U46619
Names
Preferred IUPAC name
(5Z)-7-{(1R,4S,5S,6R)-6-[(1E,3S)-3-Hydroxyoct-1-en-1-yl]-2-oxabicyclo[2.2.1]heptan-5-yl}hept-5-enoic acid
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.164.944 Edit this at Wikidata
  • CCCCC[C@H](O)/C=C/[C@H]1[C@@H]2OC[C@@H](C2)[C@@H]1C/C=C\CCCC(O)=O
Properties
C21H34O4
Molar mass 350.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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U46619 is a stable synthetic analog of the endoperoxide prostaglandin PGH2 first prepared in 1975,[1] and acts as a thromboxane A2 (TP) receptor agonist. It potently stimulates TP receptor-mediated, but not other prostaglandin receptor-mediated responses in various in vitro preparations and exhibits many properties similar to thromboxane A2, including shape change and aggregation of platelets [2] and smooth muscle contraction. U46619 is a vasoconstrictor that mimics the hydroosmotic effect of vasopressin.[3]

References

  1. ^ Bundy, G. L. (1975). "Synthesis of prostaglandin endoperoxide analogs". Tetrahedron Letters. 16 (24): 1957–1960. doi:10.1016/S0040-4039(00)72333-1.
  2. ^ Liel, N.; Mais, D.E.; Halushka, P.V (1987). "Binding of a thromboxane A2/prostaglandin H2 agonist [3H]U46619 to washed human platelets". Prostaglandins. 33 (6): 789–797. doi:10.1016/0090-6980(87)90107-9. PMID 2959986.
  3. ^ Burch, Ronald M.; Halushka, Perry V. (1983). "Calcium-45 fluxes in isolated toad bladder epithelial cells: effects of agents which alter water or sodium transport". Journal of Pharmacology and Experimental Therapeutics. 224 (1): 108–17. PMID 6294273.


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