Research Progress in Characterization Methods of Pharmaceutical Cocrystals

doi:10.19803/j.1672-8629.2021.10.23

Abstract

Abstract: Pharmaceutical cocrystals are a new solid form which can improve many physical and chemical properties of active pharmaceutical ingredients. As a potential new drug development technology, pharmaceutical cocrystals have many advantages over single component and compound drugs. In recent years, some pharmaceutical cocrystals have been approved for marketing, so a challenge to regulatory departments of drugs in China is to establish effective quality control methods for pharmaceutical cocrystals. Through the review of characterization methods of pharmaceutical cocrystals, we can find out more about the analytical techniques that can effectively identify pharmaceutical cocrystals so as to provide reference for the establishment of quality standards for pharmaceutical cocrystals.

Key words: cocrystal, characterization, XRD, TA, spectrometry, microscope, NMR, DVS

CLC Number:

R917.799

XIONG Jing, DAI Xialin, HE Lan, WU Xiangxiang. Research Progress in Characterization Methods of Pharmaceutical Cocrystals[J]. Chinese Journal of Pharmacovigilance, 2021, 18(10): 995-999.

References

[1] Chinese Pharmacopoeia Commission.Pharmacopoeia of the People’s Republic of China (Part 4) (中华人民共和国药典(四部))[M]. Beijing: China Medical Science Press, 2020: 476-478.
[2] U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research. Regulatory classification of pharmaceutical co-crystals guidance for industry[EB/OL]. (2018-02)[2020-04-17]. http://www.fda.gov/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/default.htm.
[3] Zhang XM.Synthesis, characterization and properties study of pharmaceutical cocrystal[D]. Jilin: Jilin University, 2016.
[4] Oburn S, Ray O, Macgillivray LR.Elusive nonsolvated cocrystals of Aspirin: two polymorphs with bipyridine discovered with aassistance of mechanochemistry[J]. Crystal Growth & Design, 2018,18(4): 2495-2501.
[5] Dai XL, Li S, Chen JM, et al.Improving the membrane permeability of 5-fluorouracil via cocrystallization[J]. Crystal Growth & Design, 2016, 16(8): 4430-4438.
[6] Chow PS, Lau G, Ng WK, et al.Stability of pharmaceutical cocrystal during milling: a case study of 1:1 caffeine-glutaric acid[J]. Crystal Growth & Design, 2017, 17(8): 4064-4071.
[7] Arafa MF, El-gizawy SA, Osman MA, et al. Co-crystallization for enhanced dissolution rate of nateglinide: in vitro and in vivo evaluation[J]. Journal of Drug Delivery Science and Technology, 2017, 38: 9-17.
[8] Chen Y, Li L, Yao J, et al.Improving the solubility and bioavailability of apixaban via apixaban-oxalic acid cocrystal[J]. Crystal Growth & Design, 2016, 16(5): 2923-2930.
[9] Suresh K, Minkov VS, Namila KK, et al.Novel synthons in sulfamethizole cocrystals: structure-property relations and solubility[J]. Crystal Growth & Design, 2015, 15(7): 3498-3510.
[10] Skorupska E, Jeziorna A, Potrzebowski MJ.Thermal solvent-free method of loading of pharmaceutical cocrystals into the pores of silica particles: a case of naproxen/picolinamide cocrystal[J]. The Journal of Physical Chemistry C, 2016, 120(24): 13169-13180.
[11] Peng B, Wang JR.Advances in characterization of pharmaceutical polymorphisms by vibrational spectroscopy[J]. Acta Pharmaceutica Sinica(药学学报), 2021, 56(1): 102-112.
[12] El-gizawy SA, Osman MA, Arafa MF, et al. Aerosil as a novel co-crystal co-former for improving the dissolution rate of hydrochlorothiazide[J]. International Journal of Pharmaceutics, 2015, 478(2): 773-778.
[13] Ishihara S, Hattori Y, Otsuka M.Mcr-als analysis of IR spectroscopy and XRD for the investigation of ibuprofen-nicotinamide cocrystal formation[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 221: 117142.
[14] Chi ZL, Wang MM, Cong XD, et al.Near infrared spectroscopy used in purification and determination of pharmaceutical cocrystal[J]. Chinese Journal of Analytical Chemistry(分析化学研究简报), 2013, 41(12): 1928-1931.
[15] Wu XM, Chi ZL, Cai BC.Near infrared spectroscopy used for content analysis of curcumin-lysine cocrystal[J]. Practical Pharmacy And Clinical Remedies(实用药物与临床), 2017, 20(4): 451-454.
[16] Silva MC. Ribeiro PR, Santos A, et al.A pat approach for the on-line monitoring of pharmaceutical co-crystals formation with near infrared spectroscopy[J]. International Journal of Pharmaceutics, 2014, 471(1-2): 478-484.
[17] Koide T, Takeuchi Y, Otaki T, et al.Quantification of a cocrystal and its dissociated compounds in solid dosage form using transmission Raman spectroscopy[J]. Journal of Pharmaceutical and Biomedical Analysis, 2020, 177: 112886
[18] Cai Q, Xue JD, Wang QQ, et al.Solid-state cocrystal formation between acyclovir and fumaric acid: Terahertz and Raman vibrational spectroscopic studies[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017, 186: 29-36.
[19] Zhang Q, Fang HX, Zhang HL, et al.Vibrational spectroscopic characterization of the co-crystal and the forming condition between γ-aminobutyric acid and benzoic acid[J]. Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2017, 37(12): 3786-3792.
[20] Fang HX.Polymorphs, cocrystal and quantitative analysis of sartans pharmaceutical compounds based on THz-TDS Technique[D]. Hangzhou: China Jiliang University, 2015.
[21] Ma Q, Wang YX, Zhang ZY, et al.Polymorphs, co-crystal between thymine and urea investigated with terahertz spectroscopy and density functional theory[J]. Journal of Lanzhou University: Natural Sciences(兰州大学学报:自然科学版), 2017, 53(6): 841-846.
[22] Du RK.Optimization of solid forms of ethinyl estradiol, vortioxetine and mifepristone to improve the physicochemical properties[D]. Guangzhou: South China University of Technology, 2020.
[23] Perpetuo GL, Chierice GO, Ferreira LT, et al.A combined approach using differential scanning calorimetry with polarized light thermomicroscopy in the investigation of ketoprofen and nicotinamide cocrystal[J]. Thermochimica Acta, 2017, 651: 1-10.
[24] Li DX.Progress of transmission electron microscopy Ⅰ development of transmission electron microscope and related equipments[J]. J Chin Electr Microsc Soc(电子显微学报), 2004, 23(3): 269-277.
[25] Ngilirabanga JB, Aucamp M, Rosa PP, et al.Mechanochemical synthesis and physicochemical characterization of isoniazid and pyrazinamide co-crystals with glutaric acid[J]. Frontiers in Chemistry, 2020, 8: 595908.
[26] Wang FF, Sun PC.Solid-state NMR characterization of polymers[J]. Acta Polymerica Sinica(高分子学报). 2021, 52(7): 840-856.
[27] Vogt FG, Clawson JS, Strohmeir M, et al.Solid-state NMR analysis of organic cocrystals and complexes[J]. Crystal Growth & Design, 2009, 9(2): 921-937.
[28] Shukla A, Khan E, Alsirawan MHD B, et al.Spectroscopic (FT-IR, FT-Raman, and 13C SS-NMR) and quantum chemical investigations to explore the structural insights of nitrofurantoin-4-hydroxybenzoic acid cocrystal[J]. New Journal of Chemistry, 2019, 43(18): 7136-7149.
[29] Alhalaweh A, George S, Basavoju S, et al.Pharmaceutical cocrystals of nitrofurantoin: screening, characterization and crystal structure analysis[J]. Cryst Eng Comm, 2012, 1(14): 5078-5088.
[30] Xu JC, Chen Y, Ye HQ, et al.Synthesis, characterization and physicochemical properties study of roxadustat co-crystals[J]. CIESC Journal(化工学报), 2020,71(4):1851-1858.
[31] Yang HX, Xiong J.Chemical reference substance graph set-dynamic vapor sorption(化学药品对照品图谱集—动态水分吸附)[M]. Beijing: China Medical Science Press, 2014:Ⅲ.
[32] Xiong J, Yang HX, Wu JM, et al.Chinese journal of pharmacy moisture sorption properties research of chemical reference substances based on dynamic vapor sorption analysis technology[J]. Chinese Journal of Pharmacy(中国药学杂志), 2015, 50(6): 532-535.
[33] Xiong J, Shi Y, Wu JM, et al.Using nonparametric test to analyze the relationship between hygroscopicity and water solubility of chemical drugs[J]. Chin Pharm J(中国药学杂志), 2016, 51(20): 1786-1789.
[34] Zhou Y, Wei NY, Xiong J, et al.Determination of hygroscopicity of Huperzine A[J]. Chemistry Education(化学教育), 2018, 39(2): 39-42.
[35] Zhang N, Huang HW, Xiong J, et al.Discussion on hygroscopicity of mecobalamin[J]. Chinese Pharmaceutical Affairs(中国药事), 2017, 31(10): 1181-1185.
[36] Xiong J, Ning BM, Wu JM, et al.Investigation on crystal structure and moisture sorption properties of riboflavin[J]. Chin Pharm J(中国药学杂志), 2015, 50(16): 1436-1440.
[37] Zhang N, Zhao Y, Yang SY, et al.Study on crystallographic form of crystalline materials of pravastatin sodium from different sources[J]. Chin J Pharm Anal(药物分析杂志), 2016, 36(12): 2139-2147.
[38] Xiong J, Xu DZ, Xu XY, et al.Establishment of a cocrystal characterization method for sacubitril valsartan sodium[J]. Acta Pharmaceutica Sinica(药学学报), 2021, 56(2): 577-584.