ESTRONE SULFATE

First marketed in 1931

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 Search

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

Description
Sources: http://www.drugfuture.com/chemdata/estrone.html | http://pubs.acs.org/doi/abs/10.1021/ja01159a529?journalCode=jacsat | http://pubs.acs.org/doi/abs/10.1021/ja00536a023https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttps://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031
Curator's Comment: description was created based on several sources, including http://www.drugbank.ca/drugs/DB00655 https://www.ncbi.nlm.nih.gov/pubmed/2011412 https://www.ncbi.nlm.nih.gov/pubmed/17943537

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6863279 \| https://www.ncbi.nlm.nih.gov/pubmed/15081034	Agonist 2678		7.0 nM [EC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Benign breast disease 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Endometrial cancer 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Infertility 14 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Amenorrhea 18 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Ovarian diseases 7 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Precocious puberty 8 Sources: https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Menopausal and postmenopausal disorder 10 Sources: http://www.rxlist.com/estragyn-drug.htm http://chealth.canoe.com/drug/getdrug/estragyn-vaginal-cream https://www.drugs.com/international/estrone.html	Primary	Approved 8429	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.
Endometrial hyperplasia/carcinoma 7 Sources: http://www.rxlist.com/estragyn-drug.htm http://chealth.canoe.com/drug/getdrug/estragyn-vaginal-cream https://www.drugs.com/international/estrone.html	Primary	Approved 8429	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.
Menopausal and postmenopausal disorders 7 Sources: http://www.druglib.com/activeingredient/estrone/	Primary	Approved 8429	THEELIN Approved Use For management of Menopausal and postmenopausal disorders
Premenstrual syndrome 37 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=83dd22a0-7c59-11e6-84ff-424c58303031	Palliative	Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
733 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/	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

Value	Dose	Co-administered	Analyte	Population
550 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/908445/	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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037		inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 395 P-gp 1537 UGT1A10 291 UGT1A3 422 UGT2A1 32 CYP1A1 349 CYP1A2 1054 CYP2B6 664 CYP2E1 667	P-gp 257

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 32	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes	weak (co-administration study) Comment: Coadministration with ketoconazole (CYP3A4 inhibitor) resulted in estrone expsoure increase of ~1.4 foold Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/19129680/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17263	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17263
ChemicalBook	CB5741416	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5741416
MolPort	MolPort-001-742-529	https://www.molport.com/shop/molecule-link/MolPort-001-742-529
Selleck Chemicals	Estrone	http://www.selleckchem.com/products/Estrone.html
ZINC	ZINC000013509425	http://zinc15.docking.org/substances/ZINC000013509425
eMolecules	29543531	https://www.emolecules.com/cgi-bin/more?vid=29543531
eMolecules	511617	https://www.emolecules.com/cgi-bin/more?vid=511617

PubMed

Title	Date	PubMed
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.	2000 Feb 11	10660625
Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells.	2000 Jan-Feb	10731640
Estrone, but not 17 beta-estradiol, attenuates kainate-induced seizures and toxicity in male mice.	2001	11409300
Effects of testosterone precursor supplementation on intensive weight training.	2001 Apr	11403114
High metabolization of catecholestrogens by type 1 estrogen sulfotransferase (hEST1).	2001 Apr	11358677
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.	2001 Apr 20	11306210
Cholesterol sulfate: a new adhesive molecule for platelets.	2001 Apr 24	11319189
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.	2001 Apr 6	11286480
Comparison of estrogen and androgen levels after oral estrogen replacement therapy.	2001 Dec	11789085
Estrogen replacement therapy after breast cancer: a 12-year follow-up.	2001 Dec	11776498
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	11751102
Synthesis and biological evaluation of two new radiolabelled estrogens: [125I](E)-3-methoxy-17alpha-iodovinylestra-1,3,5(10),6-tetraen-17beta-ol and.	2001 Feb	11200884
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	11182761
Predominant 4-hydroxylation of estradiol by constitutive cytochrome P450s in the female ACI rat liver.	2001 Feb	11181446
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.	2001 Feb 28	11223173
Effects of estrone sulfate alone or with medroxyprogesterone acetate on serum lipoprotein levels in postmenopausal women.	2001 Jan	11152917
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	11297194
Chalcones are potent inhibitors of aromatase and 17beta-hydroxysteroid dehydrogenase activities.	2001 Jan 5	11205867
Influence of endogenous androgens on carotid wall in postmenopausal women.	2001 Jan-Feb	11201514
The selective estrogen enzyme modulator (SEEM) in breast cancer.	2001 Jan-Mar	11384867
Menopausal experiences and bone density of Mayan women in Yucatan, Mexico.	2001 Jul-Aug	11400221
Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women.	2001 Jun	11397883
Serum levels of C-reactive protein are associated with obesity, weight gain, and hormone replacement therapy in healthy postmenopausal women.	2001 Jun 1	11390329
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.	2001 Jun 15	11389699
Sulfation is rate limiting in the futile cycling between estrone and estrone sulfate in enriched periportal and perivenous rat hepatocytes.	2001 Mar	11181504
Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection.	2001 Mar 16	11293581
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.	2001 Mar 2	11102445
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.	2001 Mar-Apr	11371017
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.	2001 May	11368557
Influence of neoadjuvant anastrozole (Arimidex) on intratumoral estrogen levels and proliferation markers in patients with locally advanced breast cancer.	2001 May	11350888
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.	2001 May	11355334
Immature ovaries and polycystic kidneys in the congenital polycystic kidney mouse may be due to abnormal sex steroid metabolism.	2001 May 15	11369455
Serum hormones and the alcohol-breast cancer association in postmenopausal women.	2001 May 2	11333294
Arginine 454 and lysine 370 are essential for the anion specificity of the organic anion transporter, rOAT3.	2001 May 8	11331016
Markedly elevated levels of estrone sulfate after long-term oral, but not transdermal, administration of estradiol in postmenopausal women.	2001 May-Jun	11355042
Micronized progesterone regulation of the endometrial glandular cycling pool.	2001 Oct	11603222
Hormone replacement therapy for cognitive function in postmenopausal women.	2002	12137675
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).	2002 Apr	11983489
Characterization of an organic anion-transporting polypeptide (OATP-B) in human placenta.	2002 Apr	11932330
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	12041697
Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.	2002 Aug	12175967
Hormonal measurements in late pregnancy and parturition in dairy cows--possible tools to monitor foetal well being.	2002 Aug 15	12137978
Functional characterization of the mouse organic-anion-transporting polypeptide 2.	2002 Aug 19	12101011
Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being.	2002 Jul	12142248
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.	2002 Jun	12042670
The IGF-system in healthy pre- and postmenopausal women: relations to demographic variables and sex-steroids.	2002 May	12127047
Specific radioimmunoassay of estrone sulfate. Application to measurement in male plasma.	2002 May	12127046
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.	2002 May	12015519
Association of CYP1B1 polymorphisms and breast cancer risk.	2002 May	12010864

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 GMT 2023` Edited by `admin` on `Sat Dec 16 00:29:08 GMT 2023`
Record UNII	QTL48N278K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESTRONE SULFATE

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