Effects of KW-3635, a novel dibenzoxepin derivative of a selective thromboxane A2 antagonist, on human, guinea pig and rat platelets

Jpn J Pharmacol. 1992 Jul;59(3):357-64. doi: 10.1254/jjp.59.357.

Abstract

We examined the binding of [3H]U-46619, a thromboxane A2 agonist, to human and guinea pig platelets and the binding of [3H]SQ 29,548, a thromboxane A2 antagonist, to human, rat and guinea pig platelets. KW-3635 (sodium (E)-11-[2-(5,6-dimethyl-1- benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-c arboxylate monohydrate) concentration-dependently inhibited the [3H]U-46619 binding to human and guinea pig platelets with inhibition constants of 1.2 nM and 2.7 nM, respectively. KW-3635 also potently inhibited the [3H]SQ 29,548 binding to human and guinea pig platelets with inhibition constants of 1.9 nM and 3.2 nM, respectively. In contrast, KW-3635 was less active against thromboxane A2/prostaglandin H2 receptors in rat platelets with an inhibition constant of 97 nM. KW-3635 at 10(-5) M did not antagonize various receptors including prostaglandin E2, prostaglandin I2 and neurotransmitters. In addition, 10(-5) M KW-3635 did not alter the prostaglandin D2-induced cAMP accumulation in EBTr cells. KW-3635 was inactive towards thromboxane synthase, cyclooxygenase and prostaglandin I2 synthase up to 10(-5) M. KW-3635 slightly inhibited 5-lipoxygenase with an IC50 value of 71 microM. These data indicate that KW-3635 is a potent and selective non-prostanoic thromboxane A2 antagonist, and it can recognize the species differences in thromboxane A2/prostaglandin H2 receptors.

MeSH terms

  • 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid
  • Animals
  • Benzimidazoles / pharmacology*
  • Benzoxepins / pharmacology*
  • Blood Platelets / drug effects*
  • Bridged Bicyclo Compounds, Heterocyclic
  • Dose-Response Relationship, Drug
  • Fatty Acids, Unsaturated
  • Guinea Pigs
  • Humans
  • Hydrazines / pharmacology
  • In Vitro Techniques
  • Kinetics
  • Prostaglandin Endoperoxides, Synthetic / pharmacology
  • Radioligand Assay
  • Rats
  • Receptors, Thromboxane / drug effects*
  • Species Specificity
  • Thromboxane A2 / antagonists & inhibitors*
  • Tritium
  • Vasoconstrictor Agents / pharmacology

Substances

  • Benzimidazoles
  • Benzoxepins
  • Bridged Bicyclo Compounds, Heterocyclic
  • Fatty Acids, Unsaturated
  • Hydrazines
  • Prostaglandin Endoperoxides, Synthetic
  • Receptors, Thromboxane
  • Vasoconstrictor Agents
  • Tritium
  • Thromboxane A2
  • 15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5,13-dienoic Acid
  • SQ 29548
  • KW 3635