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.