ORG-2058

ORG-2058, also known as 16α-ethyl-21-hydroxy-19-norprogesterone, is a progestin of the 19-norprogesterone group which was never marketed.[1][2] 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.[2] 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)[3] and has slight affinity for the mineralocorticoid receptor, but less than that of progesterone.[4]

ORG-2058
Clinical data
Other names16α-Ethyl-21-hydroxy-19-norprogesterone; 16α-Ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione
Identifiers
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
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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
  • Key:IJLXLZGJDSJGIQ-BILPMHSYSA-N

See also

References
  1. Martin Negwer; Hans-Georg Scharnow (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2350. ISBN 978-3-527-30247-5.
  2. Fleischmann, Gerhard; Beato, Miguel (1978). "Characterization of the progesterone receptor of rabbit uterus with the synthetic progestin 16α-ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione". Biochimica et Biophysica Acta (BBA) - General Subjects. 540 (3): 500–517. doi:10.1016/0304-4165(78)90180-0. ISSN 0304-4165.
  3. Bergink EW, Loonen PB, Kloosterboer HJ (1985). "Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties". J. Steroid Biochem. 23 (2): 165–8. doi:10.1016/0022-4731(85)90232-8. PMID 3928974.
  4. Edward Brad Thompson; Marc E. Lippman (1979). Steroid receptors and the management of cancer. CRC Press. ISBN 978-0-8493-5477-9. Org 2058 competed slightly, but less than progesterone, for mineralocorticoid binding.



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