Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H23O2.Na |
Molecular Weight | 294.3638 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C([O-])C=C4
InChI
InChIKey=NHTBIADYQKCUHK-CMZLOHJFSA-M
InChI=1S/C18H24O2.Na/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;/q;+1/p-1/t14-,15-,16+,17+,18+;/m1./s1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C18H24O2 |
Molecular Weight | 272.382 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11250930https://pubchem.ncbi.nlm.nih.gov/compound/222757http://www.drugbank.ca/drugs/DB00783Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020375s027lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11250930https://pubchem.ncbi.nlm.nih.gov/compound/222757http://www.drugbank.ca/drugs/DB00783
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020375s027lbl.pdf
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. 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. Estradiol is used 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). Estradiol is marketed under the brand name Climara (among others), indicated for: the treatment of moderate to severe vasomotor symptoms due to menopause, treatment of symptoms of vulvar and vaginal atrophy due to menopause, treatment of hypoestrogenism due to hypogonadism, castration or primary ovarian failure and prevention of postmenopausal osteoporosis.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25231731https://books.google.ru/books?id=L4YQ50SbBnsC&pg=PA223&lpg=PA223&dq=estradiol+cross+blood+brain+barrier&source=bl&ots=1XAPNkXVXI&sig=_VCp7qIuyiwBe9cGGJDMvmdR8zg&hl=ru&sa=X&ved=0ahUKEwjjk6vD8r7PAhWCFywKHU3xD8c4ChDoAQg4MAU#v=onepage&q=estradiol%20cross%20blood%20brain%20barrier&f=false, retrieved from
Curator's Comment: Estrogen Effects in Psychiatric Disorders
Niels Bergemann,Anita Riecher-Rössler, p.223
Originator
Sources: http://www.google.ru/patents/US2054271https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA1478&lpg=PA1478&dq=ESTRADIOL+year+introduced&source=bl&ots=N5lzH8ALwu&sig=V9zqvrxhsCojxBpoWmAWSN7AXcc&hl=ru&sa=X&ved=0ahUKEwj975678L7PAhVGXSwKHb5cBkUQ6AEISDAH#v=onepage&q=ESTRADIOL%20year%20introduced&f=false, retrieved from Pharmaceutical Manufacturing Encyclopedia, 3rd Edition : William Andrew Publishing, p.1475
Curator's Comment: Introduced in 1952
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P08842 Gene ID: 412.0 Gene Symbol: STS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11250930 |
|||
Target ID: CHEMBL206 Sources: http://www.drugbank.ca/drugs/DB00783 |
0.0084 nM [EC50] | ||
Target ID: CHEMBL242 Sources: http://www.drugbank.ca/drugs/DB00783 |
1.4 nM [EC50] | ||
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16309907 |
19.1 nM [IC50] | ||
Target ID: CHEMBL206 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/222757 |
0.13 nM [Ki] | ||
Target ID: CHEMBL242 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/222757 |
0.09 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CLIMARA Approved UseClimara is an estrogen indicated for:
•Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause
•Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause
•Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure
•Prevention of Postmenopausal Osteoporosis Launch Date1974 |
|||
Preventing | CLIMARA Approved UseClimara is an estrogen indicated for:
•Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause
•Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause
•Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure
•Prevention of Postmenopausal Osteoporosis Launch Date1974 |
|||
Primary | CLIMARA Approved UseClimara is an estrogen indicated for:
•Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause
•Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause
•Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure
•Prevention of Postmenopausal Osteoporosis Launch Date1974 |
|||
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.7 pg/mL |
0.25 mg 1 times / day steady-state, topical dose: 0.25 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
ESTRADIOL plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
92 pg/mL |
0.05 mg 1 times / day multiple, topical dose: 0.05 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
ESTRADIOL plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
236 pg × h/mL |
0.25 mg 1 times / day steady-state, topical dose: 0.25 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
ESTRADIOL plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10 h |
0.25 mg 1 times / day steady-state, topical dose: 0.25 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
ESTRADIOL plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
1.75 h |
0.05 mg 1 times / day multiple, topical dose: 0.05 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
ESTRADIOL plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes | |||
Sources: https://pubs.acs.org/doi/abs/10.1021/mp900077q Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
minor | |||
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minor | |||
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minor | |||
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minor | |||
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minor | |||
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minor | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
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no | |||
Page: - |
no | |||
Page: - |
yes [Km 7 uM] | |||
Page: - |
yes | |||
Page: - |
yes | |||
Sources: https://www.pnas.org/content/93/18/9776.short Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
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yes | |||
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yes | |||
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yes | |||
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yes | |||
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yes | |||
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yes | |||
Page: - |
yes | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of estradiol benzoate on the proliferation of osteogenic cells in fetal rat fibulae cultured in vitro. | 1978 Mar |
|
Sulfation of estrone and 17 beta-estradiol in human liver. Catalysis by thermostable phenol sulfotransferase and by dehydroepiandrosterone sulfotransferase. | 1992 May-Jun |
|
[The effect of adrenaline and 17beta-estradiol sulfate on transmembrane potentials of guinea pig cardiomyocytes]. | 1996 Dec |
|
Suppressive effects of estradiol on 2,3,7,8-tetrachlorodibenzo-p-dioxin-mediated transcriptional activation of murine Cyp1a-1 in mouse hepatoma Hepa 1c1c7 cells. | 1998 Nov 27 |
|
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | 1998 Oct |
|
Differential regulation of c-fos expression in estrogen-induced hamster renal tumors compared with kidney not due to creation of an estrogen-response element by point mutation in the gene's flanking sequence. | 1999 Apr |
|
Estrogenicity of bisphenol A in a human endometrial carcinoma cell line. | 1999 Apr 25 |
|
Estrogen and aryl hydrocarbon responsiveness of ECC-1 endometrial cancer cells. | 1999 Apr 25 |
|
Growth stimulation of a rat pituitary cell line MtT/E-2 by environmental estrogens in vitro and in vivo. | 1999 Aug |
|
Lack of mutations in DNA polymerase beta of estradiol-induced hamster kidney tumors: sequence of hamster DNA polymerase beta cDNA. | 1999 Aug |
|
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture. | 1999 Dec |
|
Estrogen-induced pituitary tumor development in the ACI rat not inhibited by dietary energy restriction. | 1999 Dec |
|
Rapid inhibition of rat brain mitochondrial proton F0F1-ATPase activity by estrogens: comparison with Na+, K+ -ATPase of porcine cortex. | 1999 Feb 26 |
|
Low-dose bioactivity of xenoestrogens in animals: fetal exposure to low doses of methoxychlor and other xenoestrogens increases adult prostate size in mice. | 1999 Jan-Mar |
|
[Physiology and exploration of the gonadotropic axis]. | 1999 Jun 15 |
|
Estrogenic potential of certain pyrethroid compounds in the MCF-7 human breast carcinoma cell line. | 1999 Mar |
|
Effects of environmental estrogens on tumor necrosis factor alpha-mediated apoptosis in MCF-7 cells. | 1999 Nov |
|
Estrogen directly respresses gonadotropin-releasing hormone (GnRH) gene expression in estrogen receptor-alpha (ERalpha)- and ERbeta-expressing GT1-7 GnRH neurons. | 1999 Nov |
|
The aryl hydrocarbon receptor (AHR)/AHR nuclear translocator (ARNT) heterodimer interacts with naturally occurring estrogen response elements. | 1999 Nov 25 |
|
Perinatal exposure to estrogenic compounds and the subsequent effects on the prostate of the adult rat: evaluation of inflammation in the ventral and lateral lobes. | 1999 Nov-Dec |
|
Circadian expression of the steroid 15 alpha-hydroxylase (Cyp2a4) and coumarin 7-hydroxylase (Cyp2a5) genes in mouse liver is regulated by the PAR leucine zipper transcription factor DBP. | 1999 Oct |
|
Acute activation of Maxi-K channels (hSlo) by estradiol binding to the beta subunit. | 1999 Sep 17 |
|
Involvement of cyclooxygenase 2 in the protective effect of 17beta-estradiol on hypercholesterolemic rabbit aorta. | 2000 Aug 28 |
|
Molecular analysis of the inhibition of monocyte chemoattractant protein-1 gene expression by estrogens and xenoestrogens in MCF-7 cells. | 2000 Jan |
|
Intrinsic alcohol dehydrogenase and hydroxysteroid dehydrogenase activities of human mitochondrial short-chain L-3-hydroxyacyl-CoA dehydrogenase. | 2000 Jan 1 |
|
Crosstalk between estrogen receptor alpha and the aryl hydrocarbon receptor in breast cancer cells involves unidirectional activation of proteasomes. | 2000 Jul 28 |
|
Dramatic suppression of plasma and urinary prostate specific antigen and human glandular kallikrein by antiandrogens in male-to-female transsexuals. | 2000 Mar |
|
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat. | 2000 Nov-Dec |
|
Relative binding affinity does not predict biological response to xenoestrogens in rat endometrial adenocarcinoma cells. | 2000 Oct |
|
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta. | 2000 Oct |
|
Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells. | 2000 Oct |
|
Antiestrogenic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin in mouse uterus: critical role of the aryl hydrocarbon receptor in stromal tissue. | 2000 Oct |
|
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
|
Estrogen induces the Akt-dependent activation of endothelial nitric-oxide synthase in vascular endothelial cells. | 2001 Feb 2 |
|
Female steroid hormones modulate receptors for nerve growth factor in rat dorsal root ganglia. | 2001 Jan |
|
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment. | 2001 Jan |
|
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes. | 2001 Jan |
|
Neuroprotection by estradiol. | 2001 Jan |
|
Affinity labeling of rat glutathione S-transferase isozyme 1-1 by 17beta -iodoacetoxy-estradiol-3-sulfate. | 2001 Jan 19 |
|
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum. | 2001 Jan 5 |
|
Acquisition of Lubrol insolubility, a common step for growth hormone and prolactin in the secretory pathway of neuroendocrine cells. | 2001 Jan 5 |
|
In vivo regulation of syndecan-3 expression in the rat uterus by 17 beta-estradiol. | 2001 Jan 5 |
|
Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus. | 2007 Mar 10 |
|
Complex actions of estradiol-3-sulfate in late gestation fetal brain. | 2011 Jul |
|
[Study of gonadal hormone drugs in blocking filovirus entry of cells in vitro]. | 2015 Dec |
|
Changes in Expression of Connexin Isoforms in the Caudal Epididymis of Adult Sprague-Dawley Rats exposed to Estradiol Benzoate or Flutamide at the Neonatal Age. | 2016 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Estradiol benzoate is not approved by the FDA for use in humans in the United States.
Unknown
Route of Administration:
Unknown
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21273638
Estradiol-3-sulfate (E2SO4) infused intracerebroventricularly (icv) significantly increased plasma adrenocorticotropic hormone (ACTH) and cortisol concentrations. All minipumps in the treated fetuses were filled with E2SO4 in the vehicle (water) and minipumps in the control fetuses were filled with vehicle only. These minipumps deliver a constant infusion of 5 μL/h; the concentration of E2SO4 in infusates was therefore 8.33 μg/μL. It was concluded, that E2SO4 had complex actions on the fetal brain, which might involve deconjugation by steroid sulfatase. But that the net result of direct E2SO4 icv infusion was more complex than could be accounted for by infusion of E2 alone.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 13:04:37 GMT 2023
by
admin
on
Sat Dec 16 13:04:37 GMT 2023
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Record UNII |
37UIZ63WWM
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Record Status |
Validated (UNII)
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Record Version |
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Common Name | English |
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15399-28-7
Created by
admin on Sat Dec 16 13:04:37 GMT 2023 , Edited by admin on Sat Dec 16 13:04:37 GMT 2023
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37UIZ63WWM
Created by
admin on Sat Dec 16 13:04:37 GMT 2023 , Edited by admin on Sat Dec 16 13:04:37 GMT 2023
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145996636
Created by
admin on Sat Dec 16 13:04:37 GMT 2023 , Edited by admin on Sat Dec 16 13:04:37 GMT 2023
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ACTIVE MOIETY |