Home > Compound List > Product Information
Estradiol_Molecular_structure_CAS_50-28-2)
Click picture or here to close

Estradiol

Catalog No. DB00783 Name DrugBank
CAS Number 50-28-2 Website http://www.ualberta.ca/
M. F. C18H24O2 Telephone (780) 492-3111
M. W. 272.38196 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 663

SYNONYMS

IUPAC name
(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
IUPAC Traditional name
estradiol
Brand Name
Ginedisc
Lynoral
Diogyn
Evorel
Climaderm
Bardiol
Compudose
Compudose 200
Estreva
Estring
Extrasorb
Gynergon
Gynoestryl
Gynpolar
Oestergon
Aerodiol
Agofollin
Aquadiol
Diogynets
Encore
Esclim
Estraderm Tts
Estroclim 50
Estrovite
Femtrace
Femtran
Ginosedol
Gynestrel
Oestrogel
Profoliol
Progynon
Progynon Dh
Tradelia
Trocosone
Macrol
Amnestrogen
Combipatch
Compudose 365
Corpagen
Depo-Estradiol
Dermestril
Dihydromenformon
Dihydrotheelin
Divigel
Estinyl
Estrace
Estraderm
Estradurin
Estrifam
Estrofem 2
Estrofem Forte
Feminone
Femogen
Follicyclin
Gynodiol
Nordicol
Oestradiol
Oestroglandol
Ovahormon
Ovociclina
Ovocycline
Perlatanol
Profoliol B
Progynon-Dh
Sandrena Gel
Sisare Gel
Sk-Estrogens
Soldep
Sotipox
Syndiol
Vivelle
Zumenon
Menest
Menorest
Microdiol
Alora
Altrad
Climara
Delestrogen
Dimenformon
Dimenformon Prolongatum
Estrasorb
Estring Vaginal Ring
Estroclim
Estrogel
Estrogens, Esterified
Femestral
Femestrol
Fempatch
Femring
Oestradiol R
Oestrogynal
Ovasterol
Ovastevol
Ovocyclin
Ovocylin
Primofol
Ricifon
Ritsifon
Systen
Trial Sat
Vagifem
Zerella
Elestrin
Evamist
Vivelle-DOT
Innofem
Lamdiol
Macrodiol
Menostar
Synonyms
D-Estradiol
Estradiol-17beta
Estradiol Valerate
D-Oestradiol
Cis-Oestradiol
Estradiol Cypionate
Dihydroxyestrin
Dihydroxyoestrin
Dihydroxyesterin
Dihydrofollicular Hormone
Dihydrofolliculin
Cis-Estradiol
estradiol
Beta-Estradiol
17-beta

DATABASE IDS

PubChem CID 5757
CAS Number 50-28-2
PubChem SID 46508115

PROPERTIES

Hydrophobicity(logP) 4.2
Solubility 3.6 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved; investigational
Description Generally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized. [PubChem]
Indication For the treatment of urogenital symptoms associated with post-menopausal atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria).
Pharmacology Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone and estriol, at the cellular level.
Toxicity Can cause nausea and vomiting, and withdrawal bleeding may occur in females.
Affected Organisms
Humans and other mammals
Biotransformation Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.
Absorption 43%
Half Life 36 hours
Protein Binding >95%
Elimination Estradiol, estrone and estriol are excreted in the urine along with glucuronide and sulfate conjugates.
References
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]
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]
Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. [Pubmed]
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]
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]
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]
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]
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]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. Pubmed