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Article << Previous     |     Next >>   Contents Vol 59(1)

Synthesis and Radiolabelling of Ipratropium and Tiotropium for Use as PET Ligands in the Study of Inhaled Drug Deposition

Fatiah Issa A, Michael Kassiou A B C, Hak-Kim Chan D, Malcolm D. McLeod A E

A School of Chemistry, F11, University of Sydney, Sydney NSW 2006, Australia.
B Department of PET and Nuclear Medicine, Royal Prince Alfred Hospital, Camperdown NSW 2050, Australia.
C Department of Pharmacology, D06, University of Sydney, Sydney NSW 2006, Australia.
D Faculty of Pharmacy, A15, University of Sydney, Sydney NSW 2006, Australia.
E Corresponding author. Email: m.mcleod@chem.usyd.edu.au
 
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Abstract

Ipratropium bromide [(1R,3r,5S,8r,2′RS)-3-(3′-hydroxy-2′-phenylpropionyloxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium bromide] and tiotropium bromide [(1R,2R,4S,5S,7s)-7-[2′-hydroxy-2′,2′-di(thiophen-2′′-yl)acetoxy]-9,9-dimethyl-9-aza-3-oxatricyclo[3.3.1.02,4]nonan-9-ium bromide] are inhaled drugs used in the treatment of chronic obstructive pulmonary disease (COPD) and asthma. Tertiary amine precursors have been synthesized and radiolabelled with carbon-11 by N-alkylation with [11C]CH3I. The [11C]ipratropium and [11C]tiotropium positron emission tomography (PET) ligands are obtained with high radiochemical purity, in 0.3 and 0.5% non-decay corrected yields based on [11C]CO2 at end-of-synthesis and specific activities of 11 and 18 GBq μmol-1, respectively, calculated at end-of-synthesis. These PET radioligands can be used in the study of inhaled drug deposition.

   
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