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Estradiol

 

 

 

 

CAS No:
50-28-2 Category:
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Product Details:

  • Product Name: Estradiol
  • CAS #: 50-28-2
  • Mode of Action:

    Estradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.

  • Pharmacodynamics:

    Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone, and estriol, at the cellular level.

  • Metabolism:

    Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.

  • Toxicity:

    Can cause nausea and vomiting, and withdrawal bleeding may occur in females.

  • IUPAC: (1S, 10R, 11S, 14S, 15S)-15-methyltetracyclo[8.7.0.0, {2, 7}.0, {11, 15}]heptadeca-2(7), 3, 5-triene-5, 14-diol
  • ATC: G03CA01" G03CA03" L02AA02" L02AA03
  • PubChem: 5757
  • DrugBank: DB00783 (APRD00311)
  • Formula: C18H24O2
  • Molecular Mass: 272.4
  • Synonyms: 17beta oestradiol, 17β-estra-1,3,5(10)-triene-3,17-diol, 17β-estradiol, 17β-oestradiol, beta-Estradiol, cis-estradiol, Estradiol-17beta
  • AHFS Code: 08:16.0
  • InChl: 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
  • General Reference:

     

    1. Pentikainen V, Erkkila K, Suomalainen L, Parvinen M, Dunkel L: Estradiol acts as a germ cell survival factor in the human testis in vitro. J Clin Endocrinol Metab. 2000 May;85(5):2057-67. Pubmed
    2. Sharpe RM, Skakkebaek NE: Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;341(8857):1392-5. Pubmed
    3. Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. Pubmed
    4. Carani C, Qin K, Simoni M, Faustini-Fustini M, Serpente S, Boyd J, Korach KS, Simpson ER: Effect of testosterone and estradiol in a man with aromatase deficiency. N Engl J Med. 1997 Jul 10;337(2):91-5. Pubmed
    5. Behl C, Widmann M, Trapp T, Holsboer F: 17-beta estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochem Biophys Res Commun. 1995 Nov 13;216(2):473-82. Pubmed
    6. Schmidt JW, Wollner D, Curcio J, Riedlinger J, Kim LS: Hormone replacement therapy in menopausal women: Past problems and future possibilities. Gynecol Endocrinol. 2006 Oct;22(10):564-77. Pubmed
    7. Foresta C, Zuccarello D, Biagioli A, De Toni L, Prana E, Nicoletti V, Ambrosini G, Ferlin A: Oestrogen stimulates endothelial progenitor cells via oestrogen receptor-alpha. Clin Endocrinol (Oxf). 2007 Oct;67(4):520-5. Epub 2007 Jun 15. Pubmed
    8. Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. Pubmed

     

  • Product Description:

    Estradiol (also known as E2 or 17β-estradiol) is a naturally occurring hormone that circulates endogenously within the human body. It is the most potent form of mammalian estrogenic steroids and acts as the major female sex hormone. As such, estradiol plays an essential role in the regulation of the menstrual cycle, in the development of puberty and secondary female sex characteristics, as well as in ageing and several hormonally-mediated disease states. Estrogen mediates its effects across the body through potent agonism of the Estrogen Receptor (ER), which is located in various tissues including in the breasts, uterus, ovaries, skin, prostate, bone, fat, and brain. Estradiol binds to both subtypes of the Estrogen Receptor: Estrogen Receptor Alpha (ERα) and Estrogen Receptor Beta (ERβ). Estradiol also acts as a potent agonist of G Protein-coupled Estrogen Receptor (GPER), which has recently been recognized as a major mediator of estradiol's rapid cellular effects.

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