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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 C18H21O5S
Molecular Weight 349.421
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.
2001
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.
2001
Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.
2001 Aug 9
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
The effects of PCB exposure and fish consumption on endogenous hormones.
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
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
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys.
2001 Jun 15
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.
2001 May
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta.
2001 May
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.
2001 May-Jun
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
Endocrinology of gynaecomastia.
2001 Nov
Regulation of human apolipoprotein A-I gene expression by equine estrogens.
2001 Nov
Tibolone: a compound with tissue specific inhibitory effects on sulfatase.
2001 Oct 25
[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
Polymorphisms in OATP-C: identification of multiple allelic variants associated with altered transport activity among European- and African-Americans.
2001 Sep 21
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
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
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
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 Feb 22
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
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
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
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
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 Fri Dec 15 16:35:36 GMT 2023
Edited
by admin
on Fri Dec 15 16:35:36 GMT 2023
Record UNII
6K6FDA543A
Record Status Validated (UNII)
Record Version
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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 Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
Code System Code Type Description
NSC
18313
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
FDA UNII
6K6FDA543A
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
CAS
438-67-5
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
PUBCHEM
23667301
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
DRUG BANK
DB00286
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
NCI_THESAURUS
C61942
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
DAILYMED
6K6FDA543A
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
CHEBI
8389
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
EVMPD
SUB01976MIG
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID00860005
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
MESH
C017296
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-120-4
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
SMS_ID
100000092374
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY
RXCUI
91428
Created by admin on Fri Dec 15 16:35:36 GMT 2023 , Edited by admin on Fri Dec 15 16:35:36 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY