Progress in pharmaceutical crystallographic study of mannitol
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摘要:
甘露醇作为一种药用辅料，具备热值低、引湿性低、稳定性高等性质，广泛应用于固体制剂、冻干制剂和吸入制剂等多种剂型中，其具有不同晶体结构的晶型（α，β和δ）和共晶，晶体结构的改变会影响药物的制剂性能。本文从甘露醇多晶型的结构特征、物理化学性质、制备方法以及共晶形成等方面进行了综述，并着重讨论了甘露醇多晶型之间的转变条件、监测方法以及晶型转变对制剂性能的影响，包括可成片性和崩解溶出性能等。通过对甘露醇晶体学研究的系统性总结，以期为新型药用辅料开发及在药物制剂中的应用提供新思路。
Abstract:As a pharmaceutical excipient with low caloric value, low hygroscopicity, and high stability, mannitol is widely used in various dosage forms, such as solid, lyophilized and inhalation preparations, etc. It has different crystal structures (α, β and δ) and cocrystal, and the changes in the crystal structure will affect formulation properties of pharmaceutical formulations. This paper reviews structural features, physicochemical properties, and preparation methods of mannitol polymorphs and cocrystal formation, with emphasis on polymorphic transformation pathways, monitoring methods and the effect of polymorphic transformation on properties and application in pharmaceutical formulations, including tabletability, disintegration and dissolution properties. By systematically summarizing the crystallographic study of mannitol, this study attempts to provide new ideas for the development of novel pharmaceutical excipients and applications in pharmaceutical formulations.
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Keywords:
- mannitol /
- polymorph /
- cocrystal /
- polymorphic transform /
- pharmaceutical excipient
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[1] Yang YX, Liu J, Hu AN, et al. A critical review on engineering of d-mannitol crystals: properties, applications, and polymorphic control[J]. Crystals, 2022, 12(8): 1080-1101. doi: 10.3390/cryst12081080
[2] Shao XF, Yang S, Fan LW, et al. Sugar alcohol phase change materials for low-to-medium temperature thermal energy storage: a comprehensive review[J]. J Energy Storage, 2023, 68: 107848. doi: 10.1016/j.est.2023.107848
[3] Poka MS, Milne M, Wessels A, et al. Sugars and polyols of natural origin as carriers for solubility and dissolution enhancement[J]. Pharmaceutics, 2023, 15(11): 2557-2585. doi: 10.3390/pharmaceutics15112557
[4] Farfan Pajuelo DG, Carpio Mamani M, Maraza Choque GJ, et al. Effect of lyoprotective agents on the preservation of survival of a bacillus cereus strain PBG in the freeze-drying process[J]. Microorganisms, 2023, 11(11): 2705-2722. doi: 10.3390/microorganisms11112705
[5] Drago SE, Cabibbo M, Craparo EF, et al. TAT decorated si-RNA polyplexes for inhalation delivery in anti-asthma therapy[J]. Eur J Pharm Sci, 2023, 190: 106580. doi: 10.1016/j.ejps.2023.106580
[6] Thakral S, Sonje J, Munjal B, et al. Mannitol as an excipient for lyophilized injectable formulations[J]. J Pharm Sci, 2023, 112(1): 19-35. doi: 10.1016/j.xphs.2022.08.029
[7] Cheng H, Wei YF, Wang SR, et al. Improving tabletability of excipients by metal-organic framework-based cocrystallization: a study of mannitol and CaCl2[J]. Pharm Res, 2020, 37(7): 130-144. doi: 10.1007/s11095-020-02850-8
[8] Sonje J, Thakral S, Mayhugh B, et al. Mannitol hemihydrate in lyophilized protein formulations: impact of its dehydration during storage on sucrose crystallinity and protein stability[J]. Int J Pharm, 2022, 624: 121974. doi: 10.1016/j.ijpharm.2022.121974
[9] Thakral S, Sonje J, Suryanarayanan R. Anomalous behavior of mannitol hemihydrate: implications on sucrose crystallization in colyophilized systems[J]. Int J Pharm, 2020, 587: 119629. doi: 10.1016/j.ijpharm.2020.119629
[10] Saha BK, Nath NK, Thakuria R. Polymorphs with remarkably distinct physical and/or chemical properties[J]. Chem Rec, 2023, 23(1): 202200173. doi: 10.1002/tcr.202200173
[11] Braga D, Casali L, Grepioni F. The relevance of crystal forms in the pharmaceutical field: sword of damocles or innovation tools?[J]. Int J Mol Sci, 2022, 23(16): 9013-9042. doi: 10.3390/ijms23169013
[12] Vanhoorne V, Almey R, De Beer T, et al. Delta-mannitol to enable continuous twin-screw granulation of a highly dosed, poorly compactable formulation[J]. Int J Pharm, 2020, 583: 119374. doi: 10.1016/j.ijpharm.2020.119374
[13] Burger A, Henck JO, Hetz S, et al. Energy/temperature diagram and compression behavior of the polymorphs of d-mannitol[J]. J Pharm Sci, 2000, 89(4): 457-468. doi: 10.1002/(SICI)1520-6017(200004)89:4<457::AID-JPS3>3.0.CO;2-G
[14] Yu L, Huang J, Jones KJ. Measuring free-energy difference between crystal polymorphs through eutectic melting[J]. J Phys Chem B, 2005, 109(42): 19915-19922. doi: 10.1021/jp053653g
[15] Cornel J, Kidambi P, Mazzotti M. Precipitation and transformation of the three polymorphs of d-mannitol[J]. Ind Eng Chem Res, 2010, 49(12): 5854-5862. doi: 10.1021/ie9019616
[16] Su W, Liu J, Wang H, et al. Thermodynamic study of three anhydrous polymorphs of d-mannitol in different binary solvent mixtures from T = (258.15 to 278.15) K[J]. J Chem Thermodyn, 2020, 141: 105680. doi: 10.1016/j.jct.2019.01.005
[17] Mareczek L, Riehl C, Harms M, et al. Understanding the multidimensional effects of polymorphism, particle size and processing for d-mannitol powders[J]. Pharmaceutics, 2022, 14(10): 2128-2147. doi: 10.3390/pharmaceutics14102128
[18] Wagner CM, Pein M, Breitkreutz J. Roll compaction of granulated mannitol grades and the unprocessed crystalline delta-polymorph[J]. Powder Technol, 2015, 270: 470-475. doi: 10.1016/j.powtec.2014.03.073
[19] Chettri A, Subba A, Singh GP, et al. Pharmaceutical co-crystals: a green way to enhance drug stability and solubility for improved therapeutic efficacy[J]. J Pharm Pharmacol, 2023: rgad097.
[20] Liu J, Klinzing GR, Nie H. Effect of material properties and variability of mannitol on tablet formulation development[J]. Pharm Res, 2023, 40(8): 2071-2085. doi: 10.1007/s11095-023-03577-y
[21] Zhang JJ, Zhang ZF, Cheng H, et al. Mannitol calcium bromide cocrystal and its preparation method and application: CN112110795A[P]. 2020-12-22.
[22] Peng W, Lin Z, Cao W, et al. Crystal defects creation in mannitol@CaCl2 metal–organic framework by induced dehydration strategy for enhanced excipient mechanical properties[J]. Int J Pharm, 2024, 652: 123837. doi: 10.1016/j.ijpharm.2024.123837
[23] Wen X, Wang S, Ramji R, et al. Complete inhibition of a polyol nucleation by a micromolar biopolymer additive[J]. Cell Rep Phys Sci, 2022, 3(2): 100723. doi: 10.1016/j.xcrp.2021.100723
[24] Penha FM, Gopalan A, Meijlink JC, et al. Selective crystallization of d-mannitol polymorphs using surfactant self-assembly[J]. Cryst Growth Des, 2021, 21(7): 3928-3935. doi: 10.1021/acs.cgd.1c00243
[25] Abdullahi H, Neoptolemou P, Burcham CL, et al. Single droplets to particles-size, shape, shell thickness and porosity analyses using X-ray computed tomography[J]. Chem Eng Sci, 2021, 245: 116879. doi: 10.1016/j.ces.2021.116879
[26] Badal Tejedor M, Fransson J, Millqvist Fureby A. Freeze-dried cake structural and physical heterogeneity in relation to freeze-drying cycle parameters[J]. Int J Pharm, 2020, 590: 119891. doi: 10.1016/j.ijpharm.2020.119891
[27] Su WY, Zhang Y, Liu JM, et al. Molecular dynamic simulation of d-mannitol polymorphs in solid state and in solution relating with spontaneous nucleation[J]. J Pharm Sci, 2020, 109(4): 1537-1546. doi: 10.1016/j.xphs.2020.01.012
[28] Yao CL, Zhang SF, Wang L, et al. Recent advances in polymorph discovery methods of organic crystals[J]. Cryst Growth Des, 2023, 23(1): 637-654. doi: 10.1021/acs.cgd.2c00960
[29] Tang X, Ryu J. Polymorphism of d-mannitol in zeolite-added d-mannitol-based phase change materials and its effect on supercooling degree[J]. Int J Thermophys, 2023, 44(4): 58-76. doi: 10.1007/s10765-023-03171-9
[30] Neumann H, Niedermaier S, Gschwander S, et al. Cycling stability of d-mannitol when used as phase change material for thermal storage applications[J]. Thermochimica Acta, 2018, 660: 134-143. doi: 10.1016/j.tca.2017.12.026
[31] Altay Benetti A, Bianchera A, Buttini F, et al. Mannitol polymorphs as carrier in DPIs formulations: isolation characterization and performance[J]. Pharmaceutics, 2021, 13(8): 1113-1134. doi: 10.3390/pharmaceutics13081113
[32] De Pauw E, Vervaet C, Vanhoorne V. Formation of delta-mannitol by co-spray drying: enhancing the tabletability of paracetamol/mannitol formulations[J]. J Drug Deliv Sci Technol, 2022, 77: 103907. doi: 10.1016/j.jddst.2022.103907
[33] Gao Y, Cheng H, Wang S, et al. Mannitol cocrystal excipient and its preparation method and use: CN111166891B[P]. 2022-04-05.
[34] Gao Y, Li ZD, Zhang ZF, et al. A preparation method suitable for industrial scale-up production of mannitol cocrystal excipients: CN113788849A[P]. 2021-12-14.
[35] Park H, Kim JS, Hong S, et al. Tableting process-induced solid-state polymorphic transition[J]. J Pharm Investig, 2022, 52(2): 175-194. doi: 10.1007/s40005-021-00556-6
[36] Shi Q, Chen HB, Wang YN, et al. Recent advances in drug polymorphs: aspects of pharmaceutical properties and selective crystallization[J]. Int J Pharm, 2022, 611: 121320. doi: 10.1016/j.ijpharm.2021.121320
[37] Bruni G, Berbenni V, Milanese C, et al. Physico-chemical characterization of anhydrous d-mannitol[J]. J Therm Anal, 2009, 95(3): 871-876. doi: 10.1007/s10973-008-9384-5
[38] Dierks TM, Korter TM. Origins of the relative stabilities of anhydrous and hydrated d-mannitol crystals[J]. J Phys Chem A, 2016, 120(33): 6629-6636. doi: 10.1021/acs.jpca.6b05244
[39] Buanz A, Gurung M, Gaisford S. Crystallisation in printed droplets: understanding crystallisation of d-mannitol polymorphs[J]. CrystEngComm, 2019, 21(13): 2212-2219. doi: 10.1039/C8CE01780H
[40] Zhu Y, Lu MJ, Gao F, et al. Role of tailor-made additives in crystallization from solution: a review[J]. Ind Eng Chem Res, 2023, 62(12): 4800-4816. doi: 10.1021/acs.iecr.2c04025
[41] Yoshinari T, Forbes RT, York P, et al. Moisture induced polymorphic transition of mannitol and its morphological transformation[J]. Int J Pharm, 2002, 247(1): 69-77.
[42] Descamps M, Willart JF, Dudognon E, et al. Transformation of pharmaceutical compounds upon milling and comilling: the role of Tg[J]. J Pharm Sci, 2007, 96(5): 1398-1407. doi: 10.1002/jps.20939
[43] Martinetto P, Bordet P, Descamps M, et al. Structural transformations of d-mannitol induced by in situ milling using real time powder synchrotron radiation diffraction[J]. Cryst Growth Des, 2017, 17(11): 6111-6122. doi: 10.1021/acs.cgd.7b01283
[44] Pinto JT, Zellnitz S, Guidi T, et al. Spray-congealing and wet-sieving as alternative processes for engineering of inhalation carrier particles: comparison of surface properties, blending andin vitro performance[J]. Pharm Res, 2021, 38(6): 1107-1123. doi: 10.1007/s11095-021-03061-5
[45] Valentin M, Coibion D, Vertruyen B, et al. Macroporous mannitol granules produced by spray drying and sacrificial templating[J]. Materials, 2023, 16(1): 25-41.
[46] Acevedo D, Wu WL, Yang X, et al. Evaluation of focused beam reflectance measurement (FBRM) for monitoring and predicting the crystal size of carbamazepine in crystallization processes[J]. CrystEngComm, 2021, 23(4): 972-985. doi: 10.1039/D0CE01388A
[47] O'sullivan B, Glennon B. Application ofin situ FBRM and ATR-FTIR to the monitoring of the polymorphic transformation of d-mannitol[J]. Org Process Res Dev, 2005, 9(6): 884-889. doi: 10.1021/op0500887
[48] Su WY, Hao HX, Barrett M, et al. The impact of operating parameters on the polymorphic transformation of d-mannitol characterized in situ with Raman spectroscopy, FBRM, and PVM[J]. Org Process Res Dev, 2010, 14(6): 1432-1437. doi: 10.1021/op100228f
[49] Yoshinari T, Forbes RT, York P, et al. The improved compaction properties of mannitol after a moisture-induced polymorphic transition[J]. Int J Pharm, 2003, 258(1): 121-131.
[50] Megarry A, Taylor A, Gholami A, et al. Twin-screw granulation and high-shear granulation: the influence of mannitol grade on granule and tablet properties[J]. Int J Pharm, 2020, 590: 119890. doi: 10.1016/j.ijpharm.2020.119890
[51] Li GX, Gu WW, Li KK. Application of delta-mannitol in oral solid preparations after physical modification[J]. Guangdong Chem Ind (广东化工), 2022, 49(13): 44-46. [52] Zajc N, Obreza A, Bele M, et al. Physical properties and dissolution behaviour of nifedipine/mannitol solid dispersions prepared by hot melt method[J]. Int J Pharm, 2005, 291(1): 51-58.
[53] Lenschow ICS, Bazzo GC, Zétola M, et al. Ball-milled valsartan and its combination with mannitol: the case of drug polyamorphism[J]. J Therm Anal, 2022, 147(16): 8765-8777. doi: 10.1007/s10973-021-11164-9
[54] Cares-Pacheco MG, Vaca-Medina G, Calvet R, et al. Physicochemical characterization of d-mannitol polymorphs: the challenging surface energy determination by inverse gas chromatography in the infinite dilution region[J]. Int J Pharm, 2014, 475(1): 69-81.
[55] Han J, Li L, Su M, et al. Deaggregation and crystallization inhibition by small amount of polymer addition for a co-amorphous curcumin-magnolol system[J]. Pharmaceutics, 2021, 13(10): 1725-1749. doi: 10.3390/pharmaceutics13101725
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