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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O5S
Molecular Weight 352.445
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 17.BETA.-ESTRADIOL SULFATE

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=CC=C(OS(O)(=O)=O)C=C4CC[C@@]23[H]

InChI

InChIKey=QZIGLSSUDXBTLJ-ZBRFXRBCSA-N
InChI=1S/C18H24O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,17+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H24O5S
Molecular Weight 352.445
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08842
Gene ID: 412.0
Gene Symbol: STS
Target Organism: Homo sapiens (Human)
0.0084 nM [EC50]
1.4 nM [EC50]
19.1 nM [IC50]
0.13 nM [Ki]
0.09 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLIMARA

Approved Use

Climara 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 Date

1974
Preventing
CLIMARA

Approved Use

Climara 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 Date

1974
Primary
CLIMARA

Approved Use

Climara 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 Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical 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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
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
Relative binding affinity does not predict biological response to xenoestrogens in rat endometrial adenocarcinoma cells.
2000 Oct
Repression of chick multidrug resistance-associated protein 1 (chMRP1) gene expression by estrogen.
2000 Oct 31
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
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
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
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
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
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
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
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
[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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:39:49 GMT 2023
Edited
by admin
on Fri Dec 15 19:39:49 GMT 2023
Record UNII
4NKQ3751P6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
17.BETA.-ESTRADIOL SULFATE
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL (17.BETA.)-, 3-(HYDROGEN SULFATE)
Common Name English
ESTRADIOL 3-SULFATE
Common Name English
((8R,9S,13S,14S,17S)-17-HYDROXY-13-METHYL-6,7,8,9,11,12,14,15,16,17-DECAHYDROCYCLOPENTA(A)PHENANTHREN-3-YL) HYDROGEN SULFATE
Common Name English
ESTRADIOL-3-SULFATE
Common Name English
ESTRADIOL-17BETA 3-SULFATE
Common Name English
ESTRADIOL METABOLITE (ESTRADIOL-17BETA 3-SULFATE)
Common Name English
17.BETA.-ESTRADIOL 3-SULFATE
Common Name English
ESTRADIOL, 3-(HYDROGEN SULFATE)
Common Name English
Code System Code Type Description
CAS
481-96-9
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
PUBCHEM
66416
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
FDA UNII
4NKQ3751P6
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID30964000
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
WIKIPEDIA
Estradiol sulfate
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
MESH
C028628
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
CHEBI
4866
Created by admin on Fri Dec 15 19:39:49 GMT 2023 , Edited by admin on Fri Dec 15 19:39:49 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE