ORG-2058

ORG-2058
Clinical data
Other names16α-Ethyl-21-hydroxy-19-norprogesterone; 16α-Ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione
Identifiers
  • (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
UNII
ChEMBL
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
3D model (JSmol)
  • 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=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

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

See also

References

  1. ↑ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2350. ISBN 978-3-527-30247-5.
  2. 1 2 Fleischmann G, Beato M (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 (August 1985). "Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties". Journal of Steroid Biochemistry. 23 (2): 165–168. doi:10.1016/0022-4731(85)90232-8. PMID 3928974.
  4. ↑ Thompson EB, Lippman ME (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.