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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21O5S.Na
Molecular Weight 372.411
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE SODIUM SULFATE

SMILES

[Na+].[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=VUCAHVBMSFIGAI-ZFINNJDLSA-M
InChI=1S/C18H22O5S.Na/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 Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H21O5S
Molecular Weight 349.421
Charge -1
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
Estrogen sulfamates: a new approach to oral estrogen therapy.
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
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Cholesterol sulfate: a new adhesive molecule for platelets.
2001 Apr 24
Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women.
2001 Aug
[Effects of oral administration of estrogen replacement therapy in surgical menopause].
2001 Dec
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001 Dec
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 Dec
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.
2001 Jan
Effect of GnRH immunisation on hormonal levels, sexual behaviour, semen quality and testicular morphology in mature stallions.
2001 Jan
Sleep in menopause: differential effects of two forms of hormone replacement therapy.
2001 Jan-Feb
Paradoxical effect of estradiol: it can block its own bioformation in human breast cancer cells.
2001 Jul
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
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.
2001 Jun
Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke.
2001 Mar
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes.
2001 Mar
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.
2001 Mar 19
Regulation of human apolipoprotein A-I gene expression by equine estrogens.
2001 Nov
Micronized progesterone regulation of the endometrial glandular cycling pool.
2001 Oct
Tibolone: a compound with tissue specific inhibitory effects on sulfatase.
2001 Oct 25
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.
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
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
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
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
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.
2002 Jun
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.
2002 Mar
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
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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:00:59 UTC 2023
Edited
by admin
on Thu Jul 06 00:00:59 UTC 2023
Record UNII
6K6FDA543A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRONE SODIUM SULFATE
VANDF   WHO-DD  
Common Name English
ESTRONE SODIUM SULFATE [VANDF]
Common Name English
SODIUM 17-OXOESTRA-1,3,5(10)-TRIEN-3-YL SULFATE
Systematic Name English
SODIUM (8R,9S,13S,14S)-13-METHYL-17-OXO-7,8,9,11,12,13,14,15,16,17-DECAHYDRO-6H-CYCLOPENTA(A)PHENANTHREN-3-YL SULFATE
Common Name English
SODIUM ESTRONE SULFATE
Common Name English
SODIUM ESTRONE SULPHATE
Common Name English
17-OXOESTRA-1,3,5(10)-TRIEN-3-YL SODIUM SULFATE
Systematic Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(SULFOOXY)-, SODIUM SALT
Common Name English
Estrone sodium sulfate [WHO-DD]
Common Name English
ESTRONE SODIUM SULPHATE
Common Name English
NSC-18313
Code English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
Code System Code Type Description
NSC
18313
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
FDA UNII
6K6FDA543A
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
CAS
438-67-5
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
PUBCHEM
23667301
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
DRUG BANK
DB00286
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
NCI_THESAURUS
C61942
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
DAILYMED
6K6FDA543A
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
CHEBI
8389
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
EVMPD
SUB01976MIG
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID00860005
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
MESH
C017296
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-120-4
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
SMS_ID
100000092374
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY
RXCUI
91428
Created by admin on Thu Jul 06 00:00:59 UTC 2023 , Edited by admin on Thu Jul 06 00:00:59 UTC 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY