Computational pharmaceutical solid state chemistry. (2016)

• Record Type: Book
• Further Information: Note: Edited by Yuriy A. Abramov.
• Editors: Abramov, Yuriy A
• Contents: List of Contributors xiii Preface xvii Editor’s biography xix 1 Computational Pharmaceutical Solid‐State Chemistry: An Introduction 1; Yuriy A. Abramov 1.1 Introduction 1 1.2 Pharmaceutical Solid‐State Landscape 2 1.2.1 Some Definitions 2 1.2.2 Impact of Solid‐State Form on API and Product Properties 4 1.2.3 Challenges of Pharmaceutical Industry Related to Solid Form Selection 6 1.3 Pharmaceutical Computational Solid‐State Chemistry 8 1.4 Conclusions 9 Acknowledgment 10 References 10 2 Navigating the Solid Form Landscape with Structural Informatics 15; Peter T. A. Galek, Elna Pidcock, Peter A. Wood, Neil Feeder, and Frank H. Allen 2.1 Introduction 15 2.2 The Csd System 17 2.3 Hydrogen‐Bond Propensity: Theory and Applications to Polymorphism 18 2.3.1 Methodology 18 2.3.2 Case Study 1: Ritonavir 19 2.4 Hydrogen‐Bond Landscapes: Developing the Propensity Approach 21 2.4.1 Methodology 21 2.4.2 Case Study 2: Metastable versus Stable Form of Piroxicam 22 2.4.3 Case Study 3: Exploring the Likely Hydrogen‐Bond Landscape of Axitinib (Inlyta®) 25 2.5 Informatics‐Based Cocrystal Screening 25 2.5.1 Methodology 25 2.5.2 Case Study 4: Paracetamol 26 2.5.3 Case Study 5: AMG 517 – Sorbic Acid Cocrystal 29 2.6 Conclusions and Outlook 32 References 33 3 Theoretical Hydrogen‐Bonding Analysis for Assessment of Physical Stability of Pharmaceutical Solid Forms 37; Yuriy A. Abramov 3.1 Introduction 37 3.2 Experimental Scales of H‐Bonding Basicity and Acidity 39 3.2.1 In Solution Phase 39 3.2.2 In Solid‐State Phase 40 3.3 Theoretical Study of H‐Bonding Strength in Solution and in Solid State 40 3.3.1 Supermolecular Approach 41 3.3.2 Descriptor‐Based Approaches 41 3.3.3 Solid‐State H‐bonding Strength 42 3.4 Application to Solid Form Selection 47 3.4.1 Examples of Theoretical H‐Bonding Analysis to Support Solid Form Selection 48 3.4.2 Consideration of Limitations of Hydrogen‐Bonding Propensity Approach 50 3.5 Conclusion 52 Acknowledgment 53 References 53 4 Improving Force Field Parameters for Small‐Molecule Conformation Generation 57; Dmitry Lupyan, Yuriy A. Abramov, and Woody Sherman 4.1 Introduction 57 4.2 Methods 62 4.3 Results and Discussion 66 4.3.1 Close S⋯O Interactions 66 4.3.2 Halogen X⋯O Interactions 75 4.3.3 Generalization of the Approach to Other Interactions 77 4.3.4 An Improved OPLS Force Field (OPLS2) 80 4.4 Conclusion 81 References 82 5 Advances in Crystal Structure Prediction and Applications to Pharmaceutical Materials 87; Graeme M. Day 5.1 Introduction 87 5.1.1 Motivation 88 5.2 Crystal Structure Prediction Methodologies 89 5.2.1 Molecular Geometry 89 5.2.2 Crystal Structure Searching 99 5.2.3 Structure Ranking 102 5.3 Applications of Crystal Structure Prediction 105 5.3.1 Crystal Structure Determination 106 5.3.2 Solid Form Screening 108 5.4 Summary 110 References 110 6 Integrating Computational Materials Science Tools in Form and Formulation Design 117; Joseph F. Krzyzaniak, Paul A. Meenan, Cheryl L. Doherty, Klimentina Pencheva, Suman Luthra, and Aurora Cruz‐Cabeza 6.1 Introduction 117 6.2 From Molecule to Crystal Structure 119 6.2.1 Single Crystal Structure 120 6.2.2 Structural Analysis 120 6.2.3 Molecular Packing and HB Geometry Analyses 122 6.2.4 Full Interaction Maps 123 6.2.5 Crystal Structure Prediction 124 6.3 From Crystals to Particles 131 6.4 From Particles to Dosage Forms 134 6.4.1 Structural Investigation of Crystal Surfaces and Structure Dehydration 137 6.4.2 Structural Investigations of Crystal Surfaces and Chemical Stability 139 6.5 Conclusion 141 Acknowledgments 142 References 142 7 Current Computational Approaches at Astrazeneca for Solid‐State and Property Predictions 145; Sten O. Nilsson Lill, Staffan Schantz, Viktor Broo, and Anders Broo 7.1 Introduction 145 7.2 Polymorphism 146 7.3 Conformer Search 157 7.4 Molecular Perturbations to Achieve Solubility for Gpr119 Ligands 158 7.5 Solid‐State Nuclear Magnetic Resonance and Azd8329 Case Study 163 7.6 Ccdc Tools 168 7.7 Tautomerism 169 7.8 Conclusions 170 Acknowledgments 170 References 170 8 Synthonic Engineering: From Molecular and Crystallographic Structure to the Rational Design of Pharmaceutical Solid Dosage Forms 175; Kevin J. Roberts, Robert B. Hammond, Vasuki Ramachandran, and Robert Docherty 8.1 Introduction 175 8.2 The Crystal 177 8.2.1 Crystallography 177 8.2.2 Crystal Chemistry and Crystal Packing of Drug Molecules 179 8.2.3 Deconstructing the Supra‐Molecular Interactions in Bulk – Intrinsic Synthons 181 8.3 Morphology and Surface Structure 185 8.3.1 Nucleation and the Crystal Growth Process 185 8.3.2 Particle Morphology and Surface Structure 186 8.3.3 Crystal Morphology Prediction 188 8.3.4 Deconstructing the Supra‐Molecular Interactions at Surfaces – Extrinsic Synthons 190 8.3.5 Grid Searching – Probing Inter‐molecular Interactions at Surfaces and Environments 190 8.4 The Crystallisation Perspective 191 8.4.1 Nucleation, Surface Energies and Directed Polymorphism 191 8.4.2 The Impact of Solvent on Morphology 194 8.4.3 The Impact of Impurities on Morphology 196 8.5 The Drug Product Perspective 197 8.5.1 Excipient Compatibility 197 8.5.2 Inhaled Drug Delivery Design 199 8.5.3 Mechanical Properties 201 8.5.4 Dissolution 203 8.6 Summary and Future Outlook: Synthonic Engineering Particle Passport and the Future of the Drug Product Design 205 Acknowledgements 207 References 207 9 New Developments in Prediction of Solid‐State Solubility and Cocrystallization Using Cosmo‐Rs Theory 211; Christoph Loschen and Andreas Klamt 9.1 Introduction 211 9.2 Cosmo‐Rs 212 9.3 Prediction of Drug Solubility Using Cosmo‐Rs 215 9.4 Solubility Prediction with Multiple Reference Solvents 218 9.5 Melting Point and Fusion Enthalpy Qspr Models 221 9.6 Cocrystal Screening 225 9.7 Solvate Formation 229 9.8 Summary 231 References 231 10 Modeling and Prediction of Solid Solubility by Ge Models 235; Larissa P. Cunico, Anjan K. Tula, Roberta Ceriani, and Rafiqul Gani 10.1 Introduction 235 10.2 Framework 236 10.2.1 Thermodynamic Basis 238 10.2.2 The Necessary Property‐Related Information for Solid Solubility Prediction and the Developed Databases 238 10.2.3 SLE Thermodynamic Consistency Tests 241 10.2.4 SolventPro 252 10.3 Conclusion 259 References 260 11 Molecular Simulation Methods to Compute Intrinsic Aqueous Solubility of Crystalline Drug‐Like Molecules 263; David S. Palmer and Maxim V. Fedorov 11.1 Introduction 263 11.2 Definitions of Solubility 264 11.3 Solubility and Thermodynamics 264 11.3.1 Solubility and Free Energy of Solution 264 11.3.2 Computation of Solubility from the Thermodynamic Cycle of Solid to Supercooled Liquid to Aqueous Solution 265 11.3.3 Computation of Solubility from the Thermodynamic Cycle of Solid to Gas Ph
• Edition: 1st
• Publisher Details: Hoboken, New Jersey : John Wiley & Sons, Inc
• Publication Date: 2016
• Extent: 1 online resource
• Subjects: 615.19; Pharmaceutical chemistry; Solid state chemistry
• Languages: English
• ISBNs: 9781119229179; 9781119229193
• Related ISBNs: 9781118700747
• Notes: Note: Description based on CIP data; item not viewed.
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