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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

[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=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

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
Flaxseed consumption influences endogenous hormone concentrations in postmenopausal women.
2001
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.
2001
On call. My wife's doctor gave her Premarin for her cholesterol. I know it's a female hormone, but my cholesterol is also high, and I wonder if it could help me, too.
2001 Apr
Prospective randomized study of effects of unopposed estrogen replacement therapy on markers of coagulation and inflammation in postmenopausal women.
2001 Aug
Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.
2001 Aug 9
[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
The effects of PCB exposure and fish consumption on endogenous hormones.
2001 Dec
Effect of estrogen on endothelial dysfunction in postmenopausal women with diabetes.
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
Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone.
2001 Jun
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
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
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.
2001 May
Serum hormones and the alcohol-breast cancer association in postmenopausal women.
2001 May 2
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.
2001 May-Jun
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
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
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).
2002 Apr
Number of years since menopause: spontaneous bone loss is dependent but response to hormone replacement therapy is independent.
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
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
A randomized isoflavone intervention among premenopausal women.
2002 Feb
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
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
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.
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
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
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly 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
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 Sat Dec 16 00:29:08 UTC 2023
Edited
by admin
on Sat Dec 16 00:29:08 UTC 2023
Record UNII
QTL48N278K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CONJUGOL
Brand 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 Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
LOINC 15355-1
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
Code System Code Type Description
SMS_ID
100000124394
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
WIKIPEDIA
Estrone sulfate (medication)
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
MESH
C017296
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
IUPHAR
4749
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
CAS
481-97-0
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
DRUG BANK
DB04574
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
MERCK INDEX
m5033
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY Merck Index
CHEBI
17474
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
EVMPD
SUB32459
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
PUBCHEM
3001028
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID50891501
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
DRUG CENTRAL
4857
Created by admin on Sat Dec 16 00:29:08 UTC 2023 , Edited by admin on Sat Dec 16 00:29:08 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Vmax
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.