Cyclopregnol

Cyclopregnol (INN), also known as neurosterone, as well as 6β-hydroxy-3:5-cyclopregnan-20-one, is a synthetic pregnane steroid which was developed in the 1950s as a "psychotropic agent" for the treatment of mental disorders but was never marketed.[1][2][3][4] Although an initial small clinical study found effectiveness,[3] a subsequent, larger and more rigorous study found that cyclopregnol was no more effective than placebo and was clearly inferior to chlorpromazine.[4][5]

Cyclopregnol

Clinical data
Other names	Neurosterone; 6β-Hydroxy-3:5-cyclopregnan-20-one
Identifiers
CAS Number	465-53-2
PubChem CID	12308830
ChemSpider	35517184
UNII	Z06494074X
Chemical and physical data
Formula	C21H32O2
Molar mass	316.485 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@H]([C@]45[C@@]3(CC[C@H]4C5)C)O)C
InChI InChI=1S/C21H32O2/c1-12(22)15-4-5-16-14-10-18(23)21-11-13(21)6-9-20(21,3)17(14)7-8-19(15,16)2/h13-18,23H,4-11H2,1-3H3/t13-,14-,15+,16-,17-,18+,19+,20+,21+/m0/s1 Key:UGIARLNNAPRCPF-HUPPADNKSA-N

See also

• List of neurosteroids

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 646–. ISBN 978-1-4757-2085-3.
2. Patel, D. K.; Petrow, V.; Stuart-Webb, I. A. (1957). "133. 6β-Hydroxy-3 : 5-cyclopregnan-20-one and some related compounds". J. Chem. Soc. 0 (0): 665–668. doi:10.1039/JR9570000665. ISSN 0368-1769.
3. HARDWICK SW, PEARSE JJ, PETROW V (1957). "6 beta-Hydroxy-3:5-cyclopregnan-20-one in mental states". J Ment Sci. 103 (433): 835–9. doi:10.1192/bjp.103.433.835. PMID 13481595.
4. Loranger AW (1968). "Treatment of acute mental disorders with an adrenal steroid". Br J Psychiatry. 114 (512): 843–4. doi:10.1192/bjp.114.512.843. PMID 4874165.
5. Annual Reports in Medicinal Chemistry. Academic Press. 1969. pp. 3–. ISBN 978-0-08-058348-8.