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

C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=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 350.429
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
Functional characterization of the mouse organic-anion-transporting polypeptide 2.
2002-08-19
Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being.
2002-08-15
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.
2002-08
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
2002-07-26
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.
2002-07-16
Does place of birth influence endogenous hormone levels in Asian-American women?
2002-07-01
Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being.
2002-07
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.
2002-07
Mammary secretion of oestrogens in the cow.
2002-07
Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial.
2002-06-24
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.
2002-06
The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids.
2002-05
Specific radioimmunoassay of estrone sulfate. Application to measurement in male plasma.
2002-05
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells.
2002-05
Effects of lactation length and an exogenous progesterone and estradiol-17beta regimen during embryo attachment on endogenous steroid concentrations and embryo survival in sows.
2002-05
The choice of hormone replacement therapy or statin therapy in the treatment of hyperlipidemic postmenopausal women.
2002-05
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.
2002-05
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.
2002-05
Association of CYP1B1 polymorphisms and breast cancer risk.
2002-05
Transport of the sulfated, amidated bile acid, sulfolithocholyltaurine, into rat hepatocytes is mediated by Oatp1 and Oatp2.
2002-05
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies.
2002-04-17
Peripheral changes in estrone sulfate concentration during the first trimester of gestation in cattle: comparison with unconjugated estrogens and relationship to fetal number.
2002-04-15
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002-04
Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent.
2002-04
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta.
2002-04
Bone loss at the femoral neck in premenopausal white women: effects of weight change and sex-hormone levels.
2002-04
An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins.
2002-04
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.
2002-03-08
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002-03-08
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.
2002-03
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.
2002-03
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.
2002-03
Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and Multidrug resistance-associated protein 2 (MRP2/ABCC2).
2002-02-22
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.
2002-02-01
A randomized isoflavone intervention among premenopausal women.
2002-02
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.
2002-01
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
[Effects of oral administration of estrogen replacement therapy in surgical menopause].
2001-12
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.
2001-12
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001-12
The antihyperglycemic effect of estrone sulfate in genetically obese-diabetic (ob/ob) mice is associated with reduced hepatic glucose-6-phosphatase.
2001-12
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?
2001-12
The effects of PCB exposure and fish consumption on endogenous hormones.
2001-12
Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases.
2001-12
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.
2001-11
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women].
2001-09
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
2001
Estrogen sulfamates: a new approach to oral estrogen therapy.
2001
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 Mon Mar 31 20:36:32 GMT 2025
Edited
by admin
on Mon Mar 31 20:36:32 GMT 2025
Record UNII
QTL48N278K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CONJUGOL
Preferred Name English
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
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 Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
LOINC 15355-1
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
Code System Code Type Description
SMS_ID
100000124394
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
WIKIPEDIA
Estrone sulfate (medication)
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
MESH
C017296
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
IUPHAR
4749
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
CAS
481-97-0
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
DRUG BANK
DB04574
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
MERCK INDEX
m5033
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY Merck Index
CHEBI
17474
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
EVMPD
SUB32459
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
PUBCHEM
3001028
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID50891501
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
DRUG CENTRAL
4857
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.