Estradiol dibenzoate

Estradiol dibenzoate (EDB), also known as estradiol 3,17β-dibenzoate, is an estrogen ester which was developed in the 1930s and was never marketed.[1][2][3][4][5][6][7] It is the C3 and C17β benzoate diester of estradiol.[1] Estradiol dibenzoate has a longer duration of action than estradiol benzoate (estradiol 3-benzoate) by depot injection.[2][3][4][5][6][7]

Estradiol dibenzoate
Clinical data
Other namesEDB; Estradiol 3,17β-dibenzoate; Estra-1,3,5(10)-triene-3,17β-diol 3,17β-dibenzoate
Identifiers
IUPAC name
  • [(8R,9S,13S,14S,17S)-3-benzoyloxy-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
FormulaC32H32O4
Molar mass480.604 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)OC(=O)C6=CC=CC=C6
InChI
  • InChI=1S/C32H32O4/c1-32-19-18-26-25-15-13-24(35-30(33)21-8-4-2-5-9-21)20-23(25)12-14-27(26)28(32)16-17-29(32)36-31(34)22-10-6-3-7-11-22/h2-11,13,15,20,26-29H,12,14,16-19H2,1H3/t26-,27-,28+,29+,32+/m1/s1
  • Key:QSEBTTYLHXQXSF-CAHAWPIUSA-N

See also

References
  1. Friedrich W. Derz, ed. (1976). ChemPRODUCTindex, Volumes 1-2. De Gruyter. pp. 881–. ISBN 978-3-11-002141-7. OCLC 2619908.
  2. Parkes AS (February 1938). "Effective Absorption of Hormones". Br Med J. 1 (4024): 371–3. doi:10.1136/bmj.1.4024.371. PMC 2085798. PMID 20781252.
  3. Parkes, A. S. (March 1942). "Rate of Absorption of Esters of Oestrone and Oestradiol as Determined by Feather Tests". Journal of Endocrinology. 3 (1): 288–291. doi:10.1677/joe.0.0030288. eISSN 1479-6805. ISSN 0022-0795.
  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.
  5. Miescher K, Scholz C, Tschopp E (April 1938). "The activation of female sex hormones: alpha-Oestradiol and its di-esters". Biochem J. 32 (4): 725–32. doi:10.1042/bj0320725. PMC 1264097. PMID 16746680.
  6. R. Deanesly; Alan Sterling Parkes (7 December 1937). "Factors influencing the effectiveness of administered hormones". Proceedings of the Royal Society of London. Series B, Biological Sciences. 124 (836): 279–298. Bibcode:1937RSPSB.124..279D. doi:10.1098/rspb.1937.0086. ISSN 2053-9193. S2CID 85076285.
  7. Parkes, A.S.; Emmens, C.W. (1944). "Effect of Androgens and Estrogens on Birds". Vitamins & Hormones. Vol. 2. Elsevier. pp. 361–408. doi:10.1016/S0083-6729(08)60290-3. ISBN 9780127098029. ISSN 0083-6729.


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