Minaxolone

Minaxolone
Clinical data
Other names	11α-(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	62571-87-3 ;
PubChem CID	71960;
IUPHAR/BPS	5478;
ChemSpider	64967 ;
UNII	737SKC73L0;
KEGG	D05041 ;
ChEMBL	ChEMBL2105209 ;
CompTox Dashboard (EPA)	DTXSID201024283 ;
Chemical and physical data
Formula	C25H43NO3
Molar mass	405.623 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:NCGLTZSBTFVVAW-KNXRZYMVSA-N ;
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Minaxolone (CCI-12923) is a neuroactive steroid which was developed as a general anesthetic but was withdrawn before registration due to toxicity seen with long-term administration in rats, and hence was never marketed.^[1]^[2]^[3] It is a positive allosteric modulator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 GABA_A receptor,^[4] as well as, less potently, a positive allosteric modulator of the glycine receptor.^[4]^[5]

Chemistry

^ 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.