Global InformationEstradiol information
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| Names | |
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| Pronunciation | /ˌɛstrəˈdaɪoʊl/ ES-trə-DY-ohl[1][2] |
| IUPAC name
Estra-1,3,5(10)-triene-3,17β-diol
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| 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
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| Identifiers | |
CAS Number
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3D model (JSmol)
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| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.000.022 |
| EC Number |
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| KEGG |
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PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |
Chemical formula
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C18H24O2 |
| Molar mass | 272.38 g/mol |
Magnetic susceptibility (χ)
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-186.6·10−6 cm3/mol |
| Pharmacology | |
ATC code
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G03CA03 (WHO) |
| License data |
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Routes of
administration |
Oral, sublingual, intranasal, topical/transdermal, vaginal, intramuscular or subcutaneous (as an ester), subdermal implant |
| Pharmacokinetics: | |
Bioavailability
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Oral: <5%[3] |
Protein binding
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~98%:[3][4] • Albumin: 60% • SHBG: 38% • Free: 2% |
Metabolism
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Liver (via hydroxylation, sulfation, glucuronidation) |
Biological half-life
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Oral: 13–20 hours[3] Sublingual: 8–18 hours[5] Topical (gel): 36.5 hours[6] |
Excretion
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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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Infobox references
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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.
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Ozon_1972was invoked but never defined (see the help page). - ^ 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.