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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 | |
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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) | |
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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.[1][2] It is rapidly cleaved by phosphatase enzymes into estradiol upon administration.[1][2] 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.[2][3][1]
Estrogen | Structure | Ester(s) | Relative mol. weight |
Relative E2 contentb |
log Pc | ||||
---|---|---|---|---|---|---|---|---|---|
Position(s) | Moiet(ies) | Type | Lengtha | ||||||
Estradiol | ![]() |
– | – | – | – | 1.00 | 1.00 | 4.0 | |
Estradiol acetate | ![]() |
C3 | Ethanoic acid | Straight-chain fatty acid | 2 | 1.15 | 0.87 | 4.2 | |
Estradiol benzoate | ![]() |
C3 | Benzoic acid | Aromatic fatty acid | – (~4–5) | 1.38 | 0.72 | 4.7 | |
Estradiol dipropionate | ![]() |
C3, C17β | Propanoic acid (×2) | Straight-chain fatty acid | 3 (×2) | 1.41 | 0.71 | 4.9 | |
Estradiol valerate | ![]() |
C17β | Pentanoic acid | Straight-chain fatty acid | 5 | 1.31 | 0.76 | 5.6–6.3 | |
Estradiol benzoate butyrate | ![]() |
C3, C17β | Benzoic acid, butyric acid | Mixed fatty acid | – (~6, 2) | 1.64 | 0.61 | 6.3 | |
Estradiol cypionate | ![]() |
C17β | Cyclopentylpropanoic acid | Cyclic fatty acid | – (~6) | 1.46 | 0.69 | 6.9 | |
Estradiol enanthate | ![]() |
C17β | Heptanoic acid | Straight-chain fatty acid | 7 | 1.41 | 0.71 | 6.7–7.3 | |
Estradiol dienanthate | ![]() |
C3, C17β | Heptanoic acid (×2) | Straight-chain fatty acid | 7 (×2) | 1.82 | 0.55 | 8.1–10.4 | |
Estradiol undecylate | ![]() |
C17β | Undecanoic acid | Straight-chain fatty acid | 11 | 1.62 | 0.62 | 9.2–9.8 | |
Estradiol stearate | ![]() |
C17β | Octadecanoic acid | Straight-chain fatty acid | 18 | 1.98 | 0.51 | 12.2–12.4 | |
Estradiol distearate | ![]() |
C3, C17β | Octadecanoic acid (×2) | Straight-chain fatty acid | 18 (×2) | 2.96 | 0.34 | 20.2 | |
Estradiol sulfate | ![]() |
C3 | Sulfuric acid | Water-soluble conjugate | – | 1.29 | 0.77 | 0.3–3.8 | |
Estradiol glucuronide | ![]() |
C17β | Glucuronic acid | Water-soluble conjugate | – | 1.65 | 0.61 | 2.1–2.7 | |
Estramustine phosphated | ![]() |
C3, C17β | Normustine, phosphoric acid | Water-soluble conjugate | – | 1.91 | 0.52 | 2.9–5.0 | |
Polyestradiol phosphatee | ![]() |
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 or cyclic 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 alsoedit
Referencesedit
- ^ a b c Cavalli F, Kaye SB, Hansen HH, Armitage JO, Piccart-Gebhart M (12 September 2009). "Appendix: Endocrine Therapies". Textbook of Medical Oncology (Fourth ed.). CRC Press. pp. 442–. ISBN 978-0-203-09289-7.
- ^ a b c Gunnarsson PO, Norlén BJ (1988). "Clinical pharmacology of polyestradiol phosphate". The Prostate. 13 (4): 299–304. doi:10.1002/pros.2990130405. PMID 3217277. S2CID 33063805.
- ^ Abbou CC, Beaumont V, Chopin D, Deburge JP, Beaumont JL, Auvert J (29 June 2013). "Treatment of prostatic cancer with diethylstilboestrol and detection of the vascular risk". In Smith PH (ed.). Cancer of the Prostate and Kidney. Springer Science & Business Media. pp. 359–. ISBN 978-1-4684-4349-3.
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File:Estradiol 17-phosphate.svg
File:Estradiol phosphate molecule ball.png
Drug class
Estrogen (medication)
Estrogen ester
IUPAC nomenclature of chemistry
CAS Registry Number
PubChem#CID
ChemSpider
Unique Ingredient Identifier
ChEMBL
CompTox Chemicals Dashboard
Q27289257#P3117
Chemical formula
Molar mass
JSmol
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International Chemical Identifier
Estrogen (medication)
Estrogen ester
Ester
Estradiol (medication)
Phosphoric acid
Prodrug
Bond cleavage
Phosphatase
Enzyme
Chemical structure
Estradiol ester
Polyestradiol phosphate
Polymer
Estramustine phosphate
Normustine
Prostate cancer
Template:Structural properties of selected estradiol esters
Template talk:Structural properties of selected estradiol esters
Special:EditPage/Template:Structural properties of selected estradiol esters
Estradiol (medication)
File:Estradiol.svg
Estradiol acetate
File:Estradiol 3-acetate.svg
Ethanoic acid
Estradiol benzoate
File:Estradiol benzoate.svg
Benzoic acid
Estradiol dipropionate
File:Estradiol dipropionate.svg
Propanoic acid
Estradiol valerate
File:Estradiol valerate.svg
Pentanoic acid
Estradiol benzoate butyrate
File:Estradiol butyrate benzoate.svg
Benzoic acid
Butyric acid
Estradiol cypionate
File:Estradiol 17 beta-cypionate.svg
Cyclopentylpropanoic acid
Estradiol enanthate
File:Estradiol enanthate.png
Heptanoic acid
Estradiol dienanthate
File:Estradiol dienanthate.svg
Heptanoic acid
Estradiol undecylate
File:Estradiol undecylate.svg
Undecanoic acid
Estradiol stearate
File:Estradiol stearate structure.svg
Octadecanoic acid
Estradiol distearate
File:Estradiol distearate.svg
Octadecanoic acid
Estradiol sulfate
File:Estradiol sulfate.svg
Sulfuric acid
Estradiol glucuronide
File:Estradiol sulfate.svg
Glucuronic acid
Estramustine phosphate
File:Estramustine phosphate.svg
Normustine
Phosphoric acid
Polyestradiol phosphate
File:Polyestradiol phosphate.svg
Phosphoric acid
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Special:BookSources/978-1-4684-4349-3
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