Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C18H24O2.H2O |
Molecular Weight | 562.7792 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4.[H][C@@]56CC[C@H](O)[C@@]5(C)CC[C@]7([H])C8=C(CC[C@@]67[H])C=C(O)C=C8
InChI
InChIKey=ZVVGLAMWAQMPDR-WVEWYJOQSA-N
InChI=1S/2C18H24O2.H2O/c2*1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20;/h2*3,5,10,14-17,19-20H,2,4,6-9H2,1H3;1H2/t2*14-,15-,16+,17+,18+;/m11./s1
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 |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 | |||
Page: - |
minor | |||
Page: - |
minor | |||
Page: - |
minor | |||
Page: - |
minor | |||
Page: - |
minor | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
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 | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Estradiol prevents and testosterone promotes Fas-dependent apoptosis in CD4+ Th2 cells by altering Bcl 2 expression. | 1999 |
|
Comparison of the pharmacokinetics of 17 beta-estradiol after a single 4-day application of Oesclim 50, Oesclim 100, and Vivelle 0.05 (Menorest 50) transdermal delivery systems. | 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 |
|
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 |
|
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 |
|
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 |
|
Transcriptional activation of c-fos protooncogene by 17beta-estradiol: mechanism of aryl hydrocarbon receptor-mediated inhibition. | 1999 Sep |
|
Acute activation of Maxi-K channels (hSlo) by estradiol binding to the beta subunit. | 1999 Sep 17 |
|
Estradiol and pesticide methoxychlor do not exhibit additivity or synergism in the reproductive tract of adult ovariectomized mice. | 2000 Jul 28 |
|
Crosstalk between estrogen receptor alpha and the aryl hydrocarbon receptor in breast cancer cells involves unidirectional activation of proteasomes. | 2000 Jul 28 |
|
Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription. | 2000 Mar |
|
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat. | 2000 Nov-Dec |
|
Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells. | 2000 Oct |
|
Repression of chick multidrug resistance-associated protein 1 (chMRP1) gene expression by estrogen. | 2000 Oct 31 |
|
Hormone status selects for spontaneous somatic androgen receptor variants that demonstrate specific ligand and cofactor dependent activities in autochthonous prostate cancer. | 2001 Apr 6 |
|
Vitellogenin-induced pathology in male summer flounder (Paralichthys dentatus). | 2001 Feb |
|
Female steroid hormones modulate receptors for nerve growth factor in rat dorsal root ganglia. | 2001 Jan |
|
Increased expression of a novel heat shock protein transcript in the mouse uterus during decidualization and in response to progesterone. | 2001 Jan |
|
Follicle selection in cattle: role of luteinizing hormone. | 2001 Jan |
|
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment. | 2001 Jan |
|
Oestrogen-induced changes in the synaptology of the monkey (Cercopithecus aethiops) arcuate nucleus during gonadotropin feedback. | 2001 Jan |
|
Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart. | 2001 Jan |
|
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. | 2001 Jan |
|
Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats. | 2001 Jan 10 |
|
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum. | 2001 Jan 5 |
|
Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus. | 2007 Mar 10 |
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
Fri Dec 15 15:57:12 GMT 2023
by
admin
on
Fri Dec 15 15:57:12 GMT 2023
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Record UNII |
CXY7B3Q98Z
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
ZOELY (AUTHORIZED: CONTRACEPTION)
Created by
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EU-Orphan Drug |
EU/3/05/275
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admin on Fri Dec 15 15:57:13 GMT 2023 , Edited by admin on Fri Dec 15 15:57:13 GMT 2023
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NCI_THESAURUS |
C478
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Code System | Code | Type | Description | ||
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DBSALT001383
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PRIMARY | |||
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236859
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PRIMARY | RxNorm | ||
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100000089218
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PRIMARY | |||
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154274
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PRIMARY | |||
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DTXSID60858948
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PRIMARY | |||
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CXY7B3Q98Z
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PRIMARY | |||
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Estradiol hemihydrate
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PRIMARY | |||
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CHEMBL135
Created by
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PRIMARY | |||
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C47992
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PRIMARY | |||
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m5028
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PRIMARY | Merck Index | ||
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CXY7B3Q98Z
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PRIMARY | |||
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SUB11941MIG
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PRIMARY | |||
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35380-71-3
Created by
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PRIMARY |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (UV)
EP
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ANHYDROUS->SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |