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U46619

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U46619
Names
Preferred IUPAC name (5Z)-7-{(1R,4S,5S,6R)-6--2-oxabicycloheptan-5-yl}hept-5-enoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.164.944 Edit this at Wikidata
IUPHAR/BPS
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • CCCCC(O)/C=C/12OC(C2)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 , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

U46619 is a stable synthetic analog of the endoperoxide prostaglandin PGH2 first prepared in 1975, 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 and smooth muscle contraction. U46619 is a vasoconstrictor that mimics the hydroosmotic effect of vasopressin.

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 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.
Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators


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