Estradiol phosphate

(Redirected from Estradiol 17β-phosphate)

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]

Estradiol phosphate
Clinical data
Other namesEstradiol 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 classEstrogen; 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
FormulaC18H25O5P
Molar mass352.367 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
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
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 also

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References

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  1. ^ 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.
  2. ^ 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.
  3. ^ 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.