Estradiol 17β-benzoate

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]

Not to be confused with Estradiol benzoate.
Estradiol 17β-benzoate
Clinical data
Other namesE2-17B; ZYC30
Drug classEstrogen; 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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H28O3
Molar mass376.496 g·mol−1
3D model (JSmol)
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

See also

References
  1. Junkmann K, Witzel H (1957). "Chemie und Pharmakologie von Steroidhormon-Estern" [Chemistry and pharmacology of steroid hormone esters]. Z Vitam Horm Fermentforsch (in German). 9 (1–2): 97–143 contd. PMID 13531579.
  2. Perez, Evelyn; Cai, Zu Yun; Covey, Douglas F.; Simpkins, James W. (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.
  3. 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 Res. 1379: 61–70. doi:10.1016/j.brainres.2010.11.058. PMC 3048764. PMID 21111714.
  4. Parkes AS (April 1937). "Relative duration of action of various esters of oestrone, oestradiol and oestriol". Biochem. J. 31 (4): 579–85. doi:10.1042/bj0310579. PMC 1266977. PMID 16746375.



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