Effect of binary solvent mixtures on stability and morphology of thiamine hydrochloride solvate

doi:10.11949/j.issn.0438-1157.20170774

Abstract

Abstract:

Vitamin B₁ is one of the most essential nutrients in human bodies. Thiamine hydrochloride, a form of vitamin B₁, has four solvates, hemihydrate (HH), methanol solvates (MM), nonstoichiometric hydrate (NSH), and anhydrous form (AH). These four solvates have different stabilities because of different space structures. In that way, a stable solvate which has better properties of production, storage and transportation is investigated by drug industry. In this paper, X-ray diffraction and thermal analysis were measured and crystal form transformation experiments in methanol-water and methanol-ethyl acetate were investigated. It can be seen that hydrate hemihydrate is more stable because of hydrogen bonds. Moreover, molecular dynamics simulation by using BFDH and AE model of MM in methanol-ethyl acetate binary solvent mixtures was calculated. The result shows that BFDH model matches real crystal habit, which could guide industrial production.

Key words: thiamine hydrochloride, polymorphs, stability, solvent, transformation, molecular simulation

摘要：

维生素B₁是人体必需的营养物质之一，盐酸硫胺作为维生素B₁的存在形式，因其空间结构不同有着不同稳定性的4种溶剂化物：盐酸硫胺半水合物（HH）、盐酸硫胺甲醇溶剂化物（MM）、非化学计量比的盐酸硫胺水合物（NSH）、无水盐酸硫胺（AH）。制药行业致力于寻找一种相对稳定的盐酸硫胺，以便于生产、储存和运输。采用悬浮转晶的方法制备了4种盐酸硫胺溶剂化物，从分子层次探究4种溶剂化物的稳定性，得出盐酸硫胺半水合物因其内部强氢键作用力而最稳定的结论。同时，探讨了二元混合溶剂对盐酸硫胺4种溶剂化物稳定性的影响，确定了不同溶剂化物稳定存在的适宜条件。采用BFDH模型模拟了盐酸硫胺甲醇溶剂化物的晶习，发现BFDH模型的模拟结果与实际晶习一致，为工业溶剂筛选以获得目标产品提供理论指导。

关键词: 盐酸硫胺, 溶剂化物, 稳定性, 溶剂, 转化, 分子模拟

CLC Number:

TQ201.2

YANG Yang, WANG Haisheng, LIU Yumin, HAN Dandan, WANG Jingkang, GONG Junbo. Effect of binary solvent mixtures on stability and morphology of thiamine hydrochloride solvate[J]. CIESC Journal, 2018, 69(2): 570-577.

杨洋, 王海生, 刘玉敏, 韩丹丹, 王静康, 龚俊波. 二元混合溶剂对盐酸硫胺溶剂化物稳定性及晶习的影响[J]. 化工学报, 2018, 69(2): 570-577.

References 34

[1]	KHANKARI R K, GRANT D J W. Pharmaceutical hydrates[J]. Thermochimica Acta, 1995, 248(1):61-79.
[2]	CHAKRAVARTY P, SURYANARAYANAN R. Characterization and structure analysis of thiamine hydrochloride methanol solvate[J]. Crystal Growth & Design, 2010, 10(10):4414-4420.
[3]	GRIESSER U J. Chapter 8. The importance of solvate[M]//Polymorphism in the Pharmaceutical Industry, 2006:211-233.
[4]	CHAKRAVARTY P, BERENDT R T, MUNSON E J, et al. Insights into the dehydration behavior of thiamine hydrochloride (vitamin B1) hydrates[J]. Journal of Pharmaceutical Sciences, 2010, 99(2):816-827.
[5]	RUTH L T, ULRICH J G, KENNETH R M, et al. X-ray diffraction and solid-state nmr investigation of the single-crystal to single-crystal dehydration of thiamine hydrochloride monohydrate[J]. Crystal Growth & Design, 2003, 3(6):997-1004.
[6]	WATANABE A, NAKAMACHI H. Polymorphism of thiamine hydrochloride (author's transl)[J]. Yakugaku Zasshi Journal of the Pharmaceutical Society of Japan, 1976, 96(10):1236-1240.
[7]	RODRÍGUEZ-HORNEDO N, LECHUGA-BALLESTEROS D, WU H J. Phase transition and heterogeneous/epitaxial nucleation of hydrated and anhydrous theophylline crystals[J]. International Journal of Pharmaceutics, 1992, 85(1/2/3):149-162.
[8]	RANI M, GOVINDARAJAN R, SURANA R, et al. Structure in dehydrated trehalose dihydrate-evaluation of the concept of partial crystallinity[J]. Pharmaceutical Research, 2006, 23(10):2356-2367.
[9]	EYRING H. Chemistry of the Solid State[M]. Butterworths Scientific Publications, 1955.
[10]	BRENNER G, ROBERTS F E, HOINOWSKI A, et al. Effect of crystalline form on the air-oxidation of steroidal 11β-ols to 11-ones[J]. Angewandte Chemie International Edition, 1969, 8(12):975-976.
[11]	GIORDANO F. Polymorphism in pharmaceutical solids:edited by Harry G. Brittain, Marcel Dekker, New York, 1999, 427 pp[J]. Journal of Controlled Release, 2001, 71(3):354-355.
[12]	ZHU H J, YOUNG V G JR, GRANT D J. Crystal structure and thermal behavior of nedocromil nickel octahydrate[J]. International Journal of Pharmaceutics, 2002, 232(1/2):23-33.
[13]	ZHU H J, YOUNG V G JR, GRANT D J. Crystal structures and thermal analysis of nedocromil bivalent metal salt hydrates[J]. Journal of Chemical Crystallography, 2001, 31(9):421-434.
[14]	SHETH A R, ZHOU D, MULLER F X, et al. Dehydration kinetics of piroxicam monohydrate and relationship to lattice energy and structure[J]. Journal of Pharmaceutical Sciences, 2004, 93(12):3013-3026.
[15]	REUTZEL S M, RUSSELL V A. Origins of the unusual hygroscopicity observed in LY297802 tartrate[J]. Journal of Pharmaceutical Sciences, 1998, 87(12):1568-1571.
[16]	KLIMAKOW M, LEITERER J, KNEIPP J, et al. Combined synchrotron XRD/Raman measurements:in situ, identification of polymorphic transitions during crystallization processes[J]. Langmuir the ACS Journal of Surfaces & Colloids, 2010, 26(13):11233-11237.
[17]	SCHMIDT C, ULRICH J. Morphology prediction of crystals grown in the presence of impurities and solvents-an evaluation of the state of the art[J]. Journal of Crystal Growth, 2012, 353(1):168-173.
[18]	SCHMIDT C, YÜRÜDÜ C, WACHSMUTH A, et al. Modeling the morphology of benzoic acid crystals grown from aqueous solution[J]. Crystengcomm, 2011, 13(4):1159-1169.
[19]	LAHAV M, LEISEROWITZ L. The effect of solvent on crystal growth and morphology[J]. Chemical Engineering Science, 2001, 56(7):2245-2253.
[20]	NIEHÖRSTER S, ULRICH J. Designing crystal morphology by a simple approach[J]. Crystal Research & Technology, 2010, 30(3):389-395.
[21]	MATTOS M, NIEHOERSTER S, WANGNICK K, et al. Comparison between theoretical and experimental results of habit modification of crystalline stabilizers for foods[J]. Journal of Mechanical Engineering, 2011, 41(2):4169-4177.
[22]	LIU N, LI Y N, ZEMAN S, et al. Crystal morphology of 3,4-bis(3-nitrofurazan-4-yl)furoxan (DNTF) in a solvent system:molecular dynamics simulation and sensitivity study[J]. Crystengcomm, 2016, 18(16):2843-2851.
[23]	ZHANG C, PENG Q, WANG L, et al. Thermal sensitivity of HMX crystals and HMX-based explosives treated under various conditions[J]. Propellants Explosives Pyrotechnics, 2010, 35(6):561-566.
[24]	MANNER V W, TAPPAN B C, SCOTT B L, et al. Crystal structure, packing analysis, and structural-sensitivity correlations of erythritol tetranitrate[J]. Crystal Growth & Design, 2014, 14(11):6154-6160.
[25]	CZERSKI H, PROUD W G. Relationship between the morphology of granular cyclotrimethylene-trinitramine and its shock sensitivity[J]. Journal of Applied Physics, 2007, 102(11):837-840.
[26]	ZHOU Q, CHEN Z Q, ZHENG C M, et al. Effect of morphology of FOX-7 crystals on its sensitivity[J]. Chinese Journal of Explosives & Propellants, 2014, 37(5):67-69, 76.
[27]	HOD I, MASTAI Y, MEDINA D D. Effect of solvents on the growth morphology of DL-alanine crystals[J]. Crystengcomm, 2010, 13(2):502-509.
[28]	SINGH M K, BANERJEE A, GUPTA P K. Role of molecular orientation and surface relaxation on vapor growth shape of molecular crystals[J]. Crystal Growth & Design, 2012, 12(2):732-741.
[29]	URBELIS J H, SWIFT J A. Solvent effects on the growth morphology and phase purity of CL-20[J]. Crystal Growth & Design, 2014, 14(4):1642-1649.
[30]	DUAN X, WEI C, LIU Y, et al. A molecular dynamics simulation of solvent effects on the crystal morphology of HMX[J]. Journal of Hazardous Materials, 2010, 174(1/2/3):175-180.
[31]	MIROSHNYK I, KHRIACHTCHEV L, MIRZA S, et al. Insight into thermally induced phase transformations of erythromycin A dihydrate[J]. Crystal Growth & Design, 2006, 6(2):369-374.
[32]	LESTER C, LUBEY G, DICKS M G, et al. Dehydration of risedronate hemi-pentahydrate:analytical and physical characterization[J]. Journal of Pharmaceutical Sciences, 2006, 95(12):2631-2644.
[33]	CHEN L R, YOUNG V G J, LECHUGA-BALLESTEROS D, et al. Solid-state behavior of cromolyn sodium hydrates[J]. Journal of Pharmaceutical Sciences, 1999, 88(11):1191-1200.
[34]	WATANABE A, TASAKI S, WADA Y, et al. Polymorphism of thiamine hydrochloride(Ⅱ):Crystal structure of thiamine hydrochloride hemihydrate and its stability[J]. Chemical & Pharmaceutical Bulletin, 1979, 27(11):2751-2759.