Estrone phosphate

Estrone phosphate (E1P), or estrone 3-phosphate, is an estrogen and steroid sulfatase inhibitor which was never marketed.[1][2][3] It has similar affinity for steroid sulfatase as estrone sulfate and acts as a competitive inhibitor of the enzyme.[2][3][4] In contrast to estrone sulfate however, it is not hydrolyzed by steroid sulfatase and is instead metabolized by phosphatases.[1][2][3]

Estrone phosphate
Clinical data
Other namesEstrone 3-phosphate; E1P; O3-Phosphonoestrone; 17-Oxoestra-1,3,5(10)-trien-3-yl dihydrogen phosphate
Drug classEstrogen; Steroid sulfatase inhibitor
Identifiers
IUPAC name
  • [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] dihydrogen phosphate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H23O5P
Molar mass350.351 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OP(=O)(O)O
InChI
  • InChI=1S/C18H23O5P/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H2,20,21,22)/t14-,15-,16+,18+/m1/s1
  • Key:XYNRXDLLYXFCRS-CBZIJGRNSA-N

See also

References
  1. Bourne GH (May 1954). "The histochemical dephosphorylation of oestrogen phosphates". J. Physiol. (Lond.). 124 (2): 409–16. doi:10.1113/jphysiol.1954.sp005117. PMC 1366276. PMID 13175141.
  2. Li PK, Pillai R, Dibbelt L (March 1995). "Estrone sulfate analogs as estrone sulfatase inhibitors". Steroids. 60 (3): 299–306. doi:10.1016/0039-128x(94)00048-h. PMID 7792836. S2CID 3070641.
  3. Anderson, C. J.; Lucas, Linda J. H.; Widlanski, Theodore S. (1995). "Molecular Recognition in Biological Systems: Phosphate Esters vs Sulfate Esters and the Mechanism of Action of Steroid Sulfatases". Journal of the American Chemical Society. 117 (13): 3889–3890. doi:10.1021/ja00118a034. ISSN 0002-7863.
  4. Phan CM, Liu Y, Kim BM, Mostafa Y, Taylor SD (October 2011). "Inhibition of steroid sulfatase with 4-substituted estrone and estradiol derivatives". Bioorg. Med. Chem. 19 (20): 5999–6005. doi:10.1016/j.bmc.2011.08.046. PMID 21925885.


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