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Marcel Dekker, Inc. New York BaselTM

Handbook ofPharmaceutical Analysis

edited by

Lena OhannesianMcneil Consumer Healthcare Company

Fort Washington, Pennsylvania

Antony J. StreeterThe R. W. Johnson Pharmaceutical Research Institude

Spring House, Pennsylvania

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ISBN: 0-8247-0462-2

This book is printed on acid-free paper.

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Marcel Dekker, Inc.

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Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.

Neither this book nor any part may be reproduced or transmitted in any form or by any

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PRINTED IN THE UNITED STATES OF AMERICA

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DRUGS AND THE PHARMACEUTICAL SCIENCES

Executive Editor

James Swarbrick

PharmaceuTech, Inc.Pinehurst, North Carolina

Advisory Board

Larry L. AugsburgerUniversity of Maryland

Baltimore, Maryland

David E. NicholsPurdue UniversityWest Lafayette, Indiana

Douwe D. BreimerGorlaeus Laboratories

Leiden, The Netherlands

Stephen G. SchulmanUniversity of FloridaGainesville, Florida

Trevor M. JonesThe Association of the

British Pharmaceutical IndustryLondon, United Kingdom

Jerome P. SkellyAlexandria, Virginia

Hans E. JungingerLeiden/Amsterdam Center

for Drug ResearchLeiden, The Netherlands

Felix TheeuwesAlza CorporationPalo Alto, California

Vincent H. L. LeeUniversity of Southern California

Los Angeles, California

Geoffrey T. TuckerUniversity of SheffieldRoyal Hallamshire HospitalSheffield, United Kingdom

Peter G. WellingInstitut de Recherche Jouveinal

Fresnes, France

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DRUGS AND THE PHARMACEUTICAL SCIENCES

A Series of Textbooks and Monographs

1. Pharmacokinetics, Milo Gibaldi and Donald Perrier2. Good Manufacturing Practices for Pharmaceuticals: A Plan for Total

Quality Control, Sidney H. Willig, Murray M. Tuckerman, and WilliamS. Hitchings IV

3. Microencapsulation, edited by J. R. Nixon4. Drug Metabolism: Chemical and Biochemical Aspects, Bernard Testa

and Peter Jenner

5. New Drugs: Discovery and Development, edited by Alan A. Rubin6. Sustained and Controlled Release Drug Delivery Systems, edited by

Joseph R. Robinson7. Modern Pharmaceutics, edited by Gilbert S. Banker and Christopher

T. Rhodes8. Prescription Drugs in Short Supply: Case Histories, Michael A.

Schwartz9. Activated Charcoal: Antidotal and Other Medical Uses, David O.

Cooney

10. Concepts in Drug Metabolism (in two parts), edited by Peter Jennerand Bernard Testa11. Pharmaceutical Analysis: Modern Methods (in two parts), edited by

James W. Munson12. Techniques of Solubilization of Drugs, edited by Samuel H. Yalkowsky13. Orphan Drugs, edited by Fred E. Karch14. Novel Drug Delivery Systems: Fundamentals, Developmental Con-

cepts, Biomedical Assessments, Yie W. Chien15. Pharmacokinetics: Second Edition, Revised and Expanded, Milo

Gibaldi and Donald Perrier

16. Good Manufacturing Practices for Pharmaceuticals: A Plan for TotalQuality Control, Second Edition, Revised and Expanded, Sidney H.Willig, Murray M. Tuckerman, and William S. Hitchings IV

17. Formulation of Veterinary Dosage Forms, edited by Jack Blodinger18. Dermatological Formulations: Percutaneous Absorption, Brian W.

Barry19. The Clinical Research Process in the Pharmaceutical Industry, edited

by Gary M. Matoren20. Microencapsulation and Related Drug Processes, Patrick B. Deasy

21. Drugs and Nutrients: The Interactive Effects, edited by Daphne A.Roe and T. Colin Campbell22. Biotechnology of Industrial Antibiotics, Erick J. Vandamme23. Pharmaceutical Process Validation, edited by Bernard T. Loftus and

Robert A. Nash

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24. Anticancer and Interferon Agents: Synthesis and Properties, edited byRaphael M. Ottenbrite and George B. Butler

25. Pharmaceutical Statistics: Practical and Clinical Applications, SanfordBolton

26. Drug Dynamics for Analytical, Clinical, and Biological Chemists,

Benjamin J. Gudzinowicz, Burrows T. Younkin, Jr., and Michael J.Gudzinowicz27. Modern Analysis of Antibiotics, edited by Adjoran Aszalos28. Solubility and Related Properties, Kenneth C. James29. Controlled Drug Delivery: Fundamentals and Applications, Second

Edition, Revised and Expanded, edited by Joseph R. Robinson andVincent H. Lee

30. New Drug Approval Process: Clinical and Regulatory Management,edited by Richard A. Guarino

31. Transdermal Controlled Systemic Medications, edited by Yie W.

Chien32. Drug Delivery Devices: Fundamentals and Applications, edited by

Praveen Tyle33. Pharmacokinetics: Regulatory Industrial Academic Perspectives,

edited by Peter G. Welling and Francis L. S. Tse34. Clinical Drug Trials and Tribulations, edited by Allen E. Cato35. Transdermal Drug Delivery: Developmental Issues and Research Ini-

tiatives, edited by Jonathan Hadgraft and Richard H. Guy36. Aqueous Polymeric Coatings for Pharmaceutical Dosage Forms,

edited by James W. McGinity37. Pharmaceutical Pelletization Technology, edited by Isaac Ghebre-Sellassie

38. Good Laboratory Practice Regulations, edited by Allen F. Hirsch39. Nasal Systemic Drug Delivery, Yie W. Chien, Kenneth S. E. Su, and

Shyi-Feu Chang40. Modern Pharmaceutics: Second Edition, Revised and Expanded,

edited by Gilbert S. Banker and Christopher T. Rhodes41. Specialized Drug Delivery Systems: Manufacturing and Production

Technology, edited by Praveen Tyle

42. Topical Drug Delivery Formulations, edited by David W. Osborne andAnton H. Amann

43. Drug Stability: Principles and Practices, Jens T. Carstensen44. Pharmaceutical Statistics: Practical and Clinical Applications, Second

Edition, Revised and Expanded, Sanford Bolton45. Biodegradable Polymers as Drug Delivery Systems, edited by Mark

Chasin and Robert Langer46. Preclinical Drug Disposition: A Laboratory Handbook, Francis L. S.

Tse and James J. Jaffe47. HPLC in the Pharmaceutical Industry, edited by Godwin W. Fong and

Stanley K. Lam48. Pharmaceutical Bioequivalence, edited by Peter G. Welling, Francis L.

S. Tse, and Shrikant V. Dinghe49. Pharmaceutical Dissolution Testing, Umesh V. Banakar

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50. Novel Drug Delivery Systems: Second Edition, Revised andExpanded, Yie W. Chien

51. Managing the Clinical Drug Development Process, David M. Coc-chetto and Ronald V. Nardi

52. Good Manufacturing Practices for Pharmaceuticals: A Plan for Total

Quality Control, Third Edition, edited by Sidney H. Willig and JamesR. Stoker53. Prodrugs: Topical and Ocular Drug Delivery, edited by Kenneth B.

Sloan54. Pharmaceutical Inhalation Aerosol Technology, edited by Anthony J.

Hickey55. Radiopharmaceuticals: Chemistry and Pharmacology, edited by

Adrian D. Nunn56. New Drug Approval Process: Second Edition, Revised and Expanded,

edited by Richard A. Guarino

57. Pharmaceutical Process Validation: Second Edition, Revised and Ex-panded, edited by Ira R. Berry and Robert A. Nash

58. Ophthalmic Drug Delivery Systems, edited by Ashim K. Mitra59. Pharmaceutical Skin Penetration Enhancement, edited by Kenneth A.

Walters and Jonathan Hadgraft60. Colonic Drug Absorption and Metabolism, edited by Peter R. Bieck61. Pharmaceutical Particulate Carriers: Therapeutic Applications, edited

by Alain Rolland62. Drug Permeation Enhancement: Theory and Applications, edited by

Dean S. Hsieh63. Glycopeptide Antibiotics, edited by Ramakrishnan Nagarajan64. Achieving Sterility in Medical and Pharmaceutical Products, Nigel A.

Halls65. Multiparticulate Oral Drug Delivery, edited by Isaac Ghebre-Sellassie66. Colloidal Drug Delivery Systems, edited by Jrg Kreuter67. Pharmacokinetics: Regulatory Industrial Academic Perspectives,

Second Edition, edited by Peter G. Welling and Francis L. S. Tse68. Drug Stability: Principles and Practices, Second Edition, Revised and

Expanded, Jens T. Carstensen

69. Good Laboratory Practice Regulations: Second Edition, Revised andExpanded, edited by Sandy Weinberg

70. Physical Characterization of Pharmaceutical Solids, edited by HarryG. Brittain

71. Pharmaceutical Powder Compaction Technology, edited by Gran Al-derborn and Christer Nystrm

72. Modern Pharmaceutics: Third Edition, Revised and Expanded, editedby Gilbert S. Banker and Christopher T. Rhodes

73. Microencapsulation: Methods and Industrial Applications, edited bySimon Benita

74. Oral Mucosal Drug Delivery, edited by Michael J. Rathbone75. Clinical Research in Pharmaceutical Development, edited by Barry

Bleidt and Michael Montagne

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76. The Drug Development Process: Increasing Efficiency and Cost Ef-fectiveness, edited by Peter G. Welling, Louis Lasagna, and UmeshV. Banakar

77. Microparticulate Systems for the Delivery of Proteins and Vaccines,edited by Smadar Cohen and Howard Bernstein

78. Good Manufacturing Practices for Pharmaceuticals: A Plan for TotalQuality Control, Fourth Edition, Revised and Expanded, Sidney H.Willig and James R. Stoker

79. Aqueous Polymeric Coatings for Pharmaceutical Dosage Forms:Second Edition, Revised and Expanded, edited by James W.McGinity

80. Pharmaceutical Statistics: Practical and Clinical Applications, ThirdEdition, Sanford Bolton

81. Handbook of Pharmaceutical Granulation Technology, edited by DilipM. Parikh

82. Biotechnology of Antibiotics: Second Edition, Revised and Expanded,edited by William R. Strohl

83. Mechanisms of Transdermal Drug Delivery, edited by Russell O. Pottsand Richard H. Guy

84. Pharmaceutical Enzymes, edited by Albert Lauwers and SimonScharp

85. Development of Biopharmaceutical Parenteral Dosage Forms, editedby John A. Bontempo

86. Pharmaceutical Project Management, edited by Tony Kennedy

87. Drug Products for Clinical Trials: An International Guide to Formula-tion Production Quality Control, edited by Donald C. Monkhouseand Christopher T. Rhodes

88. Development and Formulation of Veterinary Dosage Forms: SecondEdition, Revised and Expanded, edited by Gregory E. Hardee and J.Desmond Baggot

89. Receptor-Based Drug Design, edited by Paul Leff90. Automation and Validation of Information in Pharmaceutical Pro-

cessing, edited by Joseph F. deSpautz91. Dermal Absorption and Toxicity Assessment, edited by Michael S.

Roberts and Kenneth A. Walters92. Pharmaceutical Experimental Design, Gareth A. Lewis, Didier

Mathieu, and Roger Phan-Tan-Luu93. Preparing for FDA Pre-Approval Inspections, edited by Martin D.

Hynes III94. Pharmaceutical Excipients: Characterization by IR, Raman, and NMR

Spectroscopy, David E. Bugay and W. Paul Findlay95. Polymorphism in Pharmaceutical Solids, edited by Harry G. Brittain96. Freeze-Drying/Lyophilization of Pharmaceutical and Biological Prod-

ucts, edited by Louis Rey and Joan C. May97. Percutaneous Absorption: DrugsCosmeticsMechanismsMetho-

dology, Third Edition, Revised and Expanded, edited by Robert L.Bronaugh and Howard I. Maibach

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98. Bioadhesive Drug Delivery Systems: Fundamentals, Novel Ap-proaches, and Development, edited by Edith Mathiowitz, Donald E.Chickering III, and Claus-Michael Lehr

99. Protein Formulation and Delivery, edited by Eugene J. McNally100. New Drug Approval Process: Third Edition, The Global Challenge,

edited by Richard A. Guarino101. Peptide and Protein Drug Analysis, edited by Ronald E. Reid102. Transport Processes in Pharmaceutical Systems, edited by Gordon L.

Amidon, Ping I. Lee, and Elizabeth M. Topp103. Excipient Toxicity and Safety, edited by Myra L. Weiner and Lois A.

Kotkoskie104. The Clinical Audit in Pharmaceutical Development, edited by Michael

R. Hamrell105. Pharmaceutical Emulsions and Suspensions, edited by Francoise

Nielloud and Gilberte Marti-Mestres

106. Oral Drug Absorption: Prediction and Assessment, edited by JenniferB. Dressman and Hans Lennerns

107. Drug Stability: Principles and Practices, Third Edition, Revised andExpanded, edited by Jens T. Carstensen and C. T. Rhodes

108. Containment in the Pharmaceutical Industry, edited by James P.Wood

109. Good Manufacturing Practices for Pharmaceuticals: A Plan for TotalQuality Control from Manufacturer to Consumer, Fifth Edition, Revisedand Expanded, Sidney H. Willig

110. Advanced Pharmaceutical Solids, Jens T. Carstensen111. Endotoxins: Pyrogens, LAL Testing, and Depyrogenation, SecondEdition, Revised and Expanded, Kevin L. Williams

112. Pharmaceutical Process Engineering, Anthony J. Hickey and DavidGanderton

113. Pharmacogenomics, edited by Werner Kalow, Urs A. Meyer, and Ra-chel F. Tyndale

114. Handbook of Drug Screening, edited by Ramakrishna Seethala andPrabhavathi B. Fernandes

115. Drug Targeting Technology: Physical Chemical Biological Methods,

edited by Hans Schreier116. DrugDrug Interactions, edited by A. David Rodrigues117. Handbook of Pharmaceutical Analysis, edited by Lena Ohannesian

and Anthony J. Streeter118. Pharmaceutical Process Scale-Up, edited by Michael Levin119. Dermatological and Transdermal Formulations, edited by Kenneth A.

Walters120. Clinical Drug Trials and Tribulations: Second Edition, Revised and

Expanded, edited by Allen Cato, Lynda Sutton, and Allen Cato III121. Modern Pharmaceutics: Fourth Edition, Revised and Expanded, edi-

ted by Gilbert S. Banker and Christopher T. Rhodes122. Surfactants and Polymers in Drug Delivery, Martin Malmsten123. Transdermal Drug Delivery: Second Edition, Revised and Expanded,

edited by Richard H. Guy and Jonathan Hadgraft

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124. Good Laboratory Practice Regulations: Second Edition, Revised andExpanded, edited by Sandy Weinberg

125. Parenteral Quality Control: Sterility, Pyrogen, Particulate, and Pack-age Integrity Testing: Third Edition, Revised and Expanded, MichaelJ. Akers, Daniel S. Larrimore, and Dana Morton Guazzo

126. Modified-Release Drug Delivery Technology, edited by Michael J.Rathbone, Jonathan Hadgraft, and Michael S. Roberts127. Simulation for Designing Clinical Trials: A Pharmacokinetic-Pharma-

codynamic Modeling Perspective, edited by Hui C. Kimko and Ste-phen B. Duffull

128. Affinity Capillary Electrophoresis in Pharmaceutics and Biopharma-ceutics, edited by Reinhard H. H. Neubert and Hans-Hermann Rt-tinger

129. Pharmaceutical Process Validation: An International Third Edition,Revised and Expanded, edited by Robert A. Nash and Alfred H.

Wachter130. Ophthalmic Drug Delivery Systems: Second Edition, Revised and

Expanded, edited by Ashim K. Mitra131. Pharmaceutical Gene Delivery Systems, edited by Alain Rolland and

Sean M. Sullivan

ADDITIONAL VOLUMES IN PREPARATION

Biomarkers in Clinical Drug Development, edited by John Bloom

Pharmaceutical Inhalation Aerosol Technology: Second Edition, Re-vised and Expanded, edited by Anthony J. Hickey

Pharmaceutical Extrusion Technology, edited by Isaac Ghebre-Sellas-sie and Charles Martin

Pharmaceutical Compliance, edited by Carmen Medina

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To our daughters, Taleen, Sareen, and Aleen, for their patience and understanding

for all the time, on top of our very demanding careers, that we took up working

on assembling this book. May their lives be filled with the same curiosity and

joy that we find in science, in whatever experiences the future brings to them.

pyright 2002 by Marcel Dekker. All Rights Reserved.

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Preface

Twenty years have passed since the publication of the first volume of Pharmaceu-

tical Analysis, which has since evolved into the Handbook of Pharmaceutical

Analysis. The original two volumes succeeded in concisely filling the gap be-

tween undergraduate text and detailed monograph on pharmaceutical analysis for

practitioners of the pharmaceutical sciences. As with other branches of science,the technologies employed in pharmaceutical analysis today have advanced tre-

mendously over the last two decades, with methodologies becoming routine that

were purely experimental a few years ago.

Our goals in preparing this revised version were to bring the text up to

date with the most important developments in the field of pharmaceutical analysis

while still preserving the scope and level of coverage of our previous texts. We

have tried to maintain the intermediate level of coverage throughout the book,

with each chapter containing detailed descriptions of theory, instrumentation, and

applications, as well as pertinent references. We decided to combine the chaptersinto a single volume for convenience and thus it is being published as a single,

authoritative handbook. This book is not intended to be a comprehensive resource

in itself, but to give the reader background information on the most widely used

techniques and, with almost 2000 references, to direct the reader to more detailed

sources in the scientific literature.

We have included many of the chapters from Pharmaceutical Analysis, in

updated form, since they continue to provide the backbone of pharmaceutical

analysis for the book. However, because of their limited applications in modern

pharmaceutical analysis, we have elected not to include some chapters such as

pyright 2002 by Marcel Dekker. All Rights Reserved.

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those on thin-layer chromatography, pyrolysis-gas chromatography, gas chroma-

tography, and functional group analysis.

Before you can perform any of the analytical techniques described in this

book, it is first necessary to obtain your drug substance. It is becoming clearer

that many drugs can exist in different polymorphic forms, which can behave very

differently from one another during formulation and after administration. Chapter1 addresses this topic. Chapter 2 deals with the techniques that are often necessary

for separating the drug from the other components of a pharmaceutical formula-

tion or biological sample and/ or preparing the drug sample for one of the analyti-

cal methods that are covered in later chapters. This chapter also introduces the

reader to the concept of validation for assays of drugs in plasma, which, since

the results of these measurements are critical in determining the safety margins

for exposure in humans versus animals in toxicity studies, is subject to close

scrutiny by regulatory authorities during the approval of new drugs. The sound

scientific principles that underlie the FDA guidances in this area have, by a pro-

cess of osmosis, influenced government and academia as well.

Following Chapter 3 on high-performance liquid chromatography, we have

included a chapter on the many new applications of mass spectrometry. This

technique, usually in combination with high-performance liquid chromatography,

has become the mainstay of metabolite or decomposition product identification,

and its great potential for selectivity and sensitivity has proven invaluable for

many drug and metabolite assays. The various techniques applied to high-perfor-

mance liquid chromatography for removing the chromatographic solvents andintroducing the solutes directly into the mass spectrometer, without the need for

extraction, derivatization or heating, make high-performance liquid chromatogra-

phy coupled with mass spectrometry especially valuable for peptides and heat

labile molecules.

Chapter 5 covers ultravioletvisible spectroscopy and Chapter 6, on immu-

noassay techniques, emphasizes the wide array of new methodologies that do

not use radioisotopes. Chapter 7 discusses one of the most novel techniques for

chromatographic separation of moleculescapillary electrophoresisand its

widespread applications to pharmaceuticals. Chapter 8, Atomic Spectroscopy,and Chapter 9, Luminescence Spectroscopy, contain current information on

these important technologies.

Chapter 10, on nuclear magnetic resonance spectroscopy was included be-

cause of the unique role that nuclear magnetic resonance spectroscopy has in the

study of polymorphisms as well as in verification of compound identity and the

structural confirmation of metabolic or decomposition products of drugs. Chapter

11, Vibrational Spectroscopy, reflects the invaluable contributions that those

techniques such as infrared spectroscopy have made to the analysis of formula-

tions, among other studies.

pyright 2002 by Marcel Dekker. All Rights Reserved.

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Finally, we could not ignore another area in which the regulatory authorities

have had a major impact on pharmaceutical analysis in the pharmaceutical indus-

try. Our concluding chapter deals with process validation as it applies to pharma-

ceutical analysis.

Lena OhannesianAnthony J. Streeter

pyright 2002 by Marcel Dekker. All Rights Reserved.

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Contents

Preface

Contributors

1. Form Selection of Pharmaceutical Compounds

Ann W. Newman and G. Patrick Stahly

2. Preparation of Drug Samples for Analysis

David E. Nadig

3. High-Performance Liquid Chromatography

Thomas H. Stout and John G. Dorsey

4. Mass Spectroscopy in Pharmaceutical Analysis

Frank J. Belas and Ian A. Blair

5. UltravioletVisible Spectroscopy

John H. Miyawa and Stephen G. Schulman

6. Immunoassay Techniques

Jean W. Lee and Wayne A. Colburn

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7. Applications of Capillary Electrophoresis Technology in the

Pharmaceutical Industry

Charles J. Shaw and Norberto A. Guzman

8. Atomic Spectroscopy

Helen E. Taylor and Stephen G. Schulman

9. Luminescence Spectroscopy

John H. Miyawa and Stephen G. Schulman

10. Solid-State Nuclear Magnetic Resonance Spectroscopy

David E. Bugay

11. Vibrational Spectroscopy

David E. Bugay and W. Paul Findlay

12. Statistical Considerations in Pharmaceutical Process

Development and Validation

Gerald J. Mergen

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Contributors

Frank J. Belas* Center for Cancer Pharmacology, University of Pennsylvania,

Philadelphia, Pennsylvania

Ian A. Blair Center for Cancer Pharmacology, University of Pennsylvania,

Philadelphia, Pennsylvania

David E. Bugay SSCI, Inc., West Lafayette, Indiana

Wayne A. Colburn MDS Pharma Services, Phoenix, Arizona

John G. Dorsey Department of Chemistry, Florida State University, Tallahas-

see, Florida

W. Paul Findlay Department of Industrial and Physical Pharmacy, Purdue

University, West Lafayette, Indiana

Norberto A. Guzman The R. W. Johnson Pharmaceutical Research Institute,

Raritan, New Jersey

Jean W. Lee MDS Pharma Services, Lincoln, Nebraska

* Current affiliation: Lilly Research Laboratories, Lilly Corporate Center, Indianapolis, Indiana.

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Gerald J. Mergen McNeil Consumer Healthcare Company, Fort Washington,

Pennsylvania

John H. Miyawa College of Pharmacy, University of Florida, Gainesville,

Florida

David E. Nadig The R. W. Johnson Pharmaceutical Research Institute, Rari-

tan, New Jersey

Ann W. Newman SSCI, Inc., West Lafayette, Indiana

Stephen G. Schulman College of Pharmacy, University of Florida, Gaines-

ville, Florida

Charles J. Shaw The R. W. Johnson Pharmaceutical Research Institute, Rari-

tan, New Jersey

G. Patrick Stahly SSCI, Inc., West Lafayette, Indiana

Thomas H. Stout* Department of Chemistry, University of Cincinnati, Cincin-

nati, Ohio

Helen E. Taylor College of Pharmacy, University of Florida, Gainesville,Florida

* Current affiliation: Eurand America, Inc., Vandalia, Ohio.