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Estrone phosphate information


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
  • 1240-03-5 checkY
PubChem CID
  • 445419
ChemSpider
  • 393068
UNII
  • 52ZYE9C9X9
ChEMBL
  • ChEMBL1232577
CompTox Dashboard (EPA)
  • DTXSID60924677 Edit this at Wikidata
Chemical and physical data
FormulaC18H23O5P
Molar mass350.351 g·mol−1
3D model (JSmol)
  • Interactive image
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

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]

  1. ^ a b Bourne GH (May 1954). "The histochemical dephosphorylation of oestrogen phosphates". The Journal of Physiology. 124 (2): 409–416. doi:10.1113/jphysiol.1954.sp005117. PMC 1366276. PMID 13175141.
  2. ^ a b c 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. ^ a b c Anderson CJ, Lucas LJ, Widlanski TS (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". Bioorganic & Medicinal Chemistry. 19 (20): 5999–6005. doi:10.1016/j.bmc.2011.08.046. PMID 21925885.

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Estrone phosphate

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Estrone phosphate (E1P), or estrone 3-phosphate, is an estrogen and steroid sulfatase inhibitor which was never marketed. It has similar affinity for...

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Estrone

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Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the...

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List of estrogen esters

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Estrone cyanate Estrone enanthate Estrone enanthate benzilic acid hydrazone Estrone glucuronide Estrone phosphate Estrone propionate Estrone sulfamate (EMATE;...

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Estrone glucuronide

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Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase...

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Estrogen ester

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estrogen, most typically of estradiol but also of other estrogens such as estrone, estriol, and even nonsteroidal estrogens like diethylstilbestrol. Esterification...

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Estromustine

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(developmental code name Leo 271 f), also known as estrone 17β-3-N-bis(2-chloroethyl)carbamate or estrone–cytostatic complex, is a major active metabolite...

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List of estrogens

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This is a list of steroidal estrogens or derivatives of estradiol, estrone, and estriol. Most esters of these estrogens are not included in this list;...

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Estradiol

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formation of androstenedione, which is then converted by aromatase into estrone and is subsequently converted into estradiol. Alternatively, androstenedione...

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Estrone sulfate

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Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate. In addition to...

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Estramustine

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Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and...

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Estrone acetate

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Estrone acetate (brand name Hovigal) is a semisynthetic, steroidal estrogen. It is an estrogen ester, specifically, an ester of estrone. Hydroxyestrone...

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Estrone cyanate

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Estrone cyanate, or estrone 3-O-cyanate, also known as estrocyanate, is an estrogen and an estrogen ester – specifically, the 3-O-cyanate ester of estrone...

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Pharmacokinetics of estradiol

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Polyestradiol phosphate (ESTRADURIN) is also available for intramuscular use in prostatic carcinoma. Various sulfate esters of Estrone, U.S.P., are available...

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Estrone sulfamate

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Estrone sulfamate (EMATE; developmental code name J994), or estrone-3-O-sulfamate, is a steroid sulfatase (STS) inhibitor which has not yet been marketed...

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Androstenedione

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weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related...

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Conjugated estrogens

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mixture of the sodium salts of estrogen conjugates found in horses, such as estrone sulfate and equilin sulfate. CEEs are available in the form of both natural...

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Polyestriol phosphate

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Polyestriol phosphate (PE3P, SEP), sold under the brand names Gynäsan, Klimadurin, and Triodurin, is an estrogen medication which was previously used...

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Estrogen

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three major endogenous estrogens that have estrogenic hormonal activity: estrone (E1), estradiol (E2), and estriol (E3). Estradiol, an estrane, is the most...

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Estrone tetraacetylglucoside

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Estrone tetraacetylglucoside (brand name Glucovex, Glycovex) is a semisynthetic, steroidal estrogen. It is an estrogen ester, specifically, an ester of...

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Sulfate conjugate

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steroids. Estrone sulfate is the most abundant of all the estrogens in the human body. Estrone sulfate is synthesized by the enzyme estrone sulfotransferase...

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Estrogen conjugate

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include sulfate and/or glucuronide conjugates of estradiol, estrone, and estriol: Sulfated: Estrone 3-sulfate (E1S) Estradiol 3-sulfate (E2S, E2-3S) and estradiol...

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Polyestradiol phosphate

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Polyestradiol phosphate (PEP), sold under the brand name Estradurin, is an estrogen medication which is used primarily in the treatment of prostate cancer...

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Esterified estrogens

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of approximately 53% sodium estrone sulfate and 25% sodium equilin sulfate, while EEs contain about 75 to 85% sodium estrone sulfate and 6 to 11% sodium...

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