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: https://www.ncbi.nlm.nih.gov/pubmed/27960570 | https://www.accessdata.fda.gov/cdrh_docs/pdf/K970915.pdfhttp://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://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 2637		7.0 nM [EC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2637

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 426 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 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Prostate cancer 177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27960570	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Obesity 204 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 8307	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 8307	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 8307	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 651	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 1670	substrate 985		inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 383 P-gp 1491 UGT1A10 289 UGT1A3 421 UGT2A1 32 CYP1A1 344 CYP1A2 1013 CYP2B6 648 CYP2E1 633	P-gp 252

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1588	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 289	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 1013	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 421	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 32	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 344	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 648	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 985	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 633	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 383	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1670	substrate 3264 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 1603	inhibitor 1584 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
Biological effects of hormone replacement therapy in relation to serum estradiol levels.	2001	11815726
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.	2001	11721885
Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation.	2001 Apr	11259571
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.	2001 Apr	11250930
Effects of testosterone precursor supplementation on intensive weight training.	2001 Apr	11403114
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.	2001 Apr	11352550
Oestrogens and oestrogenic activity in raw and treated water in Severn Trent Water.	2001 Apr	11268844
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.	2001 Apr 20	11278596
Postmenopausal endogenous oestrogens and risk of endometrial cancer: results of a prospective study.	2001 Apr 6	11286480
Estrogen replacement therapy after breast cancer: a 12-year follow-up.	2001 Dec	11776498
4-hydroxy-2',4',6'-trichlorobiphenyl and 4-hydroxy-2',3',4',5'-tetrachlorobiphenyl are estrogenic in rainbow trout.	2001 Feb	11351435
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.	2001 Feb 28	11223173
Evolution of 17beta-HSD type 4, a multifunctional protein of beta-oxidation.	2001 Jan 22	11165031
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).	2001 Jan 22	11165022
Non-steroidal and steroidal sulfamates: new drugs for cancer therapy.	2001 Jan 22	11165021
Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.	2001 Jan 9	11141067
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	11465375
Molecular basis of perinatal changes in UDP-glucuronosyltransferase activity in maternal rat liver.	2001 Jul	11408524
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.	2001 Jun	11397902
Regulation of leptin and leptin receptor in baboon pregnancy: effects of advancing gestation and fetectomy.	2001 Jun	11397849
Increased prostacyclin synthesis by atherosclerotic arteries from estrogen-treated monkeys.	2001 Jun 15	11459430
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.	2001 Mar	11355746
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.	2001 Mar	11284326
Endogenous sex hormone levels in postmenopausal women with Alzheimer's disease.	2001 Mar	11238492
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
Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.	2001 Mar 19	11267661
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
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	11294972
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.	2001 May 15	11336660
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.	2001 May-Jun	11392373
Regulation of human apolipoprotein A-I gene expression by equine estrogens.	2001 Nov	11714848
Micronized progesterone regulation of the endometrial glandular cycling pool.	2001 Oct	11603222
[Prevention and treatment of recurrent urinary system infection with estrogen cream in postmenopausal women].	2001 Sep	11769665
Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C.	2001 Sep	11683238
Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES).	2002 Apr	11983489
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
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
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.	2002 Jul	12142247
Mammary secretion of oestrogens in the cow.	2002 Jul	12142232
Role of aromatic transmembrane residues of the organic anion transporter, rOAT3, in substrate recognition.	2002 Jul 16	12102636
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.	2002 Jun	12042670
Alveolar and postcranial bone density in postmenopausal women receiving hormone/estrogen replacement therapy: a randomized, double-blind, placebo-controlled trial.	2002 Jun 24	12076241
Conformational analysis of a 4-hydroxyequilenin Guanine adduct using density functional theory.	2002 May	12018985

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 17 10:38:11 UTC 2022` Edited by `admin` on `Sat Dec 17 10:38:11 UTC 2022`
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