Minaxolone

Minaxolone (CCI-12923) is a neuroactive steroid which was developed as a general anesthetic but was withdrawn before registration due to toxicity seen with long-term administration in rats, and hence was never marketed.[1][2][3] It is a positive allosteric modulator of the GABAA receptor,[4] as well as, less potently, a positive allosteric modulator of the glycine receptor.[4][5]

Minaxolone
Clinical data
Other names11α-(Dimethylamino)-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one
ATC code
  • none
Identifiers
IUPAC name
  • 1-[(1S,2S,4S,5S,7S,10S,11S,14S,15S,17R)-17-(dimethylamino)-4-ethoxy-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC25H43NO3
Molar mass405.623 g·mol−1
3D model (JSmol)
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
InChI
  • 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
 NY (what is this?)  (verify)

Chemistry
See also: List of neurosteroids

See also

References
  1. C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1358–. ISBN 978-0-412-46630-4.
  2. J. G. Bovill; Michael B. Howie (1999). Clinical Pharmacology for Anaesthetists. W.B. Saunders. ISBN 978-0-7020-2167-1.
  3. Hugh C. Hemmings; Philip M. Hopkins (2006). Foundations of Anesthesia: Basic Sciences for Clinical Practice. Elsevier Health Sciences. pp. 305–. ISBN 978-0-323-03707-5.
  4. Giovanni Biggio; Robert H. Purdy (2001). 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". Br J Anaesth. 92 (5): 704–11. CiteSeerX 10.1.1.519.3591. doi:10.1093/bja/aeh125. PMID 15033889.


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