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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O5S
Molecular Weight 350.429
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
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
Estrogen sulfamates: a new approach to oral estrogen therapy.
2001
[Effects of oral administration of estrogen replacement therapy in surgical menopause].
2001 Dec
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.
2001 Dec
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001 Dec
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.
2001 Dec
By the way, Doctor. Whenever I read about the effects of hormone replacement therapy (HRT), the researchers always seem to use 0.625 mg of Premarin. I'm taking 1 mg of Estrace daily. How does this compare to the standard dose of Premarin?
2001 Dec
Effect of transforming growth factor-beta1, insulin-like growth factor-I and insulin-like growth factor-II on cell growth and oestrogen metabolism in human breast cancer cell lines.
2001 Nov
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women].
2001 Sep
Hormone replacement therapy for cognitive function in postmenopausal women.
2002
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe.
2002
The role of cytokines in regulating estrogen synthesis: implications for the etiology of breast cancer.
2002
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent.
2002 Apr
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta.
2002 Apr
Bone loss at the femoral neck in premenopausal white women: effects of weight change and sex-hormone levels.
2002 Apr
An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins.
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
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies.
2002 Apr 17
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.
2002 Aug
Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being.
2002 Aug 15
Functional characterization of the mouse organic-anion-transporting polypeptide 2.
2002 Aug 19
A randomized isoflavone intervention among premenopausal women.
2002 Feb
Influence of letrozole and anastrozole on total body aromatization and plasma estrogen levels in postmenopausal breast cancer patients evaluated in a randomized, cross-over study.
2002 Feb 1
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.
2002 Jan
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
Does place of birth influence endogenous hormone levels in Asian-American women?
2002 Jul 1
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.
2002 Jul 16
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
2002 Jul 26
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
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.
2002 Mar
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.
2002 Mar
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.
2002 Mar
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.
2002 Mar 8
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids.
2002 May
Specific radioimmunoassay of estrone sulfate. Application to measurement in male plasma.
2002 May
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells.
2002 May
Effects of lactation length and an exogenous progesterone and estradiol-17beta regimen during embryo attachment on endogenous steroid concentrations and embryo survival in sows.
2002 May
The choice of hormone replacement therapy or statin therapy in the treatment of hyperlipidemic postmenopausal women.
2002 May
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.
2002 May
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.
2002 May
Association of CYP1B1 polymorphisms and breast cancer risk.
2002 May
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
2002 May
A new route to (+)-estrone using a bicyclo[3.2.1]octane chiral building block.
2003 Jan
Formal enantioselective synthesis of (+)-estrone.
2007 Mar 15
Catalytic asymmetric Torgov cyclization: a concise total synthesis of (+)-estrone.
2014 Aug 11
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
Estrone is available in the following doses: Estrone 2 Mg/ml Intramuscular Solution Estrone 5 Mg/ml Intramuscular Solution Estrone Compounding Powder Forms of Medication Estrone is available in the following forms: Injectable Solution Injectable Suspension Vaginal Suppository
Route of Administration: Intramuscular
At 1.0 x 10(-8) M, estrone promoted growth of MTW9/PL cells established from the carcinogen-induced hormone-responsive MT-W9A rat mammary tumor of a Wistar-Furth (W/Fu) rat.
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 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
LOINC 15355-1
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
Code System Code Type Description
SMS_ID
100000124394
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
WIKIPEDIA
Estrone sulfate (medication)
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
MESH
C017296
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
IUPHAR
4749
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
CAS
481-97-0
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
DRUG BANK
DB04574
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
MERCK INDEX
m5033
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY Merck Index
CHEBI
17474
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
EVMPD
SUB32459
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
PUBCHEM
3001028
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID50891501
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
DRUG CENTRAL
4857
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY