{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447905095 | IUPAC_name = 1-[(1''S'',2''S'',4''S'',5''S'',7''S'',10''S'',11''S'',14''S'',15''S'',17''R'')-17-(dimethylamino)-4-ethoxy-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<sup>2,7</sup>.0<sup>11,15</sup>]heptadecan-14-yl]ethan-1-one | image = Minaxolone.svg | image_class = skin-invert-image
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
<!--Identifiers--> | IUPHAR_ligand = 5478 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 62571-87-3 | ATC_prefix = none | PubChem = 71960 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 2105209 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 737SKC73L0 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D05041 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 64967
<!--Chemical data--> | C=25 | H=43 | N=1 | O=3 | SMILES = CCO[C@H]1C[C@]2([C@@H](CC[C@@H]3[C@@H]2[C@@H](C[C@]4([C@H]3CC[C@@H]4C(=O)C)C)N(C)C)C[C@@H]1O)C | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C25H43NO3/c1-7-29-22-14-24(3)16(12-21(22)28)8-9-17-19-11-10-18(15(2)27)25(19,4)13-20(23(17)24)26(5)6/h16-23,28H,7-14H2,1-6H3/t16-,17-,18+,19-,20+,21-,22-,23+,24-,25+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = NCGLTZSBTFVVAW-KNXRZYMVSA-N | synonyms = 11α-(Dimethylamino)-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one }}
'''Minaxolone''' ('''CCI-12923''') is a neuroactive steroid which was developed as a general anesthetic but was withdrawn before registration due to toxicity seen with long-term administration in rats, and hence was never marketed.<ref name="GanellinTriggle1996">{{cite book| vauthors = Ganellin CR, Triggle DJ |title=Dictionary of Pharmacological Agents|url=https://books.google.com/books?id=A0THacd46ZsC&pg=PA1358|date=21 November 1996|publisher=CRC Press|isbn=978-0-412-46630-4|pages=1358–}}</ref><ref name="BovillHowie1999">{{cite book | veditors = Bovill JB, Howie MC |title=Clinical Pharmacology for Anaesthetists| url = https://books.google.com/books?id=sD1sAAAAMAAJ|year=1999|publisher=W.B. Saunders|isbn=978-0-7020-2167-1 | doi = 10.1016/B978-0-323-03707-5.50031-0 }}</ref><ref name="HemmingsHopkins2006">{{cite book | vauthors = Perouansky MA, Hemmings Jr HC | chapter = Intravenous anesthetic agents | veditors = Hemmings HC, Hopkins PM |title=Foundations of Anesthesia: Basic Sciences for Clinical Practice| chapter-url = https://books.google.com/books?id=xaXu1wHmENoC&pg=PA305|year=2006|publisher=Elsevier Health Sciences|isbn=978-0-323-03707-5|pages=305–}}</ref> It is a positive allosteric modulator of the GABA<sub>A</sub> receptor,<ref name="BiggioPurdy2001">{{cite book| vauthors = Lambert JJ, Harney SC, Belelli D, Peters JA | chapter = Neurosteroid modulation of recombinant and synaptic GABAA receptor| veditors = Biggio G, Purdy RH |title=Neurosteroids and Brain Function| chapter-url = https://books.google.com/books?id=13jQfYIkwhkC&pg=PA196|year=2001|publisher=Academic Press|isbn=978-0-12-366846-2|pages=196–}}</ref> as well as, less potently, a positive allosteric modulator of the glycine receptor.<ref name="BiggioPurdy2001" /><ref name="pmid15033889">{{cite journal | vauthors = Weir CJ, Ling AT, Belelli D, Wildsmith JA, Peters JA, Lambert JJ | title = The interaction of anaesthetic steroids with recombinant glycine and GABAA receptors | journal = British Journal of Anaesthesia | volume = 92 | issue = 5 | pages = 704–711 | date = May 2004 | pmid = 15033889 | doi = 10.1093/bja/aeh125 | citeseerx = 10.1.1.519.3591 }}</ref>
==Chemistry== {{See also|List of neurosteroids}}
== See also == * Alfadolone * Alfaxolone * Ganaxolone * Hydroxydione * Pregnanolone * Renanolone
== References == {{Reflist|2}}
{{General anesthetics}} {{GABAAR PAMs}} {{Glycinergics}}
Category:General anesthetics Category:Neurosteroids Category:Secondary alcohols Category:Ethers Category:Dimethylamino compounds Category:Ketones Category:GABAA receptor positive allosteric modulators Category:Glycine receptor agonists Category:Pregnanes Category:Ethoxy compounds
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