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Radiochemical Syntheses, Volume 1, Radiopharmaceuticals for Positron Emission Tomography

Peter J. H. Scott (Editor), Brian G. Hockley (Editor), Michael R. Kilbourn (Foreword by)
ISBN: 978-0-470-58895-6
368 pages
March 2012
Radiochemical Syntheses, Volume 1, Radiopharmaceuticals for Positron Emission Tomography (0470588950) cover image
The ultimate reference guide to the synthesis of radiopharmaceuticals

The Radiochemical Syntheses series provides scientists and professionals with a comprehensive reference to proven synthetic methods for radiochemical reactions, along with step-by-step guidance on how to replicate these syntheses in the laboratory.

Volume 1 in the series focuses on the synthesis and purification of radiopharmaceuticals in clinical use today. It brings together in one complete, self-contained volume a collection of monographs containing a wealth of practical information from across the literature, demonstrating in meticulous detail how to prepare radiopharmaceuticals for positron emission tomography (PET) imaging, especially in tumor studies, cardiology, and neuroscience.

Readers have key experimental details culled from the literature at their fingertips, greatly simplifying the process of qualifying a site for the clinical production of new radiopharmaceuticals.

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Contributors ix

Foreword xvii

Preface xix

Abbreviations xxi

Part 1: Fluorine-18 Labeled Radiopharmaceuticals 1

Chapter 1: Synthesis of [18F]Fluorodeoxyglucose ([18F]FDG) 3
Michelle Richards and Peter J. H. Scott

Chapter 2: Synthesis of [18F]Sodium Fluoride ([18F]NaF) 15
Brian Hockley and Peter J. H. Scott

Chapter 3: Radiosynthesis of 3'-Deoxy-3'-[18F]Fluorothymidine ([18F]FLT) 21
Hartmuth C. Kolb, Henry Padgett, Steve Zigler, Jim Patanella, Fanrong Mu, Umesh Gangadharmath, Vani P. Mocharla, Peter J. H. Scott‡ and Joseph C. Walsh

Chapter 4: Synthesis of [18F]Fluoroazomycin arabinoside (18F-FAZA) 31
Brian G. Hockley and Peter J. H. Scott

Chapter 5: Synthesis of [18F]Fluoromisonidazole (1-(2-Hydroxy-3-[18F]fluoropropyl)-2-nitroimidazole, [18F]FMISO) 41
Patrick J. Riss, Valentina Ferrari, Robbie Bielik, Roberto Canales-Candela, Rob Smith, and Franklin I. Aigbirhio

Chapter 6: Synthesis of [18F]FPPRGD2 51
Shuanglong Liu, Frederick T. Chin, Zhen Cheng and Xiaoyuan Chen

Chapter 7: Synthesis of [18F]Fluorocholine ([18F]FCH) 61
David Kryza

Chapter 8: Clinical Manufacturing of [18F]-16-a-Fluoroestradiol ([18F]FES) 69
Piyush Kumar and John R. Mercer

Chapter 9: Synthesis of N-Succinimidyl 4-[18F]Fluorobenzoate ([18F]SFB) 81
Xia Shao

Chapter 10: synthesis of 4-(2´-Methoxyphenyl)-1-[2'-(N-2''-pyridinyl)-p-[18F]fluorobenzamido]ethylpiperazine ([18F]MPPF) 87
Marion Alvarez and Didier Le Bars

Chapter 11: Synthesis of [18F]Fallypride 95
Laurent Brichard, Valentina Ferrari, Rob Smith, and Franklin I. Aigbirhio

Chapter 12: Synthesis of [18F]Fluoroethyltyrosine ([18F]FET) 103
Y. Zhao, A. Alfteimi and M. Zuhayra

Chapter 13: Synthesis of [18F]Flumazenil ([18F]FZ) 111
Ralf Schirrmacher, Alexey Kostikov, Gassan Massaweh, Miriam Kovacevic, Carmen Wängler, Alexander Thiel

Chapter 14: Synthesis of 6-[18F]Fluorodopamine (6-[18F]FDA) 125
Michael A. Channing, John L. Musachio, and Jozef J. Kusmierz

Chapter 15: Synthesis of 2-([18F]fluoro)-3-[(2S)-2-Azetidinylmethoxy]Pyridine ([18F]2FA) 139
Hayden T. Ravert, Daniel P. Holt and Robert F. Dannals

Chapter 16: Synthesis of [18F]-Substance-P Antagonist-receptor Quantifier ([18F]SPA-RQ) 155
Sofie Celen, Kim Serdons, Tjibbe de Groot, Terence G. Hamill, and Guy Bormans

Part 2: Carbon-11 Labeled Radiopharmaceuticals 167

Chapter 17: SYNTHESIS OF [11C]-Choline Chloride ([11C]CHL) 169
Brian G. Hockley, Bradford Henderson and Xia Shao

Chapter 18: Synthesis of 2-(4-N-[11C]methylaminophenyl)-6-hydroxybenzothiazole ([11C]6-OH-BTA-1; [11C]PIB) 177
Cécile Philippe, Markus Mitterhauser and Wolfgang Wadsak

Chapter 19: Synthesis of [11C]-Meta-hydroxyephedrine ([11C]MHED) 191
Filippo Lodi, Assunta Carpinelli, Claudio Malizia and Stefano Boschi

Chapter 20: Synthesis of L-[methyl-11C]Methionine ([11C]MET) 199
Amy L. Vavere and Scott E. Snyder

Chapter 21: Synthesis of (+)-α-[11C]-Dihydrotetrabenazine ([11C]DTBZ) 213
Michael R. Kilbourn

Chapter 22: Synthesis of [11C]Flumazenil([11C]FMZ) 221
Roberto Canales-Candela, Patrick J. Riss and Franklin I. Aigbirhio

Chapter 23: Synthesis of [11C]-Hexadecanoic Acid ([11C]Palmitic Acid) 233
Adam C. Runkle, Xia Shao and Peter J. H. Scott

Chapter 24: Synthesis of [O-Methyl-11C]Metomidate ([11C]MTO) 245
István. Boros and Franklin I. Aigbirhio

Chapter 25: Synthesis of [11C]Carfentanil ([11C]CFN) 257
Louis Tluczek and Xia Shao

Chapter 26: Synthesis of [carbonyl-11C]WAY-100635 265
J. D. Andersson, S. Nag, R. Krasikova, V.W. Pike and C. Halldin

Chapter 27: Synthesis of [11C]Raclopride 275
Xia Shao

Chapter 28: Synthesis of 3-Amino-4-[2-(N-Methyl-N-[11C]Methyl-Amino-Methyl)Phenylsulfanyl]-Benzonitrile ([11C]DASB) 285
Daniela Haeusler, Markus Mitterhauser and Wolfgang Wadsak

Chapter 29: Synthesis of [11C]Acetate 297
Filippo Lodi, Claudio Malizia and Stefano Boschi

Chapter 30: Synthesis of N-(2-[11C]Methoxybenzyl)-N-(4-Phenoxypyridin-3-yl)Acetamide ([11C]PBR28) 305
Qi-Huang Zheng, Min Wang and Bruce H. Mock

Part 3: Other Radiopharmaceuticals 313

Chapter 31: Synthesis of [13N]Ammonia ([13N]NH3) 315
Peter J. H. Scott

Chapter 32: Synthesis of [68Ga]Gallium DOTA-(TYR3)-Octreotide Acetate ([68Ga]DOTATOC) 321
Harald Eidherr, Friedrich Girschele, Markus Mitterhauser and Wolfgang Wadsak

Appendix 1: Supplier Information 335

Index 339

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Peter J. H. Scott is an Assistant Professor in the Department of Radiology at the University of Michigan Medical School. Dr. Scott edited Linker Strategies in Solid-phase Organic Synthesis (also from Wiley) and is the series editor for the Wiley Series on Solid Phase Organic Syntheses.

Brian G. Hockley is Radiopharmaceutical Quality Manager at the University of Michigan Medical School, where he works with Michael Kilbourn on radiopharmaceutical research and development. Mr. Hockley has co-authored several articles and a chapter in Linker Strategies in Solid-phase Organic Synthesis (also from Wiley).

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