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RU-28362

From Wikipedia, the free encyclopedia
RU-28362
Molecular structure of RU28362
Names
IUPAC name
11β,17β-Dihydroxy-6-methyl-17α-(prop-1-yn-1-yl)androsta-1,4,6-trien-3-one
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,10S,11aS)-1,10-Dihydroxy-5,9a,11a-trimethyl-1-(prop-1-yn-1-yl)-1,2,3,3a,3b,9a,9b,10,11,11a-decahydro-7H-cyclopenta[a]phenanthren-7-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C23H28O3/c1-5-8-23(26)10-7-17-16-11-14(2)18-12-15(24)6-9-21(18,3)20(16)19(25)13-22(17,23)4/h6,9,11-12,16-17,19-20,25-26H,7,10,13H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-/m0/s1
    Key: UFZKDKHLKHEFGA-ZFTCBNFESA-N
  • InChI=1S/C23H28O3/c1-5-8-23(26)10-7-17-16-11-14(2)18-12-15(24)6-9-21(18,3)20(16)19(25)13-22(17,23)4/h6,9,11-12,16-17,19-20,25-26H,7,10,13H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-/m0/s1
    Key: UFZKDKHLKHEFGA-ZFTCBNFESA-N
  • InChI=1/C23H28O3/c1-5-8-23(26)10-7-17-16-11-14(2)18-12-15(24)6-9-21(18,3)20(16)19(25)13-22(17,23)4/h6,9,11-12,16-17,19-20,25-26H,7,10,13H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-/m0/s1
    Key: UFZKDKHLKHEFGA-ZFTCBNFEBV
  • CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2C=C(C4=CC(=O)C=C[C@]34C)C)O)C)O
Properties
C23H28O3
Molar mass352.474 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

RU-28362 is asyntheticandrostaneglucocorticoid that was developed byRoussel Uclaf. It is aselectiveagonist of theglucocorticoid receptor (corticoid type II receptor), but not of themineralocorticoid receptor (corticoid type I receptor).[1][2]

A similar compound isdexamethasone that also selectively binds to the glucocorticoid receptor with high affinity. This is in contrast to the natural steroid hormonescortisol orcorticosterone, which bind to both of thecorticosteroid receptors, though they bind to the mineralocorticoid receptor with greater affinity.[3]

See also

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References

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  1. ^Woolley C, Gould E, Sakai R, Spencer R, McEwen B (1991). "Effects of aldosterone or RU28362 treatment on adrenalectomy-induced cell death in the dentate gyrus of the adult rat".Brain Res.554 (1–2):312–5.doi:10.1016/0006-8993(91)90207-C.PMID 1933312.S2CID 40166720.
  2. ^Wong D, Lesage A, Siddall B, Funder J (1992)."Glucocorticoid regulation of phenylethanolamine N-methyltransferasein vivo".FASEB J.6 (14):3310–5.doi:10.1096/fasebj.6.14.1426768.PMID 1426768.S2CID 23761885.
  3. ^Arriza, JL; Simerly, RB; Swanson, LW; Evans, RM (November 1988). "The neuronal mineralocorticoid receptor as a mediator of glucocorticoid response".Neuron.1 (9):887–900.doi:10.1016/0896-6273(88)90136-5.PMID 2856104.S2CID 41065703.


GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others


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