The non-xanthine heterocyclic compound SCH 58261 is a new potent and selective A2a adenosine receptor antagonist

J Pharmacol Exp Ther. 1996 Feb;276(2):398-404.

Abstract

We have characterized the in vitro pharmacological profile of the new potent and selective A2a adenosine receptor antagonist SCH 58261 [7-(2-phenylethyl)-5-amino-2-(2-furyl)-pyrazolo-[4,3-e]-1,2, 4-triazolo[1,5-c]pyrimidine]. In binding studies on rat and bovine brain tissues, SCH 58261 showed affinity in the low nanomolar range at A2a adenosine striatal receptors and good A2a adenosine vs. A1 adenosine selectivity (about 50- to 100-fold in rat and bovine brain, respectively). SCH 58261 did not show affinity for either the A3 adenosine receptor or other receptors at concentrations up to 1 microM. Saturation experiments on rat A1 and A2a adenosine receptors indicated the competitive nature of the antagonism. SCH 58261 antagonized competitively the effects induced by the A2a adenosine-selective agonist CGS 21680 (2-[4-(2-carboxyethyl)-phenethyl-amino]-5'-N- ethylcarboxamidoadenosine) in two functional assays, such as inhibition of rabbit platelet aggregation and porcine coronary artery relaxation. Specifically, the compound showed pA2 values of 7.9 and 9.5, respectively. SCH 58261 (300 nM) failed to antagonize 5'-N-ethylcarboxamidoadenosine-induced vasorelaxation in the isolated guinea pig aorta, a response mediated by A2b adenosine receptors. Likewise, at the same concentration, the compound weakly inhibited the A1 adenosine-mediated negative chronotropic effect induced by 2-chloro-N6-cyclopentyladenosine in the isolated rat atria. These data show that SCH 58261 is a potent and selective non-xanthine A2a adenosine antagonist which has competitive properties in biological responses mediated by this receptor subtype. The compound is of interest for investigating the biological role of A2a adenosine receptors and deserves further attention to clarify the therapeutic potential of A2a antagonists.

MeSH terms

  • Animals
  • Cattle
  • Coronary Vessels / drug effects
  • Coronary Vessels / physiology
  • Guinea Pigs
  • In Vitro Techniques
  • Male
  • Myocardial Contraction / drug effects
  • Platelet Aggregation / drug effects
  • Platelet Aggregation Inhibitors / pharmacology
  • Purinergic P1 Receptor Antagonists*
  • Pyrimidines / metabolism
  • Pyrimidines / pharmacology*
  • Rabbits
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Purinergic P1 / metabolism
  • Swine
  • Triazoles / metabolism
  • Triazoles / pharmacology*

Substances

  • 5-amino-7-(2-phenylethyl)-2-(2-furyl)pyrazolo(4,3-e)-1,2,4-triazolo(1,5-c)pyrimidine
  • Platelet Aggregation Inhibitors
  • Purinergic P1 Receptor Antagonists
  • Pyrimidines
  • Receptors, Purinergic P1
  • Triazoles