{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = (5''R'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-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 | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category= | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_BR = C1 | legal_BR_comment = <ref>{{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}}</ref> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration = }}
'''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'''),<ref>{{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–}}</ref><ref name="Kar2005">{{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–}}</ref><ref name="Publishing2013">{{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–}}</ref> 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.<ref name="IISaidman2013">{{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–}}</ref> It was introduced in 1957,<ref name="Publishing2013" /> 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.<ref name="Dorfman2013">{{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–}}</ref>
==Chemistry== {{See also|List of neurosteroids}}
Related compounds include alfadolone, alfaxolone, dihydrodeoxycorticosterone, ganaxolone, minaxolone, pregnanolone, and renanolone.
==References== {{Reflist}}
{{General anesthetics}} {{GABAA receptor positive modulators}}
Category:5β-Pregnanes Category:Primary alcohols Category:Diketones Category:GABAA receptor positive allosteric modulators Category:General anesthetics Category:Neurosteroids