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Estradiol

This article is about estradiol as a hormone. For its use as a medication, see Estradiol (medication).

Estradiol
The chemical structure of estradiol.
A ball-and-stick model of estradiol.
Names
Pronunciation /ˌɛstrəˈdaɪoʊl/ ES-trə-DY-ohl[1][2]
IUPAC name
Estra-1,3,5(10)-triene-3,17β-diol
Systematic IUPAC name
(1S,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
Other names
Oestradiol; E2; 17β-Estradiol; 17β-Oestradiol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.022 Edit this at Wikidata
EC Number
  • 200-023-8
KEGG
UNII
  • InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1 checkY
    Key: VOXZDWNPVJITMN-ZBRFXRBCSA-N checkY
  • C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@@H]2O)O
Properties
C18H24O2
Molar mass 272.38 g/mol
-186.6·10−6 cm3/mol
Pharmacology
G03CA03 (WHO)
License data
Oral, sublingual, intranasal, topical/transdermal, vaginal, intramuscular or subcutaneous (as an ester), subdermal implant
Pharmacokinetics:
Oral: <5%[3]
~98%:[3][4]
• Albumin: 60%
• SHBG: 38%
• Free: 2%
Liver (via hydroxylation, sulfation, glucuronidation)
Oral: 13–20 hours[3]
Sublingual: 8–18 hours[5]
Topical (gel): 36.5 hours[6]
Urine: 54%[3]
Feces: 6%[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible for the development of female secondary sexual characteristics such as the breasts, widening of the hips and a female pattern of fat distribution. It is also important in the development and maintenance of female reproductive tissues such as the mammary glands, uterus and vagina during puberty, adulthood and pregnancy.[7] It also has important effects in many other tissues including bone, fat, skin, liver, and the brain.

Though estradiol levels in males are much lower than in females, estradiol has important roles in males as well. Apart from humans and other mammals, estradiol is also found in most vertebrates and crustaceans, insects, fish, and other animal species.[8][9]

Estradiol is produced especially within the follicles of the ovaries, but also in other tissues including the testicles, the adrenal glands, fat, liver, the breasts, and the brain. Estradiol is produced in the body from cholesterol through a series of reactions and intermediates.[10] The major pathway involves the formation of androstenedione, which is then converted by aromatase into estrone and is subsequently converted into estradiol. Alternatively, androstenedione can be converted into testosterone, which can then be converted into estradiol. Upon menopause in females, production of estrogens by the ovaries stops and estradiol levels decrease to very low levels.

In addition to its role as a natural hormone, estradiol is used as a medication, for instance in menopausal hormone therapy and feminizing hormone therapy for transgender women; for information on estradiol as a medication, see the estradiol (medication) article.

  1. ^ Cite error: The named reference FordRoach2013 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference HochadelMosby2015 was invoked but never defined (see the help page).
  3. ^ a b c d e Cite error: The named reference StanczykArcher2013 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference FalconeHurd2007 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference PriceBlauer1997 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference NauntonAl Hadithy2006 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pmid7083198 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Mechoulam_2005 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Ozon_1972 was invoked but never defined (see the help page).
  10. ^ Saldanha, Colin J., Luke Remage-Healey, and Barney A. Schlinger. "Synaptocrine signaling: steroid synthesis and action at the synapse." Endocrine reviews 32.4 (2011): 532–549.

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