博碩士論文 943204016 詳細資訊




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姓名 張瓊文(Chyong Wen)  查詢紙本館藏   畢業系所 化學工程與材料工程學系
論文名稱 外消旋(R,S)-(±)-伊普鹽二水化合物的介晶質,成核與結晶成長
(Mesocrystals, Nucleation and Crystal Growth of Racemic (R,S)-(±)-Sodium Ibuprofen Dihydrate)
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摘要(中) 在藥物的市場上,大約50%的藥物都是消旋性混合物 (racemic mixture)。消旋性混合物的種類有三種: 外消旋聚集物、外消旋混合物或者擬消旋體(固體溶液)。市面上大部分(90-95%)的外消旋藥都是外消旋混合物。在這篇論文中,我們集中在伊普鹽二水化合物的外消旋混合物藥的結晶。在本研究中有三個部份。首先,利用初步的溶劑篩選建立一個有關伊普鹽二水化合物的外消旋混合物結晶的資料庫,有溶解度、同質異相、結晶度和晶貌。Hansen parameters被利用來預測活性藥物份在不同的溶劑中的溶解度。第二,添加硫酸十二酯鈉在伊普鹽二水化合物的外消旋混合物的結晶中可以誘發介晶質的聚集並且具有良好的排列方向和外在的晶面。奈米顆粒可以自我組裝成介晶質而增加伊普鹽二水化合物的外消旋混合物的溶解速率。並且,添加硫酸十二酯鈉添加物可以誘發不同的同質異相並改變左右旋的比例。第三,我們使用電導度計來執行原位監控整個介晶質結晶過程並且整合熱力學與動力學的資訊來建立基本的成核和成長的參數。最後,所有的實驗都進行在伊普鹽二水化合物的外消旋混合物的臨界微胞濃度之上。
摘要(英) In the pharmaceutical market, approximately 50% are racemics (mixture of enantiomers). Racemic species have three types: racemic conglomerate, racemic compound and pseudoracemate. Most of the racemic drugs are racemic compound (90-95%). In this thesis, we focused on the crystallization of the racemic compound of (R,S)-(±)-sodium ibuprofen dihydrate. It has three sections in this study. Firstly, a useful engineering data bank of solubility, polymorph, crystallinity and crystal habits of racemic (R,S)-(±)-sodium ibuprofen dihydrate was established by initial solvent screening. Hansen parameters were utilized to predict APIs’ solubility in different solvents. Secondly, the presence of sodium dodecyl sulfate (SDS) additive in the crystallization of racemic (R,S)-(±)-sodium ibuprofen dihydrate could induce the formation of aggregation of mesocrystals which has well-aligned orientation and external crystal faces. Nanoparticles by self-assembly to form mesocrystals can enhance dissolution rate of racemic (R,S)-(±)-sodium ibuprofen dihydrate. Beside, the presence of the additive can induce different polymorphs and chance chiral resolution. Thirdly, conductivity in situ to monitor the entire crystallization process of mesocrystals and to gather the mesocrystals kinetic (nucleation and crystal growth) and thermodynamic (Gibbs free energy) information. The fundamental nucleation and crystal growth parameters were then estimated. Finally, all of the experiments were preceded above Critical Micelle Concentration (CMC) of racemic (R,S)-(±)-sodium ibuprofen dihydrate.
關鍵字(中) ★ 硫酸十二酯鈉
★ 伊普鹽二水化合物
關鍵字(英) ★ mesocrystals
★ S)-(±)-Sodium Ibuprofen Dihydrate
★ solvent screening
★ Racemic (R
★ nucleation and crystal growth
論文目次 摘要………………………………………………………………………………………I
Abstract………………………………………………………………………………… II
Acknowledgments…………………………………………………………...………... IV
Table of Contents………………………………………………………………………..V
List of Tables…………………………………………………………………………...IX
List of Figures………………………………………………………………………….XI
Chapter 1 Executive summary…………………………………………………………..1
1.1 Introduction………………………………………………………………….…1
1.2 Brief Induction of Racemic Compound of Drug……………………………….5
1.3 Conceptual Framework………………………………………………………...9
References………………………………………………………………………...13
Chapter 2 Instrumental Analysis………………………………………………………17
2.1 Introduction…………………………………………………………………...17
2.2 Thermal Analysis……………………………………………………………...21
2.2.1 Differential Scanning Calorimetry (DSC)……………………………21
2.2.2 Thermogravimetric analysis (TGA)………………………………….25
2.3 Spectrometry analysis ………………………………………………………..28
2.3.1 Powder X-ray Diffraction (PXRD)…………………………………..28
2.3.2 Fourier Transform Infrared (FTIR) Spectroscopy………….…………32
2.4 Microscopic methods ...………………………………………………………34
2.4.1 Optical Microscope (OM)…………………………………………...34
2.4.2 Scanning Electron Microscope (SEM)………………………………38
2.5 Electrical Conductance……………..………………………………...……….44
2.6 Conclusions…………………………………………………………...………47
References……………………………………...…………………………………48
Chapter 3 Solubility, Polymorphism, Crystallinity and Crystal Habits of Racemic
(R,S)-(±)-Sodium Ibuprofen Dihydrate by Initial Solvent Screening…...…..54
3.1 Introduction…………………………...………………………………………54
3.2 Experiment methods…………………….…………………………………….61
3.2.1 Materials……………………………………………………………..61
3.2.2 Solvent screening of racemic compound of R/S (±) sodium ibuprofen dihydrate…………………………………………………...………...66
3.2.3 Measurement Instrument……………………………….……………67
3.2.3.1 Differential scanning calorimetry (DSC)………………………67
3.2.3.2 Thermogravimetric analysis (TGA)…………………………....68
3.2.3.3 Powder X-ray diffraction (PXRD)……………………………..68
3.2.3.4 Fourier transform infrared spectroscopy (FT-IR)…………..….69
3.2.3.5 Optical Microscopy (OM)………………...……………………69
3.2.3.6 Low Vacuum Scanning Electron Microscopy (LV-SEM)……...70
3.3 Results and Discussion………………………….……………………………71
3.3.1 Solubility……………………………………………………..……...71
3.3.2 Polymorph………………….………………………………………..79
3.3.3 Crystallinity……………...…………………………………………..83
3.3.4 Crystal Habits………………………………………………………..85
3.3.5 Hansen parameter for racemic (R,S)-(±)-sodium ibuprofen dihydrate……………………………………………………………..90
3.4 Conclusions…………………………...………………………………………95
References………………………………………………………………………...97
Chapter 4 Mesocrystals Formation in the Presence of Sodium Dodecyl Sulfate (SDS)
Additive in supersaturated Racemic (R,S)-(±)-Sodium Ibuprofen Dihydrate
Aqueous Solution………………………………………………………..104
4.1 Introduction………………………………………………………………….104
4.2 Materials………………...…………………………………………………...109
4.2.1 Racemic (R,S)-(±)-sodium ibuprofen dihydrate……...…………….109
4.2.2 Sodium dodecyl sulfate (SDS)……………………….…………….110
4.2.3 Organic solvent……………………………………………………..110
4.3 Experimental Procedures…………………...………………………………..111
4.4 Instrumental Analysis………………………………………………………..113
4.4.1 Differential scanning calorimetry (DSC)…………………………..113
4.4.2 Powder X-ray diffraction (PXRD)…………………………………113
4.4.3 Low Vacuum Scanning Electron Microscopy (LV-SEM)………….114
4.4.4 Electrical Conductance………………………………………….….114
4.4.5 Dissolution test………………………………………………….….115
4.5 Results and Discussion………………………………………………………117
4.5.1 Differential scanning calorimetry (DSC) analysis………..………..117
4.5.2 SEM Photographs of Mesocrystals………………..……………….122
4.5.3 Prove of Mesocrystals…………...…………………………………126
4.5.3.1 SEM shown aggregate……………………..……………..…...126
4.5.3.2 PXRD analysis…………………………………………..……126
4.5.4 Solubility and dissolution rate……..……………………………….130
4.6 Conclusions………………………………………………………………….133
References……………………………………………………………………….134
Chapter 5 Effects of Sodium Dodecyl Sulfate (SDS) on Crystallization Kinetics of
Racemic (R,S)-(±)-Sodium Ibuprofen Dihydrate in Aqueous solution…...141
5.1 Introduction………………………………………………………………….141
5.2 Materials………………...…………………………………………………...144
5.2.1 Racemic (R,S)-(±)-sodium ibuprofen dihydrate……...…………….144
5.2.2 Sodium dodecyl sulfate (SDS)……………………….…………….145
5.2.3 Organic solvent…………………………………………………….145
5.3 Experimental Procedures…………………...………………………………..146
5.4 Instrumental Analysis………………………………………………………..148
5.4.1 Electrical Conductance………………………………….………….148
5.5 Results and Discussion………………………………………………………149
5.5.1 Nucleation Mechanism……………………………………….…….149
5.5.2 Crystal Growth Mechanism………………………………………..156
5.5.3 Critical Micelle Concentration (CMC)………………….…………165
5.6 Conclusions………………………………………………………………….168
Notation………………………………………………………………………….169
References…………………………………………………………….…………170
Chapter 6 Conclusions and Future Works…………………………………………….176
6.1 Initial Solvent Screening………………………………………...…………..176
6.2 Mesocrystals Formation in the Presence of Sodium Dodecyl Sulfate (SDS)
Additive in Supersaturated Racemic (R,S)-(±)-Sodium Ibuprofen Dihydrate
Aqueous Solution…………………………………………………...……….177
6.3 Effects of Sodium Dodecyl Sulfate (SDS) on Crystallization Kinetics of
Racemic (R,S)-(±)-Sodium Ibuprofen Dihydrate in Aqueous Solution……178
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指導教授 李度(Tu Lee) 審核日期 2007-7-19
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