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Biodegradable Polymers in Clinical Use, Development - A. Domb, et. al., Wiley, 2011) WW PDF

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BIODEGRADABLE POLYMERS IN CLINICAL USE AND CLINICAL DEVELOPMENT FFIRS 14 April 2011; 12:37:33 BIODEGRADABLE POLYMERS IN CLINICAL USE AND CLINICAL DEVELOPMENT Edited by Abraham J. Domb Institute for Drug Design, Medicinal Chemistry School of Pharmacy � Faculty of Medicine The Hebrew University, Jerusalem, Israel Neeraj Kumar National Institute of Pharmaceutical Education and Research (NIPER), S.A.S. Nagar, Punjab, India Aviva Ezra Institute for Drug Design, Medicinal Chemistry School of Pharmacy � Faculty of Medicine The Hebrew University, Jerusalem, Israel FFIRS 14 April 2011; 12:37:33 Copyright r 2011 by John Wiley & Sons, Inc. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permission. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data: Biodegradable Polymers in Clinical Use and Clinical Development / edited by Abraham J. Domb, Neeraj Kumar, and Aviva Ezra. p. cm Includes index. ISBN 978-0-470-42475-9 (hardback) 1. Polymers in medicine. 2. Biodegradable plastics. I. Domb, A. J. (Abraham J.), editor of compilation. II. Jain, Jay Prakash. Biodegradable polymers in drug delivery. R857.P6B537 2011 610.28u4–dc22 2010043471 Printed in Singapore oBook ISBN: 9781118015810 ePDF ISBN: 9781118015797 ePub ISBN: 9781118015803 10 9 8 7 6 5 4 3 2 1 FFIRS 14 April 2011; 12:37:34 CONTENTS CONTRIBUTORS ix PREFACE xiii PART I GENERAL 1 1 Biodegradable Polymers in Drug Delivery 3 Jay Prakash Jain, Wubante Yenet, Abraham J. Domb, and Neeraj Kumar PART II BIODEGRADABLE POLYMERS OF NATURAL ORIGIN: PROTEIN-BASED POLYMERS 59 2 Collagen 61 Wahid Khan, Deepak Yadav, Abraham J. Domb, and Neeraj Kumar 3 Properties and Hemostatic Application of Gelatin 91 Jalindar Totre, Diana Ickowicz, and Abraham J. Domb PART III BIODEGRADABLE POLYMERS OF NATURAL ORIGIN: POLYSACCHARIDES 111 4 Chitosan and Its Derivatives in Clinical Use and Applications 113 Anuradha Subramanian, Kirthanashri Srinivasan Vasanthan, Uma Maheswari Krishnan, and Swaminathan Sethuraman 5 Clinical Uses of Alginate 137 Udi Nussinovitch and Amos Nussinovitch v TOC 14 April 2011; 17:25:12 6 Dextran and Pentosan Sulfate — Clinical Applications 185 Ramu Parthasarathi and Athipettah Jayakrishnan 7 Arabinogalactan in Clinical Use 217 Rajendra P. Pawar, Babasaheb A. Kushekar, Bhaskar S. Jadhav, Kiran R. Kharat, Ravikumar M. Borade, and Abraham J. Domb PART IV BIODEGRADABLE POLYMERS OF NATURAL ORIGIN: POLYESTERS 247 8 Polyhydroxyalkanoate 249 Kesaven Bhubalan, Wing-Hin Lee, and Kumar Sudesh PART V SYNTHETIC BIODEGRADABLE POLYMERS 317 9 Lactide and Glycolide Polymers 319 Kevin Letchford, Anders So¨dergard, David Plackett, Samuel Gilchrist, and Helen Burt 10 Polyanhydrides�Poly(CPP-SA), Fatty-Acid-Based Polyanhydrides 367 Ravikumar M. Borade, Abraham J. Domb, Archana A. Sawale, Rajendra P. Pawar, and Kiran R. Kharat 11 Poly(e-Caprolactone-co-Glycolide): Biomedical Applications of a Unique Elastomer 401 Kevin Cooper, Aruna Nathan, and Murty Vyakarnam 12 Medicinal Applications of Cyanoacrylate 417 Rajendra P. Pawar, Ashok E. Jadhav, Sumangala B. Tathe, Bhimrao C. Khade, and Abraham J. Domb 13 Polyethylene Glycol in Clinical Application and PEGylated Drugs 451 Teerapol Srichana, and Tan Suwandecha PART VI INORGANIC POLYMERS 495 14 Calcium-Phosphate-Based Ceramics for Biomedical Applications 497 Qing Lv, Kevin W.-H. Lo, Lakshmi S. Nair, and Cato T. Laurencin vi CONTENTS TOC 14 April 2011; 17:25:12 PART VII BIODEGRADABLE POLYMERS FOR EMERGING CLINICAL USES 519 15 Biocompatible Polymers for Nucleic Acid Delivery 521 Jeff Sparks, and Khursheed Anwer 16 Biodegradable Polymers for Emerging Clinical Use in Tissue Engineering 565 Shalini Verma, Kalpna Garkhal, Anupama Mittal, and Neeraj Kumar 17 Injectable Polymers 631 Shimon A. Unterman, Norman A. Marcus, and Jennifer H. Elisseeff PART VIII IPR ASPECTS OF BIODEGRADABLE POLYMERS 665 18 Global Patent and Technological Status of Biodegradable Polymers in Drug Delivery and Tissue Engineering 667 Parikshit Bansal, Shalini Verma, Wahid Khan, and Neeraj Kumar Index 727 CONTENTS VII TOC 14 April 2011; 17:25:12 CONTRIBUTORS KHURSHEED ANWER, EGEN, Inc., Huntsville, Alabama PARIKSHIT BANSAL, Intellectual Property Right (IRR) Cell, Department of Pharmaceutical Management, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India KESAVEN BHUBALAN, Department of Marine Science, Faculty of Maritime Studies and Marine Science, Universiti Malaysia Terengganu, Terengganu, Malaysia RAVIKUMAR M. BORADE, Department of Chemistry, Government Arts and Science College, Aurangabad, Maharashtra, India HELEN BURT, Faculty of Pharmaceutical Sciences, University of British Columbia, Vancouver, Canada KEVIN COOPER, ARUNA NATHAN, MURTY VYAKARNAM, Advanced Technologies and Regenerative Medicine, Somerville, NJ. ABRAHAM J. DOMB, Institute for Drug Research, School of Pharmacy, Faculty of Medicine, The Hebrew University, Jerusalem, Israel JENNIFER H. ELISSEEFF, Department of Biomedical Engineering, Johns Hopkins University, Baltimore, Maryland KALPNA GARKHAL, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India SAMUEL GILCHRIST, Faculty of Pharmaceutical Sciences, University of British Columbia, Vancouver, Canada DIANA ICKOWICZ, Institute for Drug Research, School of Pharmacy, Faculty of Medicine, The Hebrew University, Jerusalem, Israel ASHOK E. JADHAV, Organic Chemistry Synthesis Laboratory, Dnyanopasak College, Maharashtra, India BHASKAR S. JADHAV, Department of Chemistry, Deogiri College, Maharashtra, India ix FLAST 14 April 2011; 12:37:58 JAY PRAKASH JAIN, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India A. JAYAKRISHNAN, Department of Biotechnology, Indian Institute of Technology, Chennai, India BHIMRAO C. KHADE, Organic Chemistry Synthesis Laboratory, Dnyanopasak College, Maharashtra, India WAHID KHAN, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India KIRAN R. KHARAT, Department of Biotechnology, Deogiri College, Aurangabad, Maharashtra, India UMA MAHESWARI KRISHNAN, Center of Nanotechnology & Advanced Biomaterials, School of Chemical & Biotechnology, SASTRA University, Tamil Nadu, India NEERAJ KUMAR, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India BABASAHEB A. KUSHEKAR, Department of Chemistry, Deogiri College, Maharashtra, India CATO T. LAURENCIN, The University of Connecticut, Farmington, CT. WING-HIN LEE, Ecobiomaterial Research Laboratory, School of Biological Sciences, Universiti Sains Malaysia, Malaysia KEVIN LETCHFORD, Faculty of Pharmaceutical Sciences, University of British Columbia, Vancouver, Canada KEVIN W.-H. LO, The University of Connecticut, Farmington, CT. QING LV, The University of Connecticut, Farmington, CT. NORMAN A. MARCUS, Department of Biomedical Engineering, Johns Hopkins University, Baltimore, Maryland ANUPAMA MITTAL, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India LAKSHMI NAIR, The University of Connecticut, Farmington, CT. AMOS NUSSINOVITCH, Institute of Biochemistry, Food Science and Nutrition, The Robert H. Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, Rehovot, Israel UDI NUSSINOVITCH, Department of Medicine B, Chaim Sheba Medical Center, Tel Hashomer, Israel x CONTRIBUTORS FLAST 14 April 2011; 12:37:58 RAMU PARTHASARATHY, Department of Biotechnology, Indian Institute of Technology, Chennai, India RAJENDRA P. PAWAR, Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, India DAVID PLACKETT, Risø National Laboratory for Sustainable Energy, Technical University of Denmark, Roskilde, Denmark ARCHANA A. SAWALE, Department of Chemistry, Viva College, Virar (W), Dist. Thane, Maharashtra, India SWAMINATHAN SETHURAMAN, Center of Nanotechnology & Advanced Biomaterials, School of Chemical & Biotechnology, SASTRA University, Tamil Nadu, India ANDERS SO¨ DERGARD, Abo Akademi Univerisity, Laboratory of Polymer Technology, Turku, Finland JEFF SPARKS, EGEN, Inc., Huntsville, Alabama TEERAPOL SRICHANA, Drug Delivery System Excellence Center, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hatyai, Songkla, Thailand ANURADHA SUBRAMANIAN, Center of Nanotechnology & Advanced Biomaterials, School of Chemical & Biotechnology, SASTRA University, Tamil Nadu, India KUMAR SUDESH, Ecobiomaterial Research Laboratory, School of Biological Sciences, Universiti Sains Malaysia, Malaysia TAN SUWANDECHA, Drug Delivery System Excellence Center, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hatyai, Songkla, Thailand SUMANGALA B. TATHE, Organic Chemistry Synthesis Laboratory, Dnyanopasak College, Maharashtra, India JALINDER TOTRE, Institute for Drug Research, School of Pharmacy, The Hebrew University, Jerusalem, Israel SHIMON A. UNTERMAN, Department of Biomedical Engineering, Johns Hopkins University, Baltimore, Maryland KIRTHANASHRI SRINIVASAN VASANTHAN, Center of Nanotechnology & Advanced Biomaterials, School of Chemical & Biotechnology, SASTRA University, Tamil Nadu, India SHALINI VERMA, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India CONTRIBUTORS xi FLAST 14 April 2011; 12:37:58 DEEPAK YADAV, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India WUBANTE YENET, Department of Pharmaceutics, National Institute of Pharmaceutical Education and Research (NIPER), Punjab, India xii CONTRIBUTORS FLAST 14 April 2011; 12:37:58

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