U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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 testosterone precursor supplementation on intensive weight training.
2001 Apr
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).
2001 Apr
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
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
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase.
2001 Apr
Measurement of urinary and fecal steroid metabolites during the ovarian cycle in captive and wild Japanese macaques, Macaca fuscata.
2001 Apr
Oestrogens and oestrogenic activity in raw and treated water in Severn Trent Water.
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
Do urinary estrogen metabolites reflect the differences in breast cancer risk between Singapore Chinese and United States African-American and white women?
2001 Apr 15
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3.
2001 Apr 15
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.
2001 Apr 20
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.
2001 Apr 6
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
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.
2001 Jan 30
The selective estrogen enzyme modulator (SEEM) in breast cancer.
2001 Jan-Mar
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
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
[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
Can variability in the hormonal status of elderly women assist in the decision to administer estrogens?
2001 Mar
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary.
2001 Mar
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease.
2001 Mar
Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection.
2001 Mar 16
Novel inhibitors of the enzyme estrone sulfatase (ES).
2001 Mar 26
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
Urinary excretion pattern of catecholestrogens in preovulatory LH surge during the 4-day estrous cycle of rats.
2001 May
In vitro generation of peroxynitrite by 2- and 4-hydroxyestrogens in the presence of nitric oxide.
2001 May
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
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
Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells.
2001 May
A polymorphism in CYP17 and endometrial cancer risk.
2001 May 15
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.
2001 May 15
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
2001 May-Jun
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.
2001 May-Jun
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
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