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Estrone information


Estrone
Names
IUPAC name
3-Hydroxyestra-1,3,5(10)-trien-17-one
Systematic IUPAC name
(3aS,3bR,9bS,11aS)-7-Hydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
Oestrone; E1
Identifiers
CAS Number
  • 53-16-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17263 checkY
ChEMBL
  • ChEMBL1405 checkY
ChemSpider
  • 5660 checkY
ECHA InfoCard 100.000.150 Edit this at Wikidata
KEGG
  • D00067 checkY
PubChem CID
  • 5870
UNII
  • 2DI9HA706A checkY
CompTox Dashboard (EPA)
  • DTXSID4022367 Edit this at Wikidata
InChI
  • InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1 ☒N
    Key: DNXHEGUUPJUMQT-CBZIJGRNSA-N ☒N
SMILES
  • O=C4[C@]3(CC[C@@H]2c1ccc(O)cc1CC[C@H]2[C@@H]3CC4)C
Properties
Chemical formula
C18H22O2
Molar mass 270.366 g/mol
Melting point 254.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone.[1] It is one of three major endogenous estrogens, the others being estradiol and estriol.[1] Estrone, as well as the other estrogens, are synthesized from cholesterol and secreted mainly from the gonads, though they can also be formed from adrenal androgens in adipose tissue.[2] Relative to estradiol, both estrone and estriol have far weaker activity as estrogens.[1] Estrone can be converted into estradiol, and serves mainly as a precursor or metabolic intermediate of estradiol.[1][3] It is both a precursor and metabolite of estradiol.[4][1]

In addition to its role as a natural hormone, estrone has been used as a medication, for instance in menopausal hormone therapy; for information on estrone as a medication, see the estrone (medication) article.

  1. ^ a b c d e Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ Hornstein T, Schwerin JL (1 January 2012). Biology of Women. Cengage Learning. pp. 369–. ISBN 978-1-285-40102-7.
  3. ^ Cite error: The named reference KeepUtian2012 was invoked but never defined (see the help page).
  4. ^ Chervenak J (October 2009). "Bioidentical hormones for maturing women". Maturitas. 64 (2): 86–89. doi:10.1016/j.maturitas.2009.08.002. PMID 19766414.

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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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Estrone sulfotransferase

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Estrone sulfotransferase (EST) (EC 2.8.2.4), also known as estrogen sulfotransferase, is an enzyme that catalyzes the transformation of an unconjugated...

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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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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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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 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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Pharmacokinetics of estradiol

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estrone and 65% into estrone sulfate. About 5% of estrone and 1.4% of estrone sulfate is converted back into estradiol. An additional 21% of estrone sulfate...

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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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Estrone methyl ether

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Estrone methyl ether, or estrone 3-methyl ether, is a synthetic estrogen and estrogen ether – specifically, the C3 methyl ether of estrone – which was...

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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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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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Estriol

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one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost undetectable...

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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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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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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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Equilin

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replacement therapy (HRT) for menopausal symptoms in the United States. Estrone sulfate is the major estrogen in CEEs (about 50%) while equilin sulfate...

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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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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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Estrogenic substances

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of estrogens, including estrone, 17β-estradiol, 17α-estradiol, and/or equilin. The medication was thought to contain estrone as its major active ingredient...

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Estrone benzoate

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Estrone benzoate, or estrone 3-benzoate, is a synthetic estrogen and estrogen ester – specifically, the C3 benzoate ester of estrone – which was first...

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Estradiol valerate

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(17β-HSD). As approximately 80% of estradiol is metabolized into estrone (and estrone sulfate) by 17β-HSD during first-pass metabolism, this improves the...

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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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