ORG-21465

ORG-21465
Clinical data
Other names2β-(2,2-Dimethyl-4-morpholinyl)-3α-hydroxy-11,20-dioxo-5α-pregnan-21-yl methanesulfonate
Identifiers
IUPAC name
  • [2-[(2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-(2,2-dimethylmorpholin-4-yl)-3-hydroxy-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl]methanesulfonate
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H43NO7S
Molar mass525.70 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(OCC(=O)[C@H]5CC[C@@H]1[C@]5(C)CC(=O)[C@H]3[C@H]1CC[C@H]4C[C@H](O)[C@@H](N2CC(OCC2)(C)C)C[C@]34C)C
InChI
  • InChI=1S/C28H45NO7S/c1-26(2)16-29(10-11-35-26)21-13-27(3)17(12-22(21)30)6-7-18-19-8-9-20(24(32)15-36-37(5,33)34)28(19,4)14-23(31)25(18)27/h17-22,25,30H,6-16H2,1-5H3/t17-,18-,19-,20+,21-,22-,25+,27-,28-/m0/s1
  • Key:SUCBEQDWLIEMEH-JDOQEMNXSA-N
  (verify)

ORG-21465 is a synthetic neuroactive steroid, with sedative effects resulting from its action as a GABAA receptor positive allosteric modulator. It is similar to related drugs such as ORG-20599, and was similarly developed as an improved alternative to other sedative steroids such as althesin and allopregnanolone, which despite its superior properties in some respects has not proved to offer enough advantages to be accepted into clinical use.[1][2]

Chemistry

See also

References

  1. Sear JW (October 1997). "ORG 21465, a new water-soluble steroid hypnotic: more of the same or something different?". British Journal of Anaesthesia. 79 (4): 417–9. doi:10.1093/bja/79.4.417. PMID 9389254.
  2. Vanlersberghe C, Camu F (2008). "Etomidate and other non-barbiturates". Handbook of Experimental Pharmacology. 182 (182): 267–82. doi:10.1007/978-3-540-74806-9_13. ISBN 978-3-540-72813-9. PMID 18175096.
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