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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O5S
Molecular Weight 350.429
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE SULFATE

SMILES

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

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 350.429
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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. It’s used as hameopatic in management of premenopausal and postmenopausal symptoms. In 1929, Butenandt isolated estrone from the urine of pregnant women. Estrone is known to be a carcinogen for human females as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure. In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.

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
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
2001
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.
2001
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
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
Oestrogens and oestrogenic activity in raw and treated water in Severn Trent Water.
2001 Apr
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
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001 Dec
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout.
2001 Feb
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.
2001 Feb 28
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.
2001 Jan 22
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).
2001 Jan 22
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.
2001 Jan 22
Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.
2001 Jan 9
Early postnatal plasma concentrations of testicular steroid hormones, pubertal development, and carcass leanness as potential indicators of boar taint in market weight intact male pigs.
2001 Jul
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
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
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys.
2001 Jun 15
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.
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
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
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.
2001 Mar 19
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
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
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.
2001 May 15
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.
2001 May-Jun
Regulation of human apolipoprotein A-I gene expression by equine estrogens.
2001 Nov
Micronized progesterone regulation of the endometrial glandular cycling pool.
2001 Oct
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women].
2001 Sep
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.
2001 Sep
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
Peripheral changes in estrone sulfate concentration during the first trimester of gestation in cattle: comparison with unconjugated estrogens and relationship to fetal number.
2002 Apr 15
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.
2002 Aug
Functional characterization of the mouse organic-anion-transporting polypeptide 2.
2002 Aug 19
Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being.
2002 Jul
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.
2002 Jul
Mammary secretion of oestrogens in the cow.
2002 Jul
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.
2002 Jul 16
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.
2002 Jun
Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial.
2002 Jun 24
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.
2002 May
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
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 17 10:38:11 UTC 2022
Edited
by admin
on Sat Dec 17 10:38:11 UTC 2022
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 Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
LOINC 15355-1
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
Code System Code Type Description
WIKIPEDIA
Estrone sulfate (medication)
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
MESH
C017296
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
IUPHAR
4749
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
CAS
481-97-0
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
DRUG BANK
DB04574
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
MERCK INDEX
M5033
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY Merck Index
CHEBI
17474
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
EVMPD
SUB32459
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
PUBCHEM
3001028
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
EPA CompTox
DTXSID50891501
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
DRUG CENTRAL
4857
Created by admin on Sat Dec 17 10:38:11 UTC 2022 , Edited by admin on Sat Dec 17 10:38:11 UTC 2022
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
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.