Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol.
The beta-adrenergic agonist 1 (zilpaterol) is used as production enhancer in cattle. Binding experiments of separated enantiomers on recombinant human beta(2)-adrenergic and mu-opioid receptors and functional studies showed that the (-)-1 enantiomer accounts for essentially all the beta(2)-adrenergic agonist activity and that it exhibits less affinity toward the mu-opioid receptor than (+)-1, which is a mu-opioid receptor antagonist. X-ray crystallography revealed the absolute configuration of (-)-1 to be 6R,7R.
Kern
Christopher
C
Intervet Innovation GmbH, Zur Propstei, D 55270 Schwabenheim, Germany.
Meyer
Thorsten
T
Droux
Serge
S
Schollmeyer
Dieter
D
Miculka
Christian
C
D058666:Adrenergic beta-2 Receptor Agonists; D000318:Adrenergic beta-Agonists / Q000138:chemical synthesis* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D006801:Humans; D011994:Recombinant Proteins / Q000819:agonists; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*
D058666:Adrenergic beta-2 Receptor Agonists; D000318:Adrenergic beta-Agonists; D011994:Recombinant Proteins; D014297:Trimethylsilyl Compounds; C475840:Zilpaterol