minaxolone

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 447905095

| IUPAC_name = 1-[(1S,2S,4S,5S,7S,10S,11S,14S,15S,17R)-17-(dimethylamino)-4-ethoxy-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadecan-14-yl]ethan-1-one

| image = Minaxolone.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| 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

| 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Minaxolone (CCI-12923) is a neuroactive steroid which was developed as a general anesthetic but was withdrawn before registration due to toxicity seen with long-term administration in rats, and hence was never marketed.{{cite book| vauthors = Ganellin CR, Triggle DJ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–}}{{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 }}{{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–}} It is a positive allosteric modulator of the GABA_A receptor,{{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–}} as well as, less potently, a positive allosteric modulator of the glycine receptor.{{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 }}