Estradiol 3-propionate

Estradiol 3-propionate, or 3-propanoylestradiol, also known as estra-1,3,5(10)-triene-3,17β-diol 3-propionate, is a semisynthetic, steroidal estrogen that was never marketed.[1][2] It is an estrogen ester, specifically, a propionic acid ester of estradiol, and acts as a prodrug to it in vivo.[1][2] The chemical structure of estradiol 3-propionate is contained within estradiol dipropionate, estrapronicate, and orestrate, all of which are also estradiol esters.[2]

Not to be confused with Estradiol 17β-propionate.
Estradiol 3-propionate
Clinical data
Other namesEstradiol 3-propanoate; 3-Propanoylestradiol; 3,17β-Hydroxyestra-1,3,5(10)-trien-3-yl propionate
Routes of
administration		Intramuscular injection, vaginal[1]
Drug classEstrogen; Estrogen ester
ATC code
  • None
Identifiers
IUPAC name
  • [(8R,9S,13S,14S,17S)-17-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] propanoate
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28O3
Molar mass328.452 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=O)Oc1ccc2c(c1)CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
InChI
  • InChI=InChI=1S/C21H28O3/c1-3-20(23)24-14-5-7-15-13(12-14)4-6-17-16(15)10-11-21(2)18(17)8-9-19(21)22/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19?,21?/m1/s1
  • Key:InChIKey=FONFXFZWMZJFCD-NYKHLBABSA-N

See also

References
  1. Woolfson AD, Elliott GR, Gilligan CA, Passmore CM (1999). "Design of an intravaginal ring for the controlled delivery of 17 beta-estradiol as its 3-acetate ester". J Control Release. 61 (3): 319–28. doi:10.1016/s0168-3659(99)00148-0. PMID 10477804.
  2. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.



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