Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H32O3 |
| Molecular Weight | 356.4984 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC(=O)C(C)(C)C)C=C4
InChI
InChIKey=LVPJFQMQWHLSQN-WCZGSDDISA-N
InChI=1S/C23H32O3/c1-22(2,3)21(25)26-15-6-8-16-14(13-15)5-7-18-17(16)11-12-23(4)19(18)9-10-20(23)24/h6,8,13,17-20,24H,5,7,9-12H2,1-4H3/t17-,18-,19+,20+,23+/m1/s1
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) |
|||
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 |
19.1 nM [IC50] | ||
Target ID: CHEMBL206 |
0.13 nM [Ki] | ||
Target ID: CHEMBL242 |
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
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|---|---|---|---|---|
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Drug as victim
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PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of estradiol benzoate on the proliferation of osteogenic cells in fetal rat fibulae cultured in vitro. | 1978 Mar |
|
| An increase of pituitary 3', 5' cyclic adenosine monophosphate produced by estradiol benzoate in vitro: possible implication of this increase in the secretion of luteinizing hormone. | 1978 May |
|
| 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 |
|
| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997 Mar |
|
| Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. | 1998 Oct |
|
| Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells. | 2000 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 |
|
| NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1. | 2000 Sep |
|
| Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
|
| 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 |
|
| 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 |
|
| Unique protein determinants of the subtype-selective ligand responses of the estrogen receptors (ERalpha and ERbeta ) at AP-1 sites. | 2001 Feb 9 |
|
| Effects of follicle-stimulating hormone with and without luteinizing hormone on serum hormone concentrations, follicle growth, and intrafollicular estradiol and aromatase activity in gonadotropin-releasing hormone-immunized heifers. | 2001 Jan |
|
| Female steroid hormones modulate receptors for nerve growth factor in rat dorsal root ganglia. | 2001 Jan |
|
| Regulation and role of vascular endothelial growth factor in the corpus luteum during mid-pregnancy in rats. | 2001 Jan |
|
| Increased expression of a novel heat shock protein transcript in the mouse uterus during decidualization and in response to progesterone. | 2001 Jan |
|
| Regulation of progesterone receptors and decidualization in uterine stroma of the estrogen receptor-alpha knockout mouse. | 2001 Jan |
|
| Pregnancy stimulates secretion of adrenocorticotropin and nitric oxide from peripheral bovine lymphocytes. | 2001 Jan |
|
| Follicle selection in cattle: role of luteinizing hormone. | 2001 Jan |
|
| Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats. | 2001 Jan |
|
| Changes in follicle-stimulating hormone and follicle populations during the ovarian cycle of the common marmoset. | 2001 Jan |
|
| Estradiol-induced attenuation of pulmonary hypertension is not associated with altered eNOS expression. | 2001 Jan |
|
| Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride. | 2001 Jan |
|
| Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment. | 2001 Jan |
|
| Sex steroid hormones enhance immune function in male and female Siberian hamsters. | 2001 Jan |
|
| Rapid and reversible inhibition of brain aromatase activity. | 2001 Jan |
|
| Oestrogen-induced changes in the synaptology of the monkey (Cercopithecus aethiops) arcuate nucleus during gonadotropin feedback. | 2001 Jan |
|
| Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes. | 2001 Jan |
|
| Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle. | 2001 Jan |
|
| Dose-response relationships and pharmacokinetics of vitellogenin in rainbow trout after intravascular administration of 17alpha-ethynylestradiol. | 2001 Jan |
|
| Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. | 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 |
|
| 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 |
|
| Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1. | 2001 Mar 2 |
|
| Estrogen decreases osteoclast formation by down-regulating receptor activator of NF-kappa B ligand (RANKL)-induced JNK activation. | 2001 Mar 23 |
|
| Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2. | 2001 Mar 23 |
|
| The unusual binding properties of the third distinct teleost estrogen receptor subtype ERbetaa are accompanied by highly conserved amino acid changes in the ligand binding domain. | 2004 Jun |
|
| 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 |
|
| Evaluation of Effects of Topical Estradiol Benzoate Application on Cutaneous Wound Healing in Ovariectomized Female Mice. | 2016 |
|
| Effects of Exposure to Estradiol Benzoate or Flutamide at the Weaning Age on Expression of Connexins in the Caudal Epididymis of Adult Rat. | 2016 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
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.
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E2ZLL4E609
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10594457
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DTXSID20216166
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65944-91-4
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ACTIVE MOIETY
SUBSTANCE RECORD
