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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+].C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS([O-])(=O)=O)=C4)[C@@H]1CCC2=O

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 22.98976928
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

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
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
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3.
2001 Apr 15
Structural and functional consequences of inactivation of human glutathione S-transferase P1-1 mediated by the catechol metabolite of equine estrogens, 4-hydroxyequilenin.
2001 Apr 17
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.
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
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
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
Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women.
2001 Jun
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys.
2001 Jun 15
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.
2001 May 1
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3.
2001 May 8
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
Micronized progesterone regulation of the endometrial glandular cycling pool.
2001 Oct
Short-term oral estrogen replacement therapy does not augment endothelium-independent myocardial perfusion in postmenopausal women.
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
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
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
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
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.
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
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 18:32:07 GMT 2025
Edited
by admin
on Mon Mar 31 18:32:07 GMT 2025
Record UNII
6K6FDA543A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRONE SODIUM SULFATE
VANDF   WHO-DD  
Common Name English
NSC-18313
Preferred 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
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
Code System Code Type Description
NSC
18313
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
FDA UNII
6K6FDA543A
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
CAS
438-67-5
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
PUBCHEM
23667301
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
DRUG BANK
DB00286
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
NCI_THESAURUS
C61942
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
DAILYMED
6K6FDA543A
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
CHEBI
8389
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
EVMPD
SUB01976MIG
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID00860005
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
MESH
C017296
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-120-4
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
SMS_ID
100000092374
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY
RXCUI
91428
Created by admin on Mon Mar 31 18:32:07 GMT 2025 , Edited by admin on Mon Mar 31 18:32:07 GMT 2025
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY