Hydroxydione

Hydroxydione, as hydroxydione sodium succinate (INN, USAN, BAN) (brand names Viadril, Predion, and Presuren),[1][2][3] also known as 21-Hydroxy-5β-pregnane-3,20-dione, is a neuroactive steroid which was formerly used as a general anesthetic, but was discontinued due to incidence of thrombophlebitis in patients.[4] It was introduced in 1957,[3] and was the first neuroactive steroid general anesthetic to be introduced for clinical use, an event which was shortly preceded by the observation in 1954 of the sedative properties of progesterone in mice.[5]

Hydroxydione
Clinical data
Trade namesViadril, Predion, Presuren
Other names21-Hydroxy-5β-pregnane-3,20-dione
ATC code
  • None
Identifiers
IUPAC name
  • (5R,8R,9S,10S,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
Chemical and physical data
FormulaC21H32O3
Molar mass332.484 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)C
InChI
  • InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13,15-18,22H,3-12H2,1-2H3/t13-,15+,16+,17+,18-,20+,21+/m1/s1
  • Key:USPYDUPOCUYHQL-VEVMSBRDSA-N

Chemistry
See also: List of neurosteroids

Related compounds include alfadolone, alfaxolone, dihydrodeoxycorticosterone, ganaxolone, minaxolone, pregnanolone, and renanolone.

References
  1. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 531–. ISBN 978-3-88763-075-1.
  2. Kar A (1 January 2005). Medicinal Chemistry. New Age International. pp. 63–. ISBN 978-81-224-1565-0.
  3. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1863–. ISBN 978-0-8155-1856-3.
  4. Edmond II IE, Saidman L, Westhorpe R (14 September 2013). The Wondrous Story of Anesthesia. Springer Science & Business Media. pp. 632–. ISBN 978-1-4614-8441-7.
  5. Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 447–. ISBN 978-1-4832-7299-3.


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