ORG-2058

{{short description|Chemical compound}}

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| IUPAC_name = (8R,9S,10R,13S,14S,16R,17S)-16-ethyl-17-(2-hydroxyacetyl)-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one

| image = ORG-2058.svg

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| CAS_number = 24320-06-7

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| PubChem = 119086

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| ChemSpiderID = 106407

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| ChEMBL = 2311103

| synonyms = 16α-Ethyl-21-hydroxy-19-norprogesterone; 16α-Ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione

| C=22 | H=32 | O=3

| SMILES = CC[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]2([C@H]1C(=O)CO)C

| StdInChI_Ref =

| StdInChI = 1S/C22H32O3/c1-3-13-11-19-18-6-4-14-10-15(24)5-7-16(14)17(18)8-9-22(19,2)21(13)20(25)12-23/h10,13,16-19,21,23H,3-9,11-12H2,1-2H3/t13-,16+,17-,18-,19+,21-,22+/m1/s1

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| StdInChIKey = IJLXLZGJDSJGIQ-BILPMHSYSA-N

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ORG-2058, also known as 16α-ethyl-21-hydroxy-19-norprogesterone, is a progestin of the 19-norprogesterone group which was never marketed.{{cite book| vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=zmpqAAAAMAAJ|year=2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=2350}}{{cite journal| vauthors = Fleischmann G, Beato M |title=Characterization of the progesterone receptor of rabbit uterus with the synthetic progestin 16α-ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione|journal=Biochimica et Biophysica Acta (BBA) - General Subjects|volume=540|issue=3|year=1978|pages=500–517|issn=0304-4165|doi=10.1016/0304-4165(78)90180-0}} It has high affinity for the progesterone receptor (775% of that of progesterone) and has been used in scientific research to study the role of the progesterone receptor in the body. The drug has no affinity for the estrogen receptor or the glucocorticoid receptor (less than 0.2% of the affinities of estradiol and dexamethasone, respectively){{cite journal | vauthors = Bergink EW, Loonen PB, Kloosterboer HJ | title = Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties | journal = Journal of Steroid Biochemistry | volume = 23 | issue = 2 | pages = 165–168 | date = August 1985 | pmid = 3928974 | doi = 10.1016/0022-4731(85)90232-8 }} and has slight affinity for the mineralocorticoid receptor, but less than that of progesterone.{{cite book| vauthors = Thompson EB, Lippman ME |title=Steroid receptors and the management of cancer|url=https://books.google.com/books?id=k8xrAAAAMAAJ|year=1979|publisher=CRC Press|isbn=978-0-8493-5477-9|quote=Org 2058 competed slightly, but less than progesterone, for mineralocorticoid binding.}}