Estradiol 17β-benzoate

Estradiol 17β-benzoate
Clinical data
Other names	E2-17B; ZYC30
Drug class	Estrogen; Estrogen ester
Identifiers
	IUPAC name [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] benzoate;
CAS Number	983-30-2;
PubChem CID	66420;
ChemSpider	59794;
UNII	3GFX41Z289;
CompTox Dashboard (EPA)	DTXSID90243545 ;
Chemical and physical data
Formula	C25H28O3
Molar mass	376.496 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)C4=CC=CC=C4)CCC5=C3C=CC(=C5)O;
	InChI InChI=1S/C25H28O3/c1-25-14-13-20-19-10-8-18(26)15-17(19)7-9-21(20)22(25)11-12-23(25)28-24(27)16-5-3-2-4-6-16/h2-6,8,10,15,20-23,26H,7,9,11-14H2,1H3/t20-,21-,22+,23+,25+/m1/s1; Key:AAGOOGMSOHOVSE-BZDYCCQFSA-N;

Estradiol 17β-benzoate (E2-17B) is an estrogen and an estrogen ester—specifically, the C17β benzoate ester of estradiol—which was never marketed.^[1]^[2]^[3] It is the C17β positional isomer of the better-known and clinically used estradiol ester estradiol benzoate (estradiol 3-benzoate; Progynon-B).^[1] Estradiol 17β-benzoate was first described in the 1930s.^[4]

References

^ ^a ^b Junkmann K, Witzel H (1957). "[Chemistry and pharmacology of steroid hormone esters]" [Chemistry and pharmacology of steroid hormone esters]. Zeitschrift für Vitamin-, Hormon- und Fermentforschung (in German). 9 (1–2): 97–143 contd. PMID 13531579.
^ Perez E, Cai ZY, Covey DF, Simpkins JW (2005). "Neuroprotective effects of estratriene analogs: structure-activity relationships and molecular optimization". Drug Development Research. 66 (2): 78–92. doi:10.1002/ddr.20047. ISSN 0272-4391. S2CID 86133327.
^ Yi KD, Perez E, Yang S, Liu R, Covey DF, Simpkins JW (March 2011). "The assessment of non-feminizing estrogens for use in neuroprotection". Brain Research. 1379: 61–70. doi:10.1016/j.brainres.2010.11.058. PMC 3048764. PMID 21111714.
^ Parkes AS (April 1937). "Relative duration of action of various esters of oestrone, oestradiol and oestriol". The Biochemical Journal. 31 (4): 579–585. doi:10.1042/bj0310579. PMC 1266977. PMID 16746375.