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

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]

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

References

  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.
Categories