Cetadiol

Cetadiol
Clinical data
Other names	Androst-5-ene-3β,16α-diol; 3β,16α-Dihydroxy-5-androstene
Routes of; administration	Oral
Identifiers
	IUPAC name (3S,8S,9S,10R,13R,14S,16R)-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol;
CAS Number	3642-89-5;
PubChem CID	19274;
ChemSpider	18185;
KEGG	C14631;
ChEBI	CHEBI:34452;
CompTox Dashboard (EPA)	DTXSID40957766 ;
Chemical and physical data
Formula	C19H30O2
Molar mass	290.447 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H](C2)O)CC=C4[C@@]3(CC[C@@H](C4)O)C;
	InChI InChI=1S/C19H30O2/c1-18-7-6-16-15(17(18)10-14(21)11-18)4-3-12-9-13(20)5-8-19(12,16)2/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14+,15+,16-,17-,18+,19-/m0/s1; Key:CVCDJRPXEWJAAY-UVSUZTNJSA-N;

Cetadiol, also known as androst-5-ene-3β,16α-diol, is a drug described as a "steroid tranquilizer" which was briefly investigated as a treatment for alcoholism in the 1950s.^[1]^[2]^[3]^[4]^[5] It is an androstane steroid and analogue of 5-androstenediol (androst-5-ene-3β,17β-diol) and 16α-hydroxy-DHEA (androst-5-ene-3β,16α-diol-17-one), but showed no androgenic or myotrophic activity in animal bioassays.^[4] The drug was reported in 1956 and studied until 1958.^[1]

Chemistry

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 86–. ISBN 978-1-4757-2085-3.
^ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1841. ISBN 978-3-527-30247-5.
^ Lemere F (April 1957). "New steroid hormone tranquilizing agent (cetadiol)". The American Journal of Psychiatry. 113 (10): 930. doi:10.1176/ajp.113.10.930. PMID 13402989.
^ ^a ^b Campbell CH, Sleeper HG (April 1956). "Cetadiol (5-androstene-3 16-diol) in the treatment of hospitalized alcoholics". The American Journal of Psychiatry. 112 (10): 845. doi:10.1176/ajp.112.10.845. PMID 13302491.
^ Wexler D, Leiderman PH, Mendelson J, Kubzansky P, Solomon P (April 1958). "The effect of cetadiol on delirium tremens, alcoholic hallucinosis, and alcohol withdrawal". The American Journal of Psychiatry. 114 (10): 935–936. doi:10.1176/ajp.114.10.935. PMID 13508929.

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