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Minaxolone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Minaxolone
Clinical data
Other names11α-(Dimethylamino)-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one
ATC code
  • none
Identifiers
  • 1-[(1S,2S,4S,5S,7S,10S,11S,14S,15S,17R)-17-(dimethylamino)-4-ethoxy-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC25H43NO3
Molar mass405.623 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 ☒N
  • Key:NCGLTZSBTFVVAW-KNXRZYMVSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Minaxolone (CCI-12923) is aneuroactive steroid which was developed as ageneral anesthetic but was withdrawn before registration due totoxicity seen with long-term administration in rats, and hence was never marketed.[1][2][3] It is apositive allosteric modulator of theGABAA receptor,[4] as well as, less potently, a positive allosteric modulator of theglycine receptor.[4][5]

Chemistry

[edit]
See also:List of neurosteroids

See also

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References

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  1. ^Ganellin CR, Triggle DJ (21 November 1996).Dictionary of Pharmacological Agents. CRC Press. pp. 1358–.ISBN 978-0-412-46630-4.
  2. ^Bovill JB, Howie MC, eds. (1999).Clinical Pharmacology for Anaesthetists. W.B. Saunders.doi:10.1016/B978-0-323-03707-5.50031-0.ISBN 978-0-7020-2167-1.
  3. ^Perouansky MA, Hemmings Jr HC (2006)."Intravenous anesthetic agents". In Hemmings HC, Hopkins PM (eds.).Foundations of Anesthesia: Basic Sciences for Clinical Practice. Elsevier Health Sciences. pp. 305–.ISBN 978-0-323-03707-5.
  4. ^abLambert JJ, Harney SC, Belelli D, Peters JA (2001)."Neurosteroid modulation of recombinant and synaptic GABAA receptor". In Biggio G, Purdy RH (eds.).Neurosteroids and Brain Function. Academic Press. pp. 196–.ISBN 978-0-12-366846-2.
  5. ^Weir CJ, Ling AT, Belelli D, Wildsmith JA, Peters JA, Lambert JJ (May 2004). "The interaction of anaesthetic steroids with recombinant glycine and GABAA receptors".British Journal of Anaesthesia.92 (5):704–711.CiteSeerX 10.1.1.519.3591.doi:10.1093/bja/aeh125.PMID 15033889.
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Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
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