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U46619

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(Redirected fromU-46619)
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.164.944Edit this at Wikidata
EC Number
  • 637-219-1
  • InChI=1S/C21H34O4/c1-2-3-6-9-17(22)12-13-19-18(16-14-20(19)25-15-16)10-7-4-5-8-11-21(23)24/h4,7,12-13,16-20,22H,2-3,5-6,8-11,14-15H2,1H3,(H,23,24)/b7-4-,13-12+/t16-,17+,18+,19-,20-/m1/s1
    Key: LQANGKSBLPMBTJ-BRSNVKEHSA-N
  • 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 mass350.49 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

U46619 is a stable syntheticanalog of the endoperoxideprostaglandin PGH2 first prepared in 1975,[1] and acts as athromboxane 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 tothromboxane A2, including shape change and aggregation ofplatelets[2] and smooth muscle contraction. U46619 is avasoconstrictor that mimics the hydroosmotic effect ofvasopressin.[3]

References

[edit]
  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.doi:10.1016/S0022-3565(25)33438-5.PMID 6294273.
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 synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others


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