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1 We will begin momentarily at 2pm ET Slides available now! Recordings will be available to ACS members after one week. Contact ACS Webinars at 1 Have Questions? Why am I muted? Don t worry. Everyone is muted except the presenter and host. Thank you and enjoy the show. Type them into questions box! Contact ACS Webinars at acswebinars@acs.org 2 1
2 Have you discovered the missing element? Find the many benefits of ACS membership! 3 Benefits of ACS Membership Chemical & Engineering News (C&EN) The preeminent weekly news source. NEW! Free Access to ACS Presentations on Demand ACS Member only access to over 1,000 presentation recordings from recent ACS meetings and select events. NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more
3 Let s get Social post, tweet, and link to ACS Webinars during today s broadcast! Search for acswebinars and connect! 5 How has ACS Webinars benefited you? As a pharmacologist, ACS Webinars have provided me with a better understanding of the chemistry aspects of my projects and enabled me to interact effectively with my chemist collaborators. Abir El-Alfy, Ph.D. Associate Professor, Pharmaceutical Sciences College of Pharmacy, Chicago State University Be a featured fan on an upcoming webinar! Write to acswebinars@acs.org 6 3
4 youtube.com/acswebinars Search for acswebinars and connect! 7 Learn from the best and brightest minds in chemistry! Hundreds of webinars presented by subject matter experts in the chemical enterprise. Recordings are available to current ACS members one week after the Live broadcast date. Broadcasts of ACS Webinars continue to be available to the general public LIVE every Thursday at 2pm ET! 8 4
5 Upcoming ACS Webinars Thursday, September 10, 2015 How to Create a Safer and More Sustainable Lab Through Green Chemistry Jeffrey Whitford, Director of Global Citizenship, Sigma-Aldrich David C. Finster, Professor of Chemistry, Wittenberg University Thursday, September 17, 2015 Paving Your Eligibility Pathway: Green Card Tips for Scientists, Professors and Researchers Peter F. Asaad, Managing Partner, Immigration Solutions Group, PLLC Meredith Jolie, Attorney, Immigration Solutions Group, PLLC Contact ACS Webinars at acswebinars@acs.org 9 Lecture 1: Preformulation and Biopharmaceutical Considerations in Drug Product Design and Development Lecture 2: Drug Substance Physical Form Selection Lecture 3: Drug Substance Physical Form Characterization Lecture 4: Solubility: General Principles and Practical Considerations Lecture 6: Biopharmaceutic Considerations Lecture 7: Chemical Stability Assessment in Preformulation Lecture 8: Excipient Compatibility Studies Lecture 9: Impact of Material Properties on Formulation Development Lecture 5: Dissolution and its Role in Solid Oral Dosage Form Development Lecture 10: Prototype Formulations Screening and Characterization NEW ecourse Available NOW! Visit for more information. 5
6 Join the ACS Division of Medicinal Chemistry Today! For $25 ($10 for students), You Will Receive: A free copy of our annual medicinal chemistry review volume (over 600 pages, $160 retail price) Abstracts of MEDI programming at national meetings Access to student travel grants and fellowships Find out more about the ACS MEDI Division!
7 Join us September 24, 2015 for the 9 th Session! Drug Design and Delivery Symposium: Choices and Trends in Solid Dosage Form Selection Rao Mantri Bristol-Myers Squibb Scott Trzaska J-Star Research Ronald Smith Merck Slides available now! Recordings will be available to ACS members after one week The 2015 Drug Design and Delivery Symposium is co-produced by the ACS Medicinal Chemistry Division and the AAPS 14 7
8 Choices and Trends in Solid Dosage Form Selection: Salt, Cocrystal, Prodrug or Amorphous? Scott Trzaska, J-Star Research Ron Smith, Merck August 27, 2015 Pharmaceutical Materials Particle Attributes O OH API O Solid State Form O Drug Product Formulated Intermediate 16 8
9 Form, Attributes, and Formulation Solid State Form Stability Robust Crystallization Solubility Formulation Enteric Coating Dispersions Solutions Particle Attributes Filtration rates Content Uniformity Dissolution rate Manufacturability Bioperformance 17 Solid State Forms Polymorphs Hydrates and solvates Salts + Cocrystals Amorphous
10 Prodrug Prodrugs in Drug Discovery Thursday, November 19, 2015 John Higgins, Senior Principal Scientist, Discovery Pharmaceutical Sciences at Merck 19 The Ideal Solid State Form Good biological performance Suitable solid-state properties Acceptable chemical and physical stability Manufacturing ease Minimal risk 20 10
11 Considerations Phase of the program Indication Dose Formulation Long term strategy 21 Solid State Form Selection Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 22 11
12 Solid State Form Selection Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 23 Screening Tools Melt Crystallizations Vapor Diffusion Automated Crystallizations Isothermal Crystallizations Variable Temperature Solvent Drop Grinding Sonication Induced Nucleation Controlled Heating and Cooling 24 12
13 Screening Techniques Solution temperature cycling Evaporative crystallizations Solvent vapor diffusion into solids Laser induced crystallization Sublimation Slurry conversions Solid state temperature cycling Antisolvent addition to solutions Mechanical activation ph swings Newman, A. Organic Process Research and Development 2013, 17 (3), , Specialized Solid Form Screening Techniques Lee, E. H. Asian Journal of Pharmaceutical Sciences 2014, 9 (4), , A Practical Guide to Pharmaceutical Polymorph Screening & Selection 25 Solid State Form Selection Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 26 13
14 Thermodynamic Relationships Temperature, pressure, and water activity Polymorphs o Most stable o Transition temperatures Solvates and hydrates o Temperatures o Activities Salts Cocrystals Amorphous systems 27 Thermodynamics: Polymorphs Monotropic Enantiotropic Transition temperature Techniques osolubility oslurry transformations ocalorimetry Miller, M. J.; Collman, B. M.; Greene, L. R.; Grant, D. J. W.; Blackburn, A. C. Pharmaceutical Development and Technology 2005, 10, , Identifying the Stable Polymorph Early in the Drug Discovery Development Process Yu, L. Journal of Pharmaceutical Sciences 1995, 84, , Inferring Thermodynamic Stability Relationship of Polymorphs from Melting Data 28 14
15 Most Stable Form: Solubility Form 3 Solubility Form 1 Form 2 DG Form 1 Form 2 = RT ln (X 2 /X 1 ) DG Form 2 Form 3 = RT ln (X 3 /X 2 ) T T transition Form 2 is always more stable than Form 1, monotropic Form 3 is more stable than Form 2 below T transition, enantiotropic 29 Most Stable Form: Slurries Diverse solvent systems o Functional groups, polarity, hydrogen bonding, activity Vary temperature Days to weeks Form 1 [10 mg/ml] Solution Form 1 Form 2 [5 mg/ml] Form 1 Form Solvate Form 2 Form 2 Gu, C.; Li, H.; Gandhi, R. B.; Raghavan, K. International Journal of Pharmaceutics 2004, 283, , Grouping Solvents by Statistical Analysis of Solvent Property Parameters: Implications to Polymorph Screening 30 15
16 Thermodynamics: Hydrates Understand relationship of anhydrous form and hydrate Temperature Pressure Water activity 31 Anhydrous Versus Hydrate Chemical potential impacts relative stability m w = m w + RT ln a w a w = g w X w m w = m w + RT ln (g w X w ) Hydrate favored at high m w T a w (X w ) Anhydrous form favored at low m w T a w (X w ) Anhydrous form is stable above critical T and below critical a w
17 Literature Example: Amgen Originally isolating an anhydrous form A hemihydrate was discovered during development Anhydrous a w > 0.452, 25 C a w < 0.452, 25 C Hemihydrate Morrison, H.; Quan, B. P.; Walker, S. D.; Hansen, K. B.; Nagapudi, K.; Cui, S. Organic Process Research and Development ASAP Article, DOI: /acs.oprd.5b00030, Appearance of a New Hydrated Form during Development: A Case Study in Process and Solid-State Optimization 33 Thermodynamics: Salts Disproportionation ph max Excipients 34 17
18 Solubility (mg/ml) BH + Cl - = High Solubility 8/27/2015 Solid-Solution Equilibria B = Weak Base BH + + Cl - S salt K a B + H + + Cl - S 0 B = Low Solubility BH + Cl - (s) B (s) ph max pk a S log S 0 salt ph ph max Serajuddin, A. T. M. Advanced Drug Delivery Reviews 2007, 59, , Salt Formation to Improve Drug Solubility 35 Thermodynamics: Cocrystals Ternary Phase diagram Solvent API Cocrystal Cocrystal Former 36 18
19 Thermodynamics: Cocrystals Ternary Phase diagram Solvent API Cocrystal Cocrystal Former 37 Thermodynamics: Amorphous Dispersion phase separation Crystallization risk Humidity Meng, F.; Dave, V.; Chauhan, H. European Journal of Pharmaceutical Sciences 2015, 77, , Qualitative and Quantitative Methods to Determine Miscibility in Amorphous Drug-Polymer Systems 38 19
20 Solid State Form Selection Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 39 Properties Biological Performance Solubility Dissolution Rate Particle Attributes Excipients Physical Stability Thermodynamic stability Risk of a form change Processing space Chemical Stability Oxidation Hydrolysis Photochemical Thermal decomposition Mechanical Stability Physical impact Pressure Disorder 40 20
21 Solid State Form Selection Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 41 Scale Up Thermodynamic or kinetic control? Can the form be manufactured? o Crystallization o Filtration o Solvent removal o Particle attribute control Can the form be formulated? 42 21
22 Solid State Form Selection Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 43 Salts of Weak Acids and Bases: In Vivo Behavior ph Salts of acid Can precipitate in the stomach in an uncontrolled fashion May parachute in solution (supersaturation) Free acid solubility increases with transit Salts of base Stomach conditions favor the acid addition salts of bases Rate and extent of absorption depends on: o Dissolution in stomach o Precipitation vs absorption kinetics o Absorption window (site of absorption) 44 22
23 Case Example: Ifetroban Sodium O - Na + O O O N N O O O O N O - Na + N O Weak acid (pka = 4.5) Solubility of sodium salt > 700 mg/ml Solubility of free acid = mg/ml Conversion of Na salt to free acid in dosage form (micro-environmental ph) High solubility ration (salt to free form) not always desired Serajuddin et. al., J. Pharm. Sci., 88(7), , Case Example: Atazanavir Sulfate Solubility (mg/ml) 4 3 Salt FreBase phadjustedwithhcl phadjustedwithh2so ph Weak base (pka = 4.7) Solubility <0.001 mg/ml (above ph 4.2) Bisulfate salt dissolves to a higher extent than its equilibrium value The higher initial solubility, though temporary, helps in its dissolution- absorption behavior Free base gave ~0% oral bioavailability; Bisulfate salt exhibited ~ 20% absolute oral bioavailability in dogs Bisulfate salt selected as final form US Patent: 6,087,
24 Role of Form, Formulation and Dose on Oral Fraction Absorbed Key Parameters Dose & Solubility Permeability Particle Size Dose Number Absorption Number Dissolution Number Oh et al, Pharm. Res., 10, , Phase Selection Attributes: When does particle size influence oral absorption? Biopharmaceutics Classification Scheme Dissolution-limited absorption Dissolution rate slower than permeability Reduction in particle size translates to improved oral bioavailability Permeability-limited absorption Permeability slower than dissolution rate No effect of particle size reduction (micronization) on oral bioavailability Solubility-limited absorption When dose is very high relative to solubility No effect of particle size reduction (micronization) on oral bioavailability Many drugs are dissolution-limited at low doses and solubility-limited at high doses 48 24
25 Increasing Oral Exposure: Particle size reduction or amorphous? Fakes et al, Int. J. Pharm., 370: , Summary Screen for crystalline candidates Identify thermodynamic relationships Biological, physical, chemical, and mechanical properties Scale up Selection 50 25
26 Form, Attributes, and Formulation Solid State Form Stability Robust Crystallization Solubility Formulation Enteric Coating Dispersions Solutions Particle Attributes Filtration rates Content Uniformity Dissolution rate Manufacturability Bioperformance Drug Design and Delivery Symposium: Choices and Trends in Solid Dosage Form Selection Rao Mantri Bristol-Myers Squibb Scott Trzaska J-Star Research Ronald Smith Merck Slides available now! Recordings will be available to ACS members after one week The 2015 Drug Design and Delivery Symposium is co-produced by the ACS Medicinal Chemistry Division and the AAPS 52 26
27 Join us September 24, 2015 for the 9 th Session! 53 Upcoming ACS Webinars Thursday, September 10, 2015 How to Create a Safer and More Sustainable Lab Through Green Chemistry Jeffrey Whitford, Director of Global Citizenship, Sigma-Aldrich David C. Finster, Professor of Chemistry, Wittenberg University Thursday, September 17, 2015 Paving Your Eligibility Pathway: Green Card Tips for Scientists, Professors and Researchers Peter F. Asaad, Managing Partner, Immigration Solutions Group, PLLC Meredith Jolie, Attorney, Immigration Solutions Group, PLLC Contact ACS Webinars at acswebinars@acs.org 54 27
28 2015 Drug Design and Delivery Symposium: Choices and Trends in Solid Dosage Form Selection Rao Mantri Bristol-Myers Squibb Scott Trzaska J-Star Research Ronald Smith Merck Slides available now! Recordings will be available to ACS members after one week The 2015 Drug Design and Delivery Symposium is co-produced by the ACS Medicinal Chemistry Division and the AAPS 55 Featured Topics: Neuroinflammation Cancer Immunotherapy Heart Failure Natural Products Protein-Protein Interactions Drug Safety Deuterated Drugs Covalent Inhibitors Ophthalmic Drugs Allosteric Inhibitors Inducible Pockets First Time Disclosures 28
29 Lecture 1: Preformulation and Biopharmaceutical Considerations in Drug Product Design and Development Lecture 2: Drug Substance Physical Form Selection Lecture 3: Drug Substance Physical Form Characterization Lecture 4: Solubility: General Principles and Practical Considerations Lecture 6: Biopharmaceutic Considerations Lecture 7: Chemical Stability Assessment in Preformulation Lecture 8: Excipient Compatibility Studies Lecture 9: Impact of Material Properties on Formulation Development Lecture 5: Dissolution and its Role in Solid Oral Dosage Form Development Lecture 10: Prototype Formulations Screening and Characterization NEW ecourse Available NOW! Visit for more information. How has ACS Webinars benefited you? As a pharmacologist, ACS Webinars have provided me with a better understanding of the chemistry aspects of my projects and enabled me to interact effectively with my chemist collaborators. Abir El-Alfy, Ph.D. Associate Professor, Pharmaceutical Sciences College of Pharmacy, Chicago State University Be a featured fan on an upcoming webinar! Write to acswebinars@acs.org 58 29
30 youtube.com/acswebinars Search for acswebinars and connect! 59 Benefits of ACS Membership Chemical & Engineering News (C&EN) The preeminent weekly news source. NEW! Free Access to ACS Presentations on Demand ACS Member only access to over 1,000 presentation recordings from recent ACS meetings and select events. NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more
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