Hydroxydione

Hydroxydione, as hydroxydione sodium succinate (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name) (brand names Viadril, Predion, and Presuren),^[2][3][4] 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.^[5] It was introduced in 1957,^[4] 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.^[6]

Hydroxydione

Clinical data
Trade names	Viadril, Predion, Presuren
Other names	21-Hydroxy-5β-pregnane-3,20-dione
ATC code	None
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1]
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	303-01-5
PubChem CID	257630
DrugBank	DB08956 Y
ChemSpider	226020
UNII	B7VFN88375
CompTox Dashboard (EPA)	DTXSID401027269
Chemical and physical data
Formula	C21H32O3
Molar mass	332.484 g·mol−1
3D model (JSmol)	Interactive image
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. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 531–. ISBN 978-3-88763-075-1.
3. Kar A (1 January 2005). Medicinal Chemistry. New Age International. pp. 63–. ISBN 978-81-224-1565-0.
4. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1863–. ISBN 978-0-8155-1856-3.
5. 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.
6. Dorfman RI (22 October 2013). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 447–. ISBN 978-1-4832-7299-3.