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 ;
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 ;
	(verify)

Minaxolone (CCI-12923) is a neuroactive steroid which was developed as a general anesthetic but was withdrawn before registration due to toxicity seen with long-term administration in rats, and hence was never marketed.^[1]^[2]^[3] It is a positive allosteric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

References

^ C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1358–. ISBN 978-0-412-46630-4.
^ J. G. Bovill; Michael B. Howie (1999). Clinical Pharmacology for Anaesthetists. W.B. Saunders. ISBN 978-0-7020-2167-1.
^ 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.
^ ^a ^b Giovanni Biggio; Robert H. Purdy (2001). 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". Br J Anaesth. 92 (5): 704–11. CiteSeerX 10.1.1.519.3591. doi:10.1093/bja/aeh125. PMID 15033889.

[GanellinTriggle1996-1] C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1358–. ISBN 978-0-412-46630-4.

[BovillHowie1999-2] J. G. Bovill; Michael B. Howie (1999). Clinical Pharmacology for Anaesthetists. W.B. Saunders. ISBN 978-0-7020-2167-1.

[HemmingsHopkins2006-3] 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.

[BiggioPurdy2001-4] Giovanni Biggio; Robert H. Purdy (2001). Neurosteroids and Brain Function. Academic Press. pp. 196–. ISBN 978-0-12-366846-2.

[pmid15033889-5] 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.

[1]

[2]

[3]

[4]

[5]

Minaxolone

Chemistry

See also

References