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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21O5S.K
Molecular Weight 388.52
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POTASSIUM ESTRONE SULFATE

SMILES

[K+].[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=CUQHOFAEIPGLBH-ZFINNJDLSA-M
InChI=1S/C18H22O5S.K/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 K
Molecular Weight 39.0983
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
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.
2001
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.
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
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
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
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
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
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout.
2001 Feb
Effect of GnRH immunisation on hormonal levels, sexual behaviour, semen quality and testicular morphology in mature stallions.
2001 Jan
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.
2001 Jan 30
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
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.
2001 Jul
Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women.
2001 Jun
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women.
2001 Jun 1
Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke.
2001 Mar
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.
2001 Mar
Daily oral oleoyl-estrone gavage induces a dose-dependent loss of fat in Wistar rats.
2001 Mar
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.
2001 May
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.
2001 May
Effects of transdermal testosterone on bone and muscle in older men with low bioavailable testosterone levels.
2001 May
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3.
2001 May 8
Endocrinology of gynaecomastia.
2001 Nov
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.
2001 Sep
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
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta.
2002 Apr
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
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.
2002 Jan
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.
2002 Jul
Does place of birth influence endogenous hormone levels in Asian-American women?
2002 Jul 1
Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice.
2002 Jul 26
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
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.
2002 May
Association of CYP1B1 polymorphisms and breast cancer risk.
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
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 15:16:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:55 GMT 2023
Record UNII
C354LET0O4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POTASSIUM ESTRONE SULFATE
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(SULFOOXY)-, POTASSIUM SALT
Common Name English
NSC-18054
Code English
Code System Code Type Description
MESH
C017296
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
DRUG BANK
DBSALT002493
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
PUBCHEM
23674502
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
FDA UNII
C354LET0O4
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
CAS
1240-04-6
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-985-1
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
NSC
18054
Created by admin on Fri Dec 15 15:16:55 GMT 2023 , Edited by admin on Fri Dec 15 15:16:55 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE