Hydroxydione

{{Short description|Chemical compound}}

{{Drugbox

| 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

| image = Hydroxydione.svg

| image_class = skin-invert-image

| tradename = Viadril, Predion, Presuren

| CAS_number = 303-01-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B7VFN88375

| ATC_prefix = None

| ATC_suffix =

| PubChem = 257630

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB08956

| ChemSpiderID = 226020

| C=21 | H=32 | O=3

| 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

| StdInChI = 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

| StdInChIKey = USPYDUPOCUYHQL-VEVMSBRDSA-N

| synonyms = 21-Hydroxy-5β-pregnane-3,20-dione

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| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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Hydroxydione, as hydroxydione sodium succinate ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}) (brand names Viadril, Predion, and Presuren),{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA531|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=531–}}{{cite book| vauthors = Kar A |title=Medicinal Chemistry|url=https://books.google.com/books?id=07g30rxCA0EC&pg=PA63|date=1 January 2005|publisher=New Age International|isbn=978-81-224-1565-0|pages=63–}}{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1863|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1863–}} 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.{{cite book| vauthors = Edmond II IE, Saidman L, Westhorpe R |title=The Wondrous Story of Anesthesia|url=https://books.google.com/books?id=H--3BAAAQBAJ&pg=PA632|date=14 September 2013|publisher=Springer Science & Business Media|isbn=978-1-4614-8441-7|pages=632–}} It was introduced in 1957, 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.{{cite book| vauthors = Dorfman RI |title=Steroidal Activity in Experimental Animals and Man|url=https://books.google.com/books?id=BbLfBAAAQBAJ&pg=PA447|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4832-7299-3|pages=447–}}