Steric aspects of agonism and antagonism at beta-adrenoceptors: synthesis of and pharmacological experiments with the enantiomers of formoterol and their diastereomers

J TrofastBertil Waldeck


The enantiomers of formoterol (R;R and S;S) and their diastereomers (R;S and S;R) were synthesized and purified using a new procedure which required the preparation of the (R;R)- and (S;S)-forms of N-(1-phenylethyl)-N-(1-(p-methoxyphenyl)-2-propyl)-amine as important intermediates. The enantiomeric purity obtained was greater than 99.3%, usually greater than 99.7%. The four stereoisomers were examined with respect to their ability to interact in vitro with beta-adrenoceptors in tissues isolated from guinea pig. The effects measured were (1) relaxation of the tracheal smooth muscle (mostly beta 2), (2) depression of subtetanic contractions of the soleus muscle (beta 2), and (3) increase in the force of the papillary muscle of the left ventricle of the heart (beta 1). All enantiomers caused a concentration-dependent and complete relaxation of the tracheal smooth muscle which was inhibited by propranolol. The order of potency was (R;R) much greater than (R;S) = (S;R) greater than (S;S). There was a 1,000-fold difference in potency between the most and the least potent isomer. The presence of the (S;S)-isomer did not affect the activity of the (R;R)-isomer on the tracheal smooth muscle. Also on the skeletal and cardiac muscles (R;R...Continue Reading


May 1, 1976·The Journal of Pharmacy and Pharmacology·Bertil Waldeck
Sep 1, 1977·The Journal of Pharmacy and Pharmacology·Bertil Waldeck
Nov 1, 1989·Pharmacology & Toxicology·D F Smith
Oct 1, 1972·The Journal of Pharmacy and Pharmacology·R B BarlowJ D Pearson
Dec 1, 1968·European Journal of Pharmacology·Bertil Waldeck
Dec 1, 1983·The Journal of Pharmacy and Pharmacology·L H Johansson, H Persson
Feb 1, 1980·Acta Pharmacologica Et Toxicologica·E Holmberg, Bertil Waldeck


Oct 24, 1995·European Journal of Pharmacology·S LindbergT Runer
Jun 1, 1996·General Pharmacology·Bertil Waldeck
Jun 18, 2002·European Journal of Pharmacology·Bertil Waldeck
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Sep 19, 2002·British Journal of Clinical Pharmacology·Mei ZhangJohn P Shaw
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Oct 1, 1992·Pharmacology & Toxicology·A B JeppssonBertil Waldeck
Jan 1, 1995·Pharmacology & Toxicology·Bertil Waldeck
Jun 9, 2009·American Journal of Respiratory Cell and Molecular Biology·Philippe Delmotte, Michael J Sanderson
Oct 1, 1992·Journal of Clinical Pharmacology·J Caldwell
Sep 28, 2007·Bioorganic & Medicinal Chemistry Letters·Alan D BrownRob Webster
Jan 25, 2006·British Journal of Pharmacology·Peter MolenaarWilliam A Parsonage
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Jul 2, 2002·Pulmonary Pharmacology & Therapeutics·Dean A HandleyJohn Morley
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Feb 15, 2000·British Journal of Clinical Pharmacology·M ZhangJ P Shaw
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