U46619

U46619

Names
IUPAC name (Z)-7-[(1S,4R,5R,6S)-5-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid
Identifiers
CAS Number	56985-40-1
ChEMBL	ChEMBL357834
IUPHAR/BPS	1888
Jmol interactive 3D	Image
PubChem	5311493
SMILES CCCCC[C@H](O)/C=C/[C@H]1[C@@H]2OC[C@@H](C2)[C@@H]1C/C=C\CCCC(O)=O
Properties
Chemical formula	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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Infobox references

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.^[2] It potently stimulates TP receptor-mediated, but not other prostaglandin receptor-mediated responses in various in vitro preparations.^[3] and exhibits many properties similar to thromboxane A₂, including shape change and aggregation of platelets ^[4] and smooth muscle contraction. U46619 is a vasoconstrictor that mimics the hydroosmotic effect of vasopressin.^[5]

References

1. Bundy, G. L. (1975). "Synthesis of prostaglandin endoperoxide analogs". Tetrahedron Letters 24 (24): 1957–1960. doi:10.1016/S0040-4039(00)72333-1.
2. "U 46619". www.tocris.com.
3. "U 46619". www.tocris.com.
4. 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: 789–797. doi:10.1016/0090-6980(87)90107-9.
5. 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.