| Stereochemistry | ABSOLUTE |
| Molecular Formula | C29H34O4 |
| Molecular Weight | 446.5779 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](OC(=O)CCC)[C@@]1(C)CC[C@]3([H])C4=CC=C(OC(=O)C5=CC=CC=C5)C=C4CC[C@@]23[H]
InChI
InChIKey=MKYFGNOOEKZNPW-ZRJUGLEFSA-N
InChI=1S/C29H34O4/c1-3-7-27(30)33-26-15-14-25-24-12-10-20-18-21(32-28(31)19-8-5-4-6-9-19)11-13-22(20)23(24)16-17-29(25,26)2/h4-6,8-9,11,13,18,23-26H,3,7,10,12,14-17H2,1-2H3/t23-,24-,25+,26+,29+/m1/s1
| Molecular Formula | C29H34O4 |
| Molecular Weight | 446.5779 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Originator
Approval Year
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| 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 | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Sourcing
| Vendor/Aggregator | ID | URL |
|---|---|---|
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 |
|
| [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 |
|
| Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells. | 2000 Apr |
|
| Effect of chlorinated hydrocarbons on expression of cytochrome P450 1A1, 1A2 and 1B1 and 2- and 4-hydroxylation of 17beta-estradiol in female Sprague-Dawley rats. | 2000 Aug |
|
| WISP-2 as a novel estrogen-responsive gene in human breast cancer cells. | 2000 Aug 18 |
|
| Involvement of cyclooxygenase 2 in the protective effect of 17beta-estradiol on hypercholesterolemic rabbit aorta. | 2000 Aug 28 |
|
| Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells. | 2000 Dec |
|
| Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells. | 2000 Jan-Feb |
|
| 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 |
|
| Six high-priority organochlorine pesticides, either singly or in combination, are nonestrogenic in transfected HeLa cells. | 2000 Mar-Apr |
|
| Estradiol acts as a germ cell survival factor in the human testis in vitro. | 2000 May |
|
| Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes. | 2000 May |
|
| Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation. | 2000 Nov 14 |
|
| Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta. | 2000 Nov 17 |
|
| 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 |
|
| Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo. | 2001 Apr |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart. | 2001 Jan |
|
| Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle. | 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 |
|
| Reduction of gamma-aminobutyric acid-ergic neurotransmission as a putative mechanism of radiation induced activation of the gonadotropin releasing-hormone-pulse generator leading to precocious puberty in female rats. | 2001 Jan 5 |
|
| 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 |
|
| 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 |
|
| Evaluation of Effects of Topical Estradiol Benzoate Application on Cutaneous Wound Healing in Ovariectomized Female Mice. | 2016 |
Patents
Sample Use Guides
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.
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
Estradiol_benzoate_butyrate | PRIMARY | |||
|
263-807-9 | PRIMARY | |||
|
63042-18-2 | PRIMARY | |||
|
ZE4IGI4UMH | PRIMARY | |||
|
DTXSID20978979 | PRIMARY | |||
|
100000184196 | PRIMARY | |||
|
67081 | PRIMARY |
