A new class of nitric oxide-releasing derivatives of cetirizine; pharmacological profile in vascular and airway smooth muscle preparations

Br J Pharmacol. 2007 May;151(1):35-44. doi: 10.1038/sj.bjp.0707214. Epub 2007 Mar 12.

Abstract

Background and purpose: The pharmacological properties of compounds NCX 1512 and NCX 1514, synthesized by linking the histamine H1-receptor antagonist cetirizine to NO-releasing spacer groups, are reported. The aim was to establish if the compounds retained the antihistamine action of the parent compound, to assess their efficacy as NO donors and to test if they had broader antiallergic activity than cetirizine in the lung.

Experimental approach: Antihistamine activity of NCX 1512 and NCX 1514 was investigated in vitro in the guinea pig ileum, in tracheal rings (GPTR) and lung parenchymal strips (GPLP) of the guinea-pig. The NO-releasing capacity was investigated in vascular preparations; the isolated rabbit and guinea-pig aorta and guinea-pig pulmonary artery. Kinetics of NO release were assessed in a rat whole blood assay.

Key results: Both NCX 1512 and NCX 1514 retained activity as H1-receptor antagonists in the guinea pig ileum and airway preparations. The NO-releasing NCX compounds relaxed the rabbit aorta, an action prevented by the guanylyl cyclase inhibitor ODQ (10 microM). NCX 1512 and NCX 1514 did not relax the antigen (ovalbumin) pre-contracted GPTR, whereas the NO donors NCX 2057 and DEA-NONOate relaxed guinea-pig pre-contracted vascular and tracheal preparations. Cetirizine (1-100 microM) and NCX 1512 (1-100 microM) reduced the cumulative (0.01-100 microg ml(-1)) ovalbumin-induced constriction in GPTR, but had no significant effect in GPLP.

Conclusions and implications: NCX 1512 and NCX 1514 act as antihistamines and NO donors. However, there was no improved effect compared to cetirizine on antigen-induced constriction of the central and peripheral lung.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Butanes / pharmacology
  • Cetirizine / analogs & derivatives*
  • Cetirizine / pharmacology
  • Guinea Pigs
  • Histamine Antagonists / pharmacology
  • Ileum / drug effects
  • Ileum / physiology
  • In Vitro Techniques
  • Male
  • Muscle, Smooth / drug effects
  • Muscle, Smooth / physiology
  • Muscle, Smooth, Vascular / drug effects*
  • Muscle, Smooth, Vascular / physiology
  • Nitric Oxide / physiology
  • Nitric Oxide Donors / pharmacology*
  • Nitro Compounds / pharmacology
  • Rabbits
  • Trachea / drug effects*
  • Trachea / physiology
  • Vasodilation / drug effects

Substances

  • 3-((4-hydroxy-3-methoxyphenyl)-2-propenoic acid 4-nitrooxy)butyl ester
  • Butanes
  • Histamine Antagonists
  • NCX 1512
  • NCX 1514
  • Nitric Oxide Donors
  • Nitro Compounds
  • Nitric Oxide
  • Cetirizine