Recent Advancement in Prodrugs PDF
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Recent Advancement in Prodrugs Recent Advancement in Prodrugs Edited by Kamal Shah Durgesh Nandini Chauhan Nagendra Singh Chauhan Pradeep Mishra First edition published 2020 by CRC Press 6000 Broken Sound Parkway NW, Suite 300, Boca Raton, FL 33487-2742 and by CRC Press 2 Park Square, Milton Park, Abingdon, Oxon, OX14 4RN © 2020 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper International Standard Book Number-13: 978-0-367-34836-6 (Hardback) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. 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Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface .....................................................................................................................................................vii Editors .......................................................................................................................................................ix Contributors ..............................................................................................................................................xi 1. Recent Advancements in New Drug Design and Development of Prodrugs ..............................1 Kamal Shah, Gaurav Krishna, Jeetendra Kumar Gupta, Durgesh Nandini Chauhan, Nagendra Singh Chauhan, and Pradeep Mishra 2. Codrugs: Optimum Use through Prodrugs .................................................................................21 Suneela Dhaneshwar, Poorvashree P. Joshi, and Shubham Pawar 3. Role of Prodrugs in Drug Design..................................................................................................67 Asadullah Madni, Sobia Noreen, Afifa Shafique, Abdur Rahim, Muhammad Sarfraz, and Attia Afzal 4. Prodrugs for Enhancement of Lipophilicity................................................................................93 Suneela Dhaneshwar and Neha V. Bhilare 5. Lipidic Prodrugs for Drug Delivery: Opportunities and Challenges ......................................113 Milica Markovic, Shimon Ben-Shabat, and Arik Dahan 6. The Progress of Prodrugs in Drug Solubility .............................................................................133 Guilherme Felipe dos Santos Fernandes, Igor Muccilo Prokopczyk, Chung Man Chin, and Jean Leandro dos Santos 7. Prodrugs for CNS Drug Delivery ................................................................................................165 Katalin Prokai-Tatrai 8. Prodrugs for Cancer Treatment ..................................................................................................185 William L. Stone, Victoria E. Palau, and K. Krishnan 9. Prodrugs in Cancer Nanomedicine and Therapy .....................................................................201 Vikas Pandey, Tanweer Haider, Vishal Gour, Vandana Soni, and Prem N. Gupta 10. Nitroreductases in Prodrug Therapies ......................................................................................227 Tuğba Güngör, Ferah Cömert Önder, and Mehmet Ay 11. Prodrug Approach Using Carboxylesterase: Different Substrate Specificities of Human Carboxylesterase Isozymes .......................................................................................253 Masato Takahashi and Masakiyo Hosokawa 12. Mathematical Models for ADME of Prodrugs ..........................................................................269 Vipin Bhati, Navyashree V., Shamsher Singh, Pooja Chawla, and Anoop Kumar v vi Contents 13. Prodrug Approaches for Natural Products ...............................................................................285 Sudhir Kumar Thukral, Pooja Chawla, Alok Sharma, and Viney Chawla 14. Biotechnology-Based Prodrug Approach for Cell-Specific Targeting: Its Theoretical Basis and Application .........................................................................................317 Sunita Minz, Manju Rawat Singh, Deependra Singh, Arun Singh Parihar, and Madhulika Pradhan Index .......................................................................................................................................................333 Preface Prodrugs are said to be bioreversible derivatives which on biotransformation change into active pharmacophore. A prodrug approach has been extensively studied among drug design scientists for a wide range of applications. It has been successfully applied to encompassing a variety of various goals achieved not only for correction of pharmacokinetic behavior but also pharmaceutical, organoleptic, physical and chemical properties of parent drug compound which enhance the stability and patient compliance, improving the efficacy of therapy. An ideal prodrug has favorable administration, distribu- tion, metabolism, excretion, and toxicity (ADMET) properties, is chemically stable in its dosage form, releases the active drug molecule at an appropriate rate at the desired site in the body, and releases a promoiety that is non-toxic. Since a large number of potential drugs or drug candidates have undesirable properties that may present pharmaceutical, pharmacokinetic, pharmacodynamic, or economical barri- ers to their clinical application, prodrugs should be considered as one potential solution in the early stage of drug design and development. They have to pass through enzymatic or chemical biotransformation before eliciting their pharmacological action. The prodrug concept may be used in case of solubility enhancement, bioavailability enhancement, chemical stability improvement, presystemic metabolism, site-specific delivery, toxicity masking, improving patient acceptance, or eradicating undesirable adverse effects. This book is aimed at an audience of advanced-level students, experts, and scientists working in prodrugs designing and synthesis. The book is a single window reference source to the industrial chem- istry community. This book has an emphasis on application and its implementation in research as well as in pharmaceutical industries. This book consists of 14 chapters. Chapter 1 has brief descriptions about different types of prodrugs, with examples and their potential application. This chapter is proposed to encourage scientists look- ing for innovative prodrug approaches and rationally designed drug discovery platforms. Chapter 2 describes challenges encountered during development, toxicological and regulatory aspects and some FDA-approved codrugs. Overall, a codrug approach is a versatile, powerful tool that can be applied to a wide range of drugs to improve their therapeutic efficacy, bioavailability, and minimize side effects. Chapter 3 has recent examples of prodrugs from literature on the basis of linkages present in prodrugs. Their applications with the aim of its synthesis were discussed in this chapter. Chapter 4 highlights the applications of a prodrug approach in offering an attractive substitute for improving lipophilicity and thus eliminating various drug-related drawbacks like poor absorption, extensive first pass metabolism, poor bioavailability, foul odor, and taste, as illustrated by various examples. Lipidic prodrug approach is the focus of Chapter 5, and it presents a strategy of covalently binding a lipid carrier (fatty acids, tri- glycerides, steroids, or phospholipids) to the drug moiety. Chapter 6 describes the progress of modifying drug solubility using a prodrug approach. The chemical carriers used in the process and the examples of strategies that were successful in this regard are presented in order to comprehend better usage of this approach in the field of drug design. Chapter 7 covers valuable information regarding the challenges faced during the drug design of the central nervous system. The chapter is focused on delivery of drug by keeping basis of prodrugs by using examples so that the drug can be designed. Chapter 8 discusses the activation, role, and applicability of prodrugs in the treatment of cancer. Chapter 9 discusses prodrugs for cancer therapy. In this chapter, emphasis is placed on oxidative stress biomarkers which could serve against cancer and simultaneously provide the basis for targeted pro- oxidant chemotherapy when combined with a biomarker for oxidized protein hydrolase. Chapter 10 focuses on the new approaches in prodrug therapies developed by nitroreductases. These nitrore- ductases have been developed for prodrug strategies and nitroaromatic compounds are mostly used in this enzyme/prodrug combinations. Chapter 11 describes the development of prodrugs, including an approach using carboxylesterase with different substrate specificities of human carboxylesterase isozymes. Chapter 12 familiarizes the reader with the various mathematical models for ADME of vii viii Preface prodrugs. In addition, current challenges and future perspectives are discussed. Chapter 13 discusses secondary metabolites obtained from natural sources which serve as prodrugs for the advent of novel drugs, assuring a committed concept which can open new vistas for difficult and expensive tasks of new drug investigation. Chapter 14 highlights the biotechnological tools to be used in prodrug therapy. The chapter highlights antibody-directed enzyme prodrug therapy, gene prodrug therapy (bacterial vector-based gene prodrug therapy and viral vector-based enzyme prodrug therapy), and membrane transporters–assisted prodrug therapy. We would like to express our sincere gratitude to all of the authors who have taken time from their busy schedules to be part of this project and written wonderful chapters that added to both the depth and value of this book. We welcome suggestions and criticisms from our readers. Special thanks to our families for their support and encouragement. We express our gratitude to the publishing and production team of CRC Press, Renu Upadhyay, Shikha Garg and Jyotsna Jangra, especially for their kind, profi- cient, and encouraging guidance. Kamal Shah Durgesh Nandini Chauhan Nagendra Singh Chauhan Pradeep Mishra Editors Dr. Kamal Shah graduated from Rajiv Gandhi Proudyogiki Vishwavidyalaya, Bhopal (MP), India, and was awarded the Chancellor Gold Medal and Smt. Kamla Chaturvedi Memorial Award for securing the first position (BPharma). He qualified for GATE 2003 and GATE 2005 (IIT, Mumbai). He received his Master’s degree in 2006 from Dr. H.S. Gour University Sagar and worked on method development for determina- tion of pharmacological active components by UV and HPLC. He com- pleted his doctorate from Dr. A.P.J. Abdul Kalam Technical University, Lucknow. Currently he is working as an associate professor in the Institute of Pharmaceutical Research, GLA University Mathura (UP), India. He has published his research work in various journals of national and international repute, and has a total of 30 published research papers and more than 300 citations to his credit. He is a member of various professional and academic bodies including the Association of Pharmaceutical Teachers of India (APTI), the Institutional Animal Ethical Committee (IAEC), and the Board of Studies (BOS). He is a reviewer for various national and international journals, including Medicinal Chemistry Research, Pakistan Journal of Pharmaceutical Sciences, Journal of Sexual Medicine, Natural Product Research, African Journal of Pharmacy and Pharmacology, International Journal of Pharmacy and Pharmacology, International Research Journal of Pure and Applied Chemistry, Pharmaceutical Biology and Asian Journal of Pharmaceutics. He has also written six chapters and edited one book. His area of interest is the synthesis and evalua- tion of prodrugs of NSAIDs. Mrs. Durgesh Nandini Chauhan, MPharma, completed her BPharma degree in at the Rajiv Gandhi Proudyogiki Vishwavidyalaya, Bhopal, India, and her MPharma (pharmaceutical sciences) at Uttar Pradesh Technical University, currently Dr. A.P.J. Abdul Kalam Technical University, Lucknow, in 2006. Mrs. Durgesh Nandini Chauhan has 10 years of academic (teaching) experience from insti- tutes in India. She taught subjects such as pharmaceutics, pharmacog- nosy, traditional concepts of medicinal plants, drug-delivery phytochemistry, cosmetic technology, pharmaceutical engineering, pharmaceutical packaging, quality assurance, dosage form designing, and anatomy and physiology. She is a member of the Association of Pharmaceutical Teachers of India, SILAE: Società Italo-Latinoamericana di Etnomedicina (the Scientific Network on Ethnomedicine, Italy), and so forth. Her previous research work included “Penetration Enhancement Studies on Organogel of Oxytetracycline HCL.” She also attended an AICTE-sponsored staff development program on the “Effects of Teaching and Learning Skills in Pharmacy-Tool for Improvement of Young Pharmacy Teachers” and a workshop on analytical i nstruments. She has written more than 10 publications in national and international journals, 13 book chapters, and authored four books. She is also active as a reviewer for several international scientific journals and active participant in national and international conferences such as Bhartiya Vigyan Sammelan and ix
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