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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O5S
Molecular Weight 350.4311
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE SULFATE

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CCC1=O)OS(=O)(=O)O

InChI

InChIKey=JKKFKPJIXZFSSB-CBZIJGRNSA-N
InChI=1S/C18H22O5S/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/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H22O5S
Molecular Weight 350.4311
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://books.google.ru/books?id=Thtz7On_lhEC&pg=PA356&lpg=PA356&dq=DL-ESTRONE retrieved from The Hormones V1: Physiology, Chemistry and Applications By Gregory Pincus, Thimann Kenneth Vivian Pincus Gregory, p.356

Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase. Estrogens enter the cells of responsive tissues (e.g. female organs, breasts, hypothalamus, pituitary) where they interact with estrogen receptors. Hormone-bound estrogen receptors dimerize, translocate to the nucleus of cells and bind to estrogen response elements (ERE) of genes. Binding to ERE alters the transcription rate of affected genes. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) release from the anterior pituitary. Estrone dl-Form is a derivative of estrone. As early as 1935 extensive research programs directed toward the total synthesis of the female sex hormone estrone were well under way. These studies have since been continued with increasing interest in laboratories all over the world. In 1942 Bachmann, Kushner and Stevenson succeeded in synthesizing a stereoisomer of the hormone,''estrone a." Using essentially the same synthetic scheme as Bachmann, et al., Anner and Miescher were able to isolate additional stereoisomers including dl-estrone (Estrone, (+-)-Isomer) . Six of the eight possible racemic forms, estrone, a-f, have now been reported. Dl-Estrone (Estrone, (+-)-Isomer) is less active than Estrone.

CNS Activity

Curator's Comment:: Estrone sulfate crossed the blood brain barrier in rats.

Originator

Curator's Comment:: Estrone is one of the hormones responsible for sexual development and function in females.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Primary
Estragyn

Approved Use

Estragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms. Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma.
Primary
Estragyn

Approved Use

Estragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms. Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma.
Primary
THEELIN

Approved Use

For management of Menopausal and postmenopausal disorders
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
733 pg/mL
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
550 pg × h/mL
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.
2001
Potential fertility--defining the window of opportunity.
2001
Trial protocol and sample result of a study comparing the Clearplan Easy Fertility Monitor with serum hormone and vaginal ultrasound measurements in the determination of ovulation.
2001
Home monitoring with the ClearPlan Easy Fertility Monitor for fertility awareness.
2001
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women.
2001 Apr
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.
2001 Apr
Oestrogens and oestrogenic activity in raw and treated water in Severn Trent Water.
2001 Apr
Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation.
2001 Apr
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001 Apr
Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep.
2001 Apr 2
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.
2001 Feb
Dietary oleoyl-estrone delays the growth rate of young rats.
2001 Feb
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease.
2001 Feb
Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol and.
2001 Feb
Periovulatory changes in catfish ovarian oestradiol-17beta, oestrogen-2-hydroxylase and catechol-O-methyltransferase during GnRH analogue-induced ovulation and in vitro induction of oocyte maturation by catecholoestrogens.
2001 Feb
Predominant 4-hydroxylation of estradiol by constitutive cytochrome P450s in the female ACI rat liver.
2001 Feb
Differential in vitro suppressive effects of steroids on leukocyte phagocytosis in two teleosts, tilapia and common carp.
2001 Feb
The human estrogen receptor alpha dimer binds a single SRC-1 coactivator molecule with an affinity dictated by agonist structure.
2001 Feb 23
Hormone contents in peripheral tissues after correct and off-label use of growth promoting hormones in cattle: effect of the implant preparations Filaplix-H, Raglo, Synovex-H and Synovex Plus.
2001 Jan
Bioequivalence and relative bioavailability of three estradiol and norethisterone acetate-containing hormone replacement therapy tablets.
2001 Jan
Effect of GnRH immunisation on hormonal levels, sexual behaviour, semen quality and testicular morphology in mature stallions.
2001 Jan
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.
2001 Jan 22
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Mechanisms of estradiol inactivation in primate endometrium.
2001 Jan 22
Beneficial effects of pravastatin in peri- and postmenopausal hyperlipidemic women: a 5-year study on serum lipid and sex hormone levels.
2001 Jan 31
Chalcones are potent inhibitors of aromatase and 17beta-hydroxysteroid dehydrogenase activities.
2001 Jan 5
Influence of endogenous androgens on carotid wall in postmenopausal women.
2001 Jan-Feb
The selective estrogen enzyme modulator (SEEM) in breast cancer.
2001 Jan-Mar
Menopausal experiences and bone density of Mayan women in Yucatan, Mexico.
2001 Jul-Aug
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female.
2001 Jun
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.
2001 Jun
Association of genetic polymorphisms in UGT1A1 with breast cancer and plasma hormone levels.
2001 Jun
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.
2001 Jun
Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi).
2001 Jun
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women.
2001 Jun 1
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.
2001 Jun 15
[Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers].
2001 Mar
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.
2001 Mar
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats.
2001 Mar
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men.
2001 Mar
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.
2001 Mar
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease.
2001 Mar
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes.
2001 Mar
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.
2001 May
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
Effects of transdermal testosterone on bone and muscle in older men with low bioavailable testosterone levels.
2001 May
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model.
2001 May
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.
2001 May 15
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Vaginal route is possible: The recommended dose is 2.0 to 4.0 g intravaginally per day, adjusted to the lowest amount that controls symptoms http://www.rxlist.com/estragyn-drug.htm
5 pellets 3 times a day until symptoms are relieved
Route of Administration: Oral
Study was designed to discover filovirus entry inhibitors in a drug library of commercial medicines. One thousand and six hundred drugs were screened using the ZEBOV-GP/HIV model, a pseudovirus formed by an HIV-core packed with the Zaire Ebola virus glycoprotein. Was identified 12 gonadal hormone drugs with inhibitory activities in ZEBOV-GP/HIV entry at final concentration of 10 μmol x L(-1). One of them with moderate activity was estrone IC50: 6.87 ± 0.03 μmol-L1
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:22:59 UTC 2021
Edited
by admin
on Sat Jun 26 10:22:59 UTC 2021
Record UNII
QTL48N278K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRONE SULFATE
MI  
Common Name English
ESTRONE 3 SULFATE
Common Name English
ESTRONE-3-SULFATE
Common Name English
ESTRONE-3-SULPHATE
Common Name English
ESTRONE, HYDROGEN SULFATE
Common Name English
US-2917522
Code English
ESTRONE SULFATE [MI]
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(SULFOOXY)-
Systematic Name English
ESTRADIOL METABOLITE (E1S)
Common Name English
ESTRA-1,3,5 (10)-TRIENE-17-ONE-3-YL-SULFATE
Common Name English
ESTRONE BISULFATE
Common Name English
CONJUGOL
Brand Name English
PRICE
Brand Name English
ESTRONE HEMISULFATE
Common Name English
ESTRONE HYDROGEN SULFATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
LOINC 15355-1
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
Code System Code Type Description
MESH
C017296
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
IUPHAR
4749
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
CAS
481-97-0
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
DRUG BANK
DB04574
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
MERCK INDEX
M5033
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY Merck Index
EVMPD
SUB32459
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
PUBCHEM
3001028
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
DRUG CENTRAL
4857
Created by admin on Sat Jun 26 10:22:59 UTC 2021 , Edited by admin on Sat Jun 26 10:22:59 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Vmax
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.