Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H30O5 |
| Molecular Weight | 434.5241 |
| 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)C5=C(OC(C)=O)C=CC=C5)C=C4
InChI
InChIKey=KNJUTXJFANOVGR-HXVSAZQXSA-N
InChI=1S/C27H30O5/c1-16(28)31-24-6-4-3-5-22(24)26(30)32-18-8-10-19-17(15-18)7-9-21-20(19)13-14-27(2)23(21)11-12-25(27)29/h3-6,8,10,15,20-21,23,25,29H,7,9,11-14H2,1-2H3/t20-,21-,23+,25+,27+/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
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
Page: - |
yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Km 7 uM] | ||||
| yes | ||||
| yes | ||||
Page: - |
yes | |||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 |
|
| Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha. | 1999 Oct |
|
| Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells. | 2000 Apr |
|
| Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites. | 2000 Apr 1 |
|
| Expression of the estrogen-regulated gene Nip2 during rat brain maturation. | 2000 Apr-Jun |
|
| Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells. | 2000 Dec |
|
| High concentrations of bisphenol A induce cell growth and prolactin secretion in an estrogen-responsive pituitary tumor cell line. | 2000 Feb 1 |
|
| Proteinase inhibitor 9, an inhibitor of granzyme B-mediated apoptosis, is a primary estrogen-inducible gene in human liver cells. | 2000 Feb 25 |
|
| The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution. | 2000 Jan |
|
| Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens. | 2000 Jan 15 |
|
| Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells. | 2000 Jan-Feb |
|
| Six high-priority organochlorine pesticides, either singly or in combination, are nonestrogenic in transfected HeLa cells. | 2000 Mar-Apr |
|
| Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes. | 2000 May |
|
| Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene. | 2000 Nov |
|
| Female sex steroids: effects upon microglial cell activation. | 2000 Nov 1 |
|
| Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation. | 2000 Nov 14 |
|
| 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 |
|
| Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells. | 2000 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Follicle selection in cattle: role of luteinizing hormone. | 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 |
|
| Sex steroid hormones enhance immune function in male and female Siberian hamsters. | 2001 Jan |
|
| Rapid and reversible inhibition of brain aromatase activity. | 2001 Jan |
|
| Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes. | 2001 Jan |
|
| Influence of gender and sex hormones on nicotine acute pharmacological effects in mice. | 2001 Jan |
|
| Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults. | 2001 Jan |
|
| Estradiol levels in psychotic disorders. | 2001 Jan |
|
| Neuroprotection by estradiol. | 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 |
|
| 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 |
|
| 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 |
|
| 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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
183168
Created by
admin on Sat Dec 16 15:30:24 GMT 2023 , Edited by admin on Sat Dec 16 15:30:24 GMT 2023
|
PRIMARY | |||
|
J9B90ASJ1Y
Created by
admin on Sat Dec 16 15:30:24 GMT 2023 , Edited by admin on Sat Dec 16 15:30:24 GMT 2023
|
PRIMARY | |||
|
DTXSID30912001
Created by
admin on Sat Dec 16 15:30:24 GMT 2023 , Edited by admin on Sat Dec 16 15:30:24 GMT 2023
|
PRIMARY | |||
|
Estradiol acetylsalicylate
Created by
admin on Sat Dec 16 15:30:24 GMT 2023 , Edited by admin on Sat Dec 16 15:30:24 GMT 2023
|
PRIMARY | |||
|
111111-98-9
Created by
admin on Sat Dec 16 15:30:24 GMT 2023 , Edited by admin on Sat Dec 16 15:30:24 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
