gliclazide, tolbutamide and glipizide: solubility enhancements through drug-coformer interactions. Cryst Growth Des, 2017, 17(5): 2406-2417.
[31]
MORADIVA H, ISLAM M, WOOLLAM G, et al. Continuous cocrystallization for dissolution rate optimization of a poorly water-soluble drug. Cryst Growth Des, 2014, 14(1): 189-198.
[32]
MASUDA T, YOSHIHAHSI Y, YONEMOCHI E, et al. Cocrystallization and amorphization induced by drug-excipient interaction improves the physical properties of acyclovir. Int J Pharm, 2012, 422(1): 160-169.
[33]
JIANG Y H. Use cocrystal technology to improve the physical properties and stability of hydroxytyrosol.Beijing:University of Chinese Academy of Sciences, 2021.
[34]
NEWMAN A. Specialized solid form screening techniques. Org Proc Res Dev, 2013, 17(3): 457-471.
[35]
SRIRAMBHATLA V K, GUO R, PRICE S L, et al.Isomorphous template in-ducedcrystallisation: A robust method for the targeted crystallisation of computationally predicted metastable polymorphs. Chem Comm, 2016, 52(46): 7384-7386.
[36]
CHADWICK K, CHEN J, MYERSON A S, et al. Toward the rational designof crystalline surfaces for heteroepitaxy: Role of molecular function-ality. Cryst Growth Des, 2012, 12(3): 1159-1166.
[37]
PEDRO M V, ERIC M P, MINSOUNG R, et al. Microfluidic platform for combinatorial synthesis and optimization of targeted nanoparticles for cancer therapy. ACS Nano, 2013, 7(12): 10671-10680.
[38]
DUNCANSON W J, LIN T, ABATE A R, et al. Microfluidic synthesis of advanced microparticles for encapsulation and controlled release. Lab Chip, 2012, 12(12): 2135-2145.
[39]
JEBRAIL M J, BARTSCH M S, PATEL K D. Digital microfluidics: A versatile tool for applications in chemistry, biology and medicine. Lab Chip, 2012, 12(14): 2452-2463.
[40]
LIU D, ZHANG H, FONTANA F, et al. Microfluidic-assisted fabrication of carriers for controlled drug delivery. Lab Chip, 2017, 17(11): 1856-1883.
[41]
CATHERINE T L, ANDREAS J, LAURIE E L, et al. Controlled self-assembly of monodisperse niosomes by microfluidic hydrodynamic focusing. Langmuir Acs J Surf Coll, 2010, 26(11): 8559-8566.
[42]
HOOD R R, VREELAND W N, DEVOE D L. Microfluidic remote loading for rapid single-step liposomal drug preparation. Lab Chip, 2011, 14(17): 3359-3367.
[43]
BHAMIDI V, LEE S H, HE G, et al. Antisolvent crystallization and polymorph screening of glycine in microfluidic channels using hydrodynamic focusing. Cryst Growth Des, 2015, 15(7): 3299-3306.
[44]
LU J, LITSTER J D, NAGY Z K. Nucleation studies of active pharmaceutical ingredients in an air-segmented microfluidic drop-based crystallizer. Cryst Growth Des,2015, 15(80): 3645-3651.
[45]
GOYAL S, ECONOMOU A, PAPADOUPOLOS T, et al. Solvent compatible microfluidic platforms for pharmaceutical solid form screening. RSC Adv, 2016,6(16): 13286-13296.
[46]
GOYAL S, THORSON M R, ZHANG G G Z, et al. Microfluidic approach to cocrystal screening ofpharmaceutical parent compounds. Cryst Growth Des, 2012, 12(12): 6023-6034.
[47]
SHI H, XIAO Y, FERGUSON S, et al. Progress of crystallization in microfluidic devices. Lab Chip, 2017, 17(13): 2167-2185.
[48]
CHEN K, GOH L, HE G, et al. Identification of nucleation rates in droplet-basedmicrofluidic systems. Chem Eng Sci, 2012, 77: 235-241.
[49]
OUYANG J B, CHEN J, YING X, et al. Research progress on polymorph control of small molecule drugs. Mod Chem Ind(现代化工), 2021, 41(1): 62-66,71.
[50]
THORSON M R, GOYAL S, GONG Y, et al. Microfluidic approach to polymorph screening through antisolvent crystallization. Cryst Eng Comm, 2012, 14: 2404-2412.
[51]
VENKATESWARLU B, LEE SH, HE G, et al. Antisolvent Crystallization and Polymorph Screening of Glycine in Microfluidic Channels Using Hydrodynamic Focusing. Cryst Growth Des, 2015, 15(7): 3299-3306.
[52]
SIMONE E, MCVEIGH J, REIS NM, et al. A high-throughput multi-microfluidic crystal generator(MMicroCryGen)platform for facile screening of polymorphism and crystal morphology for pharmaceutical compounds. Lab Chip, 2018, 18(15): 2235-2245.
[53]
WIJETHUNGA T K, BAFTIZADEH F, STOJAKOVIC J, et al. Experimental and mechanistic study of the heterogeneous nucleation and epitaxy of acetaminophenwith biocompatible crystalline substrates. Cryst Growth Des, 2017, 17(7): 3783-3795.
[54]
HENG T, YANG D, WANG R, et al. Progress in Research on Artificial Intelligence Applied to Polymorphism and Cocrystal Prediction. ACS Omega, 2021, 6(24): 15543-15550.
[55]
JOHNSTON A, JOHNSTON B F, KENNEDY A R, et al.Targeted crystallisation of novel carbamazepine solvates based on aretrospective random forest classification. Cryst Eng Comm, 2008, 10(1): 23-25.
[56]
XIN D, GONNELLA N C, HE X, et al. Solvate prediction for pharmaceutical organic molecules with machine learning. Cryst Growth Des, 2019, 19: 1903-1911.
[57]
CLYDESDALE G, DOCHERTY R, ROBERTS K J. HABIT-a program for predicting the morphology of molecular crystals.Comp Phys Comm, 1991, 64(2):311-328.
[58]
HOLLEMAN E T, DUGUID E, KEEFE L J, et al. Polo: an open-source graphical user interface for crystallization screening. J Appl Crystallogr, 2021, 54(2): 673-679.
[59]
WANG Y Y, YANG Y J, LIU M M, et al. Phenomenon and progress on the study of solid drug polymorphism. Shandong Chem Ind(山东化工), 2021, 50(3): 79-80.
[60]
ZHANG W J, LI D H, LV C Y, et al. Application progress of drug crystal forms in drug research. J Pharm Res, 2021, 40(4): 266-271.
[61]
DU C, LIU XN, TANG Y, et al. Comparative study of thermal stability and crystal form of bendamustine hydrochloride. J Yichun Univ(宜春学院学报), 2021, 43(6): 38-42.
[62]
ROSA P, CHIARA S, GUIDO E, et al. The effect of diethylene glycol monoethyl ether on skin penetration ability of diclofenac acid nanosuspensions. Coll Surf B Biointerfaces, 2018, 162: 8-15.
[63]
LIANG Y, XING C, ZHOU Q M, et al. Preparation of three crystals of mifepristone and its pharmacokinetics in rats. Chin New Drugs J(中国新药杂志), 2020, 29(19): 2251-2259.