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Chemical compound
Minaxolone
Other names 11α-(Dimethylamino)-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one
ATC code
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
Formula C 25 H 43 N O 3
Molar mass 405.623 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
N Y
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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general anesthetic but was withdrawn before registration due to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]
Chemistry
See also
References
^ Ganellin CR, Triggle DJ (21 November 1996).
Dictionary of Pharmacological Agents . CRC Press. pp. 1358–.
ISBN
978-0-412-46630-4 .
^ 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 .
^ 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 .
^
a
b Lambert 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 .
^ 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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