Estradiol distearate

Estradiol distearate (EDS), also known as estradiol dioctadecanoate, is an estrogen and a estrogen ester which was never marketed.[1][2] It is a long-acting prodrug of estradiol in the body.[2]

Structural properties of selected estradiol esters
EstrogenStructureEster(s)Relative
mol. weight		Relative
E2 contentb		log Pc
Position(s)Moiet(ies)TypeLengtha
Estradiol
––––1.001.004.0
Estradiol acetate
C3Ethanoic acidStraight-chain fatty acid21.150.874.2
Estradiol benzoate
C3Benzenecarboxylic acidAromatic fatty acid– (~4–5)1.380.724.7
Estradiol dipropionate
C3, C17βPropanoic acid (×2)Straight-chain fatty acid3 (×2)1.410.714.9
Estradiol valerate
C17βPentanoic acidStraight-chain fatty acid51.310.765.6–6.3
Estradiol benzoate butyrate
C3, C17βBenzoic acid, butyric acidMixed fatty acid– (~6, 2)1.640.616.3
Estradiol cypionate
C17βCyclopentylpropanoic acidAromatic fatty acid– (~6)1.460.696.9
Estradiol enanthate
C17βHeptanoic acidStraight-chain fatty acid71.410.716.7–7.3
Estradiol dienanthate
C3, C17βHeptanoic acid (×2)Straight-chain fatty acid7 (×2)1.820.558.1–10.4
Estradiol undecylate
C17βUndecanoic acidStraight-chain fatty acid111.620.629.2–9.8
Estradiol stearate
C17βOctadecanoic acidStraight-chain fatty acid181.980.5112.2–12.4
Estradiol distearate
C3, C17βOctadecanoic acid (×2)Straight-chain fatty acid18 (×2)2.960.3420.2
Estradiol sulfate
C3Sulfuric acidWater-soluble conjugate–1.290.770.3–3.8
Estradiol glucuronide
C17βGlucuronic acidWater-soluble conjugate–1.650.612.1–2.7
Estramustine phosphated
C3, C17βNormustine, phosphoric acidWater-soluble conjugate–1.910.522.9–5.0
Polyestradiol phosphatee
C3–C17βPhosphoric acidWater-soluble conjugate–1.23f0.81f2.9g
Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative estradiol content by weight (i.e., relative estrogenic exposure). c = Experimental or predicted octanol/water partition coefficient (i.e., lipophilicity/hydrophobicity). Retrieved from PubChem, ChemSpider, and DrugBank. d = Also known as estradiol normustine phosphate. e = Polymer of estradiol phosphate (~13 repeat units). f = Relative molecular weight or estradiol content per repeat unit. g = log P of repeat unit (i.e., estradiol phosphate). Sources: See individual articles.
Estradiol distearate
Clinical data
Other namesEDS; Estradiol 3,17β-distearate; Estradiol dioctadecanoate; Estra-1,3,5(10)-triene-3,17β-diol 3,17β-dioctadecanoate
Identifiers
IUPAC name
  • [(8R,9S,13S,14S,17S)-13-methyl-3-octadecanoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] octadecanoate
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC54H92O4
Molar mass805.326 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)OC(=O)CCCCCCCCCCCCCCCCC)C
InChI
  • InChI=1S/C54H92O4/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-52(55)57-46-37-39-47-45(44-46)36-38-49-48(47)42-43-54(3)50(49)40-41-51(54)58-53(56)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h37,39,44,48-51H,4-36,38,40-43H2,1-3H3/t48-,49-,50+,51+,54+/m1/s1
  • Key:BBBPCTNBNYFUOV-NXCWIAOISA-N

See also

References
  1. Deb S, Wähälä K (October 2010). "Rapid synthesis of long chain fatty acid esters of steroids in ionic liquids with microwave irradiation: expedient one-pot procedure for estradiol monoesters". Steroids. 75 (10): 740–4. doi:10.1016/j.steroids.2010.03.005. PMID 20347856. S2CID 1695106.
  2. Vazquez-Alcantara MA, Menjivar M, Garcia GA, Díaz-Zagoya JC, Garza-Flores J (December 1989). "Long-acting estrogenic responses of estradiol fatty acid esters". Journal of Steroid Biochemistry. 33 (6): 1111–8. doi:10.1016/0022-4731(89)90417-2. PMID 2515394.
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