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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21O5S.K
Molecular Weight 388.5214
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POTASSIUM ESTRONE SULFATE

SMILES

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

InChI

InChIKey=CUQHOFAEIPGLBH-ZFINNJDLSA-M
InChI=1S/C18H22O5S.K/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);/q;+1/p-1/t14-,15-,16+,18+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C18H21O5S
Molecular Weight 349.4231
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula K
Molecular Weight 39.0983
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.
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
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
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
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.
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
Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep.
2001 Apr 2
Acid dissociation constant, a potential physicochemical factor in the inhibition of the enzyme estrone sulfatase (ES).
2001 Apr 9
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.
2001 Feb
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout.
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
Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.
2001 Feb
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
Mechanisms of estradiol inactivation in primate endometrium.
2001 Jan 22
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.
2001 Jan 22
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung.
2001 Jan 22
Structure and function of 17beta-hydroxysteroid dehydrogenase type 1 and type 2.
2001 Jan 22
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.
2001 Jan 30
Chalcones are potent inhibitors of aromatase and 17beta-hydroxysteroid dehydrogenase activities.
2001 Jan 5
Characteristics of cystic breast disease with special regard to breast cancer development.
2001 Jan-Feb
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
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
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
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.
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
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.
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
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
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells.
2001 May
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.
2001 May 15
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:42:52 UTC 2021
Edited
by admin
on Sat Jun 26 14:42:52 UTC 2021
Record UNII
C354LET0O4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POTASSIUM ESTRONE SULFATE
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(SULFOOXY)-, POTASSIUM SALT
Common Name English
NSC-18054
Code English
Code System Code Type Description
MESH
C017296
Created by admin on Sat Jun 26 14:42:52 UTC 2021 , Edited by admin on Sat Jun 26 14:42:52 UTC 2021
PRIMARY
DRUG BANK
DBSALT002493
Created by admin on Sat Jun 26 14:42:52 UTC 2021 , Edited by admin on Sat Jun 26 14:42:52 UTC 2021
PRIMARY
PUBCHEM
23674502
Created by admin on Sat Jun 26 14:42:52 UTC 2021 , Edited by admin on Sat Jun 26 14:42:52 UTC 2021
PRIMARY
FDA UNII
C354LET0O4
Created by admin on Sat Jun 26 14:42:52 UTC 2021 , Edited by admin on Sat Jun 26 14:42:52 UTC 2021
PRIMARY
CAS
1240-04-6
Created by admin on Sat Jun 26 14:42:52 UTC 2021 , Edited by admin on Sat Jun 26 14:42:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
214-985-1
Created by admin on Sat Jun 26 14:42:52 UTC 2021 , Edited by admin on Sat Jun 26 14:42:52 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE