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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

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

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

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
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000 Nov
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa.
2000 Oct
Biological effects of hormone replacement therapy in relation to serum estradiol levels.
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
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
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase.
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
Estrogen and androgen influence hypothalamic AVP and CRF concentrations in fetal and adult sheep.
2001 Apr 2
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.
2001 Apr 20
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.
2001 Apr 6
By the way, doctor. I've been taking hormone replacement with Premarin and Provera for 12 years. Now that I'm 68 years old, I'd like to stop taking the hormones, but I don't know how. What is the best way to get off HRT?
2001 Feb
Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver.
2001 Feb
Dietary oleoyl-estrone delays the growth rate of young rats.
2001 Feb
Periovulatory changes in catfish ovarian oestradiol-17beta, oestrogen-2-hydroxylase and catechol-O-methyltransferase during GnRH analogue-induced ovulation and in vitro induction of oocyte maturation by catecholoestrogens.
2001 Feb
Predominant 4-hydroxylation of estradiol by constitutive cytochrome P450s in the female ACI rat liver.
2001 Feb
Differential in vitro suppressive effects of steroids on leukocyte phagocytosis in two teleosts, tilapia and common carp.
2001 Feb
The human estrogen receptor alpha dimer binds a single SRC-1 coactivator molecule with an affinity dictated by agonist structure.
2001 Feb 23
Evidence that a metabolite of equine estrogens, 4-hydroxyequilenin, induces cellular transformation in vitro.
2001 Jan
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins.
2001 Jan
Hormone contents in peripheral tissues after correct and off-label use of growth promoting hormones in cattle: effect of the implant preparations Filaplix-H, Raglo, Synovex-H and Synovex Plus.
2001 Jan
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment.
2001 Jan
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.
2001 Jan 22
Searching for the physiological function of 17beta-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus: studies of substrate specificity and expression analysis.
2001 Jan 22
Mechanisms of estradiol inactivation in primate endometrium.
2001 Jan 22
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).
2001 Jan 22
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.
2001 Jan 22
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Structure and function of 17beta-hydroxysteroid dehydrogenase type 1 and type 2.
2001 Jan 22
Beneficial effects of pravastatin in peri- and postmenopausal hyperlipidemic women: a 5-year study on serum lipid and sex hormone levels.
2001 Jan 31
Characteristics of cystic breast disease with special regard to breast cancer development.
2001 Jan-Feb
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.
2001 Jun
Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke.
2001 Mar
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.
2001 Mar
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.
2001 Mar 2
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.
2001 May
2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells.
2001 May
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
Regulation of human apolipoprotein A-I gene expression by equine estrogens.
2001 Nov
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
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
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
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer.
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
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 20:36:32 GMT 2025
Edited
by admin
on Mon Mar 31 20:36:32 GMT 2025
Record UNII
QTL48N278K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CONJUGOL
Preferred Name English
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
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 Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
LOINC 15355-1
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
Code System Code Type Description
SMS_ID
100000124394
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
WIKIPEDIA
Estrone sulfate (medication)
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
MESH
C017296
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
NCI_THESAURUS
C1091
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
WIKIPEDIA
ESTRONE SULFATE
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-575-9
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
FDA UNII
QTL48N278K
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
IUPHAR
4749
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
CAS
481-97-0
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
DRUG BANK
DB04574
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
MERCK INDEX
m5033
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY Merck Index
CHEBI
17474
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
EVMPD
SUB32459
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
PUBCHEM
3001028
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID50891501
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
DRUG CENTRAL
4857
Created by admin on Mon Mar 31 20:36:32 GMT 2025 , Edited by admin on Mon Mar 31 20:36:32 GMT 2025
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.