ESTRONE

First marketed in 1931

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H22O2
Molecular Weight	270.3661
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(O)C=C4

InChI

InChIKey=DNXHEGUUPJUMQT-CBZIJGRNSA-N

InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H22O2
Molecular Weight	270.3661
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 2662		7.0 nM [EC50]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011412	Agonist 2662

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 431 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 175 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 8360	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 8360	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 8360	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 663	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 1709	substrate 1010		inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A5 391 P-gp 1527 UGT1A10 290 UGT1A3 422 UGT2A1 32 CYP1A1 348 CYP1A2 1032 CYP2B6 660 CYP2E1 648	P-gp 257

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1626	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
UGT1A10 290	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	major
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	no
UGT1A3 422	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
UGT2A1 32	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/26220143/	weak
CYP1A1 348	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/9625734/	yes
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/10640505/	yes
CYP3A5 391	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/9635876/	yes
P-gp 1527	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/15290871/	yes
CYP3A4 1709	substrate 3326 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 1632	inhibitor 1613 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
Reproducibility of plasma and urinary sex hormone levels in premenopausal women over a one-year period.	1999 Dec	10613337
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.	2001	11455895
Home monitoring with the ClearPlan Easy Fertility Monitor for fertility awareness.	2001	11277337
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
Effects of oral and transdermal estrogen replacement therapy on markers of coagulation, fibrinolysis, inflammation and serum lipids and lipoproteins in postmenopausal women.	2001 Apr	11341495
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.	2001 Apr	11305597
Serum concentrations of 17beta-estradiol and estrone after multiple-dose administration of percutaneous estradiol gel in symptomatic menopausal women.	2001 Apr	11294513
Measurement of urinary and fecal steroid metabolites during the ovarian cycle in captive and wild Japanese macaques, Macaca fuscata.	2001 Apr	11283977
Up-regulation of steroid sulphatase activity in HL60 promyelocytic cells by retinoids and 1alpha,25-dihydroxyvitamin D3.	2001 Apr 15	11284723
Do urinary estrogen metabolites reflect the differences in breast cancer risk between Singapore Chinese and United States African-American and white women?	2001 Apr 15	11309288
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	11294649
Oral, water-soluble combined estrogen/calcium preparation for postmenopausal therapy.	2001 Apr 20	11306210
Identification of an amino acid residue in multidrug resistance protein 1 critical for conferring resistance to anthracyclines.	2001 Apr 20	11278596
Cholesterol sulfate: a new adhesive molecule for platelets.	2001 Apr 24	11319189
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	11743748
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.	2001 Feb	11398990
Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes).	2001 Feb	11351429
Plasma beta-endorphin levels in obese and non-obese patients with polycystic ovary disease.	2001 Feb	11293919
Inhibition of postmenopausal atherosclerosis progression: a comparison of the effects of conjugated equine estrogens and soy phytoestrogens.	2001 Jan	11231976
Sleep in menopause: differential effects of two forms of hormone replacement therapy.	2001 Jan-Feb	11201509
The selective estrogen enzyme modulator (SEEM) in breast cancer.	2001 Jan-Mar	11384867
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
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men.	2001 Mar	11303585
Can variability in the hormonal status of elderly women assist in the decision to administer estrogens?	2001 Mar	11268296
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
Metabolism of equilenin in MCF-7 and MDA-MB-231 human breast cancer cells.	2001 May	11368557
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta.	2001 May	11356157
Streamlined beta-galactosidase assay for analysis of recombinant yeast response to estrogens.	2001 May	11355334
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model.	2001 May	11294976
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
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.	2001 May 1	11301044
A polymorphism in CYP17 and endometrial cancer risk.	2001 May 15	11358812
Genotoxicity of the steroidal oestrogens oestrone and oestradiol: possible mechanism of uterine and mammary cancer development.	2001 May-Jun	11392373
Endocrinology of gynaecomastia.	2001 Nov	11732643
Tibolone: a compound with tissue specific inhibitory effects on sulfatase.	2001 Oct 25	11604225
Induction of puberty in the hypogonadal girl--practices and attitudes of pediatric endocrinologists in Europe.	2002	12006724
A randomized isoflavone intervention among premenopausal women.	2002 Feb	11867507
The bovine placenta; a source and target of steroid hormones: observations during the second half of gestation.	2002 Jul	12142247
A naturally occurring mutation in MRP1 results in a selective decrease in organic anion transport and in increased doxorubicin resistance.	2002 Jun	12042670
Nonsteroidal compounds designed to mimic potent steroid sulfatase inhibitors.	2002 Mar	11948019
Characterization of iodothyronine sulfatase activities in human and rat liver and placenta.	2002 Mar	11861502
Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1.	2002 Mar 8	12005172
Interaction of human organic anion transporters with various cephalosporin antibiotics.	2002 Mar 8	11909604
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.	2002 May	12015519

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 `Thu Jul 06 21:34:07 UTC 2023` Edited by `admin` on `Thu Jul 06 21:34:07 UTC 2023`
Record UNII	2DI9HA706A
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ESTRONE

Official Name

English

ESTRONE [MI]

Common Name

English

WAY 164397

Code

English

1,3,5-ESTRATRIEN-3-OL-17-ONE

Common Name

English

estrone [INN]

Common Name

English

FOLLICULIN

Common Name

English

ETHINYLESTRADIOL IMPURITY C [EP IMPURITY]

Common Name

English

THEELIN

Brand Name

English

FOLLICULAR-HORMONE

Common Name

English

ESTRONE [VANDF]

Common Name

English

FOLLICULINUM

Common Name

English

OESTRONE

Common Name

English

THELYKININ

Common Name

English

KETOHYDROXYESTRIN

Common Name

English

ESTRADIOL METABOLITE E1

Common Name

English

FOLLICULAR HORMONE

Common Name

English

TOKOKIN

Common Name

English

ESTRONE [ORANGE BOOK]

Common Name

English

FOLLICULINUM [HPUS]

Common Name

English

ESTRONE [USP-RS]

Common Name

English

ESTRONE [MART.]

Common Name

English

ESTRONE [JAN]

Common Name

English

3-HYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE

Systematic Name

English

ESTROGENIC SUBSTANCE

Brand Name

English

ESTRADIOL HEMIHYDRATE IMPURITY A [EP IMPURITY]

Common Name

English

Estrone [WHO-DD]

Common Name

English

ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-HYDROXY-

Systematic Name

English

ESTRONE [USP MONOGRAPH]

Common Name

English

ESTRONE [HSDB]

Common Name

English

(8R,9S,13S,14S)-3-HYDROXY-13-METHYL-6,7,8,9,11,12,13,14,15,16-DECAHYDRO-17H-CYCLOPENTA(A)PHENANTHREN-17-ONE

Systematic Name

English

NSC-9699

Code

English

Classification Tree Code System Code

LOINC

25403-7