词条 | Hydroxydione |
释义 |
| 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 | tradename = Viadril, Predion, Presuren | CAS_number = 303-01-5 | ATC_prefix = None | ATC_suffix = | PubChem = 257630 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB08956 | ChemSpiderID = 226020 | C=21 | H=32 | O=3 | molecular_weight = 332.477 g/mol | 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 = | pregnancy_US = | pregnancy_category= | legal_AU = | legal_CA = | legal_UK = | legal_US = | 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),[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] Chemistry{{See also|List of neurosteroids}}Related compounds include alfadolone, alfaxolone, dihydrodeoxycorticosterone, ganaxolone, minaxolone, pregnanolone, and renanolone. References1. ^{{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–}} {{General anesthetics}}{{GABAA receptor positive modulators}}2. ^{{cite book|author=Ashutosh Kar|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–}} 3. ^1 {{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–}} 4. ^{{cite book|author1=Edmond I Eger II|author2=Lawrence Saidman|author3=Rod Westhorpe|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–}} 5. ^{{cite book|author=Ralph I. Dorfman|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–}} 6 : 5β-Pregnanes|Alcohols|Diketones|GABAA receptor positive allosteric modulators|General anesthetics|Neurosteroids |
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