295,99 €
The thoroughly updated new edition of the authoritative reference in Radiopharmaceutical Sciences The second edition of Handbook of Radiopharmaceuticals is a comprehensive review of the field, presenting up-to-date coverage of central topics such as radionuclide production, synthetic methodology, radiopharmaceutical development and regulations, and a wide range of practical applications. A valuable reference work for those new to the Radiopharmaceutical Sciences and experienced professionals alike, this volume explores the latest concepts and issues involving both targeted diagnostic and therapeutic radiopharmaceuticals. Contributions from a team of experts from across sub-disciplines provide readers with an immersive examination of radiochemistry, nuclear medicine, molecular imaging, and more. Since the first edition of the Handbook was published, Nuclear Medicine and Radiopharmaceutical Sciences have undergone major changes. New radiopharmaceuticals for diagnosis and therapy have been approved by the FDA, the number of clinical PET and SPECT scans have increased significantly, and advances in Artificial Intelligence have dramatically improved research techniques. This fully revised edition reflects the current state of the field and features substantially updated and expanded content. New chapters cover topics including current Good Manufacturing Practice (cGMP), regulatory oversight, novel approaches to quality control--ensuring that readers are informed of the exciting developments of recent years. This important resource: * Features extensive new and revised content throughout * Covers key areas of application for diagnosis and therapy in oncology, neurology, and cardiology * Emphasizes the multidisciplinary nature of Radiopharmaceutical Sciences * Discusses how drug companies are using modern radiopharmaceutical imaging techniques to support drug discovery * Examines current and emerging applications of Positron Emission Tomography (PET) and Single Photon Emission Computed Tomography (SPECT) Edited by recognized experts in radiochemistry and PET imaging, Handbook of Radiopharmaceuticals: Radiochemistry and Applications, 2 nd Edition is an indispensable reference for post-doctoral fellows, research scientists, and professionals in the pharmaceutical industry, and for academics, graduate students, and newcomers in the field of radiopharmaceuticals.
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Seitenzahl: 1493
Veröffentlichungsjahr: 2021
Second Edition
Edited by
MICHAEL R. KILBOURN
University of Michigan
Ann Arbor, USA
PETER J.H. SCOTT
University of Michigan
Ann Arbor, USA
This second edition first published 2021
© 2021 John Wiley & Sons Ltd.
Edition History
John Wiley & Sons, Ltd. (1e, 2003)
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The right of Michael R. Kilbourn and Peter J.H. Scott to be identified as the authors of the editorial material in this work has been asserted in accordance with law.
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Library of Congress Cataloging‐in‐Publication Data
Names: Kilbourn, Michael R., editor. | Scott, Peter J. H., editor.
Title: Handbook of radiopharmaceuticals : methodology and applications /
edited by Michael R. Kilbourn, University of Michigan and Peter J.H.
Scott, University of Michigan.
Description: Second edition. | Hoboken, NJ : Wiley, 2021. | Revised edition
of: Handbook of radiopharmaceuticals : radiochemistry and applications /
editors, Michael J. Welch, Carol S. Redvanly. c2003. | Includes
bibliographical references and index.
Identifiers: LCCN 2020025975 (print) | LCCN 2020025976 (ebook) | ISBN
9781119500544 (cloth) | ISBN 9781119500551 (adobe pdf) | ISBN
9781119500568 (epub)
Subjects: LCSH: Radiopharmaceuticals–Handbooks, manuals, etc.
Classification: LCC RS431.R34 H36 2021 (print) | LCC RS431.R34 (ebook) |
DDC 615.8/42–dc23
LC record available at https://lccn.loc.gov/2020025975
LC ebook record available at https://lccn.loc.gov/2020025976
Cover Design: Wiley
Cover Image: Radio logical image of human body organs, Creative Commons
Michael R. Kilbourn is an emeritus professor of radiology at the University of Michigan Medical School. He retired from the university after 25 years of directing and expanding the PET Cyclotron and Radiochemistry program, where he pursued research efforts directed at the design, development, and application of novel PET radiotracers for Parkinson's and Alzheimer's diseases.
Peter J.H. Scott is an associate professor of radiology and a member of the Interdepartmental Program in Medicinal Chemistry at the University of Michigan. He is director of the University of Michigan Positron Emission Tomography (PET) Center and runs a research group developing new radiochemistry methodology and novel PET radiotracers. His laboratory is funded by the US Department of Energy, the National Institutes of Health, and the Alzheimer's Association and has multiple collaborations with academic institutions and biotech and pharmaceutical companies all over the world. Professor Scott has edited four other books for Wiley, including two volumes of Radiochemical Syntheses.
Franklin I. Aigbirhio
Molecular Imaging Chemistry Laboratory, Wolfson Brain Imaging Centre, Department of Clinical Neurosciences
University of Cambridge, Cambridge Biomedical Campus
Cambridge, UK
Stephen J. Archibald
Positron Emission Tomography Research Centre, Department of Biomedical Sciences, Faculty of Health Sciences
University of Hull
Hull, UK
Nicolaas I. Bohnen
Department of Radiology
University of Michigan
Ann Arbor, MI, US
Department of Neurology
University of Michigan
Ann Arbor, MI, USA
Neurology Service and GRECC
VAAAHS
Ann Arbor, MI, USA
John P. Bois
Department of Cardiovascular Diseases
Mayo Clinic
Rochester, MN, USA
Guy Bormans
Laboratory for Radiopharmaceutical Research, Department of Pharmaceutical and Pharmacological Sciences
University of Leuven
Leuven, Belgium
Allen F. Brooks
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Laura Bruton
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Benjamin P. Burke
Positron Emission Tomography Research Centre, Department of Biomedical Sciences, Faculty of Health Sciences
University of Hull
Hull, UK
Elizabeth R. Butch
Department of Diagnostic Imaging
St. Jude Children's Research Hospital
Memphis, TN, USA
Dae Yoon Chi
Department of Chemistry
Sogang University
Seoul
Korea
Mara Clark
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Frederik Cleeren
Laboratory for Radiopharmaceutical Research, Department of Pharmaceutical and Pharmacological Sciences
University of Leuven
Leuven,
Belgium
David W. Dick
Department of Radiology
University of Iowa
Iowa City, IA, USA
Mehdi Djekidel
Nuclear Medicine and Molecular Imaging
Sidra Medicine
Qatar
David J. Donnelly
Bristol‐Myers Squibb Pharmaceutical Research and Development
Princeton, NJ, USA
Arkadij Elizarov
Trace‐Ability
Los Angeles, California
USA
Vanessa Gómez‐Vallejo
Radiochemistry and Nuclear Imaging Group
CIC biomaGUNE
San Sebastián,
Spain
Jeroen A.C.M. Goos
Department of Radiology
Memorial Sloan‐Kettering Cancer Center
New York, NY, USA
Robert J. Gropler
Mallinckrodt Institute of Radiology
Washington University School of Medicine,
St Louis, MO, USA
Jason P. Holland
Department of Chemistry
University of Zurich
Zurich,
Switzerland
Salma Jivan
,
Helen Wills Neuroscience Institute, University of California
Berkley, CA, USA
Steven Kealey
Molecular Imaging Chemistry Laboratory, Wolfson Brain Imaging Centre, Department of Clinical Neurosciences
University of Cambridge
Cambridge Biomedical Campus
Cambridge, UK
Outi Keinänen
Department of Chemistry, Hunter College
The City University of New York
New York, NY, USA
Michael R. Kilbourn
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Suzanne E. Lapi
Department of Radiology
University of Alabama at Birmingham
Birmingham, AL, USA;
Department of Chemistry
University of Alabama at Birmingham
Birmingham, AL, USA
Jason S. Lewis
,
Department of Radiology
Memorial Sloan‐Kettering Cancer Center
Birmingham, AL, USA;
Molecular Pharmacology Program and the Radiochemistry and Molecular Imaging Probes Core
Memorial Sloan Kettering Cancer Center
Birmingham, AL, USA;
Departments of Radiology and Pharmacology
Weill Cornell Medical College
New York, NY, USA
Jordi Llop
Radiochemistry and Nuclear Imaging Group
CIC biomaGUNE
San Sebastián
Spain
Fernando López‐Gallego
Heterogeneous Biocatalysis Laboratory
Instituto de Síntesis Química y Catálisis Homogénea (ISQCH‐CSIC), University of Zaragoza
Zaragoza
Spain;
ARAID, Aragon I+D foundation
Zaragoza
Spain
C. Shaun Loveless
Department of Radiology
University of Alabama at Birmingham
Birmingham, AL, USA;
Department of Chemistry
Washington University in St. Louis
St Louis, MO, USA
Robert H. Mach
Department of Radiology, Perelman School of Medicine
University of Pennsylvania
Philadelphia, PA, USA
Katarina J. Makaravage
Department of Chemistry
University of Michigan
Ann Arbor, MI, USA
Dionysia Papagiannopoulou
Department of Pharmaceutical Chemistry, School of Pharmacy
Aristotle University of Thessaloniki
Thessaloniki
Greece
Krishna R. Pulagam
Radiochemistry and Nuclear Imaging Group
CIC biomaGUNE
San Sebastián
Spain
Sean W. Reilly
Department of Radiology, Perelman School of Medicine
University of Pennsylvania
Philadelphia, PA, USA
Luka Rejc
Radiochemistry and Nuclear Imaging Group
CIC biomaGUNE
San Sebastián
Spain;
Faculty of Chemistry and Chemical Technology,
University of Ljubljana
Ljubljana
Slovenia
Melissa E. Rodnick
,
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Thomas J. Ruth
TRIUMF and BC Cancer Research Centre
Vancouver, British Columbia,
Canada
Melanie S. Sanford
Department of Chemistry
University of Michigan
Ann Arbor, MI, USA
Peter J.H. Scott
Department of Radiology
University of Michigan
Ann Arbor, Michigan
USA
Selena M. Sephton
Molecular Imaging Chemistry Laboratory, Wolfson Brain Imaging Centre, Department of Clinical Neurosciences
University of Cambridge
Cambridge Biomedical Campus
Cambridge, UK
Barry L. Shulkin
Department of Diagnostic Imaging
St. Jude Children's Research Hospital
Memphis, TN, USA
Scott E. Snyder
Department of Diagnostic Imaging
St. Jude Children's Research Hospital
Memphis, TN, USA
Alexandra R. Sowa Dumond
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Stephen Thompson
Molecular Imaging Chemistry Laboratory, Wolfson Brain Imaging Centre, Department of Clinical Neurosciences
University of Cambridge
Cambridge Biomedical Campus
Cambridge, UK
Alfons Verbruggen
Laboratory for Radiopharmaceutical Research, Department of Pharmaceutical and Pharmacological Sciences
University of Leuven
Leuven, Belgium
Koen Vermeulen
Laboratory for Radiopharmaceutical Research, Department of Pharmaceutical and Pharmacological Sciences
University of Leuven
Leuven, Belgium
Jay Wright
Department of Radiology
University of Michigan
Ann Arbor, MI, USA
Brian M. Zeglis
Department of Radiology
Memorial Sloan‐Kettering Cancer Center
New York, NY, USA;
Department of Chemistry, Hunter College
The City University of New York
New York, NY, USA;
PhD program in chemistry
Graduate Center of the City University of New York,
New York, NY, USA;
Departments of Radiology and Pharmacology
Weill Cornell Medical College
New York, NY, USA
When Mike Welch and Carol Redvanly edited the first edition of the Handbook of Radiopharmaceuticals in 2003, the field of radiopharmaceutical sciences was undergoing a number of important changes. [18F]Fludeoxyglucose ([18F]FDG) had been recently approved by the US Food and Drug Administration (FDA), and reimbursement coverage was in place from the US Centers for Medicare and Medicaid Services. This was creating a burgeoning market for commercial production and distribution of [18F]FDG, which in turn drove innovation in both radiopharmaceutical manufacture and clinical scanner technology. At the same time, increasing numbers of radiochemistry facilities were stimulating the development of many different radiopharmaceuticals for research applications.
This innovation and research have continued over the intervening years, and as we complete this new edition at the start of the Roaring Twenties, we have been reflecting that it is another exciting and transformative time in the fields of nuclear medicine and radiopharmaceutical sciences! New radiopharmaceuticals continue to be approved by the FDA, including PET radiotracers for brain and cancer imaging and theranostics for cancer treatment. These radiopharmaceuticals are transforming the lives of the patients we diagnose and treat in our clinicals every day. Coupled with lobbying efforts by the Society of Nuclear Medicine and Molecular Imaging (SNMMI) and others to inform reimbursement policy, significant efforts by industrial partners to develop the radiochemistry and PET imaging suites of the future, initiatives by academic colleagues to standardize the nomenclature of our science,1 and the expected impact of artificial intelligence on our discipline, nuclear medicine has been invigorated and is transforming from a research technique into a powerful standard of care.
This growth in nuclear medicine is apparent in day‐to‐day operations around the world. In an established market like the United States, over 1.5 million clinical PET scans currently occur, and yet we have been impressed to see the number of clinical PET scans taking place at the University of Michigan double between 2014 and 2019. There is also substantial growth occurring in developing markets, and at the 2019 International Symposium of Radiopharmaceutical Sciences (ISRS) that took place in Beijing, it was remarked that a new PET scanner is being installed in China every two weeks! The concomitant growth in the use of radiotherapeutics means that innovation in the radiopharmaceutical sciences to meet these new demands is as important today as when the first edition of the Handbook was published.
We were both attracted to the fields of nuclear medicine and radiopharmaceutical sciences early in our careers for a number of reasons. First, radiopharmaceutical sciences is an exciting application of basic science with immediate impact on patient care; second, the translational aspect of the research is appealing; and finally, we thoroughly enjoy the diverse and multidisciplinary nature of the work. Our field exists at the intersection of medicine, biology, chemistry, physics, and engineering, and, with the exception of Antarctica, research applications and clinical uses of nuclear medicine are occurring on every continent.
The articles in the new edition of the Handbook demonstrate that the field of radiopharmaceutical sciences remains as multidisciplinary as ever. We have tried to keep this new edition faithful to the format of the original and asked authors to provide knowledge updates in their various sub‐disciplines (radionuclide production, radiochemistry, applications of radiopharmaceuticals) that have occurred since the first edition was published. However, the evolution of the radiopharmaceutical sciences since that time, particularly in regards to current Good Manufacturing Practice (cGMP), regulatory oversight, and novel approaches to quality control, have necessitated the addition of new chapters in these areas.
We look forward to how our field continues to develop in the next 20 years, as we witness new technology and applications in the radiopharmaceutical sciences that might find their way into a future edition of the Handbook and continue the legacy of Mike Welch and the other visionaries who started our field.
Michael R. Kilbourn
Peter J.H. Scott
June 2020
Ann Arbor MI, USA
1
See Coenen et al.,
Nucl Med Biol
. 2017;55:v‐xi, doi: 10.1016/j.nucmedbio.2017.09.004.
The first edition of the Handbook of Radiopharmaceuticals was published near the start of the twenty‐first century. Dedicated by Michael J. Welch and Carol Redvanly to the memory of Alfred P. Wolf, that volume provided students and researchers with a comprehensive review of the field of radiochemistry and its growing importance in medicine.
This second edition of the Handbook is dedicated to the memories of Michael Welch and the many other notable scientists and physicians that the field has lost in recent years, many of whom served as mentors or colleagues of the contributing authors to this edition. The radiochemical sciences and medical imaging have grown tremendously just in the past two decades, and as we enter the third decade of the twenty‐first century, there is the expectation that the future holds untold important and impactful advances. In this edition of the Handbook, we have emphasized chapters that bring the reader up to date on the exciting developments of recent years. We thank the editorial team at John Wiley & Sons as well as all of the authors, the majority of whom are new contributors, for their valuable time and effort in bringing this new edition of the Handbook to reality.
Michael R. Kilbourn
Peter J.H. Scott
June 2020
Ann Arbor MI, USA
5‐HT1A
serotonin 1A receptor
ACh
acetylcholine
AChE
acetylcholinesterase
AcOH
acetic acid
ACPC
1‐aminocyclopentanecarboxylic acid
AD
Alzheimer’s disease
ADC
antibody drug conjugate
ADM
s‐adenosyl‐
L
‐methionine
AI
artificial intelligence
ALARA
as low as reasonably achievable
AMDP
aminomethylenediphosphonate
AMT
α‐Methyl‐
L
‐tryptophan
ATP
adenosine triphosphate
ATTR
amyloid transthyretin
BACE
beta‐secretase
BAT
brown adipose tissue
BBB
blood‐brain barrier
B
max
maximum concentration of target binding sites
BOx
benzoxazole
BP
binding potential
BP
British Pharmacopeia
Bq
becquerel
BTA
aryl‐benzothiazole
BZD
benzodiazepine
CAD
coronary artery disease
cAMP
cyclic adenosine monophosphate
CBF
cerebral blood flow
CBS
compton backscattered
[
11
C]ACHC
aminocyclohexanecarboxylic acid
[
11
C]DASB
[
11
C]3‐amino‐4‐(2‐dimethylaminomethylphenylsulfanyl)‐benzonitrile
[
11
C]DOPA
[
11
C dihydroxyphenylalanine
[
11
C]DTBZ
[
11
C]Dihydrotetrabenazine
[
11
C]HED
[
11
C]hydroxyephedrine
[
11
C]PiB
[
11
C]Pittsburgh compound B (PIB ([N‐methyl‐
11
C]6‐Me‐BTA‐1)
CFR
Code of Federal Regulations
cGMP
current Good Manufacturing Practice
Ci
curie
ClogD
calculated distribution coefficient at pH 7.4
ClogP
calculated partition coefficient
CMC
chemistry, manufacturing, and controls
CMO
contract manufacturing organization
CNS
central nervous system
COMT
catecholamine O‐methyl transferase
CSF
cerebrospinal fluid
CT
computed tomography
CTA
clinical trial application
CV
cardiovascular
CXCR4
CXC‐chemokine receptor‐4
Da
daltons
DAT
dopamine transporter
DBU
1,8‐diazabicyclo[5.4.0]undec‐7‐ene
DDD
drug discovery and development
DIPE
di‐isopropyl ether
DMA
N,N
‐dimethylacetamide
DMF
N,N
‐dimethylformamide
DMF
drug master file
DMSO
dimethyl sulfoxide
DNA
deoxyribose nucleic acid
DOTA
1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid
DPA
dipicolylamine
DPzA
dipyrazolylamine
Dx
dextran
EANM
European Association of Nuclear Medicine
EC
electron capture
ECD
[
99m
Tc]ethylcysteine dimer
eCTD
electronic common technical document
EGFR
epidermal growth factor receptor
eLINACS
electron linear accelerators
EMA
European Medicines Agency
EOB
end‐of‐bombardment
EOS
end‐of‐synthesis
EP
European Pharmacopeia
EPI
epinephrine
EtOH
ethanol
EU
European Union
eV
electron volt
FA
fatty acid
FAAH
fatty acid amide hydrolase
[
18
F]FACBC
1‐amino‐3‐[
18
F]fluorocyclobutanecarboxylic acid (Fluciclovine, Axumin)
FDA
Food and Drug Administration
[
18
F]FDG
2‐deoxy‐2‐[
18
F]fluoro‐D‐glucose
FDH
formate dehydrogenase
[
18
F]FDOPA
6‐[
18
F]fluorodihydroxyphenylalanine
[
18
F]FES
[
18
F]fluoroestradiol
[
18
F]FET
2‐[
18
F]fluoroethyl)‐L‐tyrosine
[
18
F]FMISO
[
18
F]fluoromisonidazole
[
18
F]FMT
[
18
F]fluoromethyltyrosine
[
18
F]FPEB
[
18
F]3‐fluoro‐5‐(pyridin‐2‐ ylethynyl)benzonitrile
[
18
F]FSPG
(S‐4‐(3‐[
18
F]fluoropropyl)‐L‐glutamic acid
g
gram
GABA
gamma amino butyric acid
GC
gas chromatography
GIST
gastrointestinal stromal tumors
GLP
Good Laboratory Practice
GMP
Good Manufacturing Practice
HBED
N,N’
‐bis(2‐hydroxybenzyl)ethylendiamine‐
N,N’
‐diacetic acid
HDA
hexadecanoic acid
HER
human epidermal growth factor receptor
HEU
highly enriched uranium
HITS
high‐throughput screening
HIV/AIDS
human immunodeficiency virus/ acquired immunodeficiency syndrome
HMPAO
[
99m
Tc]hexamethylpropyleneamine oxime
HMR
heart mediastinal ratio
HPLC
high‐performance liquid chromatography
HSA
human serum albumin
HYNIC
hydrazinonicotinamide
IAEA
International Atomic Energy Agency
IB
investigators brochure
IBZM
iodobenzamide
ICH
International Council for Harmonization of Technical Requirements for Pharmaceuticals for Human Use
ID
injected dose
ID/g
injected dose per gram
IHC
immunohistochemistry
IMPD
investigational medicinal product dossier
IMZ
iomazenil
IND
investigational new drug
iNOS
inducible nitric oxide synthase
IVS
interventricular septum
K
d
equilibrium dissociation constant, affinity of ligand toward the target
LAF
laminar air flow
LET
linear energy transfer
LV
left ventricular
MAA
macroaggregated albumin
mAb
monoclonal antibody
MAO
monoamine oxidase
MCA
multi‐channel analyzer
MCNPX
Monte Carlo N‐Particle eXtended
MCP‐1
monocyte chemoattractant protein‐1
mCRPC
metastatic castration resistant prostate cancer
MDP
methylenediphosphonate
MeV
mega electron volt
MIBG
meta‐iodobenzylguanidine
Min
minutes
mmol
millimoles
MMP
matrix metalloproteinases
μmol
micromoles
MPI
myocardial perfusion imaging
MPI
myocardial perfusion reserve
MPTP
1‐methyl‐4‐phenyl‐1,2,3,6‐tetrahydropyridine
MRI
magnetic resonance imaging
MR2
muscarinic receptor 2
NA
natural abundance
NDA
new drug application
NE
norepinephrine
NET
neuroendocrine tumors
NK‐1
neurokinin‐1 receptor
nM
nanomolar
NOS
nitric oxide synthase
NOTA
1,4,7‐triazacyclononane‐triacetic acid
NPH
normal pressure hydrocephalus
NPs
nanoparticles
OCT
organic cation transporter
PBR
peripheral benzodiazepine receptor
PC
prostate cancer
PD
pharmacodynamics
PD‐L1
program death ligand 1 receptor
PET
positron emission tomography
Pgp
p‐glycoprotein
PHEN
phenylephrine
p.i.
post‐injection
PiB
Pittsburgh Compound B
PIDA
phenyliodonium diacetate
PK
pharmacokinetics
pKa
acid dissociation constant
PRRT
peptide receptor radionuclide therapy
PSMA
prostate‐specific membrane antigen
PTFE
polytetrafluoroethane
QA
quality assurance
QC
quality control
QMA
quaternary methyl ammonium
QNB
quiniclidinyl benzilate
R&D
research and development
RBA
relative binding affinity
RCY
radiochemical yield
RDRC
Radioactive Drug Research Committee
RGD
arginine‐glycine‐aspartic acid
RIT
radioimmunotherapy
RLD
reference listed drug
RLT
radioligand therapy
RV
right ventricular
SERT
serotonin transporter
S
N
Ar
nucleophilic aromatic substitution
SPE
solid phase extraction
SPECT
single photon emission computed tomography
SSRIs
selective serotonin reuptake inhibitors
SSTR‐2
somatostatin receptor 2
SUV
standardized uptake value
TACN
triazamacrocycle 1,4,7‐triazacyclononane
TAT
targeted alpha therapy
TATE
(Tyr
3
‐Thr
6
)‐octreotide
TBA
tetrabutylammonium
TBAF
tetra‐
n
‐butylammonium fluoride
TCEP
tris(2‐carboxyethyl)phosphine
Tf
triflate
THF
tetrahydrofuran
TNBC
triple‐negative breast cancer
TOC
(Tyr
3
)‐octreotide
TSPO
translocator protein, 18 kDa
TTR
transthyretin
USP
United States Pharmacopeia
UV
ultraviolet
VA
ventriculo‐atrial
VAChT
vesicular transporter for acetylcholine
VMAT2
vesicular monoamine transporter type 2
VP
ventriculo‐peritoneal
WHO
World Health Organization