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Estradiol phosphate
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    Estradiol phosphate

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    Estradiol phosphate
    Estradiol 17-phosphate.svg
    Estradiol phosphate molecule ball.png
    Clinical data
    Other names Estradiol 17β-phosphate; Estra-1,3,5(10)-triene-3,17β-diol 17β-(dihydrogen phosphate); 3-Hydroxyestra-1,3,5(10)-trien-17β-yl phosphate
    Drug class Estrogen; Estrogen ester
    Identifiers
    • [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] dihydrogen phosphate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C18H25O5P
    Molar mass 352.367 g·mol−1
    3D model (JSmol)
    • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OP(=O)(O)O)CCC4=C3C=CC(=C4)O
    • InChI=1S/C18H25O5P/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)23-24(20,21)22/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H2,20,21,22)/t14-,15-,16+,17+,18+/m1/s1
    • Key:BBWXLCKRYRQQPL-ZBRFXRBCSA-N

    Estradiol phosphate, or estradiol 17β-phosphate, also known as estra-1,3,5(10)-triene-3,17β-diol 17β-(dihydrogen phosphate), is an estrogen which was never marketed. It is an estrogen ester, specifically an ester of estradiol with phosphoric acid, and acts as a prodrug of estradiol in the body. It is rapidly cleaved by phosphatase enzymes into estradiol upon administration. Estradiol phosphate is contained within the chemical structures of two other estradiol esters, polyestradiol phosphate (a polymer of estradiol phosphate) and estramustine phosphate (estradiol 3-normustine 17β-phosphate), both of which have been marketed for the treatment of prostate cancer.

    Structural properties of selected estradiol esters
    Estrogen Structure Ester(s) Relative
    mol. weight
    Relative
    E2 contentb
    log Pc
    Position(s) Moiet(ies) Type Lengtha
    Estradiol
    Estradiol.svg
    1.00 1.00 4.0
    Estradiol acetate
    Estradiol 3-acetate.svg
    C3 Ethanoic acid Straight-chain fatty acid 2 1.15 0.87 4.2
    Estradiol benzoate
    Estradiol benzoate.svg
    C3 Benzenecarboxylic acid Aromatic fatty acid – (~4–5) 1.38 0.72 4.7
    Estradiol dipropionate
    Estradiol dipropionate.svg
    C3, C17β Propanoic acid (×2) Straight-chain fatty acid 3 (×2) 1.41 0.71 4.9
    Estradiol valerate
    Estradiol valerate.svg
    C17β Pentanoic acid Straight-chain fatty acid 5 1.31 0.76 5.6–6.3
    Estradiol benzoate butyrate
    Estradiol butyrate benzoate.svg
    C3, C17β Benzoic acid, butyric acid Mixed fatty acid – (~6, 2) 1.64 0.61 6.3
    Estradiol cypionate
    Estradiol 17 beta-cypionate.svg
    C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.46 0.69 6.9
    Estradiol enanthate
    Estradiol enanthate.png
    C17β Heptanoic acid Straight-chain fatty acid 7 1.41 0.71 6.7–7.3
    Estradiol dienanthate
    Estradiol dienanthate.svg
    C3, C17β Heptanoic acid (×2) Straight-chain fatty acid 7 (×2) 1.82 0.55 8.1–10.4
    Estradiol undecylate
    Estradiol undecylate.svg
    C17β Undecanoic acid Straight-chain fatty acid 11 1.62 0.62 9.2–9.8
    Estradiol stearate
    Estradiol stearate structure.svg
    C17β Octadecanoic acid Straight-chain fatty acid 18 1.98 0.51 12.2–12.4
    Estradiol distearate
    Estradiol distearate.svg
    C3, C17β Octadecanoic acid (×2) Straight-chain fatty acid 18 (×2) 2.96 0.34 20.2
    Estradiol sulfate
    Estradiol sulfate.svg
    C3 Sulfuric acid Water-soluble conjugate 1.29 0.77 0.3–3.8
    Estradiol glucuronide
    Estradiol sulfate.svg
    C17β Glucuronic acid Water-soluble conjugate 1.65 0.61 2.1–2.7
    Estramustine phosphated
    Estramustine phosphate.svg
    C3, C17β Normustine, phosphoric acid Water-soluble conjugate 1.91 0.52 2.9–5.0
    Polyestradiol phosphatee
    Polyestradiol phosphate.svg
    C3–C17β Phosphoric acid Water-soluble conjugate 1.23f 0.81f 2.9g
    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.

    See also



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